True Stories: A Helping Hand

To conquer my virginity, I got help from a sex surrogate. So did my best friend.

By Phil Goldman

When we were both twenty-two, my friend Scott and I decided that enlisting the help of a sexual surrogate was the best way to lose our virginities. We couldn't seem to get rid of them on our own, and this was beginning to seem like a terrifying predictor of never-ending failure.

Scott owned a small, struggling comic-book store in Cambridge, Massachusetts, and I was living in his spare room, having only recently fled my parents' house. After spending all day "working" in the store — the kind of place where maladjusted kids came to debate the merits of X-Men instead of buying anything — we'd sit around smoking pot, listening to music and talking (in completely hypothetical terms) about girls. When Scott told me he was a virgin, I was relieved to learn that I wasn't the last one. And it struck me that I really, really wanted the last one to be Scott.

With our limited social skills, it was hard to figure out how to meet girls, much less get them in bed. Around town, Scott and I saw plenty of women sitting alone and looking vaguely bored, but none of them pushed aside their books and iced lattés to rush to our sides. While we waited for this miracle to happen, I started browsing the personal ads, hoping to find something like "Hot, nurturing, extremely patient woman seeks obese, self-loathing virgin who masturbates too much." Instead, I found an ad for the Institute for Sexual Surrogate Therapy.

Anxious to get an edge on Scott, I called to make an appointment. It turned out that before I could meet the surrogate and get down to business, I had to meet with Dr. Klein, the psychiatrist who ran the place. I wasn't sure what his qualifications were, but when I met him, he seemed impressive enough. His graying comb-over and wide, thick sideburns gave him an air of professionalism, and he sat behind an imposing glass desk in front of a wall of gleaming plaques. Still, to me, he was basically a medically licensed pimp.

Dr. Klein leaned forward, hands clasped, and told me it was a damned good thing I'd come to him when I did. "In your early twenties, there's still hope," he reassured me. But had I waited much longer, it might have been "disastrous."

From now on, he told me, I was to masturbate no more than twice a week. And before I could meet with the surrogate, I had some serious work to do. Dr. Klein reached into his desk drawer and pulled out a large, rubber, flesh-colored phallus, complete with bumps and veins. He cradled the bulbous scrotum in the palm of one hand.

"You've got to learn how to control your penis," he explained. "Work the penis, using short strokes, in three discrete sections." He demonstrated. "Don't spend too much time on the head or you'll get too excited. If you feel like you're losing control, simply stop, pull your hand away completely, and let yourself go soft." He let the phallus droop in his hand. "You need to learn to last at least twenty minutes. I suggest you buy some sort of egg timer."

I nodded. An egg timer. This was the kind of practical advice I could really get into. Sensing that I was keeping up with him, Dr. Klein moved from beginner to intermediate skills. "After you've practiced for a while, and have achieved a certain level of competency, you can move on to what we call tromboning: work the entire penis at once, base to head and back." He gave the phallus some full, confident strokes. "Eventually, you can even mix the methods. Have fun. But not too much; remember, twenty minutes. Just see what feels right for you: long strokes, short strokes, long, short, long, long, short, short, short, looooong..."

Clearly, it was called "tromboning" for a reason. He was really getting into it, playing the phallus like it was a jazz instrument. Watching him, I found myself getting a little aroused. I slid down lower in my chair and crossed my legs. 

FIND MORE
True Stories: March Madness - I went to Spring Break a virgin...
My First Time - "I was born and raised in a Hasidic community..."
The Tokyo Stripshow Tryout, by Phil Goldman - I went to Japan looking for work. This was not what I had in mind.