Missed Opportunities

What are some sexual opportunities that you regret missing or passing up?

My biggest one is passing up the opportunity to be in a casual relationship with an experienced and very uninhibited older woman.

Now this is very stupid, I know, but here's what happened:

Back in highschool, I was quite a shy guy and I didn't date girls. And so, there was one time when two girls approached me (they were friends), and one who was less shy explained that her girlfriend liked me and wanted to get to know me and so on, while the girl in question was all edgy and nervous.
She was pretty.
But I suddenly got so nervous myself that I lied my way out of that situation, saying that no offense, but I didn't feel about her like that, even though she's a good person.


yeah... Yeah, that was one of the biggest screw-ups in my entire life.

Two instances for me:

Turned down an option for a threesome with a then-gf and her best friend. It was a last ditch effort by her to keep me from dumping her, but I wasn't ready to put up with her any longer. Her friend was a curvy redhead and had previously flirted with me...so it was a sure thing and I stupidly decided to be a nice guy and just dump her.

Second instance - also being a stupid nice guy. Took a my friend, a way-out-of-my-league gorgeous blond (literally model quality looks) to a formal function. She hit the champagne hard and lost her inhibitions and I actually had to carry her to her room and put her to bed, by herself, despite her protestations. We were and still are friends and I desperately wanted more, but never acted on it. Even when I had a second chance at her birthday party where the circumstances repeated themselves, I always remained the gentleman. Nice guys do always finish last.

My wife's missed opportunity - the one guy who she would have jumped in a heartbeat if she had got the change. Allegedly he was sexy and handsome and charming and completely irresistible, but she couldn't loose her friends at the time and couldn't arrange a second opportunity.

.......

I was (still am) friends with this girl back in college. Her and her boyfriend at the time just broke up and she asked me to stay the night in her dorm with her. So I drove 3 hours and arrived late at her dorm. I haven't had a girlfriend up to that point but seriously wanted something to happen between us. I think she wanted the same. But it ended up being awkward and we ended up watching a movie. She fell asleep her in bed and I was on the floor. Biggest regret I ever made.

A friend was in an abusive relationship. She came over one night and had a bit of a breakdown. After some tears and hugs she asked if I would massage her shoulders and neck. After a few minutes of that I offered her a proper masage. She accepted and soon she was topless face down on my bed all lubed up and moaning slightly.

I offered her a "full body" masage, which she accepted.

After having some near misses with her panties I suggested she just remove them and I massage her buttocks as well.

I was so hard!

With each stroke I parted her ass. She had a really beautiful asshole. I could clealy see her pussy, so pink and moist it was dripping.

I often think about that night. I valued the friendship over the sex and apoligezed for taking it that far. The memory still gets me hard today.

My wife

Ha! Don't remind of the years of potential missed opportunities.

Years ago my wife cheated on me with another man. I was furious and it almost ruined us. But we kept our relationship together and we moved on. Shortly after though I started to become aroused by her tryst and started fantasizing about other men screwing her. Fast forward to today and my wife and I are now in a semi open, hotwife type marriage. So now she seems to be making up for lost time. But I regret not telling my wife my feelings and desires back then. Other men could've been screwing her all these years!

Before meeting my wife, I kept bumping into a former school acquaintance on nights out. At school she was shy, tall and a bit geeky.

Anyway, in the 6-8 years since I'd seen her, she'd blossomed. Blonde, beautiful, curvy, stunning. We exchanged numbers, texted a lot, met up etc.

One. Ighr, wound up back at hers, and she was all over me. But she was borderline paraletic drunk. An absolute mess. So I got her settled on the sofa safely, and left. Not fancying a date-rape claim at a later date, or other awkward moments.


Turns out she was gagging for it, and still cripplingly shy. So had got drunk to overcome it. Then was suitably unimpressed that I'd turned her down, so cut contact.


Damn my strong moral compass.

I was a member of a Toastmasters club once. One time our club was holding a club anniversary and we were preparing the venue the day before the event.

One of the members there was a 35-40 year old housewife who I knew was a mother of two. Short hair with a curvy and thick body. Wearing a black tanktop and tight jeans that day.

I can't remember what the two of us were in charge of, but goddamn, she was rubbing her tits all over me everytime we brushed past one another and bending over in front of me. She was also asking me if I was taking anyone to the event and saying that I shouldn't go myself.

One of them comes to mind. I'm sure there were a few others, I just can't remember.

I missed a chance with an older married lady when I was 30 or late 20's. She was blonde nice figure with big tits. I completely missed the signals. I flirted with her the previous week and grabbed her ass to see her reaction. She didn't slap me. Just a surprised look on her face. Then she dropped by my house the next week to borrow something wearing a tight red sweater. I would have been all over her if I had realized it at the time she was coming on to me.


A friend came over and she made the comment about laying down before the drive home. She was gorgeous with enormous breasts. We ended up in my bed and she was fully dressed. She said she was hot and removed her top, bra, and pants. The room was completely dark. I did caress her big beautiful breasts some and she didn't say anything or stop me. So I pushed it farther, I tried to put my hands down her panties and she stopped me. We didn't talk or kiss. The next day she said she wanted to do more but was afraid because she had HPV(human papillomavirus). She didn't want to do anything with someone that didn't have HPV unless she was in a committed relationship with them. But she regretted not having me suck her tits while she masturbated for me. And then give me a blowjob. SHIT! We never hooked up again.

My girlfriend (future wife) and I had been dating since she was a freshman in high school, and I had promised her that I would never do anything to hurt her, including risk getting her pregnant. We planned to get married as soon as she graduated from college, and I promised her that we would not have sex until our wedding night. During her senior year in college, we were having our usual session of mutual masturbation on a date when she lay back, spread her legs, opened her pussy lips and said, "I want you inside me." I started to do it, but stopped. She never offered again until our wedding night. I regret missing that opportunity because she told me after we were married that she had been screwed by several other guys in college. She got horny between our dates since I only got to see her once or twice a month.

I've always been one for whom skin color has never been a consideration when it comes to a beautiful woman. My missed opportunity was when I was in my mid 30's.

I was dating a beautiful brunette off and on and we were considering getting serious and exclusive but hadn't really discussed it at this point. All the while, a co-worker's friend, a lean, beautiful woman of color was flirting and teasing me. At one point she even asked if I'd be interested in dating a black girl. Being a "good boy", I stayed true to the woman I was dating and declined her offer. Sad thing is that we only lasted 3 years before divorce proceedings started. I kept thinking back that I should have taken that offer.

My greatest regret of all time definitely occurred in college. I was a white boy who had been dating Maria Herrera, a girl from East Los Angeles who was as sweet as an angel and as gorgeous as a fashion model. She was also a good Catholic girl who wouldn’t even dream of having sex before marriage.

We had broken up about a month earlier. I was sitting in the student union munching an incredibly boring piece of pizza when Catalina Rodriguez walked up and sat down next to me on the couch. In those ancient days (1970s) girls from similar neighborhoods were assigned to the same dorm rooms – Cat was Maria’s roommate. She had long black hair, creamy unblemished olive skin, and enormous dark eyes. She was almost as gorgeous as Maria, but unlike my ex, Cat wasn’t exactly a “good girl.” She was a genuine low-rider chica from the barrio. She wore skimpy tops with lots of bra strap, and tiny denim skirts so short that you could see at least two glorious inches of white triangle whenever she was sitting down. Even when I was with Maria, I had dreamed about Cat.

She said, “I’m sorry you and Maria broke up. It’s always sad when lovers part. I broke up with Randy too.”

She put her hand on my knee and said, “I’ve always really liked you. I know Maria’s afraid to go all the way with guys…”

She moved her lips closer to my ear and said, “But I’m not.”

It just so happened that I had been suffering from a urethral infection for the last couple of weeks. It was the first time in my young life that my dick had ever been in pain. I didn’t know what to do. I gave her some excuse about needing to study for mid-terms right at the moment but promised that we would get together really soon.

She was really nice about my incomprehensible waffling, and we agreed to go out on a date. But a few weeks later, when my infection had cleared up, Cat Rodriguez had already found another guy.

......

mysticdreamer said:

Even when I was with Maria, I had dreamed about Cat. She put her hand on my knee and said, “I’ve always really liked you. I know Maria’s afraid to go all the way with guys…” She moved her lips closer to my ear and said, “But I’m not.”

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There's a ringing in your brain, cause you coulda swore you thought you heard her saying Good Girls Don't.

had a missed opportunity with a coworker a few years ago. a couple of weekends ago I fulfilled it,

I've had several missed opportunities. Mostly because I wasn't smart enough to figure out what was happening, but in one or two cases I passed.

My first missed opportunity was with my best friend's sister Sheryl. She was friendly, and in hindsight also flirty and dropping hints you could drive through. I was very clueless until a couple of years later when her brother passed away unexpectedly. She sent a very warm "you meant the world to my brother" card, but also wrote that she had always had a thing for me and wondered why I never took her up on her many offers. Everything clicked into place and I had a Doh! moment.

Number two was a gal that I went to school with. We hung out together a lot and were both computer nerds. When I graduated high school I dropped by her house to visit, when she turned on the "my parents will be gone tonight, come over and we'll really get to know each other" charm. I knew what she meant, but panicked and bolted because I had no idea what to do. It pretty much ended our friendship, which to this day I regret more than the fact that I didn't get into her pants. She was a great gal, and we probably would have made a great couple.

Lastly, when we were courting my wife offered me a threesome for a birthday present. She knew a gal who was game, and all I had to do was say the word. I really couldn't imagine getting into anyone else's panties (even in a threesome). That was when I realized that I had met "the one", turned down the threesome, and told her that if we were going to go the distance that I would rather only be with her. I don't regret the choice, or the fact that I married her, but occasionally it's fun jerk off fodder to think about it.

There were others in between. Girls flirting in college and other opportunities that I only realized after I got married and really started to learn about women.

I can think of a few, two of which I have mentioned here before. The first was a few days after high school graduation. I was drinking beer with a friend in his backyard. His older sister joined us. She was 21, attractive, with long black hair and a killer body. She always wore tight, hip hugger jeans and tight t-shirts. Her clothing left nothing to the imagination. I had known her since I was a freshman, but only talked to her a few times in that four year span. It was a hot day, and the beers were cold and after a while my buddy passed out. That's when she made her move. She moved over next to me, put her hand on my thigh, and whispered in my ear: "I want you and I know you want me too." I didn't say anything. We kissed for nearly five minutes. Then she said: "If we're going to do anything, we have to do it now. My boyfriend gets out of jail tomorrow." That was exactly what I did not need to hear. My boner disappeared, I stammered something stupid, and then I got up to leave. I never saw her again.

A few years later I missed another opportunity. My girlfriend and I were invited to dinner at a friend's house who we knew in high school. At the last minute my girlfriend had to cancel, so I went alone. I was surprised when I arrived and found that my friend's sister had moved in with her and was joining us dinner. The younger sister was gorgeous, but was dumb as a rock. I quickly became infatuated with her and all night I was trying to think of some way to be alone with her. We smoked some weed, and then the sister went to bed, leaving me with my friend. We smoked a little more. I knew it was time to leave, but I was stalling on the outside chance that little sister would come back out. She never did, and finally I got up to leave. That's when my friend took my hand and asked me: "Do you think I'm attractive?" The question floored me. I had never thought of her in a sexual way. She was kind of attractive, a little chubby, and had enormous tits. She was also one of the smartest girls in my high school class. She was fun and witty, but I just never thought of her sexually. I looked down at her and saw her staring up at me. The longing in her eyes was heartbreaking. I mumbled yes, of course. I gave her a quick kiss on the cheek and left.

The walk home was agonizing. So many emotions were swirling around inside me. We remained friends, but we never had another moment like that again.

A third missed opportunity happened two years later when I was a senior in college. A buddy and I met up late at our local rathskeller and proceeded to down a pitcher of fine German beer. It was nearly closing time and we finishing off the pitcher when the waitress set a new one down if front of us. "Compliments of the lady at the end of the bar," she said as she walked away. We looked down the bar and saw a 40 something year old barfly sipping a martini and filling an ashtray with cigarette butts. She smiled and then stumbled over toward us. She was plain-looking, neither attractive nor repulsive, but she looked like she spent seven nights a week drinking. We thanked her for the pitcher and made small talk with her, and then the bell rang for last call. She invited us both to her place for the night. My buddy and I looked at each other and started making excuses why we had to go home. She gave us a pained look, put out her cigarette, and left. We joked about the situation for days, but the truth is if I had been there alone, I know I would have gone home with her. I think my buddy would have also. But neither of us were up for a threesome, and neither of us wanted to admit that we would have gladly fucked her in a one on one situation. I didn't really regret that one until years later when I became interested in group situations. At that time, however, it was not an option I would have considered.

Finally, there was a situation a year later when I was in grad school. Some married friends invited me to go with them to a New Year's Eve party. At the last minute they told me they had also invited another woman who was also in some of our classes. I knew her, but not well. She was kind of aloof, and hippyish, always wearing peasant style clothing and no make up. She was attractive, but did not stand out in any way. Until that night. With a little effort, she looked stunning. Well, we got to know each other well that night, and our friends had assigned their guest room to us. Everything was set up for us to have a great evening together. Unfortunately, I drank too much at the party. I knew the evening was in jeopardy when I threw up in the kitchen sink. Nonetheless, I persisted. We went back to our friends' house and got ready for bed. We both took off our clothes and laid down together. I reached for her, and she turned her back to me. When morning came she left before I was even out of bed.

That one was a blown opportunity. She was ready and willing, but I fucked up the situation. I never got another chance with her again.

My Uncle, my Mom's Brother. He was a big guy and always see the outline of his cock thru his pants and it was huge. I would have loved to suck it or take it up my ass, but he passed away very young and I never got the chance.

Crazy doctor

Many years ago, we lived in a townhouse with a shared driveway. A hot doctor moved in. She would lay out in her bikini in the backyard that was visible from our bedroom window. She was a huge flirt to the point of telling my spouse she wanted to fuck me. She got a puppy but with her irregular hours, she gave us a key so we could check on him, let him out. Like a good perv, I'd snoop, find her used panties...sometimes she would leave her dildo out. She was going through a rough breakup and I'd helped her a good bit. I had some time off and one afternoon she asked if she could take me to lunch the next day. Sure. She suggested a high end restaurant that happened to be in a hotel. I didn't think anything of it but suggested a more casual place. We had a good lunch, a lot of flirting. Afterwards she asked me inside...she wanted my opinion on her new bikini. Sure! She goes into the bathroom to change and comes out totally nude! "Well, what do you think?" I said, "I think anybody who sees that won't complain about the tan lines and if they do, they don't deserve you. I need to be going."
I could've had her but she was as crazy as she was hot...and she would've bragged to my wife about it. Glad I didn't then...but not so sure I'd turn it down now.

NOBGE said:

Many years ago, we lived in a townhouse with a shared driveway. A hot doctor moved in. She would lay out in her bikini in the backyard that was visible from our bedroom window. She was a huge flirt to the point of telling my spouse she wanted to fuck me. She got a puppy but with her irregular hours, she gave us a key so we could check on him, let him out. Like a good perv, I'd snoop, find her used panties...sometimes she would leave her dildo out. She was going through a rough breakup and I'd helped her a good bit. I had some time off and one afternoon she asked if she could take me to lunch the next day. Sure. She suggested a high end restaurant that happened to be in a hotel. I didn't think anything of it but suggested a more casual place. We had a good lunch, a lot of flirting. Afterwards she asked me inside...she wanted my opinion on her new bikini. Sure! She goes into the bathroom to change and comes out totally nude! "Well, what do you think?" I said, "I think anybody who sees that won't complain about the tan lines and if they do, they don't deserve you. I need to be going."
I could've had her but she was as crazy as she was hot...and she would've bragged to my wife about it. Glad I didn't then...but not so sure I'd turn it down now.

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That is hot! Too bad you couldn't get your wife to have a threesome with her.

Ioh man. I missed it......