My first experience

Every story begins somewhere, so tell us how you got started crossdressing. Only one (1) topic per member, please!

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Davina T
New Member
Posts: 6
Joined: Tue Oct 02, 2018 11:20 am
Location: Birmingham, England

My first experience

Post by Davina T »

Hello to all.
My first experience of the joys of crossdressing was when i was 17. I was dating a friends older sister. We had been invited to a Halloween fancy dress party. I am a rocker and at that time i had very long hair and always wore skin tight jeans and leather jackets. I was stuck in my ways and not interested in a fancy dress party. To be honest i looked silly enough. Lol. My firlfriend thought differently. She said i needed to make an effort. But it was alteady 1845 on a friday night and i was already 5 or 6 beers into the evening.... So no chance to get an outfit. I will spare you the discussion that took place. It ended with me dressed in my girlfriends school uniform. My hair in pigtails. Stockings, suspenders and a g string underneath.
Cut to the club............. I was very popular. Lots of free drinks. I did not feel any different about myself and definitely hadnt considered doing it again. To be honest the g string was uncomfortable.
That all changed when i went to the toilet to have a wee. I was at the urinal as always when an acquaintance walked in and said..............f**k me i thought my luck was in. Which made us both laugh. As i walked past him to leave he helped himself to a feel of arse and again complimented me. It was then i realised i liked being complimented about my appearance.
Up until that night i was lost in averageness. Average hight. Average build. Average penis. Never realy noticed at all. But now i was empowered. And from that moment i used my looks to my advantage. More free drinks and even made it into the dancers cage. With 3 other school girls. It was then i spotted my girlfriend arms around her former boyfriend tongues locked together. So i took a chance with what was by now the 2 remaining school girls in the cage with me.... I will save you the details but i had a great night with them both.
Ever since that night i have taken every opertunity to dress up. Always in secret. That is until i met my current girlfriend. Who is the most amazing person. It was one already messy christmas. When we were talking about fantasies and other naughty things. When she asked to see me dressed. I obliged and have never looked back. I now have a reasonable wardrobe, i have started to experiment with make up and wigs. And i really like my image.
Looking forward much more time in skirts and being admired by my amazing girlfriend.
Writing this is amazingly emotional. Fear excitement and a weight off my shoulders. Love to all. Write again soon.
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DonnaT
Miss Great Goddess
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Joined: Fri Sep 17, 2004 11:04 am
Location: No. Virginia

Re: My first experience

Post by DonnaT »

\:D/
.............
DonnaT
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KimberlyS
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Joined: Tue Feb 24, 2004 4:01 pm
Location: North Central USA, SD

Re: My first experience

Post by KimberlyS »

Awesome story. Look forward to hearing more from you.

kimberlys cd
joe in a skirt
Site Administrator

I am a physically male person that likes to wear feminine clothes at times.
Just trying keep a balance for my self along with keeping my wife and kids in mind.
Davina T
New Member
Posts: 6
Joined: Tue Oct 02, 2018 11:20 am
Location: Birmingham, England

My first experience with others

Post by Davina T »

Hello to all.
Inbetween that infamous fancy dress perty and now. I have only told 3 other people. My current partner(the most amazing person ever) and our 2 best friends(who happen to be a couple).
I would find myself living as a man 90%of the time. 100%in public. Very rarely shaved myself all over and only very rarely would i ware anything feminine. And if i did it would only be panties under my clothes.
Since i have been open with my partner i dress more often and have now got to the stage where body hair is uncomfortable. But it took a night of partying to be more brave. Before that a bit more in depth about me and where i was mentally. I would on occasion put on a pair of panties and more often than not end up masterbating about being fu***d. Not volunteering myself but being forced/coerced into it. And it always left me wondering about my self, my sexuality. To be blunt how much of a freak i am. Next morning life would start again and off i would go........... Until the next time. Now back to the point.
The female half of our very friendly couple was at our house one night. And i got to the point where i realy needed to feel lingerie against my skin. So i put on my favourite underware and covered them with my male clothes. The 3 of us needed more beer. So i walked to the shop. I felt so sexy knowing what i was wearing. And i kept trying to judge peoples reactions to see if my sexy secret was safe......... Or not lol. On my way home my girfriend phoned. And during that call i said i wanted to come out to our friend. I got nothing but encouragement. So when i got home i put on my favourite dress(a shear black maxi dress) and my best heels. And walked down stairs. I dont mind admitting the fear i felt. But that quickly evaporated when i walked into the room. I was welcomed so warmly that all self doubt left me. I also felt realy sexy as the comments i got were more than encouraging. They were down right raunchy. It was at that moment i decided to come clean to our friends boyfriend. So cut to a month or so later. Another night of fun at our house. I took an opertunity to go for a shower and dress accordingly. I came downstairs so full of myself. I struted like a sl**straight towards my male best friend. His jaw hitting the floor was enough to let me know he approved. We spoke at length that night. It was and is still very surprising to me how normal it all was.
The next time we all had the opportunity to get together was again at our house. It all started as normal as the last night had been. I dont know what started it......... But before long the girls went outside for a cigarette and i found myself on my knees in between my friends legs doing what every good sl*t should do. The girls returned into the room. Lets just say that i got used properly and ended with a tasty reward. Which i swallowed with glee.
Up until that night and even now i dont find anything attractive about men. I dont even wander about what they might be concealing in their pants. But i do long to suck on another lovely hard c***. I really want to have the real thing take me from behind. Again i have to say my girlfriend who was very active in pegging me that evening has been nothing but supportive of me and my new found kinks.
Love to all thanks for reading. X


*** Topic merged to proper ongoing topic by SL. ***
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