Fun With A Cross Dresser free porn video

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I had a really good experience with a cross dresser yesterday. A mutual friend had recommended him after enjoying his services so I got in touch and he immediately responded by inviting me to go and meet him. It was most enjoyable. I have never been with a CD before but he seemed okay. He is late 50s and very slim. It was really quite strange. He came to the door in a dressing gown and invited me into the lounge where he explained how he had got involved in all of this by dressing up in his wife's underwear when she was out. He said that this was a real turn on for him but eventually he got so hooked on it that he could not perform unless he was dressed up. Eventually, it all led to the breakdown of his marriage about 5 years ago.

Anyway, he said that he can now only have sex if he is dressed up and that he needs to be totally dominated and feel used. I was getting very excited at hearing all of this so asked him to show me what he had got on under the gown. I was really surprised by what I saw - he had very exotic black underwear on. A lacy bra and panties, matching suspender belt and black stockings. He had a slight filling within the bra and his cock was standing to real attention within the panties. He asked me to remove his bra and to play with his nipples. When I took off his bra, I was pleasantly surprised to find that he had the makings of very small breasts. He told me later that he has achieved that by taking some hormone which they use as a homeopathic treatment for preventing or help treating prostrate cancer.

I tweeked and pulled on his nipples and they became quite hard. I then sucked on them for him and also played with his tits. By now he was really excited and he asked me to take off his panties. I did so and then spent some time exploring his cock and balls. I nibbled his foreskin, his head and his balls in turn and really got him going. By now, I also had a raging hard on and he told me to strip off and use him in any way I wanted. I told him to kneel on all fours so that his tits were more accentuated and gave them some more attention. I then moved behind him and pressed my cock between his arse cheeks and had a short bum wank by sliding my cock up between his cheeks. I also continued to excite him by some gentle stroking of his cock, massaging of his balls and gentle fingering around his arse-hole.

Having got him really excited, I then told him that I wanted to watch him wanking himself so that I could learn what he liked and how he liked his cock played with. I told him I wanted him to bring himself off so that I could see his spunk erupting from his cock and so that I could then see if I could get him hard again. Although he looked a bit disappointed, he did as he was told and with a few short, sharp strokes was soon climaxing. I then told him that I really wanted to continue using him for my pleasure.

I asked him to cover my cock in his spunk and then told him to take me in his mouth so that he pleasured me while at the same time tasting his own produce. Once he had licked me clean, I then played with him again until I got him hard and then I sucked him. I found it quite a turn on to be able to massage his stomach and legs underneath his suspender belt and stockings. I then had him on all fours again and used his arse cheeks for some more bum wanking before turning him onto his back so that I could rub my cock on his. By now, I was bursting for it so I gradually moved up his body getting some pleasure by sliding my cock under the front of his suspender belt and rubbing it against his stomach. I then moved up to sit astride his chest. I slowly started to wank myself until I climaxed by shooting my spunk all over his face and into his mouth.

Can’t wait to enjoy him again.

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When I was 12, I went to shop for shoes with my mother. I would walk around the store, making my mother laugh out loud. The onlookers at the store, would often look at me in astonishment and wonder, “How is this little boy handling pencil heels so well”?. My mama knew it back then that I was born different and she fought the world to make me who I am today, a proud cross dressing gay male. It was my first prom and I was nervous. I was worried that I will be made fun of at school, but my mama...

Cross Dresser
2 years ago
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An arrogant husband gets his comeuppance on a cross country trip with his beautiful wife of twenty years and their passenger a young black man

I couldn’t help staring at it. It was not only the biggest cock I’d seen, there was an aesthetic quality to it that begged a lingering look. Veins coursed over thick black flesh ending in a perfect golfball sized half-dome. It had to be eight inches long and, Lord Almighty, it was still soft! The first word that jumped to mind was “superior” I was staring at a superior penis. The kid’s voice snapped me back to reality. “Wanna hold it for me, Prof.?” he...

1 year ago
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Fundraiser Fiasco

PART 1 - FASHIONABLY LATEIt took me longer than I planned to get ready. It took me forty-five minutes to style my newly highlighted hair in the loose curls I wanted to go perfect with my outfit I bought for the occasion: a baby blue Valentina cashmere short sleeve sweater and a white Marc Jacobs pencil skirt to match my six-inch white Louboutin heels.Despite the skirt having a flared hem, the lycra-cotton material hugged my hips and thighs. With every step I took, the skirt pulled taut,...

True
2 years ago
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Fundraising Auction

Fundraising AuctionI work in a large company and every year we have a large fundraising event. If you don't have the money to contribute, you can also donate any goods or services. All of the funds go to local charities, so it helps everyone. The event is held at a large hotel, and there is a large silent auction of donated items. There is also plenty of food and drink, although it is a cash bar and the profits go to the different charities.At the time, I was just making ends meet with my...

Spanking
3 years ago
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Confessions of a Sex Crazy Cross Dresser Part 8

Chapter 15: Dangerous Duo I woke up the following morning to an empty bed. I went to the bathroom and when I came out there was a knock on the door. I looked out and saw Peggy with a bag and two cups in her hands. Upon opening the door, Peggy came inside and placed the drinks and bag on the table and gave me a kiss. “I thought you might want some breakfast,” she said. She had on a pair of white shorts, a light blue tank top and her sneakers. “I brought coffee and donuts.” This girl might be a...

Crossdressing
1 year ago
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BiSexual Cross Dressing Cuckold

My bride to be cheated on me as a girlfriend, again when she was my fiancé, and thereafter as my hot wife for 23 years. I guess the stars aligned for us.Me-For some reason I turned to slutty, tight black satin gloves in bed, without ejaculation, a year before I accidently discovered masturbation and gushing in the bathtub. I was 12 the first time I ejaculated, rubbing my cock with slippery shampoo. An overwhelming surge of floating and pleasure washed through my virgin boner as my sudsy palms...

3 years ago
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My Road to Crossdressing part 2

I had dressed up since I was a teenager but it was only occasionally. Usually, it was just lingerie and it was always for me and just for masturbation. It was about ten years ago that I decided I wanted to go further and start using makeup and breast forms and wigs etcetera.Quite by chance one day, I rang an old friend just for a chat. I found out that he had rented his house out while he was travelling. The person on the other end of the line was a woman, or so I thought. We got talking and I...

Crossdressing
3 years ago
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The twin sisters of the cross dresser policewoman

(This post is a fictional story on a bondage forum in China, and I am the prototype of the story. I just translated it into English. The copyright belongs to the original author, and the portrait right of the photos in the original link belongs to the original author and me)In the middle of a gloomy and horrible room stood a woman with a shawl. She was wearing a sexy red cheongsam, a pair of sparkling flesh-colored stockings like cicada wings wrapped around the beautiful woman's slender legs....

4 years ago
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AutoRide Made Me A Cross Dresser Whore 8211 Part 1

I’m a male, and cross-dresses occasionally in private. After cross dressing I get hard and then get off rubbing my dick against bed. Sometimes I post my cross-dressing photos online and get excited by comments and chats. I fantasizes about being seduced/forced to cross-dress and made to serve like a whore by dominant stranger(s). I’m darkish brown, lean. Has little hair on my upper body. Thin. Have slender arms. Soft face. And thick lips. And finger thick but long. My butt is rather fine and...

Gay Male
1 year ago
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Highlights of the Day A Jo Cross Story

A LITTLE PSA FROM JO: Kirsten has finished writing her update on the day for you all, but I've just taken the netbook from her to add a little something of my own. I want to thank you all for taking an active part in her adventures. The truth and the fantasy. If I sometimes seem a little pushy in the feedback comments about the targets I set....That is because I can only have Kirsten at certain times and days because of work, personal lives, etc. And as I read your amazing suggestions, I...

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