First Time For Everything free porn video

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I was 21 and I had been crossdressing for a while. I had no idea I would later transition and become a transexual. Back then, it was all about the excitement of doing something apparently taboo, which really excited me. I felt dirty and embarrassed afterwards (thanks to my catholic upbringing), but I still loved it. I had started wearing my mom's and my sister's clothes since I was 10 but I was growing taller and they were not. Had a problem with the shoes too. Dressing as Santa Claus for a 3rd Grade Christmas party at school gave me the opportunity to wear Mom's black boots in public, that was so exciting.That was the main reason why I went for the stretchy clothes and luckily, Mom's wigs still fit. I still did everything behind closed doors and when everyone was not home. Nobody knew, at least that is what I thought. I really enjoyed prancing around when no one was home; I came savagely several times, usually with something big up my ass, all the time wishing I had someone to play with.
At that time I was still going to college. I was taking a Philosophy class that most people thought was boring. The class included several extra practice sessions for the exams, and the professor had hired a couple of Philosophy major students to take care of them. That is when I met Carlos. Carlos was one of those volunteers. He was tall and had a thick built. He had a moustache and glasses that made him look older than he was. I met him at the cafeteria one time, and he told me to sit next to me to chat. He was a very interesting fellow. We chatted and during the course of the practice sessions we became good friends. One night he invited me to a party at his house, and I said ok.
I used to keep myself shaved and smooth back then too. I usually wore long sleeves and never wore shorts because I didn't want my buddies to see my smooth legs, that I kept nice and soft with my mom's lotions. But I guess Carlos must have noticed at one point. Must have been when I raised my hand in class because what happened next was well beyond what I had ever experienced.
I arrived around seven and he opened his door in a bath robe. He lived alone because his family apparently was well off . We went past his living room and told me to follow him to his bedroom. I stood in a room surrounded by dozens of dresses, nylon stockings, shoes and wigs. He even had a vanity, which I suspected full of make up items.
" I did notice you are very feminine, so I took my chance and decided to show you all the stuff I had collected. I do not dress anymore, but I do like to help out guys who still do" , he smiled and told me not to freak out, that it was cool. He said there were several guys that were coming over to dress and play girl and he had been hosting them for a while. Carlos then showed me three or four mini dresses and a couple of patent stiletto boots.
"I think these would look great on you! I noticed you have long slender legs, do you shave them too? I have stuff in the bathroom if you need to " ... I was delighted. I told him I had shaved the nite before and he told me to take my clothes off and try out the outfits.
"I wiggled myself into the tight spandex, neon pink outfit. "Wow, you look very sexy in that!", he exclaimed. He produced some silicone breast forms from a dresser and helped me put them on.
" Now you will have some proper curves, sweetie", he made me look in the mirror and I got an instant erection. I had never looked this hot and I loved what the 5"heel ankle boots did to my legs.
"Hmmmm, we have a hair problem to solve now", he said. He walked into his closet and brought two longhaired wigs. "Straight or curly?" I chose the wavy, long wig. Brown hair with blonde hi-lites was in back then. I had no idea what to do with the make up he then proceeded to show me, so he taught me how to use foundation, blush, eyeliner and mascara. Done with the lipstick, he asked me to look at myself in the mirror. I was transformed into a very hot young girl and it got me more excited.
"You will have to pay my services with a blowjob hunny bunny", Carlos was already pulling his pants down. He made me handle his big tumescent dark cock, until it was hard and then he showed me how to suck it. It felt soft, hard and warm inside my mouth, I really was beginning to like it. He made me kiss it and use my tongue to lick it like a popsicle. I tried to take it all in but i gagged several times. My come had been dribbling on my under wear and they were literally a huge wet, sticky mess. I pulled the minidress up and took off my shorts, while Carlos jerked himself and watched.
"Come here sweetie, sit on my lap while you give me a handjob. I do not want to come and mess up your make up... yet", I grabbed his cock, squeezed it tight and gave it a vigorous handjob. Carlos groaned and came in long spurts. But he remained hard as a rock.
"You are going to like this a lot, come over here and bend over the bed, I promise i won't hurt you." I was petrified, I never thought I would be turning into some kind of gay guy playing with cocks, but I obeyed. He lubed me well and stuck a couple of fingers in. It was very tight, so he kept playing with his fingers in my ass for quite some time. By this time I had already cum twice on his sheets and he looked quite pleased.
"Have you seen porn? ", he asked. I nodded. "Ok when I penetrate you, you are going to scream, moan and call my name like a girl, you understand?" That really got me hard again, I nodded eagerly. I felt a burning sensation at first, and he was in. He thrusted it deeply and I moaned. He kept going in and out for several minutes while I wailed and enjoyed my first fucking.
"Oh you scream like a cheap whore, and your hole is so tight,mmmm. Nothing like a young man's virgin ass..." He kept thrusting but now he was groaning. " I'm coming baby, tell me how my cum feels in you, aaaahhhhh!!!!" I felt him tense up and then I felt a warm gush, like an enema up my poop hole. He fell on top of me and pinned me down for a few minutes, with his dribbling cock still inside me.
After a while, I turned around and he smiled. "Your make up is still perfect, lovely" . I smiled, and he stuck a finger up my ass, and his cum came out in a rush. It dribbled on the bed and made a big puddle.Since then, I have had a thing for creampies and guys cumming in my ass. I like the semen seeping out of my ass and the warm sensation as it finds it's way down my legs.
"Hurry up and clean yourself, the party is about to begin", he said. And what happened in it is the plot of my next story ...

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Today Sir Dick Dickens came to my Shanghai office to negotiate cooperation. He was a tall gentleman full of British pride, the empire where the sun never set. 'I visited London one winter. The grey, wet and cold weather was so miserable.' Miss Yamaha, in a revealing western style long dress, interpreted for me. 'Well you see, General Tanaka, I don't live in London, at least not when it's cold and wet. I've been working many many winters in warm weather, cleaning up the old opium...

2 years ago
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Wartime Comfort House Diary Day 7 British Saugage

Maple would orally serviced my balls and soft penis to full erection if Cherry was feeding from her large engorged breasts. Miss Yamaha would service my other sensitive zones such as earlobes, toes and sole since she knew my sensitivities best. I would perform my thrusting exercise with either Yuko or Maple since my thin bride's love channel was still very sore. While Yuko lusted for my thick manhood any which way, I usually penetrated Maple from behind because her sad expression from losing...

3 years ago
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The United Kingdom of Zoo A fake BBC documentary seriesS11 E02 Chelsea Ferguson 34 from Chelmsford

This week, we start the show with establishing shots of the most boring suburban estate you could ever hope to see. Lots of ‘nice’ double story semi-detached homes, each with their own little square of grass and concrete driveway out front, separated from the public footpath by low brick walls. We can see a chunky, out of breath looking man walking along the street toward us, perky, elegant and mean-looking Doberman by his side ... This week’s host – the love-him-or-hate-him Cockney geezer –...

2 years ago
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Peggy Sanford a Worldly Woman Ch 07

Author’s note: I had planned to take a break from writing and submitting stories to Literotica when I reached 300 submissions. I know I said that when I reached 100 and again when I reached 200 submissions but many of you loyal readers asked me to continue. Many of you also sent me story lines and topics to write about, some more detailed than others. Recently I received an e-mail from Peggy Sanford who has written several stories for Literotica and if you have a Literotica log-in and...

4 years ago
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Peggy Sanford a Worldly Woman Ch 01

Author’s note: I had planned to take a break from writing and submitting stories to Literotica when I reached 300 submissions. I know I said that when I reached 100 and again when I reached 200 submissions but many of you loyal readers asked me to continue. Many of you also sent me story lines and topics to write about, some more detailed than others. Recently I received an e-mail from Peggy Sanford who has written several stories for Literotica and you can see Peggy’s profile and photo under...

4 years ago
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Businessman is Forcibily Transformed Into a Sissy

Businessman Is Forcibly Transformed Into A Sissy By Sissycuckold It was a warm summer's day when it all began; I was a successful 34 year old, businessman man, with a large house, flash car, and a beautiful wife. As it was a Sunday I was out for any early morning walk, having just finished making love to my 27 year old wife Lorna, when suddenly a large black car screeched to a halt just before me. In a flash 4 burly men jumped out and I was unceremoniously...

2 years 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
4 years ago
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The Bradford Family Saga Part 2

and shorts; his cock and balls swaying in front of him. Mary smiled, leaned forward again and nuzzled Carol's silky cunt-hair, flattening it out to the sides and exposing her sensuous pink slit to their view. Then she stuck her tongue up inside it. Carol groaned happily and bucked her hips. John was standing over them now, stroking his thick cock while he gazed dreamily down at his sister's inviting pussy. Pushing a finger back up inside Carol's dewy cunt, Mary explored its...

3 years ago
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The Bradford Family Saga Part 3

"My parents are celebrating their anniversary this weekend, and they're planning a family party. I'd like to take tomorrow off and fly down - if it's alright with you, of course." Lucy Parsons came around the desk and stood close to him. He caught a flash of tanned thigh as her skirt flap parted. "This must be a first. A new lawyer showing consideration for the firm." "Isn't that the way it's done?" "Not usually. Young lawyers are a fairly arrogant lot, and favors...

3 years ago
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Wartime Comfort House Diary Day 6

Throughout the day my thoughts kept coming back to last evening and my new local wife. I was keen to see her progress. Miss Yamaha greeted me warmly at the entrance of the Comfort House. 'General, you will again be comforted by your new local wife in peace. I have rescheduled those violent warriors to other Comfort Houses. Those coming in all received your order of loving tender comfort only. In fact I will schedule this Comfort House accordingly while your bride is here. The servants here...

1 year ago
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Wartime Comfort House Diary Day 8 Shemale

Dr. Takuchi was a classmate in the military academy. He was responsible for security of the secret 731 laboratory research in northern China. Although this top secret unit was never publicized, as a Commander General, I knew they researched all kinds of biological warfare and tested on the locals. Dr. Takuchi told me when he visited Shanghai last, 'We are mating all kind of animals with local females. Obviously with horse, donkey, Siberian husky, wolf, ape, monkey and then some others we...

2 years ago
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It8217s Not Just Love Making 8211 The Foremost Foreplays

Hello Everyone This is pradeep back again with the continuation of my first submission(IT’s NOT JUST LOVE MAKING),And people who does not read my first story please I request you to read my previous submission which was the first part,so that you can have a great brief introduction of the my story which im gonna share you all. So to say about me,I am Pradeep (Name Changed),From (Vadapalani) Chennai.Iam 21 years old and i am living in a private home.I am 5.9 with athlete body and average in...

4 years ago
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Sheriffs Forester

I was young for my post but I had been doing it as a deputy it for several years with the old sheriff's forester. My father was a baron but I was only a younger son so I was not going to inherit. I carried the heavy stag into kitchen and ignored the quiet that fell. I shifted it off my shoulder and onto the large butcher table, "I took this from a poacher Anna." She wiped her hands as she crossed the kitchen, "how long..." I snorted as headed into the Keep, "a half day." When I...

2 years ago
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A WellLived Life Book 6 Kara IChapter 10 A Trip to Milford Part II

September 1981, Milford, Ohio Kara came into the living room when the dishes were done and took my hand and led me to the den. We sat in our chairs, as her father insisted. “Did you put your mom up to that ice cream date?” I asked. “No! I was just as surprised as you were. I could tell that dad was really upset at her. And when you stepped in, I thought he was going to blow a gasket. You agreed with him and made him look bad at the same time. And then, when mom did that thing with the...

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