Note: Although this happened six years ago, I know that the dialogue is accurate because most of this story is copy/pasted from the email I wrote to my husband the day after it happened. Part of our agreement was that I had to give him details of everything I did with Scott. I never thought I’d be sharing this with the internet, but here we are!
[Here’s Part 1!](https://www.reddit.com/r/gonewildstories/comments/gwpyvy/twoweek_fling_with_myf_roommatem_part_1_the/?utm_source=share&utm_medium=ios_app&utm_name=iossmf)
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Scott and I were both busy on Sunday, so we didn’t get a chance to talk about what had transpired on Saturday night. On Monday, he went to work and I went to school; I was a TA in addition to taking my own classes, so I spent most of my time on campus. When I got home Monday evening, I made some dinner and watched TV with three of my roommates, including Scott. We deliberately waited for everyone else to leave so that we could have a moment alone. After one of our roommates had gone to bed and the others had left for their night shifts, I curled up next to Scott on the couch, and he walked me through all of the conversations we normally have as best friends: “Are you okay? John will be home soon, that’s good! Everything good? You seem like you’re thinking really hard about something. Wanna talk about it?”
I was being so awkward and shy, because I really wasn’t sure if he would be down for round two. So when he tentatively asked, “What are you thinking about?” I just said, “Oh, you know what I’m thinking about.”
BAM. Suddenly his lips were on mine and he was clearly taking my advice about politeness; no longer were his hands hovering over my back. They were squeezing, exploring, playing with my hair. His kissing was great; not too aggressive or sloppy, and with just the right amount of gently biting my bottom lip. Saturday’s makeout session was pleasant, but this one was hot. I paused for a moment to say, “Yeah, this is better.”
His hands moved to my tits, feeling them through the t-shirt I was wearing. I decided to make a move. “Is this okay?” I asked as I climbed onto his lap, straddling him. He assured me that it was, and we continued making out intensely. I could feel his boner grow under my crotch. He looked a little embarrassed for a moment, so I grinded my pelvis into his: four layers of clothing separating our most sensitive parts. Realizing that I was completely okay with this, he began making small thrusts as we made out, and he allowed his hands to explore my body over my clothes.
“Don’t freak out. It’s just gonna be one shirt. I’m wearing layers,” I said. I pulled off the t-shirt, revealing a white tank top that barely concealed my black bra.
He was not at all freaked out.
Instantly, his hands went to my boobs, and he could now see my cleavage at eye level. He played with them for a while, then went back to making out with me. He moved his mouth down my neck, making me moan slightly. But when he reached my clavicle, he began moving back up toward my mouth. “It’s fine,” I told him. “Keep going.” He didn’t need to be told twice, and before I knew it, his face was in my DDDs, his hips still grinding his bulge into my crotch.
“You know there’s no possible future where we don’t bang, right?” I asked. He laughed and said, “I wouldn’t be surprised.”
Around this time, my hips were very unhappy with the straddling position I was in, so I asked if we could lay down on the couch. He agreed, and we laid side by side and began making out again- gently, at first, but then progressively harder. His hands moved to my ass and then my tits. He kissed my neck and worked his way down my boobs again, this time pulling back my tank top to reveal my bra. I watched him calculate his next move. Deciding to just go for it, he pulled down my bra to reveal my nipple, and began kissing and sucking on my exposed tits.
At this point, I was dripping wet. I knew that most of his experience with women was pretty one-sided; he was known to be generous in getting girls off, but he was rarely on the recieving end of pleasure. My hand moved to his noticeable boner. “Is this okay?” I asked as my hand rested on his thigh. He nodded quickly, and I grabbed his dick over his shorts, rubbing it gently.
His dick was a bit smaller than my husband’s, but I couldn’t tell many details about it while we were clothed. He was clearly turned on by the over-the-pants handjob, and I had to admit I was having a good time. As he continued kissing my neck and tits, I lifted his shirt up to expose the waistband of his shorts. I played with the elastic for a moment, slipping a finger under the band. I looked at Scott to confirm that this was what he wanted. “Go for it,” he said. I reached my hand down his pants and grabbed his cock, smirking at the look of ecstasy on his face. I began jacking him off while laying on the couch. He continued playing with my tits, rolling my nipples between his fingers and burying his face in my cleavage. It was the start of something beautiful.
From upstairs, we heard the sound of a video playing on our roommate’s computer. Someone was definitely still awake. We looked at each other and tried to muffler our laughter; this was not exactly something we wanted the other roommates to know about. And in any case, things were getting pretty intense.
“Wanna go in the basement?” I asked. It seemed more private, and we wouldn’t have to risk breaking House Rule Number Three: No Cum on the Couch. “Let’s go,” he said. As we got up to leave, I checked my phone. John had texted me: “How’s it going?” I replied with “…I’m slightly busy training Scott. Tell you about it later.”
And we headed to the basement.
Source: reddit.com/r/gonewildstories/comments/gwtmrd/twoweek_fling_with_myf_roommatem_part_2_titties
So hot! Can’t wait for the rest lol