Ask Me Anything

When I was a kid my best friend was Becky, who lived in my neighborhood. She is the same age as me, and our parents got to be great friends when we were about 2. We had dinners together, BBQs, and even a yearly trip or two to our lake house. 

Becky was a ton of fun, cute as hell, and kind of a tomboy. She wasn’t afraid to mix it up with the boys, and was an excellent soccer player and gymnast. As we got older, and hit puberty, I have to admit I found her extremely attractive, but we really were just friends. We would horseplay in the pool, and I would feel her budding boobs against me as we wrestled, giving me boners. But we kept it cool, and just stayed friends. 

When we hit 16 we both started dating, and she was always curious about how my dates went, did I get a goodnight kiss, stuff like that. And I quizzed her about her dates too. But Becks didn’t take shit from any guy. She would make out a bit, but if her date went too far she stopped him cold, and more than once she punched or slapped someone who got too handsy. She could take care of herself. And secretly, I was happy she wasn’t doing stuff with other guys. 

One day after school when we were juniors in high school, we were hanging out at her house. Our parents all worked, and so we usually had 2 or 3 hours by ourselves, and we would swim, ride bikes, or watch TV. But mostly we talked. A lot. One day she asked me, “Do you want to play a game?” I said, “Sure”. She said, “It’s called Ask Me Anything. Here are the rules. You can ask me anything you want and I have to either answer it truthfully, or I can decide to not answer it. We promise we won't lie. And we take turns - one question at a time. Got it?” 

This actually made me a bit nervous, but I said, “OK, I’ll try it.” I really wasn’t sure where this was going. There were things I would be way too embarrassed to talk about. But, the out was, I could just not answer the question. “Great,” she said. “I’ll go first.” She looked at me and said, “How far have you gotten with a girl?” I had only had a couple of girlfriends, and they were pretty tame relationships. I said, “With Cindy I touched her tits, and with Marlene she let me rub her pussy through her pants. But that’s it”.“My turn. Tell me what it’s like to have a period.” Becks smiled - it was very personal, but not really sexy - and said, “It totally sucks. First, I sometimes get cramps the day before. And I’ll start getting blood with zero warning. So you have to be ready. And tampons really are a pain in the ass. They get soaked, and you have to change them all the time. It’s awful, really. Remember when I had to leave English all the sudden last month? I almost made a huge mess and just barely caught it.”She wasn’t embarrassed at all by this revelation, which kind of relaxed me. 

Now she asked, “What’s it like to have an erection?” I could feel my face get red. This raised the bar! “Well, it’s kind of exciting. If I see something in a movie like a sex scene or a really hot girl, I can feel it getting hard. And sometimes I have to adjust my pants so it has room to grow. And it gets really sensitive, like it wants to be touched.” I left out that sometimes I had to jerk off. My cock was already getting hard just talking about this, and I squirmed a bit to make room in my pants! Becky sensed this, and gave my crotch a quick glance. 

My turn. There was one question that I had always wondered about, and I had to ask it because there was a rumor about it. I asked, “At the party last year at Dave’s house, when you were making out with Teddy, he said you grabbed his dick. Is that true?” Becky was horrified. “Oh my god, no fucking way! He said that? I’m going to kill that prick! The asshole took my hand and put it on his dick over his pants, and it grossed me out so I left.” I could see that really pissed her off. She was fuming, so it took a minute for her to calm down. 

Becky’s next question took things to another level. She looked me in the eyes and said, “Do you mastubate?” She kind of smiled, like she knew it was putting me on the spot. I felt my face turn red. “Uh, sure, sometimes. I think all guys do” Now my cock was throbbing.  “How often?” she said. “Hey, that’s two questions in a row!’ I objected. She laughed and said, “OK, it's your turn”. 

Not wanting to be outdone, I asked the same question, but in a different way. Instead of asking if she masturbated, I cut to the chase, “How often do you masturbate?” Now her face got a bit red. I could tell she was mulling it over, and she could decline to answer it. But after a few seconds she said, a bit sheepishly, “Every morning, almost. And sometimes at night.” Now her face lit up bright red, she put her hands over her face and she giggled. 

Now my cock was almost painfully hard. It was straining against my pants in a bad way, so I adjusted them which Becky noticed, and kind of chuckled. I felt my face turn red again. Now Becky said, “I was going to ask you if you had an erection, but I’m not going to because I can see you do! Instead, I’m going to ask, do you ever think of me when you jerk off?” 

Oh, fuck. If I say no, I would be lying and she might take offense. Because I always thought of Becky when I jerked off. If I declined to answer, that’s the same as a yes. I almost lied, but didn’t. So, I said softly, “Yeah. I think of you all the time.” There, it was out there. My heart was pounding in my chest because I was afraid of what that might do to our friendship. 

Becky looked at me intently for like 10 seconds, which made me squirm. I started to apologize, “Becky, I’m sor…” and she put her finger to my lips and said, “Shhhh. I think it’s sweet,” and smiled at me. She said, “Your turn! What are you going to ask me?” Now I had a problem. If I asked her if she thought about me when she masturbated, and she said no, I would be crushed. It means she was probably thinking of that asshole jock Jeremy that she had a crush on a few months back. But I had to know, so I said, “Do you think about me, when, you know?” Becky said, “Never!” which shocked me, and she laughed and said softly, “Just kidding. Yeah, I think about you all the time too.” 

With that, she leaned over and kissed me on the lips softly. I kissed her back and I was totally feeling dizzy. We kissed for a few seconds, and she pulled back and smiled. Becky said, “My turn! Have you ever seen a girl totally naked?” “Nope. Closest I got was seeing Cindy’s tits.” My turn. “Have you seen a guy naked? I mean a grown man, not a kid?”  “Yes. I saw my dad a few times when he got out of the shower, and that time at the swimming party when Mike, Dave and Robbie went skinny dipping. But that’s it.”

Now, this was a few years before the internet, so I hadn’t been exposed to porn. Guys talked about clits, and the way they described them I thought of a pussy as kind of a hole between the girl’s legs, and the clit was a bump right above like on her mound or something. And I really wanted to know.  “OK, so what’s a clit like?” I asked. Becky smiled and chuckled softly.  “OMG, it’s so amazing. Mine gets hard like a marble when I get excited. If I don’t touch it, it throbs. And that’s when I have to masturbate.” 

My cock was pounding in my pants, and my mouth was dry. This was the hottest conversation I’d ever had, and I was having a tough time controlling myself. Becky looked me in the eyes. “If you promise not to tell anyone I’ll show you my clit, if you want me to.I nodded yes. Becky slipped off her jeans, then her panties. Her pussy was covered in light brown hair, and a pretty slit with puffy lips was between her legs. It wasn’t what I expected. She scootched back on the bed, propped herself up with a pillow and pulled her knees up and spread them out. She pulled her top and bra off, and was totally naked, and seemed completely comfortable. She then reached down with her fingers and opened her lips, and pointed with a finger to where her clit was. “Right there,” she said. And there it was. It did look like a marble under her skin. And her vagina was glistening with moisture. “Oh god, Becks. You are so beautiful,” I croaked out. 

She said, “Here, give me your hand.” She took my hand, and put my fingertips on her clit. I gently rubbed it, feeling the hard little ball under her skin. She gasped and I pulled my hand away abruptly, surprised and thinking it hurt or something. “Don’t stop!” she said.  With that commandment, I lay down beside her in the bed, and resumed my exploration of her pussy. I slid a finger into her pussy, and she moaned. It was soaking wet and slippery. I resumed paying attention to her clit, and began to circle it slowly, then over the top of it. She gasped and moaned, and said, “A little faster!”. I rubbed her clit more firmly and faster, and she began to move her hips to my fingering and was panting and groaning. After a minute she let out a low moan and her whole body shuddered as she convulsed in an orgasm that surprised me in its ferocity. “Don’t stop!” she croaked, and I kept going until about a minute in she said, “Stop! Stop!” and rolled to her side and began to laugh. Her skin was mottled red and she had beads of sweat on her beautiful breasts. “Holy shit, that was fantastic, Mikey!” She lay beside me naked, and smiling. “Your turn. Take these off,” and grabbed my pants. I stood up and slid my jeans off. My briefs were tented with my rock-hard cock, and there was a growing wet spot from my oozing precum. “Oh my god,” Becky said, and laughed and ran her fingers over my cock through the white cotton fabric, making it pulse. 

With that I slid my briefs off, and my cock sprung out and bobbed in the air. I looked down and it was throbbing to my heartbeat. “Holy shit, that’s big!” Becky said. In all actuality, I’m pretty normal, but that felt good to hear. Becky slid over and sat on the side of the bed, my cock pointing right at her chest. She gently reached out and touched my cock with her fingertips. “Oh my god, it’s purple,” Becky said, commenting on the tip of my cock. A long stream of precum was dripping out of me, and she dabbed her fingers in it, testing it. “Is that cum? It’s so slippery!”  “No, it’s called precum. It’s what happens when I get hard and it just comes out.” She grabbed my shaft and kind of milked more precum onto her fingers, and rubbed it around my tip. I groaned.   “How do I, you know, make you cum?” I took her hand and wrapped it around my shaft and guided her to do a few strokes to show her what to do. She began to stroke me by herself, and she gathered some precum which was almost drizzling out of my cock now to lubricate her hand. It didn’t take long - maybe 15 strokes and I felt my knees go weak, and I came, and came hard. Cum shot out of my cock and onto her tits in four or five spurts. “Oh my god,” was all Becky could say, and she chuckled softly as the cum covered her chest and belly. 

She kept stroking, and now that I was spent I touched her hand to tell her to stop. It was way too sensitive for her to keep going. I looked down, and she was smiling, her tits absolutely covered in my semen and it was rolling down her belly. She took her fingers and dabbed it into the cum, playing with it. She smelled it. (No, she didn’t taste it, at least not then.)  She had a box of tissues on the nightstand, and took out several and wiped up my cum, soaking the tissues. She threw them in the trash and lay back down on the bed, looking at me and smiling. We both knew our relationship was very different now, and it was both exciting and a bit scary. My mind was racing, to be honest.  She patted the bed next to her, and I pulled my shirt off and lay beside her. We kissed softly, and I pulled her against me. We lay like that for a long time, kissing and touching each other’s bodies. I kissed her beautiful tits, and sucked on her nipples, making her groan with pleasure. 

My cock never got soft (to be a teenager again!) and was pressing into her belly between us. I squeezed her bottom, and slid my fingers down to her pussy from behind, which was slippery. My finger found her opening, and I slid it in, then two fingers. Her breathing was shallow and she was shaking. I could tell she was close to cumming again. I rolled her over on her back, and began to finger her pussy deeply, and she spread her legs to accommodate me. I found her clit, and rubbed, and within a minute she came again, this time not so violently, but instead it was like waves of pleasure were moving through her. I slowed as her orgasm subsided, leaving my hand covering her pussy. We began to make out again, and Becky fondled my cock gently, tugging on it a bit, then softly fingering it. She took her thumb and ran it around the head, and I gasped. It had almost too much sensitivity. 

We lay together for a long time. We kissed, fondled, explored. I kissed her face, and stroked her hair. I kissed and sucked on her nipples. We fondled each other’s genitals softly, and I got hard again, but didn’t cum. Becky did cum a third time though, and this orgasm was especially sweet as we kissed and our bodies pressed against each other and we both shared her pleasure. Finally she said, “My mom will be home soon. We better get put back together!” We jumped up, got dressed and went downstairs. I was all the sudden terrified of her mom coming home. She treated me like her son, and I thought she would just somehow know what we did. So I said, “I think I should go home.” We kissed for like maybe five minutes standing there, neither of us wanting this moment to end. Finally, I broke it off and said, “Bye! I'll be here at 7:30 and we can walk to school,” and she nodded her approval, and I slipped out the back door. 

I got home and ran upstairs and lay on my bed, thinking about what had just happened, and how everything was different now. I smelled my hand, which was fragrant with her sweet scent, and stuck a finger in my mouth. She tasted delicious, like nothing I’d ever tasted before. I fantasized about licking that beautiful pussy, and couldn’t wait to do that in reality. Later that evening at dinner my mom said, “Honey, you sure are quiet tonight. Anything wrong?” I smiled, and said, “No, not at all. Everything’s great, actually,” and I smiled at her. She just kind of smirked, like she had a feeling or something. But didn’t ask me any questions. I watched some TV, but couldn’t concentrate on anything. I said goodnight, and went to bed. I lay there for a long time, thinking about what had just happened, and finally fell asleep. I dreamed of Becky, kissing her, holding her lovely body, and entering her. I woke up in the middle of the night with a huge erection, and stroked one off quickly so I could fall back asleep. 

And that was the beginning of my new relationship with Becky.