CL Memories #1 - Crossdresser (True Story) free porn video

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I used to get a lot of fun out of CL. I'll post some short stories about some of my experiences there. I sure do miss it. This happened about 10 years ago. I was divorced and living alone, and playing whenever I got the hots and had a good opportunity.

I checked CL one weekend night to see if there was any fun to be had, and found a post from a crossdresser visiting a nearby city and looking for company. She (I'll use that pronoun here) had a room in a local motel for the night. I responded to the ad with a nude of my body, and she wrote back a short while later telling me the motel and room number. The motel was one of the less expensive chains with outside entrances to the rooms, but a decent and safe place. It was later in the evening, after dark, so I put some condoms and lube in my jacket pocket and headed over.

I parked in the back, well out of sight of the street, and walked to the room. She answered my knock dressed in sexy lingerie, wearing a blonde wig. She was no spring chicken, probably in her early 40s, but I was in my 50s, so I had nothing to complain about. She was shorter than me, and very slender, with a nice fuckable ass. She was in black - bra, stockings, and garter belt, with no panties. Her small hairless cock hung flaccid between her thighs.

When I got inside the room there was another man there, naked from the waist down. I didn't mind sharing, so I sat down to watch them get back to what they were doing. He was younger and bigger than me, but visibly smaller where it counted. She sat on the edge of the bed, got him between her legs, and went to sucking his cock. After a few minutes he was fully hard, and she put a condom on him, then got up on all fours.

She moaned as his cock entered her. He slid in slowly, going balls deep in her ass. They were obviously enjoying themselves. I undressed to join in. I got completely naked, leaving my clothes on a chair in the corner. Stroking my cock, I moved to the head of the bed in her line of sight. I didn't want to interrupt them or spoil his fun, just show them that I was ready if they wanted me to join.

It was her party, and she was moaning her pleasure as he pounded her boy-pussy. She saw my erect, shaved cock, and eventually motioned me onto the bed. I lay down on my back and slid down until my cock was under her face. She was really into what she was feeling at her other end, and slid her mouth down over my bare cock. She put one hand at the base and stroked it with her hand and mouth together. I just lay back and put a pillow under my head, and enjoyed his thrusts pushing her mouth down on my dick. The other guy smiled - I guess he was enjoying the spit-roast as much as I was.

He fucked her ass for 10 minutes or so at a varying pace, then began to speed up his thrusts. She was holding my shaved balls as she sucked me. I could see the look of concentrated pleasure and impending orgasm on his face. He was holding her hips and pounding as deep as he could go. Finally he grunted and pulled her tight against him as he filled his condom with cum. I was in no hurry as long as my prick was in her mouth. I just watched as he pumped a few more times, then withdrew and went off to the bathroom. He came back within a minute or two, and started dressing, and she got off the bed to shepherd him to the door. I told him I didn't mind if he stayed, but he said he was done.

Then he was gone and it was just us two. I got up and got a condom out of my jacket, then asked her to get on top and ride me. I slipped the condom on and lay back. She got a bottle of lube and covered my rod with it, then knelt over me and slowly slid down onto me, taking me all the way in within a couple of strokes. We fucked that way for a few minutes, then I wanted on top. I rolled her onto her back without slipping out, put her legs over my elbows and began pounding down into her tight little hole. It wasn't too long until I was cumming. I let go of her legs, lay down on top of her and kissed her neck while I enjoyed the feeling of cumming in a tight hole.

After a few minutes that way I got up and went to dispose of the condom. I came back into the room and she was lying where I'd left her, on her back in the middle of the bed. I sat down to enjoy the afterglow and we chatted a little. She told me where she was from, and that she came to town every few months to get a room and live out her gurly fantasies. I moved over to the bed with her as we talked and began caressing her boy parts. She didn't start getting hard, so I assumed that reciprocation wasn't in her playbook for the night. I, however, did start getting hard, and asked if she was up for another round. She smiled and said yes.

I pulled another condom out, then went back to stand by the bed while she sucked me to a full stand. When I was ready I slipped the condom on and got her on all fours. I slid right into that wonderfully tight spot and started fucking. Soon I was driving her forward across the bed. We wound up with her flat on her belly, me on top of her fucking deep into her. Being older, I just couldn't get to that second cum. Eventually I just lay on top of her for a few minutes, enjoying her tightness. Then I got up, disposed of the condom, and started getting dressed.

When I was ready, she guided me to the door, and kissed my cheek. I told her to keep my email for the next time she was in town, but I never heard from her again. I sure would like to.

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Initially i use to wear my sisters dresses or my mothers bra,panties,saree,blouse,petticoat and see myself in a mirror and admire myself. Though i wasnt so good at makeup, i used to apply lipstick and put some jewellery items. It couldnt make me look like a girl but the feel of women’s clothes turned me on. And then i used to masturbate after my every crossdressing session, thinking about being fucked by a guy. But then as i grew up chances of being alone became less and i had to kill my desire...

1 year ago
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firsts time Im seen as cd crossdresser

From a young age I liked dressing up in womens lingerie and clothing.... as I got older I grew up over weight a little and more so the older I got..... by the time I was I was in my late teens I had nice size breasts....nice enough to fill a bra. So worked up the courage to buy some lingerie online and when I received it in the mail I was so excited. I couldn't wait to try everything on.... I had brought a white lace bra, matching panties and white suspenders and stockings.....I tried them...

2 years ago
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Telling Mom Im A Crossdresser

When I was younger, my dad had passed away leaving only my mom and I. She is 45 years old with long brown hair, bright green eyes and stood about 5'10" in height. She is also a fairly busty woman with a 30DD chest with about 35" hips and in pretty good shape for a woman her age. I had been crossdressing for a few years and my mother had caught me a few times wearing her clothes. The first few times she had a surprised look on her face and left. However, after a few times she seemed not to care...

Crossdressing
4 years ago
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Picking up a Crossdresser in a Bar

This happened about 20 years ago. The basic events are completely true, but in those days I drank a lot, so I don't remember many of the details. For the purposes of a good story, I made up a few things to fill in the blanks in my memory.It was a weekend, and my wife had taken the k**s to visit her father 400 miles away. I was alone at the house, and I knew an opportunity when I saw it. At the time we lived in a small city, and there was a gay bar in town that advertised a weekly drag show on...

2 years ago
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Crossdresser Stories 8211 Assfucking in panties

I have been ‘mildly’ crossdressing for over a year now. I say ‘mildly’ because I am not into full feminization, I just love the feel and look of lace panties when they are hugging a good looking cock, not to mention the taboo. I have taken to wearing stockings too which feel amazing, it’s like having your whole lower half caressed persistently. I have thought of wearing a bra but, although I can almost imagine how amazing it would feel, I don’t think men look...

1 year ago
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Telling Mom Im A Crossdresser

When I was younger, my dad had passed away leaving only my mom and I. She is 45 years old with long brown hair, bright green eyes and stood about 5’10’ in height. She is also a fairly busty woman with a 30DD chest with about 35′ hips and in pretty good shape for a woman her age. I had been crossdressing for a few years and my mother had caught me a few times wearing her clothes. The first few times she had a surprised look on her face and left. However, after a few times she seemed not to care...

3 years ago
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crossdresser confession part 1

I really loved my wife; she was the most beautiful creature I have ever known. Tall, brunette and the longest legs you have ever seen. Myrtle's beautiful face is framed by her gorgeous brown hair. She was about 5'8" and had a great ass. Her curves were soft and very feminine, not a big chest but nice and perky tits I loved to play with.She would drive me crazy when she donned a pair of pantyhose and heels with a short skirt. She didn't know it, but she would not have been able to keep my hands...

Crossdressing
1 year ago
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The start of my life as a submissive crossdresser

I am a bisexual cross-dresser/sissy and have been enjoying my life as such for many years. It all began for me when a friend asked me to look at some of his 'girlie' magazines.We went up to his bedroom and looking through the magazine got Chris really excited and he got his cock out and started to masturbate. I couldn't take my eyes off his cock and I slowly reached out and touched it and when he removed his hand I curled my fingers around his erect shaft and began to slowly wank him.I just...

Crossdressing
1 year ago
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The Next Night Crossdresser Part 2 of 2

I woke up early from the sunlight shining through the windows. We’d forgotten to close the curtains when we collapsed into bed last night. Jenny was already awake and watching me. ‘I was just about to wake you up with a blow job,’ she smiled.‘Funny, I was thinking of doing the same to you!’ I laughed.Jenny kissed me then turned around in the bed to lay on her side so our cocks were facing each other. We both had erections already. I shuffled close and took her long cock in my mouth, closing my...

Crossdressing
3 years ago
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Simran A Crossdresser Part 3

After that rather eventful evening with Ram, I opened up to my fears and inhibitions. Now performing on cam or coming out dressed in front of an online crowd was something I could do easily. I still covered my face, since I wasn't yet ready to reveal my identity. As far as I remember, it was a couple of weeks after my interaction with Ram that I heard a commotion outside the house. I went downstairs and looked through the window, and what I saw was astonishing. People were running, screaming...

Crossdressing
1 year ago
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First Time With A Crossdresser Part 1 of 2

I’m Scott, 36 years old and recently divorced from my wife of 12 years. It was an amicable split with no kids to complicate matters. We sold up, divided everything two ways and went on our merry way. Our sex life was good and regular but a little boring. We stuck to the same three positions – missionary, her on top and spooning. I’d give her oral but she wasn’t that keen on going down on me and her facial expression when she was blowing me put me off asking for it! I’ve never needed more than...

Crossdressing
3 years ago
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Memoirs of a Crossdresser Chapter 1

My True Story Chapter 1: I was a kid when I first discovered women's underwear. I loved the way it made me feel. I had a friend who I'd play the normal games that kids play with, and I would always be the girl character. We were children, so nothing out of line went on, but even at a very young age, I had felt an attraction to femininity. There was something that made me feel like I should be the damsel in distress, waiting to be rescued. I remember wanting to feel girly. As I got older, my...

Crossdressing
3 years ago
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Crossdresser Business Trip to South India

Sheila Boy Mon, Jun 3, 11:09 AM to meHi All.Guess you all know i am a bisexual guy and i love to crossdress whenever i get a chance and i am alone.Well as it happened I was on a work trip to chennai and bangalore some time back. It was not a planned one and my boss told me in the night that i had to go and all arrangements have been made. I reached by the afternoon flight, took a cab and checked into the hotel booked by the office. After completing all this and...

1 year ago
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Simran A crossdresser part 2

Well after my little adventure in the bathroom with my mom's panties, I went out for a couple of drinks with my friends. But, in spite of having company, the only thing that kept playing in my mind was the feel of those satin panties and how horny I had felt in them. All I could imagine was getting back to the house as soon as possible, before my parents returned, and having one more go at it. I returned around seven in the evening. Since my parents had a convenience store, I knew they wouldn't...

Crossdressing
1 year ago
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Simran A Crossdresser Part 1

Well I still remember the day back in the summer of 2010. I had just turned sixteen and was introduced to the world of cross dressing in the most fantastic way possible.I guess introductions are in order. I am Simar, an average guy from India, who goes to college, has a great family, great friends. Well something you gotta know first. My family follows sikhism so I have a beard, a mustache and body hair which I cannot remove because of religious reasons. But it is a blessing in disguise because...

Crossdressing

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