She was 18, new hire. Found out she was preggo, BF left in a hurry. I fucked her a little, then on a trip, got that virgin, preggo asshole popped.
Dani was just 18 when I hired her I was 30. She was my assistant. She was a plain jane looking girl, slightly chubby body, nothing really spectacularly hot about her. Within a month she found out she was 2 months pregnant, her boyfriend left her and left town. She was a mess, crying always, found out her parents called her a whore, and were kicking her out of the house. She made enough money for a place but was worried about after the baby and how she’d work and still take care of the kid. I was comforting, and working late nights, we had plenty of alone time. Eventually we ended up with her 4 months pregnant giving me blowjobs, then I stripped her laid her down on my couch/bed and ate her preggo pussy. It was then that I fucked her too. It was my first pregnant pussy and I liked it. Her tits were super firm now, she was normally a B cup but was probably approaching a C that barely moved. I fucked her a lot, got bj’s and ate that pregnant pussy a lot too. I tried to get her to give up her butthole to me, but she said she’d never done that and didn’t want to. I kept going with her, and one day out of town in a hotel I made sure we had a king bed, and told her how it would be.
She was to be naked the entire time we were in the room. I made her open all the drapes to the floor to ceiling windows so everyone in the neighboring hotel tower could see in. Lights on, I fucked her pregnant cunt over and over, ate her, she gave me BJs and the times we had room service I made her answer the door and sign for it. We stayed a week after the meetings were over, and I took her out to a nice dinner, only wearing a super slutty (yep even preggo) short skirt, no underwear and a thin white blouse that let her now fully C cups with the dark nips show through. Her big belly showing above her dress and below her blouse she was so embarrassed. I took her after dinner to an adult bookstore and made her get naked so the guys at the gloryholes could look at her, and several reached through to feel on her cunt, butt and tits. I told her she had a choice, walk back naked and keep her asshole virgin, or walk back in her clothes and let me buttfuck her.
On the way back I made her stop in a pharmacy and ask the man behind the counter if KY was a good brand for her first anal sex. She was do embarassed but by this time I knew she’d do anything for me.
Back in the room, she stripped, opened the drapes, and lubed my cock, lubed her asshole and bent over, her hands on the table in front of the window, her face looking out so everyone could see her reactions to my cock going into her asshole. I watched her wincing in the reflection of the window. For the next three days, I buttfucked her only, she got very used to it quickly. Within two weeks she actually came from getting it.
After the baby, she couldn’t fuck for 6 weeks, but her mouth and her asshole were used a lot. After the baby weaned, I kept her milking. It’s been a year and her tits still need draining twice a day. I want to see her get pregnant by someone again, and start it all over again.
