Masturbating with Amy, Chapter One

Masturbating with Amy, Chapter One

Amy and I had known each other for several years and had never been particularly close, but were always friendly. We became friends when we both ran cross country as freshmen in high school. We were in some of the same classes and had similar interests, but mostly our personalities just clicked. Amy and I were both quiet, not especially popular, and were average looking.

One day after practice I asked her if she’d like to go running on the weekend, just the two of us, and she said yes. We only lived about half a mile apart so it was nothing to walk, run or ride my bike to her house. This continued throughout the fall and into winter, when we started running together several times a week since the season had ended. We fell into a routine of running, then cooling down while watching TV on the couch in her basement. We chatted and became very comfortable together, almost like brother and sister. Amy’s parents knew there was nothing but friendship between us, so they left us alone when we were together.

On one Sunday, her parents were gone and we went down to the basement after running. We were watching TV as usual, and she quietly said, “can I ask you a question?”

“Sure”, I replied.

“It’s personal, and you can’t tell anyone that I asked you this.”

“Of course”, I said.

“I’m absolutely serious, I need to know that you’ll keep this just between us. It’s embarrassing.” She added.

I tried to reassure her. “Whatever it is, I won’t tell anyone. I’d never do that to you, and I know you wouldn’t to me. We’re friends, and I don’t want to hurt that. Is everything ok?”

“Thanks, I’m fine, I’ve just wanted to ask something, maybe several somethings, for a while now.” She paused, and I waited for her question, which finally came. “How much experience do you have?”

“You mean, like, sex?”

“Yes, experience with a girl, or a boy also, I guess.”

I hadn’t expected her question to be about sex. I was nervous, but also excited. I had butterflies in my stomach and got a little dizzy, and my cock pulsed once. I didn’t want to answer her, since it was embarrassing for me, but she’d been brave in asking so I owed her the truth: “I don’t have much experience at all. I’ve kissed two girls, only one with tongue, and also felt one of her boobs through her shirt. That’s it.” I looked down, knowing that most boys my age had done much more, at least feeling a girl up under her shirt, if not seeing boobs, pussy, feeling a girl’s pussy, or having outright sex. This lack of experience is what made it hard for me to even get started with girls.

Amy didn’t laugh at me, instead she looked more comfortable having heard my answer. “I’m almost exactly the same. I’ve kissed 3 guys, two somewhat passionately, and both felt my boobs. I went on one date with one guy and three dates with the other.”

“Why did you stop dating the second guy?” I asked.

“It was last year. We’d been kissing for a while, he’d been playing with my boobs, and tried to push his hand inside my shorts. I wasn’t ready for this, and he backed off, but then he tried again and I pushed him away again. He took me home right away and never called again.” She paused for a few seconds. “I cried a lot for a while after that.”

My dick started to get hard at the thought of a guy fondling her boobs and trying to get in her pants. I felt bad though, and could tell this was hard for her to admit. “It wasn’t your fault that he didn’t ask you out again. You were right to push him away if you didn’t want him touching you.”

Amy said, “I know, but otherwise I liked him, and I know he told other boys about it, so now I’m even less popular than I was, which wasn’t a lot to start with. I haven’t had a date since.”

This girl that I’d become good friends with was much more attractive than she realized. “Amy, you’re smart, funny, kind … and beautiful and sexy.” It was hard for me to add that last word – I didn’t know how she’d take it.

She smiled a little. “Thanks, I never feel very pretty or sexy. It’s only in my fantasies that I feel attractive.”

This had been a good conversation so far, becoming much closer to the girl I already felt very comfortable with, but her mention of fantasies perked me up some more, and got my dick a step harder. I wanted to hear more. “What is it about your fantasies that makes you feel more attractive?”

“In my fantasies I’m with a guy who really wants me, and as we’re making out he explores me, enjoying what he’s seeing and feeling.” She paused again. “It gets me excited.”

She didn’t seem shy or embarrassed talking about this, so I decided to tease a little.