It was on a class field trip to Washington, DC, at the end of eighth grade, that I had my first encounter with boy/girl sexuality. I had turned 14 a couple months before. We were back at the motel after sight-seeing but before dinner, and all the kids were hanging around the swimming pool. Four of us (two girls, me, and the boy who was my room-mate) decided to go in and watch tv. We went to my room, even though girls weren't supposed to go in boys' rooms, and vice versa. There wasn't anything worth watching on tv (this was before cable), and we decided to play cards. My room-mate, a classmate named Jeff, said 'how about strip poker?' I had played it with other boys a few times, but never with girls. I was amazed at his audacity, and equally amazed when both girls agreed!
We weren't wearing much to start out with-bathing suits (both girls had 2-piece), shirts, and sandals or shoes. We evened up the number of items before we started, and it wasn't long before the 'moment of truth' came. One of the girls (Nancy) had to take off her top, and Jeff and I were drooling at the sight of her small cone-shaped tits. But the first to get naked was Jeff. I wondered if he lost on purpose, because he seemed anxious to show his equipment. I'd seen his cock (and felt it up) once before, so it wasn't a surprise for me to see his mature-looking 6-inch boner and abundant pubic hair when he stood up and pulled down his swim trunks. But both girls were wide-eyed and giggling at the sight. Jeff enjoyed the attention and even stroked it a few times as he was being ogled.
'Can you make the sperm come out?' asked Christine. (We'd had sex-ed that Spring.)
'Yeah,' said Jeff.
'Show us!' said Nancy and Christine together.
I kept my mouth shut, but I wanted to see it too. I'd never seen another boy cum, even though I'd felt up boners with other guys on several occasions.
Jeff's reply was perfect. 'I'll do it, but only if everyone else gets naked and does it too. We'll each pick a card for the order we go in... and everyone gets to feel each other up too. OK?'
The girls agreed. I was a little reluctant to let a girl feel me, but there was no way I was going to miss out on this chance.
Jeff pulled a 2, 3, 4, and 5 cards from the deck and shuffled them up. We each picked, and the order was Nancy, me, Christine, and Jeff last (ironically).
Jeff kept with his role as the instigator and rule-maker, telling Nancy to strip the rest of the way and lay on a bed. She giggled nervously, but let each of us (Christine included) feel her tits, which now had beautifully stiff nipples. Jeff began feeling her pussy, but when he started putting his finger inside her, she objected and pushed his hand away. He told her to finger herself, and she did so, masturbating herself for a minute or so and then stopping.
'It's Bill's turn now,' she said, hopping up off the bed.
I was totally aroused by this time, and could barely breath as I pulled down my bathing suit to reveal my 5-inch erection, adorned with just a fringe of hair. Jeff told me to lay on the bed, and the girls were anxious to give my cock and balls a good feel. (Jeff just watched.) My nervousness completely gave way to lust, and when the girls told me to 'make the sperm come' I had no hesitation about stroking myself off. It didn't take long until my leg muscles stiffened and semen squirted up onto my belly.
As I cleaned up with a wash cloth from the bathroom, Christine took my place on the bed. Her tits weren't very big, but were more pillow-shaped than Nancy's cone-shaped breasts, and I loved being able to touch them and play with the nipples. And I was especially aroused when she spread her legs and let us feel her there. When Jeff tried the same thing that Nancy had denied him, Christine didn't object. Jeff's finger slipped right into her pussy and he stroked it in and out a few times. Then it was my turn and I did the same... feeling the warm, wet, sexy, girl-sex for the first time. Then Christine began to masturbate herself, while the rest of us massaged her tits and thighs, and she didn't stop until she was moaning with an orgasm. Wow!
Finally it was Jeff's turn. Since he hadn't felt me, I decided it would look queer if I did him, so I watched as the girls went at him. He asked the girls if they wanted to jack it, he basically taught them how to do it (though they had seen me do it) and he ended up up cumming like a gusher with Christine stroking his cock and Nancy feeling his balls.
Unfortunately, it never was repeated. Jeff wasn't really a friend, and Christine and Nancy were out of my league to ask for a date. (I was also too shy to even ask.) It was the end Middle School, and I went to a private all-boys school the next year for high school. But I'll never forget that amazing adventure in group-sex.