The most embarrassing thing I did in college [MFF]

Hi all. I’m new at this story-writing thing, so we’ll see how this goes. This is a story about one of the craziest things I did in college with my girlfriend at the time. If it matters, I would describe myself as generally very average looking, a bit on the tall and thin side. This was towards the end of my college years, so I was maybe twenty-two.

My girlfriend and I weren’t in a very serious relationship. Admittedly, it was getting to the point where I was spending a few nights a week in her bed, but we were both pretty laissez-faire and had few expectations. Kate, let’s call her, was typically shy. I liked her smile and the way she blushed when she talked about sex. She wasn’t a prude, but she seemed insecure about showing off her body in public, and she would always demur when things got too personal.

Kate’s roommate (let’s call her Megan) was the polar opposite. Megan was one of the most socially outgoing people I knew. She could also be offputtingly direct. For example, one time we were all together at a house party. When a couple we knew got up to leave, the had barely shut the door before Megan announced to the group that the couple had clearly gone off to have sex. To be honest, I took a guilty pleasure in watching the way her and Kate interacted together, the way they made a point to cuddle up to each other at parties, and even the way Megan would talk about Kate. One time, Megan asked Kate in front of a group of people whether she would change anything about her body if she could, making reference to her dramatic hour-glass figure she always tried to cover up. Kate got embarrassed and couldn’t come up with a coherent response.

When Kate and I slept together it was always at their place, and I usually worried about Megan walking in on us. The very first time we were together, we did it on the living room couch with Megan sleeping just down the hall. We were quiet, and it was very late at night, but she could have easily came to the kitchen to get a glass of water, and things would have gotten awkward fast. We usually tried to move to Kate’s room, but sometimes things happened where they happened, and in any case the apartment walls were thin.

The night when things got really out of hand started innocuously enough. The three of us were sitting around, drinking wine and watching a movie. Kate was learning on me, and I was massaging her arms and upper back with the tips of my fingers. The wine was starting to take effect on all of us and for a while we chatted about Megan’s recent ex-boyfriend. She had dumped one boyfriend after another that semester, and we would poke fun at her for it. Megan was conventionally attractive, with long blonde hair and an athletic body, and I had always secretly wondered why she had such a bad time on the dating market.

At some point as the night wore on, Kate and I moved from a sitting position to lying down and spooning. We were both tired and tipsy. Megan was sitting close-by in a recliner, sipping rose and watching the television. I kept massaging Kate while we cuddled and slowly I began to notice her mood change. She rolled over to face me and wrapped her arms tightly around me. I kissed the top of her head and continued to massage her back muscles. Over Kate’s head I could see Megan looking in our direction. She was smiling almost like she could feel what I was feeling, Kate’s warm curves in my hands and a tingling sensation between my legs.

“Are you two having fun over there?” she asked. She inclined her head and twirled her hair with her finger-tips.

“Your roommate is very cozy,” I said back.

I squeezed Kate harder and she let out a little groan. Slowly, I shifted my hips in what I hoped was a subtle motion, pressing our crotches together through our clothes. Suddenly I was feeling very confined by my jeans. I knew from experience that Kate likely wasn’t wearing anything at all under her pajamas. The pressure of pushing against her was starting to feel really good, but I felt embarrassed too. In that moment, I wanted nothing more than to run my hands over Kate’s generous ass, kiss her full lips, and tear those pajamas off her, but it didn’t register as a possibility, not with Megan watching. I started thinking of excuses that would get us out of the living room and into her bedroom.

In the meantime, I settled for making out. After a few minutes, I kissed Kate on the neck, causing her to groan a little, hopefully beyond Megan’s earshot. She was starting to look both horny and annoyed, which was no mystery to me. We both knew exactly how sensitive she was, and how fast she lost her sense of self-control when she was stimulated the right way.

Then, a mysterious passed over her face. She reached down to my crotch and wrapped her fingers around my now bulging cock. She held me just long enough to make her point, and then stood up, announcing that she had to go to the bathroom. I felt a jab of fear and insecurity. Kate was no longer between me and Megan. I thought my jeans would probably hide my arousal, but I had no way to be sure.

Megan and I both watched Kate as she went down the hall, each ass cheek rising and falling in her tight clothes as she walked.

“Your girlfriend is really something,” said Megan. She was blushing. I had never seen her like this before, and I felt more arousal followed by fear as my cock twitched involuntarily in my pants.

“Yeah,” was all the response I could muster. I tried to look straight at the movie and ignore the obvious tension in the air.

Kate came back, and soon we were making out again. I could smell her arousal on the edge of her perfume. Then she shifted on top of me. Her legs were spread, and she using her weight to put pressure on her crotch. For a moment, I thought I might be able to feel her wetness through both our clothes. To my own shock, I slid my hand underneath her pajama bottoms and squeezed her ass, pressing her crotch harder against mine. Her face was red but she was grinning ear to ear. I could see Megan had shifted position, her legs now firmly pressed together. She was still watching the movie while not-so-subtly glancing over at us now and again.

Then, Kate did something I really wasn’t expecting: she started tugging at my jeans. One one hand, I relished the feeling of the fabric sliding across my skin; my cock had been aching for half an hour and I was getting desperate. On the other hand, I was petrified by the thought that my genitals were about to be in the open air. Megan was watching us with a carefully neutral expression on her face, one I couldn’t read.

I couldn’t believe this was happening. I could see the base of my shaft just hidden by the top of my jeans. It felt like I was going over the peak of a rollercoaster. Then, without warning, Kate pulled hard and my dick sprung out into the open air. I watched Megan’s face carefully as she looked me up and down. She didn’t say anything, but she was breathing through her mouth now and her eyebrows raised a little as she made eye contact with me.

Kate turned around, putting her ass in my face. I ran my hands over her again, massaging her warm breasts under her pajamas. She casually moved forward, taking my cock in her mouth. It felt incredible to finally have pressure right where I needed it. I thrust into her, flexing my cock and being rewarded with a rush of endorphins.

I slid Kate’s bottoms off her, revealing her wet, open pussy. I had been teasing her all night and in hindsight it was remarkable that she put up with it as long as she did without fucking and/or killing me. I gave her a few broad licks before pressed my face up against her, my tongue moving around in circles. As I ate her, I felt the intensity building at the base of my cock.

Kate bore down on me with her pussy, groaning loudly. I breathed sharply. Megan could surely see every inch of me as I thrust into her roommate. I was dying to know what she was doing, but I couldn’t see anything in this position and I wasn’t going to stop Kate when she was in the zone. She was humping my face desperately now, and I knew she was on the verge of release. I gave her a few big, wet kisses before focusing the strokes of my tongue on her clit. Her back was arched and her butt was swaying in the air, as if she was trying to be penetrated as deeply as possible. She was moaning deep in her diaphragm now, and I knew she didn’t have long. I licked her up and down while she shuddered and released, her pussy pulsing and clenching. After a few more licks, I figured I could poke my head up safely.

It turned out Megan was enjoying the show. Her legs were spread wide over the armrests of her chair and her hand was in her pants. She was still wearing all of her clothes, but her shirt was unbuttoned and she was rubbing one nipple between her thumb and forefingers. I watched her with disbelief over Kate’s still swaying ass cheeks.

“Do you like what you see?” I said, before I could stop myself. Megan gasped a little in response and began rubbing herself a little harder.

Kate was still enthusiastically deep-throating my cock and didn’t show any sign that she noticed, although she could clearly hear. I gently stroked her hair with one hand, wanting so badly to push her head down on me so I could control the penetration. I gave her kisses on the ass and pussy while restraining my urge to face-fuck her.

Megan’s mouth was hanging open. She had pushed aside her shirt and I could see that she had perky breasts and hard nipples.

“Want to cum with me?” I asked. It was a surreal moment, and I felt disconnected from my words as I spoke them. Megan’s eyes widened a little and she moaned out loud.

“Are you close?” she asked, her face scrunching a bit.

“I’m about to fill her with cum” I said, still not believing the words coming out of my mouth. I felt like I was teetering on a cliff, so close to the point of no return that I couldn’t stop imagining what it would be like to release into Kate. Megan’s fingers were making an audible sound as they moved inside her.

“Kate,” I grunted, “can I hold your head while I cum?” She nodded and without hesitation I pushed her down on me, feeling her lips pressing around my base. Megan threw her head back and started to visibly shake with her climax. I flexed my cock in Kate and suddenly I was passing the point of no return too. An intense muscle spasm gripped my cock with so much pressure that I almost cried out loud, but before I could pull out the pressure began releasing in gratifying spurts. With every contraction I felt my cock pumping cum into Kate and relief spreading over me like a glow.

After I was done, Kate swallowed and pulled back, letting my twitching cock fall against me. She lay back on me with a cocky smile. I could see Megan across from us, eyes glazed over from her release. She seemed to be staring at Megan’s butt, or maybe between our legs, where Megan’s wet pussy was moving lazily across my dick.

I pushed Kate off me and walked over to where Megan was sitting. I could feel her eyes on my cock, which was still partially hard and swung back and forth while I walked.

“Hey,” she said.

I bent down, kissed her, and slowly moved my hand into her pants. I casually slid two fingers inside of her; she was still soaking wet. We stayed like that for a minute, my fingers curled inside her so that I held her pussy between my fingers and my palm. She looked up at me expectantly. Kate had followed me over, and was hugging me now from behind.

“I’m tired,” I said. “Maybe we should go to Kate’s room and lie down?” Megan nodded, and together we went to Kate’s room, too tired and drunk to do anything besides fall asleep.

***

That’s all I’ve written down for now. If I have time, maybe I can expand more in the future!

Source: reddit.com/r/gonewildstories/comments/vt9usa/the_most_embarrassing_thing_i_did_in_college_mff