My Date With A Tranny free porn video

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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.

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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 ...

3 years ago
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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...

3 years ago
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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
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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
2 years ago
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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
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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
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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...

4 years ago
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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,...

2 years ago
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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...

4 years ago
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  • 19
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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
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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...

2 years ago
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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
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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
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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
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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...

2 years ago
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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
4 years ago
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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:...

2 years ago
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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
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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
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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...

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