Sure - it happens.
That being said, there was one time in particular that I think that the Zity-sphere might appreciate.
I went to college after serving in the Marines, so as a result, I was a good bit older than most students. One rule that my little liberal arts college had was that all first year students must live in the dorms. Not sure how, but through the wisdom of the office of the dean of students, I was paired with a roommate that didn't really make sense. I was 24 year old Marine combat veteran from a dirt poor podunk farming town, and my roommate,
"Bobby" (that would be Robert B. Dickhead the IV) was a generational legacy (the library was named for his great grandfather, Robert B Dickhead Sr.).
Anyway, 18 year-old Bobby was at school primarily to get laid (and party), since he was guaranteed admittance to law school and the partner track at "Dickhead, Dickhead, and Dickhead, Esq." Since I was the first in my family to ever go to college, I was there to study (yeah, and get laid too - but primarily to study). We had a deal worked out that a rubber band on the doorknob meant that there was a young lady in the room and the other one of us needed to crash elsewhere. Bobby had a couple of hook-ups before settling with "Angie." Angie was the brunette-haired daughter of a long line of Southern Baptist preachers, and was typically rebellious. On the outside, she was Miss Goody-Church-Girl-Pillar-of-the-Community. But at her core, she was a horny beast with quite an appetite and little shame.
Our dorm room was fairly small, and each bed was on a wooden loft frame about six-and-a-half feet off the floor. Under each loft bed was a small desk, desk chair, and closet. The rest of the room consisted of a sink and a small two-person futon. Community bathroom was down the hall. As you came into the dorm room, the two loft beds were on the left and right, and the futon straight ahead. Each loft bed had curtains hanging from a rod just below the ceiling to just below the mattress to give a modicum of privacy.
Anyway, one night I come back from the library about midnight and there is the tale-tell rubber band on the doorknob. So I just take may shit down to the lounge down the hall and stretch out on the couch to rack out. My first class is at 9:00 the next morning, and Bobby's first class is at 8:00, so I figure they'd both be out prior to 8:00 and I'd have plenty of time to change, eat breakfast, and get a shower before class. But when I headed back to the room in the morning (I don't know, around 7?) the rubber band was still on the door, and I could hear heavy breathing inside, so I went to breakfast in the clothes I had slept in. Coming back to the dorm a couple of minutes before 8:00 I saw Bobby hoofing it out the door of the dorm and headed off class. I got to our room and the rubber band was still on the doorknob, but having seen Bobby I knew the room was empty and figured he had been running late and hadn't taken it off. So I went in, closed the door, threw my books on the desk under my loft bed figuring I'd grab a shower and get ready for my class. So I stripped down and grabbed my towel, but instead of heading to the shower, I figured I'd rub one out first. So I threw my towel down on the futon, grabbed some lotion and a cum rag, and sat down on my towel and got down to business.
I don't remember how long it lasted or anything, but when I finished, before I could even begin to catch my breath, a female voice said "Well, that looked like it was fun!" (I remember the conversation very clearly)
My reaction was, of course "WTF!"
I looked up and Angie had pulled the curtain around Bobby's bed back and had a bird's eye view. With a big smile on her face she said "Don't be embarrassed! I think I enjoyed that almost as much as you did!"
I stood up and wrapped the towel around my waist and said "Well, show's over. I'm going to go take a shower."
As I was leaving she laughed and said "What, no encore?"
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I should add that Bobby and Angie were together most of that school year, and she and I got to know each other pretty well. After a month or so, many inhibitions had been lost - and I spent fewer nights on the couch in the lounge. I should note, that since this was a small church based school, male students had to be signed in and out of the female dorms, and had to be escorted as well. There were, strangely enough, no such regulations in the male dorms.
When I get time, I'll write a blog post about Angie. She and Bobby had a nasty break-up and she and I spent some time together a couple of years later. When I write that blog post, I'll like to it here.