This happened about 5 or 6 years ago (the ages were accurate for those times). We were working for a small startup, underfunded and overworked. Stephanie was hired on part-time to basically run errands and support anything we needed – front office stuff – follow ups on contracts, sales support, there were only about 7 of us working in an office so it was a tight knit group. Stephanie was 4’11, maybe 95 lbs soaking wet (get into that later), and had nice 32B breasts…a little spinner, even after 2 kids. Blonde, sunkist, and a
One night at a happy hour we all went out, had a few drinks, and she was a little flirty. Didn’t think much of it, but she told me that night that her marriage fell apart because she was tired of her husband, and decided that cheating was the easy way out, so she found a little summertime fling, and purposely got caught. Woof, a lot to take in, but clearly she was telling me for a reason.
We saw each other almost every day, and kept everything casual. When I was on the road, she would text me funny memes, maybe something she cooked up, whatever…it was all very ‘innocent’, but after a few too many one night, I told her that when she texts late at night, food isn’t what I want to be looking at. She started flirting back, but she wouldn’t send anything more than just some messages with innuendos. I knew at that point, that at our upcoming trade show in 3-4 weeks, would be the right time to make a move.
Queue the big show, and when I checked into the hotel, I got upgraded to an executive suite, because of my status and extensive travel. Running around getting everything set up, we had a pretty successful start to the show. The whole team went out for dinner and drinks to celebrate. She sat next to me, and I put my hand on her bare thigh. She looked at me dead in the eyes, and whispered into my ear: “Why don’t you just fuck me now.” Clearly I couldn’t do that, but I moved my hand away so no suspicion would be had.
We left the restaurant and the team went for more drinks, while Steph and I left to go back to the hotel. We opened the door to my room and I immediately lifted her up, kissing and making out frantically. We sat down on the couch with her grinding me, while I undid her blouse and bra. Licking her perfect nipples she reached down and grabbed my hardening cock. I got up, and she undid my belt and lowered my pants, my cock springing to attention. It was the size of her entire head, and she looked in disbelief. I sat back down and she immediately started going down on me, licking and sucking the head the best she could. After a few minutes she was roaring and ready, and raised her skirt and lowered her soaking wet pussy down onto my cock. The sound of her groaning and moaning filled the room as she absorbed my whole cock in one fell swoop…”this is the biggest I’ve had”…”oh god…yes…”over and over. I grabbed her hips as I arched to get deeper in her, which made her wild. She came…hard…legs shaking…grabbing her head…it was almost like she never cum that hard before.
I noticed that the suite had a jacuzzi tub, so I went over to turn it on while she recovered. As the water was filling the tub, she got on her knees and starting licking my cock clean of her juices. A mirror was in front of me and so I turned her around, bent her over, and started pounding from behind. She was in heaven, more and more moaning from pleasure. I grabbed her hair and pulled it up so she could watch me pound her from the back, and she was quickly turned on and pushing back against me. Her pussy was so wet, the skin on skin clapping of my balls against her clit, she came again…just in time for the jacuzzi to fill up.
We got in, and I massaged her clit to help her come down. Eventually, we got out of the tub (bad for lubrication), and went back to the bed. She got back on top of me, and started riding as hard as she could…she wanted me to cum…begging for me to cum inside her… I felt myself building up, and she was working harder and harder, grinding more and more…I told her I cum a lot, and within a minute I grabbed her hips, and started pumping the hardest I could, looking to fill her with all of my seed. At the point of no return, I arched my hips and pulled her down on me…my cock started spurting rope after rope of hot cum and her screams of “oh god, oh god, you’re too big” was drowned out by my grunts and groans. I felt like I had cum for an eternity; when I finally stopped, she spilled over to the side of me, panting…there was a pool of my cum spilling from her. She snuggled up close to me…and started playing with my cock and whispering dirty talk to keep my cock hard…
We went for two more rounds that night. (oh to be young again), and ended our fuckfest at 3am. This was the start of our summer fling, and things got hotter and hotter.
Source: reddit.com/r/gonewildstories/comments/jmxmkd/the_time_i_m34_awakened_my_coworker_f39_sexuality
Great story
It was the size of her entire head?