How an Older Guy Taught Me How to Masturbate

One time was especially rough because my life and body were changing a lot but I had a few friends and what’s worse is I didn’t have any adults I could look up to. The closest thing was my neighbor Alex. This particular time he was 16 and I was a bit younger. Our parents were close so I would sometimes go to his house if my parents weren’t home from work yet. He helped me with homework on occasion. He probably saw me like a younger sister but I had a crush on him for so long. He seemed so wise to me at the time, always giving good advice. Most of his friends were girls and I can see why because he had a way of just making you feel comfortable and safe.  We lived in the southeast US so sex ed just covered the basics and didn’t get into the psychology of it at all. And I was feeling warm in the face and tingly between my legs a lot. I needed someone to talk to about it.

I never really considered having this kind of conversation with Alex because I didn’t really think of him as a sexual person until one day we decided to go swimming before my parents got home. It was spring and I hadn't swam all winter so I had outgrown my only bathing suit a little. It was tight and uncomfortable and didn't cover much but I trusted Alex so it was okay.  Alex was wearing only basketball shorts. It was the first time I had ever seen him without a shirt and he had decent muscles. We did cannonballs and had a contest to see who could hold our breath the longest and raced across the pool for about 45 minutes. The whole time he stared up and down my body and was only half listening when I talked.  When we got out and sat on the deck to dry off we faced each other to talk and he was staring at my crotch the whole time. I could feel a front wedgie and when I looked down I saw some of the short little pubic hairs I was starting to grow were exposed. I spread my legs a little more to see what would happen and he just kept staring with wide eyes.  It occurred to me that Alex being older with his plethora of female friends might be a good person to learn about sex from. So I just blurted out, “Have you ever had sex?”

“No, I haven’t.”

“Really? All those girls you’re friends with?”

“I’ve dated a few of them, we just never got that far.”

Looking back, I’m happy he didn’t give that ‘nice guy’ bullshit. The only girls who go after douchebags are douchy girls. Lower your standards physically. Anyway I asked, “What age do you think is too young to have sex?”

“Honestly, probably college age.” The south for ya.

“Really? You’re a guy, you must want relief, right?”

“Yeah, but it’s safer to wait for the right person.”

Snore.  I knew a little about masturbation and at the time was under the impression that it was an activity predominantly enjoyed by men. Probably because of the notion that “ladies don’t do that.” Again, the south for ya. So I asked him if he masturbates and he said yes.  “Do you watch porn or do you think about girls you know?”

“Both.”

I asked, “You think it’s normal for girls to masturbate?”

“It’s different for girls but yeah.”

“How so?”

He says, “What turns girls on isn’t always a physical quality. Sometimes a personality trait or a particular action gets the gears going.” He was right.

“What else do you know about how girls masturbate?”

“I don’t really feel comfortable talking about this with you.”

“I don’t mind.” I really didn’t. “If you’re worried about getting in trouble I promise I won’t tell our parents. I don’t really have anyone I can talk to about this.”

“Fine,” he said. “I know the clit, the top part of the vagina, has the most nerve endings so rubbing it is supposed to feel really good.” I didn’t know that. Right then and there I started rubbing it over my bikini and it did feel pretty good. Kinda tickled and made the whole surrounding area feel tingly. I looked up after a couple seconds to see Alex staring with his eyes super wide. “I’m so sorry,” he said.

“Why?”

“I don’t want you to think I’m taking advantage of you.”

“That’s totally okay.”

“No it’s not. Be careful around guys, especially older guys.”

“I don’t think I need to be worried. Are you gonna do anything?”

“No but not everyone’s like me. Be careful.”

“I trust you. Is this turning you on? Because that’s okay too. It’s alright with me if you want to think about this while you’re masturbating later.” He was silent. “What else do you know about how girls masturbate?”

“Um, there’s a g spot. I don’t know much about how that works but I think you gotta just find it randomly by…uh…experimenting I guess.”

“Is it near the clit?”

“No, it’ll be, you know, inside.”

“I don’t understand.”

“You gotta use your fingers.”

“Oh to like, pretend my fingers are a dick?”

“Yeah pretty much.”  I brushed my fingers across my lips over my suit. Again it tickled and sent tingles all throughout that region of my body. I could feel some muscles getting tense. I looked over to Alex and could see his dick clearly outlined by his shorts. “Do you think I’m attractive?” At the time I was about 5 feet, probably ~100 pounds, round face, soft lips, brown hair, typical white girl. My boobs started coming in a couple years before but were probably still A cups at this point.

“This is so inappropriate,” he said.

“Because I think you’re really handsome.”

“Well, thank you. Yes, you’re very pretty.” I felt a wave of heat start in my pussy, go up my back and down my arms when he said that.  I finally asked him what I’d been dying to the whole conversation. “Can I watch you masturbate?”

“What? No!”

“Please? I promise I won’t tell anyone else. Didn’t you have an older brother or something to learn this stuff from?”

“No, I kinda just figured it out on my own. In fact, I still am.”

“Don’t you wish you had someone to show you then?” He paused. “Please, I want to know what to expect and from someone I trust.”

“Fine,” he finally said and pulled out what at the time seemed like a massive dick. It extended to about two inches below his belly button. His pubic hair was really bushy and his balls looked really small proportionally. I figured I would help and took my top off. Before he started I asked if he wanted to touch my boobs. He reached over and ran his thumb across them as they were still too small to squeeze. It tickled all the way down my arms when he went over my nipples.Then he leaned back in his chair. I was expecting him to make a fist and go all the way up and down his shaft but he only pinched the top and made circles. Then he asked me to take my bottoms off. This part is always exhilarating for me because this region is the least hygienic so having it uncovered adds an element of dirtiness to it. No one had ever seen this region of my body before so the first time was especially exhilarating. My pussy lips were usually like vacuum sealed but at that moment they were looser than they had ever been before. A little bit of white fluid started dripping out which had never happened before as far as I knew. “You’re supposed to ejaculate, right?”

“Yeah.” He was still jerking.

“What usually happens there?”

“I usually just shoot it onto my stomach then wipe it up.”

I had barely had semen described to me in class so out of curiosity I blurted out, “Want to shoot it onto me?”  He got up, stood over me and shot a huge load onto my A cups and a little into my hair. I scooped up some and played with it.

“Okay, my turn,” I said. I ran a finger slowly across my clit, then after a couple minutes of not getting anywhere I shoved a finger inside myself. It was too small to accomplish anything so I asked Alex what he thinks I’m doing wrong. He said I need to rub my clit faster and harder and to use two fingers inside. He said it should probably hurt a little. I asked him if he wants to show me, then he leaned in and reached out.  He waved his whole hand but only his middle finger actually made contact with my clit. It occurred to me several years later that’s because the wrist is more agile than the finger joints. He gradually got more intense and it started to hurt after a while. He then stood behind me and stuck only his middle finger up my vagina and it filled me up. He moved his finger in and out very quickly and this time is did hurt but it was more of a good pain, like cracking your knuckles or peeing after holding it for a while.  After about 6-7 minutes of that a huge tingling sensation spread throughout my body. I asked Alex what that was and he said it was an orgasm, the same thing he experiences when he ejaculates.  We had about 45 minutes until either of our parents were going to be home so we showered quickly. He apologized but it was okay, I wanted it too and I didn’t feel taken advantage of at all. I didn’t mind giving him something to think about because I knew he would never actually do anything I wasn’t okay with. I was smart enough to know what I was getting myself into. I knew what I wanted.

After dinner that night I played with my clit some more trying to get the right speed and intensity to find the sweet spot between pleasure and pain, and tried to fingers in my pussy. My fingers were still pretty thin but curling them helped a lot. I found my g spot a couple days later. Alex and I never fooled around again but we remained friends. I check up on him recently and his wife is very petite. I must have done a number on him.