FIRST TIME TRANNY free porn video

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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 trousers down and sat down to relieve myself. As my eyes became accustomed to the gloom, I could see the mass of graffiti on the door, the walls, everywhere.

There were all sorts of lurid stories, phone numbers, invitations to meet, plus crude pictures roughly drawn in black marker, mainly men in fishnets with large genitals, one picture showed someone bent over in stockings, suspenders and boots, a dildo in their arse. As I read the stories and looked at the pictures, I felt my cock between my legs start to stiffen and I subconsciously started to rub myself.

As I fondled my rapidly stiffening cock, a piece of toilet roll wrapped around a pen was pushed under the cubicle. I was a little worried but took the note

“do you like the stories?” it asked.

“yes” I wrote on it and passed it back.

A second passed and then another note…. “I like the tranny stories, do you?”

“yes, I love them” I wrote back.

A magazine featuring trannies was pushed under the door showing hard sex, penetration, etc…At this, my cock grew a little stiffer.

Then a small glass vial was pushed under the door with another note. “cover one nostril and sniff these, it is good” it said.

I was not sure, the small brown glass vial had liquid in and small white things in the bottom. I unscrewed the lid and a thick heady aroma hit me. I decided to give it a go and took a deep sniff from the bottom. All at once the whole world seemed to kick sideways, the veins in my head started to pound, my cock got that stiff I thought it might break and my head rushed. With one hand one the wall to steady myself, I couldn’t help but slowly grab my cock, the feeling of pleasure intense.

Another note appeared…… “strip off now sexy”….

I was so awash with the feelings, I lost all sense and took my jeans, t-shirt and boxers off which I dropped to the floor. In an instance they disappeared under the dividing wall and I started to panic, however a plastic bag was pushed under the door.

I open the bag and fished about inside and found a pair of black stockings.

“Put them on” a voice hissed. I sat on the toilet and rolled one of them onto my legs. I was not naturally hairy so the smooth stockings hissed over my legs as I pulled on, and then the other up. I experimented crossing my legs feeling the smooth swish of the stockings to be very nice.

In my reverie, I though I heard a whispered conversation take place, then the click of a clamshell mobile being shut.

In the bag was also a black basque top with suspenders attached. Once I had figured out the small clasps on the back, I managed to struggle into it, the boned sides holding me in rather pleasingly. I then played with the suspenders for what seemed an eternity , finally attaching them to the stocking tops, rather pleased with the way they looked.

Once done, I sat on the toilet, small cock protruding from between my stocking clad legs.

Then, another bag, this one a small sports bag. In it was a cheap shiny pvc type jacket which I put on and a rather tatty blonde bob wig which I put on over my own short hair. Then a pair of black shiny gloves in a wet looking material which I put on.

Finally a pair of boots was shoved under the divide to me. They were black, not leather, but shiny type material, very cheap looking. A high spike heel that was looking very scuffed, these boots had seen a lot of action. One boot had a white stain on down the shaft, but I wanted to put them on.

Zzzzzzrrrrpppp, the noise of the zip opening sounded like a thunder crack in the quiet toilet. Once opened, I nestled my foot into the boot and very slowly drew up the zip, the boots tightly closing over my stocking clad leg. I quickly got the second boot on, and , teetering on the heels, stood up.

“very nice” the voice coaxed from next door, turn around. I slowly turned around wobbly on the heels, but feeling good. I leaned over the toilet, my hands on the cistern, my bottom stuck out.

“pose for me”

I wriggled my bottom and enjoyed wearing these strange new clothes.

Suddenly, a large thick cock was pushed through the hole in the wall.

“touch it” the voice said, quietly and slightly panting.

“I have never done this”

“and you have never dressed like a cheap whore either, now just do it if you want your clothes back”

I slowly reached out and touched the cock, it seemed massive compared to mine.

“wank me slut”

I slowly grasped the cock and slowly pulled back the foreskin, an audible sigh of pleasure could be heard. I started to speed up, getting used to wanking a cock from face on, my only experience being the top down view of my own.

As I built up speed, the cock got harder and harder.

“now suck it”….

“no” I said, I was not expecting that.

“suck it NOW”

“no, I don’t want to”

BANG

The door was kicked open and outside was a gang of men, all over 45, tall, unkempt, in jeans, leather jackets, shirts.

The cock was withdrawn and my “friend” came into my cubicle. He was about 50, over 6 foot tall, broad, unshaven yet quite handsome in a slovenly sort of way. His hard cock was out of his jeans.

My friends came as soon as I called and I promised them action, so you had better open your mouth.

I was too scared to do anything else and I opened my mouth a little. He put his hang in my mouth and levered my jaw down. Suddenly he grabbed my shoulder and pushed me to my knees, I was kneeling on the cold piss streaked floor, my stockings getting wet, my heels digging into my ass cheeks.

Now, good girl, stay there.

He edged closer, his large tool inching closer to my mouth.

“we can do this the easy way or the hard way”

I decided to embrace my situation and I slowly leaned forward, grabbed the cock in my gloved hand and slowly guided it into my mouth, just the bell end at first.

“good girl, now get that tongue to work”

I run my tongue around the large knob. It did not taste bad, or unclean, just different. I closed my eyes as I run my tongue around his manhood, my other hand caressing his large tool.

All of a sudden, I felt something warm on my back. As I opened my eyes, one of the guys had his cock out and was pissing on me.

I stopped licking and went to protest but my main tormenter grabbed the back of my head to keep me in place

“you are our slut now and will submit to anything we want”

I resumed my duties, allowing the cock to be pushed deeper into my mouth. I got into a rhythm and started to bump my head up and down, the cock sliding in and out of my madly salivating mouth.

“look at her, cheap little poof, in that cheap jacket and fuck me boots”

I didn’t care, in fact their words were beginning to turn me on a little and I started to wank as well as gobble the cock.

This seemed to be a sign and soon I had 3 hard cocks in front of me, I sucked on one and wanked the other two.

Without warning, one cock shot a wad of hot spunk down my front.

“next one in your mouth slut” I heard.

I tensed a little until the poppers were again shoved under my nose and I inhaled a deep deep draft. The rush returned and my own cock stiffened and I sucked like a thing possessed until the cock hardened and a thick wad of salty cum shot into my mouth. I gagged a little, some of it running back out around the head of the cock but I managed to swallow a lot of it, and it did not feel bad as it slithered down my throat.

“she’s good for a first timer”

FLASH

“hee hee, look his phone takes good pictures”. Fuck, they were using my own phone to photograph me. This was followed by a BEEP BEEP of an incoming text.

“It’s mummy, what do you want for your tea”. The guy holding the phone played with the phone then said “I’ve texted back that you have already eaten!”. Now, if you don’t want these pictures sending out, you will do all me ask.
“okay, okay, anything”

“make like you mean it”

“I looked up at the pack leader from under my lids, pouted and said in a husky voice

“Use me and abuse me, that is what I want”

With that, I was dragged to my feet, my wet stockings clinging to my legs, the spunk dripping off my pvc jacket. I was led out of the cubicle and to the sinks. I was then told to grip the taps and bend over.

I did as I was told and one guy started to touch my little pink rosebud. His finger was wet with something.

“this will help, be grateful for it, a lot of our girls don’t get this”

I allowed him to smear my little bum hole and then he slowly pushed one finger in. I grunted in discomfort..

“relax bitch, that is just the start”.

I was passed the poppers and I voluntarily took a huge hit my ass muscles relaxing as the fingers were pushed in. I kept hold of the phial, knowing I would need it more.

The finger slid in and out and I began to relax. This was joined by a second finger and my little hole began to stretch. As this continued, the audience were all wanking behind me, their stiff cocks are growing and growing.

“right, now time for the real fun”

I was made to kneel on a coat on the floor, my legs open. Picture the scene, me on my hands and knees, stockings laddered and wet, scuffed pvc high heeled boots on, pvc jacket riding up my back, wig slightly wonky matted with cum.

In this position, one guy got in front of my and slid his tool into my mouth. As I started to suck his rod, I felt something wide and warm poke at my ass. I spread my legs a little and pushed back like an eager girl. As he pushed, the hard knob started to open me and slowly slid into my sphincter. Even with the preparation, it felt like my ass hole was being slit with a razor and I wriggled and bucked. The cock was relentless and it pushed past my unwilling muscle, stretching me wide and wide like a red hot poker in my stomach. As I bucked, the pressure grew, the pain intensified and I felt tears in my eyes until suddenly the pain subsided and the cock was fitting into me. I took a breath and steadied myself just as another shot of jizz flew into my face. I licked if off my lips and decided to go for it. I actually beckoned another guy to me who quickly replaced the spent cock with his. I quickly took it into my mouth.

At the other end, I was being slowly fucked and I started to get the rhytmn, pushing back in unison, fucking back, not just being fucked. Within minutes, my deflowerer grunted and stiffened and what seemed like a gallon of hot cum splashed into my ass and started to seep out. As he pulled out with a plop, my original “beau” got behind me. He shuffled close, his belt scr****g on the floor , and started to caress my booted legs

“I love a slut in boots” he whispered, then , taking hold of my boot heels like handles, he pushed his cock into me and started to ride me. By this time, I was really into it and between cocks I was sniffing poppers like an old queen.

Over the next 40 minutes, I was fucked by all five guys and must have took 4 or five loads down my face.

One by one they drifted off until only the first guy was left. I was sat on the hard, cold, piss and cum stained floor, my stockings soaking, my boots and face streaked with more jizz.

“did you like that”

“yes, I did, I love being a slut”

I will be in touch, I have your number. With that he threw my clothes at me and left.

I quickly changed, scr****g the worse of the spunk off. My outfit was unsalvageable so I left in a heap on the floor and got myself home.

That night, as I nodded off to sl**p having wanked for about the 10th time, my phone beeped.

It was a message from him….

REPORT TO MY HOUSE, TOMORROW AFTER COLLEGE, DO NOT BE LATE. MAKE SURE YOU ARE TOTALLY SHAVED.

I drifted off to sl**p with a smile on my face.

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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
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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
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Mortimer and Myrtle A Love Story

Note: This is not your usual Lush story. It is an experimental play in a theater of the absurd style. There is no sex but it is an entertaining comment on marriage. I encourage you to indulge in something different. I think it will make you laugh and maybe cry.Scene: A formal living room. Mortimer is seated on a sofa in the center of the room when Myrtle enters and sits on the sofa next to him. She is wearing a blue floral dress and a pearl necklace, her gray hair is tied in a bun. Mortimer is...

Love Stories
3 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,...

3 years ago
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The Liberation Of Father Mortimer

When Father Mortimer checked into the hotel it was eight in the evening.The room was a basic no frills double with a small bathroom. He would never stay in such a hotel if he was attending one of his ecclesiastical conferences but for what he had planned it was just perfect.He got down on his knees and bent his balding aged head over a black gilt leaf Bible he had respectfully placed on the edge of the bed.“Blessed Lord Jesus forgive me for my sins,” he muttered and crossed himself three...

Spanking
3 years ago
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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...

4 years ago
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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
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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...

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...

2 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
1 year 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...

2 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...

1 year 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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  • 6
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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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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...

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...

1 year 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...

2 years ago
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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,...

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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The Amazing Mr Mortimer

THE AMAZING MR. MORTIMER My girlfriend Rachel and I had decided to take a two week vacation to PuertoRico. I had first come across the girl on the streets of San Juan. She cameup to me and begged me for some money. At first I was going to say no. ThenI noticed how beautiful this young girl was and I was intrigued. I startedto reach into my purse to get her something, and she smiled at me. She hada very beautiful smile. It was in fact an entrancing smile. I kept her close to me with small bribes...

1 year ago
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Mortimer and Myrtle A Love Story

Note: This is not your usual Lush story. It is an experimental play in a theater of the absurd style. There is no sex but it is an entertaining comment on marriage. I encourage you to indulge in something different. I think it will make you laugh and maybe cry. Scene: A formal living room. Mortimer is seated on a sofa in the center of the room when Myrtle enters and sits on the sofa next to him. She is wearing a blue floral dress and a pearl necklace, her gray hair is tied in a bun. Mortimer is...

2 years ago
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Lunchtime Munchtime

As was his habit at lunchtime, Hal left the building and walked through the office park for exercise. It was a partly cloudy day, and for the moment it seemed overcast. On his way to a small path through the woods, he saw her. Sandy was an attractive redhead with a sensual voice who almost always wore a tailored blouse, a roomy ankle-length skirt, and one-inch pumps. Her wardrobe varied in color, patterns, and material, depending upon the season, but always the same ensemble. Hal watched as...

1 year ago
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Wartime

Elizabeth Fleming told me some of this story in the years before she died, aged eighty, in 2010. The more graphic scenes are mine but the emotions and surrounding history are hers. She was my Great Aunt, great in so many ways for she was the third family member I ever revealed my sexuality to, the first two being my parents. I had known since girlhood that she shared a cottage in Hampshire with her friend, Portia, but had never known their relationship was more than sisterly. When I told her...

Lesbian

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