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).

A couple of weeks in, we hadn’t “defined the relationship” or anything, but our agency’s work hard/play hard lifestyle didn’t really afford much opportunity to socialize with other people… and our sexual chemistry was so intense, we were eagerly exploring each others’ boundaries. In talking about our sexual histories, we’d each had threesomes in the past (the prospect of our coworker Ashley flashed across my brain when I contemplated a threesome with Cat… ) but neither of us had ever tried anal.

In her case, it was because she wanted to save something intimate to try with the right someone, someday. In my case, it was because past girlfriends had never been interested in trying it—and we’d had perfectly fulfilling sex lives without giving it much thought.

Also, my preference—and Cat’s—was that I cum in her pussy or on her face whenever we had sex. On a primal level, I preferred the feeling of pumping my cum deep inside her, but we both found it hot when I left her face dripping with semen, too.

One day, though, Cat surprised me after work by handing me a condom when I was just about to enter her.

“Sorry,” she said apologetically. “I had to reschedule the appointment for my next birth control shot, so it lapsed and we need to use condoms for a while.”

I was a little disappointed, naturally, but completely understood. I put it on, we fucked until I was close, and then I pulled out of her, yanked off the condom, and jerked thick ropes of cum onto her chin, her cheeks, her forehead. She scooped much of it into her mouth with her fingers and then started playing with herself. After a moment, I joined in fingering, licking, and watching her (both right in front of me and in the mirror over her dresser) as she came, too.

This was our “routine,” you might say, the next couple of times we fucked. Until that weekend, when we’d already had sex a couple of times in more or less the same way.

We were in her bedroom again, both of us horny. I put on another condom and walked around to the foot of the bed, pulling Cat down toward me as she giggled. She was naked and laying on her stomach, arching her ass up at me. From between her prominent labia I could see the pink insides of her swollen pussy—and, just above it, her tightly-puckered asshole.

I peeled Cat’s pussy lips open and nestled the head of my cock just between them as she moaned, slowly pushing forward until it was in up to the hilt. Even through the condom, she felt amazingly tight and wet, her folds gripping me, almost shimmering around me as she squirmed. I drew my cock slowly out and then plunged it back inside her, reaching up to grasp her breast and pinch her nipple as she bounced against me.

“Fuck, oh fuck me,” she was moaning. “You’re so fucking thick.”

I watched in the mirror as I worked myself in and out of her, feeling her lips grip me through the condom. Picking up the pace a bit, I started to slam into her, my balls slapping against her as we fucked harder and harder, Cat moaning—until, all of a sudden, I slipped out of her and we both gasped in frustration.

Before I could slip back inside her, though, Cat looked back at me over her shoulder and caught my eye.

“Put it in my ass,” she said.

“W—what?” I asked, genuinely unsure whether she meant it.

“You can take the condom off,” she said. “I want to try it with you. Put it in my ass.”

Cat half-crawled up to her bedside table and fished a small bottle of lube out of the drawer, handing it back to me before she settled back down into the same position—facedown on the bed in a prone position, her legs spread on either side of me and her pussy and ass offered up invitingly.

“Are you sure?” I asked, peeling off the condom and tossing it on the floor behind me. I opened the bottle of lube and looked down at her little brown asshole, knowing from our earlier conversation that no one had ever penetrated it before.

“Yes,” she insisted, arching her back to tease me. “Come on, Scott—fuck my ass.”

That was enough for me. Trying not to get everything sticky, I applied a few big drops of lube to my cock, now throbbing free of the condom, and stroked myself to coat it nicely, leaving a little extra for my tip. Since both of us were anal virgins, we didn’t do any additional prep (which turned out not to be the best idea).

Gently, I placed my lubricated cockhead against Cat’s anus and began to push forward. She moaned as I worked it slowly inside her, watching her open up for me, until she started to grit her teeth a bit—at which point I held still for second and then slowly eased the pressure. After a second, I increased it again—and thrust a little deeper—as she got more and more used to me.

The sensation was unlike anything I’d ever experienced. Her ass felt so tight around my shaft, and yet I could penetrate so deeply, pushing past where her cervix would’ve been if I was fucking her pussy.

I thrust all the way inside and held myself deep in her guts for a long moment, feeling her asshole stretch to take my girthy cock, her muscles quivering around me as she took me for the very first time, her tight rectum squeezing the base of my dick, right up against my balls, as I pulled her hips into mine and drove up into her pelvis from behind. After a long pause, I drew my entire length slowly out and then pushed all the way in again, the juices (and lube) that coated my cock beginning to make each thrust feel smoother as I built up a steady rhythm. I looked up, watching in the mirror—and catching Cat’s eye.

She was watching us in the mirror, too—staring at the spot where my dick was disappearing into a hole no one had ever penetrated before. She moaned and started to relax a bit as she grew accustomed to getting fucked in the ass, so I picked up the pace.

Ordinarily, there’s something I find incredibly hot about bottoming out inside someone’s pussy (especially raw), knowing I’m fucking, claiming, pumping my seed into the most intimate, innermost part of a woman. Having never tried anal before, I was incredibly turned on to discover a similar feeling about taking Cat’s ass—knowing mine was the first cock ever to press inside of her anus, let alone penetrate to depths she’d never felt before. The filthiness, the forbidden-ness, the raw animalism drove me wild. And soon, the feeling of her tight ass gripping my bare cock was starting to push me closer to the edge.

“Oh my god, Cat, your ass feels so good,” was all I could manage to gasp out. “I’m gonna cum soon.”

“Yes, Scott,” she moaned as I railed her. “Cum in my ass. Pump it into me.”

I could feel my balls tighten. Below, I could also feel Cat rubbing her clit furiously and occasionally slipping a finger into her pussy while I fucked her in the ass. In the mirror, I saw her eyeing me intently, eager to watch me cum, one finger and then two stuffed inside of her pussy while I buried myself as deep as I could go—and that was enough to send me over the edge.

I pulled Cat’s hips into mine just as I felt my cock spasm and begin to pump a massive load of sperm into her. The pressure caused Cat to involuntarily clench her asshole at exactly the right moment, clamping down just as I started to cum and taking my orgasm to the next level. We fit together so tightly, and I was so deep inside her, I knew she could feel every twitch, every spasm that disgorged more semen into her depths, and I in turn could feel her moaning from deep inside her.

For a second, I was utterly spent and a little dazed. Then I felt her continuing to rub her clit and finger her pussy, subtly grinding into the hand she’d sandwiched between her prone body and the mattress. So, in hopes of helping her cum before I went flaccid, I started to very gently fuck her again—really just varying the pressure of my cock inside her ass in a way she seemed to find pleasurable—in time with her bucking hips.

Fortunately, she was already close. Her breathing was ragged and she started to buck her hips more forcefully now. I was still decently hard, so I built up my rhythm accordingly, driving her closer and closer to the edge.

“Oh fuck, I’m so close,” Cat moaned. “Fill me, stuff me—oh my god, I’ve never felt so full. Oh, fuck—”

And with that, her asshole clenched the base of my cock HARD, and she came—a full body orgasm that left her breathless and incoherent for a second, splayed face-down in a pool of sweat and semen on the bed. I collapsed on top of her and we lay there together, breathing in sync with one another, until I felt myself soften to the point that I knew I’d have to pull out.

Sitting up, I gingerly withdrew my softening cock from Cat’s asshole, watching it emerge glistening with lube and cum. Most of my semen was so deep inside of her it showed no signs of dripping out, but I used my tip to rub some against her as I pulled out the rest of the way, leaving a streak of my creamy white against her puckered hole.

“Holy fuck that was hot,” she said as I laid down beside her. “Did it feel different than my pussy?”

“Very,” I said. “How was it for you? Did it hurt?”

She shrugged.

“A little, when you were first going in,” she said. “But I liked the pressure once I was used to it. And I loved making you cum inside my ass—that alone was worth it.”

A day later, though, our lack of anal experience (and preparation) would come back to bite us. Although Cat had initially been totally fine, by the next day she was feeling extremely sore—to the point where it was painful to sit down. I’m sure, in our spontaneous desire to try something new, we rushed it and accidentally hurt her (and maybe even tore something) in a way that was completely avoidable.

The good news was that she started feeling much better quickly, so we didn’t do any serious or permanent damage. The bad news was that we did anal only one other time (while she was waiting on her next birth control appointment) and then it was back to regular sex.

Any interest in one or two more Cat stories? There was a pregnancy scare during this same period (while waiting for her next birth control shot) and one other episode I’m thinking about writing up.

Then, of course—years later—there was the time I matched on Tinder with her younger sister…

Thanks for reading/reacting!

Source: reddit.com/r/gonewildstories/comments/vicslj/spontaneously_trying_anal_with_my_coworker_f