Warning to those with delicate sensibilities: This story contains adult themes. And by "adult," I mean sexual. Reader discretion is advised.
I met her at work in 1994. I hadn't been out of college long, so I didn't really understand that dating co-workers was much more problematic than dating classmates. She was somewhat matronly looking, but there was nothing un-feminine about her. We arranged to meet at a restaurant that Sunday. In the meantime, while we waited for the week to drift by, I visited with her at her desk after hours when everyone else had gone home. That was the first time I kissed her. She seemed to enjoy it quite a bit, and said, somewhat cryptically, "I was not expecting these feelings."
On Sunday she completely stood me up. She'd gotten busy with other obligations, and since I didn't have a cell phone she couldn't call me. She didn't think of calling the restaurant and asking for me.
Monday, I said "You owe me dinner big time," and she told me she'd love to come over to my place that night or the following night, I forget which. I was feeling really good about this. It was the first time in over a year that I had an actual opportunity to become intimate with a woman, and the heady cocktail of hormones and hopeful thoughts clouded my thinking as she followed me to my place in her car.
On my couch, we got to first base ... then second ... then, just as I was sliding into third, she said, "We need to talk."
She told me she'd never been intimate with a man before. I replied that, wow, that meant either she'd never made love before or that she'd been a lesbian up until now. She sighed, and figured she'd better just spill the beans: "Do you know what an intersex person is?"
Well, I'd heard the term before, but I thought it had something to do with sexual identity. I'd forgotten that it was about plumbing. As she explained, it finally dawned on me that she was saying she didn't have a vagina. She had ovaries, and fallopian tubes, and a uterus, and a cervix ... and a scrotum, and one undescended and one partially-descended pseudotestis, and a miniature penis.
She also told me that she'd lived the first 36 years of her life as a man, not quite fitting in, but that then she discovered the alt.transgender Usenet newsgroup and immediately realized she identified as a woman. She had been transitioning for the past 1-2 years, the last year of which had been on estrogen and the last 6-10 months or so outwardly living as a woman. She'd previously had only girlfriends, including one she'd lived with for 15 years, and thought that after she transitioned she'd be a lesbian; but unexpectedly the hormones made her start to notice men.
At that point, she told me she had strong feelings for me and didn't want to lose her first boyfriend. So saying, she unzipped my pants, gently tugged my penis loose, got down on her knees, and started heading very, very obviously toward giving me a blow job.
For a split-second as she moved in on my groin, she looked like Scott Collins from 9th grade. You don't know him. It doesn't matter who he was. The point is, he was male. The illusion vanished almost instantly but the effect was shocking. Here was a woman who was also a man in a way, who was about to give me a rare sexual treat because she liked me. I knew that if I backed away now, when she'd so vulnerably opened herself up to me, it could devastate her emotionally. But I only had a second or two before she ...
And in that second or two, I had to get REALLY secure in my sexuality, really REALLY fast.
She and I dated for about 6 months. During the 6 months we dated, I discovered that she was genitally dysphoric. She didn't like her miniature penis. So, my one potential opportunity in life to give my girlfriend a blowjob came to nought.
She said her ovaries had actually been kick-started by the estrogen supplements she was taking, and were starting to produce hormones of their own. She also said she was really, really hoping to get pregnant one day. I never did find out if she achieved this goal. She did have boobs, but they were small boobs at the time I was dating her. She'd been on the hormones long enough for her breasts to be well along in the process of developing. Her medical advisor estimated that she'd end up being a C cup when they were done growing.
When sexually aroused, her miniature penis would exude vaginal lubricant. No, I'm not making this up. She was plumbed that way. (I later discovered that without the cowper's gland, semen has a consistency very similar to vaginal lubricant, so maybe her plumbing wasn't as unusual as it seemed to me at the time.)
Since she had no vagina, we had to try other things. Yes, on that first night where I had to get really secure in my sexuality really really fast, she gave me a blowjob. It wasn't the last time. We also discovered that it was extremely enjoyable for me to rub off between her butt cheeks. (Not anal sex — butt crack sex.) She would use this penis-generated vaginal lubricant to grease herself up back there.
But ... remember how she stood me up for dinner that first Sunday? Well, it turned out to be a habit with her. She stood me up more often than she actually showed up for our dates. Finally, after she stood me up 3 times in a row, I called it quits and pushed her out of my life.
In retrospect, I kinda feel bad about that. I was trying to force her into the mold of what I thought a girlfriend ought to be (in this case, punctual, with me at the top of her priority list), instead of accepting her for who she was (in the words of Rodgers & Hammerstein's Oklahoma!, she's just a girl what cain't say no). She was one of the sweetest women I've known, and it would have been nice to still have her in my life, even if I could only have a tiny sliver of her at a time.
I did meet her again (once) after she'd had the sex-reassignment surgery. (And no, we weren't dating at the time so she didn't show me the surgeon's work.) She'd volunteered to help me move out of my apartment and into my first house. Sadly, as had happened all too often in the past, she showed up hours late. She managed to help me pack one box before she had to turn around and leave again.
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