Item number 2: "I lost my virginity in a tree house on long island with two fat women at once."
(And the survey says...)
In fact, I wrote up the whole thing for the first issue of Hanne Blank's 'zine, "Zaftig" (now defunct, unfortunately) some four odd years ago... and I mean "odd". Here it is in its entirety, as it was originally published:
I've often had to spin the bottle when people ask me about the "first time". I mean of what? The first time I got sexually stimulated looking at a fat girl? That would be age 11, and the woman would be Cass Elliot...on television, of course. On a special called "Don't Call Me Mama Anymore", if my memory hasn't been clouded in the intervening years. I wonder whatever happened to that special?
The first time I had serious fantasies about fat women? Well, that would have to be when I first read a passage in Anais Nin's "Delta of Venus" ("Pierre", I believe) in which a very large older woman gives a young teenaged boy his first blow job. I actually had it timed so that I could start reading that passage and orgasm about the same time as the boy in the story did.
Strangely enough, this ties into my first visual erotic experience. Instead of hiding playboy's under the bed, I had a copy of Rubens work sitting on my bookcase, in plain sight. People probably thought it was a sign of intelligence, not realizing that I was beating off furiously to "Angelica and the Hermit" late at night.
If this gives the impression I was a classic example of the late 70's nerd while growing up...well, it's a fair cop. My social life was very erratic and downright non-existent until I got braver my Senior year in high school, deciding that if you were alienating people by being smart in the first place, you might as well be having FUN with it. My reputation grew as a person with a weird sense of humor, but at least I left that place having left an impression.
Which, in it's roundabout way, brings us to the point in time of the traditional "first time": The night I lost my virginity.
I was about to graduate high school, and was 18 and a half. I had FINALLY started to date this lovely plump woman named Regina, who gave every indication that she was open to the idea of actual sex. I was moving cautiously, because I didn't want to scare her off by being over-eager.
It was going to be a classic friday night date at the movies. I had a feeling it *could* happen, and after an embarrassing episode the night before involving my very first condom purchase involving a loud exchange with a pharmacist in front of what turned out to be three elderly nuns (I'm a recovering catholic, by the way), I was as prepared as I thought I could be.
When I arrived to pick Regina up, she dropped a bombshell...she had promised her friend, Elyse, that she could come as well.
Needless to say, I handled this as best I could. I admit it was very hard (no pun intended!), as this was as close to getting laid in the 7 and a half years since puberty hit me like a truck, and I was seeing it vanish before me.
So we walk over to Elyse's house, and she comes out to meet us.
I've had my moments of strong sexual attraction before this, but this was different. I felt my knees turn to rubber, by head spun, and my stomach felt like the planet had whisked itself out from under me like a rug being taken out to be beaten. It was my first case of mind numbing, world shattering, take me by the crotch and throw me over the house LUST.
She was short, blonde, very tomboyish (I'd call her "butch" today), wearing a matching pair of sweat pants and a sweat shirt, and VERY well rounded. She had this cute little round nose and sparkling eyes, and I just wanted to sweep her up and...
...and she was my girlfriends best friend. That meant there was nothing I could, or should do, according to the rules of good taste that I worked hard to teach myself.
The movie was an interesting experience. I couldn't tell you what it was, as I was too busy being very conscious of the fact I was sitting between two very attractive girls, one who was making my blood pulse in a way that made me think I was having some sort of seizure. At one point Elyse rested her hand on my knee briefly, and I thought I was going to come right then and there.
Afterwards, Elyse suggested we grab a bite to eat. Being poor teenagers that meant a walk over to Jack in the Box, where we talked about various things, making jokes and what we thought were risque comments.
We had started the walk back, when somehow (yeah, right) we were all talking about sex. Elyse was talking about her experiences (and you can imagine what it was doing to me, though I was trying my best to be cool about it) when she said: "All I need now is someone to take my virginity".
Without thinking (if I had been, I would NEVER have said this!), I replied: "I would be glad to volunteer."
When I realized what I had said, I almost slapped my hands over my mouth. I mean, it was impulsive and rude, particularly in front of Regina, to make a comment like that. My only hope was that they thought I was joking.
Elyse gave me this odd smile and said, "Only if you have rubbers."
Thinking that I had gotten away with the "joke" cover, I decided to pull out the rubbers I had so valiantly achieved in the face of extreme mortification. Now, that WAS a joke.
Elyse took them from me, took my hand, and said "Let's go!"
At this point I was cracking up. It was mostly from relief at having turned it into something funny (Regina didn't look very upset...in fact, she was grinning as well), so it wasn't until she had run me a good distance that I started to object to being dragged along. Okay, so I was getting off on the fact she had my arm in this strong grip, and I was milking it for as long as I thought I could get away with it.
We were in this small wooded area when I stopped, and made some comment about it being a joke. That's when she took me by my head and kissed me, full on the lips.
I tried not to react and pull away. Bullshit, I sank into it like an exhausted man into a bed, wanting to snuggle into her forever. It wasn't until I felt Regina slip her arms around me that I pulled away...and then Regina kissed me, Elyse still holding me.
That's when I began to wonder just what the hell was going on.
The rest of the walk was a blur, with us walking hand in hand in hand. I started to think I was delirious, lying in bed somewhere constructing a happy fantasy based on one of the Anais Nin stories I frequented in my never ending search for more exciting self stimulation. I don't remember getting there, but Elyse was kissing me again in Regina's back yard.
Her parents weren't home, and her younger brothers were off at a friends house. Still, Regina didn't want to "do anything" in the house (were we going to DO something? I wondered), so we walked to the back of a long lot to where it was partially wooded. You got a lot of those kinds of places on Long Island.
We were looking for a suitable place to sit, when Elyse said "How about the tree house?" I looked up, and sure enough there was a classic crude structure built by Regina's brothers, a good ten feet off the ground, a hand made ladder leading up the side of the tree.
We climbed up and settled in. I kept getting confused about the etiquette, not realizing that I had suddenly taken a path where I was pretty much on my own to figure things out. We snuggled, and I kissed Elyse, then I'd kiss Regina (Regina and Elyse didn't interact much beyond snuggling). Then Elyse stood up, and before I knew it her sweat pants were descending over her hanging belly, her full hips, her...
Before they were halfway down her thighs, my face was buried between them, licking and tasting her. I had always wanted to do that, and that alone almost made me come... yet again.
I think Elyse was surprised...it wasn't for many years that I realized that when she talked about having done everything, she wasn't talking about all the things that could have been done to HER. I'm sure I was clumsy and inexpert, as there's only so much you can learn by reading, but she wiggled happily for a few minutes, then demanded that I fuck her.
Strangely enough, actual sex was only a minor point of the evening. I definitely took her virginity, but it was too tight and painful for her (despite the care I took...I had heard about how painful it was for virgins) for her to do it more than a minute. That's she she suggested I take it out and rub it under her belly fold.
With Regina whispering encouragement and Elyse kissing me and holding me in her large, strong arms, I didn't last long. I had never thought about using a fold of fat like that in any of my fantasies, and it was amazing how it felt more like what I imagined fucking would feel like than fucking did.
So there it is...my first time was with two fat women in a tree house. If there ever was a clear sign from above as to how the rest of my life would go, that was it. Looking back, it's obvious that Elyse was the first exhibitionist I had ever met, and Regina the first voyeur (I can't describe this happy look on her face while she watched us...she really WANTED us to have sex in front of her).
The three of us had several other experiences (Elyse is also the first fat women I had sex with while in a swimming pool), and then circumstances (not all of them pleasant, I'm sorry to say) caused us to drift apart.
As each subsequent first has brought me a great deal of joy, I often think about that time, and wonder what they're doing today, and if I'll ever see them again. Even as I'm typing that, I knock on wood: With this kind of luck, I suspect that you'll agree that anything's possible.