My first time happened slowly, but it is a great memory.
My first teen crush was for a girl named Cyndi. I remember thinking she had a cool way of spelling her name. Anyway, I had just turned sixteen and she was fifteen and we were both still virgins and pretty sexually inexperienced. Our dating started slowly, after a couple of months we'd only french-kissed and held hands. That all ended very quickly. The first day of summer (school had ended the day before) my sophomore class had an 'end of school' beach party at the lake. Cyndi and I looked forward to it, I brought her to the mall and we both bought swimsuits. I so much wanted her to model it, but guess we were both too shy. I had a hard-on for a week looking forward to that beach party.
At the mall store, Cyndi bought a two-piece bikini, red and white, and I bought some flowered beach trunks, I didn't even try them on. The day of the beach party, I picked her up at her house, she was dressed in shorts and t-shirt, but I could see the strings of the bikini through the t-shirt. We got to the beach and lots of kids were already there, mostly all already in the water and on the picnic tables. I could hardly breathe as I waited for Cyndi's unveiling. I quickly shed my t-shirt and said, 'Come on.' I then remembered Cyndi had never seen me without my shirt and she stared, smiled and quickly shed her clothes. She had a killer body, I could see the outline of her tits through the bikini top. When we got to the water, I could see them even better. We played rather innocently in the water. I had a hard-on that I hid in the water. We hugged and kissed, her arm gently touching the tip of my penis, the head straining in my swim trunks. I think it was an accident, because she pulled back fast, but it was amazing. I remember when I got home, I went straight to my shower and jacked off, imagining it was Cyndi who was doing it.
A couple of days later, I was home mowing the lawn and Cyndi came over, sporting her new driver's permit. Her mother let her stay over, and we went inside and watched TV. I was still sweaty, so I took a quick shower and put on a pair of sweat shorts and came back in. Cyndi and I kissed good-bye, hearing her mother honking outside, and I got another instant hard-on. Cyndi's boobs were pressed on my bare chest, she then brought her hand down and lightly rubbed my hard penis. She didn't take it in her hand but rubbed it up and down through my sweats. Her mom honked again and she ran out.
From that day on, whenever we were alone, I wore sweat shorts or sweat pants without underwear. Over the next few weeks, Cyndi continued to rub my hard-on a little whenever we would make out. She would take off her bra and let me rub her tits through her shirt or t-shirt. This went on for the whole summer. Once, Cyndi let me go up her shirt, and I briefly touched her nipple. She never would keep rubbing me till I came, but even the light rubbing was fun.
In the fall, it must have been right after school started back, Cyndi and I had a date that ended up at my house. I was surprised to see my mom gone, she was rarely far from home but she left me a note saying she would be home in a couple of hours. Cyndi and I ended up on the couch, but we were both sweaty from being at the park. I boldly (I still wonder how I got up the courage) said I was taking a shower and did she want to take one too. We only had one bathroom, and Cyndi's response was, 'I'll wait till you finish.' I told her there was room for two. Cyndi agreed if we both left on our underwear. I was too eager to agree. We went into the bath, it was pretty dark as it didn't have a window. Cyndi wanted to leave the lights off, so I left the door open just a crack. We disrobed, I left on my boxers, but already had an erection. I hid it by holding a towel in front of me. Cyndi took off only her t-shirt, choosing to leave on her bra and jean shorts. We started the water and got in. We took turns washing ourselves. We eventually went to kissing. She allowed me to unhook her bra and it fell into the shower. I had her back against the shower wall and let my dick grind into her shorts. I know she could feel me.
We finished, dried off and I took off my boxers and put a towel around myself. I wanted Cyndi to watch, but she turned around the other way. I went into my bedroom to change, and Cyndi followed. I found her a clean t-shirt of mine to put on. She put it on and sat on my bed. I then took my boxers out of my drawer, Cyndi was still watching me and I went over to my closet and took out a shirt, she was still watching. I went back over to the bed on the side she wasn't on and grabbed my boxers, she turned around to watch. Did she want to see me naked? Maybe it would lead to me seeing her naked!
I hesitated for a second and let my towel drop, I tried to do it like I normally did, my erection had mostly subsided but before I could even put my underwear on, it was getting hard again. Cyndi said, 'Wow.' That caused me to stop. She then said, 'Does it get hard that fast?' I meekly said, 'Sometimes.' I then let my boxers drop to the floor and let her watch, why not?
Cyndi then stood up and started asking questions almost like a doctor, 'How big is it usually?' 'Does it hurt to get hard?' 'Do all guys have that much hair around it?'
I wasn't particularly hairy, and answered her questions. Cyndi then asked me about semen and how it came out. Over the next few minutes, I sat down on my bed naked and explained the limited knowledge I had. She then asked me to let her see sperm. 'How do you jack-off?'
I showed her by yanking it a few times, then stopped. 'No, I want to see it all the way.' I was kind of embarrassed and excited at the same time. I started pumping it the way I usually did, wanting so much for her to be doing it. I kept pumping and told her when I was about to cum. Cyndi's eyes got so big when I began spurting out all over my chest and pubic hair. She kept watching. About then, I could hear my mom in the house. We were dead! There was no time to do anything. I froze. Cyndi was fully dressed and began going towards the door. I had no time to do anything and my mom walked in. There I was with the spunk all over me, my mom screamed and ran out. (My mom hadn't seen me naked since I was a toddler, I'm sure.)
Cyndi left, mom calmed down. She would never allow me to have a girl over again. I told her Cyndi hadn't touched me, that she'd only watched me jack off, which was true. It didn't matter. Cyndi and I advanced sexually from there. She became my first, we were involved in mutual masturbation for a couple of months and then moved on to a full sexual relationship. We dated till I graduated. Mom got better, even supplied me condoms after she realised Cyndi and I were sexually active. We finally broke up. What a great memory.