I'm that part of humanity that Freud glossed over.

I wasn't like the other boys. Yes, we played ball. We scoffed at girls. We taped little mirrors to our shoes and tried to look up their skirts. We drew pictures of what we thought that space between their legs really looked like. We competed to see who could pee the farthest. When there were girls around, we watched them stare in awe as we stood and turned our backs to them and sent great yellow arcs out in front of us. It was great. The envy in their eyes was unmistakable. I relished it.

While I stayed up at sleepovers wondering with the guys about these strange and annoying things called girls, I found my thoughts turning to that very thing those more perverted of us were so ragingly curious about. That wasn't the quandary, though. For some reason, I really envied those things. I wanted one of my own.

And thus, my vagina envy.

The first time I got a sense of being like a girl in the genital sense was when I made my penis disappear.

Long before I knew anything about drag queens, I learned to tuck it between my legs. As a teenager, I was fascinated by accounts of women who could just squeeze their legs together and come that way. If only I could have. When I see women in public with crossed legs, especially with their feet bobbing up and down, I wonder, are they doing it? Are they drenching themselves in public? And above all, are they getting away with it? Honestly, I thought, if I had that skill I would be the happiest person alive.


So I tucked my member between my legs, watching it momentarily disappear, and I momentarily had my coveted vulva, and I squeezed. Over and over, day after day. Finally, I came! With my legs pulled up, my fingers rubbing my mound, I squeezed and moved my thighs and creamed all over between them! I reached behind me, scooped up a wad of my cum, and spread it on my male twat. How I wished I could lubricate like a woman! This became my favorite means of coming. Either lying down, standing up, or sitting, I could watch as I held my fingers like a woman and rubbed my cunt. It was delicious, rubbing in circles, and I could feel it at the top of my cock as it lay scrunched between my legs. And I also wondered, what would it be like to have a woman's face right there, licking me as if I had the real thing?

But still, it was just a penis between my legs. It was not the real thing.

Stacy was my first girlfriend to find out about it. It happened somewhat by accident.

We were in the bathroom. She was naked from the waist down. Her pussy was smooth and hairless, and I could see the seductive slit in the middle. Watching her curl her hair in the bathroom, I sat down to take a pee.

"Mike, why are you sitting?" Stacy asked.

I tucked my penis neatly and proceeded to do my thing.

"Is that how you usually do it?" she asked.

"Sometimes. Sometimes I stand."

"Well, you look funny."

"I like how it feels."

"Are you a transsexual?"

"No. But a guy can fantasize, can't he? Do we men have to be so set in stone? Can't we have a little vagina envy now and then?"

"What's so great about having one of those?" Stacy asked me. "Sure, they've got some privileges, but they're messy, they bleed, they discharge--you men just have no clue." And she folded her arms over her chest.

"That's right," I said. "Our first experience out of the womb is having wet, squishy vaginal walls bathing our faces. No wonder we spend the rest of our lives searching for them. Try being born from a penis and you'll understand."

"So why not just get a sex change?"

"I want something that a vagina has but a penis hasn't. I want to get wet and squishy. I want a warm, soft place to stick my fingers."

"Like that's all we women ever do? Stick our fingers there?"

"Maybe it's the grace of walking around without something flopping around, or not having to get jackknifed in my underwear while I get a sleeping erection. I'd rather savor the envy than have the real thing. I like the mystery. How many people would really want to be President, as much as they think about it? Or really be a rock star?"

"Maybe you should see a therapist about this."

"Oh, I get it. A woman fantasizes about having a dick and we all nod our heads in approval. A man envies a pussy and he's some kind of a head case. Figures. It just figures. Even women laugh."

"Well, I tell you what, Mike. You go through a few menstrual periods, some cramps, discharges, infections, and having to look over your shoulder every time you walk outside at night, and then you come back and you tell me you want what I've got."

I had to admit she had a point. But still, it didn't diminish my envy.

Eventually, that was the end of her. But she introduced me to a friend of hers, a wild tomboy who was a gender studies major and "not much into conventional sex." Susan was a ravishing blonde. We began to argue over gender issues as soon as we met, but it did not diminish the attraction between us. Instead, it made it stronger. And Stacy must have been a blabbermouth, because when Susan took me up to her room during a party on our third date, she put my hand to her crotch and told me to feel what was there beneath her dress.

"Is this for me?" I asked when I felt the outline of an organ that was certainly not female.

She nodded. "It's for me, too. Your envy fits perfectly with mine. Shall we cut out of here and try it out?"

"And go where?"

"Somewhere I can stick this into you."

I led the way downstairs, stopping midway to turn around and feel her again. "Are you going to make me suck it before you put it into my ass?"

"I'm gonna make you suck it, lick it, deep throat it, and then I'm gonna make you bend over and take it up the ass."

We hurried outside, to her '73 Duster. Susan took me for a ride. I curled up close to her, feeling her tool through her dress. When we got to a secluded spot, she made me suck her in the car. I reached in and pulled the rubbery thing out.

Then Susan grabbed my head and forced it down.

"Suck my dick," she ordered. As my head bobbed up and down, I knew she was feeling vibrations on her clit from the movements of the dildo, and she moaned and moaned until she let out a final scream. I had to rearrange my own rock-hard cock.

"Get out," she ordered. As I did so, I saw Susan dig in her purse for something. When she got outside, she ordered me to bend over the car. I felt her hands unbuttoning my jeans and pulling them down. My cock sprang free and bounced up and down. I wanted her to touch it so badly.

"Spread your ass for me," she ordered. With glee, I reached around and pulled my cheeks apart. I felt her fingers rustling between my globes, moving through the hair, and settling on my hole. Then I felt something cool and slimy being spread there.

"Are you a virgin back here?" She knelt down and looked at my vulnerably posed hole. "Yep. Tight as an obedient nun. I'm gonna turn you into a girl tonight." And she slapped my ass hard. I yelled out. She slapped it again.

“You like that, don’t you, you naughty girl?”

“Yes! I do!”

“You’ve always wanted to be on the receiving end. You want to know how a woman feels when she’s being entered, when she has to spread herself for you and make her vulnerable. You think it’s a big joy to us, don’t you?”

“Yes! I mean no! I don’t know!”

I turned around to look at her. It was almost a ridiculous sight. Her dress was off, and a large dildo stuck out from a harness around her waist. Gobs of brown hair peeked out from behind it.

“Turn around, girl,” she ordered. And she slapped my ass really hard.

Then I felt her cock touch my hole. I held my breath. Then she carefully pushed it in. It hurt. I pushed out with my muscles as she pushed in. But then the pain turned to pleasure as I quickly relaxed.

I loved the feel of being filled up and roughhoused by a woman. Our fucking settled into a rhythm as I opened my hole when she entered, and closed it when she pulled out. Open, close, open, close. I was so fascinated with being entered that I didn’t grow tired of the opening and closing. And soon I spent gobs of cum all over her shiny fender.

Susan cleaned off her dick and put it back. We made out on the trunk of the car for an hour, but she never once touched my dick. Instead, she rubbed hers on mine, and I was soon left with a sticky pair of underwear. At one point, she even stood up, pushed her dick aside, leaned back a little, and pulled her clitoral hood upward. To my delight, I saw a yellow stream arc out in front of her.

"That is so amazing," I said.

Amazing, but not perfect. She dribbled on herself a little as her pee died down.

"I'm still working on it."

For the six months we dated, she didn’t touch my dick at all. "I want to have the dick in this relationship," she told me. And during our time together, she did. She put it in my mouth and ass almost every time we got together. She rubbed it on mine. I can't say I hated it, but despite the novelty, my ass and my mouth weren't the vagina I was really looking for.

Then there was Gabrielle. I met her at an art show, where we were admiring line drawings of nude women. She loved looking at both men and women, especially women. Her home was filled with framed prints of women, women, women. Many of them naked. Some embracing other naked women.

"But just because I find women beautiful doesn't mean I want one," she assured me.

Ah, so maybe she would understand me.

Gabrielle, a short, dark-haired French woman with small breasts, unshaven legs and armpits, a huge black bush, and wide hips, loved to bring herself off on my leg.

"The first time I came with a man, it was on his leg," she told me.

"Why?"

"It's easier," she told me. "I've always come by rubbing. Against the bed, the chair, the table … the washing machine."

It was when she woke up one morning and reached for my penis that she learned about my fetish.

"Oh, Mike, what have you done with him? I want to kiss him and wish him a good morning."

"Sorry," I said. "I turned into a woman overnight."

"Oh? And where's the opening that goes with it?"

"It'll arrive tomorrow. Just be patient."

To my surprise, she put her fingers between my legs and rubbed me there, using circles. The pressure affected my penis, hidden beneath my thighs. I loved it, and so did she. We masturbated each other that way, and it was the beginning of an interesting sex life. Gabrielle liked my vagina envy very much.

I loved Gabrielle's sense of humor. Once, she analyzed me like a psychiatrist, with the stereotypical glasses and notepad, except she sat across from me, naked, with her legs spread.

"Tell Dr. Gabrielle Freud vy you crave zee vagina so mahch" she would say with a German accent, her open vagina gaping at me from the black forest around it.

"I like zee freedom of not having anyzing bouncing around between my lags," I would say. "I like zee ease weethe wheech I can hump zee furniture."

"I believe zat your condeetion eez a sign of mental health," the doctor told me once, her finger deep in her own cunt. "Eef more of you men had it, zee vorld vould be a happier place. You are cured."

One day a few weeks later, she jokingly said, "Would you like me to castrate you? Turn you into a little girl?"

We liked to compare ourselves in her full-length mirror. We could see her pouty pink lips poking through her black triangle of hair. Her mound was fleshy, mine was flat.

"Don't you like the quiet of it? The repose? Nothing bobbing around embarrassingly between your legs?" She would turn to me and caress my own triangle, with up and down movements, and with circular movements. She would put her fingers to her nose, telling me how wonderful my pussy smelled.

She would sink to her knees and put her face to the recess between my legs. Licking up and down, she would feed from me with the expertness of an experienced cuntlicker. I held her face there, bucking against it, while I saw myself in the mirror.

Although we fucked conventionally, Gabrielle loved the humping the most. It must have been strange to her--a man moving like a man, moaning like a man, and holding her like a man, yet lying on his back, carefully tucked, with knees slightly bent, while she straddled him and rubbed her large mound on his. I found that it stimulated my penis, and I could come like that. She started to call me Michelle as she came again and again, coating our hairy mounds with her slick cum.

The thing that really turned me on was when I was in that position and she licked me up and down. I held her head lovingly, as many women do when they are being eaten, and told her in dirty terms to lick my pussy, suck my juicy cunt, and stick her tongue all the way up my twat.

But Gabrielle was obsessed with women. When we were together, we were women. We talked about the beauty of women, the intelligence of women, the grace of women. I found that I loved it. My penis grew hard and tingly as we talked of our love for women. With my male organ out of the way, I found that I had to pay attention to other aspects of sex. I couldn't just stick it into her. I was forced to notice the rest of both Gabrielle and me. Making love to just her arms, her hands, and her neck became an exercise in sex. Just touching each other's upper halves could take up to an hour. I was discovering what I could do when I didn't have penetration in mind, and I liked it.

But then she bought me dresses to wear. She bought me frilly underwear, made me wear stuffed bras, and bound my genitals at all times, even during a trip to the beach. I began to fear her.

"Michelle, dear, we don't really need these things," she would say to my genitals as she bound them and pulled them back. "There. Now you are a woman again, just like we like it."

I began to fear castration and penectomy. And deep down, I realized that I didn't want either of those.

One day, while she was curling her hair in the bathroom and my poor penis was in pain, I walked in, undid my penis, pointed it at the toilet, and let loose with a stream of piss. Standing.

"Gabrielle, dear, Michelle often likes to be a man. And she's not a lesbian, and she's not about to part with her dick."

I ended the relationship. As much as I loved Gabrielle, she was really looking for a woman. And I was still looking for something I did not have, nor ever would.

Five years passed, during which time I stayed away from women and their vaginas. I indulged my fantasies in private, writing about them and sketching pictures of me both with my penis and with a vagina. I grew lonely and bored. I watched dirty movies where men got fucked in their butts by women. It was interesting but did not hold the appeal it had in earlier years. Eventually, I began to lose interest in my old envy.

And then came graduate school. No, there was nothing in the American literature courses that renewed my vagina envy. As an artist's model for a life drawing class, I ran into Susan again. She was something of a professional student, and was now an art major. I watched her as she drew my naked body. Susan was forced to look at me as a man now, if only for artistic reasons. I watched her the most of any of the artists. At one point, I caught her glancing at my penis, which stood out embarrassingly hard. Susan grinned.

I asked her out after class. She told me she was still single, still interested in "the kind of stuff you and I did years ago," but not as much. She had discovered her vagina somewhere along the way—

"And I really liked it," she said. “I started liking my vagina.”

“And I’m happy with what I was born with.”

"Was that hard-on in class because of me?"

"I think I was glad you were finally looking at it."

Susan looked me in the eye. "I'd like to look at it some more, if you don't mind."

Later that night, I undressed and let her look at it some more.

"Look at the beautiful architecture of this thing," she said to me. She ran her hand along its length. She took the head in her fingertips and caressed it. "I love this spongy tip. I love it!" She sucked it deftly into her mouth.

"Do you still want one of these?" I asked.

"Are you looking to give yours away?" she joked.

"No, I'm just wondering."

"No, I'm happy to touch it on someone else."

Susan undressed and lay next to me, putting my throbbing organ to her cunt. Her hairy mass tangled with mine. Her cunt was so wet that I could smell its beautiful fragrance from where I was. She rubbed against my cock a few times, then guided it to her cunt. For the first time in years, I was inside a woman again. It felt wonderful to be encased in warm, tight, wet flesh, especially with the rest of the woman attached to it.

We fucked like man and woman from then on. I told her about my own envy in more detail. And Susan still had something left of her cock fetish. Sometimes, before we'd go out for the evening, she would rub against me to let me know that there was something strapped on beneath her dress. Afterward, she would sneak me into a stall in the men's room and give it to me in the ass. Afterward, she'd use the urinal, which still amazed me. This time, though, she could do it perfectly. Once she fucked me in front of two of her friends. We even made a short movie out of it.

Susan and I eventually married. On our wedding night, there was no sign of her cock. Would she get it out and use it on me, I wondered?

When she came out of the bathroom, dressed in brand-new, silky panties, I still saw no sign of it. She crawled into bed and took my cock deeply into her mouth, sucking on it like a baby, noisily and hungrily. Before I could relieve myself in her mouth, she told me to turn around for a 69. After I did so, she tucked my male parts between my thighs, and put her face into my crotch.

We settled into a rhythm, licking each other up and down, up and down. Below me, I squeezed my cock lightly between my thighs. Susan reached around and jacked me off from behind. As she licked my cunt, she was stroking my cock. When I finally came, about four orgasms behind her, my face was bathed in her juices and I was bucking against her face. I came in her palms. She spread my thick fluid on my pussy and licked it off.

After a short recuperation, I climbed on top of her and gave it to her missionary style. After that, she took out her beloved cock, strapped it on, ordered me onto my stomach, spread my legs, commented on how beautifully vulnerable I looked with my hairy male hiney about to be used, and fucked me in the ass.

There is no way I will ever know what it feels like to have a vagina, any more than Susan will get a true sense of what it's like to have a penis. I've learned that I can keep my penis and also pretend that I don't have one. And we don't mind anymore that I don’t have a vagina and she doesn’t have a penis. We're happy to approximate them as best we can.