This is a story about how I fucked up my first threesome. It was the high school senior class play wrap party (all participants were 18). My family owned a hunting cabin deep in the Poconos woods, about two miles back behind our home off a single lane road, that we rented to New Yorkers during hunting season, so the party (like many others in high school) was in the empty cabin.
This takes place in 1975. I’d been in all four class plays during my high school career. I don’t know if it was like this elsewhere, but with all four there was always a lot of random making out during rehearsal breaks. Girls with steady boyfriends not in the play would just start pawing and kissing me, or someone else. There was no intercourse or oral, but a LOT of petting and under clothes grouping, finger blasting, and the like. This could happen four or five times a night, with different pairings.
It was always confusing for me. Five or ten minutes of lust and then, when rehearsal ended, it’s like it never happened.
I had the lead in the senior class play and there were two female leads. Chrissy played my spouse in the play and Sophie my love interest. Sophie’s best friend, Cassie, handled the lighting. Chrissy isn’t in this story, but there was the time she asked me to take her to a soft-porn movie at the drive-in. But that’s another story.
Sophie and I were good friends throughout high school. Both of us tended to hippy-type things. Pot, some acid, anti-war stuff, the Grateful Dead. We hung out with the same crowd. We dated on and off, never seriously. On the dates we’d make out like high schoolers do, but no intercourse.
She was (and at 67 still is) a beauty. Long reddish hair. When I say long – she had not cut her hair since she was 7. It went down to her knees, although she generally wore it wrapped up in braids that went up over her head and hung down shoulder length, or sometimes buns.
She was tall, for a girl – 5’7″ or 8″, and slender. Not thin, just a nice slender body with nice curves at the waist and hips. I was 5-9. So, she was the perfect height. She had the most delightful A-cups with little nipples that would get harder than pebbles and she loved for me to bite down on them when she was excited. No one shaved then, but she kept her mound trimmed fairly close. Like most young girls, she got gushing wet almost at will.
Cassie was a little shorter, a little fuller, with deep chestnut hair, lots of matching freckles, and large breasts. She wasn’t what you’d call a beauty but, as the song goes, she was alright. I actually don’t recall her ever dating anyone in high school, though.
So we’re at the cast party, no alcohol because our play directors – both teachers – were there. They were cool. But not THAT cool. We had soda and pizza, etc. for about 90 minutes it was everyone just hanging out and talking the stuff kids talked about then – Vietnam, would the Beatles get back together, etc. After the advisors left, people started pairing off, lights went down, and the beer, wine, and pot came out. My ‘girlfriend’ at the time had to work early the next day and left when the teachers did.
Sophie and I ended up chatting and, as usual, making fun of some of the others. We were on a two-seat sofa and Cassie perched on the arm next to me to join in. I don’t recall who started it but soon Sophie and I were kissing and grouping a little when Cassie was like, “Hey, what about me?”
She was only joking, but I was high enough not to care so I reached over, pulled her down on my lap and gave her the hottest french kiss I could muster. It went on for at least a minute and made me rock hard, which she felt under her thigh. I know because she reached down to grab it over my jeans. It was a split second, but . . . you know.
After a bit we noticed there were only half a dozen people left, one nearly passed out, the others paired off in corners and one very long-term couple in one of the bedrooms.
Sophie suggested we go somewhere more private. That’s how I ended up in a bedroom with two 18-year old girls and me. Sophie sat on a bed with her back against the wall, spread her legs and patted the bed for me to sit between them. I did and invited Cassie to do the same. We were all clothed at this point.
As Sophie leaned over to kiss me, I reached around to fondle Cassie’s breasts over her shirt. Her nipples (still the largest I have ever seen) were soon jutting out their full 1 ½ inches, even under her bra and shirt. Sophie reached down the front of my shirt to caress my nipples, and then leaned forward to kiss Cassie.
I leaned to one side to give them more room. I wiggled a hand behind me to rub Sophie’s pussy – still over her clothes, while working the other over Cassie’s shoulder and down under her bra to pinch her nipple while she and Sophie continued their kissing. Cassie moved down so her head was nearly in my lap and I was left with a choice between Sophie’s pussy and Cassie’s nipple.
I took a chance and began unbuttoning Cassie’s shirt, which she didn’t seem to mind. Once open, Sophie ran her hand down from Cassie’s chin, over her chest and slipped it over her breast under the bra. I thought I would come right there.
I lowered my hand to Cassie’s waist and she let me undo her belt and the top button of her jeans. I slid my hand down and caressed her mound over her panties while she and Sophie tongued one another. She moaned deeply and rose her pelvis up against my hand. I took it as an invitation and moved my hand under her panties and quickly inserted a finger up her pussy. She responded by grinding against the heal of my hand.
While I was busy with this, Sophie and Cassie had worked to remove one another’s shirts and bras and they were trading licking each other’s nipples. Sophie started to work her hand into my jeans, but I couldn’t help her and keep my hand in Cassie’s pussy. I put a second finger into Cassie and pressed the heal of my hand harder into (I know now) her clit and rubbed. In like 30 seconds she was coming. My hand was absolutely drenched.
When Cassie came she sat up a little and Sophie used the opportunity to get my belt unbuckled and unzip my jeans. At this point, I’d probably been hard for two hours, so I think she stroked me only two, maybe three times before I came all over her hand, still inside my tighty whities.
When I calmed down, I started to undo Sophie’s jeans and she stopped me. “If we don’t’ stop now this may go further than we want.”
THAT’S when I fucked it up.
I took that as a signal she didn’t want to go any further and pulled back. I sat up against the other wall and put my arms on the shoulders of both girls giving them nice little pecks on the lips and said something stupid like, “that was fun, why did we wait all year to do this?” There were little hugs and smiles, but the lust began to subside and pretty soon they were looking at their watches.
Knowing what I know now, I probably could have ended up having sex with both of them that night. As it was, I have a memory I STILL masturbate to, but if only . . . .
Source: reddit.com/r/gonewildstories/comments/nme9bw/how_i_messed_up_the_ending_of_my_first_threesome
She indicated discomfort and you backed off. You did good.