Transvestite

My craving for a man

I really don’t know how and when I began having cravings for men. I have always had a girlish body, thin build, small waist, very little body hair, although what I think that set me apart from most boys was my butt. I often was mistaken for a girl because of my bubble, heart shaped butt. I am not totally gay…. I guess, because girls do turn me on.
When I was growing up I would often go stay at my aunt’s house in the summer. I got to do fun things that I was not aloud to do at home like stay out late with friends and sometimes my cousin (whom was my age) and I would go drinking.
This particular summer I was around 14 years old when I went to visit my cousin. My cousin and I went to a party and I got really drunk. When we got back home I went straight to bed, that my cousin and I shared when I would visit. I managed to get out of clothes and put on a t-shirt and squeezed into some old track shorts that were really getting to small for me but that’s all I found at the time. Well it was around two in the morning when I felt someone touching my butt. I paid no mind since it was probably my cousin getting comfortable in bed and I was still quite drunk. I slipped back to sleep and was woke again by a hand caressing my ass. I was shocked, although I dared not to move. I laid there motionless as possible, I couldn’t believe that my cousin was grabbing my ass. As I laid there pretending to be asleep my cousin kept caressing my ass and gently squeezing it. I then felt something warm touch me, he was sliding it up and down my ass and thighs all the way up to my lower back. Could this be his dick? I thought to myself. After a few minutes I felt his finger squeeze into my tight shorts as he gently rubbed my ass and slowly slipping his finger between my ass cheeks and slowly rubbing my hole. He then gently tried to stick his finger inside me but it started to hurt so I tried to act restless in my sleep. He then stopped and left his hand inside my shorts hopping I would go back to sleep. He did not try anything else that night. He removed his hand and went to sleep. I could not fall back asleep that night having my cousin feel me up made me very horny. I heard my cousin snoring so I gently took the covers off of him. He was only wearing some white briefs. He had a very impressive bulge between his legs. I gently put my hand on his crotch carefully rubbing the outline of his dick with my fingers. That wasn’t enough I had to see it and feel it. I carefully stretched his underwear down to just below his balls. His penis was twice as big as mine and wasn’t even hard. I don’t know what got into me that night but I just had to touch it. I wrapped my hand around his dick and gave it a little squeeze trying not waking him up. There I was with my sleeping cousin’s penis in my hand and I still wasn’t satisfied. I wanted to put it in my mouth and suck it, but what if he woke up I thought. I was trembling with excitement as I lowered my head and opened my mouth and took his cock inside. It was big I could only get half of it inside my mouth before I started to gag. I laid there sucking and licking his dick excited by how it felt and how it tasted. I loved the way it tasted, kind of salty and very sticky from my saliva. I felt his dick starting to harden in my mouth, Oh God, was he awake. I suddenly froze I tried not to make a sound. I had my cousin’s cock in my mouth trying not move and trying to be quite as possible I was so petrified that I didn’t even think about taking his cock out of my mouth. I soon heard him snoring again was he asleep or was he pretending to be. Either way I wasn’t thru sucking on him so took it as a green light. By now his cock was fully erect. WOW, was it big I could only get a little past the crown of his cock before I started to gag. I sucked his dick for another five minutes before my mouth was filled with warm, white, salty juices from his cock. I swallowed it all eagerly then put his dick back in his briefs and went back to bed.
The next day my cousin and I pretended like nothing happened continued with our daily routines.
A few days later we went to another part and got drunk again. This time when I went to bed I pulled my shorts down to my ankles after I got under the blankets and faced the wall and awaited my cousin to join me. About 20 minutes later I heard him stumble into the bedroom I closed my eyes and arched my back as he slipped into the bed. I heard him call my name I did not respond. I started making snoring sounds pretending to be asleep. I felt his hand brush against my ass. That’s when he realized that my ass was naked; he cautiously pulled the blankets back and uncovered me. He sat there a few moments admiring my ass. I then heard him get off the bed and then get back on. I guess he got off the bed to take his underwear off because as soon as he got back on he started rubbing his cock up and down the length of my ass. I then felt his hand pull my ass cheeks apart and started rubbing his huge cock between my asses. He put some kind of greasy substance on his hand and started rubbing my ass and then he gently slid one of his fingers inside me. He left his finger inside my ass for about five minutes then he slowly started moving it in and out of me. It felt great I was trembling in anticipation. With his finger still inside of me he then slipped another finger inside my ass, it hurt a bit as he started to fuck me with his fingers, sliding them all the way in then back out. About twenty minutes had passed when pulled his fingers out of me and the he started positioning himself behind me. He then gently pulled my ass cheeks apart with one hand and with his other hand he guided his huge cock inside my ass. It hurt so good, I could feel his big crown penetrate my ass, he gently pushed his head inside my ass and then he stopped. Good thing he stopped, it gave me chance to recover. I almost let out a scream when he penetrated me. After a few seconds he started pushing his cock inside me again, it felt so good I could feel every vein and bump on his big cock. When he was all the way in me I couldn’t help but started squeezing my ass hole around his huge shaft. He slowly fucked me for about ten minutes before I felt him explode deep inside me, his cum felt so hot. He took his dick out of me, put his briefs back on and went to sleep.
We have never spoken about this, although I often fantasize about him fucking me. I am twenty-five now and still have a body that resembles a woman’s, my ass has gotten bigger and still looks like an upside down heart because of my thin waist. I often get urges to suck on a man cock and have man fuck me in the ass. I don’t want a relationship with a man and I don’t want to fuck a man, I just want his cock.
Last year I wanted to get fucked so bad that I shaved my legs (what little hair I have) and bought some make-up and bought some tight fitting shorts that barely concealed my big butt. I looked great if I say so myself. I looked at myself in the mirror and my ass was just barely sticking out of the bottom of my short shorts. I could honestly say that if I saw myself a bar I would try to take me home and fuck me. Where was I going to go to find a horny heterosexual man that wants to fuck me? I decided to try a porno theater.
It was a Saturday night and I just arrived at the theater there were not many cars outside so I headed inside. I bought my ticket and as I turned around to walk into the theater I caught the man behind the counter checking out my ass, definitely a good sign. When I walked in the theater was very dark, I could hardly see. When my eyes adjusted to the darkness I saw there were about 15 men in the seats. I stood leaning against a petition that separated the entry door and the theater screen. I didn’t notice there were two men about 18 or 19 yrs old standing against the wall behind me. I was kind of nervous, but as the movie when on I got really turned on as I saw two hung black men fucking a girl with a big butt. I often fantasized about that being me getting fucked by two huge black cocks. As the night went on the two men behind would leave then come back, it appeared they were getting another beer. When they left the fifth time I decided to show a little bit more so I pulled my shorts up a little higher exposing most of my ass. My skin is pale so it was very visible in a dark theater. I had put on some baby oil on my ass before I left to the theater so my ass was gleaming in the dark. When the men returned one of them came and stood beside me. I dared not look at him, ten minutes had past when I felt his hand caressing my ass. He stood beside me feeling and squeezing my ass for a few minutes then he got behind me and pushed his crotch up against my ass. With out a word he bent me over the seat in front of me and pulled my shorts down and slid his big cock inside me, it was great finally I’m getting fucked. It had been so long I thought myself. His friend came over to where we were and took his cock out and started jacking off as the other guy fucked me. Suddenly the man fucking picked me up and with his cock still inside me swung me around so now I was facing his friend. The man in front of me started rubbing his big cock on my lips so I opened my mouth and started sucking it. The man behind me was fucking me hard he was thrusting his cock as hard as he could up my ass. I felt so nasty as he stated saying “do you like my dick in your ass” I could not reply as the man in front of was filling my mouth with his big dick. They fucked me like that for about 20 minutes then they traded places and fucked me till they both came inside me. Without saying a word they pulled up there pants and left the theater. I was deeply satisfied for the time being.
A year has past and now I’m looking for another adventure.

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beginner crossdressing

I am 20-year-old short gray hair about twenty pounds heavy but not fat, with a round big ass. I am seeking to give oral to completion for nothing in return.’
In my younger day, I was constantly searching to meet strangers for adult fun, to give them oral without the man having to give anything back in return. I had regularly posted advertisement to personal encounters of Craigslist, resulting in receiving several e-mails a week from men wanting to meet. I answered every e-mail asked them when they could they meet, where could we meet and when we met, what did they want to do. When they responded, with the necessary information, I reviewed their information then decided if I were willing to meet. E-mails were from local men or from men traveling and want to play when they were away from home.
I received one e-mail from a stranger in San Diego; his name was Ray. Ray was coming to my town for a few days on business, mentioning my advertisement posted on Craigslist. He wanted to meet me, so I could give him a blowjob. Ray and I exchanged a few e-mails and I agreed to meet him because he could host at his hotel room. In his e-mails, Ray asked a strange question, “Do you know any transvestites?” Ray mentioned he had a fantasy about meeting a chick with a dick. In my e-mail back to Ray, I told him that I had a fantasy about a Tranny topping me. I told Ray I would look around for what we both had erotic fantasies. I provided Ray my phone number should we need to speak about our threesome. The next-day Ray, my cell-phone rings and it was Ray.
First question after hello, Ray said, “Do you swallow or spit?”
I responded boastfully, “I like letting a man shoot off in my mouth and having him tell me to swallow his load.”
Ray continued, “Good; I am straight man, and not interested in sucking any cock. So you’ll do fine.” Ray continued his questions; he asked, “Did you find a chick with a dick yet?”
I responded, “No, not yet; I will check Craigslist today. You know that most she-males charge money. I am willing to split the cost with you.”
Ray scoffed, “No, not fine. I do not pay to get my rocks off. You need to find a chick with a dick to meet us, and one that does not charge. I want to see her sucking your cock; I take her from the rear. Then I want to see her cock fucking your ass.”
After Ray’s phone call, I started my search on Craigslist for a chick with a dick. I found several and sent them all an e-mail. The next day, I received an e-mail from Crystal, a thirty-five-year-old transvestite with silicone breasts. Crystal lived about thirty miles from the town I was living in. Crystal provided her phone number to call confirming our meeting arrangements. When I called her, it rang six times, and I wondered if I had the correct phone number. Finally, when someone answered the phone, I said, “Crystal, Roger.”
Crystal answered in a low, soft whisper, “Oh, hi sweetie; I’m Crystal, so nice of you to call.”
I did not want to catch her at a bad time, so I asked, “Crystal, is this a good time to talk?”
Crystal replied, “Sure Roger; I just got out of bed and fixing my first cup of coffee.”
The conversation was going as planned, I continued, “So, are you OK meeting Ray and me on Friday night?”
Crystal stretching her words, “Oh yes sweetie; I have two holes that loved to be filled.”
I was beginning to be excited about having a threesome with Ray and Crystal, but needed to check, not sure how to ask I blurted, “Crystal, I have to ask. Do you charge when you meet someone?”
Crystal replied, “Oh no sweetie; I am always free.”
I replied, “Great Crystal, Ray and I are not looking for a professional, just someone who likes to meet men and have fun.”
“I love to have fun, and with the two of you, there are more possibilities. I am versatile. Why don’t you two meet me at my place, where I have my things?” Crystal said with a playful sound in her voice. Crystal continues, “Now Ray is the straight guy who wants to fuck me and you are a bottom which likes to give oral? Crystal continues by asking, is it OK for me to top you?”
I responded, “Yes that sums it up, and I also like to give oral.”
The meeting was set for seven PM at Crystal’s house on Friday night. I sent Ray a text message giving him Crystal’s facts. ‘Thirty-five TV, 40D, seven inches cut, versatile.’ Crystal provided a photograph that showed that she had large silicone boobs and a male member, a chick with something extra. Ray was all excited about meeting Crystal. The plan to meet as threesome was set.
On the Thursday evening, Ray calls me saying, “Roger, bad news my meeting has been canceled. I will not be arriving until Monday.”
I said, “No problem Ray, I will reschedule.”
I called Crystal to update her on the change of Ray’s arrival date. She apologized, but she was going to be out of town on Monday and could not change her plans. I called Ray back and I told him, “Ray; Crystal will be out of town on Monday night. She cannot change her plans. Looks like it is going to have to be, you and I”
Ray, in an upset and loud voice, said, “Roger, you will have to find another, she-male.”
Taken aback from his outburst and demand, I said, “I have tried, there are none available. I did find one, but she wants two hundred dollars an hour.
Ray retorted, “I am not paying for anyone’s service; I want to meet a cock sucking she-male slut, or cross-dresser will do.”
I apologized for not being able to meet his needs, “I have looked on Squirt and on Craigslist, and I’m telling you on short notice, I can’t find someone.” I started to be perturbed with his demand and in frustration I said, “Look, what you want me to do, wear pantyhose for you?”
Ray paused, with a devilish sound in his voice he said, “Yeah, you do that, you dress up for me.”
I was jesting, was not inclined to play dress up for anyone, not even Ray. I tried to talk my way out of his demands, by offering an excuse, “What, are you kidding, right? I have never dressed, ever. You have to be crazy to want to see me in pantyhose. Ray, I don’t have any pantyhose to wear.”
Ray insisted, “Well, go out and buy some pantyhose. While you are at it, get a matching bra and panty set. Make it something sexy.”
I continued to offer every objection not to dress, but Ray continued to press the demand. Resigned by his persistence, I agreed, “Well all right; I will find pantyhose, panties, and a bra. I am not going to buy a wig and a dress, or wear makeup, OK.”
My agreement to play dress up for Ray excited him about our meeting. Ray urged me on by saying, “Yeah that will be fine; I want to feel nylon stockings rubbing on my legs.” Ray agreed I would wear pantyhose and anything else I could find on short notice. I would meet him at his hotel room Monday night at seven PM.
I went to Walmart that Saturday. Walking around the woman’s department, spying at the panties and bras’ sets from a distant, my heart was pounding. I felt self-conscious about the thought of buying womanÂ’s clothes. Someone from work or my church might see me with large woman garments when they know my wife is small. I knew that husband’s shop for their wives, so why would anyone notice or care what I was buying.
Embarrassed, I walked down the panty display, grabbed a red lace ruffle panty with matching bra. Next, I walk to the stockings and selected several pantyhose; I made sure they were large. I raced to the automatic checkout; I did want a cashier to remark what I was buying. Quickly, I left the store. Five minutes later, I could still feel my heart pounding. I had an Adrenalin rush caused by buying woman garments as directed by a stranger named Ray.
In my e-mails and chats with Ray, we talked about me giving him blowjob while I was dressed in pantyhose, panties and a bra. Ray called them sissy clothes. The date, time was set, and everything confirmed; I would wear the pantyhose, panties and bra. I would rub my nylon-clad legs against Ray’s legs, and Ray would get hard. I would perform fellatio for him, and we would both be happy.
Ray arrived on Monday and attended his business meeting. I got a call from him about six PM, Ray questioned, “Are you ready?”
I replied with an excited voice, “Sure, I’m ready to meet you and can be there at seven.”
Ray continued, “Do you have sissy things on now?”
I responded with sound of humiliation in my voice, “No; I was going to get dressed at your motel room.”
Ray shot back quickly, “No-good. I want you to arrive with your wear your sissy things.”
I tried to offer my objection by saying, “No way; I do not want anyone to know.”
Ray in a convincing voice, saying, “Who is to know, wear your stockings, panties and bra on, then your pants and shirt; no one will notice.” Ray says, “I want you to arrive with wearing your sissy things. No sissy things, I will cancel our meeting.”
I did not want to disappoint him, I reluctantly said, “OK I will. I will do as you ask. It should not take me long to get them things on.”
Now Ray ordered me, “When you arrive, the door will be open, you knock, and I will go into the bathroom, you enter and remove your shirt and pants. When I walk out I want to see you in pantyhose, panties and bra.”
Submissively, I responded, “Ok; I’ll be there at seven.”
I got naked and took the pantyhose out of the package. The package said they were large, but looked small. I looked if there was a front or back. I could not tell. I looked for instruction, there was none. The pantyhose were black and sheer. I asked myself, how do you wear pantyhose, one leg at a time? I had to roll up the leg, slide my foot into the tip, then pull and unroll the stocking to the knee. I did the same for the other leg, I stood, pulled on each side so the pantyhose and covered my butt to the waist. I smoothed out any wrinkles in the stockings; I looked at my stocking covered legs. I commented to myself; I had pleasurable and womanly shaped legs. I shaved my legs so to look more feminine for Ray.
I put the panties on first then the bra. Ouch, the Bra was unyielding. I bought a large, but the straps pressed into my skin restricting. The bra around my chest restricted my ability to take a deep breath. I covered up my sissy things with my pants, shirt and shoes. I drove to Ray’s hotel dressed in woman underwear and had the filling others watching. I prayed not to have an accident or pulled over by the police. You could not tell I was wearing pantyhose, panty, and a bra. Nevertheless, I was self-conscious about my sissy condition.
I did not want to be late, and arrived at Ray’s motel before the scheduled time. I sat in my car, feeling how smooth and silky the pantyhose were against my shaven legs. The bra was still tight and restricting my breathing, or maybe I was excited about being dressed.
At seven o’ clock, I arrived at Ray’s motel room door. I knocked on the door; I heard an answer, “Come in.” Pushing on the door, I found it unlocked. Once I entered the motel room, I closed the door behind me. As instructed, I took off my shirt, pants and shoes to reveal my male body wearing black sheer pantyhose, red ruffle panties and a red under wire bra. I do not have big breast, but the bra did giving the appearance that I had small breasts.
A stranger appears out of the bathroom with a towel wrapped roughly around his waist. He said, “Well helloooo, I am Ray.”
We shook hands; I replied and said, “Roger.”
I lifted my arms, and twirled, so he could see all of me. He sat on the bed and asked me to stand in front of him. The pantyhose were sheer and black, but you could see my moderate erection bulging off to one side. He undid the towel exposing his genitals. His cock was limp. He turned me around, so I was facing away from him. He pulled on my hips causing me to sit on his lap.
I was in the typical lap-dancing position; my butt was hovering above his crotch. Moving my butt in circles, I pretended to grind his package with my cheeks. I changed the pace. I switched to a revolving motion; I was simulating riding him in reverse cowgirl position. Looking back at Ray as I grinded against his body, I could see the grin on his face become a smile. Sitting for full-body contact, wiggling my bottom on his legs, and rocking back and forth on his male member caused Ray to be aroused. The contact between my pantyhose and his flesh did not take long to awaken his hardness between my legs.
I continued to rub my bottom on his erection while he felt my breasts and slipped his hands into the bra from the top to play with my nipples. He got my nipples erect; I got his limp member erect.
He told me to sprawl on the bed on my hands and knees facing him. I did as ordered. I saw his erection for the first time and could see a cut phallic about six inches. He stood in front of me, placed his hands on each side of my head, pulled my head forward and down, directed me to give him oral. I opened my mouth; accepted his hardness into my warm wet mouth. I heard him moan and tell me how that feels good. He kept his hands on my head moving his hips up into my mouth, using his hands to restrict my moving.
Ray used my mouth for his pleasure for a few minutes, he stops and ordered me to stand. He slid my panties down to my ankles. He turned me around, forced me onto the bed, so my knees were on the edge, my hands starched in front; I am in the doggy position. He rubs his cock along my crack and tries to rip the pantyhose, but no luck. Ray rips hole in the pantyhose at a location in line with my anus. I did not expect to receive anal intercourse that night; I was only hoping for oral.
As he rubbed his erection on my pantyhose, aroused, he grabbed my hips and dry humped me. Ray forced me on my elbows, pulled my hips up. He positioned himself with his cock aimed at the hole in my pantyhose. He slides his cock through the pantyhose and touches my rosebud. I have had been anal a few times, and I know I need to relax and let him do what he was going to do.
I needed to relax for his shaft and gland head to slip pass my anal sphincter muscle. I relaxed more with Ray being able to insert his erection halfway into my man-cunt. I was tight and there was no lube; I had to reach behind me and spread my cheeks. With a last push, he was all the way in. Ray started to thrust in deep then slowly withdrawal.
He grabbed my bra began to squeeze, pinching my nipple at the same time. I tighten on his member inside me, gave him pleasure. The speed picked up; the thrusts were deeper, and each time I cried a moan of pleasure. Ray held my hips, so I could not move, and he climaxed was way up inside me. Everything happened so fast that I did not realize Ray did not wear a condom.
I collapse on my side, Ray rolling with me, his manhood still inside me. We lie there for a few minutes, when his relaxed cock slipped out of my now dripping wet anus. He patted me on my butt and said I was hot in pantyhose. He started to dress, mentioning that he had nothing to eat. He told me to stay dressed. I went to the bathroom to go clean up. I kept the stocking on, put the clothes back on and wore the bra; I was dressed as a sissy .
I went into the kitchen to cook something, he gave me a pair of high heel shoes, to cook for him dressed like this.
to be continue…

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My first night as a Maid

This is a true story, involving me and my boyfriend. His account on here (WittleLion) has two stories uploaded, checkem out ^-^ http://stories.xnxx.com/profile586151/WittleLion

Secret Love

It happened my freshman year of high school, I was 16 years old. I was on craigslist looking to meet older men for hot encounters. That’s when I came across and ad entitled “daddy seeking son – m4m – 40 (my hotel room)”. I was turned on when I opened the ad and saw a picture of a fully erect 8” penis. The man posting the ad stated that he was getting a room for the weekend and looking for a young boy to join him for a hot kinky encounter. Lucky for me, the hotel he was going to stay at was just down the road from where I lived. So I emailed him back sating my stats, what I would like to do and that it would be my first time with a man. I also sent him a picture of me wearing my step moms lingerie stating that I loved crossdressing. Within a hour I got an email back from “daddy”, he said he loved my pic and would love to pop my cherry. After a few emails, we finally got a meeting set up for the upcoming Friday night. We agreed that he would leave an extra key to his room at the front desk, I would go up to his room, get dressed, get into bed and he would enter and get in with me. Now all I had to do was get through the next few days. I planned to get some of my step moms clothes; bra, panties, thigh high stockings, garter belt, high heels, and a short dress.
After what seemed like a lifetime, Friday morning arrived. That morning I faked being sick so I could get things ready while my step mom and dad was gone. Right on time my step mom left for work at 7:30 and my dad left for a weekend business trip out of town. Once I made sure the coast was clear, I hoped into action. First I got in the shower and shaved my body. Next I went into my parents bedroom to get try on something for the night. I picked out a matching bra and panty set; pink and black satin zebra pattern. I put them on and was instantly erect from the feeling of the satin panties against my clean shaven penis. Next I found a pair of black nylon thigh high stockings and a black garter belt. After putting them on I went to my step moms closet to pick out a dress. She had lots to choose from, but I found the perfect one. It was a metallic silver Jersey dress that came down to just above my knees. I put it on and admired myself in the mirror. After I was satisfied with how I looked, I took the clothes off and packed them in my bag. After that I went to my step moms side of the bed and opened her night stand. Lying in the drawer was a 7 inch long, 1.5 inch wide vibrator that looked like a real cock. My heart raced as I picked it. I also found a bottle of lube next to it. I crawled up onto my parents bed, I sat up and poured a nice layer of lube on the vibrator. With it lubed up, I laid back and set the toy at the entrance of my boi pussy. I took a deep breath as I slowly pushed it in. My heart raced faster the deeper in it went. When I was at a comfortable depth I turned it on. It felt great as it vibrated in me. The looser I got the more of it I was able to push in. With in minutes I was rock hard. It only took a few strokes I blew a huge load onto my hairless chest and onto my chin. I was breathing hard as I laid there, vibrator in me, licking my cum off my chin.
It was a lil’ after noon by the time I got cleaned up and put the toy back where it was. The plans for the night was to go to his hotel room at 6. So around 1 pm I called my step mom at work and told her I was “feeling better” and that I was gonna go to school.. At about 4 pm I grabbed my bag, got on my bike and headed for the hotel. Once there I called my step mom and said I was going to a friends house for the night. Finaly it was just before 6 pm. I walked up to the front desk and asked for the room key. The lady behind the counter said it was on the 7th floor, last door on the left. I thanked her and was on my way. As I stepped off the elevator my heart began to race. I walked slowly, checking over my shoulder although I didn’t know why. My eyes widened as I got to the room. The door was marked “Honeymoon Suite”, my “daddy” for the night went all out. I opened the door, he was gone, just as we planned. The room was lightly light from the candles on the tables, the hot tub was full and the jets were going. I went to the bathroom and got dressed for the second time that day. I gave myself a final once over in the mirror, turned off the bathroom light and crawled into the king size bed, facing away from the door. I laid there for what seemed like an eternity, waiting, hoping he would like me. Then the moment of truth, I heard the door open and shut. A few seconds later I felt him get in bed behind me.
“You look sexy baby” he said as he slid his hand across my waist and kissed the back of my neck. As he kissed I felt his hand come up and squeeze my nipples. Then slide down and rubbed my clitty.
“I’ve been thinking about you all week long daddy.” I said as I reached back and felt his hard cock. He was bigger in person.
“You ever kiss another man?” he asked as he continued to rub me.
“No”
“You want to?”
“Yes”
“Turn over baby”
He didn’t have to ask me twice. Here was my chance to do something Ive wanted to do for a long time. I rolled over to look him in his eyes. When I did, I was in for the biggest shock of my life. Laying in front of me, completely naked with a fully erect cock was my own dad.
“What the hell?! What are you doing here, and why are you dressed like that?!” my dad yelled as he jumped out of bed and threw his robe on. I couldn’t say anything. Here I was, dressed up as a girl, laying in bed in front of my own father. He walked over to the closet, pulled out another robe and told me to put it on. I did, and then just sat at the end of the bed, looking away from him and crying. He walked over and sat beside me. After want seemed like a life time we started to talk. I told him how I was curious about sex with a man and that I liked wearing women’s clothes and how it made me feel sexy. We talked for the next hour and finally came to the agreement that we were both sexually aroused by one another. He said he meant it when he said I looked sexy but wanted to see the whole outfit. I stood up, stripped the robe so my dad could see his “girl” all dressed up. Seeing me that way turned him on cuz the next thing I know he stood up, dropped his robe and he was fully erect again. He walked up to me, put his hands on my waist and said “this will be our lil secret.” With that he leaned forward and kissed me.
Hope you enjoyed reading this as much as I have writing this. There are more stories to come of me and my dad’s secret love affair. If you enjoyed it please comment. Please no rude comments, as this is my first time writing.

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Her girlfriend, my cousin

I guess it all started on a Saturday afternoon. My mothers bra was on top of the laundry pile. It caught my eye and I instantly became fascinated with it. I stole the bra and ran to my room to try it on. I remember the rush it gave me. I loved it and I decided to continue. I did everything I could to get my hands on more clothes. I stole bras, panties, pantyhose, slips and dresses from my mom. Swimsuits and bras from my cousins and grandma. I couldn’t get enough. I strained to look and feel more and more like a woman. I refused to be the typical person stuffing their bras with socks and tissue. It just didn’t look, but more importantly, feel like real breasts. So I got the bright idea to fill rubber gloves with water and use them as breasts. It worked for a long time until I learned what a breast form was. Then every cent of my pay checks were going to clothes and underwear. And that is where my story begins.
It was Thursday afternoon and my family had just left for my brothers baseball game somewhere south. I really didn’t care, the house was mine until Sunday. It wasn’t more than 2 minutes after they left the driveway that I was already in my room getting dressed. I had my breast forms glued to my chest, an expensive corset which was the pride and joy of my collection, with the attaching garters and nylons on. I continued to put my slip, and dress on completely oblivious to my surroundings. Unbeknownst to me my cousin had been recruited by my mother to check on me while they were away. She had let herself in with the key she had been given. She made he way down the stairs to my room where the music was playing and I obviously was, singing and dressing away. She turned the corner and we both let out a started yelp and of course I jumped to hide. There was no where to go, I was trapped. I stood there with my back to her trying to hide my shame.
“Trent? What are you doing.” she asked. Nervously keeping her distance from me.
“Nothing,” I replied nervously, “what the fuck are you doing here anyway?”
“Your mom asked me to come check on you, so I stopped by to see if you wanted to go get some dinner and you’re here dressed up like a girl. What are doing dressed up like that?” I turned around to face her. She had a mixture of emotions on her face. Im sure I had the same look on mine. I was blushing with embarrassment, but trying to hide it.
“I just like the way I look when I dress like a girl. I just… I want to be a girl,” I said hanging my head. For some reason Amanda always sympathized with me. I guess that’s why she was my favorite. We did a lot of things together aside from the usual thanksgiving and Christmas dinners. We hung out a lot, went to movies and had grown really close. And it had always been her that I had looked up to when I would dress up and play lady. It was here clothes that I had started my collection off with and I wanted to tell her so much but in that situation I figured the best thing to do was keep my mouth shut. She could I was being sincere. She moved closer to me and put her arm around me.
“Well maybe you could stay a boy a little while longer for me,” and then she did the one thing that surprised the hell out of me. She bent down and kissed me. I was shocked and instinctly pulled back.
“What are you doing?” I asked.
“I want to see what this is like. I know you have always wanted me and I’ve always wanted you too. So this seems like a better time than any doesn’t it?” she began fondling my breast with her hand as she bent in again for a another passionate kiss. Only this time I didn’t stop her. She stuck her tongue in to my mouth and we twisted and tangled. The grope session became a more furious and she and I began feeling each others breasts and rubbing each others bodies all over. I started to lift her sweater off so I could feel her big natural breasts. She took it eh rest of they way off with only a brief pause in the suck fest being created between out mouths. She wore a beautiful red satin bra over her huge 30DD breasts. Her skin was soft and silky and warm just the way I wished my skin was. But do to the hormone difference, all I could do was shave and lotion up. I unbuttoned her pants and she helped me shimmy them down her legs. The tiny red thong she was wearing was so hot on her I didn’t want her to take it off. She tore it off anyway. There she was, the only woman I admired enough to emulate, standing in front of me naked, kissing me and feeling up me fake female body. I was shaking with excitement and passion as she guided me over to the bed and lay me on my back. The pink silk slip I was wearing slid down around my waist when I bent my knees slightly and opened up my groin. The bulge of my penis was very obvious through the skimpy piece of cloth covering it. She maneuvered the garter and panty to free my penis and put it in her mouth. The warm and wet sensation of a beautiful girl softly sucking your penis was had me in a trance. I lost track of time as I lay on my back fondling my fake breasts with both hands. Thousands of images were running through my head imagining she was licking the swollen clitoris of my non-existent vagina. I longed to feel the deep penetrating power of a large penis enter me. I wanted it so bad.
She finished me off and rolled onto her back. I instinctively knew it was my turn. I got up and headed for her vagina. It was sopping wet when I got to it. I began by licking her swollen clit and tasting her juices. It was so sweet. I inserted a finger into her and began to stroke it back and forth. She began to squirm in ecstasy as I continued to singer fuck her. After a few moments of letting her wiggle I decided it was time to fuck her. I arched her legs and pulled her toward me. I gently pushed my penis into her. Enjoying every moment of it slowly sliding deeper and deeper into her. I reached my maximum depth in her. It was wonderful. But I still wondered what it felt like. I could only imagine. I was jealous of her. I started stroking in and out. Slowly at first but getting faster and faster. I reached the point of no return and spilled my cum all over deep inside her. I let out a deep sigh as I leaned forward and lay on top of her, still inside of her. The events of the day had exhausted me and I was tired as hell. I kissed her once more and she kissed me back. As we lay there together she whispered in my ear something I still remember. “I love you Trent. And if being a woman is what you want, I’ll do everything in my power to help you get there.” she kissed my neck and we fell asleep in each others arms. Girlfriend and cousin.
I’ll continue this and finish the story if I get a good review from this. Let me know.

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First Contact

I’ll be honest; I was in the Navy at this time. I know, I know, ha ha ha. That’s a log story, not about a sexual experience. I’m not attracted to men; I love a woman’s figure, all the way. If anyone has been to Virginia, you’ll believe this.
I was bored one night, and went to a bar just outside of Portsmouth, by the shipyards. I didn’t know anyone, so I sat at the bar, and just got a beer and a shot. After my second beer, and about two more shots, I was buzzing pretty good, and started to look around. There was a dirty blonde at the end of the bar still alone. She was talking to the bartender, and seemed a little upset. I figured he was family, or maybe a protective father figure. She noticed me looking and gave me a hollow smile. “Daddy,” noticed me, and raised an eyebrow. He shot her a “watch it” look, and came down to see if I need another drink. I asked the all too familiar, “What’s up with her? She family?”
“My niece, from Brazil.” Was all I got out of him. He gave me the, “Don’t fuck with her!” look. She was looking my way, with a nervous smile, s I decided to go talk to her.
“You know, a girl as pretty as you shouldn’t be sad. You should smile, and brighten up the world.” Corny line but I’m a guy, and I was drunk.
“Nice line, not too original, but nice.” She smiled. Her uncle was glaring at me, and she looked a little nervous under his glare. You could tell she was interested but very nervous with me as well. I just chalked that up to my appearance.
I’m not a big dude, but I’m fit, and strong. I’m what they call a snipe. I work in the hole, greasy and sweaty. I’m also on the Fire Party, so I have to be strong to hold that fuckin’ hose down. I also shave my head to hide my Ben Franklin hairline. I was bald at nineteen. I’ve been told that it looks intimidating.
“You can relax, I’m not gonna hurt you.” I smiled.
“Only my feelings.” She whispered, with a nervous smile. The smile turned to a frown. “I’m not like other girls. My father, whom I haven’t seen since I was eleven, told me to get the fuck out of his face, and never come back. Every boyfriend I’ve had since I came back to the states, have dumped me, or beat the shit out of me. So please understand, I think you’re very cute, and sweet, but I have reasons to be nervous. Like I said, I’m not your typical girl.”
“Well, as long as it’s not like a Springer thing.” I smirked at her. She winced and looked away. “What’d I say?”
“You wouldn’t understand.” She started to get up.
“Wait, I’m sorry. What ever it is, I’m sure it’s not that bad.”
“You’d be surprised.”
It was getting late, so I asked if she wanted to get some coffee another time. She smiled, and replied, “Yeah, that’d be nice. I’ll be in here the next three nights, working for my uncle. I get off at 3am, we could go then.”
“Sounds good, I’ll see you day after tomorrow. I’ve got duty tomorrow.”
“I’ll see you then. My name’s Alex, by the way. What’s your’s?”
“I’m Ryan. I’ll see you then.”
She got up, and I could see her frame as she walked away. She had strong thighs, and a beautiful Latin ass that bounced when she walked. A thin waist that tapered in like an hourglass. She wore sexy “Fuck Me” boots, and had nice medium firm tits, that bounced with every step. I was in love.
The whole next day, was torture. I convinced my LPO (boss) to let me have the next day off, so I might be able to get lucky. I couldn’t wait to see Alex again.
I showed up at 8pm to see her. She was behind the bar getting some fat slob a beer. I walked up and said, “Hey, can we get some service here for Christ’s sake?”
She smiled at me and brought me a beer. “This is from the lady at the end of the bar.” She smirked. I looked down and saw what had to be the greasiest fat assed, Sea Donkey, I’ve seen in a while. I shivered, and took a long drink.
“Thanks!” I tipped the bottle at her, and got her attention. “Thanks!” I said again, and winked at her. She gave ma a puzzled smile, and waved, then turned back to the bar. “Yep, I’m gettin’ lucky tonight.” I took another drink, as she slapped my shoulder.
“You’re an ass!” She smiled.
“Hey, I was being thankful. I’m might be able to get with that.”
“I’m not woman enough for you, am I?”
“If I can’t get with her, you’ll be next in line baby.” I looked at her tanned face and pretty brown eyes. We both just stared for a moment. Until her uncle thumped the bar.
“Alex! You gonna work tonight girl?” He gave me his tough uncle look, and turned away.
“Sorry, I gotta go. I’ll talk to you in a few hours?
“I’ll be here. I’ll probably be drunk, but I’ll be here.”
She gave me a kiss and ran her hand down my chest before turning away. Instant wood. I loved watching her ass sway.
By the end of the night, I was feeling pretty good. She came over to me and sat on my lap. “How ya feelin’ babe?”
“Great, Just waitin’ on you girl.”
“I’m getting off in half an hour, you gonna be okay then?”
“Mind if I watch? I slurred. I wasn’t hammered, but I knew if I laid it on thick, I could get away with more.
“If you’re a good boy. Now, I’ll get you some coffee.” She kissed my cheek and brought me a cup of coffee, which I drank straight to get my senses back. She brought me a second cup and one for her when she came back. She sat down next to me and asked if I wanted to go back to her place. “I’ll drive.” She said quickly.
“Sure, I’m game. Just don’t bring Sunshine.” I pointed at her uncle wiping down the bar.
“Yeah, we kinda need to get soon, so he doesn’t see you leave with me.”
“Well, let’s get then.” I said, in my thickest redneck accent. We got up and headed for the door. I waited till we were outside to put my arm round her, and she guided me to her car.
“I live two blocks up, so you can get you car no problem when it’s daylight. It’s not safe to walk this in the dark.” We got into her car and drove the quick trip to her apartment. It was a bit of a dive, but the inside was clean. I sat on the couch and she got us both a beer.
When she sat down I asked, “What, are you trying to take advantage of me. I just started to sober up.”
“I like you Ryan, but I can’t do much with you right now. It’s my time, but I can do other things.” She kissed me, and put her hand on my cock. I was instantly hard. She stroked it through my pants, and licked my ear, biting my earlobe. I put my hand on her back and put the beer down, so I could play with her tits. They were firm and soft. Might have been implants, but they still felt good. I pinched a nipple and she moaned in my mouth. I moved my hand to her ass and squeezed it.
She pulled away and said, “Remember what I said. No further, it’s gross down there. Please?” The last word was almost begging, so I said okay. Man, some girls are weird about that.
I moved up, and started playing with her tits again. She took off her shirt and bra, and I sucked one into my mouth. I kissed her stomach, and noticed the sexy bellybutton ring; it had a jewel on it. I tickled it with my tongue, and licked my way back up to her tits. She took off her shoes and pushed me back on the couch. She pulled off her socks and told me to take my shirt off. I did as I was told and she put her soft feet on my chest. Rubbing them into my chest hair she pinched my nipples with her toes. I rubbed my calloused hands on her soft feet and kissed the ball of her foot. She pulled them back and rubbed them on my crotch, stroking my cock through my pants. I started to unzip my fly, but she stopped me. “I’ll do that.” She smiled as she used her toes to hold the top and the other foot to unzip me. She had some talent with monkey feet. She definitely liked to play. She fished one foot in to find my cock. “Um, soft boxers.” She purred. She got her toes through the front of my boxers, and used the other foot to fish my cock out. I’ve never ad a foot job before. I liked it so far. She ran her feet up and down on the shaft of my cock. Her long skinny toes look hot as hell rapped around me, and the little toe ring matched her gold nail polish. It felt wonderful, I just watched her fee and would look up to see her smiling, intently looking it her job at hand. My cock was throbbing, and the head was bright red, my veins were popping out. I was ready to come.
“Your gonna get a mess on your pretty feet, if you don’t watch out.” I breathed heavily.
“Hold that thought baby.” She smiled, and got on her knees in front of me. She took my cock into her hand. Looking up at me, she ran her tongue up the shaft, breathing hot wet breath on me. I felt my ass tighten as the shiver erupted through me. My eyes rolled back into my head as she rapped her whole mouth round me and sucked me into her hot mouth. It was so hot! I could feel my balls tightening, and my cock ached to cum. I growled and grabbed her head. When I thrust into her mouth, she sucked even harder. She wanted to taste me. I forced into her mouth one last time and filled her throat with my cum. She jacked and sucked me dry, then showed it to me. She smiled, open mouthed and played with my cum before swallowing it. I looked down at her, wearing nothing but her jeans. Beautiful. She got up as I put my cock away, and sat on my lap, resting her tits on my chest. I squeezed her ass and cupped her chin. We kissed and I moved a hand to her thigh. I caressed her leg as we kissed deeply. Moving up, I noticed something wasn’t right. She pulled away instantly, as I grabbed her crotch. “That’s not a fuckin’ pad!” I yelled as I threw her to the floor. “What the fuck! You’re a fuckin’ dude!” I stood over her, it, looking down in rage.
“Please, don’t hurt me!” She cried, tears welling up in her eyes. She covered her head with her arms, whimpering. My heart sank, and I felt sick to my stomach. I was so confused. I wanted to be angry, but I felt ashamed. I towered over it, no her. She was a girl. Maybe she wasn’t totally female, but she was all girl. I felt like a bully, a bastard who fed on people’s weakness. She had given me so much pleasure, and I just attacked her. “I’m sorry Ryan! Don’t hurt me, please!” She had crawled to a corner and curled into a fetal position, rocking back and forth.
“No.” I breathed shamefully. “I’m sorry. I won’t hurt you. I couldn’t hurt you. I had no right. Please forgive me. Please, get up. I’m the bastard here. I’ll leave now, Don’t be afraid of me. I’m sorry.” I turned, and picked up my shirt.
“You’re not going to hurt me? They always hurt me when they find out.” She lowered her arms and looked up at me with those beautiful brown eyes, red and wet with tears. My heart sank, I wanted to puke. I wanted to beat my head against a wall, to hurt myself like I’d hurt her.
“I’ll never hurt you. I’m sorry Alex. I’ll leave now.”
“Please, don’t go!” She jumped up. “Don’t go! You’re not mad?”
“You should be the one mad, not me. Don’t you want me to leave?”
“Not if you don’t want to. I’m confused, you’re not mad. I have a dick.”
“Yes, you do. Yes, I’m a little confused to. I don’t know what to do at this point. I’m not gay, but I’m attracted to you. I’m curious about you. Hell, I don’t even know what to call you!” She frowned and her lip quivered with that. “I’m sorry. That was uncalled for. You are definitely a girl.”
“I can be what ever you want me to be. If you’ll let me, if you’ll try to let me.” She smiled nervously.
“It’ll take some getting used to. Are you going to finish the transformation?”
“I was, but I have to save the money up first. I will return to Brazil for that. America has too much red tape. But it will be a while. Are you willing to work with me till then?” She put her hand on my shoulder, timidly caressing me. “It could be up to another year.”
“I’ll try, but you have to be patient with me to. You’re not going public with this are you?”
“God no! You’re the first who didn’t beat the hell out of me, when you found out. I’ve lived in four states because of this. I can’t go public.”
“How can I make it up to you? I’m sorry I acted like such a shit.”
“First, you could stay. Second, you could talk to me like I’m you’re girl and not some freak show. I want to be you’re girl.” I put my arms around her and kissed her. I wiped away he tears and carried her back to the couch.
“You wanna get naked, and let me get used to this?” I whispered. She smiled and undid her pants. I helped her pull them off and the thong she was wearing under them. Her cock was dangling in front of me. It was a bit strange to look at, but I wasn’t freaked out anymore. I reached out and cupped her balls. She gasped and started to pull away. “Are you okay? Did I go too far?” I asked.
She grinned and sat back on my lap. She took my hand and put it back between her legs. “I’m sorry baby, I’m not used to that.”
“Does it work? I mean can you get hard?” I asked nervously
“I don’t have the money for estrogen treatments, so yes. My breasts are implants, and the rest of me has always been girly. I was picked on in school for it, and I always wondered why I was born a boy. Do you want to see it hard?” She looked into my eyes hopefully. I could feel her getting thicker in my hand. She shaved everything down there. I stroked it like I stroke mine, and she moaned into my neck as she nuzzled under my chin.
“Lay down.” I pushed her down and climbed between her thighs like I was going to eat her out. I rubbed her cock on my chin and cheek. It was getting harder and was not a bad length. Not as thick as me, but about as long. I felt a little relief at that. If it was going to make it in my ass eventually, at least it wasn’t real thick. I ran my tongue up the shaft and cupped her balls. I didn’t know how to suck cock, so I tried to do what I would want. I stroked the shaft and bobbed my head up and down, sucking it hard. She was moaning and rubbing her feet on my back.
“I’m gonna cum, please stop.” I did as I was told since I wasn’t ready for that just yet. I kept stroking her though. “Will you fuck me? I want you to fuck me. I want to cum with your cock in my as.” I put my cock in her face.
“You might want to get it wet first” I smiled.
“There’s KY jelly in the drawer, for my ass.” She said a she took my cock in her mouth. “Think you can find it while I do this?” She said with the head between her lips. I giggled and she did to as I fished hastily in the drawer for the lube. I held it up like a sword and pulled the cap off. She spread her legs and brought them back to her chest, exposing her asshole. She spread her cheeks and sucked my cock hard. I forced myself to concentrate so I could apply the lube. I could see her smiling devilishly as I tried to do my deed. I put the tip to her asshole and squeezed some into her ass, and smeared some on the opening. I pulled my cock from her mouth and got between her legs.
“Spread it baby. Show me you want me inside you.” She spread her cheeks and raised her feet back to her head. I put some jelly on the tip of my cock. I put the head at the opening of her brown eye. I pushed the head into her ass. She closed her eyes and whimpered. “Am I hurting you?” I stopped and leaned in.
“Just a little. Go slow at first, but don’t stop. I want you to fuck me, not baby me. It hurts, but I like it. Fuck me, fuck my ass baby.” She spread her legs and stroked her cock. I pushed harder and slid my cock all the way in to the balls. I grabbed her ankles and started to fuck her faster. She rubbed her cock faster and moaned. I could feel her ass squeezing my cock. She was rocking up and down as I fucked her ass, and she started to shoot her cum all over her chest. I let go and rubbed it into her tits, and fucked her faster as I started to cum myself. “Cum in my ass! I want you to cum in me!” I let go and filled her full of my cum. Her ass was squishy and wet with my cum. I left it in her and leaned forward kissing her lips. She lifted her leg up and rolled to her side, pressing against me to hold me in. I laid behind her and held her close as I slowly fucked her ass for a while rubbing her belly and kissing her neck. We slowly drifted off to sleep.
I moved into her apartment the next day and we lived together for 8 months as a couple. I let her fuck me once in a while, but most of the time Alex wanted to be the girl. She moved back to Brazil and we kept in touch for a while, but she eventually stopped writing back. I wasn’t happy about that, but I got over it, and went on with my life. I do think about her a lot, and wish she would’ve came back to me. It goes without saying that I haven’t found a girl like her again.

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BED AND BREAKFAST

*********************************************Bed & Breakfast ******************************
my wife and I just came back from upstate New York and Vermont. We
stayed at 5 different B&B’s and one in peticular was a fantastic time
I will never forget.
We were in the VIP suite and the owners were in thier 30’s and
both of them were super HOT!
My wife was soaking in the jacuzzi then shaving, showering makeup,
etc,etc, she said to give her a hour and a half then she will come
out and join my by the fireplace.
So I got undressed and put on a pair of pantyhose, as i just pulled
them up, the door opened and it was the woman asking me what time we
wanted breakfast….I froze as did she starring the whole time at me
standing there in my pantyhose and nothing else. she then closed the
door. I waited a few minutes then I put a pair of sweats on and went
out to the living room where her and her husband were talking. I said
i was sorry and she said she was sorry for walking in without
knocking. I noticed her husband starring at my hosed feet and I
blushed. She then said my husband loves it when I wear stockings she
then got up and walked over to me and gave me a deep kiss.I got hard
instantly as we made out her husband came over and pulled down my
sweats.
I was standing there in my hose and a huge hard on as her husband
was rubbing my hosed ass she was rubbing my cock and kissing me. then
she turned me around and he dropped to his knees and started sucking
and licking me thru my pantyhose.she got behind me and pulled down my
hose and fed it to her husbands wet mouth. He started sucking me and
I came very quickly.He swallowed every drop.
He then dropped his shorts and out popped a 7 or 8 inch hard cock
i dropped down and sucked him and his wife joined me. he then bent me
over the sofa and fucked my hosed ass. He never entered me but I
guess the feel of the nylon against his cock got him turned on, he
let loose a huge load of cum all over my ass. I got up gave her a
deep kiss bent down and gave his cock a little suck, then went back
to my room. I took off my cum drenched pantyhose cleaned up and a few
minutes later my wife walked out of the bathroom suite. We had a nice
night in front of the fireplace, as I was thinking about what had
just happened!………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………………….

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What I wanted… Part 2

I started by lighting some candles, mostly jasmine but some were unscented. After lighting the candles I turned off the lights. As I walked over to the bed, Bryan was watching me the whole time. When I got to the side of the bed, I took my shirt off making sure he got a good look at my breasts. I then laid down and unhooked my bra so he could have full access to my back. Bryan then asked “Could you take your pants off? I could massage your whole body that way”. I am sure he meant it another way, but I wasn’t caring at that point. I was too relaxed being Ashley.
I raised my hips up in the air as Bryan slid my jeans off. Peeled them off is more like it, but he had no trouble. He then took my socks off. Massaging my feet and making sure I was in complete heaven. Bryan took his time, massaging every little muscle, every body part. As he was moving up my body from toe to head he got a little friendly with my butt. Truthfully I didn’t care, but the good girl in me told him to stop playing around.
Moving to my lower back he straddled me. Putting his legs on both sides of me sent chills up my spine and gave me goose bumps all over. I couldn’t believe it, Ashley had a real man on top of her taking care of her like a real woman. He slowly worked my lower back. As he moved to my shoulder blades he moved my bra straps off my shoulders and down my arms. His hands were firm yet gentle. After my arms he moved to my neck, which felt better than everything else.
As he was massaging my neck I felt him leaning down. I couldn’t figure out what he was doing untill… *GASP*. He was kissing my back while rubbing my neck, oh that just sent electricity through me. Finishing my neck he gave me a kiss on my cheek and laid down beside me. I turned my head to look at him, still fully clothed he laid there just smiling. I wasn’t sure what to do next, I just laid there and stared at him.
He leaned over to say something, but I interupted his words with a very deep loving kiss. Suddenly I thought I had made the wrong move, he wasn’t kissing me back. I started to panic thinking “what have I done”, but then he kissed me back and not only kissed me but french kissed me. Oh his tongue drove me wild, I forced back into him as we started to tumble on the sheets. I made a move and took his shirt off, all while holding our deep kiss. Oh his body was rock hard, abs of hard man flesh.
Since I was just down to my g-string I decided to even the odds a little bit. I threw him on his back and started undoing the button and zipper to his jeans. His relaxed fit wranglers slid off his legs, revealing a set of M&M boxers. At least his chocolate will melt in my mouth and not in my hand. After giggling for a second I started to peel his boxers off, slowly but surely they revealed 7″ of thick manhood. I gazed in amazement for a split second before I caught myself.
I started stroking it, thick and long it was. I wanted it all, oraly, analy, I didn’t care I just wanted it. I started licking his head with my tongue. First just one or two licks teasing him with every touch. Then I circled his head letting him feel my warm juices from my mouth. I took his head into my mouth after that. Just his head for a while, getting used to it. The more I bobbed up and down the fruther I was able to take him. First 3 inches, then 5, almost 6, but what I was doing was driving him mad. Finally he couldn’t take it anymore, he grabbed my head and shocked me. He forced it all the way in my mouth and down my throat. He was going in and out of my throat, as fast as he could untill he held himself against me. Grunting and shuttering he orgasmed, all down the back of my throat. He came, he came all in my throat
As he started to pull out I made sure he was clean, I licked his head and stroked it a few times cleaning out the chamber. After I finished cleaning I layed back on the bed, still horney and ready to go. I still had the salty cum taste in my mouth when he came over too me. He kissed me once and said “turn on your stomach”. My body wiggled with energy, I wasn’t sure what he was going to do… or try to do. He first layed on me, putting his still fat dick inbetween my butt cheeks. Oh it felt so good to have a man behind me like that.
He started to kiss me on the neck again, then he proceeded down between my shoulder blades, then down to my lower back… by this time I knew. He kissed both my butt cheeks and then proceeded to take my g-string off with his teeth. After sliding it off my feet, he proceeded back up to my butt where he would make himself known. He took a deep breath and sent a cool breeze of air around my hole. It made me pucker and tighten up, but I am sure thats what he wanted.
He told me to raise my butt, so I did as told. He came up rather quickly grabbing my thighs and forcing himself near me. His warm tongue clipping the outside of my hole. I couldn’t believe that this was happeing, My first tme with a real man and this was going to be my cherry popping too. My first time with a man, My virgin hole about to be violated. Now hes fluttering his tongue at my hole. I am so wet right now and he is only making me more wet. After teasing me for what seemed like an hour, he pushed his tongue into me making me feel his warmth inside.
With his tongue now inside me I am panting away, feeling every lick, flutter, and move of his tongue. Whether it was out of lust or love I finally said it… “Bryan… Bryan… put it in me”. I wanted it so bad, so bad i could taste it again inside my mouth. “Ok Ashley get on your stomach” Bryan panted. Bryan then asked “Do you have any lube?”. “Yes” I said “Its in the top of my dresser”. It was KY my favorite and personally it felt better than any others.
Bryan got the lube and put it on himself. He layed himself on top of me trying to get a easy angle. When he got to my hole I said “Bryan?”, “Yes” he replied, “Do me, do me like a REAL woman” I begged. Bryan needed no more, he put his head up to my hole and pushed gently. As wet as I was, it was still alot of work for him to slide in. Bryan was pushing in while I was trying to wiggle my hips to help, I must have gotten a good position because he slid in deep. More than what I wanted for the first time.
It hurt some but also felt good. Bryan pulled out till just his head was in, and started to re work it. In and out, In and out, slowly he pleasured my little hole. Before too much longer we were banging away, He was pounding me harder than ever and I was loving every minute of it. I started to scream, it felt so good that I just wanted to yell out. In the middle of everything I started to feel something in my gut. Yes part of it was his member, but it was something else, something bigger. “Bryan” I yelled, “yes” he panted back, “I’m feeling strange inside, like funny strange” He seemed to slow his pace a little when I said this. The feeling went away when he slowed down so I said “Forget it, just go faster”. With that Bryan took off in a flurry of pumps, each one faster than the last. My funny feeling came back, only this time I didn’t let Bryan know… I raised my butt up in the air to really feel him inside me. Still pounding away at me, Harder and harder.
Finally the feeling came rushing back, when it did I got up on all fours. Bryan was screwing me like his bitch in heat. Bryan kept his pace as I screamed “More MORE MORRE!!!”. I couldn’t keep the feeling in any longer, I couldn’t hold it back. “OH GOD BRYAN” I screamed “CUM INSIDE ME PLEASE CUM INSIDE ME!!!”. He must have been close because he released a HUGE load inside of me. As his load was releasing my hole clinched, and I jerked back on Bryans cock sending him even deeper into me. I started to jerk and spazam. My body releasing from my first ever orgasm like that. He held me up until I was done with my orgasm, then we fell together. Laying beside each other, his arms around me.
I fell asleep right after that, I woke up the next morning to a empty bed. But a note was on the pillow it simply said “To the woman of my dreams” it also had his phone number on there. I called it the next weekend, and I am sure you can imagine what happened.

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Forced To Be Female Part 6

Lockup. I was brought to dc (disciplinary confinement). I was put in a small cell by myself. I was there a week before anyone besides the other locked up inmates even spoke to me. I was transported wearing shackles in front of a disciplinary team. I was found guilty and scheduled to be sent to Raiford Prison in Stark Florida. This is the worst prison in the Florida system. I figured that I only had a short few weeks, maybe a month to live. The next week, I was brought to see one of the guidance counselors. I gave him a glazed over version of my story and I was told that I had maimed Thye for life. He would have scars on his face as long as he lived. I thought to myself that I would have scars the rest of my life also, because of him. Three days went by and I was brought out to speak to a guy from a well known human rights group that I won’t say the name of to protect my privacy. Anyway I spoke with him and gave him the same glazed over version of my story that I gave to the guidance counselor. The next day I was brought out to see a woman from the same group. She sat me down and told me she wanted to talk to me. She said that the reason she was there was because they believe it would be easier for me to tell my story to her than a man. I told her that I would tell her my story minus the names of the people who were involved. It took 2 weeks for me to tell her everything in detail. She was taking notes and wanted all the details that I could remember. During this time she arranged testing for Aids and other STD’s. Luckily or should I say miraculously everything came back negative. It was hard to say goodbye to her on the last day. She told me that after hearing my story they had my transfer reclassified to Cross City Correctional Institution. She said that it was a much mellower institution than both Sumter and Raiford and wished me luck.
(Before I continue here, I have some additional information. I meet a guy named Tiffany. Tiffany was a preop transsexual. I refer to Tiffany as she, not only because referring to her as female is was what he would want, but because I believe him when he told me he was a female stuck in a male’s body. Tiffany was 5’1” 103lb black male. Everything about him, from his nails, face, eyes, body shape, skin and manner was female. The only thing male about him was his plumbing. I wasn’t able to stay in touch with Tiffany after he got out, but I firmly believe that if he was able to get the operation, he could easily make a living as a female model.)
The next week I transferred out. I was hoping this would change my situation and I could have a semblance of control. As soon as I was brought to my new cell (two person cells), I started to look for a queen, for I knew that it was just a matter of time before everyone would know I was fucking at Sumter and I hoped I could get some advice from one of the queens. I met this guy who’s nickname was Tiffany. He/She was a girl in every way except sexual organs. I have never till this day seen a guy who looked so much like a beautiful black woman as Tiffany did. I asked her if she could give me some advice about Cross City and she agreed. She was in the same dorm as I and told me to come to her room after supper count. I met her there and I told her my circumstances. I told her what I had been through at Sumter and she was horrified. She told me not to worry about anything. She asked me if I wanted to room with her and I agreed.
It took about a week before we could make the arrangements (pay a guard) and I was moved to her cell. I got a job working in the silkscreen shop at PRIDE. Prison Rehabilitative Industries Diversified Enterprises. The first day after work, Tiffany introduced me to a guy nicknamed Apache. He was a big black guy who supposedly had a mix of Indian in him, but I couldn’t tell. Tiffany told me that I would need to pay Apache weekly for protection and occasionally give him a little sex and I could either live in peace or turn tricks to make my own money. I was instantly skeptical. I said let me guess, I need to service him until I can pay him, right? She told me that I needed to get clear on something. She said that she would take care of everything, she would pay for everything and the only thing I needed to remember is that I owe her.
Later that night she was putting together what she called a business plan. She told me that I would have to turn 5 tricks a week to pay for protection and live comfortably. She was telling me that I would need someone to do my laundry and sewing, I would need new panties, makeup and meals. I said don’t we get meals at the chow hall and she replied yes if you want to eat that shit. She said she had her own cook, a guy who works in the kitchen. He fixes meals and we can eat them here. I was impressed with her situation. All of her pants were tailored to her ass and legs, she had real silky panties, she taped herself with surgical tape (not duct tape), she had perfume, real makeup and a stash of pot. I told her how nice everything she had was and she told me that in a couple of days I would have the same. Again she said she would pay for it.
I believe that looking back at Tiffany, I can understand why now I have a thing for femdom and transvestites. She made me service her, not how I thought it would be. Our first encounter she tied me face down to the bed. She put her cock in my mouth and made me suck her incredible 8inch cock. She turned around and told me to lick her pussy (her ass). I was incredibly turned on, but she told me if I was servicing her, I would be taped and not get a hard on. She said I owed her, she didn’t owe me. I was in pain because I wanted to fuck that beautiful ass. I wanted to treat her like a woman and fuck her hard. She moved to my ass and started to finger it. First 1 finger then spoke to me in that husky feminine voice and said relax. I want to play. I did as I was told and she slipped another finger in my ass. She had small hands and fingers, so this wasn’t so hard to do. When she put 3 fingers in and spread them it became more difficult. Again she kissed the back on my neck and all the way to my ass and said relax. I again relaxed and she slipped 4 fingers in and spread them. I started to squeeze back and she just left it there and told me to relax. After what seemed like hours she could feel me relaxing and she slipped the 5th finger in. At this point I figured I was as relaxed as I could get, but she patiently waited and kissed my ass until she felt my ass muscles relax again. She started to slowly make a fist and I was thinking I was going to tear, she moved her fist in and out. After about a minute of this she released her fist and pulled her hand out. I sighed a relief and then she pushed her cock inside me and fucked me extremely slow, kissing and lightly biting my neck and back. When it was time for her to get off she got off me and stroked her cock in my face until she blew in on my face and tongue. She then moved back behind me and put 3 fingers back in my ass, she felt around until she found my prostate. She started to caress it I guess you would call it and I was ready to jump out my skin, and all of a sudden I started to cum. I was so fuckin amazed and blown away she began to giggle. She said you really don’t know anything do you. I was blushing when she untied my hands and feet. I cleaned up while she redressed herself.
I said what did you do? She replied that she had got me off and now I owe her even more. Don’t expect to get that all the time. Remember you owe me, not the other way around. Over the next week she dressed me the way she wanted, always trying to make me as feminine as her. This obviously wasn’t possible. She set up my times with Apache, she set up my customers(which was only two), she made me wait on her, shave her, wash her in the shower and made me have sex with her when she wanted. I thought or hoped that I would get to fuck her, but she never let me. Other than Apache I never saw anyone fuck her, but everyone wanted to. We were walking across the compound one day and she told me that she rarely lets anyone fuck her. She says she gets off on the desire. She said, don’t you feel it? I asked her what she meant and she told me to pay attention to my surroundings. Walk over to the basket ball court, by yourself stay there for oh let’s say 20 minutes come back and find me and tell me what you see and feel. Pay attention to how everyone looks at you and talks to you. It is a rush. I wasn’t sure what she was talking about but I did as she told me to do.
I walked to the basketball court and watched while everyone’s head turned to watch me. I found myself walking with more of a sway, like Tiffany walked. I went to the bleachers and sat down to watch the game in progress, and with a couple of minutes all the guys had moved over to sit with me. First one, then another until all of them moved over to sit with me. They started talking to me, first asking questions about me, but I could feel it, they were hitting on me as if I were a woman. I wasn’t experience with this and I could tell that soon the conversation was going to go in an area I didn’t want them to take it, so I jumped down and told them I had to go. They watched me intently as I jogged across the field, even the basketball players had stopped to watch me. I could tell they were probably saying obscene things about me, but I thought I was experiencing what Tiffany was hinting around to.
I found Tiffany back in our cell and told her what I had experienced. She said it was just part of it. She asked me why I waited on her hand and foot. She said if Mike was asking you to do all these things you would be upset, but you seem to do them for me without any quarrel. What is the difference? I said that I owed her. She smiled and said that I did owe her, but as far as I knew I owed Mike also. I thought about it and said that I didn’t mind doing things for her, it is not the same. She laughed and said that she dresses me up, makes me wait on her, give her back rubs, suck her dick, lick her ass, take her hand and dick up my ass. I think I probably treat you as bad or even worse than Mike did. I tell you who to fuck, when to fuck them, who to pay protection to, what to wear, how to wear it, when to be here and when to be somewhere else. I totally run your life, but you seem happy to let me. I told her I don’t know why I do this, you treat me better than Mike did. She said it is desire, you and most everyone here on this compound desires me. She said that most women have this same power, but not all of them know it. The ones that do know it, don’t know how much power they have. Women are brought up being desired by men, so most of them don’t even realize it is a power. A guy would be happy to have more than one girl desire him, he would think he is king. A halfway decent looking woman has almost half the population desiring them and they don’t see it as a power. It is just the way it is. You have this power also, she said. You don’t know you do, but you do. You need to refine it, but you have it in abundance. Most of these guys would do anything for you, if they thought they could have you. The line to walk is to never promise more than you are willing to give. That is a very fine line. I give just enough to let people know I give, but when I give, I always get the better part of the bargain. Don’t worry, she said. I will teach you. It will be a long time before I decide that you don’t owe me anymore and in that time I will teach you.
She started teaching me the next day. We are going to the chow hall she stated the next morning. I asked her why and she replied that I needed to learn how to handle myself in public. She said first we need to put some makeup on you. She said you are white so you have to be careful how much you use. The trick is she said is to use enough so it brings out the highlight in your face, but not look like a whore. When we were done applying the makeup, you could tell I was wearing it, but just barely. My eyes looked more pronounced but not slutty. Walking to the chow hall she told me how to walk, she saw that I was trying too hard. She walked behind me until she thought I was close to having it right. Practice that walk, she said, Soon you won’t even realize you’re walking like that and it will look natural.
She returned to my side and held my hand as we walked. I felt a little self conscious holding her hand and walking across the compound and she noticed. She said that this heightens the desire everyone will have for you. She says that most guys have a fantasy of being with two women. When they see you holding my hand it will start fantasies in their heads. Keep an eye on everyone as we walk, watch how many conversations turn to us. When we sat at our table I figured we would be surrounded with guys, but we only had a few even talk to us. No one sat with us, but everyone was looking at us. She reached across the table and would squeeze my hand occasionally and the attention we would receive was amazing. It was like everything she did was calculated.
Later that afternoon after work we met back at our cell. She had a guy she introduced me to. She told me that he was a tailor in his previous life and he was going to take my measurements. I said ok and she told him to lose the back pockets on all my pants. She told me to turn around and she grabbed the material on my pants that was touching my ass. She told the guy to look how my ass is round but petite. We would need the material to be tight so it looks as though its straining to hold this tight ass, and to bring the seam up to spread his cheeks apart. As for the front we would need it the same, so tight she said, as to show everyone that he doesn’t have anything there. I will teach him to tape, so it will look like he doesn’t even own a cock, she said with a giggle. I want the shirts tight also, she said, he has a no tit body, but I will make his nipples so hard that it will give him that sexy European look. Oh, she said, and 7 pair of panties. Yellow and pink if you can, I like those colors and I think they will bring out his eyes. The guy left and soon after she left saying that she had some things to do. Before she left she brushed a kiss on my cheek and let her braids touch my face. This gave me a stirring in my loins. Sometimes it hurt just to look at her.
I lay on my bed thinking of how my life had changed. I guess you could say I was happy. I thought how can that be? I have a guy who basically owns me. This is exactly what I wanted to avoid. Tiffany tells me what to and when to do it in all aspects of my life. Mike ruled me and made me do what he wanted, but Tiffany owns just about every move I make. I don’t know why, but I wanted her to own me. These emotions were very confusing but I knew that for certain, I wanted her to own me.
Later that night after supper I asked her when it would be my turn to fuck her. She laughed that kind of giggle she had and said that I would never fuck her. She said she would never give me head, or be the female in our relationship in any shape or form. It is quite ok for you to fantasize about it as much as you want though, she said with that giggle. You are mine she said and I am going to mold you as I see fit. I will never force you to do anything, you can leave whenever you please. But as long as you are sleeping in this cell, you are mine. You will continue to clean the cell, make our beds, serve me my food and clean up afterwards and your reward will be to please me sexually, again with the giggle. Do you have a problem with any of this, I hope not she said because there is more you need to learn (giggle).
That night she said she had some tools for training. I asked her what she meant by tools? She took out two clothes pins and told me that I needed to wear these on my nipples every night for an hour. She explained that I would lose a little sensation, but the result would be larger nipples and permanent nipple hard-on’s. This is extremely sexy she said and guys will go nuts to be able to flick them with their tongues. Second she pulled one of those balloons that you can tie into animals. The balloon was 4 balloons thick and filled with flour until it was about 7 or 8 inches long and about 1 ¼ inch thick. She explained that this is used to teach me muscle control. First she said you will want to be able to squeeze this so hard that it just about breaks in two. Once you have this mastered, you will need to be able to move it in and out of your ass with just your muscles. You can’t just push it out like you would poop (giggle) she said, you need to do this with your muscles. The reason for this is the desire thing we spoke of earlier. She said, you don’t want to give yourself away to everyone, just a few. You want those few to tell everyone how incredible you are. A few stories like this going around the compound and every guy who isn’t a complete homophobic will want you and be willing to give or do anything for you. Power! She said. Plus (giggle), I want you to be able to please me better than anyone ever has.
Ok, she said. This is going to hurt. She placed the first clothes pin on my nipple, not where I expected. She squeezed my nipple as close to the clothes pin’s spring as possible. This gives it the most pressure. I cried out in paid and told her that I couldn’t take it. She said stop it you sissy, I know it hurts, but you can handle it. She placed the second one on and I thought I was going to die. After 20 minutes she finally said I could take them off. Taking them off was almost as painful as putting them on. They throbbed for what seemed like hours. She said it would be an hour tomorrow night and to suck it up. Later she lubed the balloon up and slid it up my ass. I took to squeezing it pretty easy. I would squeeze then let go, she would pull it out a little to examine how much I had indented it and we repeated this process for an hour. By the time we were done, I felt like I had been fucked by a horse.
She said I did ok for the first time but would need much more practice before I would be able to move it up or down by myself. Now she said it is time to learn to give head. You have to make the guy believe that his cock is mighty. You need to worship it when you give head or the trick is to make him believe that you are worshiping his cock. She sat down and pulled out her cock and said let’s see you give head. I grabbed her cock and slowly and sensually I put it in my mouth. She started giggling, and asked me if I thought that was sexy. Ok, I will teach you how to give someone a real orgasm. First, don’t touch me with your hands at least not yet, look at it with yearning. Now slowly move over it and breath on it, now inhale it. Let your hair brush across it, softly blow on it. Now let it touch your face gently, start from the bottom and rub your face up the shaft, letting the friction force your bottom lip out. Good now gently kiss it, breath on it again and kiss softly around the head. Good she says now again slowly rub your face up the shaft letting the friction pull you bottom lip out, good now when you get to the top look into my eyes and smile, make sure it’s an evil smile. By this time it should be as hard as mine is now and hopefully there is a small amount of precum coming out the tip. If not continue doing what I said and occasionally look into my eyes. When you can either feel or taste precum at the top then move up the shaft again letting your bottom lip drag and take your tongue and gently lick the precum off. Now you can use your hands. Very gently take my balls in your hands and lick them gently continuing up the shaft to the top. Do it again and use a little pressure this time, if I am getting turned on, you will be drawing the precum out the tip. If it is plentiful, let it get on your top lip and look in my eyes while you use your tongue to lick it off. Very good she said. Now take your tongue and lick around the head. The head is the most sensitive spot and you need to be gentle here. Good she said, now as you go around the head, you need to end up climbing up the tip with your tongue. MMM she said, very good. Now take your tongue to the bottom of the shaft and lick upwards, yea that’s it. When you get to the top, cover the head with your mouth and suck back off and end kissing it. Do this 4 or 5 times. Now take my entire cock down your throat until you gag. This will make the receiver think he is huge, no matter what his size. Good she says, looks like we will have to continue your lesson another time, now it’s time to get me off. I took her deep over and over again, until I could feel her jerk and blow in and on my mouth. When she pulled her cock out of my mouth I used my tongue to find the rest of the cum and swallowed it. That was a good first lesson. I think I am going to enjoy teaching you (giggle)
The next night I was able to go 40 minutes with the clothes pins. She made me use the balloon again until I was cramping in the side of my ass. We also continued with the head lessons. The third night she said we were going to do everything at once. This way I can’t focus on the pain. I had clothes pins on my nipples, the balloon up my ass and after a half hour she made me go through giving her head again. She kept telling me to squeeze and instructing me on giving head. I was able to last over an hour with the clothes pins that night. The next day my wardrobe was ready. I didn’t think I was going to be able to get the pants on. First she taped me so tightly my balls hurt. She put the soft and silky panties on me and then she told me to put the pants on. I had to lie down on the bed and wiggle for 5 minutes before I actually had them on. Once they were on the buckle was easy to fasten, but I didn’t think I could sit down. She had me squat with my legs spread to loosen them to my figure, were her words. When she was satisfied she brought me into the bathroom to see. They were like a second skin except for the seam that pushed up my crack. The seam separated one cheek from the other and made my ass stick out. She said that it looked inviting now. She seemed excited to go out on the compound and show me off. After putting on some makeup we set out hand in hand, walking out to the track. She sent me around the track by myself to see what kind of looks I would get without her. I need to say this, I never wanted or do I want to now be a woman, but the looks, smiles and attention I was getting was intoxicating. I couldn’t help but get turned on, and the more I got turned on, the more people gave me attention. By the time we went back to the cell I was ready for anything.
I think she knew this because after we ate she left and came back with Apache. She told me we were going to try some of what I learned on him. She left me alone and told me to get ready (shower, shave, douche, makeup and perfume) She came back after with Apache. She moved over to me and did that light kiss on my lips that she was so fond of and reached in my shirt to place the clothes pins on. She told me that this is training and we won’t go into what you should do before you let a guy fuck you. Just lay down on the bed on your stomach. Apache, she said, lay on Society and push your cock in her. Don’t fuck her, just put it inside of her. He was happy to oblige. When he was inside me she told me to squeeze him. I did and he moaned. Keep it up Society she said and I did, over and over again until she saw that Apache wasn’t going to stay still anymore. She told him to get off me and sit on the bed. Now she said he is primed and you can give him head. I went down and did what we had been practicing. After going up his shaft with my face the first time, I found a large amount of precum waiting on the top. I figured he was ready and I put his cock down my throat. He grabbed the back of my head and pushed himself into my throat. I gagged, but not as bad as I thought I would. I could tell by his moaning that he was close, I bobbed and sucked and kissed until he blew his load in my mouth. The whole time Tiffany was giving me instructions. She giggled when he came in my mouth and told me to sensually clean finish cleaning his cock with my tongue while looking in his eyes. When we were done, she told me not to touch the clothes pins. To be honest I forgot I had them on. She asked Apache what he thought, and he told her that she was a perfect instructor. When will you need me again, he asked? I will let you know when I will need you again. You can leave now thank you, she said. She made me keep the clothes pins on my nipples for an extra half hour. When they came off I thought I would cry, but she kissed them and told me it will only hurt for a few minutes.
Later that night she caught me trying to masturbate and jumped out of bed to ask me what I thought I was doing. I was embarrassed but I told her I was so fucking horny from everything that happened that day. Her giggle again, she told me, you are not allowed to get off without my permission. Being horny makes you desirable. When you are horny, you unconsciously let everyone know you are horny. You think you are getting attention now, wait a few weeks and see how much attention you get then. A few weeks I said, by that time I will blow up. I have to room with you remember and looking at you makes me horny never mind everything else. She giggled again and said, don’t worry, you will be touching me. As a matter of fact why don’t you give me a message, I like it when you go from my neck to my feet. You can spend a little extra time in the middle (giggle). When I was done I would have done anything just to get off, but I didn’t.
Tiffany was right, over the next few weeks I found myself flirting with guys every chance I could. My nipples grew 3 times the normal size and they were permanently hard. During this time she I achieved bringing the balloon up my ass, but couldn’t bring it out without pushing. She taught me how to fuck properly. Everything from the proper stance to how much to sway my hips. She taught me when to use my ass muscles and when not to. She showed me how to straddle a guy and look sexy doing it and how much talking to do during the fuck. She said guys are visual creatures with egos. You need to stroke the cock, look good doing it and stroke the ego all at the same time. You need to make sure that what he tells everyone else is as impressive or more impressive than your performance. Sometimes she would use herself as the guy or if she wanted to see what I looked like while not in the moment she would bring Apache in. She would make me belly dance to music so I could keep a good rhythm when I was getting fucked. She would make me do striptease for her giving me instructions all the while. The one thing she wouldn’t do is let me get off.
When I could finally move the balloon up and down in my ass and (still not down very good) she thought that I was graceful enough during sex did she decide that I should start turning a few tricks a week. She told me that she wasn’t that concerned about my paying her back, but if something happened to her, I would need to be able to be comfortable finishing my time. She said that she would pick the guys first, so I could see what to look for in a john. You need to be picky she said. You want someone who will be happy to have a tumble with you. You don’t want someone who thinks that after they fuck you they own you. You can tell this by flirting with them, draw them out, get them talking about how they do their time and how they think it would be better. Do they think the occasional time with you would be make their time better or are they thinking you would make a great addition to their cell. You are young, not only in age, but you are easily gamed. Your biggest lesson you need to learn now is how to be street smart, or should I say jail smart. I know you flirt with some of the guys out on the basketball courts and that needs to stop. Not because I am jealous or anything of that nature, but because people will kill for you. If they thought they could get by me and Apache, they would claim you. No more flirting until you know how.
The night came when I was to meet my first customer since my training had begun. Tiffany had drilled into my head all day, seduction she said, remember everything you have learned. That night Tiffany came over and whispered in my ear, she told me to touch her ass. I was more than happy to, then she said kiss my neck and I started to kiss her neck. I started from the back and was working on the front when she grabbed my face and kissed me hard. She was turning me on so bad. I could feel my cock trying to get out of its taped bonds. She abruptly stopped and told me to take that passion with me tonight.
Tiffany met him at the door and said she had already worked out for a look out, plus Gerrad the guard was on and he didn’t care about anything. When she left I offered him a drink and sat down next to him, very close. I put my hand on his knee and asked him what he enjoyed. He laughed and said a little suck and finish off in my pretty ass. I was wearing a tight shirt and panties. He had on a pair of boxers. I had to lean over him to turn on some music and asked him if he wanted me to dance. I knew he had to have gotten a whiff of the perfume in my hair. He said that he would like that. I danced and swayed my hips and ass, brushing him lightly with my ass. I stood him up (he was tall) and I started using his legs as strippers poles. By the time the first song was over, his cock was peeping out the top of his boxers. I have had a lot and I mean a lot of johns. This was the first time I was really getting into it. I ended my dance on my knees in front of him. I looked him in the eyes and slowly pulled his cock out of his boxers. He had an average cock for a black guy, about 8 inches. It was relatively thick. What was surprising was the size of the head on it. It didn’t even look like it belonged. He was really hard, it barely moved when I pulled it out. I figured that since he was standing I would tickle his balls with my tongue. I touched them lightly, then I moved completely under him and licked from the back all the way to the front. I spread them with my tongue, then looked into his eyes and gave him my evil smile. I sat him down and began worshiping it. I was getting into it so much that I didn’t notice until I got to the tip, how much precum was pooled there. I made sure it got on my upper lip and looked him in the eye as I lick it off with my tongue. I smiled and moaned. I wanted to spend more time there, but I could tell that he was super turned on and needed me to move on. I stood up and danced some more in front of him and he started to grope at me. He was squeezing my ass, running his hand up my smooth legs and telling me he ached when he looked at me. When I was facing away from him, he pulled my panties down. The hit kit (hair grease) was already on the bed so he lubed his dick and started to finger me. When he put his finger in me, I squeezed like I did with the balloon. That seemed to really turn him on. He lowered me onto him and I felt a jolt of pain as the head penetrated me. I moaned softly which turned him on. I could tell because he pushed me down on him roughly. When my ass had all of him in me, I started to sway my hips and use the up motion with my ass muscles (remember I wasn’t very good with the down motion) He was moaning loud, I was a little scared that it was too loud, but I was in the moment and I began moving to the music up and down and gently side to side. To be honest I don’t believe he lasted another 30 seconds but who was counting at this point. I can remember his leg muscles at this point. They became so tight, I could see the definition and ripple of every muscle. I knew he was going to cum. I stopped moving up and down and finished him using the muscles in my ass. I don’t know if it was because I was so turned on or if he just had super hot cum, but when he got off I could feel every warm gush that was going into me. I shivered with excitement. When he was done he eased me off his cock, like it was super tender. I complied and grabbed the damp washcloth I had put on the locker next to the bed. Wrapping it around the base of his cock I put minimal pressure and moved up. This was cleaning the grease off his dick and pushing the remaining cum out, by the time I got to the head a glob of cum was sitting there. I gave him that evil smile and said may I? He just smiled and I took the tip of my tongue and gently licked it off him. I savored it like it was a piece of German chocolate. He said you really are a freak, huh? He said that was really great. He thanked me and left.
Tiffany came in as soon as he was out the door. She told me she was watching and I had really turned her on. She told me to lay on the bed with my legs together real tight. I did what she said. She pulled out her cock and started to stroke it looking at me. I told her I would be more than happy to take care of her also. She said stay right where you are. I did and she stroked it a little faster. She said ok now, push that cum out of your ass. I pushed and I could feel the hot cum pooling in the crease where my ass and leg met. It began running down my leg. She quickly moved over to my face and I opened my mouth and she came. I can’t explain it, not to this day can I explain it, but it was like the feeling you get when your body releases adrenaline. When she came in my mouth the pleasure feeling was so intense I felt dizzy. I told myself later it must have been because I was so turned on by pleasing her. But like I said, I don’t know why that happened. I don’t know if any of you have ever done any drugs before, but the first high always becomes the one you chase. Till this day, I have not been able to reproduce that feeling. End of part 6

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Sex with a crossdressing in a public toilet

I’d been crossdressing for a few months at this point but I’d never gone outside while dressed in women’s clothing. I’d been to the shops once, wearing one of my outfits under my normal male clothes; that’s the closest I’ve ever been but even that gave me an intense thrill. Even under a fairly loose coat, I’m sure people could make out the outline of my breast forms. Since that little trip to the shops had got me so aroused, I was determined to do it properly next time so I decided that the following Friday I would go clubbing in town.