It was 1994. I was just 18 and still in high school at the time on a family vacation down to Florida. We were staying with my “Aunt” Becky and her family at their beach condo. She wasn’t really my aunt, she was my mom’s best friend from childhood and i’d known her my whole life. She practically raised me with my mom. She wasn’t blood, but she was family. She was 36 years old at the time and was an extremely active woman. She ran half marathons and biked and had even been an aerobics instructor in the 80s. She was a fit and attractive woman whose body type had probably done more to inform what I find attractive in a woman. She looked a lot like Lynda Carter, the actress who played Wonder Woman in the 70s. Dark hair, small waist and wide hips, and a huge pair of tits. I’d had a crush on her for as long as I’d been aware of the concept of physical attraction.
Author: Flashy_Insurance_808
The Dad and The Sitter: Taking Her Peach
(For parts 1-3 check my profile)
“We have to use protection” she said with a little frown on her face. It was more of an “i’m sorry” and not a demand. I frowned back. “I haven’t worn a condom since I was your age.” I said back, jokingly but it wasn’t too far from the truth.
My 18 year old sitter was currently informing me of her situation. She had been prescribed antibiotics for 10 days after a dental procedure and her pharmacist had warned her that they may interfere with her birth control. It was a low risk, and the thought of cumming in her tight little pussy with the chance she could get pregnant did give me a little bit of a thrill, i can’t lie, but I understood her concern and promised we would be safe until she was finished with her medication. She thanked me for understanding and promised she’d make it up to me. “How are you planning to do that?” I asked and she said it was a surprise.
The Dad and The Sitter: little black dress
(For part 1 & 2 go to my profile to find them)
We had been fucking for a few weeks. She was leaving school early and I was skipping out on work a couple of times a week so that we’d have 2 hours of alone time together before my kids got out of school. She wasn’t a virgin, but she wasn’t super experienced either. She’d only had sex a handful of times with a senior she went out with last year. They had barely done more than missionary and girl on top and he had always worn a condom. He never ate her out or played with her asshole or shot his cum on her or in her. What a fool. I was determined to turn her into a dirty little fucktoy before she went off to college and I was gonna spend the next 4 months training her how to make an older man happy with her tight little body.
The Dad and the Sitter: playing hooky
(For part 1 go to my profile) *the girl in this story is 18
It had been over a week since the blowjob in the pool house. I hadn’t been able to think about anything since that afternoon. The way her hot young lips felt around my cock. How good her body looked when I took her bikini off. I was getting random erections all day long like a teenage boy. I’ve always had a high sex drive, but she had awakened something primal in me that I hadn’t felt in years. I needed to have her again. I wanted her all the time. Unfortunately I had the ultimate cockblock of all time: two kids. Despite the fact the sitter was at my house four days a week, we had very little success taking the pool house incident much further. Usually the best I could get from her when I was home was a little squeeze of her ass, or her brushing her hand over my crotch, a kiss in the kitchen while the kids played video games in the living room, but nothing more than that. We were texting each other pretty regularly. She was really enjoying sending me pics of her in my bedroom’s bathroom in her underwear. Such a little cocktease. I needed to figure something out soon.
Redheads with big asses are always trouble
It was not typical for me to be out of the house on a weekday night minus the wife and kids, but my friend Brian’s band was playing their first show ,and even tho I had long retired from playing in bands, I was still someone who would support a friend’s new project.
The show was at this new Korean BBQ place that had outdoor seating on a big patio and they had built a stage for live music. Another friend of mine was the manager there and he had booked by buddy’s band the gig. An outdoor patio of a Korean restaurant on a Wednesday night in October was hardly a show at CBGB’s, but when you’re a middle aged punk who had been playing in bands since you were 14, you’ve experienced far worse venues.
The Dad (42) and the sitter (18)
(This is reposted cuz the age of the girl wasn’t specified originally, and I didn’t want it on my main account just in case anyone found it)
When I’d met her, she was just a kid. She was the daughter of one of my wife’s coworkers. We hired her to babysit our children from the time they got home from school until we got home from work. It was 4 days a week (mon-thurs) plus the occasional weekend night when the wife and I went on a date or had a work function. I was typically the first parent home, and so I usually had the most one on one interaction with her. She was a cute girl: tall for her age (almost 5’10”), with long legs, small breasts, a perfect teenaged ass, and just the most beautiful smile. I felt like such a fucking creep. I WAS A FUCKING CREEP.
She and I always had pretty open conversations whenever we had our time alone. She liked talking about her life and I liked listening and reminiscing on my own youth, before I got married and became a middle aged father of 2. Nothing truly inappropriate ever happened between us…not until her senior year. That’s when SHE got a boyfriend and I got VERY jealous.