After more than 20 years of reading letters in your magazine about men who dress as women, I had to try it, though I had no idea what it could lead to. I started by just trying on my wife’s panties. I loved it, and I couldn’t stop. I soon added more—crotchless pantyhose, nylons, lingerie, bras; then fake boobs, wigs, heels, lipstick, makeup, everything. As I have little facial or body hair, I looked very passable as a woman.
Soon just dressing up for myself wasn’t enough; I needed to find someone to do it with. The thought of being a woman in the company of a man turned me on. Years earlier I had engaged in sexual things with guys. I didn’t dress as a woman at the time, but I let several guys suck my cock. They wanted to fuck me in the ass as well, and I found that I loved it. But after I got married I stopped, and didn’t do it for years. Then, when I started dressing up, I had a strong urge to do it again.
I took out an ad in a sex magazine saying, “Hot passionate crossdresser looking for hot sex,” and got three or four replies. The first couple of guys I met weren’t my type, but then I met a guy who was. I met him in a park, dressed as a woman. The first thing he did was to pull up my dress, pull down my panties and start sucking my cock. Then he bent me over a picnic table and fucked me. As soon as he filled my ass with come he was gone, leaving me wanting more.
The next day I got an e-mail from a guy who said he had seen me getting fucked, and he could give me more than that. He also said we knew each other, but he didn’t give me his name. I wrote back and we exchanged several letters and photos, although his pictures just showed his body, not his face. Then finally we set up a meeting.
We met in the park, but in a more secluded place this time. I was shocked when I found out the guy was an old coworker of mine named Harry. The first thing he said was, “Show me your panties.” I pulled up my dress and spread my legs. He put his hand between my legs, then brought his lips to mine and slid his tongue in my mouth. I had never kissed another man like that, and it was great. I had also never sucked a guy’s cock, but now I went to my knees, undid his pants, pulled out his hard eight-inch cock and took it in my mouth.
After I sucked him for a while he asked me if he could come in my mouth. I stopped sucking him and said, “If you’ll fuck me afterwards.” He nodded. I took him back in my mouth, and a minute later he blasted what felt like a quart of come down my throat.
He was still hard when he finished. I got to my feet and bent over the hood of his car, and he slid his cock into my ass. He hammered away at me for 20 minutes before he came inside me.
I was still leaning over the hood of the car with come running out of my ass when I felt a cock poking at me again. This one felt bigger than Harry’s, and when I looked back I saw that it was another guy. I didn’t know who he was or where he came from, but I didn’t care. He fucked me for half an hour, and I was loving it and begging for more when he finally filled my asshole.
The second guy’s name was Josh, and it turned out that Harry had arranged for him to be there. He said he had known I was the type who could take two guys at once. Well, he was right.
Harry was now ready for more. I got on my hands and knees and he took my ass again, while Josh stood in front of me and offered his big cock to my mouth. We spent most of the night that way, one of them in my mouth and one in my ass, except when they took turns sucking my cock.
I now do Harry and Josh on a regular basis, both together and separately. But that’s not all. Recently, as I was waiting for them in a bar, I met a guy named Ric, a good-looking black guy with a fat nine-inch cock. I was dressed up, of course, and when I showed him my panties he took me into the men’s bathroom. He pulled out his big cock and I took it in my mouth, begging him to fuck me. After he came in my mouth he proceeded to pound my hot ass. Then Harry and Josh showed up, and I sucked them both while Ric fucked my ass.
One night not long after that I went to a gay swingers’ club and made it with nearly every guy in the place. I sucked them all and fucked them all, some more than once. I did at least 20 cocks, and I still couldn’t get enough.
Since that time I must have had over 100 cocks. What can I tell you—I love dick! I love pussy too, but I have to say that I love cock more—especially when I’m dressed up.
—Name and address withheld