My First Encounter With A Tranny : Part 2 free porn video

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We laid there touching and feeling each other’s naked body as my wife dropped her bags and said “seems like you two were having fun”. I introduced her to Judy who patted the bed and said “why don’t you come join us?” I will, let me freshen up first said my wife. Now my wife is one hot piece of ass, she’s about 5’1 and weighs about 160, on a count of her double D boobs. Her long beautiful hair reaches down to her butt, and she has a very pretty delicate face. Her best feature I would have to say is her fat pussy, and once wet its even better. My wife returned from the shower wearing only a black bra and black panties.

By this time Judy had put her panties back on and was anxiously waiting. “I’ll be right back” I told them, as I hurried to the bathroom to wash up to get ready for the next round. When I returned I found my wife and Judy making out and grabbing each others breast. Judy sucked on my wife’s tits while she inched her hand lower and lower till she was rubbing on Judy’s crotch. I stood at the foot of the bed in awe, watching my wife explore this sexy tranny’s body with her hands. Slowly, I slipped into the bed behind Judy and began rubbing my cock against her ass. This gave her a hard on that made my wife kiss down to her tits and kept going down till she was at her crotch.

She moved the panties aside and out came her massive cock, throbbing for more sexual pleasure. My wife licked her lips and said “mmm, what a wonderful cock you have”. She started sucking Judys dick while I kissed the back of her neck and rubbed my cock in between her butt cheeks. I looked and moaned as I saw my wifes head bobbing up and down on Judy’s delicious cock. I moved her hair out of the way and unclipped her bra to unleash her huge tits. She then put Judys wet dick in between her tits and started stroking it, making her moan in ecstasy. With one swoop, I moved Judy on top of my wife and soon she had my wife’s panties pulled to the side and was licking her pussy. They were in a 69 position when I got behind the sexy tranny and slid her panties down. I slid my cock inside of her ass yet again and began pounding her sweet ass while she ate my wife’s pussy.

My cock slid in and out while underneath my wife sucked on her big juicy dick. I pounded harder and she moaned louder and louder. We stayed in this position for a few more minutes when my wife said “I want to get fucked too”. With that I slid my cock out and laid back as I watched them sit up on their knees and pull down each others panties. Judys fat cock flung up and my wife caught it and started stroking it. She then got on her hands and knees and started sucking my cock as Judy positioned herself behind her and started fucking her doggystyle. “Oooh, that’s it, slide your big dick inside of me and fuck me like the whore I am” moaned my wife.

She sucked off all the juices off my dick while she got rammed hard. I held her head and watched her pretty face work my cock while hearing the sound of balls slapping against her ass. “I want to see her fuck you too” she said. “Okay, I said willingly, lets do it”. I crawled and wiggled under my wife in a 69 position and started eating her wet pussy. Then Judy picked up my legs and started fucking me harder than before. Her hard cock slid in and out of my wet ass, making me enjoy it more and more. She kept polishing my cock then she would take the cock out of my ass and would suck it and put it back in.


The feeling was so intense, I loved every minute of it. After a few more minutes of intense ass fucking, my wife said “now I want both of your cocks in me at the same time”. So I got up and we shifted around to where my wife laid on her side and I was behind her. I slid my cock up my wife’s tight ass as Judy slid inside of her fucked my wife simultaneously and she loved it. “Yes, fuck me good, fuck both of my holes, ohhh yesss” she moaned. I held her tits up for Judy to suck them as she fucked her nice and smooth. My cock throbbed inside of her tight asshole, I felt that I would cum too soon so I slowed down.

Then I pulled out and my wife got up so Judy could lay on top of me in a 69 position. She grabbed a hold of my cock while I got a hold of hers and we sucked each others dicks so good. My wife got behind Judy and began licking and eating her ass as she fucked my mouth. Judy released my cock and moaned as we feasted on her delicious body. “Give me some of that ass, I said to my wife, dropping Judy’s cock from my mouth. We all three got up and shifted positions, yet again. My wife laid back against some pillows while Judy stood over her and rammed her dick in her mouth. I watched my wife lick that juicy, wet cock all over as she enjoyed it. I got on my knees and spread Judy’s ass cheeks.

With my tongue out and stiff, I dug it inside her sweet, juicy ass. The feeling was sensational, so hot and erotic I almost came just by eating here there. I tongue fucked and ate Judys ass while my wife feasted on her cock as she held on to both of our heads. “Oooh, yeah, thats it, eat my ass baby, lick my ass while your wife sucks my dick, oh oh oh!” she moaned. I was overwhelmed with excitement not knowing what to expect next. Just then she pulled her cock out of my wifes mouth and brought it down to her tits and began to fuck her big tits while her ass bounced in my face. I sat up on my knees and slid my cock in her wet ass and started fucking her holding on to her hair. Her moans were erotic as she yelled “oh yes, fuck me, fuck me, fuck me hard baby, mmmmm, oooooooh”. I pounded her sweet ass till she couldn’t take it anymore, “Im about to cum”.

I pulled out and grabbed her hard cock from in between my wife’s tits and started jacking her off near our lips. My wife and I kissed and licked her dick as she shot her cum onto our mouths, we licked it all up and even swallowed it. Just after she was done shooting her load we tongue kissed and shared the cum. Judy fell back, spent, but with a hard on still throbbing for more. My wife straddled me and rode my cock while her ass bounced up and down. Judy started eating her ass then began tongue fucking her too. That’s all it took to make my wife have multiple orgasms, as her body quivered on top of me.

As my wife finished squirting the last drops of cum she had left in her, Judy’s tongue circled her asshole and she shuddered. My wife got off and let Judy sit on my hard throbbing cock that was anxious to blow. She rode me up and down while her cock flung in the air. After a few more minutes of this she said she was about to cum again so I made her get up and 69 with me again. We rolled over and now I was on top of her as we held on to each others cock in our mouths. We both sucked and licked each others hard dicks then I felt moisture in my ass. My wife licked my ass while Judy and I 69’d. Just then Judy stopped sucking and said “I have an idea”, she got up on her knees and stroked her cock.

She instructed my wife to lay on her back and made me climb on top of her with both of my knees on either side of her head. Judy then pushed my body forward so my cock was in my wifes face but at the same time my ass was high and in position. She slid her thick cock inside of me again and started fucking me harder and harder till my dick was slapping my wife in her face. My wife sucked my dick while I got pounded from behind. At that moment, Judy grabbed my hips and moaned as she let off another load of cum deep into my asshole. The moistness and feeling of her cum inside of me made me cum and it shot out all over my wife’s face.

She licked and swallowed all of my cum and we all three fell to the bed exhausted. Our first time experience proved to be one we’d never forget for my wife and I. Till this day we go to clubs in search of new Trannys to bring home and play with all night, marking the beginning of a new trend.

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-------------------------------------------------------------------------- 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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My first tranny girl experience got me hooked

I have always wanted to have sex with a tranny. I find these women sexy. In my daily life I dont know any, so I look online find a tranny to fuck. As I look online I find a sexy Cuban t-girl advertising sex. I instantly give her a call and arrange a time to go meet. One thing that turned me on is that she just moved from Cuba and had an spanish accent that turned my dick rock hard. Once I get to her home she leads me to the bedroom. She is 5'5 about 125 pounds. My girlfriend is 5'9 160. So my...

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
4 years ago
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First time with a tranny I met on grindr

This is a true story. I am a straight acting 23 year old, 5ft 10 and an athletic 160 pounds. To this point I've only ever been with one guy before in a wild, spur of the moment spring break fling but it had opened my eyes to a world I knew I wasn't finished with. I had joined the gay app grindr in search of a tranny to fulfill my fantasies and finally I found one!Her profile read "looking for a submissive bottom to be my bitch" it was just what I wanted! I eagerly messaged her but began to get...

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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My New GF has a Cock Tranny

I'm your run of the mill middle-aged white guy; divorced, decent job, plenty of hobbies, and your standard list of perversions. I love women. I love the way they smell, I love their bodies, I love their personalities, and I really love having sex with them. I've had a few bisexual encounters in my day, mostly back in college, and while I have no phobias about man-on-man action, I have never been attracted to the same sex. Although admittedly, the sight of a large, erect cock has always made my...

2 years ago
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Young Tranny Ch 6 Vegas Sugar Daddy Pt 1

Young Tranny Ch. 6 Vegas Sugar Daddy Pt 1.This is the first half of the sixth story following "How I Started," and shares my experiences between the ages of 19-29. These are prelude stories to the series of "Playtime Stories" I wrote. I hope you enjoy them and comment publicly or privately - it turns me on for some reason! These stories (especially this one) are mostly true so enjoy! I LOVE COMMENTS!!!!This pic is from around that time... enjoy!Over the next two years I worked and played in the...

3 years ago
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Advice for dating a tranny for the semistraig

I will apologize right of for the grammar etc. I am not a professional writer by any means. A bit of prep is in order here. As an adult no one really likes being told how to think or what to do, we have TV commercials for that. That said, as a "Gurl" I may have a bit of insight into why your long fantasized about date with a chick with a dick didn't go as you dreamed. I would also like to point out I am in no way an expert and I am sure my views will differ form other "gurls" so take it for...

1 year ago
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my first tranny pt 1

you always remember your first time. I remember my first blow job from an ex. (believe me, thats another story.) the first time I touched a pair of tits. the first time I ever ate pussy. the first time I fucked a woman in the ass. & I'll always remember the first time I was with a tranny.her name was brooke. I always wanted to be with a tranny because I was always curious. I mean, shes a chick right. but then she has a dick. you all know some trannies are drop dead beautiful. this one was....

3 years ago
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Abused as a tranny at a sex party with my mum

This story is a follow up to "Caught wearing my mother's stockings"I decided to go to the party and be the tranny slut they were looking for. After all, it's nice to be wanted and I really would do anything to keep those photos of me dressed in my mum's stockings, private from my friends.I've never had anything up my ass before, in fact I've never even had sex at all. This was going to be my first sexual experience. Unless you include being wanked off by my mum or kissing and groping fat girl,...

2 years ago
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A True Life Tranny Experience

My real name’s Benny, and I’m a 32 year old very passable bi transvestite that has an insatiable craving for receiving another guy’s cum. I’m 5ft 7in tall, quite skinny (10 stone ‘ 140lbs to you Americans), and have perfected the mannerisms of a ‘real’ woman in every way, without going over the top by acting too effeminate like some ‘Nancy-boys’ tend to do. That means that when I’m fully dressed and wearing my wig and makeup, I walk,...

3 years ago
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Tranny in Toronto Chapter 4 Valentines Day Threesome

Introduction: Message me on forums and tell me whether you like my story or not. Thanks. I wrote this story in an hour, let me know what you think about it. Have a happy Valentines Day. ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ Discreet Couple Lookn For Valentines Day Fun – mw4t (DownTown T.O) Wife and I want to fuck a lovely female tranny on Valentines Day. Must be bisexual, message me. ________________________________________ Hello, I hope...

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