The time I could not perform

Back in the heyday of CL personals I was addicted. I would run the craziest ads with sometimes amazing results.. though sometimes you would get flakes, dudes, pay for play, and masturbators. I would be very very specific and concise(not doing that here unfortunately). I ran an ad that basically said I wanted a slim petite woman for rimming and anal sex. Most of the responses were garbage but one intrigued me. She described herself as a butch lesbian in a relationship with a runners build. Her gf shared with her one thing she missed about being with a guy. That happened to be getting fucked in the ass. She wanted to experience this for herself. I advertised that I was an expert, that it would only hurt a little. I was super excited. She shows up with literally the body of a little boy,, no more than 5 feet tall likely 95lbs. She was all business and just wanted to take her pants down around her ankles. I was not taken aback but her aggressiveness through me off. I was hardly close to being erect so I negotiated to be able to tongue her pussy a little and open her ass with my tongue. She was gushing but wouldn’t really let me eat her out. I spent a lot of time with my tongue in her ass and trying to get her to relax. By how wet her pussy was she enjoyed it. My cock was super duper Captain Kirk fucking the universe hard. Then she said just put it in me, it doesn’t matter if it hurts, dont stop and just fuck me. I lubed up(no condom), and tried. I didn’t even get the head in and she was screaming bloody murder, i pushed on and she was literally crying and begging me to stop. I pulled out slow and she reacted like I turned her inside out. After about a minute she asked me why I stopped… I had a WTF moment and said I thought I was hurting you so I stopped. She said I told you in the beginning don’t stop no matter what… I am not into forcing people or into causing pain and I could not get it up after that even though she tried very fucking hard. Flash forward 6 months after this failure I run into her and her gf in a local restaurant and all I could do was provide a sheepish grin.

3 months ago

3 Comments

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    • That's a load of shit! I fuck my gf with a strap on and so does every other lesbian out there. There are fake strapon dicks you can buy that feel better than the real thing and they are bigger and harder than you ever could be so stop fantasizing about lesbians because we don't need you.

    • Wow, its a true story. I don’t fantasize about lesbians, i just love women. No matter what you say sometimes its not just about some highly specialized strap on that supposedly feels as good or better than the real thing but the decadence of the real equipment from a real man.

    • You should have used an average size of dildo with lube to stretch her anus for about an inch then use your hard cock in - this should have been better.

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