Fucking My First Tranny - Fun Times With Jennifer free porn video

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This happened about a month ago, it was one of those days where I felt really horny so I had to do something about it and I just didn't want to fuck a woman this time. I've been really curious about trannies for a while now, I once fucked a friend of mine when were fooling around (I should write a story about him too!), but the combination of tits, smooth ass and a cock would always catch my interest and would get me really aroused every single time I thought about having sex with one.

A little backstory to this before we go any further...

Through this bullshit dating site I came across a trannie who showed some interest in me, so after a little while I finally convinced her to go to a hotel with me but she backed down on me and on top of that she also wanted to go dressed as a boy, so that was a bust.. well fuck!.

But then I found another tranny and was she a cutie! She goes by the name of Jennifer, she has long dark hair, petite body, kissable lips and the attitude that goes with those attributes. She's really polite and expects that you treat her the same way, she's also very straight forward with what she wants and what she wants is to have fun with with you and your dick inside her ass, simple terms right?. It only took a little small talk to get her phone number and that same day we set everything up to meet each other and have some fun at the hotel.

I was nervous but really excited about what was going to happen, she took longer than expected to get ready and get her cab so I kept wondering if she was really going to show up, I already had a backup plan in case it was yet another let down and sadly, plan "B" involved calling a woman, but then she calls me and tells me she's outside the hotel entrance, I wait until she arrives and there she was, greeting me with a lovely smile, hot red lips and she was dressed up simple: tight jeans and blouse.. like a lady!

I could feel my dick getting hard at the sight, that ass looked hot. The moment we enter the room she comes up to me and gives me this sweet kiss on the lips, her perfume was intoxicating and my dick was really hard with that alone!.

She slowly takes off her jeans, blessing me with the sight of that brown bubble butt covered with a little g-string and you could see the little bulge between her panties, I couldn't stop myself so I start kissing her ass and give her a little lick on her asshole, she undressed completely and asks me to do the same and I gladly comply.

As I laid in bed, she starts to caress my balls gently and puts my dick in her mouth while she gets on all fours.. like a cute little whore. Her ass points at me so I tell her to put it closer to my face and as she continued to suck me I could lick her sweet asshole and man, what a delicious smooth ass. I slowly push my tongue inside her and the taste of it drove me insane, I kept pushing my tongue inside, moving it sideways, tasting every inch of her ass.

My hands were stroking her dick and balls; just thinking about it makes me hard again. I stopped licking inside her hole only to move her dick and put it inside my mouth while I slowly put my fingers inside her asshole, I really enjoyed it and so did she, her moans were soft and asked for more. We kept sucking each other until I had to stop her for a moment so I could put the rubber on and she gets into position. Her curves and that perfect ass up just begging to be fucked were a delicious sight so I had to give my girl what she wanted.

As my dick was sliding slowly inside that tight asshole I could hear say "oooh" very softly and she grabbed the sheets while I pushed it all the way inside her and started moving slowly at first, then pumped a little harder. I'll never forget how she closed her eyes and bit her lips, she was loving it and I was loving that too. I start fucking her harder and her moans were growing louder too. Then she lays her body completely in bed and asks me to lay on top of her so I could go deeper. My cock simply disappeared inside her and I started fucking her harder and deeper, her moaning, how her body was moving with mine.. I couldn't hold it anymore, I came harder than I had ever come before and I didn't stop until I felt i couldn't come anymore.

But when I put my dick out.. surprise motherfucker! the condom got loose inside her asshole and cum was dripping everywhere, I thought I was in trouble and she was going to get mad at me and leave; I apologized to her and the only thing she said after giving me her lovely smile once agan was "It's ok baby" and she gives me a very passionate kiss and goes to the bathroom to clean herself up.


When she comes back we start talking for a little while, getting to know each other better, holding her in my arms, both naked. She tells me she’s a hair stylist and we chat a little more, as you can imagine, holding that hot naked body in my arms while I caressed her ass and felt her perfume wasn’t going to kept me down for long, she gets more tender with me and starts kissing me, moving her tongue inside my mouth, sucking my lips. It felt so good… I make her lay back and I start sucking her cock, getting it deep inside my mouth until I gag a little, I was thinking about making her put that fat cock inside my asshole, but I’m a virgin there and this time I wanted to be the only one doing the fucking, I make her get on fours and push my cock inside her and she lets out another “oh!” I pump harder and harder, watching it go inside and out of her ass made me feel so good. She tells me to stop and makes me lay in bed and she gets on top of me, pushes it inside her again and starts riding hard me like a girlfriend would ride you. I loved seeing my cock go deep in her as her cock moved on my belly, she closed her eyes and moaned harder and harder… it didn’t take long to make me cum and when I came she stroke her cock hard until she let that hot, sticky load on my stomach… one of the best days ever!
This story may be a little longer, but It was a tremendously erotic experience for me and I wanted to share it with you, I’ve been thinking about calling her again for another meeting and maybe this time I’ll let her fuck me and if she agrees, she’ll take pics as she takes my virginity. What do you guys think, should I do that?

Here are some pics of her, am I lucky or what?

http://s20.postimg.org/ysziusy4t/intima.jpg">

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~~~ Since I lost my virginity to a couple I met on Craigslist (read my past story) and I not only had a wonderful time, but got paid as well, I decided to post my own ad on Craigslist. It was a simple ad, a tranny in Toronto looking for fun time. He saw my ad on Craigslist and decided to message me to see whether or not we could get together or not. His name was Marc, a young black boy who lived in Scarborough. He said he was a shy guy, a virgin, and he watched a lot of tranny videos...

2 years ago
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Alan Gets A Tranny

-------------------------------------------------------------------------- I went to Alan's house after work one day to talk to him. His mom was single and she need a male figure to discuss masturbation since she had caught him doing it. I rang the bell. I heard footsteps on the stairs and then the door opened. "Hi Alan." "Oh, hi Mr. Jones." “Can i come in?” “Sure,” he said holding the door open. “Alan I have to be home soon, so let me just say this quickly: I know your mom caught...

3 years ago
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My Tranny Teacher 4

This is a fantasy story. Every day left me feeling more horny and excited for our next tutoring session with Ms. Bennett (Becca). I was hard about 90% of the time just going thru all of my special clothing and deciding what I could get away with wearing to school that would light up my teacher and make her clitty into a full stiff dick that I could put to use. After looking at everything I decided that black lace top stockings would be exciting and could not be noticed under my school clothes....

2 years ago
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Tranny Arschfick in der Jugendherberge

Fabianes ersten ErfahrungenFabiane, die ursprünglich einmal Fabian hieß, war eine Tranny und hatte gerade ihren 20. Geburtstag gefeiert. Sie war Berufsschülerin. Als solche übernachtete sie regelmäßig die Woche über in dem Hotel, in dem ich an der Rezeption arbeitete. Dieses Hotel war zwar an sich eine Jugendherberge, aber ganz im Stiele eines Hotels. Somit hatte ich mit vielen jungen, coolen Menschen zu tun. Mit einigen entwickelten sich manchmal Freundschaften, so auch mit Fabiane. Sie kannte...

3 years ago
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Trucker the Tranny

Jermaine Simpson drove his white 2010 Peterbilt raised-roof big rig into the truck stop just outside of the city. He called his friend, Mariah.“Hey, baby,” the dark-skinned transsexual answered.“What’s up boo? I’m at the truck stop,” Jermaine shared.“Okay, oool! I’m on my way.”“Awesome! Can I get a shower at your house?”“Of course!”“See you in a few.”“Bet!”Jermaine’s nine-and-a-half-incher was already hard. He loved fucking her whenever he was down this way. Once he had taken her on a six-day...

4 years ago
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BuildaTranny

Garvey Williams kissed the pretty, effeminate, white boy he had had been secretly fucking since they were high school sophomores. Back then, Garvey was a standout wide receiver with high prospects of moving on to Division One. He had progressed as everyone thought and Jamie Collier, the femboi, followed him to the large state university. Garvey and the Mustangs earned a national championship his junior year. The football prodigy decided that he should enter the NFL draft immediately following...

4 years ago
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Tranny Night

Tranny Night: My name is Andrew and I had known Jane since we were very young. She was a precocious child and could play piano and read music from a very early age as well as reading complex novels when most children our age were struggling with reading Enid Blyton novels. I was the brightest boy in our class and would have liked to pretend I was the brightest pupil in the class but Jane's results were always better than mine, although I would not admit it as she was a girl. As...

1 year ago
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Trained by The Tranny

I have always been considered a strong athletic straight black man. I have fucked a plenty of women being an executive in a high profile position. I had everything a man could ask for Power, Property and Plenty of Pussy. Well in life, all things change. I had just landed another two million dollar client and was out celebrating with friends over a local bar. I was feeling real good and I never believed in going home alone…..so why should tonight be different. Then after a few or too many drinks...

She Males
3 years ago
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An Evening with Gloria and Jennifer

After the costume party at Tom and Gloria’s house, Jennifer, Jerry and I both rested quite well that Sunday afternoon, good weather and all. Monday at work was a grind and I occasionally let my mind wander to the events of Saturday night, eliciting a smile or a grin at times. I decided to skip happy hour Monday evening and headed home from work. I wasn’t in the door five minutes when the phone rang. It was Jennifer and she wanted to drop in for a few minutes to chat. I definitely had no...

Group Sex
3 years ago
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Jennifer

Jenniferi. The a*****ionJennifer walked slowly back to her dispatch area. When she got back to the office, all of theother runners were out. Jennifer sat down at the table and pulled out her MCAT study guideand began immersing herself in preparation for the upcoming test. Jennifer had alwayswanted to be a doctor. She had already completed a degree in Chemistry with a minor inBiology and was going to become a doctor. These few facts made her feel superior to mostof the uneducated people she...

4 years ago
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Jennifer

Jennifer was an attractive girl. She was 5’ 3" and weighed about 110 pounds. She was admiring her naked body in the mirror of her room. She had a reasonably shapely body for a 17 year old girl. Her brunette hair hung down to her shoulders. Her breasts were good sized, about a c cup. She didn’t like her legs; she felt they were a little to short. She felt her greatest asset was her ass. She turned to look at it. It was well rounded and firm. It had kind of a heart shape to it. She turned back...

1 year ago
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Tranny Night Out

Tranny Night Out and One Kinky SessionGuess I should start by explaining myself, as a young guy I always knew I was not the same as a lotof my friends and enemies for that matter, girls had no interest in me at all apart from ones who werelong term friends.I knew something was wrong but never worked out what it was till one evening whilst dating a girlnamed Becky I had met on an online dating service who seemed to accept me for who I am.We had been dating for 3 months or so and I always loved...

2 years ago
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Jennifer

Jennifer a slow starting tale of how a young graduate finds her place in society. Any similarities between the characters or corporations depicted here and any characters or corporations which actually exist is entirely unintentional.Part One.Jennifer walked slowly down the long brightly lit slightly curved corridor of the Walthers building looking for Mike Gordon's office, it was almost ten thirty on her third day at Walthers and Walthers. and her first day working as Mike's PA her first job...

1 year ago
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A Wylde Knight for Jennifer

This tale is the combination of a crime drama, romance story and good ole' hardcore sex. Like most of my stories, it is also quite long and detailed. But for those of you Kind Readers who appreciate my work, I think you will truly enjoy this one. So, without further ado, I present to you..... A Wylde Knight for Jennifer The Sun was just starting to rise on that March Sunday morning as I got quietly out of bed. I did not want to disturb the lovely young woman sleeping beside me....

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