I probably ought to feel worse about what we did to Jim Boomer, or rather, what we had him do to us, that last term at university, but when I start thinking back about that strange, singular semester, I just can't get around to feeling much remorse. On at least one level, he brought it all on himself.
Lenny and I, old high school jerk-off buddies, had reunited as roommates for our final year at the University of New Hampshire. We had had miserable fortune in the love department that fall semester. Each of our girlfriends had broken up with us, and spring term had started cold and dismal, with no particular prospects for the rest of the semester.
We were out that first Friday night in February to the Blue Boar in town, trying to talk up a pair of handsome college wenches we'd found there. Just when we each thought we were on the verge of bringing home some soft, warm female companionship for the evening, a couple of other bucks showed up that the girls I guess already knew, and we watched our chances disintegrate when the four of them left together, dismissing us rather unceremoniously I thought, after the evenings-long attention we had lavished upon the two girls.
Back at Greenwood High School, Lenny had always been the instigator, the "bad boy" the girls wanted, while I was the "nice guy" who they confided in when there were problems and they needed a sympathetic ear. There were times when I would end up with his cast-offs, so I got some residual sexual excitement as wingman that I might not have encountered otherwise, but it often felt distinctly unsatisfying to be the honorable one of the two of us.
A lot of the girls seemed happy to "talk" to me but wanted, or at least were willing, to fuck Lenny. I wasn't as big or tall as him, but I thought my appearance was fine enough, my body trim with strong legs and a nice ass, all of that, but it didn't seem to translate well into the love arena.
Lenny was a big guy, large bones and dark hair, with sharp steely eyes always looking for sex, and his cock had gotten plenty of action during our high school years, much more than mine.
None of this mattered that cold dismal Friday night, we were just a couple of single, out-of-sorts, sexually frustrated guys, on our way home from the pub.
Lenny was pissing and moaning the whole way, our boots crunching in the snow, complaining about Caroline, his former girlfriend, and how rudely and illogically she had ditched him, how his mighty penis hadn't had any attention except from his own hands for weeks, and our general bad luck that evening.
We pulled up the old creaky wooden stairs of Lennox House quietly, since it was almost midnight, and at least some of the other residents were likely already asleep. We had a three-room set-up on the top floor of what had once been a frat-house. Lenny and I had the largest room as seniors, Ron and Carlos in another, and the other senior Jim Boomer, or Jimbo as he was known, in the smallest room, but a single.
On the way to the loo Lenny paused in front of Jim's door. He looked puzzled for a moment and then smiled at me.
"Listen," he whispered, "I think Jimbo's having a bit of fun with himself."
There was no chance anyone else was in there with him, the guy was a hermit and a nerd to boot. Sure enough, there were some low moaning sounds coming from his room, and a dim light was visible from underneath the door.
"Poor guy is probably as horny as us," Lenny grunted and then got a funny look on his face. He put his eye to the keyhole and started smirking.
"Got a whole scene going for himself in there," he leered. "Probably too worked up to have heard us come in."
I took a peek and got a partial view of Jim lying on his bed and pulling on his penis.
Ha! This was amusing.
Lenny cocked his head and gave me an evil grin. "Game for some fun?" he asked.
There would have been no point in debating, since it looked like Lenny was up for something whether I agreed or not, so I shrugged and said "Sure."
Lenny stood for a moment in front of the door, quietly testing whether the door knob would turn or not, then gave a knock and quickly pushed the door open.
I almost laughed at the sight that greeted us but kept a straight face.
Jim was sprawled out on his back in bed, completely naked, a candle on the bedside table next to him casting a romantic little glow, and he had both hands wrapped around a prick that looked pretty much within half a minute or so of ejaculation.
Lenny paused dramatically. "Oh sorry Jimbo, I saw your light on and we were going to ask if you had any beer around. We're plumb out in our room." He gestured down the hallway.
Jim tried as fast as he could to pull a sheet around himself but the image was just too funny for Lenny and me -- both of us started laughing. Even with the sheet around his midsection, you could see Jim's throbbing prick outlined through the fabric, and a minute later you could even see a wet spot where his damp-at-the-head cock had been in contact with the sheets.
"It's okay, it's okay," Lenny went on as Jimbo fumbled around. "You're among friends. You get a hard one, what you gonna do if no one is around to help out?"
Lenny was trying to display empathy, but his words came out exaggerated, mocking.
Lenny couldn't keep up a straight face though. "But your cock sure looks like it's ready for its Mt. Vesuvius thing!" and he doubled over again.
Jim's face had gone bright red. "Hey look you guys, you should have knocked first," he protested.
"Well, we did," rejoined Lenny, but then added a "Sorry, sorry," which he choked out amid his laughter, holding his hands up.
"Hey look, don't say nothing about this, okay?" Jim's face looked really pathetic. "This is my last semester, I had some academic issues last year and if anything looks bad my scholarship might be in jeopardy and my folks would have a fit." Jim had come from upstate and while he made a decent suite-mate, was nothing special.
Jim studied hard, was not all that social, actually was a pretty boring guy, maybe only one girlfriend the whole time at university. He was middle height, clean-shaven, slender, dark hair. His prick was larger than I might have thought, but I had never seen him with a hard-on before. And of course sometimes these skinny guys look like they have bigger dicks anyway, one of those proportion things, I guess.
Lenny was still chuckling. "No, no, we wouldn't say nothing, would we Rob?"
He reached over and pulled the covers off of Jim, whose prick bobbed stiffly as the sheet was yanked away. "Lennox House pervert caught abusing himself! Good Catholic boy goes bad! Excommunication! Expulsion!"
