Transvestite

Smooth Sensation

Smooth Sensation (A True Story, Honest)
God I was glad to be home, a two-hour train nightmare. Every stop from Liverpool Street on the 6pm slow train to the dreary little Essex village that was the only place I could afford to rent a studio flat. My only consolation was the bag of goodies I brought in my lunchtime and the anticipation that tomorrow was Friday and my big night in with my mysterious blind date. I had been living in my little studio flat for about a year and I have to admit, after a string of disastrous relationships co-habiting only to get chucked out when it went wrong as they found out I was a transvestite, was fantastic to have my own space especially as I loved to feel feminine and dressed as a woman every opportunity. That day, during my lunch break I had treated myself to a lovely pair of black strappy stilettos with diamante on the toe strap and some very sheer black hold ups. I have thirty pairs of high heels and many pairs of stockings but its that thrill of buying them and getting home and slipping them on to freshly shaved smooth legs and furiously masturbating to a glorious orgasm, that’s what I love and my idea of heaven. I always knew I was gay really, I guess the fact that every time I made love to a woman I had to fantasise about dressing up and having sex with men to cum gave the game away but the first encounters with men weren’t as satisfying as I thought they would be but the men I went with were not very attractive so I guess it’s the same as sleeping with an ugly woman. What I really longed for was a handsome hunk who made my heart race and I would be a total slut for and he would fulfil all my womanly desires but would the dream man ever be real?
I am very lucky really, I am five foot six, 10 stone and a size ten with a small round face and when I have been to way out club or transmission I have got lots of attention from men and positive comments from other girls. I love taking very slutty pictures of myself nearly naked in stockings and heels; this was my inspiration for placing an advert in the county newspaper. It read like so ‘Male 35,TV, Very Slim, Smooth, Feminine, very sexy and attractive seeks photographer for glamour photo session’
I thought that I might just get a few old men who want to wank on me but at least I would get some nice photos of me as I was fed up with trying to take my own photos all the time and them coming out rubbish, but I was amazed to get about ten or so responses and after I had chatted with them on the phone I had set up dates, three of them were going to come round, starting this Friday with a policeman called Simon to photograph me on Friday at eight. They were all under thirty, liked to go to the gym or played sports, had good jobs and were single or so they said but that didn’t bother me. I was a bit over whelmed really. Was I about to fulfil my dream of very exciting gay sex with a handsome man?
Friday dragged on for what seemed like an eternity, got soaked going to the train station, no seat on the train and a full in-tray on my desk and I guess watching the clock, constantly staring at the second hand going round was not helping the day pass. Eventually the day was over and I made my way home, managed to get the 5.00 fast train and a seat all the way home, even the warm setting evening sun on my face as I walked home from the station was giving me a good feeling about that night. I briefly stopped of in the off license to get a bottle of wine and some cigarettes but I was soon home and started running a hot bath and opened the bottle of wine, within five minutes of being inside. Once in the bath I gave myself a long soak whilst sipping a glass of wine and thinking of all the naughty things I would like to do with a handsome muscular man. I was almost in a trance thinking of sucking on stiff prick oozing pre-come until it shot hot spurts of salty cum into the back of my mouth. After a soak I shaved my legs, arms, genitals, bum and face, only took a few minutes as I shave my body every morning but worth it as I want to be as smooth and sexy for my man. I love having smooth skin, its such a turn on and feels so feminine. Once out of the bath and dried myself of, I painted my finger and toenails in the brightest red glossy nail varnish I could find. Next it was foundation and eye make up, blusher and a bright slutty red lip-gloss. My long blond wig went on with some large gold hoop earrings, I felt fantastic. A generous spray of Chanel perfume, I felt so sexy. I slipped on the shear hold ups that I had brought the previous day up my silky legs. I lay on the sofa and began stroking my by now stiff cock and gently fingering my arse. I was in heaven, I just couldn’t help myself and reached for a gold 7 inch vibrator out of my bed side draw, a quick squirt of lubricant and I had it buried deep inside me and frantically slid it in and out as I laid on my back until I sprayed hot cum all over my tummy. Wow, what a powerful orgasm as I lay back with my head spinning and my cock throbbing. I couldn’t wait to have a man inside men doing it for real, just the thought of it instantly recharged my sexual desire and I went to the wardrobe to select something to wear. Very high heels and a very short dress are a must. The stiletto sandals brought yesterday are perfect and a black very short silky nightdress in a size ten that clings to my skinny body would be deliciously slutty. The nightdress only just covered the tops of my sheer black hold ups and my black velvet bra with my little c cup silicon boobs gave me a lovely feminine shape.
Well they say time flies when you are having fun and before I knew it was eight o’clock and time for my photographer to arrive. I nervously paced up and down in my heels waiting. At ten passed came a knock on my door, and with my heart racing rushed to open the door. I opened the door and before me stood a an Adonis, I just melted inside when I looked into his eyes, maybe I was delirious but I just felt my heart leap. Come in, “I’m Tara”.” Hi Tara, he said, you look absolutely stunning, my fantasy woman”. “Thank you, Simon”, I said as he walked into the flat from the hall. He smelt gorgeous and I just wanted to grab him, snog him and suck his cock there and then.
I could not believe this was happening, I felt a deep desire within me that I had never felt before.
Can I get you a drink? I asked as he made his way into my small kitchen, Yes, a beer would be nice. As I walked out of the kitchen I could feel his eyes looking me up and down and grabbed a can of beer from under the table in the living room. Your going to look fabulous in these photos, you are very sexy. Thank you, I said as I walked towards him with the beer. As I approached and handed him the can he reached out and put his hands on my hips, pulled me towards him and kissed me gently on the lips. Wow, what a sensual and sexy kiss, my heart pounded as I looked into those dark brown eyes, I instinctively stroked my hand down the front of his trousers and felt his shaft thickening. He smiled and pulled me towards him again and our lips locked in a frenzied French kiss with our tongues exploring each other’s mouths. My hand was now undoing his trousers and I slipped my hand into his underpants and felt his hot fleshy and by now hard cock and began stroking it. Our lips parted and I smiled at him and led him by the hand to the sofa and pulled his trousers down and sat him down with me kneeling in front of him. I bent forward and took his cock into the back of my mouth and was in heaven as I slid my lip glossed lips up and down, doing what felt so natural. He was moaning in ecstasy as I quickened the pace of my sucking and slurping on his thick shaft. Oh, Tara, I am going to come and his body bucked and he grabbed my head and thrusted in and out of my mouth as thick hot spurts of spunk flooded over my tongue and dripped from the corners of my mouth. Oh god, I enjoyed doing that, I felt so sexy. I felt so turned on. I loved sucking cock as it excited me so much, I couldn’t help myself but grab my own cock and wank it furiously, Simon pulled my hand away from my cock and said wait a moment, you will enjoy this more. Stand up and take your dress off, so I did and just stood in my bra and hold ups with heels, he stood up and he kissed me full on the lips with our tongues in each others mouths, he bent me over onto the sofa and without warning slid his shaft deep into my already lubed arse, I moaned as he entered me deeply and I felt so slutty, he started thrusting his cock deep in and out of me and as he did so, reached round and began wanking my cock, within seconds I sprayed all my cum all over the sofa and could feel Simon pace quicken as he spunked deep into my arse.
It was the sexiest experience of my whole life, we sat and smoked a cigarette and had a drink. Tara, you are so sexy, I loved fucking you, it was so exciting, like something so naughty and forbidden. I have fantasised about it many times.
Me too, I have thought about it non-stop for years and you have fulfilled my sexual fantasy for me, thank you. I couldn’t resist it and leant towards him and gently started stroking his cock. I looked into his eyes and I could feel it stiffen in my hand. We kissed passionately and he was smoothing his hands up and down my shear black hold ups and then pushed me back on to the sofa and took my cock into his mouth. You love this don’t you, you’re a girly little slut and you want to be used,
Oh god, he was so right, within seconds of him sucking my cock seeing his masculine body in front of me I couldn’t stop my self and my cum sprayed out into his mouth. I was in absolute heaven, the most exciting sex I have ever had and feeling the most feminine satisfaction I could have ever dreamt of. Wiping the cum from his lips he kissed passionately, I could taste my warm cum on his tongue.
We smoked another cigarette and chatted for what seemed like hours and arranged to meet again, meet again we did and It was simply horny, I will tell all next time.
Tara x x x x x x

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I Just Knew It Felt So Right

Some Habits Don’t Die. If you don’t get off on this or don’t like reading about me experimenting and getting plowed by cock, then don’t read! I hope you enjoy.

Close Your Eyes Little Girly Boy

This is not a first time experience kind of story. I figured there are enough of those. Also, our “first time” is a little foggy to me, as it had been a gradual process. This is just a recounting of one experience we had shared. As usual, if this disgusts you to the point of leaving negative feedback, then don’t read it. I notice there is some hypocrisy concerning incest stories between two males versus heterosexual incest stories. You’d think that no kind of incest is “acceptable” to actually indulge in. Such is the nature of homophobia, I suppose.

Mixed Signals

This happened about 2 years ago. It is a true story. If you don’t get off on it, then don’t bother leaving small minded homophobic remarks. Just move on. I hope you enjoy. There is a part 2 if people like it.

Your tansgender girlfriend

There are times in a young man’s life when it is so full of fun and sex that it’s a wonder they survive. College is one of those times for many young men and it certainly was for me. I attended a small private collage in southwestern Ohio at a time when the world seemed to be totally focused on it’s self. Yea, it was the late 80’s and the me decade was in full swing. I can’t say that I immersed myself in the culture of the times, but just like walking across a muddy field you can’t help but get some on you.
I was in and out of several relationships with girls of many different types but couldn’t seem to find that one woman who rocked my world. Well, at least not for more that a few months. The fall of my senior year there was a new girl on campus, a cute tall blonde with a bright smile, blue eyes, and a figure that drew my eyes to her whenever she was in sight. I was in between girl friends and thought that I should go and introduce myself the first chance I got.
I saw her on and off for the next couple of weeks and never could get a chance to talk to her. She was always across the green or I was running late for class. It was starting to seem like I was just not supposed to meet her. Then one day I was down on my knees getting my mail out of my mailbox in the student union when this nicely shaped pair of long legs stopped beside me. I looked over at them and then allowed my eyes to roam up along the shapely body to pretty face of the owner. It was the new girl and she was getting her mail out of one of the top mailboxes. I finished grabbing my mail, the usual credit card offers and a note from home, then turned to face my new neighbor. She was wearing a short denim mini skirt and a tee shirt with some band on it I hadn’t heard of yet. Her blonde hair was teased up pretty big and her makeup looked great.
“Hi, I’m Thomas.” I said as I stood up and extended a hand. I knew she was tall from seeing her across the green with other students, but I had no idea how tall she really was until I was standing beside her. I’m just a tick over 5’9″ and my eyes were level with the bottom of her chin.
She flashed me a brilliant smile and said, “I know. You’ve been looking at me so much lately I started asking around about you.” My face turned bright red at being truly busted. I sheepishly replied,
“Guilty on all counts.”
“You know you have a bit of a rep for being a womanizer,” She stated flatly. “But I think you just haven’t found the right girl yet so I was wondering if you’d like to be my boyfriend.” I was struck speechless. My mouth wouldn’t seem to work at all so she filled the silence with, “I’m sure I’d be your best damn girlfriend ever!”
I looked at this beautiful girl and couldn’t believe what I was hearing. Not only was she interested in having me be her boyfriend, but she was basically telling me she’d be the best one ever! Finally my brain slipped into gear and I blurted out,
“Are you kidding? I’d love to be your boyfriend!
“That’s really cool!” she exclaimed. “Why don’t you pick up a bottle of white wine and come by my room in Jacobs Hall. Then we can get to know one another a little better.” She said with obvious meaning. “It’s room 426, at the end of the hall. My roommate transferred to another school so we’ll have the room to ourselves.” This beautiful girl leaned down and gave me quick kiss on the lips then said, “I’ve got to get to my Business Admin class, so come by around 6:00 and bring some snacks with the wine.” She turned to leave, stopped, then turned back and gave me another quick kiss. “By the way, my name’s Angel.” She said quickly, then turned and walked away.
I watched her go. Her nice round ass swaying back and forth while her long blonde hair bounced with each sexy step, she looked like a runway model on a catwalk. I couldn’t believe my incredible luck. As those long legs went through the glass doors of the Student Union and out into the warm fall sunshine I tried to imagine how they’d feel wrapped around me later that night. Oh boy, but how far off the mark was my imagination.
A Long Afternoon
I floated my way down to the local alcohol purveyor in a happy daze of sexual anticipation. I stressed over the wines to the point where the sales lady finally came over to me to make suggestions. I was holding a $4.99 bottle of chardonnay in my hand when she asked me if she could help. I delicately told her that a beautiful girl had invited me to her room to “get to know one another”. With a knowing smile the woman took the bottle from my hand and picked up one from the shelf above it. Without saying a word she showed me the alcohol content of each bottle. As a college student there’s one thing I’ve definitely learned, alcohol content is everything. I splurged and bought the $9.99 bottle, some cheese and crackers, and one of those roses that stores carry wrapped in plastic. I was now loaded for bear!
On leaving the store I looked at my watch. It was 1:48. Only four hours and twelve minutes to go. Shit.
I got back to my room and unloaded enough beer out of the frig to put the wine in to start it chilling. The lady at the store told me it needed to be chilled. Not wanting the beer to sit around and get warm I popped the top on one and looked at my desk clock. 2:10. Three hours and fifty minutes to go. Damn.
I had another beer and turned on the tube. I knew I should work on my physics project, but I also knew there was no way I’d be able to concentrate on it with Angel’s long legs still emblazoned on my eyes. The clock said 2:37. Three hours and twenty three minutes left to go. Fuck!
It seemed that time just refused to move at any normal rate for me. As it got closer to the anointed time, (Imagine a choir singing ‘Halleluiah!!!’) the damn clock seemed to be coming to a complete stand still! Just when I was starting to think I was trapped in some rip in time my stoner roommate came be bopping into the room. I’m in a pretty pissy mood by this time so I deliver the crushing line,
“If you keep blowing of your psych class there’s no way in hell you’ll pass it, even if you are some kind of psychology ‘prodigy’.” With some small distain in his voice he replied,
“Dude, I’ll have you know that I haven’t missed a class in three weeks. I’m like totally stoked about studying old Siggy. That Dude was one seriously messed up old man.” In a conspirators voice he continued, “I think he had a thing for his mom and that just ain’t right dude!” I looked back at the clock and asked,
“Did you get out early? It’s only a quarter after five.”
“Dude it’s almost six, your battery must be going in that clock, I told you to get one of the plug in…” Stoner boy didn’t get a chance to finish because I was franticly grabbing my stuff and sprinting from the room. Thankfully our campus wasn’t very large and as I went blazing past the clock tower on the commons it showed that I had four minutes to make it to her room. I put on an extra burst of speed.
Getting Acquainted
.
I’d run track in high school, but that was a long time ago and there was no trace of that conditioning left in my body. When the elevator got to the fourth floor I was still breathing pretty damn hard. I took a right off of the elevator and jogged to the end of the hall to stand panting in front of my new girlfriend’s door. I knocked at the door and heard her call,
“Just a second.” I listened as she moved around in her room for a moment then the door opened and there stood Angel. She had on a pair of jeans that had so many holes in them they were more like shorts and those long legs were so sexy showing all tanned and smooth through the holes. She had on a skin tight wife-beater muscle shirt and you could easily see her lacy white bra through the shirt. She smiled a big smile and said,
“You’re breathing pretty hard Thomas, you must be very excited to see me again.” All I could do was nod. She was a vision of college girl sexuality. “We can’t get to know one another very well here in the door way, well…I guess we could, but the RA might get a little excited about it, so why don’t you come inside.”
Angel stepped aside as I walked into a room where my views on life and sexuality were about to change drastically. I looked around the room and it appeared to be decorated the same as any other young college woman’s. About the room were scattered the usual books and papers, pictures filled with smiling and laughing people. On the floor there was a big soft rug with pillows strewn over it and it was there that Angel plopped down indicating with a hand that I join her.
Without a word she took the bottle of wine and expertly opened it with a corkscrew she had ready. Grabbing a couple of wine glasses she filled each one about half full, re-corked the bottle, then turned to one side and slid it into her frig. I was a little nervous so I took a big swallow of wine hoping that it would quickly take the edge off my nerves. Usually I’m very comfortable around girls, but for some reason I didn’t feel that way with Angel.
She sipped her wine then said,
“So tell me about yourself.”
“Like what? What do you want to know?”
“Everything. What type of music you like, movies you like, foods you like, sexual positions you enjoy. Just everything.”
“Well…I like rock music, action adventure movies, seafood, and pretty much any position you’re willing to try.”
“Good, you’re open minded. I like that in a boyfriend.”
“So…what about you? What do you like?”
“I like lots of different types of music, rock to reggae, jazz to blues. Action adventure movies are good but I must confess that I like chick flicks.” she said with a laugh. “Seafood is yummy, but nothing beats a nice thick steak cooked medium-rare. I love sex and all positions, especially the ones where I’m dominant. I must warn you that when it comes to sex I’m a pretty take charge kind of girlfriend and when I want to have sex I don’t easily take no for an answer. So if you don’t like to have sex too often you might want to think again about being my boyfriend.”
“If you’re trying to scare me away I don’t think threatening to have too much sex with me is the right way to go about it.”
Angel smiled a knowing little smile and said, “Oh, I have no intention of scaring you away. I just want you to know what you’re getting into and give you a fair chance to back out gracefully. I’ve talked with some of your ex-girlfriends and while I didn’t get any specifics, they all indicated that you like sex a lot and some even alluded that you could be a little kinky.” I blushed and tossed back the rest of my wine. You let a girl use a strap-on on you one time and they think you’re kinky. Hell it was her idea! ‘I just want to know what it’s like for a guy.’ Mandy pleaded. Later I found out she’d made a bet with a girl friend of hers that she could get me to do anything. The girl friend asked her if she could get me to let her bone me with a strap-on, to which Mandy said, ‘No problem.’ I guess Mandy was right. Angel refilled my glass as I said a bit defensively,
“Well, I guess it depends on what you’d call kinky. I would prefer to just consider myself open minded, as you pointed out earlier.” Angel chuckled as she handed back my full glass and said,
“I’m not judging. I’m actually hoping you’re very open minded and very willing. Those are two qualities that are an absolute must to be my boyfriend.” I took another long draw on my wine glass as I digested her words. Here was a girl that professed that she loved sex to the point of not taking no for an answer and telling me if I thought I couldn’t keep up I’d best move on. How could I turn down a challenge like that? I tossed back the rest of my wine, sat the glass out of the way and leaned over and kissed Angel hungrily. Not only did she respond in kind, but the next thing I knew my mouth was full of her tongue. My cock instantly stiffened in my pants.
We continued kissing as I slid my hand up and down along her ribs. She sat her glass down on the floor then grabbed my hand and placed it on her breast. It was firm and round with a hard nipple poking into the palm of my hand. I squeezed and rubbed her breast, pinching the nipple occasionally as she moaned into my mouth and tried to stick her tongue down my throat. She was on fire! Her hands were all over me, groping and rubbing me roughly, gripping me so tightly that I thought I might actually have some bruises. Then Angel really surprised me, she shoved her hand down the back of my pants and started rubbing my ass. She squeezed my ass cheeks for a few minutes then slid her hand between my cheeks and stuck her finger as far as she could into my asshole. I grunted into her mouth and tired to struggle a little, but she didn’t slow down a bit and if anything became even more excited. As she eagerly fucked my ass with her finger she continued rubbing her body against me and thrusting her tongue into my mouth. Angel was very turned on and so super horny she was almost out of control. With her finger deep in my ass I thought, ‘Damn, I think I’m being raped by this girl!’ But I didn’t struggle too much.
Finally she pulled her finger out of me and broke the kiss. She said in a husky, lust filled voice,
“Take your clothes off!” I hesitated for a second, unsure of what I was getting into, but as I watched her pull her shirt over her head revealing her round bra clad boobs it got me started on my own shirt. She asked,
“Bra or no bra? Do you have a preference?” I kinda like it when the girl keeps her bra on. I think it’s sexy. I said,
“On” She smiled and said,
“Good choice!” Angel undid her pants and started to shimmy out of them as I was doing the same for mine. She kept her panties on too, but I was buck naked and my cock was sticking straight up from my crotch. She kicked her pants off and pounced on top me. I thought, ‘This is incredible! I’ve never been with a girl this hot before! She’s as horny as I am. Maybe even hornier!’ Angel’s tongue was back in my mouth and her long body was pressed against mine. She was grinding her firm tits against my chest as she thrust around in my mouth with her tongue. After a couple of minutes she broke the kiss and breathlessly said,
“Wrap you legs around me.” I was so entranced with how excited she was that I didn’t even hesitate. I spread my legs then hooked them around her hips and squeezed her tightly. Angel’s mouth was back over mine and her tongue was working in and out between my pursed lips as she dry humped my ass. My head was spinning from the wine and it seemed to me that I could almost feel something hard through her panties. A few seconds later she stopped humping to reach down to her panties and tug at them. The whole time she continued to kiss me and rub against me. A second later my asshole was being forced open as she pushed something big and slippery inside me. I groaned in pain as my ass was forced to stretch farther and farther to accommodate what Angel was pushing into me. In the back of my mind I thought, ‘I guess she got more out of Mandy than that I was just a little kinky!’
Finally my ass was stretched open far enough and I could feel the shaft of her strap-on begin to slide into me. It hurt like hell, but my groans were muffled by Angel’s mouth and her own moans of pleasure. Then it dawned on me, her moans were real. She wasn’t trying to sound excited about using an inanimate object as a surrogate penis, she was pushing the real thing into me! When this realization hit me my first thought was, ‘Holy shit! I’m being fucked in the ass by a guy!’, but then I remembered that lovely vision that had greeted me at the door just a little while ago and I had to reassess the situation. ‘I’m being fucked in the ass by a girl!’ As strange as it may sound that actually made it a bit easier for me to accept. I’m sure there are those of you that think I was just fooling myself, but what the hell, I don’t care what you think.
She stopped pushing that hard cock into me and pulled her mouth from mine. We were both breathing hard, her from excitement and me from pain. Her face was close to mine as she said with a smile,
“My, My, but aren’t you a tight one! It’s going to be a lot of fun getting you stretched out so that I can easily slip into you when ever I want.” I was just getting ready to reply when she started pushing again. I groaned loudly as my new girlfriend forced more of her cock into me. She stopped again and said,
“I just love entering a new boyfriend for the first time, it gets me so turned on I just want to…well…” Angel pushed hard, forcing the rest of her cock into me. I cried out again loudly as she groaned in ecstasy.
“Oh. My. God! It feels so good to finally be up to my balls in a nice tight butt! I haven’t had a boyfriend for almost five months and the lack of sex has been driving me crazy!” Angel pulled back and pushed herself deep into me causing me to cry out again.
“Yea baby! I want to hear you moaning and groaning with my big girl cock buried in you! I think it’s sexy as hell when my boyfriend is vocal while we’re having sex! It turns me on and makes me want to screw him that much harder to make him moan even louder!” With that she pulled back and thrust hard into me. I groaned loudly and finally blurted out,
“Angel you’re hurting me! You’re too big, please stop!” A strained look came over Angel’s face and she started grinding her cock hard against me as she squeezed me tightly against her body. She covered my mouth with hers and thrust her tongue as deep into my mouth as it would go. With a huge groan Angel exploded in my ass. Not once, but five hard shots of cum each with its own thrust and groan. She pulled her mouth off of mine and panted hard in my ear as she tried to catch her breath.
I was lying beneath her thinking, ‘I just got the hell fucked out of me by my girlfriend and her cock is still inside me. If I’m truthful with myself she pretty much just raped me too.’ But along with feeling her still hard cock in my ass I could also feel her round firm bra clad boobs pressed against my chest and her shapely butt under my heels. This was the same hot girl I’d been mooning over for the last few weeks. The only problem was instead of me on top of her with her legs wrapped around me, she had her cock buried in me and my legs were wrapped around her. Ok, so that’s a pretty big problem.
Angel rose up so she could look in my face. She wore a lover’s smile as she said,
“That was great! I haven’t cum that hard in months! It’s so good to have a boyfriend again!” She kissed me on the lips gently then continued, “I’m sorry if I was a little rough on you, it’s just that I was so horny I could hardly wait. I wanted to jump on you the moment I opened the door to let you in! When Mandy told me you let her use a strap-on dildo on you, I knew you were the right guy for me.” She started making short little thrusts with her still hard cock as she said, “This is much better than any old strap-on. Besides I’m probably bigger than the strap-on she used anyway, and bigger is better!” Angel’s face grew serious as she kissed me again and said, “You’re mine now. We’re boyfriend and girlfriend, a couple. I can’t wait to go to dances, parties, movies, picnics, study together, all those things you get to do when you’re a couple!” Angel put on a sly smile and said sexily, “And don’t forget about all of that sex! We’re going to make love all the time! I’m going to be your best damn girlfriend ever!”
Angel sat up off of me and slipped her hands behind my knees. She pushed them up against my chest and started to slowly thrust into my ass. I watched her breasts move and sway with her thrusts. I was trying to come to grips with the fact that I was watching my hot new girlfriend’s boobs bounce and sway as she fucked me with her cock. Angel reached down and took my hands and placed them on her breasts as she said,”I want you to play with my breasts while I’m making love to you. It’s very important that you do everything you can to pleasure me while we’re making love. The more pleasure I feel, the more intense I’ll be for you.” I squeezed her boobs, playing with them and caressing them. I pinched her nipples and she moaned as she tilted her head back. The more attention I showed her breasts the more her thrusting increased and the more I began to get turned on by her being turned on. I thought, ‘What the hell! She’s still a hot looking girl and no one would ever know she’s got a cock. She sure surprised me with it and she seems to really like me so I should just give in and be the best boyfriend I can be.’
Angel put her hands on my chest and pinched my nipples hard. It was like an electrical shock went through my body. It hurt but felt good, kind of like having her cock in my ass hurt but felt good. She rubbed my chest then tilted her head back and moaned. My cock was still rock hard so I took her hand and placed it on my cock. She stroked it a few times then went back to rubbing my chest and pinching my nipples. I liked that but wanted her to play with my dick, so I put her hand back on it. Again she gave it a couple of strokes then started rubbing my legs as I kept playing with her tits. I wanted to cum pretty badly so I took one of my hands off her breast and started playing with my cock myself.
Angel pulled her head up and looked at me. She grabbed my hand and put it back on her tit, then said,
“My body is what you need to concentrate on. I don’t want you jacking off, I want you have to have your orgasms because I’m making love to you. Otherwise we’re not really connected to each other’s emotions. Just wait and let it build up until you cum from having my dick inside you, then all the other sensations that come with making love to your girlfriend will push you over the edge. I promise it will be a great orgasm, the best you’ve ever had!” She went back to making love to me and leaned up over me so her boobs were in my face. “Kiss them. Lick them. Suck on my nipples. Focus your attention on my body and your pleasure will come with mine. Keep thinking about me being your girlfriend with my big cock deep in your ass making you feel so wanted. That I’m lusting for you and that I can’t get enough of you! You’ll get to the point where you’ll love having my dick in your ass. I think you already know that I’m going to do this to you whenever I want, wherever I want, and as long as I want. You’ve never had a girlfriend like me before, because I’m going to be so totally into you.” Angel was pumping my ass hard as I sucked on her nipples and the steady flow of intent from her mouth mesmerized me. I was turned on by what was happening. I did want to pleasure her and make her feel good. More than that, I wanted to drive her wild! I wanted to feel her big cock pumping my tight ass and I loved the things she was saying to me. She really wanted me, wanted to be inside me, wanted to have her way with me, what more could a boyfriend ask for?
“When I get horny at parties I’ll take you by the hand, pull you into the bathroom and bend you over the sink. Then I’ll pull up my short skirt and make you watch in the mirror as your hot looking girlfriend feeds her big cock into your ass. I’ll make love to you so hard and fast they’ll hear you moaning over the music, begging me to fuck you harder.” Angel was thrusting hard and fast, banging the hell out of me, and I could tell that her words were turning her on as much as they were me. With my face buried in one of her tits she exploded into my ass for a second time and true to her word as she came I came too.
Moaning into her tit I had the hugest orgasm ever squirt from my dick all over our bellies. I was thrashing and convulsing as the orgasm ripped though me. I could feel my sphincter spasm around her cock with each spurt of cum that left me. I collapsed back onto the pillows gasping for breath as Angel smiled down at me and said,
“See. I told you so. Your orgasms will be much more intense if you wait.” She allowed me to catch my breath for a minute then pulled out of me and rolled me over onto my stomach. She grabbed my hips and pulled me up on my hands and knees as she said, “Come on! I want to do it doggie style now. There’s just something about doing it doggie style that says ‘I’m in charge!’ Angel’s hands never left my hips as her hard cock easily found its way back into my ass. Her thrusts started out slow and steady. I could intimately feel the shaft of her penis as it slid in and out of my now more accommodating rectum. I couldn’t help moaning with pleasure at feeling her back inside me. She spread my ass cheeks wide and pushed forward burying her thick cock to the very base in me. I grunted in new pain as she filled me completely. Now she was deeper inside me than she had been all evening. Angel leaned up along my back. I could feel her tight stomach muscles and her breasts against my back. She let out a little moan of pleasure and said in my ear,
“I bet you’ve never had a girlfriend that could do this before.” Keeping her hips tight against my ass cheeks she worked them in a little circle and I could feel her hard cock moving my insides around. “I’m sure Mandy couldn’t do any of this and your ass is way too nice and tight for you to have been with another girl like me, so I’d say that makes me your best damn girlfriend ever. What do you say?” I shook my head yes. “No, I want to hear you say it. Tell me I’m your best damn girlfriend ever.” Her cock was so deep inside me it was almost hard for me to talk, but I gasped out,
“You’re the best!” She gave me a hard little bite on the ear that made me yelp.
“I want you to say it all.” My ear was smarting from the bite and her fence post of a cock was stretching my insides. ‘Ok.’ I said to myself, ‘She’s going to be a little high maintenance in the ego department.’ I gathered up as much breath as I could muster and went for it.
“Oh Angel! I’ve never been with any girl that could compare to you! Your cock is so big and hard, long and thick, I just can’t get enough of it!” I pushed back against her and said, “You’re the best damn girlfriend I’ve ever had!” Angel moaned loudly as I said it and started humping my ass feverishly.
“More!” She commanded. Angel was still laying along my back as she humped me.
“Angel please fuck me harder. I want to know what it’s like to have my girlfriend pounding me with her big cock! I’m a dirty boy that’s all yours to fuck and use as much as you want. I’ll do what ever you say Angel, I just want you to keep thrusting your hard dick into me, making love to me. Angel you’re so awesome! You’re the best damn girlfriend in the world!” With that last Angel let out a groan and came in me for the third time.
She collapsed, putting her full weight on my back which caused me to fall forward onto the pillow covered floor, her cock still lodged in my ass. Angel lay on me panting and I thought to myself, ‘It must be over now. She’s cum in me three times so she’ll probably go limp now.’ We lay there with our bodies pressed together and I waited for Angel’s cock to start going limp. It didn’t happen.
After about ten minutes Angel started to move her hips and her still hard cock began to work my asshole again. I was just getting ready to ask her if her cock could go limp at all when she said,
“I’m so glad to hear that you can’t get enough of me. I’m not sure why, but I seem to be able to have as many orgasms as I want. As long as my penis is stimulated it stays mostly hard. I asked a doctor about it once and she said to just be thankful and enjoy it. So I do. Not only do I have a perpetually hard cock, but when it’s limp it only takes a few seconds for it to be completely hard. I can be rock hard within five seconds after I pull up my skirt and yank my panties out of the way or unbutton my jeans and push them down. That’s pretty cool, don’t you think?” Angel had slipped into a steady rhythm of pumping my ass as she talked to me about her amazing penis. The realization was now clear about what I had gotten myself into. I wasn’t just a boyfriend, I was the new fuck toy. Angel had every intention of having her cock inside me as much as possible. I said,
“Yea babe, that’s incredible. I had no idea your cock was so talented.” She kissed me on the cheek and said excitedly,
“I just knew you were the one! I’m going to make you so happy!” She pushed her cock deep into me and continued, “I can do this for hours! You’ll walk around campus with a perpetual sex grin on your face the rest of the year!” I thought, ‘I’ll be walking because I won’t be able to sit down!’ then said,
“Angel you’re so beautiful, I can’t believe that you chose me to be your boyfriend. I’m the luckiest guy on campus. Hell, on the whole planet!”
“Awww…that’s so sweet!” She kissed me on the cheek then rolled us both on to our sides. She grabbed my leg and pulled it up so she could get better penetration, then continued fucking me in the spoons position.
I can’t tell you how many different positions we tried that night or how many times my beautiful new girlfriend Angel came in my ass. She did me against the wall, both with me facing the wall and with my back against it. She lay down on her bed so I could get up on top and ride her, again both forwards and backwards. She sat on the edge of her bed and had me sit on her cock then sat on a chair and had me straddle her. Because she’d pumped so much into me her cum was dripping out of my ass and off her balls there was no where else for it to go. At one point I told her I needed to pee and thought she’d let me go long enough to do that, but since we were back to doggie style she stood up with her cock still in my ass and we worked our way laughing into her bathroom. I was standing over the toilet while Angel held my hips and continued to work her cock in and out of my ass. I stood there for a long time as she humped me and just when I was starting to think I wouldn’t be able to pee while she was inside me it finally started to flow. Angel stopped with her cock deep inside me and held still so I wouldn’t splash piss all over. Her chin was on my shoulder and half way through she reached around and held my limp penis as I finished up. I asked her if she needed to go but she just shook her head no and we started to make our way back out into the room. Finally about dawn we fell asleep together on her bed. And I do mean together, she was spooned up behind me with her cock still buried in my ass.
To Be continued??
Would love comments 🙂

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caught in drag

I was in my teens and always horny. I loved to where womens underwear and that is where the trouble started

My first cock was a crossdressers

One friday night back when I was 25 I was in the chat rooms looking for a little action. I had chat with a few ladies that got me nice and hard,but no of them lived in the same city as me and i was looking for more hands on fun. At about midnight a message popped up. “Hi I’m DeeDee whats your name?” “My name is Joe.” I respond. “Hi joe how old are you and where are you from?” She asked me. I tell her my age and where im from. She tells me where she is and its not far from my place. So i ask”How old are your and what are you looking for tonight?” Hoping to get some action.
She responded with”I’m 35 m crossdresser,I’m very passable.” “I even get hit on when i go to the clubs.” I didnt know what to say, I have fantasied about sucking a mans cock,but never had the nerve to do it. I sat there for a few moment not knowing what eles to say. “When he responded with”Did i scare you off sweety?” At this point I became very shy. “No” Was all I replied. “Are you bi honey?” He asked me. “I have been curious.” “What have you been curious to try?” “I what try to suck a dick.” “Well honey I have nice one for you under my skirt.” “would you like to see it?” Nervously I respond. “Yes.” “Then whats your address sweety and I’ll let you see it.”
I’ll said.”I dont know I have never done this before.” “It’s ok to be nervous sweety everbody is ther’re first time.” “I promise I’ll be gental and you dont have to do anything you dont want to do.” Still shy I tell him. “I dont know.” He said. “Well I know your horny so how about I bring over a porn movie we can watch it then you can just sit back and let auntie DeeDee take care of you.” “You wont have to do anything just sit back and let me service your cock.” “I guarantee until I show you my cock,you’ll sware Im a woman.” Being as horny as I am,and the fact that I havent had a blowjob in a while I agreed and gave him my address.
I log out shut off my pc. I turn out all the lightes.I have some Chrismas lights around my livingroom ceiling,it gives off a nice ambient red glow thats perfect for watching movies or getting a bj.I sit down on my couch and Pull out my cock. I start stroking thinking about the bj I’m going to get. But then my mind wonders to his cock, and I sware my cocks gets even harder. I’m thinking I’m going to do it.I’m going to suck my first cock. So here I am sitting on my couch stroking my cock thinking of the dick I’m going suck. How big is it?Will it have any hair?What would it feel like in my mouth?How much will he cum? Where is he going to cum? I have tasted my own cum before and didnt care for it,I dont think Im ready to taste another mans cum.
And at that point I hear a gentle knock on my door. Oh fuck this it it! “I’m thinking to my self. I tuck my now throbbing boner back into my pants,and get up an answer the door. Jaw dropped when I opened the door. There he stood about 5’7” black knee hight socks,short red plaid skirt the stopped right above the knees,White button down blouse. long streight brown hair that went just pasted he’s shoulders. I know the school girl look was a cliche but hell it worked for me. He even had on a pair of pink starter hightops that just made the outfit look cuter. With this sweet little sexy feminine voice he saids. “So are you going to stare at me all night or are you going to let me in?”
As he walks past me I close the door behind him. He puts down his purse and stikes a pose,hands on his hips legs close with one knee little bent over the other. tilts his head slightly to the side and saids. “So what do you think?” I was dumstruk, I was expecting some guy in a crapy wig and bad make up. “Wow your hot!” I you sure you not a real woman?” With a smile on his face he comes in closer and whistpers in my ear. “I guess you’ll only know for sure when you ready.” He gave me a pec on the cheak and with a wink of his eye and a giggle he spun around and went over to his purse.
He pulled out a dvd and when he bent down to put in in my player his skirt rose up and i caught a glimps of his ass,he had a cute little heart shapped ass with white and red stripped cotton panties. As i was stareing at his ass all i was thinking was.”Oh my god what have I gottin myself into?” He sits down on my couch closses his legs and pats the cushon next to him. “Come sit down sweety” I walk over and sit down next to him. He presses play on the remote and the movies starts.It starts out with these two hot chicks and a guy in a hotel room.the first girl is white looks to be abour 5’4′ short skirt samll tits,the is latina little shorter than the other girl hot little shorts that hug her cute little ass,tits alttle bigger then her friends.There topless and there making out with the guy.there kissing and petting,and rubbing eachother alover. then the girls get him on the bed remove his pants and start sucking him off. The useaual porno stuff.But then the girls pull down the bottoms and the both have hard little dicks,and the guy began to start sucking them both off. Oh my god he put in a tranny porn.
I look at him and he is staring at my, I guess he wanted to get my reaction. He gives me this sexy smile and winks at me. “Keep watching sweety it gets better.” As i watch this guy have hot sex with these two little trannies I cant help but get turned on. After several minuits of watching he leans into me and whispers in my ear. “Do you like what you see honey?” And puts his tongue in my ear. A shiver goes down my spine and i moan. “Oh god yes.” He giggles and kisses me on the lips.As he slides his tongue in my mouth,his hand finds it way onto my cock. His lips are so soft,he even smells like a real woman.
He pulls up my shirt and sucks and nibbels on my nipples. “UUHH” “That feels so nice.” I moan to him. He stradles me and puts his tongue in my mouth again. I grab his soft ass under his skrit and I give it a good squeeze. You have a nice ass.” I tell him.”Thank you I run and swim alot.” He tells me and puts his tongue back in my mouth. After a few moments of making out he breaks off the kiss. “MMM now just sit back relax and let auntie DeeDee take good care of you.” He said as he slid off of me down to his knees between my legs.He unbuttons my jeans and slowly unzips them. My shorts are wet from precum. “Now lets see what you have for your auntie.” As he takes hold of my wastband and pulls my shorts up and over my throbbing cock. “MMMM” “Did I do this to you or the movie?” “The movie just got me started.” The rest was all you.” He gives me that sexy little giggle and sucks my cock into his mouth.
“Oh yeah suck my cock you fucking slut!” This has got to be the best fucking blowjob i ever had.better than any woman has given me.I run my finger through his hair and hold onto the back of his head.As his head is bobbing up and down I can realise that this is no wig. He is playing with my balls and even rubs his fringer on my asshole. As im getting close to cumming I’m thinking is there really a cock under that skirt? If so I want to see it,I’m ready to suck it.
I look down at him and pull his head up.”UUUUHHHH” I im getting close i need you to stop!” He looks up at my with his sexy eyes. “Whats the matter sweety?” “I want to do you now.” I say to him.”You sure sweety?” “Yes I’m ready for my fisrt cock.” We get up,I take off my pants,and shrit.And she takes my place on the couch,slouching down so his butt is just on the edge of the couch.With his legs together he slowly runs his hand up his thighs and pulls up his skirt. “You ready sweety?” He tells me. I slowly nod my head. “Ok sweety here it is.”
He places his hands on his knees and slowly slides them up between his thighs,spredding his legs apart. I could see the bulge in his panties. He grabs the crotch of his panties and pull it to the side pulling out his cock.It;s semi hard and and already like six inches and cut. “You want to touch it baby?” I put both my hands on his legs and Slide them up feelling how soft and smooth they are.He must use lotion on them every day. I slowly take his cock in my hand. Like his legs there is no hair on it. I wrap my fingers around it and slowy stroke it, I can feel it getting harder it my hand. It has to be a good 71/2 to eight inches! I stroked his cock up and down getting a good feel for it. “MMMM that feels nice.” He moaned with that hot sexy fem voice of his.
I get my face closer to his cock. This is it, I’m going to get my frist taste of cock.I am so nervous,my heart is pounding as I get closer to his cock. I look up into his eyes and he gives me a sexy smile,runs his fingers through my hair and saids in a low sexy voice. “It’s ok sweety,take your time.” I’ve never been so hard,my heart is pounding so hard I feel like it mite explode. I will never forget the feeling of when his cock first touched my lips,my lips went pasted his head and half way down his shaft, I fell in love at that moment.I held his cock in my mouth taking amoment to feel it. I can feel his pulse of his heart as his cock throbbs in my mouth. I swirl my tongue around the head getting a good taste of it. I slwoly rise up to his head and back down his shaft. I get in a good rythim,as i bob my head up and down in his lap. He reaches out and places his hand on my back and rubs it up my neck to the back of my head and back down again moaning. “UUUHHH” “Oh yes your doing so good.” “Just a little more sucktion baby.” “MMMM just like that.” This is so fucking hot,I am so turned on that my cock is dripping pre-cum into a puddle on the carpet. I have seen many women doing this to me and I finaly understood them. I’m inlove with cock!
“UUUHHH” “Your so good at this.” “You sure you never done this before?” He asked me. I just shake my head.”Ut-ah” and continue with my sucking. “Well your a natural honey.” I just look up into his eyes and smile with his cock still in my mouth. “Oh god im going to cum baby!” “Do you want it in your mouth sweety?” I slowly pull his cock out of my mouth,and swirl my tongue around the head a bit. Stoking him up and down i look into his eyes and say.” could you shoot it on my chest auntie DeeDee?”
He smirks and stands up,bends down and gives me a pec on the lips and saids. “Sure sweety” He has me lay on the floor flat on my back,then he straddels me just above my cock. My cock is rubbing the crack of his ass,soking his panties with my pre-cum. Kneeling he lifts up his skirt thrust out his cock and strokes if for me. “Oh god baby here it cums!” Just then his first shot of cum flies out and lands on my forhead,its a long string from my forhead to my chin. The second shot hits me in the mouth,the thrid rope is not as powerful and hits me under my chin stretching down just above my bellybutton.The last few drops making a puddle on my stumach. I love the feeling of warm cum shooting on my body. He is now smearing the puddle of cum on my stumach with his cock. He leands down and licks the cum off my mouth and kisses me.
“So sweety how did you like your first cock?” he asked me. I tell him.”It was awsome and i plan to do it again.” He kisses me again and asked.”So stud you think you up to fucking my sexy little ass?” I decline.”I’m sorry i dont think in ready for that yet.” “It’s ok sweety,when you are you give me a call.” “I want to be your first for everything.” “I may even top you when your ready.” I just laugh. “Well I’m definitely not ready for that.” He reaches back and feels my cock still rubbing his ass.”Well It seems you are ready for another session with my mouth.” He said.
He slid down between my legs and onces again I soon felt his hot breath on the tip of my cock. He raised my cock and captured my pre-cum coverd head between his lips. He began to strok his hand and bob his mouth,I was on the edge. He looked up at me and said. “I love your cock,I could do this all night.” “I dont think I can take another minute of this,much less all night.” With that he dropped his mouth down and slid my entire cock straight into hi throat. I nearly lost it as he began to fuck his throat with my cock. My hips came up as my balls contracted and I grapsed at the carpet and tried to hold back,but it was all over. “Oh fuck I’m cumming!” And let loose a blast of cum,a second huge spurt,a third,then a forth. I had never cum like this in my life,and he swallowed every bit of my cum,not letting a single drop escape his hungery lips.
It seemed like hours before i came down from my orgasm.He pulled my softening cock out of his mouth with a load pop.Came up to me and slid his tongue in my mouth,gave me a hard passionate kiss,and grabbed his purse pulled out a pen and with a giggle he began to write something on my now soft cock. when he was done he kissed my cock got up. “Thanks for the night sweety I had fun.” And left me laying on the floor with my cock freshly sucked and coverd in his cum. I lay there thinking to my self this was the best night of my life. I look down to see what he wrote on my dick. It said call me anytime sweety and left his #. I run a finger throw his cum on my face and I put it in my mouth. and I say outloud.”Oh you bet your sweet ass i will.”

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