This is a story that started about six months ago. At the time, I didn't think I'd be proud of it, but now, I'm pretty fucking proud of it.
At the time I was 27 and single. My sex life has been fairly active the better part of the last decade, but about six months ago it changed rapidly. It had been something like a month since my last sexual encounter. That had been in January.
One day in February, my sister - Brittany - invited me to her apartment for a game night with some friends. We're fraternal twins, so we grew up fairly close and shared a lot of the same friends. I don't remember what the game was that particular night. We'd played several times before, usually with a fairly consistent group.
On this particular occasion, Brittany's roommate, Kelsey, had joined us. Unlike the rest of the group, we didn't grow up with Kelsey. She and my sister had met in college but became fast friends. Honestly, I'd always had an eye for her, but at the time we lived in different cities and I never thought much of it.
After college, she and Brittany decided to keep living together. Some time after graduation, I had moved into the same city for work. It was good to have some people I knew in my new town, even if one of them was my bitchy sister. (I say that semi-jokingly. She's not really that bitchy, it's just part of a persona she puts on.)
Whatever the game was that night, I ended up paired with Kelsey. No problem, I thought. She was wearing a white tank top, clearly with no bra. Odd choice for February, but since we were at her apartment I guess it wasn't too strange. I figured if I played my cards right (no pun intended) I could get a couple good looks in.
Our game had been going a while when I got a text from my sister. "Want me to turn the temperature down?"
I was confused for a minute and sent a simple "?".
"So her nipples will get hard," read the response.
Obviously I had gotten caught staring at Kelsey's chest. But, honestly, it was hard not to. I go crazy over small tits and Kelsey's are that perfect blend of small, yet perky. The way she leaned across me to draw cards, it was hard to believe that on some level she wasn't putting on a show.
(Have you guessed who I'm going to fuck, yet?)
But nothing happened that evening. I went back to my own place, still a relatively empty space since I'd just moved in back in November. The next few days were completely uneventful, although from time-to-time, a nice visual of Kelsey slightly leaning over me came back to mind.
One night, I was scrolling through Instagram and happened to see a photo Kelsey had posted. It wasn't anything overtly sexual. Not even a bikini throwback, but something about her smile got to me. I liked it and moved on.
A few minutes later, my phone dinged. I was surprised to see an Instagram message from Kelsey. Just a smile emoji, but I took the bait. I sent a smile back. A few more minutes went by and Kelsey responded with a "What are you up to?"
We talked off-and-on the rest of the evening, never much more than just a little flirting. I didn't expect it to go anywhere, so I honestly didn't put a lot of effort into it.
A week later, the group got together again for another friend's birthday. We were meeting up at a restaurant for lunch and I arrived a couple minutes early. Brittany and Kelsey came together.
When they got out of Brittany's car, Kelsey took an awkwardly long look at me. I didn't think much of it at the time, and she went in to put our group on the waiting list.
While she was inside, Brittany looked over at me. "You'd better not fuck her."
"Um, excuse me?"
"I know she's into you. But she's my first roommate I haven't absolutely hated. You can't mess this up for me."
"Whatever."
Kelsey came back and not much more was said about Brittany's threat.
When we sat at the table, Kelsey sat next to me. I don't think it was on purpose, but it definitely altered the course of events.
Shortly before our group finished, Kelsey leaned over to me. "Did she give you the same warning she gave me?"
"Yeah, she did."
"Want to really piss her off?"
Fuck.
At that point our group left the table and moved outside. I went back up to Kelsey. "You would seriously do that just to piss off your roommate?"
"I mean, I wanted to do it before. But now I know you do, too."
She had me there. After that night of cards there had been several occasions where I remembered her perfect tits, those small breasts I imagined were barely a handful.
"So, how do you propose we do this?"
"Give me your address and I'll meet you there. Tonight."
I didn't take much convincing.
That afternoon, I went back to whatever I'd had planned. I made sure to get home a little earlier than usual. I grabbed a quick shower and put on a shirt. I started to grab some boxer briefs, but realized a bit too late that I hadn't done laundry in longer than I care to admit.
Who cares? I thought. I was going to be taking them off in a few minutes, anyway, so I just didn't bother.
I sat on my couch and got my phone out. There was a text from Kelsey: "going to be a couple minutes late."
Fine, whatever.
I sat on the couch and I'd be lying if I said I didn't stroke my cock a little.
