This happened summer of 2017, when I was fortunate enough to have a very good week in an otherwise dull July. First with a rather shy girl who’d just turned 19, and later my first time with a couple I’ve written about previously.
Some background on me: I was 28, 6-ft, 195 lbs. Average to in-shape. I’d posted an ad on CL (my first and only one, as I hadn’t discovered Reddit at that time) looking specifically for a submissive girl. I think I was just in a particular mood that day to be more dominant than usual. And when I say dom/sub, know that I’m using those terms loosely. I have a lot of respect for practitioners of that lifestyle, but I’m not arrogant enough to pretend I know exactly what that lifestyle is. In this case, I just wanted to fuck, on my own terms, with someone who wanted just as badly to be used.
Cassie responded to my ad about a week later. When I was no longer in a particularly aggressive mood. I was at work (it was morning) and couldn’t leave until that evening. Which sucked, because she was very straightforward: she wanted to be fucked right now, please come over, here’s my pic, I’m 19, I’ve only had sex once before…
I loved my job. Some semblance of responsibility was the only thing keeping me from rushing out of there. Like I said, I’m 28. While I don’t have a particular interest in younger girls (prefer to know that while I was in college, they were at least in HS) her absolute need to be fucked (and her pic; she was hot) was an absolute turn-on. She also had a (complicated?) relationship and couldn’t trade numbers. We emailed all day, part of me worried this was a dude desperate for…something? But I was enjoying the messages, the follow-up photos of her, the raging hard-on I was trying to keep hidden from coworkers, and the implication that we might meet up that night.
We did. After work I bolted home to shower. Then she messaged me that her parents were home after all. She was living at home for the summer. So me, suggesting something I never have before, said “Well, I can pick you up and we can park nearby and have a quickie.” Great come-on, right? I didn’t expect her to say yes. She did.
I drove over and parked half a block down from her house. Luckily it was a quiet and sparse neighborhood. She came out, headed straight to my car, and we realized we could have fun right there. Within sight of her house, which made her more comfortable. She was very shy. Shorter, about 5’2, and curvy. I think that’s what she was nervous about. But she wasn’t overweight at all. Whoever is setting these girls up with the expectation they must be all bones is absolutely fucking crazy. Cassie was perfect.
We moved to the back seat. It was roomy enough. I kissed her, and she responded with lust. Her hands felt me up, her tongue found mine. Soft, sexy whimpers of need escaped her. “I can’t be gone long,” she said. So it was on. I removed her shirt and bra, and realized her breasts immediately rivaled any I’d seen before. Hardly more than a handful each, easy to hold and massage in my hands as I kissed her, tracing my tongue down her neck, softly biting her shoulder, down her chest, teasing each nipple with tongue-strokes and gentle bites. Then down her stomach. We took off her jeans and panties. She was shaved smooth. Not a requirement for me, but I appreciated that she did what she thought I’d like most. I took some time, not as much as I would’ve liked, teasing her inner thighs and just above her labia. Then I ran my tongue over her lips, parting them forcefully, and tasting her for the first time. She was amazing.
I couldn’t eat her out long. Time, time, time. So I awkwardly got my pants off, and basically shoved my dick in her mouth. She gagged; her eyes locked with mine and she proceeded to suck me off vigorously. Not skilled, but eager. She really wanted to please. She kept gagging. I decided it was time to feel how tight her pussy was.
She was wet; my spit and her own slickness. I slid in a couple inches before her body bucked and she pulled back slightly. She was seriously that tight. I held her, looked into her eyes. She was panting already. I withdrew a little and spit down onto my cock and slid it back in. Four inches. Six. Six-and-a-half. To the hilt. She’d either already cum or was close.
There’s nothing more to describe here than all-out fucking. It was brief. Time was of the essence. She couldn’t handle much. I’d been hard all day and was fucking an absolute beauty. At the end I pulled out, ready to cum on her stomach. She misread my cue and bent down and took me in her mouth again. I came, hard. I did warn her, but she didn’t pull me out. A lot of it ended up on the car seat. We both were panting, and just sat there for a couple minutes. I offered her water and gum. She took a sip but the gum wasn’t a flavor she liked. Then she got dressed, we kissed, and she went inside. And I drove home happy.
And then a couple days later, the yuppie couple. I don’t know what constitutes yuppie these days. But it was part of their Reddit username, so there. They posted on Reddit but also responded to one of my posts. I sent them a lengthy PM, and we got to chatting. This couple was legitimately hot. And I mean, by Hollywood standards. I think a lot of people are hot, but this couple…I mean, I was honored to be chosen. She’s 5’5, blonde, very skinny. Very white-skin. I thought Scandinavian, turns out German. He was also blonde, just over six feet, fit, scruffy. Both blue-eyed. She was so fragile-looking. I couldn’t imagine how they fucked without her getting bruised up, and said so. We got comfortable enough with each other that we decided to grab drinks together.
We hit it off well. They’d been curious about group sex for awhile. I took a risk and admitted that I was bi, but generally am involved in straight threesomes. He wasn’t put off at all. He was admittedly curious, but they mainly wanted this to be about her. Which, duh, I’m totally on board with. That night wasn’t going to work, because they were both exhausted from work. I joked about the next day, and she looked at him and said, “Aren’t you off too?” And like that, it went from a longshot to scheduled. We had another round, got to talking about Hamilton, which they’d seen in Chicago (bastards) and I learned a little more of what they were hoping for, threesome-wise. Not DP. He was pretty hung apparently, and she thought between him and me, it might just hurt her and ruin the fun. I asked if they enjoyed anal, which she did. When we parted ways, he asked her to kiss me. She did, and he remarked it was the first time he’d seen her do anything with anyone else.
The next day I waited for them to message me. It was shortly before noon, and I was able to leave early that day. I went to their place, not far from mine, as we’d discovered, and he let me in. He was in sweatpants, shirtless. He told me she was in the bedroom waiting. They’d had a couple mimosas each already, and offered me one. I accepted. We might as well all taste like OJ. They had Pandora on in the bedroom (their place was gorgeous by the way; won’t go into detail, but it was) and she was sitting on the bed cross-legged, in a short skirt, bare-chested. She was sipping her mimosa. It was bright in the room, and her skin was so sexily pale. Some girls hate being called pale, she embraced it. She joked that she was worried if she didn’t start before I got there, she’d chicken out. And with that, he climbed onto the bed and pulled his sweats down, letting his cock out. And she went down on him right there. Apparently picking up where they’d left off when he’d answered the door.
Usually I’m the one to lead in a threesome, until the girl is relaxed and comfortable. This was refreshingly different. He motioned me over, I downed my drink fast and joined them on the bed, losing my clothes along the way. She blew both of us, taking turns, kindly spending more time on me since I was their guest (ha). She remarked on my thickness and I appreciated the compliment, who wouldn’t, and she admitted we wouldn’t be trying DP. We were too big for her. But she wanted to get fucked hard by both of us.
We laid her down and she continued worshipping my cock as he pulled her skirt off. He didn’t go down on her; she was already wet. He just slapped his dick against her labia, then slid it between her lips until he was slick enough to slide inside her. Instantly her mouth went crazy on me. Her tongue swirled and licked over my shaft, she turned her head to the side so I could push into her throat. He started fucking her pretty hard, making her gag on me as he held her hips still and I massaged her breasts. After several minutes he tapped my shoulder. I’d been busy watching her mouth work. We switched places.
They knew I was bi, so I wasn’t afraid of going down on her first. He hadn’t cum yet, so she only tasted of herself. Very, very sweet. That was actually something he’d said the night before. That I’d never taste someone sweeter (I since have). I enjoyed exploring her, mouth and fingers, while he had his turn with her mouth. Then I straightened up and somewhat copied his move on her pussy before entering. It had looked like it felt sensational. It did. He was grinning, she was grinning around his cock, and I slid into her. She felt as though she’d normally be tight, but he’d stretched her out a bit for me. She was a tiny person though, as I said, and that with how wet she was got me close to cumming. I asked to turn her over. She rolled onto her stomach but I kept her from getting onto her knees. Instead, I pulled her legs apart and penetrated her again as she lay on her stomach. He’d gotten up and grabbed his cell and asked if he could take a couple pics. For them, not to share. Of course I said yes.
After awhile I pulled out. I wanted to give him another turn, but she rolled over and asked if I was ready to cum. I hadn’t been ready, but seeing her there like that, in that moment, actually looking hopeful, made it so. She waved her hand, like a climb up on me motion, so I did. She sucked me off again briefly, and then when I made a particular noise, started using just her hand, holding me over her breasts. I was aware of him just next to us with the phone as I came, covering her breasts, her neck, her chin. He stopped recording and got behind me, ready to fuck her again. I got off.
She didn’t clean up. He fucked her missionary, leaning down close to her face, looking into her eyes. She came, and then he did. I sat back and enjoyed watching. When he withdrew, she turned to look at me. “Can you go again?” she asked. I wasn’t expecting that. I was ready again though, hard after watching them finish. God bless quick recovery time. “Do you want to taste?” she said as I got ready. I looked at him. He just shrugged. I went for it. Honestly, I couldn’t taste much of him on her. He must have cum pretty deep inside. I entered her again, and sure enough it was easy; she was soaked from her cum and his. I pounded her for a long time, working up another load. He took a couple more pics, then joined me in spitroasting her again.
We took turns again. She came twice more. After switching places a few times, mixing up positions, and just generally rolling around and having fun, him and I each came one more time. Him on her chest, me on her stomach after pulling out. Exhausted, we just hung out on the bed for a bit. They offered me their shower while she immediately began pulling the sheets from the bed and throwing them into a pile to be washed. I took a quick shower and rejoined them in the living room. She still hadn’t cleaned all the cum off her, and went to jump in the shower while I chatted with him. When she came back in a towel, she kissed both of us.
I took off then. More than satisfied, obviously. They sent me a message later, with a couple of the photos. We had a few more encounters after that, until they started trying for a family.
Ah, and Cassie. We messaged quite a bit, flirting and trying to arrange another time. It was a few weeks after this that I started to get annoyed with her not committing. I was at a hotel room that I’d gotten to host an…event…of sorts. She started messaging me and I told her about said event and invited her to the room to help me warm up. And after I tapped “Send” on that message, I never heard from her again.
Every once in awhile, it’s okay to shoot yourself in the foot.
Source: reddit.com/r/gonewildstories/comments/bhfasp/hot_week_in_july_mf_with_a_19yearold_and_a_couple
I didn’t have Reddit at the time… But a couple of days later I got a message on Reddit.