Author: Illustrious_Weekend

[F]inding Out My High School Sweetheart and her College Roommate Were Dor[M]room Cumsluts

Random story from when I was about 19. My high school sweetheart and I, we were each other’s firsts and stuck it out on-and-off for about two years before we drifted apart. We remained friends for a long time, occasionally had phone sex or jumped into bed for a while, even after she got engaged at 23.

At this point, though, I had thought she was still pretty innocent. We’d swap some sex stories from time to time but I didn’t really keep up on what was going on with her. First time I came to visit her at her college in the midwest, I dropped in to stay with her for a few days as she started her sophomore year. She was a bubbly and sweet blond from a wealthier family, on the curvy side with a pretty face and medium-length hair. I was looking forward to spending some time with her.

Her dorm was an all-girls floor for liberal arts students who wanted to focus on their books instead of partying, but because enforcing it was left up to other college girls, that was more of a tip than a rule. She’d told me she could put me up as long as there were no male voices causing a disturbance after the 8:00 pm curfew, and that her roommate would be there for Friday night, then gone for the rest of the three-day weekend. Read more »

The Ti[M]e I Took My Pro[F]essor’s Virginity and Dumped Her Cold

My last story, as long as it was, seemed to go over OK if the upvotes are any indication, so I thought I’d type up another:

When this happened, I’m about 22, went back to school at a city college part time. It’s my second or third semester and winter is closing in, good old cuffing season. I’m not really socializing with the students much because I don’t have much in common with them, but I get placed in a literature class with this adjunct who’s maybe 26. Slim body, nice legs, brunette of about medium height with one of those milky fair complexions. She laughs easily and dresses well but you can tell she’s pretty bookish and maybe a little bit of a lonely soul.

This is a poor college town and most of the decent girls are tied to the university somehow, so at this time I’m semi-seriously dating another grad student, a history major. This one’s a little curvier than I usually go for but DDD top-heavy and likes to be dominated, so she’s a lot of fun, but she’s getting needy about a commitment, has no real job prospects, and wants to move somewhere I’m definitely not going. It’s running on fumes and I’ve already started hanging out with a townie Puerto Rican MILF on the side who hates her boyfriend, she’s reasonably freaky, looks good hanging around in my t-shirts, and doesn’t ask for much, so whatever happens happens. Read more »

Stretching Out [M]y Housekeeper[F]

Flashback to my mid-20s, I’d settled into my first “real job”, and I was finding my way. In decent shape, tall, and well-hung, I’d made a decision to stay single and have fun.

Kelly had been cleaning my apartment for two years. Maybe 34, she was a tiny thing, cute, about 5’2″, red hair, slim, from one of the country towns in the area, but she would often talk about her past working with musicians in Los Angeles and Las Vegas. She’d partied and had a couple of interesting tattoos to show for it, but now she’d calmed down, was close to her family, and did some art on the side. I always liked hiring her because she did a good job, had a good attitude, and showed up on time, and we’d gotten to be chatty about life. Once, when she had a sick pet at the vet, I slipped her an extra $50. That was the only time she’d hugged me, told me I was “amazing”. Beyond that, I didn’t give it much thought. Read more »