So about 5 months ago, I met a 61 year old cougar on a dating app. I am (or was) a 27 year old black male virgin. See post history for details. She invited me over for a blowjob 2 times and told me the next time she would take my virginity. Well I kind of got cold feet and haven’t contacted her for months, until this week. I messaged her and ask if we can see each other again. Lo and behold, she is totally DTF, and wants to be my teacher.
Her apartment door is always slightly open, as an invitation to come in. Night lights still on as it was very early in the morning. I knocked and entered. I was greeted by Lin. This is a classy white mature snow blonde lady. She was wearing a night robe with see through underwear underneath. I was still kind of nervous but from previous encounters I knew she would take care of me. I made some small talk about the weather, traffic and the holiday season while she led me to her bedroom. Now Lin has groomed me from previous meetings, I already knew the drill. As casual conversation continued, I went ahead and took off my shirt, pants and underwear. She also took off her night robe. Revealing her gorgeous blue underwear. I don’t know what it is called, but it can be described as see through kinky underwear with multiple designs that has an open slit between her legs showing her vagina. To be honest, seeing her in this underwear made my one eyebrow raise. Fck, she is hotter than I thought, seriously. Must have been a bombshell back in the day and still is. Father time is cruel but mother nature still endows her age with a “thick” hourglass probably more so pear shaped nowadays. I said, “Nice fashion sense.” With an awkward surprised but happy expression, she said “Thanks!”
I had no idea what was going to happen next. Although, I certainly didn’t have to worry about performance anxiety. She was staring intently at my erect penis. She motioned me to lay down on her bed. Placed a pillow behind my head to make sure I was comfortable. With no hesitation moved her thick body right over my whole body, my penis rubbing against her lower area. And started kissing me very passionately and looking into my eyes between wet kisses. Our bodies embraced. Also stroking my hair and repeating caressing me. I was so overwhelmed, is this really happening? LOL. I didn’t know where to put my hands, so I just squeezed and rubbed her thick butt.
After what felt like a lifetime of making out, she started kissing my nipples, my chest and slowly worked her way down to my penis. Her blowjob skills are amazing which I mentioned last post, so I won’t go into detail. After getting me riled up, she told me to go ahead and put on your condom. I opened the condom and stared at it with a puzzled look. Oh shet, I forgot to practice putting it on, I don’t even know if the size fits me! As if realizing my inexperience, she took the condom out of my hands, and put it on herself. She told me while smiling, “I’ll get on top first.” I was kind of shocked, didn’t even know what to day, its going to happen! I thought. She climbed on gently and placed my penis inside. I felt this weird pressure and its confusing how my penis even got inside. But overall, even with a condom it felt good. She slowly rocked back and forth, asking me if I felt good for a couple minutes. After that, Lin said, “Now you go on top.”
This time Lin laid down. Pulled her legs up with her own hands. A slightly hairy pink pussy was seen through the slit in the blue underwear. She guided my penis inside, as I still don’t know the anatomy of that thing. I started thrusting awkwardly, she told me to calm down and told me to do an in and out motion. Well, I soon got the hang of it with effective thrusts. My face close to hers, I kissed her passionately while thrusting. From all the previous activity, just a few minutes in even with a condom on, I felt I was gonna burst. I started grunting because dam surprisingly sex is exhausting quick. She thought I was cumming and grabbed both my butt cheeks and pulled me in. That surprised the hell out of me, this lady knows what she is doing. A few more seconds with deep hard thrusts in this position made me cum hard with her encouraging me on. “That’s it!” “Good!” I collapsed, not panting, but kissing her as my body felt weak.
Lin told me to lay back down, “I’ll clean you up.” Lin gave me another blowjob. She laid back on top of me, locked in her arms, she started kissing me again and we had some more small talk. She’s glad I decided to see her again and wants this to be an ongoing thing. Well, we will see as its quite a drive to her area but worth it!
And that is the story on how I finally lost my virginity at 27 years old. Definitely a memory I won’t forget!
Source: reddit.com/r/gonewildstories/comments/awnqsr/mf_awesome_time_with_cougar_part_2
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