The first time I ever got off from someone else was at an animé convention back in 2002.
There was a bunch of us who had gotten a hotel room. Actually, someone's older brother got it for us, but most of us were about 14-16. There was this really pretty girl named Sheila with red hair and deep green eyes who went to a different school than I did, but we all hung out in the same places afterwards.
Well, someone got a hold of some Hentai and was showing it on his portable DVD player in the hotel room. Hentai is like animé porn, but it was really gross and I wasn't turned on at all. Sheila was curious about it, and everyone was telling really raunchy jokes, so I hung out because the company was good, but man... yick. There's this one part when an alien with a huge tentacle is fondling this girl while she's paralysed for some reason. I have to admit, it was pretty hot, even for animé, and even though the rest of the movie was just absurdly violent, that scene kept everyone quiet for a few minutes. If anyone went to the bathroom, we would make a big joke that they went there to masturbate.
We watched some other stuff, but Sheila was very flirtatious with me, which I encouraged. She laid in my lap, I played with her hair, and tried very hard not to have a boner because the way Sheila was leaning, I could see right down her shirt. She had a lot of freckles, and I could see they went right down her neckline. I could almost see one of her breasts entirely except for the nipple, and she kept pushing herself into me, asking me to rub her head or arms or something, which I happily obliged.
Around 3am, we decided to crash and so we turned off the lights. There was about eight of us in the room, so I slept on the floor on a sleeping bag. I was woken up by a strange sensation near my head. It was Sheila, and she was trying to undo the lanyard of my bag.
'What are you doing?' I whispered.
'Let me in,' she said softly, and kissed my ear. She didn't have to ask twice.
I undid my lanyard, and she slid into my bag. I could feel all she was wearing was a top and some panties. Her skin was cool and soft. We quietly started to kiss and make out, but she stopped and said, 'Lie down. Just stay still.'
Her hands rubbed my chest, then went down to my stomach. My hard on was pulsing and throbbing and by the time she got down to my sweat pants, she started to push and rub *around* my cock, but didn't actually touch it. She started to suckle on my earlobe and moan softly. I swear, I was so turned on, my face must have been burning red. I yearned for her hands to touch my cock, but she just kept going around it. Her other hand was doing something near my leg. After a little while, my dick started to get sore from the teasing.
'What are you doing?' I finally asked.
'I'm fucking my clit with my hand,' she said. 'You're next.' Her tongue went into my ear, and slowly I felt her small and slender hands slide under my waistband and fumble with the elastic of my underwear for a brief moment before touching me. Her hands felt oddly cool, and against my hot cock, her small hands felt like something wet and slippery. 'That movie made me so hot,' she whispered. 'I felt like I wanted to have a tentacle fuck me like that. A hard, slippery, thick tentacle like this one.'
Her breathing got faster and she started to stroke my fat and swollen dick. I started to feel her breasts through her tee-shirt, and touched her rock-hard nipples. She whispered, 'pinch my nipples... please... pinch them. Play with them... oh god please.'
I didn't last long after that. 'Oh, God, I am gonna come,' I whispered, but didn't finish the word 'come' because my dick exploded and shot wads of cum all over my underwear, her hand, and pretty much everywhere else inside my pants. My whole pelvis pulsed with pleasure numerous times, and it was all I could do not to scream. I had never come so hard or so much in my life, it was like I had poured a pint of cream down my pants.
Just before I relaxed that final pulse, her breathy gasps indicated that she, too, had come. She buried her face into my pillow and let out a muffled 'eep.'
We held onto each other for a few minutes before she said, 'we gotta clean up. Give me your pants and underwear, I'll wash them.' When she came back, she game me a pair of her sweat pants and said I could wear these until mine dried in the bathroom.
That was awesome. We made out a lot during the convention after that, but none of us ever came. Sadly, the whole girlfriend thing didn't work out for her, and she ended up hooking up with someone else a year later. I didn't have another girlfriend until college, and that was the first time I had sex, but that's another story.
Sometimes when I jack off, I think of Sheila. Her broad smile, her deep green eyes, her fire orange hair, pale skin, and freckles. I thought of how she pleaded with me to play with her nipples just before we came, and her whole body tensed and contorted. It was like we both were surprised at how good it felt.
I hope to share that experience again.