My First Time As A Crossdresser free porn video

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Its 18 months ago. I had now become comfortable wearing womens clothes. I had been experimenting for around 3 months. I gradually started to get more confident in both my clothes ......and without. I started to dress more like a slut. Short skits. Suspenders. Corsets. I had also become more comfortable with my body as well. My hole was tight as could be. Like everyone, i started with fingers, one, two .....before moving on to small toys. After a few months, i had graduated to a 9 inch dildo.....although i still struggled.
I felt so hot. So right.

I had been chatting with other CDs and men on both here and a swingers site. It turned me on SO much. I felt naughty.
One night, feeling extra confident....and with a little Dutch courage, i decided to take up one of many invitations to meet a man locally. We had been chatting for a while and he had told me how much my pictures turned him on. I felt hot.
I decided to meet in a public place. He suggested a small country pub close to him. At first i was sceptical. What would people think??
He assured me that it would be fine, its usually quiet on the week nights. I decided to go quite casual......no suspenders and corsets in this small pub ;) I choose simple black leggings tight top covered by a leather jacket.
On my way not once did i feel wrong or stupid. I felt right. I felt sexy. My heart was racing. As i had had a few drinks to relax, he offered to pay for a taxi for me. When i got in the taxi, i could see the the taxi drivers eyes on me. A middle aged man, looking at me, what was he thinking? Was my make up wrong? I checked. Nope it was fine. As we pulled up to the pub he turned to me and said ' Here we are love. Are you meeting your fella?'
'Something like that' i responded.
'Lucky guy' he remarked with a cheeky smile.

Woahhh! What just happened? I had gone from feeling judged to feeling hot and sexy.

As i walked from the taxi i looked back to see if he was still looking. He had his eyes firmly wrapped on my ass. Cheeky taxi driver :)
By now i felt super confident and strutted into the pub. He was right, it was quiet. Around 7 or 8 men spread out around the bar. As i entered i felt all eyes on me. This time i didnt feel judged. I was the only woman in this bar. My date quickly removed me from the centre of the bar to a quiet little table round the side.
'They'll all want you if you stand there' he joked.
We quickly got on like a house on fire just like on our online chats. He kept complimenting me. My big kissable lips. My beautiful blue eyes. My long legs. My hot ass. I felt amazing at this point. i was so turned on. As he was at the bar ordering more drinks, i could see him and the barman chatting about me.
What were they saying??
When he returned he told me the barman asked if i was a model, because of my height and legs.
Everything was feeling right at this point.

He started stroked my leg and kissed me gently. As i leaned over he grabbed my ass. He moved me closer to him and further out of view of the bar man. He began reaching down the back of my leggings, feeling my smooth ass, now and again pulling my cheeks apart. I saw in his trousers he was now fully aroused. This felt hot! He gently slipped a finger in me. At first it was a shock! Then it quickly became more exciting. Deeper he went. Faster. He tried two fingers but i was still so tight. My heart was racing.
I asked if he wanted a 'cigarette' outside. He said yes.

Neither of us smoked.

We went outside and he took me round the side of the pub. Away from the car park. Away from the lights. We was in a doorway, away from everything. Our kissing became erratic, our hands all over each other. He couldn't keep his hand of my ass.
I was stroking his cock through his jeans. Thick. Solid. He opened his jeans and out flipped his penis. Rock hard pointing at me. I kept stroking it back and forth, i lowered down to my knees. My nerves kicked in, this was the first dick i was about to suck. I teased the head with my tongue and big lips. Placing my tongue on the head and pulling the foreskin over it really turned him on. I managed to get all the cock in my mouth and sucked all the air out whilst pulling it in and out. He said he was gonna cum in my mouth if i carried on like that...... so i did, harder and faster. He grabbed my head and pulled it closer, his balls now on my chin, he began to shake and let out a massive groan and shudder as he exploded in my mouth!

He slumped back as he caught his breath. I licked the rest of the cum of his dick and squeezed the last drops out into my mouth. He continued to shudder as i did. As i got up to compose my self he pulled my leggings down and turned me around. 'Your turn' he said.
He pulled my thong down and leaned me forward. He spread my cheeks apart and started licking my hole. This was so hot
The licking turned to thrusting his tongue in and out. I almost came there and then!

It had gotten late and i expected him to go home, especially after he'd emptied his load. But he said he wanted more before going inside for a word with the barman.

I felt amazing at this point. Wanted. Slutty. Almost used.

He came out and took me to another side door and told me he had rented a room for the night of the barman.
I felt dirty but excited. He quickly dragged me up stairs to the room.

It was dingey. Basic. But did it matter? No. He quickly got naked and took my clothes off just as quick.
I was quickly bent over the side of the bed. The tongue was quickly in my hole again. All over. I was so turned on. After around 10 minutes of this amazing action i felt his body and noticed he was hard again. I grabbed him and threw him on the bed. As i went to suck his cock again, he pulled me onto his face. My first 69. Amazing feeling of a hard cock in my mouth and a tongue in and out of my hole. It was getting hotter and hotter. I sat up and began to jump on his tongue.
He said he needed to fuck my ass. I was so excited. I turned around and tried to sit on his cock. I managed to get the head in but my hole was still to tight..... i quickly jumped off and got the lube out of my bag. This time it eased in gently but was still tight. I began to move up and down on his cock, faster and faster. I was grinding on it by now. He was moaning with anticipation, i knew he was close to cumming again. He turned me over and began to fuck me doggystyle. Fast, fast, faster. He pulled out and let his cum splash over my ass and back.

I stayed the night and we had a further few sessions. I phoned a taxi in the morning. I got ready and as we said our goodbyes i walked over to the taxi with a satisfied look on my face, i realised I had become a slut. A slave to the cock. A lover of cum.

As i got to the taxi i realised it was my driver again.
'I had a feeling it might have been you that's why i took the job' he said with a big grin.
I laughed and got in the taxi.
I was now a slut with a taste of cock and i was in a car with a guy who i know wanted to fuck my ass.......
.........but that's another story ;)

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Hi this is hotslutaddy back with my friend ishika’s story. Hi this is ishika. Those who have read my first story “lost virginity from behind” in virgin archive should know that I am a cross-dressing bottom gay.It had been 8 months till that incident and I had completed my schooling. Kartik had become my boyfriend and I love him more than my life. Now I was in a college in a nearby town and I lived at a house on rent. I lived alone there so I had an almira full of female clothes and make up.Most...

Lesbian
2 years ago
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The 2nd Halloween for a Boy Dressed as a GirlPart 1 A Blissful Young Crossdresser

5th Grade. 11 years old. Dressed as a girl again on Halloween. As a cheerleader. My next old sister's cheer uniform. Her idea. Her bra and panty too. My special "Boob" socks to give the appearance of breast. A discussion I had with my next 2 older sisters. How ample were my false breast to be? Normal size for girls my age? Bigger for my ego as a girl, for all the times I have dressed up with them through the years? Dolly Parton size? Because my 2nd oldest sis Joan, made...

3 years ago
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SALLYS RELUCTANT CROSSDRESSER

CHAPTER ONE                Sally and Dave had been dating since high school, it was a turbulent relationship, and at this moment in time they were having a few arguments, Sally called them dicusions. They were both nineteen and in love with each other, and both were jealous and possessive of each other. Sally was the one with the ideas, and Dave let things fall into place as he could never emulate her suggestions. They were sitting in the lounge of the flat they rented, they were not married...

1 year ago
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The hottest crossdresser

I was drinking with my friend Curtis one night as his girlfriend Jane was out with her friends having some drinks. The topic turned to cross dressers, as I had had let it slip, that one time I mentioned to him, I had dressed as a girl a few times when I younger in my moms clothes, and it felt great. He asked if I had any girl’s clothes at home that I wear from time to time, which I reluctantly said yes. With that Curtis asked if I would wear some of Jane’s clothes to see how I looked. “Sure,...

Bisexual
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...

2 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...

4 years ago
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My hottie night with two crossdressers

When I was 27 years old and single, I really liked going to shows at night, to nightclubs, especially when it came to beautiful women. One day I went to a transvestite show and was fascinated.These men dressed as women groomed themselves more than any of the women he knew; her wardrobe, her makeup, even her movements, were more feminine than any woman's.I started visiting an exclusive nightclub, where every night there were transvestite performances imitating well-known artists and singers.I...

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...

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
2 years ago
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Daytime friends nightime lovers

She wanted to remember. The hookah was a beautiful piece. It stood at 4 ½ feet. Dark red… it always was her favorite color. This hookah was her personal prize. It only had one hose, one smoker. She pulled the airtight box from its hiding place and opened the lid. Once released, the heady aroma drifted, tickling her nose. The new batch of bud was a dark green, but the crystals were so thick it turned everything pastel. Breaking it apart just enough to smoke easy, she arranged the weed in...

3 years ago
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Daytime friends nightime lovers

Introduction: While a few details have been tweaked, this story is as close as I can remember it Prologue She wanted to remember. The hookah was a beautiful piece. It stood at 4 ½, feet. Dark red&hellip, it always was her favorite color. This hookah was her personal prize. It only had one hose, one smoker. She pulled the airtight box from its hiding place and opened the lid. Once released, the heady aroma drifted, tickling her nose. The new batch of bud was a dark green, but the...

4 years ago
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Sandy and RandyChapter 2 Daytime Funtime

After the close call and excitement, in more ways than one, of that first night together, Sandy decided they better cool it a bit so Mom wouldn’t get suspicious. Mom also went back on day shift, 8am – 8pm, so bedtime was less private, but days were not such a problem. Randy tried to act normal around Mom and of course, around Sandy, but he did have some issues like being quieter and more protective. Mom just thought he was getting older and closer to starting into puberty, especially now...

3 years ago
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FaceTime with Ann Next Door

I never FaceTime. I'm not a adolescent girl. I don't need to see your face when a simple text will do. Call me an old bastard, get-off-my-lawn type, but that's the way it is. (By the way, I'm not that old).So when that mechanical beeping emanates from my phone that someone wants to FaceTime me, it's definitely out of the ordinary. Especially when it's 10:30 on a Tuesday night. I got to my phone and it said "Ann FaceTime video."Well, this was different. Ann Next Door and I been fooling around on...

2 years ago
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Halftime Stranger

It was a warm October night and I was at a college football game with a few buddies. Throughout the first half of the game, I looked to my right and there was this hot sexy bald guy 3 sections to my right. He had huge arms and was wearing a black wife-beater and jeans. We kept looking at each other and at each time, he would show that bright smile of his.At halftime, I went to the restroom and used one of the stalls, luckily I was the only one in the bathroom. As I opened the stall, he was...

3 years ago
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Summertime In Colorado

Summertime In Colorado I absolutely love summertime. The hotter it is the less the girls wear. Instead of long jeans they wear short shorts. Instead of full blouses they wear skimpy tops. Coats are strictly out of the question too. Bikinis are popular even if it is just the top half with a micro mini skirt. Like I said I absolutely love summertime. Girls of all ages are wonderful to look at. Touching them might be a different story but looking at them is still legal. The problem...

3 years ago
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Summertime Blues

Summertime Blues Author's Note: This is an old story of mine which I self-edited using the great suggestions I been receiving. I will go back and edit it more. I want to see how well I could implement the suggestions which I got. Also, I want to give a thanks to all the people who had help me in my writing. It was a bright sunny Saturday afternoon in July yet it was raining in Joe's mind. This was for Joe was having a run of the mill bad day so he headed to the bar for a drink. He...

3 years ago
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FaceTime surprise

I have a new job working away and I bought an iPad to keep in touch with the wife, it’s great seeing her when away I miss her so much so it’s great when I’m bored in my room. Jane and I for years have spoke about sharing? But she never comes through, it must be 4 years now we have had the same conversation about it and it’s always the same answer maybe! Jane is great in the sack she knows how to please, I keep telling her she needs to give it out cos it’s going to waste on me as I only last...

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