writersexguy, Author at NSFW story

[MF][MF] The Reluctant Holiday Swap

My submission for the November 2020 contest.

TL;DR, if you read [this story](https://www.reddit.com/r/gonewildstories/comments/ixw8ue/mfmf_wedding_reception_swap/), you heard about Anna’s and my first time swapping with another couple. But it wasn’t *my* first time swapping. I only shared the details of my first swap with Anna after our time at the wedding with Sarah and Dan, and I eventually came clean about my numerous exploits when I was in college and thereafter. To my surprise, Anna was into all of it, and wanted to explore further (those stories for another time). What happened here took place when I was 23 years old, so a *very* long time ago, and in college, when my girlfriend Lee (not her real name) swapped with a couple named Doug and Jeannie (not their real names) after a work holiday party.

Lee was the first girlfriend I had who pushed the envelope sexually. I wrote before about Tami (not her real name) and a car chase, but my relationship with Lee was something different. Lee pushed all of the boundaries sexually, and our relationship, while toxic like eating paint chips, definitely cemented my interest in being open to new sexual experiences, no longer feeling guilty about being a sexually charged individual who grew up in a conservative and Christian household, and even through the most trying of circumstances — solidified what I liked, and what I didn’t like, sexually. Read more »

[MT] The Car Date

TL;DR I met a crossdresser through an internet dating site, and our first time was in her SUV.

Carrie (not her real name) and I hit it off right away. She wasn’t that tall, wasn’t that fit, but at the same time wasn’t this weird caricature of women I had seen in the past. She dressed in a way that I liked, her makeup was perfect, her clothing was hot and her look was exactly what I enjoy, and as far as people go, I was elated when she suggested that we park behind this mini mall on that Tuesday afternoon.

I stalked the location on Google Maps before agreeing to meet with her. Sure enough, the back corner of the parking lot is exactly what Carrie said it would be. So I told her that I would show up, she asked me to promise that I would show up, I reiterated that I would be there, and she asked me what I would like her to wear. She sent along a bunch of pretty hot photographs, all clothed, but still the optics/image is what I was looking for, and I picked a look or two that worked for me. We talked about what we might like to enjoy that early afternoon, and she basically said that if everything was cool that she’d be into making out, maybe some mutual oral, and that she loved being topped — if everything was super, super cool on our first date. We also exchanged details about the vehicles we would be driving, and I showed up super early. I wanted to make sure that the current state of the lot matched what was on Google Maps. And it did. Read more »

[MF] I Knew that we were Going to Fuck

TL;DR I met a woman on a vanilla dating website. We had a sexy phone call then a so-so date that turned the corner after we went clubbing, went back to her place, and spent the night together.

Once I came to terms with the fact that I’m a person with a huge appetite for sex and kink, it made dating a lot easier. Simply put, I needed to date someone who was into similar things as I, but a lot of that had to do with sex rather than, say, making music or going apple picking or reading or having some laughs, you know, the basic stuff.

At first I tried to meet women through an adult site, e.g. AFF. Result? Total bust. Then I decided to use the vanilla dating sites and literally search for women who were bound to satisfy the sexual part of the relationship that I so desired. And that’s when I found Jules (not her real name).

[MF][MMF] The Year of Linda and Dan

TL;DR I “dated” Linda and Dan for a year, and, at least in the short term, satiated their thirst for Dan enjoying his role as a cuckold (I didn’t know it was called cuckolding at the time). This story is about how we became “really good” friends about a month into our relationship.

I was early to mid 20s when this took place. Linda and Dan (names changed) excited me greatly. Hope you enjoy this sordid tale of lust.

My second job in the Boston tech market was, frankly, my dream job. I was young, and yet I got to contribute to this up and coming company, and nobody questioned my age; for my really friendly co-workers, it was about ability and mentoring a young person like myself. People would frequently drop by my office and kibitz about work and life, and even when they didn’t like my work, they would still mentor me so that I wouldn’t make the same mistake twice.

[MF][MF] Wedding Reception Swap

TL;DR My girlfriend and I swapped, for the first time, with a married couple, after a wedding reception, and holy crap — it was the hottest thing *ever*.

Names mentioned here (Anna, Sarah, and Dan) are all fictitious, although the events are 100% true.

We ended up in our hotel room. I was fucking Sarah (Dan’s wife) doggy style, and Dan was fucking Anna (my girlfriend) doggy style on opposite sides of a queen-sized bed. If that wasn’t hot enough, hearing the ladies tell each other how hot this all was (no shit?!), and how it was so hot to watch one another get fucked by someone else, before they started touching and kissing each other — really brought the whole evening together.

Holy shit. This really happened in my life. It was 19 years ago, but who’s counting?

Friday nights were Anna’s and my “hot” nights. Yeah, we had sex with an exciting regularity, but Friday nights she would roll out the lingerie and heels and g-strings, we’d drink some wine, then we’d carry on until mid Saturday afternoon.

[MF] Rush Away Seeding

TL;DR Got caught parking with my pants down, enjoyed a short but passionate car chase, then came in my girlfriend for the first time.

** All participants in this story were of legal age; in this case, we were both 18+. **

I dated Tami (not her real name) towards the end of high school and through my first year of college. Yes, she was my first, and yes her thin frame, gigantic rack — and although her extensive collection of lingerie, stockings, and heels was odd for a woman of her age, I’d be lying if I said that she didn’t excite me. She excited me. Greatly. And she knew that I was excitable as well, so when I came back home for Christmas break in 1989, we picked up exactly where we left off, and multiply so.

[MF] I Had a Summer Romance with an 18 Year Old Woman when I was 33

This story is true, and is a tribute to [this fantastic story](https://www.reddit.com/r/gonewildstories/comments/el4zrv/the_first_time_i_let_a_guy_cum_inside_fm/) about a woman and her first cum inside by a guy. Plus a couple of people messaged me to ask for more details. In no way do I intend to steal that author’s thunder… in particular because there was a *lot* of thunder in her writing. :-)

Update 2020-01-09 : Looks like they deleted the story. That’s a shame!

Note that names have been changed.

Between the time I was 28 and 33/34 I went through this phase where *all* of my relationships were sexual in nature. I was a late bloomer; what can I say? Even though I’d had relationships that involved sex, it was not until I was honest with myself about having sexual interests that were against the norm that I was able to relax and enjoy this part of myself.

Adult websites such as Adultfriendfinder and SwingLifeStyle as well as the craigslist “casual encounters” had come online a few years earlier, and brought a lot of bounty in terms of meeting couples for threesomes or for MILF hunting (there was a time in my life where MILFs and I *weren’t* the same age ;-) ). Read more »