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Missed Opportunities

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Updated 7/07 [M 60s] Just thinking back to another missed opportunity I had back in my twenties. It was with a woman who worked where I was working back then. She was a couple of years older than I was an had been married before. She had kind of come on to me at work so one Friday I asked her out. She accepted and that evening we went to see a movie. We then stopped and had a couple of drinks and then I took her home. By now she was setting next to me and when we got in front of her house we started making out. She was the one that made the move. Before long, she had her hand on my penis in my pants rubbing on it and squeezing on it. I then slid my hand up her skirt feeling her legs and making my way up to her pussy. She spread her legs and I ran my fingers' along her pussy and then would feel her wonderful inner thighs. It had been awhile since I'd been with a woman and between what she was doing with her hand on my penis and what my hand was feeling under her skirt, I went off ejaculating in my pants. We then called it an evening. Then, that Sunday afternoon, she called me on the phone wanting me to come over to her house and see her. I certainly knew exactly what she wanted and from what I had felt that Friday night, she would had been one hell of a piece of ass. Yet, for some stupid reason, I made up some excuse and didn't go! To this day, I kick myself in the ass for not going that afternoon. Next time I asked her out, I guess she was so pissed at me that she would say "I have plans" and I never did get to feel the pleasures I know I could had felt between those soft thighs of hers if I had gone on over that Sunday afternoon. The opportunity was there and I flat missed it.

[M] It was 1992 when I was 18 and growing and very interested in women sexuality.My aunt(mothers sister) used to visit our home frequently and would sleep in the same room as mine .I would sleep on the bed and she would sleep on the floor. My aunt was then around 40 yrs,bra size 34 B and in great shape-slim,tall and very fuckable. Noone would imagine she was the mother of 3 children.When I would wake up the next morning with an erection my sight would just go to her crotch.I wished she was naked and i was fucking her then and there.Almost always I ejaculated thinking about that on my bed and then had to properly hold my penis walking to the bathroom so that the semen would not spill out. I think a few times my aunt saw this and pretended to be asleep.
In 1993 during my exams one fine day she came to our home and just left chocolates for me and went. In May 1993 my parents were to leave for USA so she came to help them to their trip The night they left,the next day morning I went off to play tennis early in the morning. I returned at around 11am,it was a sunday and we 2 were alone at home. After I came out from a shower,she came to me asking me if I wanted my legs massaged by her. Naive that I was then,I said no to which she enquired again.I politely said no and kept to myself .She then got lunch for me which I ate and went off to sleep. She was in the other room whole day alone.
I should have realised that the offer she was giving me of a leg massage was actually a sex offer as she too wanted to fuck me as badly as I wanted her. That day passed and its only now I realise it was a missed opportunity. My personal feeling is she was not sexually satisfied with her husband and when she saw me masturbate looking at her she thought it was a good opportunity. It was a missed opportunity for sure. We would have used contraceptives and had a great time.

Updated 6/07 [M] When I was a young fella, I was the R/O (sparks - radio operator) on a freighter sailing from U.S. to India. We carried twelve passengers amoung which was a very attractive young lady. As time went by we had a rip- roaring romance going. When the time came for an intimate sexual performance she was afraid of a resulting pregnancy unless we fucked with a rubber. But being under moonlit skies in the middle of the Atlantic I wasn't in the position to make a trip to the drug store and we had to settle for a hand job. So then whenever we left New York and thereafter, I had a good supply of rubbers with me. I guess that why condoms have been so important in my love life.

[M 45] In my early twenties, Jan cut my hair for several years. We also had mutual friends and traveled the same bar circuit, and grew to be fairly close. She was very pretty, but a touch wild for my (then) naive and hopelessly high standards.
As well as a full time job as a stylist, Jan worked part time at a restaurant. One night she introduced me to a coworker at both jobs. While Jan was pretty, I am comfortable saying that Mel was the most physically beautiful woman I have ever personally met. She had a dancer's body, and hopelessly blue eyes under impossibly black hair.Mel and I began to date, and on the nights she worked at the restaurant she would often call to talk about her day, frequently from Jan's apartment, and frequently after a couple of glasses of wine.
Mel was not shy, and would tell me about embarrassing moments during the day such as the time that, while dressing for work at the stylist, she forgot she had to do a shift at the restaurant. She had worn no underwear, and was acutely aware of that while serving customers at the restaurant. Her dark nipples and perfect breasts were apparent through her white blouse to anyone fortunate enough to notice.
Another time, with Jan giggling in the background, Mel told me about how together they had once seduced a coworker. Jan had tied him to the headboard and they had poured honey on him and licked it off. Jan had fed him hard candy from between her lips. I never asked which lips.
About a week later, I was at Mel's apartment. She had red light bulbs in all the lamps, and met me at the door in a T-shirt and panties. We immediately started making out on the living room floor.I was irritated when Jan called, and more so when Mel invited her over. I was also a little confused that Mel made no effort to dress or clean up. Jan showed up about ten minutes later, carrying a brown paper bag of hard candy. When Mel made no efforts to get rid of Jan, I left, frustrated and with a huge hard on.
Later in the week, I invited Mel out for coffee. She made great overtures about how Jan made absolutely the best coffee in the city. Again frustrated that Mel's friendship with Jan was getting in the way of my getting laid, we headed over to Jan's. Almost twenty years later, I still remember that the brown paper bag of hard candy from the previous week was on the coffee table. Again, when the girls showed no sign of breaking up the party, I left with a huge hard on dripping with frustration.
Mel and I broke up later in the summer. I'm not sure when it hit me exactly what I had overlooked, but let me quote my comments on the frequent occasions I remember this series of events... DOLT! IDIOT! WHAT WERE YOU THINKING! AAAGGH!...

Updated 5/07 [M] I was never circumcised and have slept in the nude for most of my married life. My wife's sister knows both of these facts and I know she has wondered what an uncut pensi looks like. She has mentioned that her husband is circumcised and quite well endowed. She has mention to my wife that she has done some research and notes that the average erect male penis is 5.5" long and 4" in circumference. I gather that her husband is about 9" long.
While on a trip to Atlantic City several years ago we stayed at the same casino as my sister-in-law and her husband, though on different floors. We had a great meal one Friday night and then gambled for a couple of hours before going to our separate rooms. My wife used the bathroom and then said she wanted to go back down and gamble some more. She said that the best time to win money was on a Friday and Saturday night. She said she would be back in a couple of hours.
I got ready for bed and turned on the TV and turned down the bed. I then removed my clothes but left my boxer shorts on while I went to the bathroom. There was a knock at the door and I thought it was my wife returning as she probably forgot something. I went to open the door but stood behind it as I was in my shorts.
When I opened the door I was surprised that it was my sister-in-law and she walked in without looking. She asked where her sister was? She looked in the bathroom and then noticed that the bed had been turned down. I told her that her sister was down in the casino and would not be back for a couple of hours.
She made a comment that she saw I was ready for bed and knowing I slept nude was expecting me to be naked when she turned to face me. I think she was disappointed and this is one time when I wish I had been nude. She could have had many of her questions answered as to what an uncut penis looks like. If I had been naked her comment would have been, "I see you have your PJ's on and are ready for bed."

Updated 4/07 [M 34] I was about 20 at that time (and was still a virgin), I was on my way home. It was about 8 or so in the evening and it was raining lightly. I was waiting for a cab when a woman came up to me. I was using an umbrella and the woman (who seemed to be about 18-20) asked if she could share the umbrella w/ me. I agreed and we both waited for a ride. The rain started to pour harder and it was becoming clear that it was going to be hard to get a ride. While we were together we started talking (I can't remember about what but whatever it was she was quite receptive). She mentioned that she was going to University and that she lived in a dorm or boarding house near her school. She had also mentioned that she had just attended a party and was a little tipsy. Eventually the we were able get a ride (not a cab but on a bus)
It really started to pour at that time. While riding we talked some more and I was really getting attracted to her. She was about 5'3" w/ shoulder length hair, slim, and had a pretty face. We were now talking about how to get home in the pouring rain. She initially suggested that we get off at a certain location where we thought it would be easier to get a cab and we'd go our separate ways. When we finally got down the rain was so hard and the street was flooded w/ ankle deep water. I half carried her to the sidewalk and awaited a cab. By then I near my home (I was still in College then, and was living w/ my mom and brother). I actually could walk home at that point. Still I waited with her until finally a cab arrived. At that point because of the rain she said that I should go with her. I hesitated and told her I was very near my house.
She repeated that I should go with her but for some reason I said that I'd rather go home. I guess I chickened out at the end. She then got on the cab and went home. At that point I did not think much about it. I was happy that a girl seemed to be attracted to me. But as time passed I realized what may have developed, or even what may have happened if I had gone with her. When I look back on that night I keep mentally kicking myself for NOT doing anything. By the way, to top off my errors for that night I was not able to ask for her number!

Updated 2/07 [M 65] Missed opportunities abounded during my very naive youth. To say I knew nothing when I first dated would be overestimating my sexual knowledge.
The first girl I dated during high school had parents who would let her out of the house, so we spent Sunday afternoons in her living room, watching TV and talking. One Sunday, when her parents were away, she snuggled up to me. I could see down her partially unbutton blouse and became somewhat excited. But my innocence wouldn’t allow me to do anything and I didn’t even understand why she acted disappointed when I was leaving shortly after her parents returned home. She broke up with me shortly after that.
A couple months later, when taking a girl to the outdoor on a Friday night, she snuggled and we kissed, and she groped and I did nothing. When I took her home, she said she really didn’t want to see me anymore. When I asked why, she said I was so naive that I didn’t even know what a girl expected. Somewhat bashfully, I admitted she was right ... I did not know what a girl expected. She was amazed ... we were both 19, she was experienced and I was still a virgin, even to touching ... and admitted it.
I then probably said the smartest thing I’ve ever said to a girl, "What am I supposed to do?" She then realized how innocent I really was and said I should pick her up about 11 the next day for a picnic in the woods.
She packed a lunch and we found a secluded area in a woods near town, spread a blanket and she suggested getting a suntan. I took off my shirt and she removed both her blouse and bra, much to my amazement. She then took off her slacks and panties and "strongly recommended" I do the same. There we were, in the middle of nowhere, naked, and I still didn’t know what to do. She told me to lay down (not on your stomach, stupid), and straddled me, sitting just behind my hardened manhood. She took my hands and placed them on her breasts and the rest just began to happen naturally as I felt the freedom to do anything I wanted.
I massaged her breasts, then moved my hands down her body, rubbing her legs and between her legs. She then laid along side me, stroking me until I was just about to come. She then got back on top of me, guiding me right into her and she began moving up and down. I just exploded. She laughed. "Now that’s what a girl wants," she said. "You think you can remember that."
We then proceeded to have our picnic lunch in the nude and made love one more time before going home. Life was completely different after that day.
We went our separate ways a couple months later, but every time I dated someone after that, little touches and caresses turned into wonderful experiences which continued to make life very interesting.
One girl I dated loved to romp nude in her apartment ... not necessarily seeking to make love, but just to enjoy the freedom. I did the same. Another loved to skinny dip in a river which ran through her folks farm (I found out later her whole family would go skinny dipping together occasionally).Few girls continued the projection of modesty they displayed in public once we got where there was more privacy. No every encounter was sexual, but they were all satisfying, thanks to my wonderful instructor

[M] Worked with a girl at a bar in the Rockies one summer. We used to run off and have sex in the basement just feet away from the customers, hidden only by a thin curtain, while on shift. The bar had a hot tub at its hotel. One Sunday night she came in with another waitress, and started doing shooters. They asked if they could go in the hot tub, so I closed up and joined them. When I got there they were both topless. One kept saying that if they were topless, I should go bottomless. She also kept saying we should play Truth of Dare. The sexual inuendoes were flying. I was seeing someone else at the time, so I held back and didn't bite. It was clear they were up for a threesome. To this day I ask myself WHAT was I thinking?

Updated 1/07 [M 40s] I am happily married, but while single I missed two opportunities that I still think about. The first was an incident that I previously wrote you about. One day when I was about twenty-five, I was sunbathing on a nude beach and saw this really stunning guy. He had long blond hair, was very well muscled, and was tanned all over. Neither excessively masculine nor effeminate, he was extremely handsome. More striking, however, was that his body below the shoulders was completely shaved including his cock. I had never before (or since) been turned on by a man, but that hot hunk with his sexy shaved cock, really got me going. At the time, I had already discovered dildos and wanted nothing more than to ride his cock. I have no idea if he was gay or straight or if he would have wanted to fuck me had I offered. Unfortunately, I chickened out at trying to make a pass at him, so I can only fantasize about what might have been.
The second missed opportunity was a few years later with a female friend of mine. We were having a conversation about sex fantasies and she asked about anal. When I told her that I did have anal fantasies, she seemed taken aback and went on about how anal sex would have to be so uncomfortable and what not, that I changed subjects. I have often wondered what she would have said if I had told her that my anal fantasy was to have her strap on a large dildo and do me in the ass. I have often suspected that she would have enjoyed the role reversal, but like the incident at the beach, I can only fantasize about what might have been.

[M] One very special "what if" I have occurred too many years ago in what was formally Rhodesia. We had as friends and neighbours a lovely couple "John and Maureen". He was in to home brewing of beers and wines and she had the most gorgeous lovely long legs and wore short skirts. Her skirts although short, were just long enough to keep the imagination wondering how far the legs went and did she wear knickers. We often visited each other playing cards and tasting the current home brew.
One special evening the wine had been flowing, John was more than usual eying my wife's breasts, as Maureen's were rather small (not that it mattered as she was a lovely girl). We knew about John's thing about my wife's breasts, and my wife sometimes teased him by wearing revealing tops. The conversation was full of innuendos. I needed to make a trip to the bathroom and on returning it was obvious that the three of them had been discussing something and then they sprung it on me "fancy swapping". It took me off-guard and before I knew it I was giving a negative reply. I could have kicked myself not going to get the chance to explore those legs. When we got home my wife asked how come; she thought that I would jump at the chance.
We decided that maybe it was for the best as we were (and still are) happy together and it could have gone very wrong.
So the long-term memory still works! Not that I could forget those legs and they play part of my fantasy most mornings when I wake up with other throbbing needs to be attended to.

Updated 12/06 [M 63] Thinking back when I was 20/21 years old and what I missed out on due to my inexperience or stupidity or what ever and I ended up a 22 year old virgin as a result. I was going with a girl that got me started in an older youth group at her church. That Summer we went our separate ways and she ended up going to school out of town. In the group was this beautiful blond with a body to die for. I didn't think I'd have much of a chance with her. One Sunday night I found out just how wrong I was concerning her. As it turned out she ended up hitting up on me!
On our first date we had dinner and then went to a drive in movie. Soon after getting there and setting up she and I came together deeply kissing. She ended up all over me in the front seat of my car. Here I had made it to "first base" but didn't know how to proceed to second. It was a case of "if only I had known". I sat there kissing and otherwise being the perfect gentleman although in my pants I had one hell of a full blown erection. I would had given anything at the time to get my hands under her dress and between her soft thighs for a good feel. I was so overwhelmed by women's legs that this was all that was on my mind and I figured things wouldn't go over very well if I had shoved a hand up under her dress all of a sudden.
I know now but didn't back then that the "key" was her breast! If only I had allowed my hands to start caressing on her tits things would had certainly progressed to "second base" and I'm sure the next thing I would had felt was her hand on that big boy in my pants. I well know exactly what would had happened after this. I would had finally had a hand under her dress feeling up her soft inner thighs and about that time I would had filled my pants with one hell of a load of semen. This was exactly what happened when I did finally get this far with a woman when I was over 22 1/2 years old! To make things worse this particular girl would had graced the cover of Playboy magazine. She had that kind of body and to think I could had lost my virginity inside her. This has haunted me all these years. What could had been!

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