March 9, 2015
My First Time
This is a true story - happened many years ago when I was living with a girlfriend, Stephanie. I was about 25, Stephanie 20 or 21.
Stephanie was a little hottie - slim with gorgeous little a-cup breasts, dark brown nipples, never wore a bra, loved to flaunt it. She was one of those effervescent, life of the party types - and a bit of an exhibitionist. For instance, we had matchstick blinds in the lounge room of our ground-floor apartment, the type that you could easily see thru when the lights are on - more so because we lived on a steep slope, on the low side of the street. Stephanie used to love us to have early-evening sex in that room, knowing that men trudging home from work would be able to see us. While we were fucking she would tell me if anyone spotted us, if any one stopped and watched. Anyway, I digress. This story is about my first cuckold experience, one special night.
Stephanie’s female colleague Jenny was still living at home, still a virgin, and a bit hung up about it. So Stephanie agreed to help her out - arranged a double date with some guy they dealt with thru work. I forget his name, call him Joe. The idea was we all have a night out together with a bit of alcohol involved, then all spend the night at our place - a small two-bedroom apartment. The night went to plan, a nice dinner with plenty of wine, and we’re all nicely tipsy. Until back at the apartment Jenny quietly decided she couldn’t go thru with ‘the deed’. So we made up a bed for her on the lounge room floor, nothing much needed to be said. Joe was easygoing about it, no big deal. And we continued on playing some drinking games, that sort of thing, but I was beat from a week at work and left the three of them at it, went to bed by myself without a second thought. I could hear them laughing and flirting and carrying on, but I didn’t sense any “danger” - Joe had been invited by Jenny, and Jenny was part of the trio still sitting around the kitchen table.
It must have been around 03:00am when my girlfriend, Stephanie, wakes me up by whispering in my ear, “Please fuck me!” in little-girl voice. Did not take long to wake me up! And she was wet, as wet as I can ever recall her being. Not the I’ve-just-been-fucked slippery and wet, it was the hot-and-horny-and-ready-for-sex naturally-lubricated wet. Somebody had got her in this state, and it wasn’t me! Now, cuckoldom was a fantasy of mine, it had featured in our regular pillow talk. But Stephanie was never that much into it - she tolerated it. On this occasion, while my fingers were sliding around that sopping wet little pussy and my tongue was teasing her hard little nipples, I said, “I thought you would be with Joe”. Stephanie was fairly drunk; she just giggled and said, “I thought about it!”
I moved over to her neck, and as I kissed it below the ear, fingers still sliding thru her wetness, I whispered, “Why don’t you?” Stephanie’s voice turned cool, I had for sure ruined the hot fuck we were about to have. But what she said was, “Do you want me to?”. My head fell to her chest, my eyes closed, and I hesitated for a good three or four seconds before saying just one word: “Yes”. Stephanie didn’t say another word; she got out of bed and walked naked towards the door. All I said was “leave the door open”.
Joe was in our old pine-wood and foam-mattress double bed in the spare bedroom, right next to our main bedroom. Stephanie left his door open as well. I heard her get into Joe’s bed, naked. I clearly heard her say, “Please fuck me” in that same little-girl voice. And he did. Joe fucked my girlfriend, knowing I was in the next room. I could hear everything. My mind was contorted - I was so turned on I was shaking, but I was so jealous I wanted to go in there and call her back. I masturbated while Joe fucked my girlfriend within earshot.
Joe didn’t engage in any foreplay, he was right into it. I didn’t see any of this, but I could hear it - from the time she slipped naked into his bed to the time Joe started squeaking the bed frame was only long enough for the obvious to happen: Stephanie slipped into the bed and asked Joe to fuck her. Their lips met. Joe feels her naked breasts against him, probably feels how wet she is. Stephanie then rolled onto her back and Joe rolled right on top of her. Stephanie’s legs opened, her knees came up, Joe got partially onto his knees between my girlfriend’s legs. And inserted his hard cock into that wetness I had been feeling less than a minute ago.
And then they fucked.
They fucked for probably 10 minutes, didn’t sound like they changed position at all. I could clearly hear the squelch of his cock in Stephanie’s juices. I could clearly hear his belly or balls slapping against my girlfriend. I could hear Joe’s heavy breathing; I could hear the wooden bed frame groaning. I clearly heard his pace increase, the slapping got louder, and I could tell when he pumped his seed inside my girlfriend. Stephanie was on her back with her knees up, legs open wide, wetter than I’ve ever known her to be, probably tongue-kissing Joe. And as Joe is fiercely pumping his cum into her, I slowly masturbated.
It went quiet for a bit, and then there were a couple of hours of annoying exaggerated lip smacking kissing and whispering. Stephanie told me later - when I asked why they only did it once - that Joe was “ready” but was afraid I would hear them and wake up.
As dawn started to lighten the sky outside, Stephanie left Joe’s bed, closed both doors and padded naked into our bedroom. And then we fucked. Stephanie didn’t get any foreplay out of me either, but I figured Joe had warmed her up nicely. He had pumped her full of his cum and they had lay in bed for a couple of hours, so most of it was still inside her. And I fucked her like that, with Joe’s cum squelching and leaking out around my cock. We locked tongues and we fucked like a couple of animals. Joe must have heard us.
Joe took off before we could have an awkward breakfast, and later I drove Jenny home in almost complete silence - she must have heard it all as well. I rushed home for a bit more cuckold sex, but Stephanie was upset - embarrassed and upset: “I was D.R.U.N.K.” It was the end for us really - she never could accept I could love her AND enjoy her fucking other men. There were other occasions but never so “real” - Stephanie having an affair with her boss is nowhere near as much “fun” as her fucking some guy in the next room.