Sex That Never Happened

Here are a few hookups that never resulted in any actual fucking. We’ve all had these. I’ve had way too many unsuccessful connections that never achieved the ultimate goal. Many of them while in high school. But I made some major mistakes back then. I was so focused on fucking, that whenever I was unsuccessful, I had no fallback position such as a handjob or a blowjob. I’m not sure how many high school girls were giving blowjobs back in the early ‘50’s. I never posed the question so I will never know, at least as far as the girls I was with. I’m only listing a few of the most memorable…or should I say the most disappointing failures, because all the others aren’t even worth talking about.

I had a small company with about ten employees. One was a very attractive young girl. She was probably 20 or 21. I knew she was planning on getting married shortly. One day she came to my office and asked to speak privately. She told me that she suspected her fiancée was cheating on her and she wanted to know if I knew of a private detective she could hire. I told her I could look into it but that realistically it would be very expensive to hire somebody to watch the fiancée. The following day I suggested that after work we go to dinner together to talk about it some more. OK, I admit it. In reality I wanted to fuck her in the worst way. So, after a very pleasant dinner at a fairly upscale restaurant where we discussed her situation in depth, we went into the parking garage to my car. That’s when I made my first move with a nice, very intimate kiss. And she responded. We then proceeded to really get hot and heavy with kissing and hugging. I attempted to free her breast but wasn’t having much luck. She kept saying she couldn’t do that. I really wanted to go for her pussy, but she was wearing slacks. Then I attempted a move I had never done before or since. I slid my hand down the back of her slacks and panties right down the crack of her ass. I started rubbing her little butthole and although she lightly protested, I could tell it was turning her on. Then I pushed my hand further and managed to get my fingers in her pussy. I admit that my arm and wrist were killing me because her pants weren’t that loose. I fingered her now juicy cunt and continued to kiss her. My dick was as hard as a rock. But I knew nothing was going to happen in the parking lot, so I drove back to the office where her car was parked.

         I invited her to go into the office with me thinking that it would be a waste of time to even ask and she wouldn’t go, knowing what it would lead to. But she did go, and I figured for sure that she had decided to fuck me. I know both of us got really steamed up in the car and the ride back to the office was only five minutes, so we were both still horny as hell. We went into my private office and ended up on the floor. We started back up where we had left off and I slid her pants down to her knees where I now had full access to that juicy cunt. I went down on her which surprised the crap out of her. I doubt anyone had ever done that to her. I was lapping her clit and she was writhing around enjoying the crap out of it while squeezing my now exposed cock when we heard the front door of the office open. Oh crap!!! We both scrambled to get dressed but kept quiet as a mouse. About three of my employees had keys but I had no idea who it was. We heard them moving around outside. My office door was unlocked, and I was waiting any minute for the door to be opened. Whoever it was knew my car and the girl’s car were parked outside and they had to be wondering where we were. Then we heard the front door close.

         The mood was totally destroyed. All she wanted to do was get the hell out of there and I wasn’t far behind, figuring there’s always another day. Well, there never was. She was scheduled to leave her job in a week or so and that’s what she did. I tried to talk to her about it, but she said what we had done was a huge mistake and she felt terrible about it. So that was that. I never did find out who had stopped at the office. Thankfully nobody ever asked what the two of us were doing.

I met a part-time model through my business relationships and used her in some promo material I was doing for the company. She was a real looker. She had been a finalist in the Miss USA contest and was now a college student. Not only was she drop dead gorgeous, she was also very intelligent and a genuinely nice person. If I hadn’t been married, I would have made a serious play for her.

         I can’t remember the specifics now, but I made an arrangement for her to come to my high-rise apartment for some casual photos. My wife was in Europe visiting her parents. I had no serious expectations of making out with the model but figured just spending a few hours with her would make my day. We started out with me shooting a large number of photos of her and as time went on the photos got more and more intimate. Nothing really risqué but some nice cleavage shots and close up facials. At one point, her beauty just overwhelmed me, and I kissed her. I was surprised a bit that she kissed me back. That led to a really super-hot and heavy make-out session. Lots of tongue action and we both were getting steamed up. I was really surprised at how truly passionate things got between two people who barely knew each other.

         Then a really strange thing happened. This had never happened before or since. But her breath changed. It was subtle but I swear it had the faint fragrance of pussy. It really turned me on. I raised the question of sex…in a subtle manner. I didn’t just say, “Do you wanna fuck?” But the signals I got back were very positive. I knew she was going to fuck me.

         Then the damn phone rang. It was the apartment front desk advising me that her boyfriend had arrived to pick her up. I had no idea that’s how she got to my place. He was about an hour early from the time she told me that she had to leave. She told me later that he came early to beat the traffic.

         So that was the end of that. I knew she got caught up in the moment but probably wouldn’t do a repeat. Plus, my wife got back a few days later and I never even bothered trying to get the model gal to meet up with me again. She went on to marry the boyfriend and they’ve been together for 50 years. I managed to track her down about a year ago and we traded a few innocent emails. That’s how I found out she was still with the original boyfriend.

I had a long-time employee who was leaving because she and her husband were moving out of state for a new position he was taking. She was one of my favorites. We had a long running teasing relationship but with us both married and working together, we were ok with keeping it above board. On her last day with my company, I took her to a celebratory lunch. We both had a bit too much to drink, and on our way back to the office, I got a wild hair up my butt and pulled into a local park. We sat and talked for a bit, and I could tell she was receptive to my possible advances. So, I did. And things got very steamy. I was sucking on one of her titties while she stroked my exposed cock. We both really wanted to fuck but were afraid to go that far in a public park. I couldn’t go to my place because my wife was there. I thought about a motel but was worried about what the staff would think if we were gone that long. I should have asked her to blow me or jack me off but didn’t really think about it. Stupid me. Back to the office we went. And that was the last time I ever saw her.

Here is probably the craziest one. I had a girl who worked for my company. We had flirted off and on for at least a year. It was one of those relationships where I knew that if I pursued it, there would be a pay-off. Finally, one day she was in my office and complained about a sore neck. I gave her a neck massage. Then I couldn’t resist myself. Standing behind her I slid both hands up under her sweater and was shocked to feel two bare breasts. No bra. She didn’t need one. She turned her head and kissed me. But that was all that happened because anybody could have walked in my office at any time. I immediately detected that the time was right and so I asked her out to dinner. And she said yes.

         I was separated from my second wife at the time, but we were temporarily still living together until the house was sold. My wife was leaving to go back east to visit her best girlfriend in the next couple of days

         The girl and I went to dinner at the local TGI Friday’s. After we got back in the car, we started going at it hot and heavy. I was tempted to fuck her right there in the car and I knew she was willing. But figured I could wait a day or two until my wife was gone and have a proper sex blowout at my house on a big comfortable bed. I talked to her about coming to my place two days later and doing the naked hot tub thing as well as finishing what we had started in the parking lot. She was all for it. . If my wife had already been gone, I would have taken the willing little lady back to my house right then and fucked her brains out.

         I think I must have had a permanent hard-on for the next two days just thinking about getting her naked. On the day that she was due to meet me at my house later that day, I got a call from her. She said she couldn’t make it. She told me that she was moving in with Larry. I said, “Larry who?” When she told me, I really couldn’t believe it. Larry was one of my best friends. I had no idea he was even seeing her. He had never mentioned it. I never did tell him how close I came to fucking his new girlfriend. The relationship didn’t last long, but once she was free, I was locked up with a new flame.

Another one I will always regret involved a woman I was dating who had an 18-year old daughter who easily could have been a Playboy centerfold. I frequently stayed over at their house. One morning the mom had left for an early appointment with a client. I was in the bathroom, naked, brushing my teeth when the daughter came in. Wearing a loose robe that showed both her pubic patch and one fabulous tit. She said she had to look in the medicine cabinet for something. As she reached across me she looked down and said “Nice cock.” Obviously, I could have fucked her right then, but knowing how competitive she was with her mom, I  figured she would somehow rat me out.  If I had known then that I would be breaking up with the mother in a couple of weeks, I would have gone ahead and fucked the daughter, who I have to tell you had one of the best bodies on a woman I’ve ever seen. Of course, she was only 18 which helps explain the great body and firm natural tits. I have always regretted not fucking her when I had the chance.

There have been others that I regret. More than once I have passed up doing the actual deed and putting it off for a better set of circumstances, only to never get another chance. The moral of that story is “Strike while the iron is hot!” Or maybe that should be said “Strike while the dick is hard, and the pussy is wet.” The truth is there will likely never be a better time than right now.  

(These are all true experiences….unfortunately.)

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