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Dating Disasters
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Straight Male / 52
She Just Didn't Care
About 25 years ago I met a woman in an internet chatroom, honestly I don't even remember her name but let's call her Julie. She was about 5 years younger than me and from a poor part of town. We met in a sex chatroom so we knew we were interested in sexual talk or more, but from the moment we met it was clear we weren't really very attracted to each other. She was very slightly plump, but it was more that she was just plain, while I in turn clearly wasn't her type. Still, we hung out and walked around a park on a cloudy day, then sat a while on a picnic table. I remember her telling me a story about her and two girlfriends having sex with a guy they knew as a treat to him, she didn't reveal many details but it definitely turned me on. I got behind her on top of the table to rub her shoulders, she neither responded nor told me to stop, and after a while I asked her if this was ok. She said she didn't care, and that "when I'm not into something I can just ignore it." I asked if she did that on dates often, and she said she did, it's easier to just let someone touch her than stop it.
I said I didn't want to offend her and wanted to know what her limits were, and she just said her clothes have to stay on, but otherwise she didn't care. I confirmed that this could go as far as a guy getting himself off, and she said that happened and it's just "what they do" in her words. I took that as an ok, and started fondling her boobs and like she said, she just ignored me but didn't tell me to stop, she just kept looking out at the trees around us. No one was around and it was getting slightly darker, so I took a greater risk and pulled out my hardening dick, sliding it against her face. She didn't move at all, so I kept stroking and sliding more, while my other hand held the other side of her face. "Turn here" I said as I shifted her head slightly more to the right where my cock was pressing into her cheek, and she just let me move her head without resistance. The angle was still awkward but I was getting close so I stood up on the seat, feet either side of her hips, and held my dick right in front of her face, pumping into her tightly closed lips. She wasn't giving me any action, but the sight was incredible and I quickly started cuming over her face, barely able to keep my balance standing as I coated her face with white ropes of semen.
I sat down and rested, and she still just sat there expressionless. I thanked her, again without response. I finally asked if she wanted a ride home, though she had walked there and said she was less than 5 blocks away from the end of the trail, which wasn't far. She shook her head no, and got up. She walked passed my car, I said good night, she kept going. Never heard from her again.
I said I didn't want to offend her and wanted to know what her limits were, and she just said her clothes have to stay on, but otherwise she didn't care. I confirmed that this could go as far as a guy getting himself off, and she said that happened and it's just "what they do" in her words. I took that as an ok, and started fondling her boobs and like she said, she just ignored me but didn't tell me to stop, she just kept looking out at the trees around us. No one was around and it was getting slightly darker, so I took a greater risk and pulled out my hardening dick, sliding it against her face. She didn't move at all, so I kept stroking and sliding more, while my other hand held the other side of her face. "Turn here" I said as I shifted her head slightly more to the right where my cock was pressing into her cheek, and she just let me move her head without resistance. The angle was still awkward but I was getting close so I stood up on the seat, feet either side of her hips, and held my dick right in front of her face, pumping into her tightly closed lips. She wasn't giving me any action, but the sight was incredible and I quickly started cuming over her face, barely able to keep my balance standing as I coated her face with white ropes of semen.
I sat down and rested, and she still just sat there expressionless. I thanked her, again without response. I finally asked if she wanted a ride home, though she had walked there and said she was less than 5 blocks away from the end of the trail, which wasn't far. She shook her head no, and got up. She walked passed my car, I said good night, she kept going. Never heard from her again.
- That's Juicy! 22
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