First Time Fun

  1. secretservicer
    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. Itsmejj
    Wow this has me so intrested to see what Bethie looks like. I have a mental picture but i want the real thing lol. I love the feeling when i slide panties on or a thong and than my wifes short sexy shorts and a bra and walk around. Unfortunately i am not passable but from sounds of it you were very very sexy. I know you said you got rid of all the clothes and wigs but do you still have urges to wear panties or anything else?
  3. BiKleinGuy
    Interesting story! And the urges may get suppressed but never fully go away. Glad you enjoyed yourself in this way when you were younger. A reminder for everyone to live life to the fullest, jump in, take risks, and we can all have fond memories like yours! This is a similar story to mine. I was sad to see Craigslist personal ads stop taking sexual meetup ads. It allowed me the most discretion and anonymity, not to mention the amazing time I had dressed in lingerie for several men, while it lasted anyway… I’m trying again here, but so far limited luck, I may take that risk and download an app like Grindr or Tinder… thanks again for the story!!!
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