[MF] Coworker wanted me to cum inside, she didn't realize she forgot her pill...

I've always gotten along very well with everyone at work, and especially this one girl I'll call Violet. She's 29, a year younger than me. She's Hispanic, black hair, brown eyes, and a phenomenal sense of humor both at work and outside. Just genuinely one of the best kinds of people to work with. At the time I met her she was a little thicker than she is now, but not a lot.

When she started with the company I checked her out and tried to make a move only to find out she was in a fairly serious relationship. When I was younger I might have ignored that but I'm older, wiser, and care more about this job than any others in the past, so I was respectful. I wouldn't say we became good friends, but we got along well enough that working on projects with her is always a blast.

When it came time for this one conference I go to every year, my boss finally allowed me to pick another person to go with me. I considered a few names but ultimately decided on Violet. She was in a department that would benefit from the conference, good learner, good at networking, and just overall the perfect candidate. My boss approved, and she agreed, so it was set.

This was her first time going on any sort of work trip, so we scheduled a few meetings to go over everything, who we should try to network with, yada yada boring business stuff. The Friday before the conference, one of those meetings ran late so we decided to go get dinner and drinks after. I pulled into the parking lot just before her and took the last spot, forcing her to park on the street. I got out and waited for her.

"I realized after the fact that that was kind of a dick move," I said.

"Yeah, what the hell, man. I had to walk a whole extra, like, 20 feet," she teased.

We approached the bar and I opened the door for her with a bow. "I've gotta make up my gentleman points somehow." She laughed and thanked me. When our beers arrived, she jokingly acted like she was going to tap her bottle on top of mine to make it fizz, but stopped and we clanked them together instead and drank.

"My parents still talk about you all the time by the way," she said. I spent one night talking with her dad at a Christmas party two years prior and instantly became his best friend. "He keeps talking about wanting to hang out with you again."

"Tell him I'm free whenever," I said. "I have no life these days so hanging out with my coworker's dad sounds like a wild night."

She laughed. "Hey, my idea of an exciting night lately has been drinking wine and watching reality TV so I get it."

"Boyfriend's not taking you out on any hot dates?"

"What? No. We broke up like a year ago. You didn't know?"

"I didn't, honestly." I should've seen it earlier. She'd been spending more time on her appearance, lost a fair amount of weight, and was spending more time at work. All the signs were there, I had just ignored them out of respect.

We enjoyed the rest of our evening, and flew out to New Orleans the following Monday. The whole flight out, I couldn't stop thinking about her. I could try to make a move, or I could not. I decided to play the middle ground and just be friendly. The next morning, I found her in the breakfast hall.

"Were you planning on doing the networking dinner tonight?" I asked.

"I mean it's free dinner and it's not like I had anything else to do..."

"I've got my finger over the button to buy two tickets to the Pelicans game tonight. Front row, center court, camera behind us on the off chance the boss decides to watch that game."

"What? That's gotta cost a fortune."

"Because you're used to Lakers games where you have to know Jack Nicholson himself to sit that close. These are nothing compared to those." I'm not the biggest basketball fan in the world but I knew she was, and I honestly couldn't pass up such good tickets for a reasonable price. Like I said, we weren't getting those back home.

"Yeah, sure, sounds like fun."

I bought the tickets and we went about our day normally. We snuck out of one of the afternoon sessions so we could Uber to the arena.

"Needless to say, this is all going on my card, not the company's," I joked.

The seats were frankly amazing, and it ended up being a pretty exciting game as well. We had some beers and got really into pretending like we were the biggest Pelicans fans in the world.

I tried to be good and not make any moves. I figured if a sign presented itself to me then I would take it, otherwise this was just a friendly outing among coworkers. During one of the breaks in action, she got bored and laid her head on my shoulder. There it was. I put my arm around her until the game started back up.

We Ubered back to the hotel after the game and I stopped in front of the store on the ground level. I looked back at her as she kept walking a few steps in front of me. Seeing her from behind, this was the first time I had truly taken note of her body in a while. Her black hair flowed down her back. She wore a tight gray shirt tucked into black jeans, showing off her subtle hourglass figure. She turned around when she noticed I had stopped.

"What are you looking at?" she asked me.

"I was thinking of grabbing a bottle of wine if you wanted to keep this party going a little longer," I said, pointing into the shop.

"Oh, I don't know. I..." Her voice trailed off as she thought twice about it. "Yeah, sure. Why not?"

We walked into the shop and picked out a bottle that looked good. I've never been much of a wine guy, but she knew what sounded good so I trusted her. We headed up to my room to drink.

"Oh you got the two queen beds as well," she said. "I wonder why they didn't just save the money and book us together."

"They probably had a good reason for that," I said. "It starts with Human and ends with Resources."

"That's true. I mean, our chat logs at work are enough to file a complaint over if they ever read those," she said.

I poured us each a glass, we toasted, and drank. We laughed about work, the conference, and the game.

"I'm honestly just glad they approved a second person this time," I said. "Normally I'm alone and these are very boring."

"Oh come on, I bet you've tried to hook up with at least one girl at one of these things.”

“It's usually just work then sleep,” I said. That wasn't totally true, but she didn't need to hear that story. “But now I have someone here who can sleep in the other bed.”

 She laughed and finished her glass. "Well I've got two beds of my own to get to," she said. She started to slowly push herself off the bed, staring at me the whole time.

"Hold on, hold on," I said, grabbing her arm.

"Oh thank God," she said, sitting back down.

"Look, I'm usually very careful because I don't wanna make shit weird at work, but you definitely have a thing for me, right?" I asked.

"Wow, so forward all of a sudden," she said. "Why should I answer that when you ignore me at work all day?"

"Because I've got a thing for you and don't wanna show it."

She looked me in the eyes and said, "yeah. I like you too."

I leaned over and kissed her. When she kissed me back, I leaned in closer to kiss her deeper. I placed my empty glass on the bedside table and got my hands into the game, one around her back and the other on her thigh. I helped her take off her tight gray shirt and throw it on the ground. She wore a black bra that held up her large tanned tits. I touched her tattooed arm and admired the work for a moment before I removed my coat. Soon we were undressing all the way.

"Wait," she said. I stopped, completely naked. "You're clean, right?"

"Yeah you?"

"Yeah."

"Okay good," I said, then stopped again. "I don't have a condom."

"I'm on the pill."

"Oh good, we're clear for takeoff," I said. "Get up on the pillow."

She moved up on the bed and I put my face between her legs. I’m the kind of guy who likes to take this moment slowly, gently teasing her by dragging my finger around the edges and kissing her inner thigh. From the way she was moaning and squirming, I could tell she was enjoying it and yet still craving to be touched so bad. When I finally allowed my tongue to lick her, she let out a loud moan that told me everything felt amazing. I stuck a finger in her pussy and could feel as she tensed her muscles around it. I could tell she was going to be very tight, and would need to be extremely wet for me. I kept working on her until she patted my head and told me to switch. I laid down and she got down at the foot of the bed to lean down and suck my cock. She was incredibly skilled and moaned as my cock filled her mouth. It twitched a bit from excitement, causing her to jump.

"Oh shit, I thought you were cumming," she said.

"Wow, such low expectations from me," I teased. "I would let you know."

She slowly put it back in her mouth and started to suck the life out of me. I threw my head back in ecstasy and grunted. When I looked back down, I saw her big brown eyes looking up at me and a faint smile on her face, at least as much as she could smile with her jaw wide open around my cock. We locked eyes and she quickly looked back down and focused on her work. I reached my hand out and held her head in it.

"Look at me," I said. She obeyed. We locked eyes once more and held it for the duration of her blowjob. I grunted and moaned as her head bobbed up and down in my lap, licking up and down the shaft. Every time a bit of precum dribbled out of the tip when her mouth wasn't on it, she was quick to lick it up.

It was around that time my phone started to ring. It was the boss.

"Oh shit," I said. She stopped and I showed her who it was. I picked up and answered. He wanted a quick check-in after the first full day. 

"How has Violet been?" he asked.

"She was great, she's great," I said. I looked down at her as she slowly stroked my cock to keep it hard. "She's a hard worker and a real pleasure to have."

Thank God it wasn't a long call, and he hung up shortly after. I let out a loud sigh of relief.

"Turn around," I said. Staying on all four, she spun around to face away from me, her ass up in the air. I positioned myself behind her.

"Have you been working out? Your ass looks great."

"I have! Thanks for noticing," she said.

I grabbed my cock and penetrated her. My hunch was right, she was extremely tight, even for as wet as she was. I eased into her slowly, taking it a half inch at a time, letting my cock stretch her out. Once I was fully inside, I started taking longer and deeper strokes. She looked back at me with a look of desperation as if she was wanting more. I grabbed her by the waist and fucked her harder.

"That's it, right there, keep going," she moaned with each thrust. I listened, and kept going until I felt her pussy tighten and practically squeeze my cock out as she came. Her legs weakened and she collapsed on the bed. She took a moment to get her breath again, then flipped over onto her back.

I leaned down on top of her and slid back inside. Her tits were big, round, and firm. They bounced under her chin every time my cock pushed deep into her. When I got done watching them, I looked back at her face and saw her staring up at me with her big brown eyes once more. She bit her lip and moaned as we locked eyes for a third and final time.

"I'm gonna cum," I told her.

"Cum in me," she said. "I don't mind. I like it."

I broke our eye contact as I shut my eyes tight in concentration. I shot hot load after hot load into her pussy, then fell nearly limp on top of her as my cock kept dry-pumping inside her. I pulled out and my cum oozed out of her behind me. She stuck her finger in just to feel me still inside her.

We spent the night together in my room, and she got up early to go back to hers and get ready. When I met her in the breakfast hall, she looked concerned.

"I forgot to take my pill yesterday," she said. "That was fucking stupid."

A couple weeks later she texted me that she got her period, so there was some relief. We went out again after that to try and keep things going, but agreed that the vibes were off now because of that scare. We agreed that dating as coworkers probably wasn't the best idea at this point. Still though, I walk by her desk and see only three personal items: a photo of her dogs, and two gifts I've given her over the years. There might be more to this story some day, but for now, that's where I leave you.