While this is a totally true story, it is one I hesitate to tell because it makes me look pretty clueless. As sexually aggressive as I picture myself, this is one time that aggressiveness eluded me.
After my second divorce I started dating a woman (also divorced) who had an 18 y.o. daughter who was literally one of the best looking girls I have ever seen. This girl could easily have qualified as a center spread and I am not exaggerating. I spent a lot of time at the mom’s apartment complex that had a nice pool on site and so I got to see the daughter in a skimpy bikini as well as walking around the apartment in her thong underwear and minimal bra.
The daughter knew what she had and didn’t mind showing it off. As beautiful as she was, she was kind of a bitchy teen. Although she and her mom were close in some respects, there also seemed to be an undercurrent of competition between them. I knew that the mom was extremely proud of her daughter’s looks and it always surprised me that she let her parade around the apartment in next to nothing when I was there. I wasn’t about to complain. My biggest problem was checking out the daughter without being too obvious about it.
I frequently stayed overnight at the apartment, particularly on weekends. One Friday night I stayed over but the mom had to get up early on Saturday to meet with a client. I sort of slept in after she got up and left. I knew the daughter was a notorious late riser but really hadn’t given it much thought.
Annette, the mom, and I had a torrid sexual relationship going on. We really hit it off in the sack as well as any other place where she could get her hands on my penis and I could get my fingers in her vagina. We really went at it like two wild animals. As a result, I seemed to be in a constant state of arousal. When I finally got up that Saturday morning, with a nice case of morning wood, I jumped in the shower and maintained the erection. After towelling off I stood in front of the mirror and admired my still erect and very, very hard cock.
I stepped up to the counter, totally nude, and began to lather up my face preparing to shave. Again staring at my erect penis, which was bobbing up and down but mostly pointing straight up. I knew I was going to have to beat off before I could get dressed.
The bedroom door was closed but the bathroom door, which was off to the side of the bedroom, was open. As I stood in front of the mirror preparing the shave, Ariel, the daughter, walked in on me looking fresh out of the shower. She was wearing a robe that was tied at the waist loosely but sort of sagged open at the top and both of her terrific breasts were mostly visible. I could see the swell of both breasts and just a hint of areola showing.
While her sudden appearance shocked the hell out of me, she seemed to take seeing a nude man with a raging hard-on quite in her stride. She mumbled something about needing to get some make-up out of the medicine cabinet as she stepped up right next to me and opened the cabinet and rummaged around looking for something.
I stood there totally freaked out not knowing what to do and not even making any attempt to cover myself probably because she was acting so cool about it. I saw her look down at my prick and sort of stop what she was doing and focus on staring at it.
“Wow,” she said, “that looks really hard. Have you been playing with it?”
When I think back about this experience, I must have been dumbstruck because I didn’t know what to do. I was afraid to make any kind of move on her because I was really scared that she would somehow let her mother know what happened. I had a feeling she would get off on humiliating her mother by letting her know that her boyfriend made a pass at her. My mind was racing with all these mixed up thoughts. Annette had told me that Ariel was sexually active. She never gave me any details but said she knew for sure that she was. So in the back of my mind knowing that she was no virgin I half suspected that a pass might be welcome just so she could one-up her mother.
But much to my everlasting regret, I was too afraid to make a move. At the very least I should have asked her if she would like to touch it. But all I did was mumble some response that I hadn’t been playing with it, it just got hard like that every morning.
She said “My mom is a lucky woman to have something like that to play with” and then walked out of the bathroom. I was tempted to go after her but didn’t.
To make matters worse, I broke up with Annette a few weeks later. As good as the sex was, she was pushing me very hard to get married and although we were great partners in bed, there were just too many areas where we didn’t see eye to eye to ever get married.
If I had known at the time that Ariel caught me naked that Annette and I would be breaking up anyway, I probably would have made some attempt to get something going. I know if I had gotten her in bed, it would have been sex with the most beautiful girl of my life. I frequently fantasize of her kneeling between my legs and masturbating my steel hard cock until I spurt gobs and gobs of cum all over both of us. Or smelling that teen pussy as I tease it with my fingers and rub her clit until she screams for mercy.
I now look back years later thinking with great regret what I might have missed out on. I try to temper those thoughts by telling myself she probably would have been a lousy lay. Yeah, right......