Gang banged the wrong way
I was tied up bent over…
I was tied up bent over…
In this story, young Keven becomes a woman substitute for sex hungry prison inmates.
It’s now a week since Jason was raped and it doesn’t look like stopping any time soon
This is based on a true story. A friend of mine, who is an addict, told me about these things he has done. Obviously the dialogue is fictionalized but the events are very close to reality.
As is the case with most hard drug users, you start off small and end up making your way up. Since I was 15 I had been smoking weed. One of my friends had introduced me to some other drugs like meth or coke a few years later. The weed was still a big influence but it all seemed so tempting. It was a different high and on a much higher level. I figured I could do it and just stop if I wanted to, which ofcourse did not work. I’d learn to accept that. As time went on I began not to care because it felt too good to stop. All my problems seemed to go away when I was away on another plain.
Stacy, my girlfriend of two years, only smoked weed but knew that I did harder drugs. She never really asked for details and we always enjoyed our sex while high. It wasn’t that we were performing better but the drugs gave that illusion. It became apparent that I also enjoyed crossdressing and it didn’t bother her at all. I’d never do it around her because it wasn’t her thing but it was something she didn’t mind me doing.
Last year I lost my job and it was hard for us to afford all of our bills, let alone my habit. I’d scrape up change, pick up cans off the streets, just to get enough money to get me away from my worries.
I’ve always been a very sexual being and when Stacy was gone, I found myself looking at shemale porn on the internet. The thought of me sucking a man while dressed as a female really turned me on, but I had never done it. As it became obvious that I wouldn’t be able to afford my drugs as much, I started thinking that maybe now was the time to explore that other side.
The withdrawals were hard to deal with and desperation sank in. I was willing to do anything for just a little cocaine.
I got online one day when my girlfriend was at work and went into a local chat room. I’d chat with different people but if they didn’t have what I wanted, I stopped immediately. Luckily, there was a guy who was just 20 minutes from me who could get me some coke. His name was George and he was a cab driver. Maybe not the brightest idea, I gave him my address and he’d be over in a few hours.
I put on one of my girlfriends tank tops and one of my tight leather skirts, then checked the clock. It was getting close and I was nervous but the craving outweighed that. The lipstick was a brighter shade of red than I wanted but it didn’t have to be perfect.
A car horn went off, so I looked out the window and saw a taxi. I zipped up my boots and ran outside, hopping into the front seat next to him. He was actually pretty attractive. I didn’t expect that at all. Maybe it was his blue eyes that made him more interesting.
“You are a very pretty girl. I’m surprised. So, where is the money?”
“See, that is the problem. I’m low on cash right now. This is all I have.”
He stared down into my palm where a few bills were wadded up and laughed.
“That is not enough. Don’t fuck with me little faggot. You waste my time.”
“No, no, no I’m not wasting your time. I’m sure I could do something else for you on top of the money. Come on, I need this.”
“Okay. Fair. Do a good job and it’s yours.”
George unzipped his pants to reveal a fat 6 inch cock. Even though this was the first time, I didn’t waste a second. The fat head just barely fit into my mouth. His fingers ran through my hair, gripping onto it as I licked and sucked the head. I kept my eyes on his, giving him a seductive look, which he enjoyed.
Apparently he wanted me to take it all as he shoved my head down, causing his shaft to move towards the back of my throat.
“Yes, suck me fag boy. Suck my dick.”
Going into this, I figured I’d be doing it real quick just to get what I wanted, then get the hell out of there. Though the tranny porn always got me excited, this had been business in my mind. That view had quickly changed. He no longer had to push my head down, I was taking every inch all by myself.
“Take it deep, I’m going to cum.”
My tongue swirled around his thick shaft. Then I made my way up to his bulbous head. As I took half of him into my mouth, I stroked from my lips down. His moans got louder and I sucked harder as I felt the warm salty taste on my tongue. I pulled my mouth away and watched the cum gush down his head before proceeding to lick it all up.
“Mm, that was pretty nice. I’m surprised you’re not snatching this shit from me if you are that desperate,” he laughed. “Here, take it. Enjoy. Get out. I got to get back to work.”
Part of me was disappointed that he came so fast but the other part just wanted to get back inside.
I thanked him and ran inside just as fast as I had run outside. In no time, I was in another place. The worlds problems seemed so far away and the pain went away as well.
Unfortunately as I was coming down, in the corner of my eye I caught a stain on Stacy’s shirt. Shit, I had gotten that cabbie’s cum on her tank top.
I didn’t get to enjoy the last bit of my high because I was so paranoid about her seeing this and finding out what I had done. For the next hour I was washing and drying the shirt so I could place it back where it belonged. She walked in the door probably about 15 minutes after I had finished. Too close of a call. If this was going to happen again, it couldn’t be here. All that was playing in my head is, “Somebody saw. One of the neighbors saw you sucking off this guy and they will tell her.”
Luckily, she never found out about that but within a few days, that craving came back. It was hitting me hard, so I hit the internet chat rooms again. This time there was nobody anywhere near me that had some drugs I could score.
One of my good friends, Mike, called me up and told me about a drug dealer that could possibly help me out. He was bisexual and very attracted to trannies and crossdressers. Mike knew I crossdressed and this guy was his dealer. They had been talking and brought me up in conversation. The guy said he could work something out if I really needed it. At this point, I desperately needed it and figured it’d give me a chance to have more interesting experiences.
As instructed, I showed up at this guy’s house at three. It was a fairly nice place considering the neighborhood, which consisted of mostly run down homes. I didn’t even get the chance to knock on the door before it opened. A busty latina opened the door and welcomed me in. A large black man sat on a black leather couch with a very attractive asian girl. They were passing a roach back and forth.
“Come over here and sit by me baby,” he said as he patted the couch.
I looked around at all the nice stuff this guy had. Maybe it shouldn’t be surprising since he sells all sorts of drugs but I was in awe. Nervous but in need, I sat down next to him. He passed the roach my way and I deeply inhaled.
“You look real good girl. I see that you wore the fishnets like I asked. That’s a sexy skirt. Love leather.”
His hand made it’s way to the black leather skirt. He rubbed it, pressing it down against my dick. The friction started to make me hard.
“Since you so fine, I’m going to make you a deal. You there for me, I’m there for you. Need some shit, come this way. You will get whatever you want as long as you do what I say. Think I’d like to tap that pretty little white ass of yours.”
I was very nervous now. I’ve used my girlfriends vibrator in my ass but it was nothing like this guy’s cock.
“I really need some coke now, so if that is what you want, I’ll do it. I’m yours.”
“Call me Big Daddy.”
“Okay. I’m all yours Big Daddy.”
“Good. So get down on your knees and get my dick wet so I can slide that shit up in your ass.”
Immediately I dropped to my knees and pulled his pants down. His cock was very large and thick, which scared me a bit at first. It was even more frightening as it started to grow when I wrapped my pink lips around it. I’d never seen a dick this big other than on the internet. He had to be at least 10 inches. I’d gag every time I got half way down, as the saliva dripped from my mouth onto his balls. My hand moved up and down the lower part of his shaft with a tight grip. I found myself moaning in between popping his big head out of my mouth. Even though I knew it’d hurt I was starting to crave that big black cock inside of me. I stroked all 10 inches furiously as I licked my lips.
“Come on Big Daddy. I want your black dick inside of me. I want you to tear me up.”
Like when the drugs would take hold, I became another person when dressed as a female. Not only were the drugs important now, so was pleasing him. I leaned over the table with my ass in the air. My cock was semi hard as it hung down for him to see.
“Presentin that ass for me and look, baby got a nice little prick.”
His hand came down with a lot of force on my right ass cheek. He moved the leather skirt up a bit and did it again, this time on bare skin. It hurt a bit but the pleasure was on a much higher level.
“It’s all yours Daddy. This ass is yours.”
“I’m going to rip that shit up. Tear you apart little girl. Ready for this big dick?”
“I’m ready. Shove it in!”
At first, regret was the biggest thing running through my mind. Why the hell did I tell him to shove it in? Nothing this big had been inside of me, so it should have been eased in. He did exactly as I told him to do. The moment the head stretched my tight hole, I had to bite my lip to stop me from screaming.
“Damn. Somebody never had a cock in they ass? Bleeding.”
Through groans of anguish I managed to spit out, “No. You are my first.”
“Ha ha. Love that shit. Break you in little boy! Fuck you like a woman. Ya Slut.”
The pain was unlike anything I’ve ever dealt with before. There was so much of him and he didn’t want a single inch to be outside of me. I grabbed my cheeks and pulled them apart, trying to loosen up. It was hard not to clench, but I managed after a few minutes. Once I was able to do that it was more enjoyable.
“Mm, that’s a tight ass. Play with your cock for me. Rub it.”
My cock was throbbing so I began to stroke it as he plowed me from behind. As he quickened his pace, I found myself pushing back with his motions, driving him deeper into my rectum.
Every time he called me slut or whore, I really felt like it and it drove me crazy. I’d thrust my ass back into his cock, begging for more. He’d fill me up then pull all the way out, slide it between my ass crack, occasionally smack it on my cheek before shoving it back into my anus.
“Fuck yes. Fuck my ass Big Daddy. Fuck me harder. I’m your whore. Love your big black dick.”
“Mm baby you never going back to anything else. You gonna crave this fucking black cock. You want my nigga cum in you bitch?”
“Yes. Yes. Fill me up.”
He squeezed onto my sides and fucked me harder than I ever could have imagined. I had to grab onto the table to keep from falling over the other end. We both were moaning as I felt him quickly thrust deep and spurt inside of me. I kept thinking, “You whore. You are being filled by a big black cock while your girlfriend is at work. He’s filling you with his seed. You fucking slut.” Those thoughts combined with the huge cock in me pushed me over the edge. I started shaking, my ass clinched tightly onto his thick meat as I shot my semen all over his table.
“ Man. You got a nice ass.”
“Thank you Daddy. My girl is going to be out of work soon, so I got to get my shit and go.”
“Uh, not quite yet. Just because my jizz is in your ass, don’t mean you don’t have to gobble it up. Push that shit out. Eat it for your daddy.”
Immediate thoughts were, “Fuck that shit”. Unfortunately, the craving was becoming too much so I sat back down on the couch and spread my legs. I pushed hard and nothing was coming out.
“Push harder. Put your hand under there. Get it all.”
I positioned my hand underneath and pushed again with better results. This guy came like two guys! I couldn’t believe how much semen was in me. It covered most of my palm, but I knew I had to do it, so I did. Every single drop.
“Very good baby. Here you go. Give Daddy a kiss before you go. Thanks baby. Call me up next time you need some shit or just a good dicking.”
“Yep. Thanks. I guess I’ll see you around.”
My watch said 4:38 . Shit. Stacy was going to be home any time now. I got high in Daddy’s driveway and drove well over the speed limit most of the way home. She pulled in right after me. I lied and told her that I was about to go to the store for milk. Of course we had milk and she told me that. I guess she figured I hadn’t looked hard enough, and never bothered to question me.
A few nights later I was out and going crazy from withdrawals. Stacy had the night off so I knew I couldn’t go get some more. It became too painful and it was impossible to sleep. I called Big Daddy at 4 am and told him my situation.
“I really need some shit now. I’m losing my fucking mind over here.”
“Shit, get your ass over here then. I’m going to be up awhile. Took too much shit.”
“Fuck. Problem is, my girl is sleeping so I have to sneak out. There is no way I can dress up for you without her knowing.”
“Baby, just get your ass over here. I got something nice for you to wear for me.”
I hung up the phone and made sure to be very quiet as I closed the door. My car was louder than I wanted it to be when it started, but every thing was because I was trying to be quiet. It was dark and every one was asleep as I drove off into the night.
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My gf explains exactly what happened to her when she was 11 years old.
to start off i have never been a normal guy. i first began wearing womens clothing when i was about 10 years old. i kept this a secret from everyone for about 5 years before my secret was discovered b
She looked just as she did online and as I walked toward her, she smiled back at me. Nicole was wearing a white top and a short little skirt, and her smile made me smile.
This is part 3 of my story. Please read the other 2 parts first.
This is the wonderful story of me fucking a ladyboy.
Another of my parents attempts at making me a “man”.
The follow up story to She Swings Her Own Bat.
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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Just a nice little story about a pleasant surprise.
TRUE – my encounter with a Transexual Pro
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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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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my wife, a sexy tranny and a lot of fun
my wife, a sexy tranny and a lot of fun
Introduction; this is a follow up to my budding relationship with a beautiful girl I met while at university. I have appreciated the good responses to the original story, and hope this doesn’t disappoint. And to the two anonymous people who read and said it was not possible for us to each have our member inside the other, do some research while in the video section of this website and you will see that it is in fact not only possible but pleasurable for both parties.
It had been a strange weekend to say the absolute least, I am a young guy who is in a college with hundreds upon hundreds of fine 8s, 9s and 10s, but was I falling for this person who had for lack of a better term extra parts. I should’ve chalked it up to a new and exciting experience with something I knew little of, yet found it surprisingly enjoyable. On one hand Naomi was gorgeous in almost everyway possible, smart, witty, enjoys the things I enjoy, yet the shear taboo factor weighed heavily upon my head. While in my dorm I phoned a very close friend as well as a future brother in a matter of speaking.
The call consisted of Alex, my friend, basically having to drag me away from studying to take a drive and go for a smoke. He picked me up at the west entrance of the campus, we preceeded to head out of down while I twisted up an L, or blunt to the lay person. Alex said to me, “so Dan my man, what is new and exciting in your life other than pledge week?” While taking another large drag, coughing loudly, “Alex, you’re a guy I feel I can be real with, right man?”
“Shit what do ya got I can handle this and give my best guess to the situation in question.” He said as he blew rings towards the glass on the windshield.
As I grabbed at my rolled masterpiece, “so your have walked to my poly/sci class with me before right?”
“Yeah, but what in the hell does that have to do with why you’re acting like someone killed your cat?” Alex said while taking a left on the dirt road in the hills.
“Dude you know damn well I loathe felines, but remember that short blonde I have pointed out saying I haven’t had the stones to talk to?”
Alex looking at me in both a puzzled and sly way, “yeah, yeah I think so the one with the large for her frame cans?”
I just laughed “ha, yeah man so I talked to her, we met up at the library, have shared a meal, been to her dorm after hours. I just need some advice of what I should do.”
Being that we lived in a conservative state yet in a very large widely open-minded and progressive city I felt with that fact Alex grew up here he might have some insight.
We still were on our drive through the country with a fair amount of blunt still rolled and on fire Alex asked, “well first what happened between the two of you?”
As cool as I could be I said “we ended up making out on her bed and then fooling around for a fair period of time. But there was some extra equiptment involved.”
“oh nice did you use a chin-do or something?” Alex laughingly said.
With a perplexed look on my face with a cigar of sorts in my mouth, “the fuck is a chin-do? And well ya see she well is not like all girls I suppose.”
Smiling Alex says, “sound it out chin do, a dildo on ur chin for cunnilingus dude. And what do you mean she is not like all girls?”
“Dude no bullshit you will keep this between us, you and I?” I said being utterly nervous and fearful that my friend will think I’m crazy.
Alex being his typical cool self, “yeah you me and this roach we have here, what is the deal dude?”
“She is well, she is special I guess, she has both male and female sex organs.” I said while looking out the window hoping to hit a guard rail.
Alex jerked his ride to the shoulder of a small dirt road not removing, but lowering his sunglasses on his nose said “like she is a hermaphrodite? You mean she had a hang down?”
All the while of this session of smoking cannabis filled swishers I felt a vibration in my pocket, looking at my phone I saw not only missed calls, texts but also a voicemail from none other than Naomi. I casually avoided my bothersome cellphone and said, “yes that is the case at hand man, but the thing is she really cool and I can totally feel comfortable with her but I still don’t know what to do about the whole her having extra items she contains.”
Alex looked at me again with an earnest look “Dano you don’t need my blessing but if she seems cool fuck it, give it a go. Its college and you only have it for a short period of time enjoy it.”
“Alex I appreciate the vote of confidence I really do, I need to get back to talk to her but I’m way too high but maybe that is a good thing to just lay it out there.” I said as I finally felt blood in my extremities after being in shock for a long period of time.
We headed back towards town while listening to the carter 3, I listened to and read the her messages, it seemed she to wanted to talk. At first I thought good maybe she felt similarly or that she didn’t want to see me again. Being stoned didn’t help my already racing mind about what I would say when I met up with her.
As we pulled into the lot Alex gave me another sign of good faith as I saw her walking from class I went over to see what she wanted to speak to me about. We greeted each other as we decided to go to her dorm as she lived alone to talk. Naomi on this day was looking as beautiful as I ever saw her in class she was wearing short shorts with a turquoise paisley top with a pony tailed braid in her flaxon locks. I decided to jump for some semebelance of affection as I grabbed her hand and held it firmly as we walked into her hall and into the elevator. She entered her room first as I quickly shut the door behind me I could only look into her eyes and see that she was a truly fine creation in this utterly flawed world.
Naomi spoke first and said “Dan I think we should talk about what happened and how it escalated so quickly, I think you’re a great guy and want to get to know you better.”
“okay good that is exactly what I was thinking. You are so fucking hot and I really want to know all about you, would you be my girlfriend?” I blurted out almost in a panic.
“Are you serious Dan, we just met recently?”
“I don’t care I felt a real connection with you and if I don’t do this I could miss out on something aweso…” I was cut off as Naomi literally jumped from her chair to mine and jammed her tongue into my still talking mouth.
She seemingly ripped off my shirt as well as her blouse, I edged my way down from her mouth to her neck and then onto those breasts. As I nuzzled at her supple tanned mounds I started letting my hands do some exploring as I rubbed her thighs and to her d and p. I slipped off my board shorts and briefs being totally nude, as Naomi took off her demin shorts and her panties. We held each other as our parts intertwined and touched and began to become warmer and harder. As we kissed each other deeply she made her way down to my member with her right hand and began a slow up and down to increase blood flow for our upcoming endeavor.
All while of us making out heavy and being jacked I followed suit and used both hands one on her vagina which already seemed as well as a swamp and the other onto her member and did as I did when touching myself and steadily jerked her as she grew in my hand. She guided me off of her bed and stood me up as she took my swollen dick pushing maximum density of 8 and a half inches halfway into her warm and wet mouth. As I inched closer and closer to the base of my pelvis into her throat I felt a twitch in my balls, I thought I was gonna shoot but it wasn’t that, it was Naomi with part of my scrotum as well as the full length of my unit.
This kept up for sometime until I felt as though I needed to repay to oral favor in some capacity. I decided to first attack her pussy while still paid attention to her girl cock with my hands. As I lapped up at her dripping cunt she started to shutter and shake as I was engulfed in her fluids which tasted sweet and smelled amazing. After giving her pussy an orgasm I felt up to a bit of penis play as I licked at her head, then from the base of her cock which attached directly to her sloppy puss. As I took her whole head in she bucked and started to face fucking me. I started to slobber and gag as she used me like a sex doll with a pulse, she willfully slowed down with fucking my mouth like I was a paid dick taker. I was so insatiated with her that I picked her up and threw her onto the bed grabbing both of her ankles I lifter her ass into the air and began to devour on her asshole with more enthuiasim than I paid to her pussy.
After two hours of orally pleasing each other I decided I needed to make my way to a hole which would encompass my cock. Naomi got on her back with her knees up in the air I lined up my rock hard cock for her pussy when I threw her a curveball I entered her butt slowly as she took a deep breathe and held it in. I pushed in ever so slightly as she finally exhaled I was halfway in as she urged me to press on with my exploration. OH FUCK, FUCK ME IN THE ASS she screamed in my ear as I finally bottomed out in her. I was on top of her with my cock in her ass our chests pressed together as I felt a wetness of my stomach. It was her penis leaking out from her pleasure from me working hard on her back door. I was getting very close after the whole oral session and getting in a perfect girl’s butt. I started pumping furiously as I blurted out, NAOMI I’M GONNA BLOW BABY, AHHHHH WHAT DO YOU WANT ME TO DO ABOUT IT?!?!?!?!
She said to just let it flow as I was in her au natural about to burst, it hit me like a prize fighter as the first spurt felt like a pint of milk the few following decreased in size as I finished after 6 hard ropes into her beautiful ass.
I finally began to lose so mass and steam as I slipped out of her bottom, she still seemed very game for more interaction. Naomi was still very hard as I was softening by the second she grabbed me and slammed me onto her bed first with my chest down. She decided to eat out my ass just as I did to her before I gave her the whole enchilada so to speak, she lapped up at my asshole until I could feel like I was wet and like a geyser, ready to explode. She entered as I did, very slowly and soft I could feel the tip pass the ring of my hole. Naomi then slammed into me violently for several minutes I was in pain until I felt a slower pace from her. She had to have been somewhat close as she grabbed my waist and pulled me up into doggie I got a mean western grip handjob from her as I felt a liquid substance being injected into me. Her streams weren’t nearly as long lasting or thick as mine but I felt a considerable amount of spunk deep in me.
After each of us thouroughly had our bums fully service and hydrated we held each other face to face as we slowly drifted off into a log-like slumber. I woke up after a few hours of sleep as I gazed down at my girlfriend, oh fuck me wait she never answered she broke the conversation by inserting her tongue into my larynx. Did Naomi slyly blow off the question simply to not answer it or was it excitement and no need for talking? Why my mind goes racing wild after a crazy night of sex with a beautiful creature is beyond me, it could be seen as a good thing to act as a second opinion to my primal urges I get in my manhood. It felt like I was getting the rub, and not like a cock rub but like she was playing me, yet I thought it was my subconcisous getting the better of me. As quietly as possible I got up and made my way to her bathroom for some much needed release in a different way, then I climbed back into bed with Naomi.
While I crept close to her to spoon she flipped around and faced me and said, “to answer your question yes, I would love to be in a relationship with you. I want to apologize for not answering right away but I had to think about it and was elated by you asking.”
“Well I am happy to hear that and I thought you maybe weren’t interested and you felt bad haha,” I said with a smirk as I kissed her on the forehead.
Naomi kissed me back on the nose and said, “no I was interested from when I started to sit by you in class little did I know you want to be my boyfriend.”
“When I first noticed you I knew there was something there, I couldn’t put my finger on it but I felt there had to be a chance at a cool thing. Also I think that you are very interesting on so many deep levels and want to get into your subconscious I dig you”
“Dan I want you to know I feel the same way as you and I want the same things, but I think we should get a little fun out of the way before we have class.”
As soon as she finished her sentence she lept onto me with the ferocity of a jungle cat, kissing me as she dry humped me. Naomi moved so quickly she got my morning wood into her vagina which still seemed moist to the point of full hilt insertion on the first in stroke. Naomi kissed me hard as I laid into her thoroughly. I got up and while lifting her around her knees while interlocking my fingers on the small of her back. We made our way to a wall as my raging boner found its way back to her waiting pussy. After about twenty minutes of a standing bang I felt a rumble in my stones, being that Naomi was my girl friend I felt cumming in her was fine I let it go and finishing the fourth spurt I was spent and stayed inside her, feeling that something was going right.
Naomi said, “well we better get ready for the day and unless you want to smell of sex you better hurry into the shower with me so we can make it to our class on time.”
“Sounds like a plan to me Naomi I’ll follow you.” As we showered and lathered each other up so we could be prim and proper for class shortly after our morning interlude. I made my way into her room and got dressed while she was still getting ready I snuck in and gave Naomi a kiss in the bathroom and asked, “so next week is thanksgiving have any plans?”
“Nope nothing really staying here as my family is a ways away, what did you have in mind?” she said.
“Well why don’t you come home with me seeing how we’re dating, its new but might as well see where it can go,” I said as I kissed her and held her hand on the way to class.
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Read Past Stories Before This One.
A true story of my first time with a tranny