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.
“Would you like to try?” Dr. Klein held the phallus out to me.
“No, I’m good,” I said. I was anxious to try out the techniques, but I didn’t particularly like the idea of holding it so soon after him.
“Suit yourself.” He dropped the phallus back into the drawer, where it landed with a thud. Then he leaned forward. “Now… let’s talk price.”
When I told Scott, he immediately called to book his own appointment.
Three days later, after his first session, we compared notes. Dr. Klein had given Scott the same lessons, and the same homework assignment, but he’d told him he could practice three times a week, instead of two. Scott made sure I knew that he considered this a personal victory (I wondered, though, if the doctor just thought he just needed more practice than I did). Armed with our own egg timers, we completed our assignments with focus and diligence. Living with a fellow student was helpful, even motivational. We regularly compared our best times.
Finally, after weeks of perfecting my solo performance, Dr. Klein decided I was ready for the next step. I sat in the Institute’s waiting room, psyching myself up to meet my surrogate: the woman with whom I would be having sex. I was going to have sex!
But not yet. Today, according to Dr. Klein, was a day for “getting acquainted.” There was a master plan at work here, and I had to respect it. I was starting to worry that this experience might be a little too clinical, so I was relieved when the door opened onto a pretty standard therapist’s office. There was a couch, a chair, a filing cabinet — and a rolled-up futon in the corner. The receptionist told me to make myself comfortable; my surrogate would be with me shortly. I panicked. Where should I sit? Should I roll out the futon? Would that be helpful, or presumptuous? I decided to sit on the couch, with my arms across the back cushions, my right ankle resting on my left knee. I hoped I looked casual and confident, like there was nothing unusual about the situation. Still, my eye kept wandering over to the futon.
There was a light knock on the door, and suddenly there she was: my surrogate. With her long, lean body, tightly curled blond hair, jeans and black leather jacket, she had a sort of casual biker-chick look. I breathed out. Thank God, she was attractive. I really didn’t want this to be any more difficult than it had to be. Her name, she told me, was Jan. After about twenty minutes of small talk, Jan suddenly stood up, clapped her hands together and announced, “All right, let’s get to work.” She rolled out the futon with her foot.
“I, uh, thought… Dr. Klein said this was just a ‘getting acquainted’ day…” I stammered.
She laughed. “I’m only going to give you a massage, to get you used to me touching your body. You don’t have to do a thing. Just get undressed. Leave your undies on, though.”
I stood up and tentatively began to disrobe. When I took my shirt off, Jan’s eyes widened. “Man, are you hairy!” she said.
“Is that going to be a problem?” I asked weakly.
She shrugged and told me not to worry about it. “A lot of women,” she said, “find it sexy.”
“Do you?” I asked, hoping.
Later, when Scott got home from his own “getting acquainted” session, we realized we both had the same surrogate. Maybe Dr. Klein had planned it that way for some mysterious therapeutic reason. Or maybe Jan was the only surrogate who worked for him. Either way, once Jan found out that Scott and I were roommates, she sensed our natural competitiveness and played us off each other. She would fill us in on each other’s sessions, telling us how well the other had performed. Sometimes, she would make it sound like we were getting away with something, going beyond our prescribed allotment of sex. “Oh, we shouldn’t be doing this,” she would tease. “Don’t tell Scott, it’ll be our little secret.” After our sessions, we’d brag about our milestones. Soon, it became unclear which was more important — losing my virginity or beating Scott.
“Jan said you were ‘very sensual’ in your last session,” Scott told me, using bitter air quotes, as soon as he walked in the door one day.
“Yes, I was,” I admitted. Yet I wondered what else she’d told him.
That session had been the first time in my life that I had access to a naked body other than my own. Lying on the futon, in all her naked splendor, Jan had waited for me to touch, explore, do whatever I wanted. I began with simple, tentative touches and kisses. She didn’t stop me. I went further. She didn’t stop me. I became lost in her flesh, her smell, her texture. It seemed to be working for Jan: her head thrown back, eyes closed, her breathing getting harder with an occasional gasp. With increasing bravado, I slowly approached her vagina. Was this allowed this session? Only one way to find out. I massaged her inner thighs, my fingers gradually coming closer… closer… and I was in. Not only did she not stop me, she was responding. I responded to her responding to me. And it was good.
So good that Jan took hold of my penis. But my penis wasn’t ready, and recoiled. Jan stroked and gently pulled, but I wasn’t getting hard. I wasn’t getting hard! What was wrong with me? She tried for some time, but it became obvious that it wasn’t heading anywhere. Jan took her hand away.
I felt like a failure. She said it was okay, I shouldn’t worry about it, I should forget about it, I should go back to doing what I was doing, that it felt good. But when she remembered to check her watch, she jumped off the futon, threw my clothes at me and told me to hurry, that she had another client waiting. She sprayed herself with some sort of cooling body mist, got dressed and kissed me sweetly before shuffling me out the door.
“What else did Jan tell you?” I asked Scott. I inspected his face for any hint of a smirk or superiority. I found nothing. She had no reason to tell him, and neither did I. She was discreet. I was ashamed.
In subsequent sessions, the problem slightly improved, but not nearly enough. I could, eventually, get it up, but I couldn’t keep it up for any reasonable amount of time. Jan tried to get me to relax, not think too much — an impossible request. And the more I thought, the worse it got. I was so caught up in my head that I could barely feel my penis anymore. I could see Jan touching it. I could see her sucking on it. I’d always dreamed of a woman’s head bobbing up and down on my penis. But I couldn’t enjoy it.
In the meantime, Scott kept me apprised of his progress, and I made him think I was keeping right up with him. Lying, lying, lying, until the day that he came home and tell me how he lost his virginity: doggy-style, Jan leaning over the couch.
Scott beat me.
Jan was patient and supportive, but she didn’t provide me with any answers. Neither did Dr. Klein. Where was he? Jan must have kept him up to date about my progress. Shouldn’t he have addressed the issue? He was a psychiatrist, or psychologist, wasn’t he?
The sessions were finished, but I wasn’t. Dr. Klein suggested that I sign up for another round (so he did address the issue) but not until I was paid up for the first. I eventually returned a year later, but by then Jan had moved on. I would have liked to finish with Jan — for years I fantasized about running into her on the street and getting a room, but never did.
The new surrogate was as patient and fun as Jan, and she knew a trick that Jan didn’t, the trick that did the trick. She told me to forget about everything, about “performing,” about pleasing her and just focus on my own sensations and pleasure — then she put a blindfold on me and placed me in the middle of the room, naked, while she rubbed her own naked body all around and over mine. Once I became aroused, she took me into her mouth and the rest fell into place.
Scott and I continued our competition for years to come. Who was the first to have sex outside of surrogate therapy? It took us both quite a while, but even with my delayed consummation, I was the first. The thing was, surrogate therapy taught us how to have sex, but not how to get laid. Or how to get into a relationship. Or how to maintain a relationship. (I’m still working on that.) Who was the first to be in a relationship? Scott. The first to get married? Scott, which meant he was also the first to get divorced. We weren’t sure if that counted as a win or a loss.
This piece originally ran in 2010.