[F]inding Out My High School Sweetheart and her College Roommate Were Dor[M]room Cumsluts

Random story from when I was about 19. My high school sweetheart and I, we were each other’s firsts and stuck it out on-and-off for about two years before we drifted apart. We remained friends for a long time, occasionally had phone sex or jumped into bed for a while, even after she got engaged at 23.

At this point, though, I had thought she was still pretty innocent. We’d swap some sex stories from time to time but I didn’t really keep up on what was going on with her. First time I came to visit her at her college in the midwest, I dropped in to stay with her for a few days as she started her sophomore year. She was a bubbly and sweet blond from a wealthier family, on the curvy side with a pretty face and medium-length hair. I was looking forward to spending some time with her.

Her dorm was an all-girls floor for liberal arts students who wanted to focus on their books instead of partying, but because enforcing it was left up to other college girls, that was more of a tip than a rule. She’d told me she could put me up as long as there were no male voices causing a disturbance after the 8:00 pm curfew, and that her roommate would be there for Friday night, then gone for the rest of the three-day weekend.

When I got there, it didn’t take me long to notice the bowl of condoms the two of them kept on the mini-fridge, and it didn’t really surprise me that when her roommate, a quirky little brunette with kinky hair, climbed into the upper bunk to study after we’d had a couple drinks and gotten acquainted, my ex didn’t hesitate to make out and fool around.

What did surprise was that when she started sucking me off, she didn’t even keep it quiet. It was messy, noisy, and after I shot my load, her roommate asked her a question like nothing had happened. In the morning, her roommate ran off to an early class. She’d be back by to pick up her luggage but otherwise we had the room to ourselves.

While the ex went to work on my morning hard on with her mouth, I asked her about the night before and she owned up that they didn’t bother to kick each other out before sex at all. It turned out there was a “system” in this building, and that with the curfew, guys would come hang out in the lounge around sunset to fish around for whoever was down, then spend the night in whichever room they could get themselves into.

This was not only *not* the quiet, studious girls’ floor parents were told it was, it was where guys went to skip the nightlife entirely and randomly bang out those same quiet, studious girls. My quiet, studious ex, from a churchy conservative family, the one who had only let me go down on her on a dare and had been terrified her mother would find out she had ever sucked a dick, was living in it. My cock was throbbing thinking about it and she didn’t seem to know how to take my questions.

“Are you mad at me?”

“No, of course not, but how many guys are we talking about?”

“Not that many. I don’t fuck most of them but giving head is not… like… I can just do this all day. It’s not a big deal.”

“OK, but how many?”

“Um… Eight. Nine?”

She’d only told me about three, and the way she uptalked made it sound like a lie. I didn’t want to interrogate her but I was horny and curious, and I knew it could be easier to get a girl talking if she didn’t have to make eye contact. I watched her work on my cock on her hands and knees, then reached over for a condom and flipped her over.

She had a nice round ass and fucking her from behind was always a good view. I kissed the small of her back a few times while I rolled the rubber on, then started to enter her while she buried her head in the pillow.

“So you’ve sucked off nine guys in this bed? I didn’t know you were having so much fun at school. That’s actually pretty hot.”

I was pumping her slowly and listening to her familiar whimpering noises. She didn’t usually scream or cry out during sex, and she didn’t cum easily from fucking, so I wanted her to take her time and talk herself into an orgasm, but what she said next caught me by surprise.

“It is? That’s not… Um… It’s not… You know, I wasn’t counting… OK, I had sex with nine.”

Holy shit. If she fucked nine…

“You weren’t counting blowjobs?”

“No.”

“That’s OK. How many?”

She was breathing harder now, I could tell thinking about all the things she wasn’t supposed to be doing was turning her on. I had to admit, I liked hearing about this side of her, too.

“I don’t know, I’m sorry.”

“You can tell me, it’s OK.”

“No, it’s like, I really don’t know. Maybe two or three a week? Guys just come by to hang out and it’s all… just for fun.”

“You know, two semesters, three guys a week, that’s like a hundred and twenty at this point.”

She tensed up and laughed. “No! No! It can’t be. Not even anywhere near half that. No. The same guys come back a lot.”

“Oh, so you have regular customers. That’s cool. You ever take take care of anybody with your roommate?”

“No! I’m not… Um….”

She acted funny, like she was shutting down a little, and I gave her a firm spank with one hand to try to keep her focused, and switched to long, deep, forceful strokes.

“Um, what?”

“No, but… OK, sometimes if one of us isn’t here, like…”

“I get it. Like when you worked at the bookstore and you’d cover shifts for each other with your friend?”

“IT’S NOT A JOB.”

“OK, but say you’re busy with finals and one of ‘your’ guys stops by, she’ll jump in for you?”

“It’s what… Um…”

She was laughing again, but was having trouble talking. She had her head turned to the side, and I could see she was clenching her hand on the pillowcase and biting her lip. This topic was clearly getting to her and she didn’t want to admit it, and I finally managed to get one of her quiet, tense orgasms out of her.

Then, I slowed down to give her some room to breath. “Sometimes. Lindsay, too. She’s down the hall and Kevin dumped her over Christmas so when she got… lonely, I guess?”

Lindsay had been her best friend in high school for about a year, and there was a reason I remembered her as Bipolar Lindsay. She’d gotten drunk and tried to fuck me, once, but my ex didn’t know about that. “So you loaned her one?”

“Maybe two. I told you, it’s not a big deal. They’re not… boyfriends or anything. My roommate’s so bad, though. I think she’s had sex with more guys than I’ve blown.”

“Really? Do you ever just straight-up watch each other?”

“I mean… If we’re here, we’re here. Her beanbag over there, I was trying to study the first time, she’s making out on it drunk, and then it just kept going and… It was, like, really awkward to have her naked and climbing on him? I’m used to it now. I try to stay under the blanket if I’m having sex while she’s here. She just strips down wherever.”

“You should have told me about all this. I’d have scheduled a visit for when she was going to be here. Would it have been hot to watch your ex-boyfriend bang your roommate?”

She burst out laughing. “Shut up. FUCK. YOU. Fine, do you remember Brian?”

“Yeah, of course.”

Brian was the guy who had introduced us in high school. More specifically, he thought I was one of his best friends, and that he was introducing me to his girlfriend. He was in teenage love with her in the worst way, and she definitely was not his girlfriend. I wasn’t a very good friend, either, because she gave me her phone number and started telling him how “sweet” I was in every conversation. He’d ended up sitting by for years pining for her while I took his crush’s virginity.

Once, when we were in one of our “off” phases toward the end, she’d asked me if I’d be mad if she slept with him, just to see what it was like, and I didn’t care, but instead of sleeping with him, he’d somehow fucked that up, too, and she ended up getting it from behind in the shower from another one of his “best friends”. This guy had watched, probably emotionally devastated, while she walked out wearing a towel.

“He was here last week.”

Oh. Uh-oh. “Was he?“

She laughed. “Uh-huh. He left Friday.”

“Like, yesterday-Friday, when I got here?”

“Uh-huh.”

“Did you finally screw him?”

I could see she was grinning, messing with me on purpose. “That’s private.”

I grabbed a handful of her hair and started pumping her harder again. “Bullshit. Answer my question.”

She was biting her lip again. “OK, OK. He got here Tuesday. We had plenty of time together. I sucked him off a lot, right over there on the beanbag. Keep… OK, mmm, not so deep? You know how it is. Once I blew him the first time we just kept doing it all week. Thursday, we had sex.”

“On the beanbag or in this bed?”

“Here.”

“What position?

“I was on top.”

“Was it good?”

“No. He’s just not… I’m glad we did it, but I’m not going to do it with him again. I tried it, that was enough.”

“Was that awkward after?”

“I didn’t tell him, he wanted to have sex again in the morning before he went to the train station, but I just told him my period was starting to get out of it.”

I snickered. That poor guy just couldn’t win with her. He’d practically saved himself through high school thinking she’d be the love of his life. Then something clicked.

“You sucked him off instead, didn’t you?”

“Ye- Umm, maybe.”

“With your roommate here?”

I still had her head pinned down on the pillow by her hair, and could see her eyes darting around as she looked at the wall. I was practically grudge-fucking her at this point, and she wasn’t sure if she was in trouble with me or not. “…yes.”

She’d sucked him off that morning, before she went to meet me at the bus station. Her roommate had been hanging out while she sucked us both off that day. Fuck, that was it. I had planned to pull out and cum on her ass but I didn’t make it, and filled the condom inside her instead. She gasped, then started giggling. “You’re so weird,” then the giggling stopped. “Oh my God, why did I tell you all that? I feel, like, SO sleazy.”

I pulled out and she turned around and grabbed my cock, looking me in the eyes for the first time since we’d started fucking, then got up to get dressed, throwing on one of those generic grey college sweatshirt hoodies and some jeans. We walked off campus to a cheap diner to get breakfast, messy from sleep and sex, then snuck into the dorm shower together to clean up.

Source: reddit.com/r/gonewildstories/comments/ac6yow/finding_out_my_high_school_sweetheart_and_her