Author: headstrongcocksure

Fucking at the Swim Beach [MF]

This story took place a number of years ago, maybe 10 or so, but I don’t honestly remember. Every summer my family has planned a family campout. This is basically my parents, and their 4 kids, spouses, and grandkids. Why we always plan this for late July in Kansas is beyond me, because normally we’re out camping and during the days it’s sunny and temperatures in the low 100s.

This year was no different, it was sweltering hot outside and so during the day we would find ourselves all hanging out at the swim beach for the lake. It was packed, people everywhere. Having young kids most of our time was spent in the shallow water helping them build sand castles. After a while mom suggested that she could keep an eye on this kids if my wife and I would like to take some time to go out into the deeper water and do some swimming. We took her up on the offer and as she kept an eye on the kids my wife and I made our way out into the deeper water. Read more »

Gradually Loosing My Virginity [MF]

I was sharing this story with a chat partner earlier today and thought it might be a fun one to share here too. I’ll give a little bit of background here. This story took place while I was 19 and a freshman in college. Stacey was a Sophomore and we began dating on her 21st birthday. We had both been raised in Christian homes and were both intending on waiting until marriage to have sex. That may not be entirely true, but it’s what I told myself, but I also told myself I’d do pretty much anything outside of “sex”.

Prior to Stacey and I dating, my experience with women was limited to fingering one, making out with a handful, and under clothes fondling of breasts (in that order too). Stacey had no experience, I was her first boyfriend, first hand holding, first kiss…you get the idea. The story I’m sharing may read somewhat like a single encounter, but this was a progression that happened over the course of a few months. Read more »

Fucking Wendy at Her Parent’s House [MF]

This is another of my stories involving Wendy, and to put it in order chronologically you can following the links below:

Round 1:

[https://www.reddit.com/r/gonewildstories/comments/irj36f/my_first_time_with_wendy_mf/](https://www.reddit.com/r/gonewildstories/comments/irj36f/my_first_time_with_wendy_mf/)

[https://www.reddit.com/r/gonewildstories/comments/j48zni/an_evening_in_the_park_mf/](https://www.reddit.com/r/gonewildstories/comments/j48zni/an_evening_in_the_park_mf/)

[https://www.reddit.com/r/gonewildstories/comments/ilw6vh/wendy_dripping_cum_in_the_parking_lot_mf/](https://www.reddit.com/r/gonewildstories/comments/ilw6vh/wendy_dripping_cum_in_the_parking_lot_mf/)

[https://www.reddit.com/r/gonewildstories/comments/iwtboz/defiling_my_marital_bed_and_my_first_overnight_mf/](https://www.reddit.com/r/gonewildstories/comments/iwtboz/defiling_my_marital_bed_and_my_first_overnight_mf/)

Round 2:

[https://www.reddit.com/r/gonewildstories/comments/ifl5jq/cloneawilly_for_a_former_fwb_mf/](https://www.reddit.com/r/gonewildstories/comments/ifl5jq/cloneawilly_for_a_former_fwb_mf/)

— This Story Here —

[https://www.reddit.com/r/gonewildstories/comments/iuqusl/mf_getting_laid_at_walmart/](https://www.reddit.com/r/gonewildstories/comments/iuqusl/mf_getting_laid_at_walmart/)

[https://www.reddit.com/r/gonewildstories/comments/ihblt9/her_kid_is_watching_tv_her_boyfriend_on_his_way/](https://www.reddit.com/r/gonewildstories/comments/ihblt9/her_kid_is_watching_tv_her_boyfriend_on_his_way/)

This story is a continuation of the stories I’ve written that took place between Wendy and myself. This takes place during our second round of hooking up.

Wendy and I had been chatting a lot since reconnecting after our 5 year hiatus, and had even met up a few times, but hadn’t yet started having sex. Our meet ups, up to this point mostly consisted of just hanging out together, some making out, I’d fingered her a handful of times, and she’d given me a blowjob. We’d been talking about trying to meet up to have sex, but our after work meet ups always meant she had her kid with her, and since she lived with her boyfriend, meeting up at their place wasn’t really an option. Read more »

An Evening in the Park [MF]

This is another of my stories involving Wendy, and to put it in order chronologically you can following the links below:

Round 1:

[https://www.reddit.com/r/gonewildstories/comments/irj36f/my_first_time_with_wendy_mf/](https://www.reddit.com/r/gonewildstories/comments/irj36f/my_first_time_with_wendy_mf/)

— This Story Here —

[https://www.reddit.com/r/gonewildstories/comments/ilw6vh/wendy_dripping_cum_in_the_parking_lot_mf/](https://www.reddit.com/r/gonewildstories/comments/ilw6vh/wendy_dripping_cum_in_the_parking_lot_mf/)

[https://www.reddit.com/r/gonewildstories/comments/iwtboz/defiling_my_marital_bed_and_my_first_overnight_mf/](https://www.reddit.com/r/gonewildstories/comments/iwtboz/defiling_my_marital_bed_and_my_first_overnight_mf/)

Round 2:

[https://www.reddit.com/r/gonewildstories/comments/ifl5jq/cloneawilly_for_a_former_fwb_mf/](https://www.reddit.com/r/gonewildstories/comments/ifl5jq/cloneawilly_for_a_former_fwb_mf/)

[https://www.reddit.com/r/gonewildstories/comments/iuqusl/mf_getting_laid_at_walmart/](https://www.reddit.com/r/gonewildstories/comments/iuqusl/mf_getting_laid_at_walmart/)

[https://www.reddit.com/r/gonewildstories/comments/ihblt9/her_kid_is_watching_tv_her_boyfriend_on_his_way/](https://www.reddit.com/r/gonewildstories/comments/ihblt9/her_kid_is_watching_tv_her_boyfriend_on_his_way/)

For those of you new to my stories, Wendy was a semi long term affair I had in two parts. The first part, she was newly divorced with no kids, and I was married and cheating. During that time she loved the fact that I was married and sneaking around seeing her. She definitely enjoyed playing the role of mistress and often told me I was free to do whatever I wanted to her. I believe her exact words were “you can do anything, anytime, anywhere.” and “Use me as your own personal sex experiment”. I intended to do just that. She also loved a bit of cnc play.

With me being married, it was hard for me to host her, and so most of the times when we met up, it was either out and about, or I’d just go to her place. Meeting was usually the better of the options because that gave us more time instead of me burning 40 minutes driving, we could split the difference and each drive 15-20 minutes. Read more »

Defiling My Marital Bed and My First Overnight [MF]

This is another of my stories involving Wendy, and to put it in order chronologically you can following the links below:

Round 1:

[https://www.reddit.com/r/gonewildstories/comments/irj36f/my_first_time_with_wendy_mf/](https://www.reddit.com/r/gonewildstories/comments/irj36f/my_first_time_with_wendy_mf/)

[https://www.reddit.com/r/gonewildstories/comments/ilw6vh/wendy_dripping_cum_in_the_parking_lot_mf/](https://www.reddit.com/r/gonewildstories/comments/ilw6vh/wendy_dripping_cum_in_the_parking_lot_mf/)

— This Story Here —

Round 2:

[https://www.reddit.com/r/gonewildstories/comments/ifl5jq/cloneawilly_for_a_former_fwb_mf/](https://www.reddit.com/r/gonewildstories/comments/ifl5jq/cloneawilly_for_a_former_fwb_mf/)

[https://www.reddit.com/r/gonewildstories/comments/iuqusl/mf_getting_laid_at_walmart/](https://www.reddit.com/r/gonewildstories/comments/iuqusl/mf_getting_laid_at_walmart/)

[https://www.reddit.com/r/gonewildstories/comments/ihblt9/her_kid_is_watching_tv_her_boyfriend_on_his_way/](https://www.reddit.com/r/gonewildstories/comments/ihblt9/her_kid_is_watching_tv_her_boyfriend_on_his_way/)

Wendy and I had been hooking up for about a month or so when this story took place. Basically any time I could find an excuse that my wife would buy, I’d leave the house and meet up with Wendy. She was single at the time, and without any major responsibilities she could usually drop and go on short notice and would either meet me somewhere, or I’d just drive to her place and we’d go at it there.

This however had some planning behind it. It was Spring Break and the kids were out of school and my wife decided to take the kids to her parent’s house for the week. I had some work obligations that preventing me from being able to go, but I also found it a great excuse to be able to spend a few days hanging out with Wendy. Unfortunately, she was also headed out of town, but for the latter part of the week, so we’d have a few days that our schedules would overlap. Read more »

[MF] Getting Laid at Walmart

A number of my stories I’ve posted so far involve Wendy. She and I were FWBs two different times about 5 years apart. If you want some chronological order to the stories I’ve posted the links below, and I’ll break them out between Round 1 and Round 2.

Round 1:

[https://www.reddit.com/r/gonewildstories/comments/irj36f/my_first_time_with_wendy_mf/](https://www.reddit.com/r/gonewildstories/comments/irj36f/my_first_time_with_wendy_mf/)

[https://www.reddit.com/r/gonewildstories/comments/ilw6vh/wendy_dripping_cum_in_the_parking_lot_mf/](https://www.reddit.com/r/gonewildstories/comments/ilw6vh/wendy_dripping_cum_in_the_parking_lot_mf/)

Round 2:

[https://www.reddit.com/r/gonewildstories/comments/ifl5jq/cloneawilly_for_a_former_fwb_mf/](https://www.reddit.com/r/gonewildstories/comments/ifl5jq/cloneawilly_for_a_former_fwb_mf/)

[https://www.reddit.com/r/gonewildstories/comments/ihblt9/her_kid_is_watching_tv_her_boyfriend_on_his_way/](https://www.reddit.com/r/gonewildstories/comments/ihblt9/her_kid_is_watching_tv_her_boyfriend_on_his_way/)

I believe this story took place during Round 2, between the Clone-A-Willy and Alley Way stories.

Wendy and I had be chatting again for a while and had hooked up a few times already as a part of our reunion tour. One evening, I was at home with the kids and my wife was working late. She often worked late at night because she’s a night owl and enjoyed being able to work without distraction. Wendy on the other hand usually wasn’t free at night because either she had to take care of her kid, or she was with her live in boyfriend and father. Read more »

Normal Date Night Ends Up With Getting Laid at Church [MF]

For the most part, my wife and I have a fairly vanilla sex life, but every once in a while she throws me a curve ball, and this story is definitely one of those times. A little back story, my wife and I have been married nearly 2 decades and have multiple kids together. Part of the lack of sex in our marriage has to do with the kids, it’s sometimes hard to find that private time with the kids at home. When they were a little younger, we used to be able to go on date nights and leave the kids home and they’d go to bed by the time we returned and we could have some post date fun. However, as they’ve gotten older and are staying up later, now we return from a date night to find a house still awake, which isn’t great for ending a date with a bang. Also worth noting for the context of this story, my wife and I are both active in our church, and as a result some of the teams that we serve on, we have access to get into the building. Enough build up, let’s move on to the story… Read more »

My First Time with Wendy [MF]

I met Wendy through an add I posted on Craigslist looking for a friend with benefits. She was newly separated from her husband, but still having sex with him while looking for someone else to transition to. She and I hit it off and soon we were chatting non-stop and had decided to meet. Our first meet up was actually just hanging out and cruising around town. More probably could have happened but were both too nervous to make the first move. Funny/scary moment of the night, she and I were walking around the downtown area and ran into some friends of my wife and I. I introduced Wendy as a friend and chatted for a bit before moving on.

After that first night we both agreed we were interested in more, and would have been willing that night. So we agreed to meet up again with full intention of having some fun. I made up an excuse to leave the house one evening and drove straight to Wendy’s place. I got there and we sat in the couch watching TV for a little while before we started making out. We made out for a while, hands exploring each other’s bodies. I was groping at her tits as she was rubbing my cock through my jeans. Read more »

What Happened to the Married Teacher [MF]

I wrote about Kim last week, the first time I’d had sex with a woman other than my wife. You can read that story here:

[https://www.reddit.com/r/gonewildstories/comments/ineo2y/craigslist_success_the_married_teacher_mf/](https://www.reddit.com/r/gonewildstories/comments/ineo2y/craigslist_success_the_married_teacher_mf/)

Kim and I continued to chat after our first meetup. This was the first time either of us had sex outside of our marriages and so the excitement was palpable. I believe it was the following day after our first meetup that Kim was doing some shopping and wanted to just see me. So I met her in the parking lot of the stores where she was at. We didn’t do anything other than just talk, and I believe we kissed a little bit, but being out publicly was making me nervous.

It was late fall, and I believe Thanksgiving was the following week or so. We hadn’t had a chance to get back together since our first hook up, but we were going to spend the long weekend out of town (only about 45 minutes from where we live). However, I only had Thanksgiving day off and had to work the following Friday. Kim and I ended up making plans to get together over my lunch break on Friday since she was off that day. Read more »

Breaking Our Three Week Dry Spell [MF]

Most of my stories involve cheating on my wife. So thought I’d throw this story in to mix things up. I’d you really like the cheating stories, the best I can tell you about this one is that over the past week I’ve been chatting with a married follower, Elissa, who has been considering cheating, and we’ve been swapping stories and I may have helped to encourage her to meet up with someone local this week. I bring her up to tell you that while this story involves sex between me and my wife, she was in my mind pretty much the entire time we were fooling around.

It’s been three weeks since my wife and and I had sex. I remember this because I’d got to Topeka, KS that day to do some shopping. On a whim while waiting for a sales appointment (stupid COVID) I decided to swing by the local sex shop and buy my wife her first vibrator. We’ve talked about this for a while but hadn’t ever done it yet. Picking it up had the added benefit of a high likelihood of using it that night, and we did. Read more »