This is Story # 44 of my series about my post-marital sexual journey.
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 writing style, and my sexual style, isn't everyone's cup of tea.
I enjoy all comments.
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Wednesday and Thursday
I've mentioned in previous stories that I hang out socially on occasion with a group of about 5-6 couples who have kids in the same social and sports circles as my kids. That is the "in-town group," but of course, my kids have other friends outside of these kids, including some in nearby towns as well. And naturally I've gotten to know those parents over the years too.
One such parent is Wendy, who is a year younger than me. Wendy and I actually grew up in the same town, fifty or so miles from where we lived at this time, and we had been pretty close friends in our youth. We hooked up twice when we were younger, much younger, but only to the extent of kissing. We were just inexperienced teenagers.
After high school, we went our separate ways and lost touch, not having the benefit of social media back then.
Twenty years later, I was shocked to randomly see her at a local preschool when I was dropping off my youngest. Wendy and I hugged like long lost friends, and spent some time getting caught up over coffee after drop off.
Wendy told me how they had just moved cross country to a neighboring community due to her husband's job. She had enrolled her young daughter in the same pre-school that my youngest daughter was going to.
Wendy had five kids - four older sons, and the aforementioned daughter who was the same age as my youngest daughter. The two became friends at pre-school, and remained friends even though they ended up in different districts when they were old enough for regular school. As such, we often saw Wendy and her husband Mike when we dropped off or picked up for playdates and sleepovers and such over the years.
Although we didn't hang out socially very much because they weren't in any sports or other groups together, and we didn't live in the same town, both my wife Caitlin (at the time) and I really liked Wendy and her husband and we had had drinks with them on several occasions. It never came up that Wendy and I had hooked up a million years ago. No one knew, and it was never mentioned between us. A complete non-issue.
Wendy was a good source of friendship to me as Caitlin and I went through our divorce. I never mentioned any of my relationships with the babysitters while I was still married. Wendy and Mike were very religious and straight-laced, and I believed she would judge that kind of thing poorly, maybe even end the friendship.
Nor did I tell her much about my escapades after splitting with Caitlin, for the same reason. She'd likely view my actions poorly, especially with some of the married women, or the much younger women. And I suspected also that some of the types of sexual activity that took place - throat fucking and anal and the name calling etc. - wouldn't be her cup of tea either. So, I never really brought it up with her other than casually mentioning that I might be seeing someone.
After my oldest went to college, my youngest was still at home, and so was Wendy's daughter. With the Columbus Day holiday coming up and our school district on Fall break, the weather looked perfect, so I asked my daughter if she wanted to hit the beach for the weekend. She said yes, but could she bring a friend, and named Wendy's daughter.
I reached out to Wendy and her husband via group text, gave them my idea, and they said sure, their daughter could go, but if it was no trouble, they'd love to join us too. A quick internet search and we found a house on the beach about two hours away, for five nights, leaving on Wednesday afternoon and coming back Monday, which was a holiday.
We drove down separately -- Mike with Wendy in their vehicle and me with the two kids in mine so they could ride together. I had a big SUV with plenty of space, more than enough for all five of us really.
About half way into the drive, Wendy called me from her vehicle, saying that Mike had gotten a call and needed to turn right around and get back to work, something about a deal they had been working on for months was about to fall through. So, we found a convenient place to pull over, and Wendy jumped into my car with her bag. Mike thanked me with promises to come down for at least part of the weekend if he could fix the problem. He shoved about a thousand bucks cash into my hand as he shook it and sped back toward home.
An hour later and we pulled into our rental house in a quiet community near Virginia Beach. Since it was off season, we got a huge house for just a few bucks, big pool and hot tub and more bedrooms by far than we needed. I grabbed the top-level master bedroom with king bed and walk in shower, Wendy grabbed a similar room on the mid-level, and the kids grabbed the room on the bottom level so they could have privacy to make their videos and take their selfies. That level had its own large bathroom and even a small second kitchen, so I didn't really expect to see much of them since they were old enough to care for themselves.
The kids flung their stuff into the room, explored the rest of the house, then set off for the beach, just across the street. Wendy and I unpacked our respective stuff, then unloaded the coolers and shopping bags of the stuff we brought with us, making a list of what else we'd need. We the set off for the grocery store together to grab the missing items.
Two hours later we were back and unloaded the goodies. We could see on our GPS trackers that the kids were still at the beach, and since it was now late-afternoon, I declared that it was happy hour. Wendy agreed, so we poured some wine and sat on the deck looking at the ocean, just talking and enjoying each other's company.
It was all very easy with Wendy. We knew each other as kids, were strangers for twenty plus years, then became friends again over the prior fifteen years. Our conversation flowed very easily and naturally.
The kids came back about 5:00, hungry, so I threw some steaks on the grill while Wendy and the girls threw together some sides. We ate on the back deck as the sun started to set, then cleaned up and ran out for ice cream. Anyone watching us would have thought we were a family.
We got back to the house, and the kids wanted to take the car and go to the boardwalk. Wendy's daughter had just gotten her license, while mine was still on her permit. We asked them to be back by 8:30, and then we negotiated 9:00.
They left, and Wendy and I grabbed another bottle of wine and walked up to the beach to catch the last of the daylight. We sat on two chairs and just silently looked out at the ocean, watching the waves. Very little was said, we were quite content with the sound of the ocean.
As the last of the daylight left us, Wendy reached over to me and took hold of my hand, which obviously surprised me. There was no denying our connection, but she and Mike seemed very happy and I never considered making any kind of move on her. We sat there silently holding hands, and as the darkness fell, she leaned over and kissed me. A sensuous kiss that flooded my memory back to my youth.
Our kiss lasted a full minute or more, after which we pulled away from each other and silently folded our chairs and grabbed our empties. We held hands walking back to the house, again in silence.
As we stowed the chairs away in the closet on the ground floor, Wendy said, "you wanna have one more on the deck?"
"Sure," I said. "I brought some scotch, could you pour me one over ice? I'm gonna hop in this outdoor shower here and rinse off. I love outdoor showers."
"Sure thing," she said, and started walking up the stairs. I took a good look at her round ass walking up the stairs, and she glanced back and caught me looking.
"Was there something else you wanted, or needed?"
"Oh," I said, trying to play it cool. "I have no towel here, could you just throw one down from the deck off my room. It should land here pretty close to the shower."
"You got it," she replied with a wink.
I peeled my clothes off and jumped into the shower, which I had stocked with soap and shampoo earlier in the day. It was dark now, about 8:00, and I could see that we were pretty much alone down here -- there were no lights on in any of the houses around us.
As I washed, I thought about Wendy, the kiss, and what it could possibly mean for the rest of the weekend. My dick was starting to stir at the thoughts, and I began to harden. I finished my shower and opened the door to look for the towel that (hopefully) Wendy had thrown down. What I found instead was Wendy herself, naked but wrapped in a towel, and holding a towel for me.
She said, "An outdoor shower sounds great," as she slid past me and into the stall while she handed me my towel, taking a quick peek down at my cock.
As she closed the door to the shower, leaving me outside, naked, wet and speechless, she dropped her towel, giving me a split-second glimpse of her naked body.
"See you on the deck," she said as the water started running.
I ran up the deck stairs, processing what was happening. Is she teasing me and just having fun (which would be terribly cruel), or was this leading to more? Are she and Mike secret swingers, or is the marriage in trouble and she's looking for some affection? All great mysteries.
I was also thinking about what I had seen. Obviously, I knew she had a great body, but seeing her naked was so much better. In her early 50s with five kids, she looked fantastic, you'd never guess her age or how many kids she had. Her tits weren't overly large, but they were a nice size and firm, with very little sag.
I threw on some shorts and a t-shirt, and found our drinks on the back deck overlooking some empty houses. As I sipped and pondered the future, she appeared about five minutes later, similarly dressed and obviously braless, and sat down next to me with her wine.
We sipped and held hands again. It was a warm night, approaching 8:30 pm. I checked the kids' location and they were still on the boardwalk, which was about a ten-minute drive.
As if reading my mind, Wendy said, "where are they?"
"Boardwalk still," I said. "Walking towards the car, almost there. Probably home in fifteen minutes."
Wendy set her drink down and stood up, stood in front of me and leaned down to give me another deep kiss. I reached into her shirt and felt her firm tits and hard nipples. She allowed me to do this for a minute, then moved my hands and dropped to her knees in front of me.
Reaching for my waistband, she gripped it and pulled my shorts down. I lifted my hips, and she pulled them all the way off. My cock was already hard from the kissing and fondling. Hell, it had been hard since the shower! It slapped against my stomach when it was released.
Wendy gasped when she saw it, and said "Holy Crap!"
She gripped my cock and squeezed it tight, silently stroking and squeezing my cock, fondling my balls with the other hand. My precum was flowing steadily, as it always does, and she rubbed her palm on the head of my cock to gather some, then used it as lube to continue jacking me off.
"I can't believe how big you are. And the tip is even bigger still. It's huge!"
Faster and harder she jerked me, my hips lifting off the deck chair with each down stroke. I was waiting for her to suck me or tit fuck me or climb on top of me and fuck me, but she just kept jerking me off. Finally, I stiffened, but didn't say a word, and my cum shot forth, blasting up into the air and landing on us like rain. She giggled as the cum storm petered out, and we were left covered in my spunk.
"Holy Shit," she said. "You must have been backed up!"
"A little maybe," I said. "But that's about right for me."
She stood and said, "I'll try to remember that," and ran into the house for some napkins to get me cleaned up.
A minute after I put my shorts back on, the girls pulled into the driveway.
The kids told us about their night on the boardwalk, stressing how safe it was and asking if they could stay later on other nights. We saved the conversation for the morning and Wendy and I retired to our rooms while the kids went to their room for the night.
I tried to fall asleep as I pondered the night's earlier events.
My phone buzzing startled me -- a text from Wendy.
Her: "Hey, can't sleep."
Me: "Me either. How come?"
