My Date With A Tranny free porn video

This is a FigCaption - special HTML5 tag for Image (like short description, you can remove it)
I had been alone for a while and I was really horny. I am not the best looking guy but cute and a little over weight. I am 6'1" tall and about 280. So going to a bar was not going to work so I started to search craigslist for some one. I found a couple women but after emailing them I found out they all wanted me to join some web site and I was not looking for that. So I kept looking and I found a woman who was real and interested in me after we exchanged emails. So I set a date with her to get together and she was excited for it as was I. I went to her house to pick her up and she was beautiful. About 5'2" tall with a nice set of tits and a tight ass. I kissed her and helped her into my car. We went to dinner and had a good time talking while we ate. She was easy to talk to and I was really enjoying myself and she said she was too. We left and I asked her if there was anything special she would like to do and she said yes there is, She said she wanted me to take her home so we could sit and talk more and maybe more then talk. I thought this was going great so I drove to her house. We went inside and she told me to sit on the couch. She went into the other room and when she came back out she had some drinks for us. She sat beside me and we drank and talked more then I had to kiss her she was so sexy. I leaned in and kissed her softly at first but she started to kiss me harder. I was happy she seemed to want to do more so I kissed her more. After a few mins past I started to run my hand over her body and when I got to her tits I took one in my hand and gave it a squeeze and she moaned. I pulled her shirt up and off and kissed the top of her tit and caressed it through her bra. She was moaning and telling me how good it felt. I removed her bra and took one nipple between my fingers and squeezed it making her moan louder. I bent down and took that nipple into my mouth and sucked on it making it grow in my mouth. She held the back of my head and told me not to stop. I was not about to because she was so sexy and hot I needed to have her. I kept kissing and sucking her tits and slide my hand down toward her pants. She reached for my hand and stopped me. I looked at her and asked her why? She said if we go any further we need to talk first. I said ok and she pulled back and started to tell me that she was not like other women.
I said I knew that because she was so hot and sexy. She smiled and thanked me then said more then that baby. I asked her what she was talking about. She looked me in the eye and said I am not all woman I have something else in my pants. I looked at her and didn't say anything right away so I think she was getting worried I may be mad. I told her that I understood and I wanted to see it for myself. She looked at me and saw I was serious so she smiled and stood up. She slowly unzipped her shorts and pulled then down slowly. I saw she was not wearing any panties and when she got her shorts down enough her cock came into view with a pop. She was watching my face as she did this and I just looked at her. She asked what I thought and I replied that I thought she was sexy and hot and had a nice dick. It was not real big about 4" soft and cut with small balls hanging under it. She asked if I had ever been with a tranny before and I said yes and I had a very good time. She smiled really big and sighed as relief left her body. She asked me to undress so I stood up and took my clothes off. When my nice thick 7" came out she caught her breath and said that looks good. I thanked her and she took my hand and had me follow her to her bedroom. I loved watching her tight ass sway as she walked in front of me and my dick started to get hard. We got to her bedroom and she turned and kissed me then said she was so happy she had wrote to me because she was really horny. I said I was glad she did too and I was going to show her how happy I was. I picked her up in my arms and laid her on the bed. I climbed on the bed and kissed her our tongues dancing in each others mouth. I caressed her body as we kissed and when I got to her dick I rubbed it and felt it start to grow in my hand. She is not get real big really about 5" total but I still liked it. She was caressing my body and stroking my dick. She said she loved how big and thick my dick was and I kissed her again. I kissed down her body and when I got to her clit I stopped and looked at it right in front of my face. I was leaking percum and she was breathing hard. She said I did not have to do anything if I did not want to. I smiled and kissed the tip of her pretty little clit. (If you do not know tranny's like to call their dicks their clits and their ass is their pussy so I will be calling them that for the rest of the story.) I kissed the tip and she took a deep breath as I took her clit into my mouth and started to suck it.
It tasted good and felt so soft in my mouth. I sucked her clit slowly then a little faster. I sucked on it for a few mins then took it out and licked her balls. I took one into my mouth and sucked on it some. Then I took her clit back into my mouth and sucked it more. She was moaning and told how good it felt to have a warm wet mouth around her clit again and she was so happy I was into tranny's. I stopped sucking and looked at her and said I like trannys and sucking on a nice clit is fun. I moved up and kissed her and she kissed me hard and held me to her body. I went back down on her clit and took it into my mouth again and sucked her hard. I was running my hand over her legs and ass as I sucked. I put my fingers between her ass cheeks and felt her tight hole. I kept sucking her clit and placed a finger next to her pussy and started to push it in. She moaned loud and her clit got a little bigger. I kept sucking and fingering her pussy. I could tell she was close so I took my other hand and started to stroke her clit as I sucked her. With the finger in her pussy and my stroking and sucking her clit she came hard. I pulled my mouth off her clit when she started to come and let some of her cum hit my face then I took her clit back into my mouth and sucked her dry. I licked and cleaned her clit and balls then licked up her cum that had fallen off my face. I moved up and kissed her and she licked her cum off my face. She told me that was great and it had been a while for her. I told her I could tell by how much she came. She laughed and kissed me again. Then she got up and got me a drink and said it was my turn now. She crawled onto the bed between my legs and said she could not wait to taste my big dick. She licked my dick from bottom to top and smiled. I asked her what was she smiling about and she said I love the taste of a nice big dick and yours taste so good I am just happy to find someone who likes me enough to play with me so I am really happy right now. I smiled too and she took my dick into her mouth and start to give me the best blow job I have ever had. She sucked and licked my whole dick and sucked on my balls moaning how good it felt and tasted. I was so hard it hurt but I loved every min of it. She sucked me hard and played with my balls for a few mins and I felt myself getting close. I told her she was very good and if she was not careful I was going to cum. That seemed to stir her on and she sucked me harder wanting my cum so bad. It do not take much longer and I was cumming harder then I have ever cum before. She drank every drop of my cum and she kissed my dick.She turned her head to look at me and said that was great baby you taste really good I have needed a nice big load like that in my mouth for a long time. She moved up my body laying on top of me and kissed me again. We laid there just caressing and kissing some and she asked me if I wanted to fuck her pussy. I said yes and she moved down and started to suck my dick back to hardness. It did not take her long because she was so good and soon I was hard again. She moved up and kissed me and said to just lay there she was going to ride my big dick. She got off the bed and got some lube and put some on my dick and her pussy. Then she stood over me and started to place her pussy over my dick. She slowly started to slide it into her tight pussy and it took her a min to get the head into her pussy. Once there she held still and said it had been a while since she had a nice big dick in her pussy.
I told her to take her time because I was enjoying the tightness of her pussy. She smiled and bent down and kissed me and when she did more of my dick slide into her pussy. She was so tight it felt like I would never get it all in but after a few mins she did and she was sitting on my whole dick. She sat there and let us both enjoy the feeling then she started to slowly start to ride me. It felt great and I wanted it to last so I let her ride me some then I stopped her and lifted her off my dick and told her to get on her hands and knees. She did and I get behind her and slide my dick back into her tight pussy. I held her hips and fucked her hard. She moaned and said it felt great and to keep fucking her. I did because it did feel great and I wanted to fill her pussy with my cum. I reached around her as I fucked her and stroked her clit as I fucked her pussy. She was hard and leaking when I touched her and I knew she was going to cum soon. I was getting close to so I stroked her harder and soon I shoved my hard dick deep into her ass and came in it. As I shot my load deep in her ass she came too all over my hand and the bed. After I stopped coming I pulled out and we both fell onto the bed breathing hard. I kissed her and told her that was great baby and she said no it was fantastic. We laid there a while kissing and resting then I got up and dressed. She walked me to the door and I asked her if I could see her again. She said how about tomorrow night? I said I would pick her up around 8 for dinner and she said why don't we stay in and I laughed and said I like the way you think baby.

Same as My date with a tranny Videos

3 years ago
  • 0
  • 16
  • 0

SARAHS NINE INCH TRANNY

For the last week my man has been tempting me with images of hung trannys. They have an added dimension when it comes to sex - tits and a cock, preferably both in generous doses. By the end of the week I am hanging out to experience a new one. One of the images he showed me was a side on shot of a tranny in panty hose with her back to the wall flaunting a huge erection thrusting out of her panty hose that really piqued my already strong libido. Another was a pic of tall, slim tranny sitting...

3 years ago
  • 0
  • 27
  • 0

First time with a Tranny

Stevie had always found it relatively easy to get girl friends. Not all had been good experiences. He always felt that after sex he just wasn’t satisfied. Maybe he wanted something different. Some people are perfectly fine about being gay or bisexual, but for others, it is a scary mine field. Stevie was one of those people. People had commented on him being gay for years and he always felt ashamed. He denied it, of course, but as time went by the thoughts about the whole subject haunted him. He...

Gay Male
1 year ago
  • 0
  • 5
  • 0

My first but not last encounter with a tranny

My Wife and I have been married for about 3 years now and have since recently, been looking to have our first experience with a she male. I met a girl online name Judy and after chatting for a while and exchanging pictures we agreed to a meet and greet. Judy proved to be a very sexy transgender with feminine features. Her highlighted hair was long and she had size B cup breast with a thick firm ass and long pretty legs. She was very beautiful and had an awesome personality. We sat down and...

She Males
3 years ago
  • 0
  • 7
  • 0

My first time with a tranny

I always had a strong sex drive, and since I had been around 16 I had been turned on by gay porn. I must say that I am straight, well on second thought, better say that I am bisexual. And I always have and will like girls. But there is something about a cock that turns me on and I then discovered shemale porn. I think that a hot sexy shemale and a cock is the best combination there could be. I have a strange fascination with cocks and a hot sexy girly body tops it off.In August 2007 I was 24...

2 years ago
  • 0
  • 10
  • 0

My first tranny

I had never been with a tranny before and did not plan on being with one at all but you never know what will happen. I had a bad day, I had been in meetings all day with new clients in another city. I decided to stop for a drink or two before going back to my hotel room. I found this bar that look interesting so I went in. There were lots of beautiful women there so I thought that maybe I would get lucky and not have to be alone tonight. I went to the bar and ordered a drink and checked out the...

1 year ago
  • 0
  • 12
  • 0

Dream Tranny

Dreams can be strange, sexy things. Your wife may be a stunning knock-out, way the fuck out of your league, but I bet she ain’t your dream girl. No, your perfect fantasy angel has the big tits and pretty face you love so much, but she’s also got something extra: a big ol’ dick between her legs. Sorry, wifey, but tonight may be a good evening to spend with DreamTranny.DreamTranny.com is a site with history. They’ve been around since 2000, making them one of the older shemale porn operations on...

Premium Shemale Porn Sites
1 year ago
  • 0
  • 16
  • 0

First Time with Tranny

So this is the story about how I got my first experience being a bottom, and why it was with a tranny.I was 18 and wanted to try being a bottom. For a long time I had experimented by myself at home with different things (hair brushes handles, screw drivers handles, ping pong paddles handles etc...) but I really wanted the real thing. I had the fantasy about sucking dick and getting fucked. I had been watching anal sex porn, gay porn and shemale porn for a long time, and always I thought the...

3 years ago
  • 0
  • 6
  • 0

My first time as a bottom and with a tranny

So this is the story about how i got my first experience being a bottom, and why it was with a trannyI was 18 and wanted to try being a bottom. For a long time I had experimented by myself at home with different things (hair brushes handles, screw drivers handles, ping pong paddles handles etc...) but I really wanted the real thing. I had the fantasy about sucking dick and getting fucked. I had been watching anal sex porn, gay porn and shemale porn for a long time, and always I thought the...

1 year ago
  • 0
  • 10
  • 0

Fun with a latina tranny

So I'm a big fan of a big tranny cock in my ass. Just throwing that out there early on here.So this past summer I decided that with my school being off I should get some tranny cock as fast as I could. I went on a site and set up a new account, hoping for the same luck I had a few months ago with a hot black tranny named Jade and her friend. I quickly found a very nice 20 something tranny names Maria who said I would do. We went through a few chat sessions, with our cams on and I convinced...

3 years ago
  • 0
  • 11
  • 0

Couple Finds Another Plus Tranny

While I was in the military, there were many opportunities to see some of the wild and crazy sites and people of the world. One time in Japan a bunch of us in a mixed group (men and women) went to a show that featured transsexuals. These were men who now dressed and acted like women. All of the men/women featured had breast implants to additionally make you believe they were real. The show was very exciting with each of the trannies on stage showing us they were as good looking without their...

3 years ago
  • 0
  • 28
  • 0

Im a Meat Packing Girl Tranny

I didn't go looking for a tranny, shemale, dickgirl, or whatever derogatory term a homophobic world has labeled women that happen to be packing a penis. In fact, while I had messed around a little with the man worm, back in college and with a drunken buddy a few times, I considered myself 100% a hetero male, in love with the female form and a total horn dog for a beautiful woman. I must admit, I've jerked off more than a few times to shemale porn on my computer at home, wondering what it would...

1 year ago
  • 0
  • 10
  • 0

Revenge on a Tranny

Revenge on a Tranny My relationship with my partner Julie had been strained over the last twoof our ten years together. For a period of six months we?d stopped having sex.I thought she might leave me but I figured that if she was going to find anotherwoman then there was nothing I could do about it and besides, I had a womanor two I knew I could fall back on for affection if I ever found the need.I was a good lover, but there seemed to be something that Julie needed sexuallythat I couldn?t...

2 years ago
  • 0
  • 6
  • 0

First Time With Tranny

I had fantasized for quite a while about hooking up with a hot chick with a nice cock. I gravitated towards shemale porn and couldn’t get enough of it. On this particular day I was having a few drinks and browsing the web for my favorite shemale movies. I discovered the gay.com chat forum. Soon I was chatting with this hot asian crossdresser. She was about my age (21 or so at the time) and lived just a few towns over from me. We shared some fantasies and seemed to have a good connection. She...

3 years ago
  • 0
  • 8
  • 0

First Time With Tranny

I had fantasized for quite a while about hooking up with a hot chick with a nice cock. I gravitated towards shemale porn and couldn't get enough of it. On this particular day I was having a few drinks and browsing the web for my favorite shemale movies. I discovered the gay.com chat forum. Soon I was chatting with this hot asian crossdresser. She was about my age (21 or so at the time) and lived just a few towns over from me. We shared some fantasies and seemed to have a good connection. She...

1 year ago
  • 0
  • 12
  • 0

My first time with a tranny

It happened on a Monday morning. After waking up with a throbbing hard-on. I called up my regular booty call. But she couldn't make it. Because her husband stayed home from work that day. So I decided to browse Craigslist, looking for someone local. After posting my ad, looking for NSA sex. I sat back and waited. Within minutes, I received over a dozen new messages. But none of them really appealed to me. Then after a few hours of receiving numerous messages, from both women and...

1 year ago
  • 0
  • 11
  • 0

Fun Time With A Top Tranny

So since I got a good rating for my first sex story, I shall write another one about my first time with a tranny. This happened last year. She was 25, and I was 21. So I am Ash, I am 22, I pretty good and masculine looking. I am mostly a bottom though. I have always been a huge fan of shemales and ladyboys. Respect them and also lust for them :p anyway, so I was in dubai last year and I thought that there might be much more shemales and easier to meet since the place was quite forward with a...

Gay Male
2 years ago
  • 0
  • 8
  • 0

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
  • 0
  • 20
  • 0

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
  • 0
  • 13
  • 0

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...

1 year ago
  • 0
  • 14
  • 0

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
1 year ago
  • 0
  • 21
  • 0

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
  • 0
  • 4
  • 0

beautiful tranny

This guy picks up a girl and takes her to his place. Can you imagine his surprise when he finds out that this girl has a dong?Hi! My name is Andrew! I’m a 5.4 feet tall, with some cute beer belly, crew cut light brown haired guy, blue eyes. My friends say I have a big noseJ but it’s not that I should worry about! Men of my family have always been stocky, and thickset. So a big nose and stocky figure are not a trouble! I’m working in a Western City College as a tutor of English Literature. I...

1 year ago
  • 0
  • 11
  • 0

My beautiful tranny

This guy picks up a girl and takes her to his place. Can you imagine his surprise when he finds out that this girl has a dong?Hi! My name is Andrew! I’m a 5.4 feet tall, with some cute beer belly, crew cut light brown haired guy, blue eyes. My friends say I have a big noseJ but it’s not that I should worry about! Men of my family have always been stocky, and thickset. So a big nose and stocky figure are not a trouble! I’m working in a Western City College as a tutor of English Literature. I...

4 years ago
  • 0
  • 7
  • 0

First tranny

I’d been single for a few months and having the shittyist of luck on dating sites. I was unemployed and making some deliveries to the gay community for some extra cash. One of my regular stops was to a tranny named Tory she wasn’t bad looking and she never made a move on me other than asking if I’d like to hangout for a few minutes. Anyway I’d seen her on one of the chat rooms on a dating site... now I’d been without sex for at least a few weeks and I got a little curious. I started...

1 year ago
  • 0
  • 7
  • 0

FIRST TIME TRANNY

It was pretty dingy in here, the sunlight came through a old dirty high window and a single fluorescent tube did little to lift the overall gloom. An oppressive smell of stale piss also hung over the whole place. What was I doing in here? In truth I did not know but I was 16, horny and wanted to find out about the rumours about sexual activity. I was still a virgin and although had messed around wanking at home, I was very naïve. I walked into the last cubicle, shut and bolted the door, took...

2 years ago
  • 0
  • 6
  • 0

my first tranny

[i[/i]im donnie, i had just dropped my girlfriend of at shipyard to work graveyard shift. i wanted to have a drink in bar, not a beer in a parking lot. as i drove toward the bridge i saw a cocktail sign, u know a cocktail glass. so i made my way to that street and pulled up in front of "the black rose". i went in and sat at the bar and ordered shot of jack and a bud. ik looked around and thought i died and went to heaven. all i saw was tits and leg and pretty women. i was enjoying the view...

2 years ago
  • 0
  • 7
  • 0

FIRST TIME TRANNY

It was pretty dingy in here, the sunlight came through a old dirty high window and a single fluorescent tube did little to lift the overall gloom. An oppressive smell of stale piss also hung over the whole place.What was I doing in here? In truth I did not know but I was 16, horny and wanted to find out about the rumours about sexual activity.I was still a virgin and although had messed around wanking at home, I was very naïve.I walked into the last cubicle, shut and bolted the door, took my...

2 years ago
  • 0
  • 9
  • 0

My Frist time with a tranny

My Frist time it was back when AOL frist came out. I was in a miami chatroom and I met a tranylicous. We Started to chat. I remember going to the profile on the side of the message window and I found out throu pics what a tranny was. I must of been 13 at the time or so. She gave me her address. it was not to far from Downtown so I head over to meet her as I smoked a joint. She had a nice apt, pretty empty She had just moved from Ny. After a little chat we had that helped me relax She came...

1 year ago
  • 0
  • 9
  • 0

first time with a Tranny

My first tranny I had was back after I graduated from high school. I was working with her/him at a Wal-Mart store. We got along pretty good then we started to date, I was living on my own so we usually go to my apartment. I had no clue she had a cock, she was a very beautiful woman with size B tits. We dated for about a month when talk her into just taking her shirt off, after a while without her shirt off she finally took her bra off. I would make out with her and suck on her tits, lick her...

3 years ago
  • 0
  • 14
  • 0

First time with top tranny

We went in her room, I paid her and while I was getting undressed, she was waiting for me by the bed. She was slowly stroking her cock, and didn't bother to remove her panties or lace body suit. She just moved them aside and pulled out her cock and boobs.She was tall, at least 180cm, latina, slim, hot, long dark hair big boobs and nice and big cock, (later when she was hard, she was probably 18-20cm). She didn't speak English, but she was so hot and I was so horny, ready to make my fantasy come...

3 years ago
  • 0
  • 5
  • 0

My First Tranny

My name is Holly, and I'm twenty-eight. I'm a blonde, and I happen to be a lesbian. I have been with a couple guys before, but that's it. Anyway, one night, I was at a club securing the perimeter. Looking for some cute ladies, that maybe I'd take home. I saw a lot of worthy candidates, and a couple with D-cup racks. I wasn't a slut or anything like that, but I definitely played the field. I looked around the entire club a few times, and caught a few eyes. I saw a few ladies casually stirring...

Trans
4 years ago
  • 0
  • 6
  • 0

My First Tranny

I met Charkara (her real name) through an adult dating site. You can find her pictures on my xhamster page titled, "My First Tranny". We corresponded through the dating site quite regularly before we decided to take it to next level and exchange phone numbers and email addresses. We talked on the phone getting to know each other, what we liked to do sexually, etc. She came off as a total freak willing to do most anything which was an extreme turn-on for me. We then begun having phone sex...

3 years ago
  • 0
  • 8
  • 0

The Trucker and The Tranny

The Truck Driver and the Tranny fiction by [email protected] This is a work of fiction for mature readers, containing explicit sexual acts which may be illegal in some backward parts of the world. If it's illegal where you're reading it, you should MOVE! If you're too young to be reading erotic and explicit sexual fiction, don't go any further. I was working as a truck driver, moving periodically to new areas of the country (mostly around my hometown of Nashville, TN) in...

2 years ago
  • 0
  • 8
  • 0

FUCKING MY FIRST TRANNY

FUCKING MY FIRST TRANNYIn the early to mid 90's my wife and I were living in south central L.A. The wife wasn't necessarily a sexual creature nor was she very good at it. This lead me to a lot porn watching and going outside of the house for hot, kinky sex. She doesn't know I'm Bi and still doesn't to this day. I would frequent various adult bookstores to get/give blowjobs, handjobs and visit the occasional gloryhole to get my freak on. I would also travel up and down Figueroa or more commonly...

1 year ago
  • 0
  • 5
  • 0

Hotel Pool Tranny

As I headed toward the office, I could see the pool, and immediately thought about taking a swim after checking in. After getting my room key, I decided to cut through the pool area. It was a large pool for a hotel, there were plenty of chairs, and it looked very clean and inviting. Casually looking around, there were only a few people, and as I continued toward the other end where my room was, there was an attractive younger lady that caught my eye. She was laying on one of the loungers by...

3 years ago
  • 0
  • 11
  • 0

My 2nd time with my tranny

I’ve been talking to this woman for awhile. After our steamy car make out session I was hooked. I didn’t care if she had a dick. I wanted more of her. It was clear that she wanted more from me. We texted non stop everyday. It was fun. She blew up my phone with loads of naked selfies. I’d sit and admire her beautiful body. With every picture she’d send, my dick would throb with excitement. She would even ask if videos of me masterbating to her pictures haha she was amazing. whenever I worked...

2 years ago
  • 0
  • 6
  • 0

My dream encounter with a tranny

There is nothing more hot than to have a slim, pretty body on my hands to fondle. To feel their erections starting to grow and to taste their cocks in my mouth. I lose control when I'm around a shemale.I have fantasized a lot about getting fucked for long periods of time and in a lot of different positions. Unfortunately, all my shemale hookups have been with escorts that do the deeds rather quickly and then leave. I still have to find a shemale friend to spend long long hours either fucking,...

3 years ago
  • 0
  • 5
  • 0

Shooting with a tranny

I was bored one day so i decided to rent out a transsexual escort. I called her up so we can do a special photo shoot together and needless to say, we ended up fucking. She came to my door with an all black dress on and the sides were transparent. She had 5 inch open toe heels on and a leather jacket that came to her waist. Her hair was long and curly and she was fair skinned and spanish about 5'8 with heels on. She walked in and asked me where i wanted to start. I pointed to the couch and she...

4 years ago
  • 0
  • 5
  • 0

Truckpark Tranny

I would never go out looking for it, I'm a good girl. But I would never avoid it. After all, just being dressed in black inch-mesh fishnets, held up by suspenders from a black lacy basque, nipped hard at my waist, with my cock-clit barely covered by my pink g-string pouch and the string over my divine snow white left cheek, while I tottered about on 8", platform heeled, "fuck-me" shoes, and nothing ...

2 years ago
  • 0
  • 5
  • 0

My First Tranny

My name is Holly, and I’m twenty-eight. I’m a blonde, and I happen to be a lesbian. I have been with a couple guys before, but that’s it. Anyway, one night, I was at a club securing the perimeter. Looking for some cute ladies, that maybe I’d take home. I saw a lot of worthy candidates, and a couple with D-cup racks. I wasn’t a slut or anything like that, but I definitely played the field. I looked around the entire club a few times, and caught a few eyes. I saw a few ladies casually stirring...

2 years ago
  • 0
  • 8
  • 0

Amber The Teen Tranny

I was horny as fuck that day as I hadn’t jizzed in a few days due to work being so hectic. I debated how to get my rocks off and decided to go cruising at the park for some cock. I took a quick shower, threw on a pair of pink frilly panties, a pair of loose sport shorts, and a long tshirt. I hopped in my car and drove to the park, teasing my little prick by rubbing it in my sissy panties, leaking copious amounts of precum into them as a result. I parked and headed towards the wooded area...

2 years ago
  • 0
  • 4
  • 0

Laundromat Tranny

It was laundry day. Vincent, or Vinnie to his friends, loved laundry day. It was a time to relax, catch up on reading, and listen to music while the washing machines whirred in the background.He was tall and ruggedly handsome, with dark, almost Spanish features. In his five or so years of living alone, he always cherished his trips to the laundromat.Walking slowly from his house to the laundromat, he whistled a tune. In his little trolley, he had his laundry and detergent. Sitting on top of his...

Trans
1 year ago
  • 0
  • 18
  • 0

Exploring the Tranny

At first I didn’t like that my wife, Jan, was hanging out with a “guy” several times per month. She insisted, however, that her friend “Crystal” was actually a girl trapped in a man’s body — and as such was attracted to men. Since she posed no sexual threat, she enjoyed their time together because they shop and talk and hangout without expectations. To be fair, my wife had a soft spot for gay men - she’s had numerous gay friends over the 8 years we’ve been together. Crystal (formerly Chris) was...

Transsexual
3 years ago
  • 0
  • 14
  • 0

Supermarket Tranny

It was a typical Saturday morning. I was at the grocery store doing my weekly food shopping. As I was perusing through the vegetable section my eyes caught sight of a a very attractive woman. She had long dark brown hair, pretty face and a nice body. I worked my way over to her and checked her left hand for a wedding ring. She had none. I made some remarks about the slim pickings the supermarket had. She and I quickly engaged in conversation about cooking etc.We walked around the store side by...

2 years ago
  • 0
  • 7
  • 0

Building site tranny

So I woke this morning in a particularly aroused state, I decided I would treat myself some naughty fun, I decided to dress like a slut under my work clothes. I rummaged around in my drawer and pulled out some black seamed nylons, black lace panties and and my favourite lace corset. I began by showering and shaving my whole body, once I had finished I began by rolling the smooth nylons on to my smooth muscular legs, then came the lace corset followed by the small lace panties, I then reached...

3 years ago
  • 0
  • 5
  • 0

First ass I fucked was also my first Tranny

Me again, I haven't shared any of my stories in a while but was chatting to an old friend about this one last week and thought I would share the story. Again names have been changed to protect identity, all my stories are true and I am not a author, just a horny guy with some horny stories. Thanks.I was 20 years old and had been playing with guys and gals for many years now (check old stories). I had arranged a night out with some of my friends to celebrate a birthday so put on my new shirt,...

1 year ago
  • 0
  • 14
  • 0

Amber The Teen Tranny

I was horny as fuck that day as I hadn't jizzed in a few days due to work being so hectic. I debated how to get my rocks off and decided to go cruising at the park for some cock. I took a quick shower, threw on a pair of pink frilly panties, a pair of loose sport shorts, and a long tshirt. I hopped in my car and drove to the park, teasing my little prick by rubbing it in my sissy panties, leaking copious amounts of precum into them as a result. I parked and headed towards the wooded area...

3 years ago
  • 0
  • 6
  • 0

supermarket tranny

It was a typical Saturday morning. I was at the grocery store doing my weekly food shopping. As I was perusing through the vegetable section my eyes caught sight of a a very attractive woman. She had long dark brown hair, pretty face and a nice body. I worked my way over to her and checked her left hand for a wedding ring. She had none. I made some remarks about the slim pickings the supermarket had. She and I quickly engaged in conversation about cooking etc.We walked around the store side by...

3 years ago
  • 0
  • 5
  • 0

My sister my first the tranny

A little something different to spice up your lives*******************************************************************************************************************************************************************************************It was the first week of June and school was out for the summer, I was 18 and had just finished my senior year. One night while we were eating dinner, My Mom and step dad informed me that they were going away for two weeks. When they got married they did not go...

1 year ago
  • 0
  • 11
  • 0

tranny

Let me tell you a little bit about myself I'm five feet 10 inches tall around 220 pounds, brown hair and eyes very muscular, I'm an ex-professional boxer. Around 10 years ago I I was working as a bouncer erotic a nightclub in Fort Lauderdale, when one night I heard a commotion in the parking lot. There were several men beating up a beautiful woman, when I tried to break it up I ended up getting very banged up myself. Her name was misty, she thanked me for helping her and asked if I need a...

4 years ago
  • 0
  • 6
  • 0

I WAS HIS FIRST TRANNY

I had been on this sex dating site for only a few weeks, when I got a request to meet from phillip, I looked at his profile and it read 25 year old single male, looking for older women, sexual orientation-straight,I thought to myself , should I tell him? No fuck it let him find out for himself.So I arranged a meet with phil for the following day at 2pm,I douched, showered, took my time putting on make-up, dressed , did my hair (wig) and nails, although I say it myself I looked hot, not slutty...

4 years ago
  • 0
  • 6
  • 0

Finally My First Tranny

I just came out of the doctor's office in downtown Philly from my 3 month check-up. I was pretty horney since my doctor is a female and I had a complete physical so she and her nurse were in the room with me. I got to the train station to go back to Willow Grove and was standing on the platform when I saw this beautiful brunette haired woman about 10 feet from me. She was wearing jeans, and a spagetti top shirt. I could see that she had a real nice pair of tits and my cock started to get hard...

2 years ago
  • 0
  • 16
  • 0

Date Coach from sissifyourself

Chapter 1“So what brings you here today?”Daniel looked at the date coach. He wasn’t sure of his height, taller than himself for sure, who stood at a paltry 5’ 4”, even though he was already 23 years old. He’d been made fun of his whole life for his height, but he still had a good bit of muscle, and some fat on him, as he weighed about 150 pounds, with nary a hair on his body. The doctor on the other hand, still looked athletic and muscular through his button down shirt, and didn’t look a day...

1 year ago
  • 0
  • 21
  • 0

Date Night with Mom

(Credit to the beautiful Ava Addams for the cover photo.) I am hanging around the apartment by myself one night when the phone rings. I glance up from the textbook I was reading and over at the phone with some annoyance. It was the landline which meant it was almost certainly for my roommate Craig. It was probably his work calling. Besides telemarketers they were the only ones to really use that number. Despite needing the shifts Craig refused to give them his cell phone number. He had a...

Incest
3 years ago
  • 0
  • 23
  • 0

Date Night My Descent Into Slavery

Date Night. My Descent Into Slavery.------------------------------------------------------------------------ CHAPTER 1 FRIDAY Tonight was "Date Night" and as usually was the case, I'd spentthe day in a high state of anticipation. My wife, Chris, and I hadcreated the "Date Nights" several years ago to merge our divergentsexual desires into a mutually satisfying relationship. My sexual tastes ran to the more exotic side of the spectrum:...

1 year ago
  • 0
  • 10
  • 0

Date Night femdom classic

DATE NIGHT (femdom classic)A wife turns her husband into a sissy slut who is forced to service other men and women. Tonight was"Date Night" and as usually was the case, I'd spentthe day in a high state of anticipation. My wife, Chris, and I hadcreated the "Date Nights" several years ago to merge our divergentsexual desires into a mutually satisfying relationship. My sexual tastes ran to the more exotic side of the spectrum bondage,forced oral sex, prolonged sessions, feminization and...

4 years ago
  • 0
  • 20
  • 0

Date With My Aunt

My aunt Sharon has always been a secret crush of mine. She’s my mom’s younger sister by a couple years currently aged 45. She’s blond with a hint of grey, bright blue eyes a pleasant demeanor and just as sweet as can be. Her body, after a daughter, is surprisingly tight, solid B cup. Her husband founded a manufacturing company, and in a short while exploded into wealthy relative to the rest of my extended family’s standards. I’m Ryan and I come from a fairly comfortable middle-class family....

2 years ago
  • 0
  • 7
  • 0

DATE NIGHT

A wife turns her husband into a sissy slut who is forced to service other men and women.Tonight was"Date Night" and as usually was the case, I'd spentthe day in a high state of anticipation. My wife, Chris, and I hadcreated the "Date Nights" several years ago to merge our divergentsexual desires into a mutually satisfying relationship.My sexual tastes ran to the more exotic side of the spectrum bondage,forced oral sex, prolonged sessions, feminization and rolereversal were exciting fantasies...

Porn Trends