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NSFW: yes

Stephanie and I used to work together for a couple of years, and often chatted about numerous 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 clever 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 at all times wondered that she never was too interested in dating and I was convinced that she must be rather boring in bed.

At some point, she got married though, and got pregnant after a few months. I normally don’t have a particular thing for pregnant women, but as her belly started showing, I caught myself looking more and more often at how her small breasts grew, or how she put on just enough weight on her butt and thighs so that her forms started to look a lot more feminine. She was about six months into her pregnancy when we had this business event with dinner, drinks and whatnot. Stephanie didn’t drink of course, but we talked a lot, had some good laughs until we noticed that most people were gone. The conversation turned towards sex, and she shyly admitted that even before her pregnancy, their sex life with their husband was quite scarce, and since she got pregnant, he barely dared to touch her. I didn’t intend to, but as I had a few drinks, I blurted out that I had this inexplicable fantasy of having anal sex with a pregnant woman. She looked down, blushed and didn’t say anything, and I regretted mentioning it immediately, but at the same time I could also see that I planted a wondered in her head. I was a bit afraid that I went too far and soon called it a night.

In the following days I was a bit more hesitant to approach her than before, but she came up to me to chat as if nothing happened, and appeared to be even more flirty than before. She mentioned that her husband would be away for the weekend, and I casually invited her over for Saturday afternoon so that she wouldn’t be alone. She came over, wearing leggings, a loose dress and sports bra underneath. I made a virgin cocktail for her, popped a beer myself and we started chatting as usual. Pretty soon the conversation turned to our sex lives, me admitting that I had my fair bit of fun, but was currently enjoying being single. I also told her that earlier I wondered that she wasn’t very interested in relationships or sex. She laughed it off, saying ‘it’s at all times the quiet ones, aren’t they?’. She said that she indeed had less experience than she wanted to, but she was hoping that with her husband she could try new things. However, that was not the case apparently, and since her third month of pregnancy, he didn’t even dare to touch her. After some more talking, she brought up my remark from the other night and asked whether I was serious about it. I said that I indeed did have an occasional fantasy about it.

To my surprise, she stood up and started undressing, saying ‘So what if I fulfilled your fantasy, and you could help my frustration?’. I hesitated for a moment, watching her dress fall on the floor, and her starting to pull her leggings off. ‘But you have to promise you’ll be careful, I never had anything back there…’ she said, then pulled her sports bra over her head. Her breasts were larger than I expected, full and perky, with pink, puffy nipples. She moved to my bed, laid her glasses on the nightstand, then laid down. I followed her, tossing my shirt on a chair and pulling my trousers off. I opened the drawer and pulled out a large jar of lube, then pulled my underpants off, exposing my half hard cock. Now I have to say, I’m not massive, but somewhat larger than average, and definitely thicker. She looked at it and gasped ‘Shit, is that going to fit?’ I assured her that it would and that I would be careful, then laid down next to her. I started softly caressing her belly, then her breasts, noticing that her nipples were very sensitive. We started kissing and she was softly stroking my cock, while I moved my hand over her butt and started pulling her towards myself. Then she asked whether she could taste me a bit and I nodded.

She turned around so we were lying next to each other head to toe, and started licking my cock before she took the tip into her mouth. She definitely didn’t have a lot of experience as she was rather giving tongue kisses to my cock than sucking it, but it still felt nice and got me hard. In the meantime I pulled her panties off, took some lube and started playing with her asshole. She sometimes let out a small moan as I circled and probed her virgin hole, then a bit later pushed one finger inside while she kept making out with my cock. After a short while she turned back and lay on her side with her back towards me and asked ‘This way? I mean, I cannot really do it any other way with my belly and all…’ I took a generous amount of lube and smeared it on the full length of my cock, then took some more and brought my hand between her cheeks. I guided the head of my cock to her ass, then put my hand on her hips and started pressing into her until I felt the tip of my cock enter her. She gasped, but remained silent otherwise. I stopped and asked whether it hurt, to which she answered in a muffled voice ‘No… I mean yes, but… just keep going’ and I felt her pushing back against me.

I gradually pushed a bit more than half of my cock in her tight butthole when she let out the first really loud grunt. I stopped, concerned that I’m hurting her, but she almost immediately said ‘Don’t. Fucking. Stop’, so I started pumping into her while holding on to her hips. She kept silent again for a while, grabbing onto a pillow and only allowing herself some muffled voices before letting out a loud cry again after a bit. After each cry, she said things like how she has never felt so filled before, to which I told her that I was only halfway in. She went crazy after that, reaching down between her legs and rubbing her clit while pushing her hips back against me as I kept fucking her. Soon after she came very intensely and loudly, lasting for a good half minute. When she started to calm down a bit, she told me to go all the way inside her.

I got some more lube, hastily smeared it on my shaft and started pushing myself in, pulling her buttock up so I can get even deeper. She was biting on the pillow and groaning as I started moving inside her, balls deep in her ass now, and she soon started to rub herself again. It took a few minutes to reach her second orgasm, and this time her frantic sounds and the sensation of her convulsing body brought me close to climax too. I fucked her through her orgasm and then released a massive load of cum deep into her ass. We lay there panting for a minute as I was getting soft inside her, then pulled out and we both rolled on our backs. I noticed how bright red her face was. We talked for a little before she noticed that my cum was oozing out of her ass and got up to go to the bathroom and clean herself up.

She started getting dressed when she returned, looking incredibly satisfied but at the same time a bit confused too. She left and later that evening I got two texts from her:
‘Thank you for keeping me business’
‘This felt fucking amazing, I can still feel it’

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