First anal for pregnant coworker [MF]

Stephanie and I used to work together for a couple of years, and often chatted about various things. She was not the woman you would typically call hot, her tall, slim figure, thin hips and small breasts didn’t offer a lot to look at. She had a cute but average face, dirty blonde hair and wore thin glasses. But she had an amazing personality, she was smart and witty. She was in her late 20s and I was 35 at the time. The conversation sometimes did turn flirty, but it was more fun banter than either of us being serious about. I had no way of knowing, but I always thought that she never was too interested in dating and I was convinced that she must be rather boring in bed.

Caught Watching Porn Pt. III [Roommate] [Pegging] [MF]

[*Part I and Part II are over here*](https://www.reddit.com/r/dirty_boy69/comments/vifcax/caught_watching_porn/?utm_source=share&utm_medium=web2x&context=3)*. I advice you to read those first. Enjoy your read.*

When I opened my eyes the next morning, I felt relaxed. Relaxed and ready to begin a new day. I got out of bed immediately, I went to take a dump and then I went over in the bathroom. To fix myself up a little bit. When I was done, I headed towards the kitchen. Wearing nothing but my comfy stay at home clothes.

In the kitchen I made myself some breakfast – some bread with jelly on top – and brewed myself a nice cup of burned bean juice. While I was filling up the coffee machine my roommate walked by. She clearly looked like she was up and running for a few hours. Yes, she is more of an early bird than I am. She was dressed up to go out for a run.

No, we were not speaking about the fact that I was eating out her pussy in the previous night. We pretended that this had never had happened. She just told me that a parcel for her would arrive in the next hour or so. She asked me if I was home, and if I could accept it for her. Naturally I said yes. Then she left to run a few kilometers.

Sexy high school reunion led to sexy storytime – let [m]e know i[f] you want more! [meta]

So I’d just walked into my 10th High School reunion party when I saw her. Jenny Jones (not her real name, because her real name is Sarah Smith and she’d probably be annoyed about it being used in a dirty story online), my all-time HS crush. She was an unidentifyable mix of French and Asian and Black and Canadian and Jewish, she stood between 5’0” and 6’1”, with long thick slender legs and impossibly-perky antigravity-enabled tits that my cyborg-vision instantly identified as being perfect natural DD’s. Her flawless skin was pale like moonlight while also sporting a perfectly-smooth tan that definitely came from working outdoors rather than a tanning bed, and her makeup was bold and tastefully understated.

Jenny had been the captain of our schools volleyball team and soccer team and cheer squad and chess club, and had the ass and brains to match. I’d been madly in love with her when we were teens, but back then I was totally invisible to girls like her. We’d kept in loose contact on FB, and I’d come to really respect and admire her for her inspiring work to save orphans while also competing at the national level in woman’s synchronized diving, but it was clear she’d never forgotten her small-town roots, because her dirty pickup truck had a novelty license-plate holder that read “I’VE NEVER FORGOTTEN MY SMALL-TOWN ROOTS” and it was in her profile pic.

My first Experience

My .. ex? My only man. The man who helped me discover myself. Everything about me… he validated. Call me silly.. but I still feel him to this day. He is like 6’2” and i am 5’8”. Whenever we were together i felt like i was his possession. This boy held me like he loved me or some shit. I actually think he may of had some deep feelings there. I hope. .

This story about our very “first time”. It was so unexpected for me and still makes me get uncontrollably turned on. It was 2008. I was his best friend. We had been friends since elementary school. I was barely in high school when we first started this. He is my age. Both 29 now. Anyways, i was typing on the computer and he cuts the lights out and walks up behind me and says in my ear “its just us here. I have held this back for as long as possible. You can leave if you want, but you know i love you. I dont wanna see you hurt. But im begging… can I please just kiss you? I wanna kiss you. Thats all i can think about”. His breath was warm on my ear. He smelled like everything i wanted. And I turned around in the dim computer lighting and said “when we kiss, im probably gonna get hard. Because i like kissing.” And he said “well i can take care of that also babe”. (Very bold). And i kissed him so hard right then and there. I was in heaven. I felt everything- like heroin pulsing through me. I wanted every piece of him. I was encapsulated by his grip and gentle lips. He nibbled on my neck and pulled my hair back to control me. He wanted to control me. I wanted him to control me. I wanted- him.

Cumming inside [M]y ex’s sister [F], years later…

When I was in my early 20s, I dated a woman named Catalina (or Cat) who was a few years older than me—a completely stunning half-Argentinian woman with small but perky tits and the most amazing ass.

The story of our (IMHO extremely hot) first hookup: https://www.reddit.com/r/gonewildstories/comments/v46u46/fucking_my_coworker_f_raw_while_our_other/

That one time we tried anal: https://www.reddit.com/r/gonewildstories/comments/vicslj/spontaneously_trying_anal_with_my_coworker_f/

Anyway, Cat and I parted ways after a few months of hooking up (during which time we had some of the most amazing sex I’d ever experienced). As intense as the sexual chemistry was, we just didn’t have much else in common. We were both living on the West Coast at the time, but she moved away not long afterwards.

Fast forward a few years, and I’ve just gone through a really awful, painful breakup with a different woman, so I’m swiping through dating apps for literally the first time ever.

One Tinder match looks vaguely familiar, though it takes me a second to place her…

Then I realize with a start (and the beginnings of an erection) that I’d matched with Elena, my old flame Cat’s younger sister.

After work happy hour leads to my first [MFM] threesome with a traveling nurse

Let’s rewind the clock to the beginning of March, 2021. While my actual work was slowed way down, I had a day in the OR during the first week of March, and then had another in the second week of March. That in an of itself was unusual for me, but it worked with other plans I had. When I had gone in the prior week, one of the scrub nurses with whom I worked was a travel nurse (we had a number of staffing issues in our city, and travel nurses could make good money by going that route).

We only worked with one patient together, but my takeaway from that couple hours was that she was talented and experienced for her age, but perhaps more important to GWS, she had amazingly beautiful eyes. We were both masked the entirety of our time together, so other than a general sense of her figure, I had nothing to go off of. She was about 5’4”, and had a slim figure, at least from what I could tell. Her eyes though, my god, the closest I could say is Ana De Armas (to the point that when I watched No Time to Die, other than Ana having darker hair, they were *very* similar).

Clementina, Part XXIX [GORE, extreme, sf/horror/fantasy, monsters, non-consensual, transgender, anal, lactation, TFFF, incest (m/s)]

WARNING: THIS IS, AT TIMES, A HORROR STORY. THIS PART INCLUDES BODY HORROR, WEIRD SLIMY EXTREME SEX, ANAL, INCEST, LACTATION, GORE, AND MORE. MUCH OF THIS STUFF IS BIOLOGICALLY IMPOSSIBLE.

EXTRA WARNING: THIS EPISODE HAS EXTREME GORE IN THE FORM OF SLOW IMPALEMENT.

As with the previous installments, if this sort of thing is not your cup of tea, please do not read any further. I want readers to have fun – not be disturbed and sad. Please heed all warnings!

If you’re the kind of person who ignores warnings and regrets it later, have this: r/eyebleach

There are transgender people in this story, there are monsters in this story, and there are transgender monsters in this story. I AM NOT IMPLYING TRANSGENDER PEOPLE ARE MONSTERS. I am just having fun with genders, ‘cause, after all, ain’t that the point?

This story assumes you have read all previous parts. If you haven’t you will probably find some of this bewildering.

This part continues chapter 6. This part begins immediately after Part XXVIII ends.
The Clementina story line is approaching its logical climax. There will probably only be a few more episodes before we wrap this thing up.

I’ve been trading sex favors for Real Estate Flips [FM]

My boyfriend and I run this real estate business. Basically we flip houses – if you ever seen any home renovation/flip TV show, then you have a pretty good idea on what we do. My boyfriend is the numbers/planning guy, and I’m the designer/agent. We typically hire contractors and tradesmen to help with the construction aspect of the flips.

At first, we had no idea what we were doing. It all just seemed so easy on TV. But once you get into a project, and the cost keep on rising, and you’re maxing out your credit cards, yeah, that sucks. On one of the first projects, we were all in. Like we needed to finish the house and sell it fast just to dig ourselves out. And of course, an unexpected cost surprise came up.

Steve was our contractor on that job, and he’s asking for money that we didn’t have. My boyfriend casually suggested that maybe I flirt with him. My boyfriend and I have a very liberal/sexual relationship, so this didn’t really bother us. So when Steve was trying to explain the surprise, I was heavily flirting with him. Wore a low cut tank top, and was practically throwing myself at him. Steve eventually got the hint and offered to ‘help’. But only if I blew him right then and there.

What if… Jackie Showed Up After Graduation Pt. 5 [M/F/F] (Margaret & Janice)

[Home](https://www.reddit.com/user/Teososta/comments/q3su15/amnesia_was_the_best_thing_to_happen_to_my_gf/)

=== ***Chris*** ===

Janice changed her mind. She wanted an extra day.

I sent Eve a text saying I’d probably be late tomorrow, and that got her a little steamy, so I explained why and she understood, but she is still mad. She still wants her own action tomorrow night, and now I’m wondering if I can even deliver.

Well when I woke up next to Janice, the first thing I did was give her a good morning kiss. At first she looked at me weirdly, almost in shock, but then it finally registered to her who I am and what we did and she returned the kiss.

“I hadn’t slept like that in a long time,” she chuckled, “a really long time.”

“You were probably stressed out,” I said while gently brushing her cheeks, “sex can be quite relaxing and it releases dopamine and serotonin.”

“Do tell. I felt things I haven’t felt.”

Well, she cooked breakfast for me and we ate with smiles and laughter. She told me about her college days, dull as it is, and mostly the reason why she lived a sexless life until now.

Picked up – Revised (prostitution, pregnant, masturbation, slapped, forced anal, oral, choking, piss drinking)

She chewed her bottom lip, cherry red, as the stranger rubbed her swollen belly. He stared intensely at her chest and below, not caring for anything above her shoulders. Her crop top covered none of her belly and barely contained the top 75% of her chest, which had grown almost as much as her stomach. She smiled at him, her look as vapid and empty as she needed to feel. The stranger spat some tobacco on the bar floor, looking at her tits as he talked.

“Do you even know who the daddy is?” he asked rudely. She started to answer until the glare in his eye told her to stay quiet. “Nah, dumb cunts like you never know, do you?” She shrugged, which bought her a slap to the face. Not hard, but it got her attention.

“I asked you a question, you stupid bitch,” he said. She rubbed her cheek and lied, telling him she didn’t know. That made him smile as he rubbed her thigh at the bar, sliding his hand up her leg. When she put her knees together, his dirty nails dug into her soft skin until she parted them. He didn’t care if people watched or saw, not that anyone was really watching them. It was late and most were drunk or just didn’t care.