My First Female-to-Male Transsexual Lover

This experience took place in 1988 and was published in Hustler Magazine in 1989.

After 12 surgical operations, spending $50,000, weekly counseling sessions, lots of hormone shots and a new wardrobe, a beautiful woman named Linda Helen Nichols became a handsome man named Les Nichols. Les’s new surgically constructed penis was only two months old when we met, and he chose me to be the first to try it out. He would be my first female-to-male transsexual lover.

For Les and I it was love—and lust—at first sight. We caught each other’s eyes at my friend Johnny A.’s F2M social. (F2M stands for “female to male” among transsexuals and crossdressers.) For the past year Johnny A. has been networking F2Ms through his newsletter, Rites of Passage. Occasionally he has a get-together exclusively for F2Ms and the women who love them. I had known Johnny when he was a full-time F2M crossdresser. Johnny now lives as any other man, but without a penis.

The party was the best I’d been to in years. There were 14 F2Ms and a dozen women-women. Most all of the transsexuals looked totally like men—they take hormones that make them grow facial hair and give them very deep voices. We sat in a large circle, and people talked about their lives, their lovers and their doctors. A few showed us their operations, and we ate pizza. The roomful of men with pussies gave this bisexual sex-adventuress quite a thrill. Many of the “new men” were very attractive, and I flirted with several. Mostly I flirted with Les.

Les was kind of a cross between a biker and a circus performer. His background was French and Greek, which, according to him, makes him a Freek. Born 35 years ago, he is a triple Gemini, which means that he is someone with many personalities. He has a fabulously sexy smile and the most beautiful, seductive, fun-loving eyes I think I’ve ever seen. Before long we were necking on the couch. His kisses were delicious, marshmallow-soft, sensitive and feminine. He possessed that incredible subtle power of seduction that women have (men are much less subtle—more outwardly aggressive), plus an irresistible boyish charm. Before long he popped the question: Would I like to be the first woman to try out his brand-new penis? I considered it for about a tenth of a second. How could I possibly resist? Unfortunately, the penis still needed a bit more healing around the head: so we made our date for two weeks later.

According to Johnny A., who has been researching F2Ms, there are thousands of them. We don’t hear much about them, as they prefer to live undetected, and they blend easily into society. Most feel they are men born into the wrong bodies. They don’t want to be known as transsexuals, but as men.

At present it is possible for doctors to make a penis. The plastic-surgery operation, called phalloplasty, is still in the experimental stages; it’s painful, there are often complications, and it is very expensive. Most F2Ms don’t get the phalloplasty. Only a few are done each year.

There are three types of phalloplasty. One is genitoplasty, in which doctors change the vagina, freeing the clitoris so it protrudes as a very tiny penis that can be urinated through. The genitoplasty clitoris/penis is very sensitive. Then there is microsurgery, which is the most expensive. Skin, fat, veins and nerves are taken from the forearm and are attached with microsurgery. The resultant cock is sensitive and natural-looking.

Linda (Les) chose the abdominal tube method—a simple operation—for his phalloplasty. A piece of the abdomen is rolled into a hollow tube and covered with skin grafts from the buttocks; the base of the neo-penis is then attached at the upper line of the pubic hair, and the tip is attached just below the navel, like a suitcase handle. A second operation, a “tube released,” follows after that heals for eight weeks. The top of the “handle” is cut loose, and a penis head is fashioned from another graft.

With some of these operations, a transsexual risks losing the new penis as well as all sexual sensation. Linda always loved sex and valued her sensitivity highly. Les told the doctor, Dr. Biber (Trinidad, Colorado), that if she lost any sensitivity at all, she would kill him. Dr. Biber heeded the warning and decided to leave Linda’s vagina intact. (Most transsexuals opt to have their vaginas closed up to form a scrotum.) So now Linda is actually a surgically made hermaphrodite. She had already had her breasts removed, a hysterectomy, liposuction on her hips and buttocks to make her shape more manly, and had two round saline sack implants put into her mons to make testicles. Now, no one would ever know that Les wasn’t born a man, unless he told them. If he didn’t tell a girl there was a pussy under his balls, she wouldn’t think to look.

During the two weeks that we impatiently waited for Les’s penis to heal completely, we carried on our romance by phone and by mail. (Les lives in Boston, and I live in Manhattan.) I asked him a million questions about his life and his sex change. He sent me photos of Linda. She had been a very beautiful, sexy, “femmy” lesbian woman with long brown hair, a pretty face, a curvaceous body with large breasts, and she wore Frederick’s of Hollywood-style clothes. She joined the army at 29 and became butch, cut her hair to a crew cut, started wearing men’s clothes and acted more masculine.

Eventually Linda decided to start taking hormones and make the complete change. Why? Lots of reasons. Perhaps the seed was planted as a little girl when she found herself attracted to other little girls. She thought she would need to be a boy to love and marry a girl. She had been abused a lot and felt she might be safer if she were a guy. She saw men getting more respect than women. She wanted the male privilege. She was attracted to heterosexual women more than lesbians and felt that a penis could better satisfy her lovers. She was always highly sexual, looking for sex with lots of partners—a behavior more acceptable for men. Linda imagined that being a man would solve a lot of emotional problems and improve her life in general.

Mostly our long-distance phone conversations were about sex and what we were going to do with each other once we got together. I’m very sexually adventurous and always anxious to try something new. I was very aroused by the thought of making love with Les/Linda and could barely wait. He/she was my bisexual dream-come-true.

He drove down from Boston and finally arrived at my door. We planned to spend three days and nights together. After just five minutes, we were kissing, hugging, humping, rubbing and getting undressed. Why wait? (I would have wanted to fuck Les even if he wasn’t a great kisser—or even if I didn’t like him that much—just for the novelty of it. To be attracted to him was a nice bonus.) I couldn’t decide if I was kissing a man or a woman or both at the same time, a new twist on the menage a trois.

Les undressed me, complimenting me on my figure, my softness, my perfume and my smooth, white skin. He sure knows what a girl like to hear. After all, he had been one.

I took off his shirt. His arms and chest were covered with tattoos. He had large, succulent nipples, the kind made for feeding babies. Below the nipples were scars where his breasts had been removed. I took a nipple between my lips and nursed, which he liked very much. I pulled off his pants and thought how much of his life he had worn silky, lacy panties: now he wore men’s briefs, which I then took down. There it was, his brand-new cock, with a shiny, red bow tied around it, presented to me as a precious gift. I was delighted with the gift and with Les’s creativity and playfulness.

It was a fat, fleshy penis, remarkably large, considering it was all patchwork. The head looked very realistic, except that there were long hairs growing out of the tip of it, which I found to be a total turn-on. The shaft was quite scarred: it bent to the left, was natural in color and shape and very… unique. Like a typical man he asked: “Is it big enough?” I assured him it was perfect in every way.

He was considering getting another operation to get bigger testicles, and he asked my opinion on the matter. His balls were tight looking, yet very realistic. I liked them just the way they were. I’ve always liked a woman’s mound, and I preferred to think of his balls as an exceptionally mountainous mons. When I ventured down, it was there under his balls that I discovered a lovely treasure—a succulent, large, red clitoris with a huge purple head and a very moist, pink pussy. When Les proudly displayed both sets of genitals, I went into ecstasy, panting and moaning, amazed by my good fortune. What more could a bi-girl want? I scooped his penis into my mouth and gave it a passionate, wet, suck. Then I licked and kissed my way down to his pussy and sucked that clit like I’d never sucked a man’s clit before . . .and indeed I hadn’t. It was wild and strange, like I was in some sort of parallel reality or hallucinating.

I informed Les that I was having the last day of my period. He said, “Great,” found my Tampax string and pulled. What man could be more understanding and unintimidated by a little blood than a man who used to menstruate? He slipped his index finger inside me and went right to my G spot, fingering my pussy like only a lesbian could. Les had no doubt been to bed with many, many women before me. He obviously loved women and their bodies. He had charm and charisma and a woman could trust him and feel safe with him.

Because we were both very anxious for the “big defloweration,” we kept foreplay to a bare minimum. I lit some candles and incense and ritualized the initiation with an invocation of the goddess, a blessing of the new penis and of Les for being such a brave pioneer, and then I gave a brief moment of gratitude. Never before in history has humankind been able to change people’s gender so completely. I felt honored to be one of the first women in the world to try a human-made penis. I prayed that Les’s first fuck be joyful and healing.

We prepared the penis for penetration. In order to make Les erect, he must slide a hard plastic rod into the center of his hollow penis. The rod slipped right in. It was an instant erection, and it felt freeing not to worry about having to get it up and keep it up. Even though I didn’t have to worry about getting pregnant (Les doesn’t have sperm), we decided to use condoms for safe sex and to prevent any infections in case Les wasn’t totally healed.

We considered what the most appropriate first-time position should be and decided I would get on top. I squatted over him, gave him my best kiss ever, took a deep breath and lowered myself onto the new-born phallus. I felt it push up inside me. My throat opened, and I groaned with pleasure. It felt fantastic. It really worked! But after just a few strokes we had to stop. The plastic rod had pushed its way up and out the head of his cock and through the condom. We had to go into the kitchen and cut an inch off the rod. (Thank goodness I owned a sharp, small saw.) In spite of all the modern technology that went into making Les’s dick, we still had to work out a few basics. We laughed about it, and luckily Les did not seem alarmed.

Back in bed we tried we tried a variety of positions. Some worked and some didn’t. The cock would flail right or left, or it would go to a bad angle and slip out. This first time would require some patience and compassion. I wasn’t used to these newfangled penises, and, after all, it was Les’s first time.

Les seemed quite happy with his new sex toy. He told me that watching the pleasure on my face made the pain of all 12 surgeries worthwhile. The penis had “surface sensations.” He could feel my pussy muscles squeezed tightly around it, but most of his sensitivity was still in his clitoris, and I made sure to stimulate it while his cock was inside me—something I’d never done before.

We tried to think up a better system than using the rod. Perhaps we needed a thicker rod or a base at the end of the rod. Les got the bright idea to try using his thumb; so he squeezed it into the shaft. I couldn’t contain my laughter when I saw his cock with his thumb inside it (or his thumb with a cock around it). He joked: “It looks like I’m back to lesbian sex again.” Using his fingers for fucking: “It’s like a fancy snap-on toy I made just for you.”

When I managed to stop laughing, I got back on top and rode the prick/thumb like a champion. Les had more control over its direction, and it was thicker, harder and longer. It felt divine, I was on the brink of orgasm when Les screamed out in pain. I panicked. My heart skipped a beat. I thought I’d ruined his new $50,000 cock. I dismounted, and he screamed in agony as he removed his thumb from his cock. “Shit, you almost broke my thumb!” When we saw that all was well, we laughed hysterically. I mean hysterically.

Suddenly I was overcome with emotion, and my laughter turned to crying. I was so touched by Les’s optimism, good humor and lack of expectations. I was touched by how wonderfully freeky he is and how he lives his dream. I cried thinking about how much physical and emotional pain he must have suffered to change his gender. I cried for all the people who don’t love their bodies just the way they are, for all transsexuals who have suffered, the many who have resorted to suicide, and for all sexual persuasions who are made into outcasts by our society. I mourned Linda Nichols, whom I know I would have liked very much; but by then she was virtually dead and gone. Les told me not to cry. “Look at all the adventures I’ve had and the places I’ve been. It’s been a wonderful adventure. After all, I might not have met you.”

We made love all night, until 7:00 the next morning. After all, his cock could stay hard for 11 hours straight. He told me I was the best fuck he’d ever had. I knew it was true. I was the only fuck he’d ever had. I loved being with him, and I loved being with a hermaphrodite. I wondered if I would become addicted now and no longer be satisfied with regular men or women. Would there be more hermaphrodites entering the world? Would there be a new community emerging, one of men with cunts? Would they become a new political force—women taking over the world, but as men? Would men now be able to become pregnant? I imagined how Les would look nine months pregnant. Would we eventually develop a new awareness of “transgender,” of looking beyond a person’s gender to his spirit, wherein society would no longer try and mold us into being plain, old heterosexuals?

Having sex with Les was a constant mind-fuck. I could put my finger inside his pussy …his pussy?…and feel her balls. His skin was soft and smooth like a woman’s; yet he had hair on his chest. His hands were small and delicate, with a woman’s touch; yet he wore men’s rings. His eyes and lips—so sensual—were framed by his stubby beard. Although he protested, I got him to put on a pair of my high heels. He was the first man I’ve met whose feet were my size and who could walk perfectly in four-inch stilettos. Sometimes he dropped little hints to let me know he was still a woman deep down. He said that when he goes out into the world “it’s like being a spy.”

Sometimes I became the more aggressive, dominant lover. I reached for my favorite dildo, a four-inch rock-hard quartz-crystal cock, and I slipped it up inside his pussy. He was so wet and juicy. Apparently the hormone pills make his pussy extra wet and give it a strong, musky odor, which I really liked. (Hormones also greatly increase the sex drive. Perhaps this is why F2Ms are often notorious womanizers. Unfortunately, the pills are dangerous and very hard on the liver.) His vagina was tight. He has never had intercourse with a man; so technically he’s still a virgin. I imagined a threesome with Les fucking me while he was getting fucked by a guy. Les went for an orgasm.(We wouldn’t want him to get blue balls.) I fucked his pussy with the dildo and gave his dick a handjob while he vigorously frigged his clitoris. It was so far-out to see a man frig his clit. When he came, it sounded like a woman’s orgasm, but with a man’s voice. He was, of course, capable of multiple orgasms.

We took little breaks for drinks of sparkling apple cider, for a luxurious bath together, to kiss grapes into each other’s mouths and for talking. He told me about his life as Linda, the lesbian separatist, when she hated men and avoided them at all costs. I found it a little hard to figure out why someone who hated men so much would want to become one. Les thought it made perfect sense—a classic case of the oppressed becoming the oppressor, with forced integration as a radical therapy.

Since becoming a man, he likes men a lot more and has even been noticing a slight sexual attraction. Perhaps one day this lesbian separatist will become a gay man. Now he feels he gets treated much better and is constantly aware of the male privilege. “After all, men run the world and have their faces on the coins.” Sometimes he does wonder if he may regret passing up the lesbian scene, “especially now since Madonna is hanging out in lesbian bars.” A lot of his old lesbian friends won’t even speak to him anymore.

What does his mother think about it all? It must be hard for a mother to take. “She can’t quite understand it. ‘You were such a beautiful girl. You could have had any man you wanted.’ ” But she is fairly supportive, and she still loves him.

Has it affected his career? He’s never really had one. Up to this point, he’s always been a student. He’s studied art and graphic design, has a bachelor’s and master’s degree in psychology, and at present is a Ph.D. candidate in human behavior. He’s considering careers in either video production, psychology or pastoral counseling. Even though he was at one time a good Catholic girl, I can’t imagine him as a pastoral counselor. Where he gets his money, he prefers to keep a mystery.

I hadn’t laughed, played and fucked so hard in ages. Les announced that his cock felt a lot bigger now that he’d finally used it. I was pleased. We stood looking out my llth floor apartment window into the sky and watched the sunrise with Les fucking me from behind. I had several waves of cosmic, full-bodied orgasms. Time stood still; I became one with Les, the sky and with everything in the universe. When I came to, all I could think of was how beautiful life is. Eventually we drifted off to sleep wrapped around one another, satiated and satisfied.

When we woke up in the afternoon, Les read the Times while I made breakfast. He did the dishes while I made some business calls. Then he blew my mind one more time when he came walking into my room naked with a bunch of carnations sprouting from his cock and said, “Look, Annie; I’m a Greek vase.”

I have the greatest respect for Les. I see him as a unique avant-garde artist whose medium is his body, whose subject matter is sex, and whose message is—as it is tattooed across his chest—FREEDOM.