“Sleeping with [My] Ex-G[F]’s Roommate

I want to share a series of my most memorable sexual encounters. Some are passionate, some are primal, and some are just funny (at my expense). I’m going through them temporally so, here’s the third story, in this case the one of my first time with Shannon’s housemate, Mandy:

So if you didn’t read my previous story, I just briefly noted that my first girlfriend, a gothy girl named Shannon, cheated on me and put a “curse” on my love life. Anyway, Shannon had a housemate, Mandy, who lived in the other bedroom in the house we all rented. I never officially moved in, but I helped pay utilities since I was constantly over there visiting Shannon. Sometimes when Shannon was off at school or work I’d be there alone or sometimes Mandy would be home too.

I’d be exercising out back in the yard, or eating in the living room and Mandy would come talk with me, usually about some nerdy show we both liked, college stuff, or about her boy troubles. While I was physically attracted to Shannon for her pale skin, black hair, giant tits, sultry eyes, etc we fought a lot about dumb shit. I found that besides when we were fucking, I actually enjoyed being home with Mandy more.

Mandy was a nice girl, about five and half feet tall, shoulder length dirty blonde hair, bright hazel eyes, tan complexion from being outdoors quite a bit. We talked about fitness often because we were both more athletic than Shannon, who never wanted to hear it. Mandy was very insecure about her body though, because she felt she had no curves.

“Who is going to want me? I have literally no tits,” she said to me one afternoon grabbing at her own chest making a finger slip motion downward to emphasize that there was nothing there.

After living together for about 6 months, that’s the firs time I really saw her in a sexual light, imagining her hands running over her nipples below the fabric. It was just a quick thought though, remembering this is my girlfriend’s housemate. I tried to just placate her fears and move on.

“Lots of guys like a small bust,” I said trying to hold a matter-of-fact tone, “You’re thin and pretty, so honestly you have nothing to worry about.”

I remember her smiling so genuinely when I said that. She was nodding as she barely whispered out a “thanks” before quickly walking away red-faced. Things were never more tense than that between us while I was dating Shannon.

Immediately after the breakup with Shannon, Mandy had told me about the weird “curse” ritual Shannon had carried out trying to damn my love life for “driving her to cheat to feel good about herself”. I was happy to hear Mandy thought that excuse sounded as pathetic and strange as I did, but I also didn’t want to really see or hear from any mutual friends Shannon and I had. So after gathering my things from their house, I didn’t see Mandy for about 6 months.

After a semester passed I happened to see Mandy on campus. I had healed pretty well by then, so seeing her was a pleasant surprise. Neither of us had much time to talk on our ways to our next classes, so Mandy asked if I wanted to catch up at the bar just outside campus later tonight. I agreed even though I’m not much for bars or clubs. The day passed and I found myself not really paying much attention in class, thinking about how great Mandy and I had always gotten along and how it would be good to talk to her again like we used to.

I found her sitting on the stool right in front of the bartender and already had one of my favorite beers there waiting for me. We got to talking like six months hadn’t passed by without so much as a hello. Theorizing about series finales and the like, and of course about her troubled love life. It always came down to her lack of tits and ass.

“Look, I don’t know how many times I have to tell you this,” I started, “but lots of-” “Yeah yeah,” she cut me off with a hand wave, “Lot of guys like skinny girls with no chest, but no YOU” “I never said I didn’t like petite women,” I said blindsided and on the defensive.

“Right ok, but why would you have stayed with that selfish bitch,” she said it with disgust, “for so long if not for those massive boobs?”

I was kind of hurt at first, but then remembered that yeah, that was basically the reason I tolerated her for so long.

“If I’m being honest with you, Mandy, for the last few months I was seeing her I often found myself thinking I picked the wrong roommate,” I immediately regretted saying this, but to my surprise Mandy just smiled and turned red like she did when she brushed her chest all those months ago.

“You really mean that?” she asked almost shyly.

“Absolutely,” I doubled down. It was true, too.

We got onto other subjects and talked and drank for another half hour or so, then Mandy suddenly said, “Hey do you want to walk me home? Let’s play some games or watch something.” I had an early day the following day, but I also really wanted to just spend some time with a woman and didn’t feel like I could drive all the way back to my apartment a couple towns away. I agreed and we walked to her place, which was of course hers and Shannon’s.

“I don’t really want to see her,” I told Mandy as we approached, “Can I climb in through your window if she’s in the living room?”

She laughed and said, “So you want me to sneak a boy in through my window?”

“It does sound kind of silly when you put it like that, but yes,” I said back half amused and half dreading the thought of seeing Shannon again.

“Ok,” she nodded and then went inside. A few minutes later her window opened, “She’s eating and watching something out there, no idea for how long.”

We drunkenly tried to pop the screen out quietly and it didn’t really work too well. Whisper laughing, I climbed inside and we played some fighting game in which she completely stomped me, and then watched a movie while we talked quietly. I had completely lost track of time.

“Fuck…I have class early tomorrow,” I lamented, “I better go.”

“I mean, you don’t HAVE to,” she said sheepishly.

I looked over at her quizzically.

“Well, I mean, what you’re going to drive home, sleep for 4 hours, then drive right back?” she questioned, “Why not stay here and save yourself a couple hours?”

“I appreciate the offer, but I don’t want to sleep on the couch out there and risk seeing her,” I explained.

Mandy shook her head and rolled her eyes, “You can sleep in here with me. Not like sleep sleep with me, but like in my bed.”

“Really?” I asked one last time.

“Nooo, I’m offering just so you don’t break my fucking window screen trying t ostumble out of here,” she teased.

I thanked her and got ready to sleep. I kept my shirt and boxers on which I normally wouldn’t, but I was comfortable enough. We awkwardly positioned ourselves like Egyptian mummies, flat on our backs solemnly looking up with hands folded on the chest. I drifted off pretty quickly.

Around three in the morning I half woke up to find Mandy and I were cuddling. She was the little spoon and I had one arm and one leg draped over her, with my face resting against the back of her head. I kissed it lightly in my groggy state. Realizing what I had done I tensed up and tried to pull away slowly so as not to wake her, but Mandy grabbed my arm draping over her and pulled it back across her, resting my palm on her breast.

“Uhh,” I stuttered dumbly.

“I thought you had to get up early?” she said coyly.

With a boldness that I would only be capable of in the dark and dead of the night I rolled her towards me, kissed her deeply and climbed on top of her. Mandy kissed me back hungrily, moaning as I massaged her breasts that she was so insecure about. I nearly tore her top off, then kissed her from lips to neck to chest, sucking her tiny perky nipples and swirling my tongue around them.

“You sure they’re not too small?’ she whispered to me lustily.

“They’re fucking perfect,” I said, pausing to take me shirt off.

We both disrobed completely, then went back to kissing, but with my fully erect cock pressed between us point upwards. I was making a pool of precum on her stomach as we grinded and made out.

“Hurry up and get inside me,” she urged, “I’ve waited months. and I can’t wait anymore.”

That kind of shocked me to hear, but I only hesitated a few seconds before guiding my throbbing head into her. She gasped a bit.

“You sure it’s not too small?” I whispered impishly into her ear. She slapped my shoulder playfully.

“Ass!” she said maybe a little too loud. We both stifled giggles as I pushed a few more inches into her.

I began to slowly thrust into her, then I’d pull back a it, do a few shallow thrusts, then plunge all the way in. Making it into a game of sorts trying to get her to make a loud moan or gasp. At this point a part of me hoped we’d wake Shannon up with our frantic night sex. I began pounding deeply into Mandy so that the whole bed shook. Mandy moaned louder and tried to suck in air as best she could.

“I’m going to cum,” she barely managed to get out, “don’t change anything.”

I kept my pace and meditated on imagining Shannon hearing us, hearing me with her housemate. I felt the first contractions of Mandy’s orgasm before she could make a sound. That silence that I knew to be her unable to let out her breath because of the intense pleasure sent me over the edge. I groaned loudly, as loud as I could without it being comical, as my cum pulsed into Mandy. I could feel the warm wetness filling her and surrounding my twitching member. Mandy joined me in moaning loudly, all pretense of discretion now gone. She had mentioned in our talks before that she was “vocal” and she was not exaggerating.

After about a dozen spurts, I collapsed onto her, my cock still twitching with some aftershocks. Every little spasm would make Mandy jump and let out a small gasp or moan. We kissed in our aftermath, our juices soaking the entire front of our hips.

“Oh!” she said pleasantly surprised, “So it’s true!”

I never get soft if I don’t want to, no refractory period really to speak of. Maybe like 30 seconds where it get a little floppy and then right back to full mast. I guess Shannon had mentioned that to her.

“She acknowledged one of my talents at least,” I joked.

“Actually she complained that she only wants like 10 minutes of sex,” Mandy revealed incredulously, “So she saw it as annoying.”

That actually made sense. I had come to realize during my many months of meditation in solitude that Shannon seemed to think of sex more as a tool to control men than something of mutual pleasure. I began thrusting faster again, and Mandy arched her back in pleasure as her now super sensitive pussy was lit up with sensation again.

“What do you think of it?” I teased.

“Her loss,” Mandy said with a smirk.

We fucked basically all morning, until eventually we heard the front door slam loudly. I couldn’t help but laugh and neither could Mandy, though she told me to stop halfheartedly. I skipped class that morning. And afternoon.

Mandy and I hooked up off and on for the next few months before Shannon moved out. Without the fun of sneaking around and annoying Shannon, the spark was dead. Mandy got herself a boyfriend soon after, and apparently he liked her small chest as much as I did, because a few years later they were engaged. As of today, they are now seemingly happily married if the Book of Faces is to be believed. Shannon is still alone.

Source: reddit.com/r/gonewildstories/comments/cdlbqm/sleeping_with_my_exgfs_roommate