Accomplishing a feat I never set out to tackle: Sleeping with three sisters and their mother over the course of nine years [MF] [NOTE: Long story]

Sometimes, sexual feats fall right into your lap without much of an effort. Such was the case when I slept with my high school ex-girlfriends’ mom last week, months after her divorce was finalized.

First, a timeline.

Shortly after my 18th birthday, I began having sex with my then girlfriend, Katie. Katie was a bit on the larger side compared to me, a thin cross country and track athlete at the time. We were sexually active through most of our senior years, and went our separate ways in college.

My sophomore year, I hooked up with Katie’s younger sister, Abby, an incoming freshman. We dated on and off for a year or so, breaking up only to get back together on the weekends here and there.

It wasn’t until 8 years later I hooked up with their youngest sister, Cassie. Now a sophomore in college and nearly 7 years younger than I, Cassie caught my attention on Tinder when she was home for winter break. We messaged back and forth and talked about my time with her sisters before leading me on to a couple of one night stands when she was home. She ended up virtually ghosting me when she went back to college.

About a year and half later brings us to last weekend, scrolling through my phone on a Friday night when their mother, Carol, popped up on my Tinder. The 55-year old, dark brunette trophy of a woman settled her divorce earlier this year, and was now prowling through social media sites looking for company it seemed.

I burned a superlike on her and anxiously waited. Not 30 minutes later, a notification popped up. We matched.

I made an awful attempt at a terribly cheesy pickup line, hoping either she’d be so annoyed by it, it would elicit a response. Or, she’d actually fall for it and we’d move into some conversation. The former was true, as expected.

After chatting about awful pickup lines, we got to talking about memories of me dating her daughters. We got into home lives, he divorce, my lack of stable partners, and my wishes to find someone a little more free to do what we wanted.

I made my move and asked if we could go for some social distanced drinks at a local bar or restaurant. She counted with something even better. “Well since my ex-husband is gone and the kids are out of the house this summer with him and friends, why not come over and let us use the full bar we have here?”

I jumped at the opportunity. “Give me 30 minutes,” I said, halfway in the shower and thinking about what to wear.

Before Carol, I once slept with a 42-year-old woman when I was 20. Now 27, her status as a bonafide MILF at 55 would be the largest age gap for me. But from what I’d seen of her through the years, she aged better and better and kept that same, stout, tight frame with all accentuating accents.

I arrive a bit after 8 p.m. our time to the house I’d spent hours and days at, a decade ago. Not much had changed. The lawn was nicer. The house seemed cleaner. And the mom that never really caught my eye had my full attention. She wore her role perfectly.

Carol answered the door with a message in her eyes. Her long, black hair flowed down to the top of her chest. Her dark brown eyes were as inviting as they were mysterious. They paired so well with her entire look. She wore a flowy, flowery top that didn’t leave much to the imagination about what she was hiding underneath. (I’d later find out she wore 36DD cups).

Her blue jeans seemed worn, but damn-near painted on, with one of the tightest backsides from a woman her age I’d ever seen. I looked her up and down as often as I could. When she’d go to the fridge. Wash her hands. Every angle, every side was a masterpiece. And her I was, some lanky, lean runner looking to score big with my exs’ mom.

The conversation was as easy as she was on the eyes. We laughed, got serious, laughed some more, and drank. After a few glasses of wine, we retreated to the bedroom. I asked to see around the house some more, asked if anything hand changed since 2012. I followed my tour guide right into our final destination: the master bedroom.

She led me in, let me go, then shut the door behind her. The room was massive, but the California King in the middle of the room was only the second focal point to catch my eye. Carol set her fourth glass of wine on the dresser and walked right up to me. At 5-foot-10, we were nearly eye level (I’m 6-foot).

“I’d like to take the lead, if that’s OK,” she said. “There are…certain things I’m looking for. And I’m not sure you’re willing to leave at this point just because I won’t let you be manly man.” She pulled off my belt and unbuttoned my jeans. My erection was more noticeable than the king sized bed she was pushing me back toward.

“I’m alright with whatev–” she stopped me mid-sentence.

“I only want to hear sounds out of you. No talking,” she said, sliding my jeans to my ankles; my boxers going with them.

She went down on me, slowly at first. Taking me in long, intentional strokes with her hands and her mouth. I gathered her hair into a makeshift ponytail and began guiding her. It was as perfect as it could get. Wet, rough, slow, fast, delicate, dedicated. I started to feel better and better with each stroke. Then she stopped.

I kicked off my jeans and pulled off my shirt as she did the same. She donned a lavender bra with matching silk underwear. Those, too, came off nearly instantly as she laid on her back on the bed of throw pillows.

“Here,” she said, guiding my head between her legs. “I’d prefer stimulation over penetration. Until I’m ready.”

It was my turn to go down on her, diving right in. She was maybe 4-5 days post-shave. Not a bush but not completely bare. A nice fuzzy texture against my tongue. I focused on her clit and lips mainly, getting her right to the edge before she had me back off. Finally, she was ready.

“Start with one finger, then go to two and three,” she said, directing me in a holding pattern with the back of my head. She rotated her hips up and my fingers inserted inside her. It took her maybe a minute to reach the peak, and then it hit me. A wall of warmth and wetness came cascading into my mouth. Down my lips and along her thighs. Her moans were short but audible, but when she came, she arched her back and let out a sigh of relief. Her body shook and she let a high pitched squeal out as she came down.

I rolled out her legs and onto my back, laying next to her. She laid there smiling, eyes closed. I ran my hand along her body, cupping her breasts and feeling her abs. She had a noticeable six-pack. Not completely shredded, but pronounced for 55.

She rolled over onto her stomach and asked for a back massage. This was incredibly difficult with my erection and what I was straddling. It didn’t take me long to figure out what she was eluding to, as she arched her butt into my pelvis. I slipped inside her effortlessly as she let out another sigh of relief.

I rode her prone bone for a while, mixing up positions of her legs and mine. I reached underneath her and got her to finish again by stimulating her while inside her. She backed up into doggy, where she did most of the work before riding me.

I didn’t last long once she was on top. She had me hold her hips tight until she wanted to cum again. “Touch me,” she said, panting. “Touch me again like before.”

I rubbed her with my thumb as we both neared completion. Again, the same warmth of fluid I felt on my mouth before, I felt on my legs this time. She shifted back and forth, seemingly with no rhythm this time as she finished. She got off, went down and finished me off inside her mouth. I felt like the load was big, as she didn’t come up for a while as she swallowed it.

She rolled over and then back onto my chest, cuddling with me like she had just given up something about herself she wish she hadn’t. We fell asleep like that.

When I woke in the morning, she had rolled over, naked as she was just hours ago. I cuddled up behind her, my morning erection about as ready as I was the evening prior. She shifted back and giggled. “Ready already? I’m not used to this…”

She trailed off as I entered her again, already wet and ready. We spooned for a while, breathing heavy and grunting a bit. She pulled me out and sat up. “How about we finish up in the shower?” So we did.

Source: reddit.com/r/gonewildstories/comments/i8itt7/accomplishing_a_feat_i_never_set_out_to_tackle