First Time With A Transsexual Escort free porn video

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True Story about my first experience with a transsexual escort.

Where I live there isn't many options or chances to meet a transexual. I'm from a small city in a small state that just to be honest is behind the times still. I had always wanted to experience being with a transsexual but could never find any on websites in my area. After several years I just so happened to come across a ad on a website for a transsexual being in my city for a few days in between traveling. She was beautiful! Tall with a gorgeous body, long blonde hair but the one thing that concerned me was the size of her package. At the time I had only used toys on myself and none were as big as she was which kind of scared me... I decided to call her and fell everything out and go from there. She was free that afternoon so I talked myself into making a date with her. I jumped in the shower and shaved everything up and was heading her way a hour later. I was so scared when I knocked on her door and when she opened it I wanted to run but was frozen in place. Once in her room I noticed a older black man and a white guy dressed as a woman. Tonya was dressed in some really sexy red lingerie with knee high black boots. Her hair was down and curled beautifully and I will never forget her bright red lipstick she was wearing. I just stood there as the 3 talked and seconds later the two men left. Tonya could tell I was nervous so she had me sit on the bed while she finished getting everything ready. While she was walking around the room I took off my shirt and pants so I was standing there in my boxers. Under my boxers I had on one of my girlfriends really small thongs but was embarrassed to show them. Tonya lit a cigarette and came over and sit beside me noticing I had removed most my clothes. As she took a draw from her cigarette I instantly got a hard on. It didn't show much because I'm only five inches but I could definitely feel the thong tightening around my cock.

She had me stand in front of her and made me pull my boxers down, I thought about pulling the thongs down with them to save some embarrassment but changed my mind at the last second. So there I stood in front of her in a really tiny red thong with a hard on that wasn't big enough to even poke out the top. She let out a small snicker and then complimented me on my thong which I told her it was my GF's. She laughed again and told me my GF has good taste. As she ran her hand over my hard on she asked what had gotten him so hard and I told her it was from watching her smoke. She smiled as she took a draw from her cigarette and then used that hand while still holding the cigarette to reach into my thong and pull out my tiny cock. Precum was pouring out my head as she stroked it and then wiped it with her finger and stuck it in my mouth making me eat my own precum. She told me to get use to it because I would be eating plenty. I could tell from the time I stepped in the room she was the boss and everything was going to be her way wether I liked it or not which is how I wanted it. She stroked me a few more times then put my cock back in my thong and laid back on the bed pulling her thong to the side releasing her soft 9" cock. I knew what I was suppose to do but wanted to wait to hear it from her so seconds later she told me to get on my knees and start sucking. This would be the first cock I had sucked that wasn't in a dark room at a adult bookstore so I was a little intimidated by it. It just kept growing and growing as I sucked it and I kept having 2nd thoughts about being able to take it in my ass. Tonya held me by my bald head as I sucked it for a good 10 minutes, she kept saying I was a natural cocksucker and that I would be doing it a lot more from here on out. Once she was hard she made me get the lube and condom from the table along with her cigarettes. She stood beside the bed and made me get on my back in front of her. She raised my legs and poured lube down my crack and lubed up her cock. She put my legs on her shoulders and had the head of her cock just starting in my asshole when she stopped everything and put a cigarette in her lips. As she lit the cigarette I could feel her cock starting to slide in me and by the time she finished her first draw from it she was all the way in me. She moved my legs to her sides and leaned down on top of me kissing me as she exhaled the smoke. I still had on my thong but I know my cock was jumping like crazy while she did that. She leaned back up placing her hands (with the cigarette) on my chest and slowly started fucking me. It felt amazing with each thrust but I have to admit the first 10 or so pumps the last three inches was killing me! She fucked me like that for several minutes while I got used to it. I don't know if what she did next was a accident or on purpose but she took a really long draw from her cigarette and then placed her hands back on my chest but as she did that the hot ash fell on to my chest making me tense up and jump. It also made me cum in my thongs which she noticed immediately. She pulled her cock out of me and laid down beside me and made me take out my cock and start jacking as she watched. I literally had just came but was still hard as a rock. It only took a minute or two and I was shooting cum up to my chest and neck. Laying there covered in cum Tonya decides to get on her knees and put her cock in my mouth feeding it to me like a mother bird feeds worms to her babies. I felt her grabbing my cock and roughly putting it back in my thong and then got me up on my hands and knees on the bed. She got off the bed grabbed another condom and lube and got in front of me sticking the condom in my mouth and then sliding her cock in my mouth making me put the condom on with my lips. She had also removed her bra and let me suck on each tit for a second before getting behind me. I tried to brace myself for her cock but was caught off guard when she slid into me with ease all the way to her balls. She fucked me hard in this position and I loved it! I could hear the bed squeaking and her voice talking dirty to me while smacking my ass a few times. After about 10 minutes she slowed her pace and laid her boobs onto my back which I loved!! She had one arm around my shoulder/neck and I could feel her breath on my ear and her asking if I loved her cock... (Fuck yeah I did!!) After a few minutes she pulled out of me and got up in front of me. I'm not sure what her plan was but her cock was right in front of my face and I didn't care that she still had a condom on I just took it as deep as I could in my mouth!! After several minutes of sucking her cock she pulled it from me ripped the condom off and shot a huge load of cum right in my face! I ate as much as I could but she wouldn't let me clean any of it off my face. She excused herself to the bathroom but didn't shut the door so I could see her standing at the commode getting ready to pee. I don't know why but I got off the bed went into the bathroom and grabbed her cock to hold it for her as she started to pee. It just looked huge in my hand and as her pee started to turn to a dribble I dropped to my knees and sucked it down my throat.

I think she was stunned by that as she led me back to the bedroom. She reached into a bag and pulled out a pair of pink thongs and brought them to me. I looked down at my GF's red ones I had on and they were a mess from cum and whatever else there was no way I could sneak them back in her pantie drawer. Tonya lit a cigarette but this time kept it in her mouth as she bent down to take off my thong. When she stood up we were face to face and she shoved the red thongs in my mouth. She dropped back down to her knees and started sucking and stroking my cock which was still hard. After a few minutes she asked what position I wanted to fuck her in so I decided to lay down and let her ride me so I could look at her and hold on to her boobs. She made me put her pink thong on then climbed on top of me. As she rode me she would lay her boobs on me and then sat up putting her hands on my chest with her lit cigarette. The more she smoked the faster she fucked me and I was getting close to cumming. She climbed off me and pulled the condom off as I grabbed my cock to stroke it as she took her last draw from the cigarette looking me right in my eyes she put the cigarette out on my chest and my cock exploded with cum shooting loads over my head on to the head board behind me! I was so turned on by her doing that and I instantly set up grabbed her by her hair and started making out with her. She rolled onto her back as I fell on her still making out. My burning chest was rubbing against her boobs my throbbing cock was rubbing against her cock. To be continued...

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My name is Anita. I am a 23 year old es-panic female, 5 ft 5 inches tall, 115 pounds, 32 B breast, 22 inch waist, and 32 inch hips. This is my story of several first for me including bondage, pain, pleasure and anal. My live in boyfriend dumped me a few months back telling me that I was not open minded and adventurous enough sexually and he had found a woman that pleased him much more than I. I was left with the lease on our apartment and all the utilities which put me in a heavy...

2 years ago
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Courtesan versus escort

Courtesan versus Escort Yes, it is important to know the difference to determine which best fits your desire, needs and style. Alternatively it is important to know which type of client you would be. Then and only then we can create the best possible outcome of our randez-vous for an unforgettable peak experience that you perhaps are seeking whether for a day or a lifetime.Different men are looking for different things and there is much confusion around about many terms improperly used in the...

1 year ago
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My WeekLong Affair with a Hot Escort

This was the third time I was meeting Xena. I was having an affair with her and I had kept it a secret from my wife. What do I say? I was addicted to her or rather my cock was addicted to her pussy. And she was naughty as hell so I enjoyed doing things with her of sexual nature. I don’t feel bad having an affair with a hot escort like Xena. Once, she invited me to her apartment and she had a “friend” there. I fingered both of them and licked their pussy alternatively. It was a big success for...

Extra Marital Affair
1 year ago
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My friends daughter is also my escort

business, except for a significant drawback. I have little time to date or put into a relationship. Predictably, as a man in my mid-thirties, I get quite lonely. i found myself searching out the better escort services in the cities I frequent. One of those cities is also the home of a very good, long time friend and his family. It also happens to be the home of my favorite escort service. Steve and I met during my first job right out of college. He was a few years older than I...

3 years ago
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Confession of an Escort

Confession of an Escort I thought readers of Lush Stories might like to hear about my escapades as an escort. It wasn’t something I ever intended to do, but opportunities arose to make life exciting. I thoroughly enjoyed having sex with wealthy married men at the time, and it changed my cozy, but boring life style to one of almost daily adrenaline and sexual highs. Let me tell you what a twenty-five year old married woman did with her time, if her husband was extravagantly wealthy, children...

3 years ago
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Surprised Experience With An Escort

Hi my name is Vijay patil 19 teen years old and im from nasik here is my first real life experience or we can its a confession about an escort girl Nikita whom I met when I was traveling from Pune to Manmad by the passenger train which departs from Pune at night 12:15 am. She only told me about this site and she is a frequent reader so im posting it here she will definitely read it. I will Introduce my self im an average boy with 5.5 height, better physique, dick size 5 inches, fair. which can...

3 years ago
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A Teenage Escort

Introduction: this is my second one A Teenage Escort. Part 1. The Training My family was fairly poor, no, really poor. As a child through high school I was teased about my clothes, shoes, everything other kids had that were nicer. By the time I got to 10th grade at 16 years old I was sick of it. My parents were wonderful just not educated and had lousy jobs. We never went hungry or anything like that but the teasing had scarred me to my soul. One thing I had going for me was I am pretty...

2 years ago
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First time strapon with a mature pvc escort

This is a true story of my first time being fucked by a strap-on. It has been a long standing fantasy of mine to being fucked by a woman wearing one, but not just any woman, I wanted it to be a mature, leather clad woman wearing a pair of fuck-me-boots. So I was looking through adultwork recently as I had a free afternoon coming up and wanted some leather/PVC wearing fun with a mature escort. As i was searching I checked to see if Speedybee aka Mature Trisha was still working. I had seen her...

4 years ago
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The Escort

The Escort By Jennifer Richardson I got the idea for this story from a reply I received from a gentleman who I have been writing a series of fantasies. He is into all manner of kinky stuff so I wasn't really surprised when he requested a tale involving him and a transvestite. He is aware that I'm a hetero transvestite and all the previous stories I'd written for him were hetero too. I checked with him and he confirmed his requirements. What he actually said was: "I don't know...

3 years ago
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My Life as an Escort

I've been an escort since I was eighteen. My job is very interesting. I meet so many different kinds of people. Sometimes I've even traveled to meet some of my clients. I get paid very well and even get tips most of the time. Most men just want a pretty lady to accompany them. I've dated men that were younger than me, or men that are twice my age. It’s been a very interesting three years. I've also been given the most amazing gifts. Some men have bought me Jimmy Choo shoes, Christian Louboutin...

Taboo
4 years ago
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A Teenage Escort

Part 1. The Training My family was fairly poor, no, really poor. As a child through high school I was teased about my clothes, shoes, everything other kids had that were nicer. By the time I got to 10th grade at 16 years old I was sick of it. My parents were wonderful just not educated and had lousy jobs. We never went hungry or anything like that but the teasing had scarred me to my soul. One thing I had going for me was I am pretty with a great body. That led to many of the...

4 years ago
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Escort

Escort by Vickie Tern "Honey, what in the world can we do now?" Melissa looked at me, her arms hanging down helplessly, her hands turned out, empty. I felt equally helpless and couldn't face her, only stare into the middle distance. All I could do was answer her question with the same question. "I don't know -- what can we do?" I had no answer. Our bright future together had disappeared. Turned bleak. The recession had...

1 year ago
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Male escort

Hot male escort Hi, this is sameer from Bangalore, age 27y and height of 5.11 feet and weight of 65 kg, I want to share a experience of mine, that happened while I was working as a male escort in London. I worked as male escort in Bangalore and then I was moved to London with this profile, I was happy as I was going to London, their I learnt many things, including the best way to satisfy a woman, lucky after reaching London, 10 days later I got my first appointed for a lady called Elaine, so I...

Erotic
4 years ago
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So You Want to be an Escort

Today, I was chatting online with a very special friend of mine. We are very close but recently, we have stayed away from fantasizing about each other. Sometimes in life, the friendship takes the greater importance and it is not a bad thing. We were talking about her career goal. She is in her 40’s and back in college after raising her children. As a business major, she was considering the Hospitality Sector: hotels, resorts, etc. I teased her about becoming an escort. ‘Great job,’ she...

4 years ago
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So You Want to be an Escort

Today, I was chatting online with a very special friend of mine. We are very close but recently, we have stayed away from fantasizing about each other. Sometimes in life, the friendship takes the greater importance and it is not a bad thing. We were talking about her career goal. She is in her 40's and back in college after raising her children. As a business major, she was considering the Hospitality Sector: hotels, resorts, etc. I teased her about becoming an escort. "Great job," she...

BDSM
3 years ago
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Chennai It Guy As An Male Escort

Hi to all ISS readers am your sujith back with the wildest sex encounter which took place between me, my client Aditi and her cute daughter Ankita.After reading the story kindly post your comments and feedbacks on You can contact me through Gmail or hangouts.Ladies, aunties, college girls and schoolgirls in and around Chennai can contact me for sex, massage, hot chat, short term and long term fun.My dear girls just ping me to have the wildest sex.I never worried about your age, caste, creed or...

2 years ago
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Graceful Escort

"Relax. It'll be okay," Grace said with a smile."It's just that I've never before hired an escort. You're so beautiful. You look like you could break,” I said as I sat on the edge of the hotel bed."I usually get that once a guy fully sees me. You do want to see all of me, right?""You mean you'll let me?""Sweetie, you didn't hire me to keep my clothes on, did you?""Well, I wasn't sure what to expect. I know an escort is different than a real lady of the night.""True. But...

First Time
3 years ago
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My Classmate is an Escort

https://xhamster.com/users/jasdeepkaurI attend one of the top PG colleges in Pune. I am 6 feet tall and dark skinned. I will not brag. I have a cock that is of the average size. This is a true story about me. I live in Pune alone in my flat as my parents work abroad. This is the story about me and my college friend. I found out that she works as an escort and exploited her fully.Her name was Pallavi. She had fair skin and was of average height. She wore her hair in a pony tail. She also wore...

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