Author: SexySinWriter

School Board Chair & Vice Chair Tryst, Part One

A few years back I took a role on the school board at my kids school. The school board chair was named Anna, and by my third year (it was a five year term) I was elected as vice-chair.

Obviously the past year has been a challenge for staff, teachers, parents and students. It also meant more intense meetings and more dedicated time to my position.

I had known Anna for the better part of 25 years. The two of us actually attended the same high school, although she was two years younger than me and we rarely ran in the same circles.

I remember some of the guys in her grade talking about how in high school she was known for wearing g-strings. Having said that, she married her high school sweetheart so I always knew she had had minimal partners.

She was an athlete in our younger days. Captain of the volleyball team, really good basketball player and an all-state performer in track & field. Her active lifestyle hasn’t changed, as she’s still a runner and very much the definition of ‘hot’ mom. Read more »

The Accidental Visit to the Glory Hole (M35/F33)

The Accidental Visit to the Glory Hole (M35/F33)

A night in the big city was just what my wife and I needed. The kids with grandparents, a nice hotel room, dinner at a fancy restaurant and us drinking way too much wine.

That’s essentially what it was, and we learned a bit about ourselves on that fateful night eight years ago. The most exciting part? It was all unplanned.

After dinner and some drinks at our favorite pub, we decided to head back to our hotel and try out the hot tub in our room. We ended up making a pit stop.

“Oh my god, there’s Sex World!” my wife exclaimed.

“Should we stop?” I asked.

“Yeah, we can stop,” she answered.

We’ve been to a sex shop or two together, but it was hardly something we did on the regular.

“Maybe you’ll find a new toy,” I commented, as Lisa smiled and rolled her eyes at me.

She had been drinking, and like many, alcohol made her more uninhibited. We browsed the shelves and moved from aisle-to-aisle, sharing laughs and teenage jokes, in the process. Read more »

The MILF Chronicles; My (M27) CrossFit Lover (F39)

Amanda and I make a good team. In more ways than one. But her husband doesn’t need to know that.

She’s my CrossFit partner. A 39-year-old mother to three boys and husband to Ryan. Her goal in starting CrossFit was to get in the best shape of her life before turning 40. Within three months of meeting one another we were fucking each other’s brains out multiple times per week.

I didn’t think she needed CrossFit because she looked just fine. Long, toned legs, a flat stomach and curves to go with her 5’9” frame.

Things were pretty innocent at first. Maybe some flirtatious banter, but nothing over the line. Somewhere, though, the flirting increased. Soon it was texting into sexting. Then, pictures. Oh my, the pictures.

I came to learn Amanda was a little lonely. Her husband was a very successful lawyer but she was neglected. He was busy at work and she was busy toting three young boys to practices, games, appointments, etc. Maybe I was just in the right place at the right time? Read more »

Golf Date (M37/F36)

My husband Brice and I decided to take an afternoon off one day to spend time with one another. Since he always tags along with me shopping and what have you, I thought it was fair when he suggested golfing. After all, he golfs with his buddies at least once a week and I actually enjoy playing too. This time, though, I was eager to make it just a little more than only golf.

For some reason, I really like women’s golf outfits. Sexy, little skirts and form-fitting tops that allow me to show off my curves to not just my husband, but others too. I’m in my mid-30s and have birthed three children, so I’m proud of the hard work that makes my body still turn (some) heads.

On this particular day, I wore a black skirt with a red top and black Nike cap. I fully admit I admired myself for some time in the mirror. And while I enjoy women’s golf clothes, I’ve always secretly had a thing for men in their golf attire too. The way they’d make a man’s butt look outstanding, or accentuate their toned legs and arms. Just kind of made me melt. Read more »

I (M26) Get To Watch Them (M28/F27); The Sequel – This Time I Join!

*Reading ‘I Get To Watch Them’ on my page first is recommended.*

Almost a week had passed since that night I watched Steve and Rachel have sex at his apartment. I talked regularly with him, but I could tell Rachel avoided me some at work. She was embarrassed, and truthfully if I’m being honest, I was too.

I kept going back in my mind to the following morning when Steve thought Rachel might be open to more. Was he serious? Just thinking about it made me hard. I’d always found her attractive, but the thought of playing with her and maybe even fucking her? I was definitely open to it, while at the same time not wanting to appear as though I was pushing it to happen.

Steve texted me on Thursday night and invited me over on Saturday.

“Is Rachel going to be there?” I texted back.

“That’s the plan,” he replied. “She wants this to happen again.”

By ‘this’ I wasn’t exactly sure what it meant. Was I just going to be watching again? I mean, don’t get me wrong, I was open to it. I just wondered if I might be participating more this time around. Read more »

I (M26) Get To Watch Them (M28/F27)

This particular Friday night was no different than any other while in the middle of the pandemic. After a long week at work my plan was something on the grill, a few beers, maybe a movie and the evening likely ending with me rubbing one out.

My ex-girlfriend and I had went our separate ways less than a month before the this whole thing kicked up last March. I work in healthcare so I’ve been very diligent at keeping my distance and pretty much have been in self-quarantine for the better part of nine months. There’s been no sex, no parties and really little-to-no socialization on my part. It’s been a grind.

I had just shed my scrubs and took a long, hot shower. As I was drying off a co-worker called and asked if I wanted to come over for a few beers and to hang out. Honestly, I had been looking forward to (another) quiet night, but figured why not.

When I got to Steve’s house I was surprised to see Rachel there, too. Her and Steve kind of had this FWB thing going the last six months or so. Like me, their social lives were relatively non-existent, so I think both of them were just using the other to pass the time. Read more »

The College Reunion, Part Six; The Final Chapter

After dinner that night Jenna retired to bed early. The multitude of drinks had finally caught up to her. Emma and Teresa both had early flights to catch in the morning and also went down for the evening.

Maggie and I had just finished cleaning the kitchen and it was still only 9 p.m. She was on the same flight as Jenna and I the following afternoon so the two of us decided on a glass of wine and a dip in the hot tub since we didn’t need to be up early. It seemed like the perfect way to end this girls weekend.

“So that was kind of a crazy afternoon,” I said to Maggie, sipping from my glass of wine immersed in bubbles with the steam of the hot tub rising over us.

“To say the least,” replied Maggie. “I was a little surprised at how everyone opened up. It was fun. I thought maybe you’d have a different story to tell, though,” she said with a wink.

I knew what she was talking about. Remember earlier when I commented about Maggie not being afraid to experiment with her sexuality? Well, she wasn’t. And back in college when we were roommates our sophomore and junior years I actually experimented with her. Read more »

The College Reunion, Part Five (of 6); Maggie’s Story

Maggie’s Story

The end of my marriage took a toll on me, but I knew I needed to keep going for my own sanity. I immersed myself in working out. And after just a few short months I had regained some of the confidence that left me.

I met a guy where I worked out who was much younger than me. Let’s just say if I had gotten pregnant in high school he could have been my son. His name was Dak and he was a personal trainer. Gorgeous eyes, a chiseled face and a toned and fit body. Did I mention he was a light-skinned black guy? Well, he was. What he wanted with me I don’t know, but I didn’t have a problem being his MILF for a while.

The sex with Dak started out pretty average. I like to think me being an older woman helped to improve his love-making. The first few times we were together he just didn’t know how to make love to me, but with his body and that delicious cock I wasn’t going to just kick him to the curb. He had way too much potential. Read more »

The College Reunion, Part Four (of 6); Jenna & Leah Tell Their Story

Jenna & Leah’s Story, part one (told my Jenna)

Pre-kids there was a time at my parents lake place where the four of us ended up skinny-dipping together. That was when all of us were in our 20’s and had too much to drink, but it just kind of happened and we all went along with it.

Five years ago when Leah and I turned 35, we did a trip to Mexico with our husband’s. I’m not sure when and how things got to the point they did, but it was definitely fun for all four of us.

After a long day (and night) of drinking Leah’s husband Justin joked that we should all go skinny-dipping in the ocean for old times sake, which of course was backed up by my husband Mark. I’m not sure what got into Leah and I, but it sounded like a decent idea and next thing I know, we’re going along with it and the four of us are naked in the ocean.

After 15 minutes or so of acting like teenagers we dressed on the beach and went back to the hotel. Both Justin and Leah agreed to join us for a nightcap. Read more »

The College Reunion, Part Three (of 6); Emma’s Story

Emma’s Story

So this is going to sound a little weird, and trust me, I would have thought it was years ago, too.

The first time I was pregnant I found myself always being horny, especially in the third trimester. Mitchell and I always had a pretty good sex life, but my sex drive literally went into overdrive. And it wasn’t just penetrative sex. It was anything connected to sex.

Since high school I’ve happily given head to him, but when I was pregnant there were times I’d suck his dick multiple times per day. And, oh my, my nipples….from just the tiniest bit of stimulation I would cum. If Mitch and I weren’t together, then I was getting myself off.
I started to question whether or not I was normal, but when I’d research I learned that what I was feeling was actually very natural. But what about Mitch?

Well, he seemed to be really into it, as well. At first, I just thought it was him being sweet and taking sex when he could get it, but after digging a little deeper I was starting to wonder if maybe he had some sort of pregnancy fetish. I didn’t even know something like that existed. But it does. Needless to say, the last 12 weeks of my first pregnancy was the best sex the two of us ever had until that point. Read more »