Fantasies Fulfilled

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Tranny and her boyfriend fulfill fantasies.
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This story is part true and part fiction. It basically happened as told with a few embellishments.

*

I enjoy crossdressing and do so when ever I can. About the only time I dress as a man is to go to work. I have been doing this since I was eleven years old. I love to have sex with a man as if I was a woman and really think I should have been born a girl. I think like a girl and naturally act like a girl. I have to go to great effort to act like a man at work and not let my true self show there. I have accepted that for now I must lead a double life so at work I'm a guy and at home I'm a girl. I use the internet to meet people who are accepting of this. I am also a total slut. I love hooking up with men, women, couples, or groups for casual sex. I will fuck just about anyone. Something about fucking someone I just met just gets to me. I love it!

I met Ken one Saturday night when I was dressed like a total slut and had posted an ad on craigslist looking for men to hook up with. He answered my ad and stated that he wanted a blowjob and wanted to remain anonymous. He wanted me to have the lights off and porn playing and no words were to be exchanged between us. He would come in, drop his pants, I would blow him, and then he would leave. While this wasn't quite what I was looking for it did sound interesting. I've never done it quite this way before and it wouldn't take long so why not. I could do this and still have plenty of time to find another date for the night. I sent him directions and he was on his way.

When he arrived I was waiting at the door and as instructed I had the lights off and porn playing on the TV. I had put in a good blow job movie as it seemed like the most appropriate for this occasion. By the dim light of the TV I led him into the living room and positioned us so that he had a good view of the screen. I dropped to my knees and helped him pull his pants and boxers down to his ankles. With my body blocking the light from the TV I had to go by feel rather than sight so I reached out and grabbed his cock and stroked it a few times. I kissed it and licked it up and down a little before taking the whole thing down my throat. It was a perfectly proportioned cut 7.5 incher and he smelled great, so clean and he had sprayed something down there that smelled expensive. He tasted so good! I can honestly say he had the best tasting precum I've ever tasted and I was thoroughly enjoying pleasing him.

I brought him to the edge several times before backing off and slowing down so I could make this last as long as possible. Soon the inevitable happened and he fed me squirt after squirt of the best tasting cum I've ever had. When I had gotten all he had to give he pulled up his pants, said thanks, and left. I didn't expect to hear from him again.

A couple of weeks later I got an email from him. He said that he really liked the blow job and was interested in doing it again. I told him that I would blow him again if he would fuck me. He said he had always wanted to try anal sex and would like to try it with me. When he came in this time I had the porn playing again but left a small lamp on in the corner of the room. It wasn't bright enough to spook him but gave off enough light so that we could see each other. I had taken my time getting ready and was silky smooth and dressed like a whore. He told me he thought I was hot when he came in and I returned the compliment. I took him to the living room and soon had his cock down my throat. I repeated my performance from the week before but stopped before letting him cum. I took my panties off and bent over the sofa and reached back to grab his cock and guide him in. He had obviously not done this before. He was kinda just stabbing at me with no real rhythm and it slipped out a couple of times and had to be reinserted. He kept going at it though and it didn't take long for him to fill me with his seed. When he was done I licked him clean and sent him off. This started a relationship that exists to this day.

That was two years ago and we have fucked lots of times since then. I slowly added more lights every time he came over and he gradually started spending more time here. Now he'll stay the night sometimes. We always lay in bed or on the sofa and cuddle after sex and he kisses me like I'm a true woman. When he sleeps over we either spoon with him behind me and his cock nestled between my ass cheeks or he lies on his back and I lay on my side with my face resting on his chest and my hand on his cock. I feel so much like a girl when we sleep like that. I love it. So warm and secure. We have had sex in any position either of us could think of and have done some kinky things also. My favorite thing is to have him spank or cane me good before fucking me. I love it when he really canes me hard enough to leave marks for a week or so and my ass is on fire when he fucks me. The adrenaline rush with the orgasm is incredible. He even brought a friend over once and they both caned me and double teamed me. I loved that.

One day when we were cuddling after sex and I had my head nestled into his chest as I played with his soft cock we started talking about fantasies. He confided to me that his favorite fantasy is being caught jacking off by his mother and it leading to him fucking her. He said it had started when he walked in on his parents having sex and his mother was taking it doggy style and screamed his fathers name when she came. I had seen a picture of her one time when I met him at his office to blow him. She was quite attractive so I could see why he would want to do her. He knew it would never happen though; she was just too much of a prude for that. He asked about my fantasies and while there are a lot of them but there is one that I have had for a while and had been thinking about a lot. It is to be brutally raped by a big black man with a big cock. He would choke me and slap me and bend me over and brutally spank or cane me before pounding me relentlessly.

I wanted to do something special for Ken so a few weeks later I decided to role play his fantasy for him. I did not tell him about it. I bought a wig styled like his mother's hair in the picture I saw and bought a dress as close to the one she had on. I called Ken before our date that Saturday and told him I had a surprise for him. I told him to just walk in when he got there, get naked and wait for me on the sofa. He agreed so Saturday evening I got ready for him. I put on the dress which was a plain red dress with gold buttons down the front. It came down to my knees and had a high neckline that showed no cleavage. It was very unflattering but it did make me look like his mother, especially when I added the tan hose, the conservative looking red pumps and the wig I had bought. I finished up by doing my best to go light on the make up. I actually had to take it all off and start again once. I'm just too used to being a slut. By the time I heard Ken come in I was ready. I waited a while for him to get comfortable while I adjusted the dress, wig, and checked my make up. I had even bought perfume I thought an older woman might wear and sprit zed some on before I was ready to join Ken.

I knew with Ken being naked on the sofa alone with porn playing he would have his cock in his hand so I had waited long enough to make sure before flinging open the door and bursting in on him.

"Just what the hell is going on here young man?' I yelled.

He was truly shocked at first and yes I was right, he had his cock in his hand and it was hard already. He gave me a quick smile to let me know he understood before covering his junk with both hands.

"I was just..."

"I know what you were JUST doing son and its perfectly natural for a boy to experiment. I just don't really appreciate the nasty video you're using to fuel your interest though. Where did you get this filth anyway?"

"I, I, I got it on the internet. It's not hard to find."

"I guess that's true.' I said and then sat next to him and put my arm around him and pulled him into me. I started telling him how it was OK to masturbate and how good a son he was while lightly strumming his chest with my fingernails. As I continued talking to him I let my hand wander from his chest down to his cock. I lightly scratched up and down its length with the tips of my nails feeling it jump each time I would stop and then restart. Before long I was stroking his cock in my fist and telling him that his first time with a woman should be with someone who loves him and knows what they are doing. I went on to tell him that it's OK for a mother and son to have sex and actually it was a natural thing for a boys mother to be his first. With that I took his cock in my mouth and gently started sucking it while lightly scratching his balls with my nails. I sucked him for a while then took him by the hand and led him to my bed.

We stopped just inside the bedroom door and kissed passionately as he started undressing me. When he had me undressed I lay on the bed on my back and had him take me missionary style. I pulled him down to me and kissed him deeply while scratching his back up and down with my nails while telling him "Fuck mommy baby, you're such a good boy and you fuck mommy so good!" He fucked me gently and deeply until he shuddered and emptied his seed deep inside me. It was the most gentle, passionate, sensual fuck I have ever had and I may have accepted had he asked me to marry him right then.

After his cock softened and slid out he rolled off me and we cuddled and kissed while I played with his cock and balls. Before long he was herd again and I took him into my mouth. I really worked him up, bringing him to the edge time and time again before stopping, denying him his second release. When he had enough he took control lifting me up and putting me on all fours. He positioned himself behind me and rammed his full length in all at once. He began pounding me furiously and the whole bed shook with each stroke. After pounding me for about 30 minutes or so we were both covered in sweat and I could feel both of us getting close. I started yelling "fuck mommy! Fuck mommy good baby! O mommy loves your cock. Fuck meeeeee." When we both were cumming I screamed "Oh Ken! Oh Ken! Oh fuck me Ken!" He came deep inside me as I wet the sheets beneath us with my cum. I don't think he had ever cum so much before, when he pulled out a river of cum started oozing out and down my taint onto my balls. I love that! We cuddled for a while and he thanked me for getting him as close as he would ever get to really having his mom. I was happy to have pleased him so much. I kissed him goodnight and he went home. I lay there before going to sleep and thought abut how far he had come. I had taken him from a bumbling fool blindly stabbing at my guts that first time to a gentle, passionate, and skilled lover. He knew how to touch all the right places with each stroke of his cock and had learned to make me cum almost on command by slapping my ass or tweaking a nipple at the right time.

Life went on as usual for a while after that with us getting together couple of times a week to fuck and I had all but forgotten about sharing my fantasy with Ken. One weekend he called and asked me to meet him at a motel near his house because he really wanted to fuck but did not have time to drive to my house. I was OK with that, we had done this before, the motel was a nice one and I kinda looked forward to getting away for a night.

He got me a room for that Saturday and I arrived early at about 3PM. I took my time and waxed all my hair off and took a bubble bath. I dressed in my school girl uniform which was so slutty looking no school in the world would allow it. It consisted of a very short plaid skirt which showed off the bottom of my ass, a white top that tied just under my breasts, white fishnets and black Mary Jane style heels. I had a shoulder length black wig and of course too much make up.

I lounged around and had a few drinks to loosen up while I watched porn on TV and surfed the net and chatted with online friends. Our date was for 7PM and he was right on time. I heard a light knock at the door about 5 till. I peered through the little hole in the door and there was Ken. I smiled as I straightened my wig and licked my lips ready to give him a big ole kiss when he came in. I went to open the door and had gotten it open just an inch or two when someone violently forced it open nearly knocking me down. I looked up to find a huge black guy in dreadlocks rushing at me. He grabbed me, spun me around, and wrapped a huge arm around my neck putting me in a choke hold. He grabbed my arm and forced it behind my back. Someone else, Ken I assumed forced my other arm behind my back while a third person put a blindfold on me. A ball gag was forced into my mouth, my top was ripped open, and metal clamps were put on my nipples. The clamps hurt like hell and I knew my nipples would be bleeding or at least bruised. Tears were welling up in my eyes as I heard the door being locked.

Once the door was locked the big one released me from the choke hold and spun me around. He slapped me on the face with an open hand then backhanded me even harder. He then threw me down on the bed face down. Three sets of hands grabbed my arms and legs and spread them apart. Shackles were placed on my wrists and ankles and chains were fixed to the four corners of the bed. I was chained tight and could barely move an inch or two in any direction. My skirt was pulled up and bunched around my waist and my thong was ripped off my body. Then I felt a big rough hand caressing my ass cheeks and a big finger teasing my rosebud. It started feeling good and the pain in my nipples had subsided a little and I started enjoying it.

As soon as it started feeling good the hand stopped rubbing me and "smack" hit my ass so hard I cried out behind the ball gag. Then "smack smack smack one after another. I was being spanked hard. Every ten swats or so he would stop and rub my ass cheeks which were getting warmer and I'm sure redder with every swat. This went on for quite some time and I must have received 100 swats before I got a break. I was beginning to calm down when I heard the swoosh of a belt being removed. Before I could realize what was happening "crack" the heavy leather belt was brought down on my ass. Then crack crack crack until I was crying from the intense pain. He smacked me with the belt time and time again as I counted 10 then 20 then 30 without stopping. As he neared 50 I thought I would pass out and finally he stopped. I was surprised to hear a female voice commenting on how he had drawn blood. It seemed surreal to me. The intensity of the beating had so much adrenaline rushing through my blood that I had a huge rush going.

The chains on my legs were loosened a bit to allow someone to slide two pillows under my hips to elevate my ass. I felt the big guy get on the bed between my legs then felt him spit on my rosebud. I heard him spit on his cock then felt his huge head rubbing around my hole.

"Listen bitch, I'm fixin to fuck the hell out of you and it's going to hurt either way. You best just take what I got to give you or it'll just hurt more." He said before forcefully ramming his huge cock into me. The pain was almost unbearable as his fat head cleared my outer ring and plunged deep into me. I was so glad that I had squirted some lube in there after my douche. He pulled back and rammed again and again going a little deeper each time until I could feel his course pubic hare touching my ass. The pain was incredible at first. He was going so deep I thought I'd feel him at the back of my teeth any moment and whenever his hips slammed into my tattered ass cheeks it hurt even more.

He held himself up with one hand and used the other to wrap around my throat and choke me as he pounded me brutally. The bed shook with each stroke and I thought he might break my back he was pounding so hard. Eventually the pain started to subside and it started feeling good. It still hurt like hell but in a good way. Gene got on the bed and lifted my face up so he could shove his cock in my mouth. He held my face up and started fucking it hard. I was getting pounded from both ends and loved it. After another 20 minutes or so of pounding Ken howled as he filled my mouth with sperm. This must have done something for the big guy because he tensed up and filled my ass with his sperm. He let his cock go soft and pulled out. He took Ken's place and told me to clean him up. I licked all the cum off soft cock which was still huge even when soft. I was left to recover while I head them opening beers and laughing. My asshole must have been hanging wide open and a little cum had begun oozing out. I guess the big guy had pumped me full of air because a minute later I let out a big wet fart and sprayed cum all over the bed. Ken and the other two burst out laughing at this. I have to admit it must have been pretty funny.

They had a beer or two while I recovered then they turned me over and chained me to the bed again. I was spread eagle in the same position except face up. The ball gag and blind fold were removed and I could finally see that there were three of them in all; the big guy, Ken, and a nice looking black girl who couldn't have been much older than 18. She removed her panties which was all the she was wearing and stood above me on the bed with one foot on either side of my head. I had a clear view of her pussy and asshole from this angle; she was nicely trimmed with big pussy lips and clit. Before I could wonder what she was going to do she started pissing on my face. I opened my mouth and started swallowing her pee as fast as I could.

"That's right bitch, don't you miss a drop." She shouted.

When she finished pissing she squatted and pressed her asshole to my lips.

"That's right bitch, I just took a shit and didn't wipe, you better clean me up good if you know what's good for you!"

I licked her ass, taint and pussy until it was clean and she stood up and jumped off the bed. I was then unchained, stood up, and bent over the bed. My legs were chained to the foot of the bed and my arms were raised above my head and chained together. Ken got on the bed and straddled my face again and I started sucking his cock. I was so focused on sucking him I didn't notice that the big guy had walked around behind me with a cane. The first blow caught me by surprise and I almost bit Kens cock. He gave me about 20 hard swats with the cane and I almost passed out before he stopped.

Ken got off the bed and came around behind me. He slid his now hard cock into me and started fucking me good. I looked over and the black girl was giving the big guy head, his huge cock was starting to get hard and growing bigger and bigger in her mouth. It looked like she was sucking off a horse. About the time she had him fully hard I felt Ken release a load in my ass then pull out. The big guy then came up and shoved his monster in me to the hilt. Once again he brutally fucked me smacking my ass every few strokes which hurt like hell. This time when he was ready to come he had the girl unchain me and put me on my knees in front of him. He fed me his monster cock which I could barley fit in my mouth. About all I could fit in there was the head. I used both hands to stroke his anaconda while sucking the head until he let loose his seed. I swallowed every drop and licked him clean.

They left after that and I went to the bathroom to run a hot bubble bath to recover in. I looked at my ass in the mirror. This was definitely the worst ass whipping I had ever gotten. It had already started to turn black and there were several stripes that had been bleeding. I was just getting in the bath when someone knocked at the door. I looked through the peep hole and saw that it was the young black girl. I opened the door cautiously this time and to my relief she was alone. She had a small bottle of Cognac in her hand and said she had nothing to do the rest of the weekend and thought I might need a little company. She pulled a joint from her purse and smiled. Cognac and some weed sounded good now so I let her in. I told her I'd join her after my bath then went to the tub and slipped into the warm water.

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