My roommate and I gradually went from drinking buddies to fuck buddies, Part 4 (The finale) [MM]

[Part 1](https://www.reddit.com/r/gonewildstories/comments/9tp8oi/my_roommate_and_i_gradually_went_from_drinking/)

[Part 2](https://www.reddit.com/r/gonewildstories/comments/9tpbnl/my_roommate_and_i_gradually_went_from_drinking/)

[Part 3](https://www.reddit.com/r/gonewildstories/comments/9tpern/my_roommate_and_i_gradually_went_from_drinking/)

**Part 4 – The Finale**

My roommate and I gradually went from drinking buddies to fuck buddies, Part 1 [MM]

This story took place years ago when I was renting a room from a long-time friend in his newly purchased townhouse. We were both in our early 30s, single, and working easy jobs with few responsibilities. The events are all real and occurred on different nights over the course of the last few months we lived together. I’m not a writer or anything so forgive me if I don’t come across as the best story teller. If it seems slow, don’t worry, it picks up rather quickly. The dialogue and events are as close to truthful as I can remember. I changed the names of everyone involved (not that it really matters, I suppose) but everything else is just how it happened. I’ve had some enjoyable binges of sex in my life, but the weeks I’m writing about here were some of the most memorable. I frequent r/gonewildstories but I have never confessed anything. So, here it goes…

The night I got incredibly lucky and lost my virginity [MF]

When it comes to my early sex life, I like to think I got by on sheer, dumb luck. I was an awkward kid in high school into early adulthood, not bad to look at, and pretty funny, but also weird, shy, and not very fashionable. So imagine my surprise when I lucked up and got myself a smoking-hot girlfriend my junior year, whom I’ll call Carina. She was 5’2”, medium-brown complexion, lithe figure, nice tits, and later, a tattoo on her lower back.

Long story short, I fell for her hard. When we broke up, I went to pieces. I was a mess. I spent that summer out of the country with relatives and came back with my head on straight and ready to move on. After I graduated, I got my first job at a department store and was getting ready to start college on a scholarship. All in all, things were looking up.

Then one day, I got a phone call. It was Carina, looking to reconnect. She extended an open invite to hang out at her place, anytime. Literally anytime. In my naïveté, I thought nothing of it other than she was trying to be friendly. Yes, I was once that clueless.

Circumnavigation, pt.1 (NSFW, mf, romance, oral, autobiographical)

Circumnavigation, risking it all

Prologue

Note: This series is autobiographic, the events are true as I can get ‘em to memory, but it’s been 22 years and a few details may have run together. It’s long and takes a while to pick up steam, hopefully not too boring ^_^

In 1996 I was active duty Navy and assigned to my first ship, a guided missile frigate home-ported in Mississippi. I was 23 years old, happily married, full of myself and from what I could tell, at the start of a successful career.

I had already completed one deployment to the Middle-East and had the obligatory “Sailor experience” under my belt of wandering from bar-to-bar, sampling food from cafes and street vendors, shopping in bazaars and boutiques in Barcelona, Haifa, Hurghada, Massawa, Djibouti, Manamah, Dubai, Muscat and Marseilles.

Through all of that I maintained my marital vows and thought myself all the better for it. I had been tempted, tested and tried numerous times and escaped with my virtue unscathed. I wore my fidelity like a crown and secretly judged my shipmates who failed the test. *Sigh* The higher the pedestal, the farther the fall.

4 A country summer, Part 4 (NSFW, golden showers, anal, mf, tg, mm, incest, transgender, gay, MILF, GILF)

*

The next morning I wandered downstairs to find the house empty and a note on the kitchen counter explaining that my grandparents had to take a friend to Pendleton and would be gone until late that night. I was on my own for breakfast and dinner, lunch would be out at the state park with the other side of my family.

“Not a bad thing,” I thought. “Maybe some time to cool down was a good idea.” Thinking about recent interactions with Grandma.

I got dressed for the park in a tank top, swim trunks and sandals then grabbed an old pair of creek-shoes from the laundry room. Creek shoes were just old worn out tennis shoes you wore in the creek with no socks. Getting soaked and drying out made them stiff and good for nothing else, but protected your feet when wading and swimming in the creek. I had left a pair here a summer or two ago when visiting with my family.

An Intro Into Hotwife (Voyeur)

She looked beautiful.

She always looked beautiful. Perhaps it is what she was getting ready for that made her look even more beautiful to me tonight. Tonight was a special night. Our sex life was excitingly wide ranged. I could be sitting around and the thought of a soft, sensual, loving night of love making would cross my mind and I would lose himself for a moment. I loved her and I loved making love to her. On the other end of the spectrum lies the animalistic, sweaty, dirty talk fueled, porn star-esque fucking that made my cock throb. The main topic of the dirty talk usually focused on watching her with another man. Admittedly, that fantasy started with me. I knew she wasn’t into it, but I loved her for trying. Truth be told, I felt guilty that I fantasized about watching her. Felt weak that I could never put into words exactly why it turned me on so much. But during those amazing fuck sessions, I just let himself go, if just for a moment.

First time anal with a long time girlfriend [MF]

During my final year in college, I met and began dating Jackie. She and I hit it off immediately. We were into the same bands and movies, and shared a similar sense of humor. It also helped that she was adorable. She was 5’4″ 120 lbs. Dark shoulder length hair and hazel eyes. She had some curves too. Only a 34B up top, but her ass was PHAT! I grabbed at it every chance I could, and she would tease me relentlessly with it too.

Once we graduated college, we found jobs in the same area and got an apartment together. Most mornings and weekends were spent lounging around where she would be in a t-shirt and a thong, wiggling her ass around trying to get me riled up. Most times it worked for sure. I was always 100% honest about my desire to fuck her in the ass, but she would always say “I’m sorry, baby. No.”

My first time with anal [MF]

This was almost 30 years ago, with my second girlfriend.

I was 18, girlfriend was 17, almost 18. She lived with her mom, and I was there along with a bunch of her family members for Thanksgiving.

Football on the TV, food laid out, probably a dozen people in the house.

She was frisky, often flashing her boobs, ass, or pussy when we were in public, when nobody was looking. She’d also slide her hand down my pants at any given time. She was always wet, and always horny.

“Follow me!”

We went to the bathroom, where she pulled her shorts off and got on her hands and knees on the bath mat. There’s a dozen people in a room just on the other side of the wall, and this is the only bathroom in the house… but there’s pussy.

I pull my jeans down, get behind her, and slide my dick into her pussy, while grabbing a handful of hair. I reached down and grabbed a tit; she loved them being handled really roughly, and was often bruised. I tried to fuck quietly, but…

“stick it in my ass!”

Prompt: Girlfriend got drunkenly group fucked by 3 guys at a frat house.

When my girlfriend was in college, she got drunk at a frat house with some of her friends for a football tailgate.

A guy she met there got her alone, brought her into a room, and he and his friends took turns on her. She was too drunk to remember many of the details, I know there were 3 guys in the room. She also remembers her friends knocking on the door looking for her, but one of the guys told them nobody else was in the room.

I get extremely turned on thinking about it.
If anyone is interested, I’d love to read a story written in the third person along those lines. PM for any details you’d want to know if you’re up for it!

An unexpected layover in Dallas [MF]

I’ve seen a few posts on the sub recently questioning how every guy poster bangs some incredible smokeshow girl, how every girl poster finds a dick that’s always the most enormous 27 inch dong they’ve ever seen, and how all posters manage to junk-jackhammer for 2.5 hours straight with seemingly infinite stamina. People come here to share their most incredible and noteworthy experiences, so I don’t see the problem personally. Nevertheless, here’s an event from a couple years back that’s a bit different from most things I’ve read here and should satisfy the sceptics.

A couple hours back, I had found her gonewild post. It was a typical “do u like what u see??” image from a new account – a badly taken close-up of her huge tits squished together, kind of like [this random picture I found on gonewild](https://i.redd.it/u93zwdzrgiuz.jpg). Grainy, bad lighting, unflattering angle, and missing a tag. The girl next door with her flip-phone quality camera generally has no chance on that sub, but that doesn’t mean the photo and girl weren’t both hot. They were. And that made her a good candidate for some fun.