Spontaneously trying anal with [M]y coworker [F]…

Catalina (“Cat” for short) was a colleague of mind at a small West Coast marketing agency when we first met. For our first after-work hookup (with two other colleagues fucking down the hall), check out Part 1 of my previous story (parts 2 & 3 linked from here): [https://www.reddit.com/r/gonewildstories/comments/v46u46/fucking_my_coworker_f_raw_while_our_other/](https://www.reddit.com/r/gonewildstories/comments/v46u46/fucking_my_coworker_f_raw_while_our_other/)

After that first, lust-fueled night, Cat and I were inseparable for a couple of weeks. I spent the night at her place a handful of times during that period, and each time we’d start the day with some hot morning sex before heading off to work.

Except that, at least twice, we were very late getting to the office because I’d remained fully hard even after cumming inside her… so, after the briefest of breathers, I’d surprised Cat by sinking my cock back into her freshly-fucked pussy and starting all over again. (On these two days, we had to stagger our arrivals at the office and come up with different excuses, so our boss wouldn’t suspect the obvious).

Fucking [M]y coworker [F] raw… while our other coworkers fucked in the next room [PART 3]

PART 1: [https://www.reddit.com/r/gonewildstories/comments/v46u46/fucking_my_coworker_f_raw_while_our_other/](https://www.reddit.com/r/gonewildstories/comments/v46u46/fucking_my_coworker_f_raw_while_our_other/)

PART 2: [https://www.reddit.com/r/gonewildstories/comments/v8l92t/fucking_my_coworker_f_raw_while_our_other/](https://www.reddit.com/r/gonewildstories/comments/v8l92t/fucking_my_coworker_f_raw_while_our_other/)

My heart was pounding as I toweled off my hands and then stood very still to listen for the sounds of my coworkers getting it on, on the other side of Cat’s bathroom door.

There it was again: a half-stifled moan.

I pressed my ear to the door but couldn’t hear anything else. So I cracked it open as quietly as I could (fortunately, the hinge didn’t creak).

Now I could hear Ashley’s ragged breathing and what seemed to be a faint slurping sound. I realized Tim must be eating her out.

Gingerly, I pushed the door open and leaned my head slightly out, peering in their direction. Ashley was on her back on the couch, her legs spread and her hands holding Tim’s head firmly as it bobbed against her pussy. Her breasts heaved as she gasped and moaned, both nipples rock hard.

Her head was turned in my direction and she made eye contact with me immediately. As though she’d been watching for me to come out of the bathroom.

Fucking [M]y coworker [F] raw… while our other coworkers fucked in the next room [PART 2]

[*Thanks for reading! Appreciate any and all reactions/comments/etc.*]

PART 1 HERE: [https://www.reddit.com/r/gonewildstories/comments/v46u46/fucking_my_coworker_f_raw_while_our_other/](https://www.reddit.com/r/gonewildstories/comments/v46u46/fucking_my_coworker_f_raw_while_our_other/)

I woke up hungover with a slight headache and a dry mouth just a few hours after Cat and I passed out next to one another. Flashes of the night before came back to me as I rubbed my eyes and started to feel more awake—including the fact that our unprotected sex had ended with an almost primal orgasm deep inside my coworker, even though neither of us had said a word about birth control.

I sat up and took a sip of water and then looked over at Cat, who was sleeping peacefully on her stomach facing away from me. Both of us were still naked and the sheets were a total mess, so the lower part of her completely perfect ass was exposed.

I leaned over, my cock hardening as I unabashedly took in the view. The sheets were visibly damp beneath her pussy lips, so my cum must still have been leaking out of her.

Trying to stop this line of thought (and my growing erection) and get back to sleep, I laid back down—and put a hand lightly on Cat’s shoulder, out of instinct and affection, giving it a light rub.

Fucking [M]y coworker [F] raw… while our other coworkers fucked in the next room

When I was in my early 20s, I worked at a tiny marketing agency on the West Coast with a woman named Catalina (or Cat, for short) who was a few years older than me—a completely stunning half-Argentinian woman with small but perky tits and the most amazing ass. She started about six months after I did, and we mostly worked on different accounts, but we hit it off and started flirting at work immediately.

The office culture involved VERY late hours and a pretty intense “work hard/play hard” atmosphere. One night, after working late, a big group of us—including Cat—decided to go out for happy hour and really tie one on.

Eight (or so) of us started off the night at a favorite nearby watering hole. A few rounds later, two had gone home and the remaining six of us took the party to a second location, a bar with a large outdoor space in a semi-residential area.

Cat and I had been flirting pretty heavily all night… and by now, we were both pretty drunk. We sat down next to each other, and at one point she touched my leg just above the knee while laughing at something I’d said.

College friends (FF) drag [M]e off to unexpected threesome – Part 5 [FM]

In the weeks after our threesome, Erin left for a semester-long study abroad program (though I’d reconnect with her upon her return). In the meantime, Molly and I settled easily back into the same friendship dynamic we’d had beforehand—except that every once in a while, she’d hit me with something explicit just to get a reaction out of me. I think it turned her on, and it definitely made me rock hard.

One night, after one of our comedy group’s weekly meetings ended, Molly and I happened to be the last ones out and started to walk and talk together (about classes, our upcoming comedy show, mutual friends, etc.). She hugged me as we parted ways on the quad, her heading off to an evening movie screening for a film class (this being California) and me to dinner with friends.

As we hugged, she whispered in my ear:
“You should rail me again sometime soon.”

My jaw dropped. I got instantly rock hard.

Molly cackled mischievously as she ended the hug and turned to head off to her screening.

“See you later, my dude!” she said. I struggled to hide my erection as I shuffled off to change before dinner.

College friends (FF) drag [M]e off to unexpected threesome – Part 4 [FFM]

I teased Erin with the head of my cock, dipping just the very tip into her warm, glistening folds and making both of us gasp, then drawing it fully out again. Laying next to us on the bed in the early morning light, Molly sat up on her elbows to watch.

Slowly, I pushed the slightest bit deeper and then pulled out again, driving both of us wild. Erin’s pussy was slick and hot and inviting, and my cock was soaked from Molly’s juices, having just fucked her to orgasm. So I could’ve easily plunged all the way inside.

But instead I savored the sensations of an agonizingly slow fuck, feeling Erin’s walls quiver as she gripped me, feeling her fingernails dig into my ass as she tried to pull me deeper. I refused to let her, determined to go as slowly as either of us could stand it until I couldn’t take it any longer.

“Oh fuck, oh please fuck me,” Erin was saying, writhing as I penetrated her, completely dick drunk. I finally bottomed out, flexing my cock against her cervix and holding it deep inside her, feeling the sensation of completely filling her.

College friends (FF) drag [M]e off to unexpected threesome – Part 3 [FFM]

I don’t remember making it from the couch, where we’d collapsed in a pool of sweat and satisfaction, to Erin’s bed—but we must’ve at some point. Because that’s where I woke up, a few hours later, in a tangle of my friends’ naked bodies.

It was early morning. Between the cast party (following a comedy show that now seemed like forever ago) and two rounds of the absolute hottest sex I’d ever experienced, we’d burned through most of the night and fallen asleep together more or less spontaneously.

Gingerly, trying to avoid waking Erin and Molly, I extricated myself and tiptoed to the bathroom to pee. Coming back down the hallway, I drank in the sight: morning sun slanting across the naked bodies of my two good friends.

The sight, and the memory of everything we’d done to one another the night before, started to get me hard again. Still, my intentions were innocent as I crawled back into bed between them, slipping under the thin sheet and pulling it up to partially cover them.

Erin stirred a bit next to me, rolled over to face me, and groggily opened her eyes. We held one another’s gaze for a second. Then we started to drift together.

College friends (FF) drag [M]e off to unexpected threesome – Part 2 [FFM]

I went to Erin’s kitchen, still naked and reeling from the direction this night had taken, and poured myself a glass of water. Sipping it as I walked back into the living room, I took a moment to take in the sight of Molly eating Erin’s freshly-fucked pussy, her ass in the air invitingly.

Erin was lost in the moment and full of cum, moaning in pleasure, but she opened her eyes when she heard me walk back into the room and beckoned me over. She stroked my cock a few times, getting it hard again.

“So slippery,” she said. “From our sex.”

She took me in her mouth, swirling her tongue around the head of my cock and stroking the rest of me. I groaned and grabbed her breast, feeling her moan into my cock as Molly licked her closer to another orgasm. She started to lose focus on the blowjob she was giving me as she came, but there was something incredibly hot about feeling her edge closer to orgasm while I was inside her mouth. After another few seconds, she opened her mouth around my cock to moan as her body convulsed and Molly grunted in satisfaction.

College friends (FF) drag [M]e off to unexpected threesome – Part 1 [FFM]

*This is the true story of the first hookup between members of a college comedy group: me (Scott), my good friend Erin (the “one who got away” for reasons Part 2 will make clear), and Molly (our slutty, up-for-anything mutual friend). All of this unfolded at a large(ish) public university on the west coast, circa April or May 2007. Everyone involved was 21 years old. Will write Part 2 (and additional stories) if people like it.*

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“Come home with me.”

My friend Erin just turned to me and blurted this out in front of everyone, while the cast party was winding down.

“What??” I was a little drunk (well, we all were). So it took a moment to register. “You mean, like—”

“Yes. Come home with me.” She took my hand as if to drag me back to her apartment.

I looked up at my friend Jackson, who’d heard the exchange through the din of the party. He raised his eyebrows.

Still, I knew what I had to do.

“I can’t, Erin—you know this would just ruin our friendship.”