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Old 12-29-2009, 05:37 AM   #26
twiggystig
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this was a hot thread. hate to see it die. anybody else have any first-time stories?
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Old 01-08-2010, 10:40 AM   #27
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My first cd experience with someone else, I went to this Italian guy's flat. I stripped and dressed in the outfit he provided - high heels, fishnet stockings, thong, miniskirt, black lace bra. I roleplayed his new slutty girlfriend. It was so hot when he fondled my ass. That night was also the first time I had a cock in my mouth, and he also fucked my ass.
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Old 01-08-2010, 07:01 PM   #28
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My first time out as a woman I arranged to meet a guy I met on a dating site.I had a bath and put on a corset,thong and stockings then put my ordinary clothes over the topand carried my boots,dress,falsebreasts and wig in a bag.We met in a bar then went to a gay club.I felt so horny dancing and kissing him.We booked into a hotel and he went to the bar foa bottle of wine,while I went upto the room and got ready.we started kissing and I felt so horny and got so hard.I went down and sucked him and he was the first guy to fuck me.He took my dress and thong of put me on my back with my feet on his shoulders and had me.We spent the night together and he had me twice more.Since then I love going as a woman
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Old 01-12-2010, 09:45 AM   #29
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great experience!!!!
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Old 01-12-2010, 10:39 PM   #30
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I have never dressed but used to have a jo bud that did. One night he came over and when he took his sweats off he had a nice pair of panties on and a lacy bra. His cock was already hard and looked so hot in the panties. I could not wait to get my hands on it. We both shot cum in the panties for him to wear back home.
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Old 01-14-2010, 10:15 AM   #31
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hello funone and all who read this post or any other of you beautiful people who read this post or any other ,My gurly name is Cheryl, and I have been dressing gurly on and off my entire life since age 7 my dad dressed me in my next oldest sisters cklothes to get me to stop wetting the bed he did this a cpl of times a month over a 2 year period ....Well it worked I stopped wetting the bed LOL but started dressing more ..and more and I got caught by all of my sisters ,Playing in thier panties bras and dresses ...My oldest sister caught me 1st and she got me to masturbate fior her thru the panties telling her all the details of how I felt dressing up like a girl I had 4 sisteras all older than me .... after the 1st sister caught me and i was embarresed I allowed the others to catch me too!!!!i have also been Bi all my life so I enjoy both sexes equally .....I hasve met a few guys that enjoy my company dressed as a gurl but i'm older now so i'm not very passable any more plus since this is my 2nd marrige i put on some extra padding lol


also and i get brave aometimes late at night when thje wifey is away I'll go to a drive thru restaurant to flirt with the guys and the girls too I love the feel and the look of pink panties with black lace trim matching bra sheer black thighhigh's,white garters black mini 4 inch heels and a tight sweater to show off my 34dd breast forms

es Cheryl
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Old 01-29-2010, 08:56 AM   #32
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First time

My first time was on a work trip and we went to a GLBT bar. I was infatuated by Michelle. After a couple of drinks she was sitting on my lap and she placed my arms around her. I could feel her cock through her black and silver dress and she could feel mine. I mentioned how I loved her dress, so she offered me an exclusive fashion show back at her place. Quick as a flash we were there , she was parading up and down the hallway Like a model. She sat next to me in a floral dress and we made out. I had a hand in her knee/thigh. I got in the floor and slid up under the floral dress and nibbled my way to a yellow pair of boyleg shorts with tweety bird on them saying " bewtiful". Feedback was my technique needed some improvement but michelle was a caring teacher.

I am still looking to improve......
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Old 01-30-2010, 12:23 PM   #33
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try the cheerleader outfit always gets me hott
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Old 01-30-2010, 03:43 PM   #34
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Holy crap!!!

I haven't logged in since 11-25-2009... and see my post on the front page...

I have to say I'm honored that people enjoyed and as an update am looking for someone to go through with the fantasy. Lost contact with the guy from the story.

I've been looking around lately but most seem like guys that want to get laid and not into the "fantasy". Anyways, surprised to see the thread still here...
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Old 01-30-2010, 05:14 PM   #35
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I did have one more experience with him, we were talking online a few months ago and both very horny. Before I knew it he was asking if we could meet up, I didn't want to drive to go see him due to it being a decent drive and late.

He agreed though to meet at the park near where I lived which I didn't think he would actually want too. Due too it being late and him having to get up early.

I was nervous again as usual and arrived early at our decided spot. It was dark at the park but we both were willing to take chances...

I'll continue on soon...
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Old 01-30-2010, 06:06 PM   #36
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Hello there...just driving by and noticed this thread.

You might enjoy a few of my stories that involve cd, strap-ons and mm action.

If interested click the link below and look for my Marion series and The Bet.
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Old 01-30-2010, 10:33 PM   #37
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Originally Posted by Forfunn84 View Post
I did have one more experience with him, we were talking online a few months ago and both very horny. Before I knew it he was asking if we could meet up, I didn't want to drive to go see him due to it being a decent drive and late.

He agreed though to meet at the park near where I lived which I didn't think he would actually want too. Due too it being late and him having to get up early.

I was nervous again as usual and arrived early at our decided spot. It was dark at the park but we both were willing to take chances...

I'll continue on soon...
please do it sounds good
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Old 02-01-2010, 08:19 PM   #38
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Cd

Hi,
newbie here.
Just wondering if you have ever been with another Cd and experienced a lesbiin type encounter ??

Have always wanted to do that....
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Old 02-03-2010, 12:30 AM   #39
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So I pulled up early cursing myself for getting into a situation I couldn't quite control. I trust the guy but don't like being out of my element at all. And here I was ready to give head at a private park.

All I could do is smoke my cigeratetes while I tried to decide if I should run or stay. Before I knew it he pulled up behind me and I knew it was him since it isn't quite normal for a car to pull behind you in a quite place. I called him
to make sure it was him and he laughed. I hurried over to his car and jumped inside. We exchanged some friendly talk and for whatever reason I decided for once I would make the first move and began rubbing his dick through
his jeans as we talked. It didn't last long for him to ask for a bj. I wasn't feeling comfortable there though and suggested we find a better spot.

Now I have never had car sex before or even messed around in a car with a girl. So I was lost on what even to suggest. He took the lead and we drove around and found a parking lot for some apartments that was barely lit. Once we pulled in and had the car off I went straight for him, although I wasn't dressed up I went into my "whore mode" and had his pants down with his thick dick in my mouth. He loved it and would jack me off while I was sucking him. I foused hard on making him cum and was ready for it to enter my mouth. Then all of a sudden he told me to stop and that he was done. He apologized a 100 times and said it was the medicine that he was taking and couldn't "finish". I felt like a bitch but knew I had been sucking him off good. Either way he missed out since I was more than willing to take his cum on me or in my mouth.
So it didn't work out great but I was glad to see that I was more comfortable sucking him and not afraid of the taboo or anything. I guess there's a downside to messing around with older guys
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Old 02-04-2010, 07:18 AM   #40
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Not all the old guys are like that...
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Old 02-04-2010, 12:47 PM   #41
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Loved Your Story! I Have Beenj Crossdressing For Years But Have Never Had The Chance To Be With Another Man. I Often Fantacize About Being With Another Crossdresser In Our Lingerie And Seeing How Far It Can Go.
There Must Be Some Other Readers With Stories Of Their Own. Share Them.
Maybe Someday I'll Be Able To Share My Own.
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Old 02-04-2010, 02:26 PM   #42
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Wow, that was hot! Got me hard in an instant!
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Old 02-08-2010, 09:31 PM   #43
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I had been dressing for quite awhile - mostly in private and alone - with all the fantasies of course running through my head. I'd had previous experiences with TS in Asia ( long story) so this was not unknown territory for me
At one point I finally get so horny I couldn't stand it and began searching the internet (CL) for any possibilities. I finally found a guy who was into CD's and wanted to dress me and use a dildo on me and see how that went.
I packed a small bag of clothes , met him in a parking lot to make sure it wasn't an axe murderer or too weird. He was basically normally so we went to his apartment a few blocks away. He made drinks and put on some TS porno movies.
He asked to see what I would wear , then pulled out some more clothes and I asked him what he wanted me to wear- we picked through a bunch of items , decided on everything and then I went into the bathroom to change.
Sheer nylons, garter belt, panties, bra, snort tight skirt, top, hi heels and wig.
I was nervous and he kept feeding me drinks.
I came out and he was so surprised that I looked so sexy and hot. I'm fairly petite with a nice fem legs and ass and high asian cheekbones and almond eyes.he had the hots for me it seemed. He had me model for him while he checked out my legs , pulling up my tight skirt to rub my ass and play with the straps on my garter.
We sat down on the bed and watched more TS porn and drank . He asked me if I liked what we were watching and of course I did.
He ask me to lay down on the bed, facing the TV and the got behind me and puled up my skirt, had me wiggle my slim hips so my pantied (thong) rear was totally exposed. Then he puled my panties aside and rubbed my rosebud, working it. Then he added lube and a finger. My hips were rising up to meet his fingers . Then he had a small plug against me and pushed it in- I thought I would explode right there. He gently worked it in and out and then I felt something bigger press against me- A larger dildo. He reached around under my top and began squeezing my nipple as he pushed in harder. I was one of those ' hurt so good' moment as he worked it deeper and deeper into me.. Once he got most of it in he began fucking me with it and it felt so good.
He moved to the side of me as I got on all fours so he could really work my nipples as he saw that really turned me on and I couldn't help but turn to the side and push my face into his crotch. He fumbled with his zipper then released a decent size cock right in front of my face which got me going. could not resist but to bring my lips up close and kiss the head. I let in slide all around my face and kept licking everywhere as he kept using the dildo on me. As he got really hard, I let it slip past my lips and into my mouth , being careful with my teeth.. I used my tongue to whip all around and he started moving his hips.
He pushed the dildo in all the way and I did my best to please his cock. I was pushing my hips back trying to really work the dildo and felt like a little slut.
He must have been really worked up because in about 8 minutes he pulled his cock out and started stroking like crazy as I watched from a few inches away.
Within 2 minutes or so he spurted out , hitting my face and tongue and let the dildo go.
I got a little taste which seemed so sexy and erotic and then he was done.
I was worn out especially physically from being so nervous. I felt like a sexy slut who had just drained a guy. I got redressed in street clothes and felt really weird. Didn't say much , just left and felt strange for several days.
He kept emailing me to get together again and do more. He would send me long emails about what he wanted me to wear and what tings he wanted to do.
It all seemed too possessive and strange so I just never responded back- although I have not lost the urge to do something similar again.

Last edited by amylin456 : 02-06-2013 at 09:32 PM.
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Old 02-10-2010, 07:46 PM   #44
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I have had a few people request a picture- so trying here:

Last edited by amylin456 : 09-21-2010 at 03:06 PM.
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Old 02-10-2010, 07:49 PM   #45
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I have had a few people request a picture- so trying here:
Very very nice! Lovely pic!

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Old 02-10-2010, 07:55 PM   #46
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Thank you- finally figured out ho to do !
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Old 02-11-2010, 02:00 AM   #47
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My first time cross dressing wasn't with a man but with a woman. I lost a bet with an ex girlfriend and to make me pay she crossed dressed me and fucked me with a strap on. That night I had the most incredible orgasms and we continued it as a regular thing. I don't miss much about her but I do miss her fucking me. Most of the time it was in drag.
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Old 02-11-2010, 07:49 PM   #48
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My first time cross dressing wasn't with a man but with a woman. I lost a bet with an ex girlfriend and to make me pay she crossed dressed me and fucked me with a strap on. That night I had the most incredible orgasms and we continued it as a regular thing. I don't miss much about her but I do miss her fucking me. Most of the time it was in drag.
Glad you had such a wonderful experience!
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Old 02-13-2010, 03:58 PM   #49
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.......

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Old 02-13-2010, 06:30 PM   #50
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So my first time CDing was when I was 12. When I was in middle school I use to have a few hours alone in the house every morning. I had recently started to get interested in girls, and the thing that got me hardest was panties. I use to love seeing thongs sticking out of jeans. At first I thought I just liked seeing them, but I soon realized I was jealous. I wanted to be a sexy women with my thong sticking out of my jeans. It was at that point I started playing with my mom's panties.

At first I would just go through her panties. She only had two thongs, and one very sexy red lace panty. Her other panties where bikini style, but they were all silk and satin. I loved the way they felt on my cock. Soon I was wearing her silk panties everychance I got. I would get so hard looking at my panty covered ass. Later I started to wear her bras (which were huge on me as she has d cups). I would stuff her bra with her panties, and wear her short skirst. I started to fantasize about getting caught by parents, and being forced to play with my dad's huge cock.

I remember the first time I ever came was when I found my mom's sexy nighty. It was a short silk green gown with lace around the breast. I felt so hot in it, and the silk felt so good on my dick. I didn't really know what masterbating was then, but I just started rubbing my dick with the silk. I got on my knees, and stroked faster. It felt so good, and I loved seeing my dick wrapped in her night gown. I started to imagine she was there watching me cheering me on to go faster. Finally it was to much, and I blew my first load all over the gown. I did my best to clean it up. I never got caught by my mom, but I think she always knew.
I'm not a CD but after that, I think I'd like to get to know one...
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