Sex Histories	Sex Histories Archive

Pennsylvania-- You asked about my experiences having sex with men while I was drag.

Sex with the guys who "date" a drag queen is psychologically based. The pleasures both partners feel are more in the head than in the crotch.

Sex with women and regular gay sex with men does not compare to the sex I have had as a "girl." This is not to say that I enjoy it more in drag, but it is very different.

I have had a variety of experiences in drag-- typical man/woman dating and sexual relationships and dominance/submission scenes with me as the dominant (naturally).

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All of the men treated me like I was a woman, even when I was dominant. I don't know to what extent they were conscious of my cock before we got into bed (however, all knew that I was in drag and not a real woman).

I asked each of them what they were looking for: a man in a dress or a woman with a cock. All replied that they wanted a woman with a cock. You could assume something about their true sexuality from this response. Some of then told me they were gay, but preferred drag queens. Others said they were bi. And others implied that they were straight, but did it with drag queens for variety.

Regardless of whether they were gay, straight, or bi, they all treated me like a real woman. They would never make the sexual comments appropriate to man-to-man sex, like how nice my cock is, how they preferred cut cocks, etc. Instead they would talk about my soft skin, my tasty nipples, or my tight hole. I don't have especially soft skin, and I don't take hormones, so my nipples are regular. But they described those features in terms appropriate for a woman.

I met all the men I'm writing about through ads in a variety of publications, including the Philadelphia Gay News.

Don was a traveling salesman for a big consumer-based company in New England. He would come to Philadelphia once a month on his rounds. Ten years earlier he had wandered into a bar in Virginia where he encountered his first drag queen. They bad a brief encounter, and that planted a seed. For years after that he would go to drag bars in NYC and just watch the girls.

By chance he saw my ad and wrote me a letter telling me how he would like to get together when he was next in the area. We met the next month. By pre-arrangement I drove to his motel in the suburbs. I was dressed as a man for the trip because I didn't want to run into trouble in a strange area while in drag.

Don had seen a picture of me in drag, but he had no idea what I looked like as a man. When I got in the room, he was polite but hardly out of control. I could tell that he was uncomfortable with the way I dressed. I was clearly a potential sex partner and I was also clearly a man. But things changed markedly after I got my clothes changed and my face painted. I forget what I wore but it did include stockings (not pantyhose) and very high heels. I have found that men respond favorably to that combination.

With me dressed as a woman his distance vanished. He was on me like a wolf, or like a john on a whore. Before, the idea of having sex was only possible. Now it was inevitable.

He didn't undress me, except what was necessary to get my ass and cock exposed. I can't remember if he fondled my cock that first time, but I do remember that he wouldn't suck it. I asked him to, but he replied that he wasn't into that sort of thing. Later in our relationship he did learn and become quite good at cocksucking. This makes me believe that he is bi.

We saw each other once a month for about a year. During that time I would have to slip out of "character" once in awhile to make a point about the importance of safe sex.

Once, I recall he didn't want to mess with a condom so I said that he could not cum in my ass. During our lovemaking he had gotten me on my back with my legs in a suspicious position and fucked me. "Rape" is too strong a word to use. In my feminine role I tried to ask him to withdraw but he was in the throes of passion and was not listening.

After asking several times (as a woman), I dropped my voice to its normal register, which is relatively deep, and said, "If you keep fucking me, it will be the last time you ever get to use your cock. Pull it out or I'll cut it off!"

Well, he didn't have to pull out because his hard-on just melted inside me.

On those occasions when he did use a rubber, he fucked great. He was also good at foreplay (something women say men don't do enough of). He would start by telling me how luscious I looked. Then he would run his hand along my leg, higher and higher, until he was at my panties. There he would play with my cock inside my panties until it was hard (which it would become in a very short time). After that he would take it out of my panties and either play with it some more or blow me almost to the point of cumming.

I would undress him slowly and we would start fucking. He often had difficulty getting inside my ass (I am tight). Because asses are different from cunts, which was what he was used to, this was the most difficult part of the coupling. But after we got past that hurdle it was smooth.

Another way he treated me like a real woman was that he would climax long before I would, sometimes leaving me frustrated. Sometimes he would even roll over and go to sleep.

We stopped seeing each other. But recently he has reestablished contact with me as a man, a first in our relationship-- I thought the facet of my personality he was solely interested in was me as a woman.

Changing roles some more

The more I did drag in a variety of circumstances, the more I began to wonder how far I could extend this "personality." One area was in the dominance/submission realm. Once with Don, I greeted him at the door of my bedroom wearing a black negligee, black-seamed stockings, and black patent-leather high heels. Around my neck was a studded leather collar and attached to it was a leash, the other end of which I handed to Don as he entered the room. His eyes bugged out of his head and his tongue hung out as he led me to the bed to "work his will with me." He called me a "bitch," said I was his "woman," and ordered me to suck his cock.

This scene was amusing for a few minutes but I soon grew tired of being told what to do. Perhaps there is a deep meaning here. Maybe I am a feminist/women's libber in drag. Others may say that I have enjoyed the male privilege so long that I was reluctant to give it up.

In any event, I decided that I wasn't anybody's woman. But maybe other men could belong to me and serve me just as Don wanted me to serve him. Thus was born my short (but hot) career as a dominant transvestite.

I ran an ad in a little magazine called Bondage and Discipline Digest. I got the ad for free because I entertained the publisher on a couple of occasions. Shortly after the ad appeared I began to get responses.

Here is the text of the ad:

I am the superior, demanding, dominant she-male you have been dreaming about. You know that you want me, but first you have to prove yourself suitable for my purposes and perhaps worthy of femininization. Only then shall you become my house boy or my lady's maid. You must be utterly devoted to furthering my she-male stature. But I warn you: do not trifle with me or waste my time. You dare not respond to my summons if you are not sincere, submissive, and selfless.

Many of the responses didn't lead anywhere. The men were either looking for pen pals (something the publisher warned me about) or were into heavier domination than I was, even whipping and other forms of punishment they wanted me to administer to them.

A couple of men were okay. One of them came by the house several times. I made him call me "ma'am." He would worship my feet, legs, and cock when I would let him.

Naturally, because of my reference in the ad to being a "male," he, like the others, knew that I am a man. But he never made any reference to my male characteristics. My cock was referred to by him "between my legs," and in "Ma'am, may I worship you between your legs?"

I never figured out if this guy was more turned on by being ordered around by a "female," or by the fact that as a man in drag I should have been a sissy but wasn't, and so therefore I was more masculine than he was.

But with one guy, solving the puzzle was easy. This guy called me when I was home from work and asked if he could come over. I had just shaved my body, so getting ready would not be that much of a chore, so I agreed.

He was a big man, 6' 3", about 220 pounds, with a 44-inch chest. We talked a bit, then went into my bedroom. He had a bag with him and at my instruction he showed me its contents-- lingerie, handcuffs, and a wig. I ordered him to put on his things and loaned him stockings and heels to complete his costume (which was what it was, a costume-- he looked terrible in drag).

After he was dressed, I made him crawl around the room on his hands and knees while carrying me on his back. He stopped in front of a full length mirror and I wrapped my legs around his neck and played with myself.

After I tired of this and several other activities, I felt it was time for him to leave. I ordered him to stand up next to the bed. I then handcuffed one of his hands to the bedpost and ordered him to beat off and shoot his load into a towel.

He asked me if he could come in a way so that he could taste his own cum, so I held my hand out in front of his cock, which by now was very hard, snapped my fingers, and said, "Come in my hand."

As he stroked his cock, I stood close to him with my lips puckered as if to let him kiss me, but as he leaned forward to kiss I would pull back. This frustration, heightened by the restriction imposed by the handcuffs, made him come very quickly, right into my palm as I had instructed.

He expected me to lift my hand to his mouth so he could lick up his juice but instead I wiped his cum all over his face, everywhere but his mouth. His tongue eagerly followed my hand, but to no avail; I wouldn't let him taste a drop.

Finally, I let him kiss me. By now he was so hungry for something wet in his mouth that he almost sucked my tongue right out of my head.

As we kissed, I pulled back long enough to say, "You're quite a sight, standing there handcuffed to my bed in your negligee, high heels, nylon stockings, wig and lipstick-- kissing a man."

Author Profile:  Boyd McDonald

Born in 1925 in South Dakota, Boyd McDonald entered Harvard as a high-school dropout after serving in the army in World War II. Jobs with Time, IBM, and several Wall Street firms preceded Boyd's career as a chronicler of gay sex. He was the founder and editor of Straight to Hell (alternatively the Manhattan Review of Cocksucking), and later published a number of anthologies of true sex histories. Boyd died in September 1993, two months after completing his final book, Scum.