This is Story # 41 of my series about my post-marital sexual journey. It is tangentially related to a prior series - "Coaching a College Grad," but reading that series is not necessary.
If you want any background on me and how I got here, you can read the very first story I published (Babysitter Lauren) or my author's profile. You may also see references to prior stories/people, but for the most part each story stands on its own.
Not everyone likes me or my stories. That's OK. My style isn't everyone's cup of tea.
I enjoy all comments.
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Rose
A little backstory on this one, for those that may not have read the "Coaching a College Grad" series.
A girl named Ally was the oldest of three daughters of one of my best friends. I knew the family very well and we had spent a lot of time together in their backyard pool, vacationing together, etc. when the kids were younger. Ally has a younger sister, Rose, who is two years younger than her, and yet another younger sibling, Penny, two years younger than Rose.
I started fucking Ally when she was 22 and had graduated college and moved home for the summer, leaving her new (and first serious) boyfriend several hundred miles away. She had always had a crush on me, and after she graduated, she came to me for help with sex. She was very inexperienced and naïve and wanted an older man to teach her so that she could properly please her boyfriend.
I fucked Ally for about three months, showing her every trick in the book, then she moved cross country to a new job.
At the time, her sister Rose would have been 20 and in her sophomore year of college.
Fast forward now two years later.
The back deck of my townhouse overlooks a small woodsy park area behind my development, and the park has a walking trail with some exercise stations. One of the stations, a flat bench with bars to hold your feet for sit-ups, is very near my deck and I can usually see whomever happens to be using it.
One Friday evening in late spring as the sun was going down, I had finished a run and was out on the deck cooling down. Looking into the park, I saw a shapely figure stretching, then doing sit-ups on the exercise bench. I could see she had a great head of orange-reddish hair, tied back in a ponytail, and a nice body with a BIG, round ass. I had a feeling I knew who it was, and I wanted to get a closer look. Since I had just finished an evening run, I ran down the deck stairs and onto the path, as if I was just finishing up my own workout.
As I passed the ginger on the sit-up bench, I recognized her as Rose, Ally's younger sister.
I quickly stopped and said "Hey Rosie!"
She looked up from her position on the bench (kind of eye level with my crotch) and immediately recognized me.
"Oh Hey Mr. G!" she replied. "What brings you out here?"
"I might ask you the same, I live right over there, but you're a few miles from home."
Like Ally two years before, Rose was now a recent college grad, and living with her parents until medical school started. I had seen her at her parents' house just a few weeks prior when I was over for some drinks by the pool.
Rose had been a field hockey player in high school and the first two years of college, but she gave it up to focus on her studies. She was taking some time off after college to work and save some money, then she was off to medical school.
Rose was really smart and very mature for her age, and if you didn't know better, upon meeting her in a social situation, you'd have guessed she was a doctor already, she was that mature, well-spoken and professional. I had known her since she was a toddler, however, so around me she was much more casual.
She pulled herself into a sitting position and said "Yeah, but I need the workout. This is gonna be my new workout routine. Run two miles from home to here, do the workout stations, then run home. College made me soft!"
"Well," I responded, "I wouldn't go that far. You look great to me."
Rose gave me a sideways look, and I wondered in that moment whether she knew about me and her big sister. Ally swore she had only told her friend Taylor, but who knows what sisters talk about.
I knew Rose was VERY close with her mother, and that she and Ally had battled each other in a pretty fierce, heated sibling rivalry their whole lives, so I can't imagine that Ally had confided in Rose that she was fucking their dad's friend. If she had, then any sibling fight between them could result in Rose spilling the beans, and make my life a nightmare having to face their father.
Still, the look she gave me was curious, and I wondered what it meant.
I would soon find out.
"Well thanks," she said, "I appreciate the compliment. I feel like I'm in pretty good shape, but this big butt of mine needs some work."
"Rose, at the risk of being really inappropriate, I wouldn't change a thing. Your butt doesn't need any work; it's fantastic."
"You think so huh?"
I saw a sparkle in her eyes, and something else.
She continued, "Well tell me, what are you thinking about when you look at it?"
Rose stood up, turned around and gave me a good look at her ass in tight yoga pants. She bent forward slightly and stuck it out toward me. It was heavenly.
I was surprised at the direction this was going, and how quickly. When I came to get a closer look five minutes ago, I wasn't planning that it might get sexual (although you never know right?). I just wanted to sneak a peek.
"Rose," I said. "I'm thirty years older than you."
"I know. I'm just asking a simple question. What do you think about when you see a nice ass on a woman, any woman? Do think about how it looks when she's sitting in a beach chair or on a couch?"
"Well, no, of course not."
She turned to face me again.
"Well what then? Let me guess - I'll bet you think about how it would look if you were fucking her from behind, how it bounces when you thrust in and out of her."
I was starting to blush.
