When I had sex with my pregnant colleague at a work award night. [MF]

The story of the most intense, wild sex I’ve ever had.

I [33M] met Jessie* [33F] in 2015. She is what most people would call a pocket rocket in every sense of the word. 5’2, blonde, petite, boundless energy and just about always the strongest willed person in any room. I met her when we applied for the same Branch Manager position at the bank we work for. She got the role but I got an adjacent role that opened up during the recruitment process. We went off to training together at a city a few hours away from ours and while there got to know each other. We were a similar age, both relatively newly married and ambitious with our careers. Nothing happened on that trip beyond getting to know each other, some fun drinks and some light flirting but I’d be lying if I said I didn’t fantasize about what she wore under her blouse and pantsuits.

As we took up our roles we stayed in contact, venting to each other, sharing struggles and helping each other work through work problems we had. We would see each other from time to time and always had a very friendly relationship, going from handshakes to hugs and a peck on the cheek for greeting and farewell.

Fast-forward to late 2018 and I had moved on from the manager position to become a lender based at two branches and I was very happy to find out one of them would be Jessie’s. She ran a good business so I knew it would be great for my KPIs but I was also very happy to get to work more alongside her. Working together we got closer and started to talk more personally, even talking about relationship and marriage things.

Early in 2019 was when she let everyone know she was pregnant with her first child, that is when I noticed a change in how she treated me. Suddenly I found her being way more touchy feely when we spoke and far more forward in talking about her body. What would have previously been a chat about how our work was going would end up with her putting her hand on my leg or with her leaning against my shoulder. I put it down to her being pregnant so matched her level of physicality, sometimes squeezing her leg and pulling her in close if she leant on me. I didn’t want to push my luck but it absolutely turned me on, as did the fact her little breasts were getting plumper by the day and her clothes tighter as well.

Around the same time the branch she managed and I got invited to a state awards night that would be an overnight trip with a big gala dinner. The thought of a trip away with an empty hotel room, a party atmosphere and the extra physicality she’d been displaying had me very excited.

The night was great fun, we ultimately didn’t win any awards but the free alcohol flowed and dance floor packed out. It was a great celebration for the team that had worked hard but Jessie and I kept finding each other on the dance floor, twirling around and casually rubbing up against each other. Even with her pregnant belly popping out, her pink dress barely holding her breasts in, she refused to leave until the very end, she said she wasn’t going to let being pregnant stop her and she willed herself to the end.

Instead of waiting with everyone else and catching a packed shuttle bus back to our hotel we decided to walk the kilometre or so. I don’t know how Jessie had it in her but she decided she would do the whole thing still in heels. As we walked we chatted and laughed about the night, with a few hundred metres to go her heel hit a crack in the pavement, she stumbled and I caught her grabbing her arm and waist. We had danced together already that night but I still remember the electricity in the air when I held her, my hand against her tight dress could feel the contours of her waist and I held on for longer than need be. We looked each other in the eyes and for a moment I thought I should kiss her then and there but instead we laughed.

As we got closer to the hotel started to say her feet and legs were tired so I flippantly offered her a foot massage. It was a big step, while we had been close at work, going into her hotel room, doing something obviously sensual was new ground for both of us.
“That would be amazing actually” she replied.

We made our way up to her room and she lay down on her bed, still in her dress. I sat at the end of her bed, she closed her eyes and I started rubbing my thumbs firmly around her feet. I like to think I give quite good foot massages, focusing on the balls of each foot, then the arch and then the back of her ankle. This one felt extra charged too, each time I shifted position I could feel her tense up and my heart was beating so hard I felt like she could probably hear it going.

All pretense was dropped when I finished her second ankle and asked “should I do your legs too?” As I shifted position and pulled up one leg her dress rode up and I saw her red boy short undies. She made no attempt to fix it and that just turned me on even more. I can’t imagine by this point she hadn’t noticed the growing bulge in my pants either as I moved my hands down her legs, firmly rubbing her calves, around her knees and then finally her thighs.

As I got to the top of her thighs she really started to breathe quickly. I had moved to the side of her bed and she finally reached over and gripped my own leg, digging her nails in. I looked down at her and finally lent in and kissed her.

That first kiss was hard and intense, lips locking, tongues immediately entwined and I immediately moved one hand over her slightly wet panties, rubbing around her clit. That got her biting my lip and she moved one of her hands around to my cock. We didn’t need words, we knew what was happening.

With one hand she undid my belt and fly, I helped her, pulling my pants and briefs down, exposing my hard cock. Still standing next to her, she turned her head and guided my cock into her mouth as I pulled her panties aside with one hand and with my other started to squeeze her pregnant waist. Honestly the energy in the room was so high I could have probably cummed in her mouth within a minute at this point but I held off, pulling my dick out of her mouth and told her, “I wanna fuck you Jessie”.

I moved onto the bed, taking my shirt off as I went, pulled her panties off, grabbed her waist and years after meeting her and thinking about it, spread her legs and plunged my cock into her pussy. The feeling was incredible, even my best fantasies hadn’t prepared me as I pushed myself all the way in. Instead of pumping back and forth straight away I swiveled my hips, moving myself around while I was deep inside her, she moaned deeply as she arched her back gripping the bed sheets.

I leaned forward and pulled her pink dress off her shoulder exposing her breasts. She was a small girl but pregnancy had treated her boobs well. Looking down at her I couldn’t help but take in the sight of her, skirt hitched up above her hips, legs splayed out, myself in between them and boobs bursting out of the top above her pregnant belly. It is an image that I have stored in my mind to this day as one of the sexiest moments in time I’ve been part of.

I moved down and passionately started kissing and sucking on her dark brown nipples. Jessie’s hands gripped my back tightly pulling me closer as I began to thrust hard.

“You’re so fucking sexy Jessie”

“Fuck me now, harder, harder”

She wrapped her legs around my body as I got closer and closer to climax. I’d normally try to last longer but I was so in the moment and we had so much build up that I could hardly control myself. Her body arched and I could feel her pussy tighten around my cock and she moaned in ecstasy.

“I’m gona cum Jess”

“Go now”

The combination of her super sensitive pregnant body and the intensity of going behind everyone’s back meant we didn’t last long at all that first time. I exploded inside her as she moaned her way through.

I rolled off and we lay next to each other covered in sweat. Later after Jessie said she hadn’t had sex for months at that point so everything was super sensitive for her. For me it felt like a whirlwind of pleasure, I’ve never been so intensely caught up in intimacy, the combination of it being the first time and her pregnancy lit the air and ever touxh with electricity.

We had sex again twice that night and again in the morning. Since that first night we have fucked again a number of times but have laid out some rules to help make sure we don’t mess up the rest of our lives. We know how it could hurt our careers if it got out especially as we are expected to work together, and neither of us want our actual marriages to be split up either.

Still that time remains the most intense sex I’ve ever had. Feel free to ask any questions you might have about it in the comments or in a message.

*Name changed for obvious reasons.

Source: reddit.com/r/gonewildstories/comments/11g30bo/when_i_had_sex_with_my_pregnant_colleague_at_a