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Penthouse Letters Crossdressing

curious12334	Tall athletic male curious to meet a crossdresser or crossdressing couple, or also a transgendered person I am a virgin with bisexuality but i'd love to suck a nice cock or try it on a crossdressing male, that i would love to get naughty on webcam and would love to meet someone take it slow with me im nervous lol Send Mail IM
Imsoohorney4u	I am a hot and horny crossdressing slut who just loves wear the slutty clothes, pantyhose, nylons, silky panties, miniskirts and cum fuck me heels and boots. I am not into men, just other CDs like myself and especially real women, if your are a babe and are not into crossdressing, no problem as I can be as macho as the best of them. To put it simply I just plain love sex and I want as much of it as I can get, so cum on you little hotties and give this horny slut a test drive as I am sure you will cum back for more. Send Mail IM
Join To View joey59	51yo, 10lbs overweight, and balding! lol. Folk musician type....New to crossdressing and loving it! I need a teacher and partner(s). I love 69 and need a top. Would love to have a crossdressing couple 3-way. I'm wide open. Oh! I have lots of toys, including a great Fleshjackand I love using it on others. Send Mail IM
mayflowerscd	I am a crossdresser from Virginia. I started crossdressing when I was 19 .I have a goal to show to the world that Crossdressing is a unique and wonderful lifestyle I love dressing up in lingerie or wearing panties, high heels, Make up, Heels, Perfumes and Jewelry.... love chatting Send Mail IM
ocguy	I am a recently divorced guy. As you might guess, the crossdressing had everything to do with it. It was my own fault. I tried to hide it and I should have been honest from the beginning. She really loved me but I lied too many times. So I'm done lying to myself or anyone else. Other than my fetish, I'm a pretty normal guy. I only like the crossdressing as part of having sex. And only occasionally. I have always enjoyed hot straight sex as well. I have a degree in Economics, I played college baseball, and I still like to exercise regularly. I've always been a somewhat health conscious person but not a fanatic (I don't talk about it much). I'm not interested in trying to change anyone or trying to get them to think like me. I'm very easy going and can adapt to most situations without a lot of effort. Send Mail IM
SissyBoyAshley420	I'm a very laid back person I haven't come out about my crossdressing to my family or friends but I enjoy it very much often times I'll wear panties to work just because i have a special evening planned but I have never been with a male and never been open about my crossdressing with a female but I would like to try something with a BBC... Or a white boy with a big "package" also wanting to try a strap on with a female Send Mail IM

krylin	The biggest turn-off for me is the lack of replying back. When sending a 'first contact' letter I am very polite and ask them to check out my profile to see if they may or may not be interested. Out of the many, I got one reply back saying basically, 'no thank-you'. That's all I needed. Never bothering the couple again. When you get no replyback you wonder if they ever got to begin with, which buggs the hell out of me. I don't want to write again and become a problem for them or to appear pushy. Now I look at the bottom of their profile to see if they reply to any of the letters that they receive. If they never contact anyone initially or reply to any of the letters they get, I don't write to them at all. It's their loss if they don't want to realize their fantasies. Thanks for hearing me, Otherwise a great site, Krylin Send Mail IM
Join To View relaxandenjoy	Mods, I didn't get back to this thread to notice your response until recently. I could have chosen my words better, and in doing so not sound so harsh. I'm just not a fan of having my words automatically replaced or half replaced by a cute symbol. I prefer the letters to remain letters. I didn't mean to sound like I thought there was someone reading our mail and manually editing anything. I knew that was not happening. I would also still like to see a systematic change that would allow us to add HTML or at least links. I couldn't say how to accomplish this, but I do know it is possible on many forums I belong to. Regardless, this is a great site. Keep up the good work! Send Mail IM
harpofog	I was 16 staying with relatives outside of Denver for the summer. In the next apartment to where I was staying was a single guy and his cute 18 year old son, Nick. My 17 year old cousin was busy chasing after his girlfriend all day so I had the apartment to my self pretty much all day while my aunt and uncle where at work. I had been in town for a couple of days and decided to go for a walk and check out the area. At the corner drug store I saw Nick standing in front of the magazine stand and saw he was flipping through the men's magazines. Back in California, I had a girlfriend who would bring her dad's Penthouse magazine over and we would read the letters which would get us pretty turned on and always ended up with us licking each other's pussy to climax. I didn't have much experience with a guy, just some heavy petting, but wanted more. It took all my courage to walk up to him and say hi. He tried to jam the magazine he was looking at into the rack, but it fell on the floor. I picked it up for him and told him that I liked the letters as I handed it back to him. It was clear he was embarrassed, so I just smiled and walked out. I almost ran back to the apartment and stripped my clothes off and was laying on the bed playing with myself when I heard a knock on the door. Looking through the peephole I saw it was Nick. I grabbed one of my uncles shirts on the sofa and put it on before cracking the door open. The shirt covered me to mid thigh and I only had a couple of the bottom buttons fastened, so it was pretty obvious that was the only clothes I had on. I was pretty much completely developed by then, so their was quite a bit of cleavage showing along with my nipples being hard. He tried to apologize for his behavior, but he was having trouble with the words along with the fact he was staring at my chest. I figured it was too good of a chance to pass on so i asked if he wanted to come in and get out of the hall. He nodded as I opened the door fully to let him in. He sat at one end of the sofa, so i sat in the middle with my legs curled up underneath me. He shifted a bit and I could see he was trying to hide his hard on. I came right out and asked him what magazine he liked best and that my favorite was Penthouse because the pictures were more explicit than the others and that I enjoyed the letters. He nodded and said he liked that one too. I don't remember much more talking before I stood up and grabbed him by the hand and pulled him down the hall to my room. I closed and locked the door and asked him if I could see his cock. He stood staring at me, so I unbuttoned the shirt and took it off. He said something about how beautiful I was, but he still wasn't moving so I took his hands and put them on my boobs and starting undoing his pants. There wasn't anymore hesitation from him. He quickly got out of his clothes and I pushed him onto the bed on his back. I stared at his cock before reaching out and touching it. He was really hard and the feeling of it in my hand was such a huge turn on. I played with it for a few minutes with my hands, admiring it as I pulled on it and playing with his balls. I slid up between his legs and was looking him in the eyes as I ran my tongue over the top of it. He was breathing pretty ragged as I slid him into my mouth. It was only seconds before he said he was going to cum. I held him still in my mouth as he shot his cum into me. With one hand I squeezed his balls slightly and he came again! I couldn't believe how good he tasted! I swallowed everything and kept licking and sucking on him, wanting more. I was able to get him to cum in my mouth twice more before he told me it was my turn and rolled me onto my back and pushed his tongue into my pussy. He followed my directions on how I like my clit sucked and how to move his finger inside me. I was so wet and turned on it didn't take him long to make me cum. We were careful about the time so that we didn't get caught. The summer turned out better than I could have imagined since we spent almost every day playing with each other. Next post I'll cover the first male-male encounter I saw. Send Mail IM
Join To View crushed	Hi guys; it's me Max is typing this for me since I can't use my left arm. (Teri is bombed on pain killers-I am writing word for word so you can enjoy this too ) I want to be thanking everyone for their letters, Max is has been reading all of the letters that my e-mail been in (sorry she is so looped I can't stop laughing so I am missing some of it) my e-mail says you wrote me so max is reading and answering. thank you for liking me and sending your e-mails. I will be fine very soon then we can chat again. ok I am going to sleep again love you Teri absolutely had to say thanks. I think I need to watch her meds closer. lol, she is now on her back with her legs up in the air telling me she needs to shave her legs--ok that's it she just fell asleep talk to you all later Max Send Mail IM
Freesafety123	This guy could write for Penthouse Forum......does that even exist anymore??? it makes the blood flow, doesn't it??? Send Mail IM
Join To View RayRayDoner	1970 something. I’m sure it was all over the pages to a playboy, penthouse or hustler magazine. Send Mail IM

Crossdressing on Bisexual Playground

Crossdressing on Bisexual Playground

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