Love & Sex

My First Time

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Male • 33 years old • Chicago, IL

She was a former coworker who kept popping by the store every so often; even though she hadn't liked working there, she still thought of it as her favorite bookstore. Everyone had gotten along with her pretty well when she was a fellow employee. In any workplace, of course, there are several valid reasons to not try to get too friendly with a coworker of the opposite sex. Once that person becomes a former coworker, you both get to behave like normal human beings again. So I was allowed, finally, to notice that she was twenty-four and pretty in a youthful way that could let her pass for a teenager.

At some point in chatting with her during one of her visits to the store, she mentioned her MySpace page, and how much fun she was having with it. Not long after that conversation, I logged in to my own account, found her page, and sent her a message. A couple of email back-and-forths later, she suggested we start hanging out. So we did.

She had me take her way up north on Highway 41 to her favorite all-night diner. We went up to the attic/office in her parents' house to watch Gimme Shelter — she had a huge crush on Mick Jagger. (Her father actively hated Mick Jagger; while walking by at one point, he saw Jagger on the screen, flipped the bird at the TV set, and walked off without saying a word.) We hung out and listened to music in my parents' old house, which sat mostly empty while the housing market was just starting its long free-fall. She asked me to take her to an exhibit of new art on the U. of Chicago campus in Hyde Park.

She told me about her boyfriend. How she'd met him online. How he was a really talented bass guitar player, who practiced several hours each day, even on days when she drove out to see him. Later, she told me about the night her car hit some black ice and skidded off the road while she drove home from his place, and how when she called him for help, he broke up with her over the phone.

A week later, she called me and asked if I'd like to sleep with her.

"I looked for a boyfriend, and I found one," she explained, "but I'm done with that for now. I just want to have fun, but I'd like to do that with someone I know and trust. I'm usually attracted to big guys, and you're kind of a big guy. Besides, you're really nice."


Illustration by Thomas Pitilli


I didn't know what to say. A pretty girl was offering herself to me sexually because I was nice to her. She found my physical size attractive, rather than intimidating. She was from a different universe than the rest of humanity.

We went out to dinner Saturday night. She said she could tell that there was something I wanted to say over the phone but hadn't. I told her that wasn't really the case; I was truly left speechless.

Back at my place, I discovered that she had made some assumptions about me that weren't really true. Her underwear was an actual set — matching bra and panties. They were nice, certainly, but what mere fabric could compete with her beautiful body? I removed her bra, and took a moment to admire what it hid.

She said, as though apologizing, "They're really small."

I replied, "They're perfect." I wasn't flattering her.

She wore perfume. Too much perfume. Way too much perfume. I thought about giving her a lecture on pheremones, and how all she really had to do was bathe regularly and let her natural scents take it from there, but managed to stow that away for another time.

Afterwards, she said she'd had fun but didn't want to spend the night. She did still live with her parents, and wasn't ready to make it obvious to them that she was sleeping with me. It was still only about midnight; I was reminded of high-school-era curfews. I suggested that she not spend the night but not leave yet either. Perhaps we could even go another round. But she'd made her decision and was sticking to it. I drove her home. She kissed me goodnight in the car.

A week later, we got together again. She asked me to drive her to a sex-toy shop. She was pleased with herself for having found one which actually specialized in dildos and vibrators rather than bondage equipment. The young women running the shop were very helpful, and answered all her questions about which design would stimulate which body part. She picked a design called "Lola" and we went back to my place.

We went straight into my bedroom. Complaining about the cold, she said that she would leave her blouse on but still remove her jeans and panties. I asked her if she was cool with me taking all my clothes off. She said that was fine, and we both climbed into bed. I wrapped my arms around her to try to warm her up.

"I want to play with Lola," she said.

I helped her get the toy out of the packaging and load it with batteries. She took it from me and began to masturbate with it. She seemed to enjoy herself, but I couldn't tell whether she actually came or not. Either way, after a while, she turned off Lola and climbed out of bed.

"I should get home." She began collecting her clothes and getting dressed.

"Okay." I was thoroughly confused at this point. I had a dozen questions at least, but didn't know where to begin. I got dressed as well, and drove her home.

A week later she told me that she didn't realize that I would want to have sex with her every time we got together.

"Well, no, actually, I was really only thinking that we would have sex every time you asked me to take you to a sex-toy shop, or maybe every time you climbed into my bed to masturbate," is the thought that ran through my head, but I couldn't see any benefit to being a smart-ass with this girl.

"I think you're right," I said. "We shouldn't have sex anymore."