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Dating Disasters
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Straight Male / 52
The Hooker Wanted To Date
This was back when I was 28. I was in Florida in a hotel and alone. I called an escort service they sent over a really nice looking, tall, blonde with DD cup tits that stood out firm, a great ass and blonde hair on her pussy too. She had beautiful legs and a beautiful face. She didn't mind spending extra time, we talked a while, naked though and after she got her money. Then she sucked me hard I was fucking her trimmed blonde haired pussy and she was getting really wet. She let me suck her tits and knowing hookers don't usually let johns kiss them I did and she accepted. I told her she had the prettiest ass I'd seen in years and asked if she did anal. She said she did it a couple of times with her ex husband in the shower and it hurt her, but she'd try.
During our talk while fucking her, she mentioned she'd not mind seeing me on a personal level. This persisted while I buttfucked her. She didn't charge extra for the buttfuck, and gave me her real name and personal number. I agreed to call her for a date. The first date we had to push off a couple of hours as she met me at the restaurant after she went on a call.
As she said, unknown if it was true or not, I got her on her first day as a prostitute and was only her second. I asked if any of the guys she was with during the two days before we met up again had done anal. NO was the answer, followed by "that's only for you". We talked, I got her history, married, divorced, fucked by 5 guys before her husband and he let 3 others fuck her during their marriage. They had two kids, a son and daughter, 10 and 11. She was 34. After I dropped her off at her house, she offered for me to come in and I didn't go. Two days later, it was a repeat only I was genuinely interested in what the johns did to her and she to them, I got a full explanation. The end of the night I kissed her and rubbed her butt while doing it in front of her house, and closed the door behind her.
The next morning she called and asked if I didn't want to have sex with her because she was an escort. She said that she didn't expect to be paid as we were dating. I told her I assumed that was the case, and like most dates after we got to know each other and like each other we could have sex. She said she liked me and asked me the same. I did like her, so it was established that I'd have sex with her after our date that night.
We had sex, over and over again, I especially liked her telling me about her outcalls when she was naked in bed with me. She was a great sex partner, loved all the things I did, swallowed, offered her pussy anywhere I wanted, her ass was totally mine. Then the weird things started happening. At least weird to me. When her kids were around she didn't close the bedroom door, didn't close bathroom doors, she and even they at times would walk through the house naked at times. One time the kids were watching a show on TV, she and I were lying on the couch naked, I got aroused and wanted to go to the bedroom to fuck, and she pulled me on top of her there. She wanted me to fuck her in front of the kids. She explained that she and her ex did it all the time. With them glued to the screen I fucked her. Then a few days later I was buttfucking her on the living room floor, and her daughter stood next to us and watched, asking her mom if that hurt her, asking if I was in her "booty, or her cooch"
That was the last straw. I couldn't take it. I really felt that no kids should see their mother sucking, fucking and buttfucking out in the open. I left and came back to my home base and found a sane girl who didn't have kids, wasn't divorced, and wasn't a prostitute. Married now with kids, she and I have a great sex life, in the privacy of our bedroom when the kids are around.
During our talk while fucking her, she mentioned she'd not mind seeing me on a personal level. This persisted while I buttfucked her. She didn't charge extra for the buttfuck, and gave me her real name and personal number. I agreed to call her for a date. The first date we had to push off a couple of hours as she met me at the restaurant after she went on a call.
As she said, unknown if it was true or not, I got her on her first day as a prostitute and was only her second. I asked if any of the guys she was with during the two days before we met up again had done anal. NO was the answer, followed by "that's only for you". We talked, I got her history, married, divorced, fucked by 5 guys before her husband and he let 3 others fuck her during their marriage. They had two kids, a son and daughter, 10 and 11. She was 34. After I dropped her off at her house, she offered for me to come in and I didn't go. Two days later, it was a repeat only I was genuinely interested in what the johns did to her and she to them, I got a full explanation. The end of the night I kissed her and rubbed her butt while doing it in front of her house, and closed the door behind her.
The next morning she called and asked if I didn't want to have sex with her because she was an escort. She said that she didn't expect to be paid as we were dating. I told her I assumed that was the case, and like most dates after we got to know each other and like each other we could have sex. She said she liked me and asked me the same. I did like her, so it was established that I'd have sex with her after our date that night.
We had sex, over and over again, I especially liked her telling me about her outcalls when she was naked in bed with me. She was a great sex partner, loved all the things I did, swallowed, offered her pussy anywhere I wanted, her ass was totally mine. Then the weird things started happening. At least weird to me. When her kids were around she didn't close the bedroom door, didn't close bathroom doors, she and even they at times would walk through the house naked at times. One time the kids were watching a show on TV, she and I were lying on the couch naked, I got aroused and wanted to go to the bedroom to fuck, and she pulled me on top of her there. She wanted me to fuck her in front of the kids. She explained that she and her ex did it all the time. With them glued to the screen I fucked her. Then a few days later I was buttfucking her on the living room floor, and her daughter stood next to us and watched, asking her mom if that hurt her, asking if I was in her "booty, or her cooch"
That was the last straw. I couldn't take it. I really felt that no kids should see their mother sucking, fucking and buttfucking out in the open. I left and came back to my home base and found a sane girl who didn't have kids, wasn't divorced, and wasn't a prostitute. Married now with kids, she and I have a great sex life, in the privacy of our bedroom when the kids are around.
- That's Juicy! 26
- Remove It! 3


