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Dating Disasters
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Straight Male / 55
Handicapped Date
25 years ago I had just turned 30 as I moved to a new city with no relationships in sight. Feeling a bit down, I tried a dating phone line and very quickly got connected with a woman in her mid-20s with a sweet voice who wanted to talk to me indefinitely. The time on the line was limited unless you paid more, so we exchanged numbers and called back to talk some more. She sounded very open and wanted to meet me tonight, but then said she had a confession: she had her right eye removed because of cancer and her socket was covered with skin. This understandably made her self-conscious and unable to date easily. She asked if I was ok with this, and I said I was so she soon gave me the address of the friend she was staying at and I drove on over.
Her older friend greeted me at the door of her apartment, she also had a male visitor who I gathered was a truck driver. She seemed very protective of her young friend, but also wanted to give her space for her own, so soon she and I went into the spare bedroom to hang out. We soon did some kissing and necking, and I got her shirt off to suck her nipples. We agreed not to have intercourse on our first date, but I asked what she thought of oral sex, and she said she was fine with giving it but "I don't like it when guys come in my mouth." I admitted that this was my favorite activity, but would respect her limits. I instead stripped her naked on the edge of the bed and kneeled in front to go down on her, which made her moan in pleasure and appreciation. After she came once I kept licking and she she didn't push me away, clearly wanting more. But soon she started asking if I could go inside her. I asked if that didn't violate our earlier agreement, but she pleaded with me saying she wanted it so much now, and finally said "I'll do whatever you want if you just put it in for a minute." I again asked if she was sure and she said she was, so I stood up and quickly slid in my hard cock, checking my watch to time it for a minute. She stared at me with her one eye and kept saying "thank you thank you thank you" over and over, "it feels so good, so good." She was clutching me any way she could but I held her to her word and pulled out 60 seconds later, giving her a couple extra thrusts and seconds for good measure. She asked what I wanted her to do, and I told her she already knew, so we switched places and she kneeled in front of me to take my cock in her mouth. Soon I was gripping her head to pull her down harder, she grimaced but stayed there while I started squirting into her mouth. She went "ugk!" but let me hold her down until I finished. She spat out onto some clothing on the floor and wiped her mouth, then after I wiped my cock clean asked her to suck some more, which she did for another five minutes or so.
I soon went home, and wondered if I was taking advantage of her desperation for sex to do something she didn't want. I called her later and apologized, though she said it was ok. I never saw her again but always wondered what became of her, and hoped she was one day able to get a glass eye to improve her appearance and have a better social life.
Her older friend greeted me at the door of her apartment, she also had a male visitor who I gathered was a truck driver. She seemed very protective of her young friend, but also wanted to give her space for her own, so soon she and I went into the spare bedroom to hang out. We soon did some kissing and necking, and I got her shirt off to suck her nipples. We agreed not to have intercourse on our first date, but I asked what she thought of oral sex, and she said she was fine with giving it but "I don't like it when guys come in my mouth." I admitted that this was my favorite activity, but would respect her limits. I instead stripped her naked on the edge of the bed and kneeled in front to go down on her, which made her moan in pleasure and appreciation. After she came once I kept licking and she she didn't push me away, clearly wanting more. But soon she started asking if I could go inside her. I asked if that didn't violate our earlier agreement, but she pleaded with me saying she wanted it so much now, and finally said "I'll do whatever you want if you just put it in for a minute." I again asked if she was sure and she said she was, so I stood up and quickly slid in my hard cock, checking my watch to time it for a minute. She stared at me with her one eye and kept saying "thank you thank you thank you" over and over, "it feels so good, so good." She was clutching me any way she could but I held her to her word and pulled out 60 seconds later, giving her a couple extra thrusts and seconds for good measure. She asked what I wanted her to do, and I told her she already knew, so we switched places and she kneeled in front of me to take my cock in her mouth. Soon I was gripping her head to pull her down harder, she grimaced but stayed there while I started squirting into her mouth. She went "ugk!" but let me hold her down until I finished. She spat out onto some clothing on the floor and wiped her mouth, then after I wiped my cock clean asked her to suck some more, which she did for another five minutes or so.
I soon went home, and wondered if I was taking advantage of her desperation for sex to do something she didn't want. I called her later and apologized, though she said it was ok. I never saw her again but always wondered what became of her, and hoped she was one day able to get a glass eye to improve her appearance and have a better social life.
- That's Juicy! 18
- Remove It! 7


