The First Time

  1. secretservicer
    Well, let's talk about it

    I was in my early 40's when I got interested in Cross-dressing. I've always been very young looking and, being only 5'8" with a slim build, I thought I'd try being "pretty". I spent a good amount of money on a high-end, flowing red wig since I really wanted to do it right. I tried that on first thing before I went any farther with my curiosity. Being married and not wishing to be 'found out', I had to wait for my wife at the time be at work before I could begin. The wig was very well made and when I put it on, I couldn't wait to do my make up. I used my wife's cosmetics and added my eye-liner, light blue eye-shadow, red lip-stick, a bit of powder, and subtle puff of rouge on my cheeks.The transformation was amazing! I always knew I would make a pretty 'girl' since I had passed for one (in 8th grade), at a Halloween party that fooled everyone there, even my GF at the time. No one knew who I was until I sprung my identity by kissing my GF to the gasps of everyone at the party. Anyway, the result of the wig and make-up cemented my inclination to pursue the life-style.

    I proceeded to scout out the ladies section at department stores. First things first, sexy panties, white lace-top stockings with garters, and a modestly padded bra would begin my outfit. After trying all of that on with my wig and make up, I felt soooo sexy and feminine it made me exhilarated and giddy. I was ready for a pair of high-heels and cute little party dress - the second-hand store was full of them. I found a pink/white pattern dress with lace hems and lace mid-cut collar - kind of reminded me of "Pettycoat Junction". The only pumps that fit me were black but they would suffice for the time being. While I was there, I noticed a pair of long white gloves, surely from a "Victory's Secret" store - these would hide my 'manly' hands. lastly, I bought a medium sized bag to store my secrets in. My outfit was complete.

    Standing in front of the mirror, all dressed up, complete with wig and make-up, I was staring at who I decide to call "Bethie". I swear I could've walked into any bar and never be suspected of being a 'man'. I really couldn't believe what I was looking at - I was beautiful lol.
    At the time, Craig's List was a thing and personal ads were tolerated so I posted my picture as "Bethie" searching for bi-men who were interested in having sex with cross-dressers. I'm flattered to say, I was very popular. I responded to at least 6 inquiries. Two of which were one-night stands and the other 4 became regular hook-ups for the next couple of years. One of my 'men' would lay out rose petals and make love to me as if I were his mistress on a weekly basis. He would buy me cute dresses, sexy panties, and different color stockings to change things up a bit. we still correspond to this day though he is hundreds of mile away. I think he truly loved me.

    Sadly, I got paranoid that my wife was getting suspicious so I packed all my outfits into that black bag and discarded them deep into the woods. I've not returned to the life-style and now, 20 years later, being older and not as easy to pass as vivacious red-head, it's all a very fond memory. I'm glad I was Bethie even for a moment in time.
  2. Tight1-4u
    I was living in Arizona at the time.. about 18yo.. had long hair about to the middle of my back.. thin and long legs.. got mistaken for a female now and then.. had fantasies about what females felt and experienced during sex.. I had tried on panties and stockings but never really much more.. fantasies became stronger and stronger and morfed into what it would be like being a female in a very deep through skimpy sun dress having car trouble on the side of a busy road.. I ask a gal I knew if she would help me.. she got all excited and invited one of her lesbian friends to come and help.. first we got panties.. I wore them for a few days to get used to them.. then we got stockings and a garter and a bra.. they started teaching me about makeup.. the one gal was my size so she gave me a dress it was longer and not revealing at all but we could modify it as I became more comfortable.. any way it kept getting shorter and shorter.. it became more revealing to show a little bra and my two mounds held within.. then the big day arrived we went and got me a sun dress,, pale yellow and very sheer and see through.. short very short, my ass hung out the bottom.. god it was amazing the transformation that took place with that dress.. I was a female.. not just a female a smoking hot female!! Need les to say when I went through with my fantasy of being on the side of the road I got a lot of help.. mostly guys helping themselves putting their hands all over me.. I got bent over and fucked there in broad daylight bent over the fender of my car and in the passenger seat almost every time.. it was almost like a shark feeding frenzy!!! That was part of the road to me transitioning for 8.5 years..
  3. secretservicer
    That's so fun I hope more XDs chime in. It's just so interesting to hear how others got the idea to try it. I'm sure it disgusts "Manly Men" but a lot men do not understand or choose to ignore their feminine side. I was lucky to have an older sister who put on my make-up for that Halloween party. I was able to learn how to do it and try it myself so many years later. I also had a very loving family so I grew up knowing how important it was to be empathetic and tolerant of others.
  4. Tight1-4u
    I found that being tall at 5’11” and very long legged, sexy curvy body and when on hormones having full c cup breasts that it was way easier to dress very provocative and enjoy showing off my assets.. I never wore a bra.. my nipples were and still are very sensitive and erect all the time.. I have narrow hips so I am slender.. my ass has always been very feminine and tight.. so the transition was easy for me!! It was just finally making the move to getting on hormones and my body changing, mostly my breasts growing and my voice changing.. I always kept my body smooth and baby soft.. when I got that first very sheer basically see through very very short sun dress.. that I knew that the girl in me had come home.. now I had been having sex with men but as another man,, even though I kinda was quite sissy looking I was still a man.. when I went out that first time as a female,, and pretended to have car trouble,, I pulled over to the shoulder of the road and got out lifted the hood of my car,, pulled the coil wire off enough that it wouldn’t start,, then went around to the drivers side leaned in over the motor hiked my dress up so about 3/4 of my ass hung out.. wearing a pair of silky string panties.. it literally was the second guy that stopped.. the first one looked me over real good and slapped my ass but then left.. the second guy though he leaned in next to me and kinda pinned me under the hood then started feeling me up while trying to explain what was wrong with my car.. we moved to the passenger side so he could explain better.. when he had me over the fender I felt him slide my dress up and his fingers finding my ass crack.. then a finger finding my pussy.. soon two then three fingers.. then he slid the string of my panties aside and his cock replaced his fingers.. he humps me there for what seemed like an hour but really just 25 min.. till he empties his balls deep inside of me.. he pulls out and tells me that my car needed to be towed and he would call some one., this made me realize that I am a girl,, I am sexy,, I really love getting used by men that way,, so it all began!!!
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