(All persons involved in sexual activity are over 18 years old and any similarities between this story and real life are purely coincidental)
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After being divorced for 10 years, and my only daughter all grown up and out of the house, it was time to get serious about dating and not just hooking up with people here and there. I signed up for an online dating site and met a very nice woman, Diana.
Diana had been a widow for about 5 years and was ready to start dating again. She worked as a pharmacist and as a well-tenured employee, she had a lot of vacation time to use. Her freedom from work, and the fact that her daughter was moved out of the house and her son, Timmy was now entering high school, meant she had a good deal of time available for us to hang out together. I had retired from a career in federal law enforcement and my new, part-time consulting gig was a perfect fit for her ability to take time off. We filled our dates with activities from the long list of things we both loved to do; golfing, cooking, wine tasting, hiking, traveling, attending concerts, and just about everything else.
Diana was slightly younger than me and kept herself in excellent shape, sporting a hot little body. The first time we made love was incredible. It was our fourth date. We went golfing in the morning and then grabbed some picnic food and wine and headed to a big county park for the afternoon. We set out on some hiking trails in the park and, Diana sharing my sense of adventure, we detoured off the trail to a secluded spot hear a small stream. After eating, the large, thick blanket we brought to picnic on became our bed.
Casual kissing turned into some touching and, mixed with the wine we’d had, lowered any inhibitions she had about getting naked out in the wild. Her shirt and sports bra came off first, quickly followed by her shorts. As I ran my hand down under her panties and started to tickle her wet clit, she tugged at my belt in an effort to get my shorts off. With very little effort, she pulled them off and exposed my hard cock protruding from the opening in my boxers. My fingering her pussy continued while she stroked my dick.
After a few minutes of foreplay, Diana announced, “John, I hate to tell you this, but I could still be fertile.”
“Lucky for us, my vasectomy 15 years ago makes me ready to go,” I replied.
I encouraged her to climb on me and ride my cock she was ready and willing. Perched on my mid-section, her well rounded, 34C tits available to suck on as she lowered herself to me, she took all of me deep inside her. Her orgasm, followed closely by my bursts of hot cum into her womb, were perfectly in rhythm. Our fourth date became the launch pad to a vibrant sex life for us and it was a great addition to all the fun we had together.
After about 4 months, we decided to move in together. I rented out the condo I owned and move into her spacious, Southern-style, ranch home in the suburbs of Columbia, South Carolina. Her home was a favorite place of ours to relax. Barbequing out by the pool and hot tub, playing badminton or chipping golf balls on the huge lawn area, and making love in her enormous master suite were amongst our favorite activities.
Her son, Timmy, and I had always gotten along, but he had his friends and we didn’t spend much time together before I moved in. He was mostly into playing video games, watching science fiction movies, and just about anything that didn’t mean being outside or requiring much physical energy. With his dad having passed away when he was only about 10, Timmy didn’t get a lot of manly attention. He was close to his Uncle Dave, but that guy didn’t have much manly attention to give. After I moved in, I did my best to understand Timmy’s interests, but it was hard.
Besides not sharing Timmy’s interests, he was very well accustomed to being the baby of the family. His sister, 7 years older than he was, always treated him like one of her dolls. His mom, sensitive to what he’d been through when his dad was killed in a car accident, went overboard to make his life comfortable. He didn’t clean up after himself, he didn’t do his own washing, he wouldn’t dream of finding a part-time job to make some fun money, and he went from one meal to the next enjoying whatever snack food he could get his hands on. If you ever wondered what he’d snacked on or where he’d eaten it, you could always find plenty of wrappers and crumbs to answer your questions.
My childhood was the antithesis of his comfortable, happy go lucky, do what feels good and let others carry your weight upbringing. I was raised in a rough and tumble, outdoorsy, sports-minded home by a retired Marine. Lieutenant Colonel Robert Ambrose was my father and I called him Colonel as much as I called him dad. If you think my dad was tough, you never met my mom. I loved my mom and dad and they raised me to be a free-thinking, confident young man. But, my freedom ended when it affected someone else. A very high level of personal responsibility and accountability was ingrained in me from the very beginning.
I got my first job as a dishwasher at a small convention center at 14, bought my first car at 16 with my own money (I loved my old Ford Falcon), and made sure I “left no trace”; a saying that could have easily been on the mantle over my parent’s fireplace. I played every sport I could think of and never missed a homework assignment. I graduated top of my class, received a degree in sociology, and was recruited into Federal law enforcement.
Diana knew her son wasn’t on the right path, often blaming herself for his short-comings, but as I reminded her constantly, eventually a young man has to learn to raise himself into the way he ought to be. I took a wide path around any form of discipline because it wasn’t my place. Timmy and I were pleasant, but it made my blood boil to hear him whine, leave various messes for his mother to clean up, procrastinate his way into B’s and C’s on his report card , and develop a nasty habit of blaming other people for anything he didn’t do well.
When Timmy reached 16 he studied hard for his driver’s test (when it was really something he wanted he put his mind to it) and passed on the first try. He was rewarded with a new car from his grandparents, against the will of his mother, and his freedom increased overnight. Unfortunately, his level of responsibility didn’t keep up. In one of my weaker moments, I called in a favor from a local police chief that I knew, to get Timmy out of facing stiff penalties for getting 3 speeding tickets in a matter of a few months.
Diana and I lived a wonderful life of fun activities and great sex. Living together may have reduced the day-to-day sex, but we got away enough to have some wild times at night on beaches, in various hotels, and even once on a golf course during our round. Diana was around every day to make sure Timmy’s lifestyle didn’t rub up against me too much; the messes he left behind were always tidied up and the teen-cave of his room, complete with a full set of electronic gadgets, gave him a place so he could stay off my turf in the family room.
During Timmy’s junior year in high school, a series of changes took place surrounding our home. Diana got an opportunity to start travelling as a consulting pharmacist; working with other hospitals around the country. I followed along on her trips that allowed me to play a great golf course and enjoyed my mini-vacations, complete with plenty of hotel sex. When I did stay home, my disdain for Timmy’s pigpen lifestyle hit an all-time high. He’d never survive my discipline, probably wetting himself when I opened my mouth, so I either avoided being home or shut up and cleaned up his messes.
Another big change came when Julia came home from school one day with Timmy. Up until now, his general lack of interest in the opposite sex often made me wonder if he was gay or not; something I was fine with, but couldn’t wait to see the reaction of his evangelical grandparents. The jury was still out, but for now, Timmy had a girlfriend. Julia would sit and watch him and his friends play video games, often reading a book quietly, or they would go to a movie or whatever else nerd teens do. She was really cute in a plain, girl-next-door sort of way, and was very shy. We acknowledged each other’s presence, but that was about it. They were cute together and she did ride his ass a little about the mess in his room and how disgusting his car was. It didn’t help.
Figuring she’d get bored of his immature lifestyle, I was surprised when summer came and went and they entered their senior year in high school still together. I never saw them so much as hold hands, but that made Diana more comfortable when we were on the road.
The cute little couple had a reality check when they started talking about college after high school. Timmy was smacked with the news he wasn’t eligible to attend any of the schools he’d dreamed of attending; his hopes of going away and experiencing the freedom of college life were dashed by his lazy lifestyle. Julia was accepted to a plethora of great universities, and chose one in California. Timmy signed up to attend community college.
A few months before his graduation, Diana decided to plan a summer trip to Disney World for his graduation present. Thankfully, I had already made a commitment to be in Europe doing some consulting for the Department of Defense and couldn’t go. I wasn’t sure how I would get over not having the pleasure of standing in 2-hour long lines with a bunch of screaming imps to ride on a backbreaking, jerking ride for two minutes, but I’d figure it out.
The time came for my trip to Berlin and, leaving a few days before they left for Disneyworld, meant I would arrive home before them and have 3 or 4 days of pure bliss to rest up from my European travels. Berlin was great and it got even better when Diana fed my phone with some of the horrific images from Disney World including over-priced fried food, the ever-present kid throwing a temper tantrum, and of course the hotel pool; complete with who knows how much pee from all the little kids bathing in it. Diana was kind enough to slip in a few pics of her getting out of the shower in the morning, too. That made me happy.
I was lounging by our pool one day when my phone buzzed with a rare text from Timmy:
Timmy: Julia needs something she left at our house and is going to call you to come by and get it.
Me: Okay.
Timmy: I gave her your phone number.
Me: No shit sherlock. How else would she call me? (I deleted that text before sending it)
About an hour later, as late afternoon was finally cooling down, my phone rang. “Hello, this is John,” I answered.
“Um, hello. This is Julia, Tim’s friend.”
“Oh right, he said you’d be calling. I guess you left something here?”
“Yes. Is it okay if I come pick it up in an hour or so.”
“Sure. I’ll unlock the front door. Just let yourself in. I’ll probably be in the backyard.”
