My First And Only Time With A Transvestite free porn video

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This is a true story that I would like to share, and happened during a holiday trip to the beautiful country of Philippines, 4 years ago.

A group of four friends and myself, decided to spent a week at a resort near Cebu city. The guys were talking about the crazy nightlife,
and how they wanted to meet local girls and get hammered. I mostly wanted a peaceful few days next to a pool bar. I had the luck to had
had extensive holidays in my time, as I was mostly working at resorts around the med for many summers. Sex was plenty, as was short term
relationships, of which I had had enough in all fairness.

On the third day there, the guys convinced me to follow them to the nearby town, were a nightlife crowd was gathering. As we sat in the tiny bar, we started attracting
a curious crowd of locals, from watch sellers to girls and women of all ages. Some of the girls were pretty, some other indifferent, a lot of them ugly. What was astonishing to me, was the flirtatious nature of them, the politeness and the silly giggles. I was not in the mood for sex, but I bet I could have gone back with at least a couple of them.

As my partners in crime were indulging in the spoils of love, a transvestite dressed in a killer miniskirt sat close to me. That she was a transvestite was obvious, although she had a killer body, and the miniskirt tight on her waist was complimenting her figure. "Why you don't play with the girls, you no like girls?", she asked, to which I replied that I wasn't in mood for it. We started talking about life and her dreams. She had a feminine voice, somewhat deep. She was talking about her dreams of moving to America one day, and that she wanted to work as a nurse, although currently she was a hairdresser. I noticed she was very well mannered. In my life I have met a lot of gay men, few transvestites and transsexuals. I always thought they are good fun to be with, but never had sexual contact, despite having been offered a few times. She was different, less confident about herself, with a romantic melancholy on her face. Small dark eyes, very penetrating, and a long slim nose. Her chin was almost that of a young boy, but she was just 3 years younger than me. Very smooth skin, hairless, with nice long legs.

At some point she got up. "I am going to toilet" she said, and turned away to disappear in a narrow dark corridor. I noticed the nice curvy arse on her. And then it hit me! I needed to fuck that arse that same night! As she returned, I said "I would love to see your place". She replied that it wasn't a problem as her house was 5 minutes away. I said goodnight to the rest of my friends, who were already drunk and half asleep.

I followed her. She was about a head taller than me. We arrived at what seemed to be a very modest house, with some flowers at the front in makeshift pots. She opened the door and let me in a very modest accommodation with a room adjacent to a tiny kitchen. She had a double bed, but the walls were in a terrible need of fresh paint! "Sit" , she said showing the bed. "You are my first boy", I said. She laughed "I don't believe you".

Since the time I knew I will fuck her, I was wondering what would happen if she wanted to do the same to me. What if she had one of those massive cocks like the shemales in porn movies? What if she wasn't satisfied in a passive role? With these thoughts in my mind, she was pulling down her nickers to reveal a magnificent arse. I felt my cock throbbing. Her slim legs were ending in a curvy bum, with muscle. She turned around to reveal a black thick bush. To my relief her dick was about 1inch. Under the heavy bush, she pulled the foreskin back and then I realised she was already erected. The glans was tiny,the size of her thumb nail. Her dick was strangely small, but her scrotum was enormous! The scrotum was clean shaved in contrast to the bushy pubic hair.

I stood up, pulled down my pants and underwear, my cock was hard as fuck, the cock head purple from the blood flow. She approached and said "Your cock is curvy like a banana". She took it in her hands and started softly rubbing the shaft. She had taken off her heels, and we stood at the same height. She came closer, and with my cock she rubbed her cock head. A current of lust as I felt the tiny red head with my urethra, hot and moist. She pushed closer, so I could feel her enormous balls squeezing against mine. "You shave daily?" she asked, "I try" I replied, and felt her soft hand rubbing my balls. I reached for hers. I felt them cool and heavy in my palm. They were two massive balls, smooth and sweaty. "Baby, suck my nipples" she said with a fainting voice. I took her breasts in my palm. They were budding, as she hadn't operated yet. I suck on her nipples, feeling the areole, salty and dry. As I had bend to reach her chest, my cock head had pressed against her massive balls, her scrotum resting on my cock, with the two balls hanging either side of my glans. I breathed heavily, as I was thrusting my cock under her scrotum. She moaned.

"I want that cock inside me" she said, and she kneeled at the side of the bed. She lift her magnificent arse, lowered her torso and rest her head on the bed. The crack was deep, I held the cheeks with my two hands, and pulled them apart. The smell of sweat and human body filled my nostrils, as I was blaming my unpreparedness for not bringing condoms with me. Like she felt my hesitation she mumbled "Don't worry baby, I douched earlier. FUCK ME". I looked at her tight hole, clean shaved and bleached. My cock was wet and drops of precum were forming on the glans. Her balls her hanging half way down her inner thighs. I lined my shaft with her crack and rubbed it against her cheeks. As I pressed against her, our balls touched repeatedly, and I felt their weight while mine slapped against hers. I pulled back and my glans left a trail of precum on her left asscheek. I braced myself for pain as I held my cock against the asshole. The precum helped, to slide my cock head inside the tight hole. I watched my glans disappearing in it, as she grunted an "Aah".

I spit thickly aiming on my shaft and pressed steadily against her. Till all of my cock disappeared inside her ass. I pulled slowly back and spit a couple more times on the hole. We both started breathing heavily, and the next thrust was easier. I stepped on the bed to rest my knees, and I was physically on top of her ass. Then I noticed the mirror at the side of the bed, right in front of us, that was positioned in such a way that we could both see our reflection both from the front as well as from the back, as another dressing mirror was right behind us, on the other end of the room. I just got so horny by watching the action, from every angle. My hairy ass was making a stark contrast to her hairless one, and my balls were bouncing nicely, as I was thrusting my cock almost vertically into her. I had the chance to compare her hanging balls, that were roughly twice larger than mine, hanging heavily from a long scrotum, between her legs.

We were both drenched in sweat, I saw her back glistening. She was masturbating her cock, while I stepped down from the bed and onto the floor, continuing my thrusting action. I felt her hand holding both sets of balls at some point, while my dick was entirely inside her. "You make me crazy" I whispered, as I stopped the thrusting to feel the moment. She lift her torso to a proper doggystyle position. "Fuck me hard baby, I wanna cum" to which I replied a faint "Me too". I cannot say how long and how forcefully I thrusted. At some point I felt the air as my cock head popped out of her narrow hole, and the a painfully hit her left cheek. She reached to grab it and pressed it nicely in her gaping hole. We both moaning and grunting.

At some point, driven by the moans, the rhythmical slapping noise of my body slapping her ass, her hand rubbing my balls, I couldn't hold more. " I'm cumming" I grunted, and pulled my cock out , as three ejaculutations directed a rather runny cum, on her hole, down the crack and dripping from her balls. I was still holding her, when after a few moments of intense masturbation, she cum too. From her tiny glans and onto the bed cover, seven large thick ejaculations, produced a pool of thick, creamy semen.

It was the fuck of a lifetime for both of us. I layer beside her breathing heavily, and light headed. "You fuck good baby" she managed to wispear and reached over to kiss my chest. "Can I take a picture of you?" I asked. "Only my ass baby.",she replied. "Fine with me" I laughed. And the pictures are now on my profile.

Hope you enjoyed!

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Andee smiled as she read the text message on her phone. Before breakfast, she had sent a somewhat vague note to her friend from the night before about wanting to try Roulette again, wondering if he might interpret the suggested sexual undertones – especially after the enthusiastic round of sex from the night before. She thought for a moment, wondering just how acquainted she wanted to get with Connor. It seemed her “one-night stands” in her sexual adventure were more like weekend-long affairs,...

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3 years ago
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Andee Returns to Las Vegas

Andee settled in for another flight. Her new job had been taking her all over the place the past few months, but the light was almost at the end of the tunnel. This trip to Las Vegas would be the last for the year. The other bonus is that she only had to spend a couple days on her own, as her husband had managed to make some changes to his own plans and would meet her for a bit of an extended weekend. The last time they had been together in Sin City, things had been ... interesting. It was a...

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2 years ago
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Andee Returns to Las Vegas Chapter 3

Andee held her coffee in both hands as she sipped on it. Thecombination of her hangover, sexual exhaustion and lack of sleep, left her struggling to bring her mind around to some sort of clarity. Her hands were a little shaky as she stared blankly at the cup. “I’m not too sure about all the details,” she mumbled across the table at her smiling husband. He seemed to be enjoying the whole thing a bit too much and had been pressing her for some information about her encounter. She hadn’t yet...

2 years ago
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Andee Returns to Las Vegas Chapter 3

Andee held her coffee in both hands as she sipped on it. Thecombination of her hangover, sexual exhaustion and lack of sleep, left her struggling to bring her mind around to some sort of clarity. Her hands were a little shaky as she stared blankly at the cup. “I’m not too sure about all the details,” she mumbled across the table at her smiling husband. He seemed to be enjoying the whole thing a bit too much and had been pressing her for some information about her encounter. She hadn’t yet...

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2 years ago
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Ms Nandhini ndash My School Teacher Chapter 2 How

Ms Nandhini – My School TeacherBy KINGPHANTOMEmail: [email protected] 2Lesson – 1 – How to MasturbateThe morning after I Dry Humped our new class teacher’s ass on our school bus. I woke up hearing my older sister Nithya chechi (Starring “Nithya Menon”) calling out my name. “Shyam you idiot, come on get up. You are late for school. I am gonna tell mom, you better get up.” She shouted at me. It’s a curse to share a room with your older sister. She wants to decide on everything that’s...

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Andee Heats Up Houston Day 1

Andee edged her way through the crowd surrounding the luggage belt. She was happy to finally be off the plane after the three hour flight from Toronto, but still had some peculiar emotions about being in Houston. Ever since her encounter with Don back at the conference in Chicago she had been maintaining a casual connection with him, mostly on a professional level. When she received his invitation to come to Texas for a few days to explore first hand some of the research developments his...

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1 year ago
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Becoming Brandee Chapter Eight

Becoming Brandee Chapter Eight: Sitting at my vanity I carefully outlined my lips. Then I pulled out a tube of china pink lipstick and coated them. My refection pleased me so much. Finally, I coated my pretty colored lips with two coats of shiny sticky lip gloss. I winked at Richard reflected in my mirror who was watching me get ready for work. I then stood up to face him in my freshly ironed cocktail waitress uniform. Today I would be wearing my pink uniform. I loved wearing...

2 years ago
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Andee Heats Up Houston Day 2

Andee woke to the sound of the shower running. Looking at the digital clock beside the bed she saw that it was just after 6:00 a.m. As she sat up in the bed, she was trying to shake out the cobwebs and jetlag in her head when the realization of what had gone on the night before became obvious. She was naked but couldn’t exactly remember at what point during the night her lingerie had come off. She rolled out of the bed, made her way to the closet and pulled on a t-shirt from her suitcase. She...

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4 years ago
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Andee Loses a Bet and Her Panties

The whole matter began shortly after Andee’s 38th birthday. She had made one of the biggest decisions of her life and cropped her long brown hair into a cute “pixie” cut. It was a drastic change in her mind, and not long after she began to feel that she wasn’t being “noticed” as much as she had been when her hair was long. “Men prefer long hair,” she complained to her husband one night, not long after she made the dramatic transformation. But despite his constant reassurances, she still felt...

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1 year ago
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Andee Poses For A Friend

It had been a long time in coming. Andee wasn’t sure if having to “pay up” for losing a friendly bet with her co-worker was just a passing joke in the hallway, or if he was serious about collecting on it. As a thirty-eight year old mom of two very active boys and career woman, she enjoyed a bit of adventure in her life and this was the second time in a year she had found herself confronted with a sexual complication with her friend. Without question, Andee had been a shameless flirt with Paul,...

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1 year ago
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Becoming Brandee Chapter Seven

Becoming Brandee Chapter Seven Today may be one of the most important days of my new bimbo life. I go for my job interview today. I am so nervous. I so want to get this job. Lisa seems to think I am a shoe in. But I am nervous. I so want this job. It means a lot to me and I think it will mean a lot to Richard and I know it will help continue to rein....reinfer...re...make me more comfortable as a bimbo girl happy in her role.To support me, Lisa came over and we went through my...

3 years ago
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Becoming Brandee Chapter Eleven

Disclaimer: This chapter, like all chapters of the Becoming Brandee series are intended for adult readers only. Reproduction in any form may not be done without permission of the author. Becoming Brandee, Chapter Eleven: Julie and I crawled into bed together spent as Richard retired to his room. However, just before heading up to bed, Benjamin and I shared a private moment at the door before he headed back to his home. He kissed me tenderly and told me that he'd like to see me...

2 years ago
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From Candace to CandyChapter 5

We woke up mid morning the next day. I rang down to the servants house and asked that breakfast be served in about an hour. I hustled Candace into the shower, telling Candy that we couldn't play; I had a big day planned for us. And that of course set off a round of what? and why won't you tell me, and I don't care if it's a surprise, which finally ended with several swats to the ass cheeks and a gesture towards the shower. Point made, game, set, match; for now anyway. I went through...

1 year ago
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Becoming Brandee Chapter Twelve

Disclaimer: Like all chapters of the Brandee series, this one is inteded for adult readers only. Becoming Brandee, Chapter Twelve I am now in my fourth month of my tour of gentleman's clubs and adult bookstores and I am really enjoying myself. Julie came out a few weekends ago and had such a fun time watching me in my glory. She says she is going to finish up her Doctorial work sooner than expected and that we might get some more time together. I would really enjoy that as I...

4 years ago
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Grandpa and Grandma come for a visit and the entire family enjoys an incestuous orgy

“We’re here!” Grandma cried as she and Grandpa came through the front door with their suitcases. “Grandma!” the children shouted as quickly the five of them surrounded their Grandparents. Grandma and Grandpa hugged them all – letting their hands grab the firm young asses of their grandchildren. Grandma took special care to press her massive bosom against their chests feeling her nipples harden as she did. Grandpa’s large pecker had been hard since...

2 years ago
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Chandigarh Ki Bhabhi Ko Bnaya Randi

Mera naam harman hai. Yeh meri pehli story hai indian sex stories pe. Yeh story meri bhabhi k baare me hai. Iss story mein m btaunga k kaise mene apni bhabhi ko apni randi bnaya. Apne baare me btata hoon. Mera lund 7 inch ka hai aur height 6 foot. M chandigarh ka rehne wala hoon. Mujhe ladkiyo ko randiyo ki tarah chodne meh bahut maaza aata hai. Chandigarh ki agar koi ladki, bhabhi ya aunty ko badeh aur motte lund ki talaash hai toh meri email pe msg kre: .Chlo story shuru krte hai. Meri...

3 years ago
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Becoming Brandee Chapter Thirteen

Disclaimer: Like all chapters in the Brandee series, this one is also intended for adults only. And, like all other chapters, no part of this story may be reproduced without permission of the author. Enjoy. Becoming Brandee Chapter Thirteen: I think I was telling you all about my publicity and promotional tour before getting side-tracked by hygiene issues in the last chapter. Let me fill you in on a few of my adventures with some fascinating audience members who've won the "Win...

2 years ago
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Mysterious Case Of Anjali With Nandita And Nivedita

Hello readers. Handshake to boys and boobs shake to girls. I hope you enjoy the story. This story is for all the BDSM lovers out there. The story is long and detailed and mysterious. Sit back and enjoy. This incident was not a one day story, so it needs some background to be told. So, enjoy the thrill and mystery which lies ahead. I had a cute neighbor whose name was Anjali. She was 2 years younger to me. We were brought up together and we were pretty good friends. This incident started to...

4 years ago
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Andersonville 23 A Twinkle in her Fathers Eyes

Flashback - 11 months earlier (Author's notes - the intro takes place 'right after' Andersonville 6) There were fifteen men and women crowded into the small conference area. As Colonel Myers surveyed the room, he noticed most of them, the programmers anyway, were about half his age. Barry shook his head; he was getting old. His goal was to make general before he retired, and the Andersonville project had seemed like the best way to increase his chances. The problem was, he had...

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