After 15 years with my lovely fiancee, Larissa, we mutually decided it wasn't going to work out. We called off the engagement and she moved out of the house we had shared for over a decade.
I told myself that if I ever found myself single again, I would indulge my gay desires, just to see if it would bring me any sort of peace. I wasn't very hopeful. I had resigned myself to being a gay fetishist. That is, only interested in sex with a man until I had an orgasm, at which point I would quickly stop and return to being a "regular" guy. Some would call this "post-nut clarity."
I spent 2 months practicing with makeup, following every tutorial I could find, sometimes putting on a full face of makeup only to wash it off and start over. Each time, it looked slightly better than the time before. By the end of the second month, I had, in my own opinion, become proficient at feminizing my face with makeup, and was able to do so in under 30 minutes. My confidence was very high, and with that, I started going to the local gay clubs, always in my feminine persona, and always dressed as well as I could manage.
One Saturday night, I was at a club about 45 minutes from my house, sitting at the bar by myself. I was chatting with the bartender, whose company I had come to enjoy, and basically enjoying the evening, when a handsome man in his mid 40's walked in took the seat next to me.
He introduced himself as Gary and asked if he could buy me a drink. I was suspicious, but flattered that he would ask, so I agreed.
One drink turned into several, and we were really hitting it off. He owned a local contracting business, and told me he had always been very attracted to sissies. I didn't exactly embrace the term "sissy" at that point, as it struck me as a term used to describe weak men, and I am far from weak, even in a full face of makeup and 4-inch stilettos. I let the sissy remark slide, mostly because I was enjoying the conversation.
The next time I looked at the clock, it was nearly midnight, and I didn't think I'd be able to sober up enough to drive home before the bar closed for the night. I told Gary I needed to find a hotel room for the night and call for a ride.
I don't know why, but when Gary offered to let me crash at his house, I wasn't immediately creeped out. I still politely declined, and continued looking for a room for the night. Gary assured me that he would be a perfect gentleman, and I could sleep in his guest room. Maybe it was the booze thinking for me, but he sounded perfectly reasonable, and I wasn't looking forward to checking into a hotel at this hour, so I accepted his offer. My only conditions were that his guest room had a lock on the door (it did) and there would be no funny business. It wasn't that I didn't want to experiment with a man sexually, and it certainly wasn't that Gary wasn't attractive. My main point of contention was that I had been drinking, and couldn't trust my own judgement in this condition.
Of course, Gary agreed to my conditions, so I paid my bar tab and we walked out together. when we got to Gary's car, he opened the door for me and made sure I got into the passenger seat without a problem, then closed the door and walked around to the driver side. I remember thinking that it was very classy of him to do so, but stopped myself in that moment, remembering the booze.
Gary lived 10 minutes from the bar, and when he parked the car in the garage, he got out, walked around, and opened my door for me. I could get used to this sort of treatment. Wait, no, that's the booze talking, dammit.
Once inside the house, Gary showed me to the living room and invited me to sit and talk for a bit. I was tired, but the prospect of talking seemed nice, so I took a seat on one end of the couch. Gary sat close to me, but not too close. I remember thinking what a cool customer this guy was. If only I had been that smooth when I was dating women, I probably wouldn't be sitting on a stranger's couch, wearing a wig and a dress. Alas, I was sitting on Gary's couch, in full femme presentation, and I felt comfortable.
Gary handed me a drink, and I sipped it, knowing I wouldn't have to drive home.
We talked for another couple hours, on many subjects, but we ended up talking about sissies, and how I didn't care for the term. Gary explained to me that being a sissy isn't about being weak, but about embracing your feminine side in all aspects, enjoying the feminine experience, and surrendering to it. It didn't sound half bad when he described it, and I found myself saying so.
Gary asked if I had ever considered such a thing, and I have to admit that I did, and found the concept very alluring. He said he could teach me how to be a proper sissy, and I told him I'd sleep on it.
At that, Gary showed me to his guest room. It was a master bedroom, with its own bathroom, so I locked the door, washed off my makeup, took of my wig and heels, slipped out of my dress, and collapsed on the bed, exhausted.
I woke up around 10am, confused at first by the unfamiliar surroundings. My mind reeled as I struggled to remember what I had done the night before. After a few minutes, when the cobwebs had cleared, I remembered the entire evening in detail, including Gary's offer to teach me how to be a sissy. "Wow," I thought to myself. I've had guys try to pick me up before, but I had never agreed to go home with a man before, and I'm certain that if I had, they would have tried to force themselves on me. Not this guy. Not Gary. He was as good as his word -- a perfect gentleman from start to finish. At least he was last night.
I decided not to shower or reapply my makeup. I was planning to get a ride back to the bar, get in my car, and drive home.
When I walked out of the bedroom, I had my wig on and I was carrying my heels. Gary was at the dining room table with a cup of coffee. He offered me a cup and I accepted. I kept wondering when the fairy tale would end. Surely when he sees me without makeup, the good guy act will end and he'll rush me out the door. But that didn't happen.
Instead, Gary asked me how I slept, how I was feeling, and if I remembered what we had talked about last night. "The sissy thing?" I asked, to which he nodded. I retreated into my hetero male shell and told him it was a very generous offer, but I'm not ready for anything like that. Gary didn't flinch. He told me he respected my decision, and offered to drive me back to the bar.
Once I got home, I grabbed one of my favorite toys and did what one does with toys of that sort. When I finished, I quickly shed all my feminine effects and went about the day in guy mode.
To be continued...
