"You're being quiet tonight..." It was from a woman (I assumed it was a woman) named Bethy_24.
"Yeah, I'm just taking it all in." I don't make a habit out of chatting online, in fact it's rare that I do it at all. While I waited for her, I looked up her profile. Twenty-four years old, student, lives in the City, not married, no kids. That's in stark contrast to me--36, divorced, kids, living in the suburbs.
For the next half hour we had a good time chatting and getting to know each other. I told her how old I was, and it didn't seem to faze her.
"Actually," she wrote, "I'm into older guys...." Not one to ignore a gift-horse, all I could say was, "OH?!"
We chatted for a little while longer then swapped phone numbers so that we could talk on the phone the next evening.
I called her and we talked for two hours, discussing pretty much everything possible. She talked about a woman she works with who seems to have the "hots" for her. I asked her how that made her feel.
"Well, I've been thinking about what it would be like to be with a woman--sexually. I've slept with women, as friends, you know? And I love the feeling, the warmth, the sensuality of a woman. Men don't have the same warmth that a woman has. Know what I mean?" I suppose I did.
"Anyway, she's pretty hot and I think I might do something with her, except she's married and I wouldn't want to have to deal with that--breaking up a marriage. But then again, I suppose he wouldn't have to know."
"I don't know," I responded, "Maybe he'd be into it? I know I'd be." Understatement on my part.
"What--you'd like to be with or watch two women?" she asked, becoming more interested in the direction the conversation was heading.
"Oh yeah, either way. In fact, I think that's a universal guy fantasy-to be with or watch two girls get it on. Guys secretly love the whole idea of lesbians, as long as they're not "butch" lesbians."
"I know what you mean--if I'm going to be with a woman, she's going to be the picture of femininity. What's the point of being with a woman if she looks like a guy?"
Bethy (which I learned was NOT her real name) asked if her talking about being with a woman turned me on. I admitted that it did, and encouraged her to keep entertaining me with her lesbian yearnings. She thought my interest in the topic was mildly amusing. We decided to get together the next evening for drinks downtown and said goodnight.
The next night was very enjoyable. Bethy turned out to be a very sweet, young woman, though I didn't think we had enough in common for a long term relationship. We're two different people, and she is on a completely different energy level; but for the night we were on the same page. She remarked that the one thing she wanted to do someday was to see a drag show at the Nineties. I admitted that it sounded like it could be a good time and suggested that we could go there that evening. (At this point and yet even today, she had no idea I was a crossdresser.) She was excited that we were going to the Nineties, as was I. Like her, I'd never seen a drag show, except those I'd put on for myself alone at home. So we walked to the Gay Nineties where they did in fact have a drag show. (For all I know, they have one EVERY night.) The place was packed--seriously--wall to wall people. I'd guess that a majority of the people were heterosexuals, though I suppose you can't always tell.
We went upstairs and found a place along the wall to watch the show, both in awe of the "performers". She remarked that they were so pretty. I was amazed at the number of women that were getting really worked up by the ladies on stage. If I looked like that, I'd flaunt it too. We stayed until the place closed and walked back to our cars. We'd both had a few beers, which gave me the nerve and courage to remark casually that it would be fun to do that.
"Do what?" she asked, as we continued walking back toward our cars.
"To dress up like a woman--make-up, heels, the whole works." I said it like it was no big deal.
Her face immediately lit up. "Really? Oh I think that would be SOOOO cool! We should do that sometime--I could even help you!"
"Yeah? Well I'd need someone to help me cuz I'd really have no clue what to do or how to go about it." Was I lying? Yes, but she didn't need to know that I already had a closet full of clothes and nice-sized collection of make-up and nail polish. This was a classic case of the lawyer leading the witness and it was working to perfection. She went on. "I have a neighbor who does make-up for John Casablanca, and she'd love to work on you!" She was already working out the logistics. "You should come over so she can get a look at your face and complexion, that way she can come prepared with whatever makeup is needed. Oh--this will be so much fun!!"
She asked me how long I've wanted to do this. I explained that I had always had an interest in lingerie but had never met a woman who shared the same interest and desire. "Oh really? That's too bad. I think more people should experiment--men, especially, that way they experience how the other half lives. Gain a fuller appreciation for women perhaps." I told her I agreed completely.
By this time we had arrived alongside our cars, so we kissed goodnight and made plans to talk the next day.
Driving home, I couldn't help but to reflect on my good fortune. I was honest in one regard, I had never met a woman who thought my crossdressing desires were interesting much less exciting. My ex wife is my ex wife partly because she could not tolerate my "deviant desire" to wear her clothes and lingerie on occasion. (Deviant desire was her description, not mine.) I even went through therapy for a period, at her urging, to see what was really wrong with me. Of course I learned that I was quite normal, healthy even. The therapy did me a world of good. Rather than curing me of my deviant desires, it made me realize that I was a good, well-adjusted man with a soft, emotional, feminine side. I needed to be in a relationship with a positive, supportive and open minded person and my wife could not do that for me. The divorce came not long thereafter.
The next evening I called Bethy, and we started up where we left off. "So you really want to go through with this? I spoke to Karen, my neighbor upstairs, and she'd be thrilled to do your make-up. Now all we need to do is go shopping for some clothes. And you should get a wig too, if you really want to look good." We decided that we'd go to Ground Zero or the Nineties the day after tomorrow, me dressed as a woman.
This would be the hard part. I am on a limited budget and while going shopping with Bethy would be very exciting, I don't want to reinvent the wheel either. I already have the clothes and I have a wig. But how do I explain the fact that I have the stuff without letting on that I have done this before? I remarked that while it would be fun to go out shopping for clothes and such, but I had plans tomorrow and would be unavailable to "go shopping" with her. Instead I could take a long lunch break tomorrow and check out a couple used clothing stores nearby. She thought that would be a good idea, and encouraged me to try and find a wig and some shoes that fit. We decided to touch base the night of our excursion to work out the remaining details.
The next night I went through my clothes and found a couple silky, long-sleeved blouses, a pair of stretchy pants and a skirt, some nylons and panties, and a couple pairs of heels. I also pulled out my wig and through it in a plastic bag. I was ready. I thought about painting my fingernails and toenails, but I didn't want to appear TOO into it. I also selected a long ladies dress jacket to keep me warm, considering it was supposed to be below zero tomorrow night.
I called Bethy the afternoon of our "date" and got directions to her apartment. I gathered up all my items, working through the explanations as to where I bought the stuff.
She greeted me enthusiastically at her door, giving me a hug while smiling broadly. She was enjoying this as much or more than I was! She eagerly asked me to show her what I had "bought." She wasn't really impressed with the clothing, but I admitted that I had no fashion sense and felt safe picking out only things in black. She was impressed with the wig, remarking that it was very cute and would match my face well. She again asked if I wanted to do this, and when I nervously nodded my head "yes", she picked up the phone and called her neighbor Karen.
Karen came down with her make-up bag, and I was surprised that she had brought another friend with her. So here I was in Bethy's apartment with three women, all smiling in anticipation. Karen and her friend were both 19 years old, and both were very cute with petite bodies that looked good in the skin-tight clothes they were wearing. Karen sat me down on a tall chair, and the process began. I realized at this point how wonderfully exciting the situation was. Three women, make-up, women's clothes and a night out as Bethy's girlfriend.
As Karen applied the foundation to my face, I asked her if she'd ever done make-up on a guy before. I guessed given her age that it was a safe bet I was her first and she agreed. She was so close to my face, inches away from me...I could feel her breath on my skin. She smelled very nice and her low cut, revealing top was visually appealing. I could see her breasts being uplisfted by her Victoria Secret. After the foundation, she worked on my eyes, then my cheeks, then my lips, and finally my eye brows and eye lashes. I was in heaven, I really was.
Bethy and Karen's friend would offer suggestions from time to time and both remarked that I was looking quite nice. If I hadn't been so turned on, I probably would have been quite embarrassed.
After an hour in the chair, Karen put down the make-up and proclaimed she was done. Bethy came over and squealed in delight, exclaiming that I looked Sooo very feminine. I was then directed to put on the wig so that Karen could style it and make sure it fit right. Anticipating the response and further leading the witnesses, I said, "I suppose you'll want me to model the clothes, too." I said this like it was something I didn't want to do. (Yeah, right.) Model women's clothing for three women. I repeat, Heaven. As if it were a predetermined certainty, they responded, "Yes, of course, you'll have to model the clothes so that we can get the full effect." It was almost too much fun in one night, and the night had just begun.
I put the wig on and Karen fussed with it for a few minutes, then pointed me toward the bathroom to change into my clothes. They had already gone through the clothes and decided what I should wear. It took me almost ten minutes to carefully dress without dislodging my hair or smudging the make-up. They weren't satisfied with the look so Bethy pulled out a skirt and top of her own which fit me quite nice. The three woman looked me over and were thrilled with the results Karen kissed me on the cheek and wished us luck, telling us girls to have a good time. Karen and her friend left, leaving Bethy to quickly ready herself for our night out.
We drove to the club and reviewed some ground rules, such as what to do if one of us gets "hit on". I explained that odds are I would NOT get hit on, but we'd have to play that by ear. This naturally led to Bethy's next question, whether or not I'd consider being with a guy. I said that going out dressed as a woman was enough for me to handle without adding that consideration, though I did say that I was somewhat curious what it would be like to be with a man. She said she knew a couple guys who also were also curious if I ever wanted to go that way. I said I'd keep it in mind, again, not wanting to appear too excited by the prospect.
We arrived at Ground Zero around 10:30 and stayed there until midnight. We had a couple beers, watched a B&D demonstration, danced for a while, which was extremely difficult while wearing 4-inch heels. I was not at all nervous with the situation, considering I had been there a few times before while dressed up. Bethy took great care to make sure I was OK, to hold my hand and to guide me around like her submissive girlfriend. We decided to drive over to the Nineties for the last hour of the night. In the car I remarked how my feet were killing me. Bethy responded that now I know how it feels to wear heels. She again commented on how nice I looked and how much fun she was having.
At the Nineties we watched more drag performances and we got a table up close and personal so it was pretty cool . The ladies all looked good. We went back downstairs to dance away the remaining minutes of the evening. On the way back to the car, I thanked her for showing me the night of my life, which it really was. I'd never gone out with a woman (or anyone for that matter) while dressed up, so this was a first. She again asked me if I had thought about going out with a guy, and I said I wouldn't completely dismiss the idea and would give it some thought. I dropped her off at her place and she gave me a hug and a kiss and gave me the nicest compliment--she told me that I was a wonderful woman and couldn't wait to do it again.
On the way home, I ran through the events of the evening and was amazed at my good fortune to meet someone like Bethy, who was so open-minded and willing to take me under her wing, so to speak. I think the biggest thrill was being made up by Karen while Bethy and her friend looked on, as if I were on display or something. I was and I was loving it. Nothing out of the ordinary occurred at either Ground Zero or the Nineties, not that I expected anything out of the ordinary. The other times I had gone to Ground Zero dressed up I was disappointed that I didn't even get a look or second glace. Even dressed as a woman, I probably looked too normal since I was not wearing any rubber or leather.
While I don't think I fooled anyone and I certainly don't consider myself as "passable," I was reassured to know that either club is a great place for crossdressers to go without any fear of ridicule or harassment.
If I go out again, (and I probably will since Karen says she wants to do my make up again and this time take photos and Bethy wants to act out a lesbian fantasy with me) I will write another article.