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. “Hmm, what happens when you get excited?”

She smiled, knowing exactly what I was going for. “You can probably guess what happens – I masturbate. I assume it’s the same for you when you get excited?”

Well, it was out in the open now! “Yeah, I do. I’ve never really known about girls masturbating. I think it’s well known that guys masturbate. A lot, I guess. But no one talks about girls masturbating. Will you tell me how often?”

“Most days, sometimes in the morning, sometimes at night, sometimes both if it’s on my mind,” she replied.

My cock was extremely hard now. “What gets you going?” I pressed.

“I don’t know exactly, I don’t think it’s anything in particular. I’ll just rub myself a little, casually, and most times it’ll get me going and I’ll masturbate until I come.”

I couldn’t believe how much she was sharing, and how casually now. I was genuinely curious about this subject, but also was extremely turned on. “Do you think about anything in particular while you’re masturbating?”

“Just being touched, kissed, explored. I think about my hands being a guy’s hands, touching me, rubbing me, probing me.”

Whoa, I liked probing. “Probing, as in …?”

She giggled. “Yeah, pushing a finger inside myself. Do you like hearing that?”

I tried to laugh, but was afraid I’d been caught. “Yeah, I guess I do. It’s really exciting to hear what a girl does and thinks about.” I paused. “I never expected this conversation to happen.”

She giggled again. “I’d wanted to talk to you about this for a while, but hadn’t had the guts. Now you know why I swore you to secrecy. So I told you a lot about me, it’s your turn to answer questions. How often do you masturbate? What do you think about?”

I figured this was coming, and it was only fair that I give her honest answers. “I probably average twice a day, also morning and night, sometimes after school. I think about the usual stuff I guess, girls’ boobs, girls’ pussies, what it’d be like to see a girl naked and touch her, have her touch me. What it’d feel like to have sex.”

She asked, “Do you think about anything particular when you come? I most often think about what it’d be like to have a tongue licking me, licking my clit, and then I explode.”

Whoa, I couldn’t believe she just shared that! I felt now like I could tell her anything and everything. “I start stroking my cock faster and squeezing it tighter, thinking about slamming in and out of a girl’s pussy.”

“Typical guy, thinking about pounding a girl hard!” she said. I didn’t know how to respond, and she went on. “I’m just teasing, I expect it’s only natural for guys to fantasize about fucking a girl. I want to know what it’s like, too. I was embarrassed to say it before, but sometimes I’ll slide a finger in and out of my pussy fast, sometimes two fingers, trying to know the same thing: what it’s like to fuck.”

God, I loved hearing her say “pussy”, “clit” and “fuck”. She’d sworn around me before, but had never said anything about sex or body parts. I had been shifting around a little during our discussion, trying to hide my erection, which was now absolutely full.

“Are you excited now?” Amy asked. “Is your dick hard?”

Again, I couldn’t avoid the question and didn’t want to lie. All cards were definitely on the table at this point. Plus, she likely noticed my squirming. “Yeah, my dick is hard. Impossible not to be, with what we’ve been talking about.”

“Me too. Excited, I mean. If I was alone I’d definitely be masturbating right now and would probably come very quickly.”

I smiled a little, embarrassed to answer, but reassured that she was feeling the same thing. “Me too, I’d be all over myself, and it would only take seconds.”

She laughed, breaking the tension a little. There were blankets on the back of the couch, and she threw me one. “Go sit down at that end and you can put the blanket over you and I’ll do the same with this blanket down here.”

She did what she said, grabbing the second blanket, scooting to her end of the couch and sitting on the couch facing me with her legs on the couch. She threw the blanket over her legs, up over her waist. I couldn’t see anything from her stomach down to her calves now. I followed suit, moving to my end, sitting fully on the couch, with the blanket covering me in the same way. Our feet touched, and a shock went through my system, down my spine, and my cock twitched. It was somehow erotic for just our feet to touch in this way.

I liked that now she couldn’t see my hard on, but didn’t know what to expect would come next. She seemed to have a plan, though. “I have my hand pressed against my pussy,” she said.

That was incredible to hear – she was at least partially touching herself right in front of me! I didn’t say anything, so she continued, “I’m pushing against my whole pussy with my hand, pressing and releasing.”

She was now actively masturbating, even if it was just the early stages, and I was getting a play-by-play! I knew I needed to say something to keep this going, and it was only fair to reciprocate, even if just to make her feel like we were in this together. Plus, my cock was begging for some contact.

“I’m doing the same thing, pushing my hand against the underside of my cock. It was desperately needing to be touched.”

She smiled. “I’m glad to hear you were feeling the same way. Are you embarrassed to be doing this with me? In front of me?”

“Yeah, sort of, but it’s the same for you, so we’re in it together.” I paused again. “I love thinking about what you’re doing under your blanket.”

She smiled again, clearly more comfortable with this than I was. “I’m so excited right now, I love knowing what’s going on under your blanket, too. Please keep telling me what you’re doing and I’ll do the same. I’m now sawing my hand up and down across my pussy. My clit feels fantastic.”

I wasn’t rubbing myself too hard at this point – how could I? Knowing that she was masturbating just a few feet from me, talking about how good her clit was feeling, I was afraid I’d come immediately if I did anything too forceful with my cock.

“That’s amazing, I love hearing you talk about your clit. I can barely touch myself for fear of coming. I’m not sure my dick has ever been this hard.”

“I know,” she said, “I don’t know if I’ve ever been this aroused. Do you want to stay like this for a while, or keep going?”

Oh my God, I had to keep from blurting out “More! More! More!”, but instead I said, “Let’s keep going. You’re braver than I am about describing things, but I want to hear more, and I’ll tell you more.”

“Ok,” Amy said, “time to step it up then.” I think she was genuinely excited that I wanted to keep going. I saw her upper arm move and knew something different was happening under her blanket. “I just slid my hand inside my shorts, just over my panties. I’m rubbing my fingers in a circle on my clit. I’m serious about masturbating to orgasm when I get to this point.”

Whoa, now I was pretty sure that we weren’t just having some fun, sharing secrets, and becoming more intimate. Amy intended to masturbate in front of me, all the way to coming. I was nervous and excited, knowing that she probably expected me to masturbate for her. Of course my cock really wanted it, but I was embarrassed to actively start jacking off in front of her, even if she couldn’t see anything. Time for me to step up, though. I untied my shorts, pulled them away from my stomach, and put my hand inside, wrapping it around the top half of my cock.

“I have my hand inside my shorts now, holding and squeezing the top half of my cock.” I wanted to confirm where this was going. “Do you want to keep going until we come?”

I was glad to hear her confirm what I was thinking and wanting. “Yes, I don’t think I could stop now if I wanted to. My pussy’s on fire, begging to be rubbed hard. I could come in less than a minute at this point.”

“What would you do right now if you were alone?” I asked.

“I’d have my hand inside my panties, slide a finger in and out of my pussy a few times, then rub my clit hard until I came.”

Her breathing was faster, and I had a hard time with my next statement: “You can do that right now. I’d like to see you come.”

“I want you to see me come. I’m so damn horny right now, I’m not embarrassed at all. I just need to come so badly. Please don’t come though, I want to watch you after I’m done.”

That seemed more than fair. “Ok, go ahead, I won’t go any further with myself. You’re so beautiful and so sexy, Amy. I really want to see you have an orgasm. Go ahead and relieve yourself. Enjoy it.”

“Oh God, thank you, I’m getting closer just hearing that. I have a finger in my pussy now, sliding in and out, now fast, wishing it were a cock.” I couldn’t believe I was hearing and seeing this. The beautiful Amy, my good friend, was completely aroused, eyes closed, slamming her finger in and out of her pussy in front of me, and was seconds from coming. I just watched quietly, barely touching my cock. I desperately wanted to stroke along with her and come, but held off since I owed her the same show. I could see her arm moving fast now and it was amazing to know exactly what was going on under the blanket.

“My finger’s out of my pussy know, rubbing my clit hard, home stretch now. Ohhh, I’m going to come right in front of you and I don’t care. It feels so good. Here I come!” And with that, she shivered a little, grunted, and her whole body shook a couple of times. She then exhaled deeply and sunk back into the couch, not moving at all, eyes still closed. I didn’t want to say anything. I just let her cool down and be the first to address what just happened.

After a few seconds, she opened her eyes, looked at me, and smiled. “That was amazing,” she said. “I can’t believe I just masturbated right in front of you, but oh my God, it was incredible!”

“That was so beautiful. You’re absolutely gorgeous when you’re aroused and when you’re coming. You’re beautiful all the time, but that was incredible. I love that I’m the only guy who’s seen you that way.”

“I feel so warm right now. That was so exciting to do that in front of you. How are you feeling? How’s your cock doing? Ready to come?” She smiled, obviously knowing the answer.

“Oh yes, it desperately needs relief. I’m going to stroke myself and come now, and won’t be at all embarrassed about it.” With that, I pulled my shorts open again, and my underwear, and took full grasp of my cock, stroking it about medium speed, not gently playing, but not full-on jacking. I remembered that I owed her a similar play-by-play.

“I have my hand around my cock, stroking it, not full speed yet. It feels so good, my cock desperately wants to come. All I can think about is the image of you coming, and how beautiful it must have looked under that blanket with you rubbing yourself hard.”

She smiled and said, “just like it must be beautiful under your blanket right now, seeing you stroking yourself, harder and harder, getting closer and closer. Go ahead and go as fast as you want, I want to see you come.”

Well, at this point I wasn’t going to deny her, and what she wanted was exactly what I wanted. I started stroking full speed, intending to come as quickly as possible. “I’m stroking fast now, it won’t be long, it feels so good. I’m thinking about your pussy, your hand moving fast in your panties, watching you twitch when you came, oh God!” And with that I exploded, my come spurting out hard, hitting the underside of the blanket, splashing back down onto my shirt, multiple spurts, so much relief going through me, thinking about Amy’s pussy and tits and ass all at the same time. Eventually, my come started just dribbling down my cock, and I lay back, panting, completely spent.

“That was incredible,” I said. “Now I know how you feel. No embarrassment, just relief. That was so much fun and so amazing. I’ll do this with you any time. Every day if you want.”

She giggled again. “Fine with me, I’m not going to turn down an amazing orgasm.”

We both were lying back, looking at each other, and started laughing. Amy was the first to throw off her towel, saying “my parents may be home soon, probably best if we got going.”

I had a problem, though. I couldn’t just throw off the blanket since I’d come on it and on myself. “Um, yeah, I agree, but I’ve got a mess under here. I came all over the blanket and my shirt.”

Amy giggled and went upstairs to get me a towel. She handed me the towel and I did my best to clean up after myself, especially the blanket. It was obvious, though, that there had been come on the bottom of my shirt. I kicked the blanket off of me and got up, with Amy laughing when she saw my shirt.

“Looks like you did enjoy yourself!”

I smiled and kind of shrugged my shoulders, not knowing what to say. Amy came up to me and gently kissed me. She whispered in my ear, “thank you for an amazing time. I wanted this to happen but didn’t know if it would, and never expected it to be so incredible. I really do want to do this again, many times.”

Of course I agreed with her, “me too, this was fantastic, I never expected this to happen, never thought it was even a possibility. I’m so glad that it happened and can’t wait for it to happen again.”

We kissed again and headed up the stairs. At the door, we kissed once more, hugged each other tightly, and I headed home.

As I was walking home, I realized I’d just shared something incredibly intimate with someone. A girl I liked a lot, but hadn’t thought much about sexually. Now she was not only my good friend, but my….lover? masturbation buddy? I wasn’t sure what our relationship was, but I wanted to masturbate with her again and again.

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