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Missed opportunity

Definitely this one time I regret as a missed opportunity when I was younger. I was at a friends house and while we were playing hide and seek I hid in his mothers closet where I found her lingere and dresses. As I was fumbling through them he found me. He asked what I was doing and I told him that I loved the feeling of the silky material. He mentioned that I could wear them if I liked, I laughed it off and we left to go play video games. Later on he asked me if I masturbated, I was shy, I had just started experimenting and looking at trans & gay porn so I told him idk. He was sitting on the bed behind me and I heard him rustle around, he apparently dropped his shorts and was humping a folded up pillow and asked me if I had tried doing that. I didn't look but told him no. He was really trying to engage my curiosity but I was oblivious. Then he flat out told me that he would give me one of his games if I would lick his cock. I was sitting on the flood leaning up against his bed and he was sitting on the edge next to me, I saw his cock from the corner of my eye. This was the first cock I had seen in person. It scared me and I freaked out, told him no and left.

I've always regretted this b/c I didn't know it then but thats what I wanted. I reacted poorly. I told the other kids at school and they bullied him badly along with me. He eventually transferred to a private school and then I never saw him again until about 4 years later. He was working at a local grocery store. He didn't see me but I wanted to walk up and tell him how sorry I was.
 
I just had one last night, because of my over-eagerness!!! A straight buddy of mine, while driving reached over and intertwined his pinkie with mine; he knows that I'm gay. I took it as a sign, when it was just him trying to be affectionate and not gay.
 
^ Didn't you get boned?
I wood have....... !oops!
 
A high school hottie came into the bar I was at, lol, totally drunk last month. We sat at the bar together, waxing nostalgia; he's married with child and knows that I am gay. Of course, I couldn't help but notice his raging boner shown in his near form-fitting shorts. Lol ... I did make mention of it, and he laughed, saying, "Yeah, it's always like that." IDK, if it was his marriage or our playing basketball & football together way back when that prevented me from making a move. Ha ha, I was waiting for his comment, "Yeah, I noticed that you timed all of your showers to coincide with mine," but it never came. My penis is nothing to sneeze at, but his is PERFECTION INCARNATE!

Talk about "MISSED OPPORTUNITIES!" Out of the blue, I got a FB message from him today that simply read, "you had your chance."

He lives mid-state, and I moved northern, but we still have family back at our high school area. Lol ... Thanksgiving and Christmas around the corner, but I don't want to be a barfly, and I certainly won't pressure him on FB. *sigh ... what to do, what to do?
 
Ask him if he'll give you another chance.......... :-<
You now know he's up for it.
 
Well, after a boatload of drama on his part, my married buddy (living with his new baby mama mistress) has been yearning for my expert blow jobs! Lol ... he even tried to tell his old lady that she has to swish her tongue under the head and shaft, and ha ha, she asked, "how would you know?"

Since I supposedly give the best head ever, he is willing to give up his fine, hairy ass ... lol, even admitting to experimenting with his girlfriend's dildo Wow, I knew that I loved cock, but to have a supposed "Straight" extol my fellatio skills to the point of giving up his ass ... WOW!!! This monumental moment has been almost 2 years in the making, so I'll probably be giving up my ass too. I want it to be special, and not just one-sided. Thankfully, he is just 5.5", lol, so when deep throating him, I do make gagging noises, because it turns him on ... ha ha, that just between us guys.

I would make a life with him, but he is too deep in the closet and denial. There isn't a day that goes by that he doesn't assert, "I am not gay." But just hanging out together, no flirting, he also asks, "Why the F*CK do you always make me hard?" To which I answer, "Because you're my bitch."
 
It is tentatively set for October 1st; he switched schedules with someone else, and I had to take the day off. We both have kids, so it has to be during the day. I so miss spending the entire night with him and his nakedness against me. WOW!!! I am beyond EXCITED!!!
 
funsicles said:
There isn't a day that goes by that he doesn't assert, "I am not gay." But just hanging out together, no flirting, he also asks, "Why the F*CK do you always make me hard?"
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That's always cute. I've had "straight" friends who've said things like that to me. I typically just giggle and respond, "Because I'm irresistible" and then do something coy like wink, blow a kiss, or grab/smack my own ass.
 
Okay, he missed asking me having calling me, which I did to wake him, wife there to get everything in order. I am supposed to watch the house, which I declined, because of my son and his cub scouts. My joey is beyond sexcited for exchanging blow jobs and probably more!!!

- - - Updated - - -

Lol ... so much for waiting until Tuesday!
 
Gregg is not coming up until Christmas, and sadly, he's bringing his wife, so hope is dim on that desire. Joey and I had to postpone our consummation a week, because his live-in baby mama mistress was in jail on a Failure to Appear warrant, and he didn't have a babysitter for their daughter and her 3 other kids. Joey valiantly tried twice to ride me, easing me in, but couldn't take it. We tried once more doggie style, and he still whined with little more than just the head penetrating. Alas, it wasn't a total loss, as the first time EVER in our 2 years of sexual play, he actually swallowed my load, which was MASSIVE!!! Lol ... I didn't masturbate for over a week.

We were just oral in our hotel room. I brought him to the brink a few times, but as soon as I tasted the hint of pre-cum, I quit. It was SUPPOSED to be our first, very special night with both of us fucking one another, lol, and he tried fervently to fuck me, regardless of his knowing our agreed upon him having to bottom first. Lol ... he was so mad that I didn't let him cum! He ended up just jacking off and sharing his seed on our bellies, as he fell asleep atop of me.

I did break down @ 5:42 am when I awoke and saw his morning wood. His perfect cock was not to be denied!!! I blew him to climax, swallowed my just reward, sucked him back to hard, wash, rinse, repeat! Lol ... his third load was just dry spurts. He did attempt to ride me again to no avail. Again it was off to the shower, and yes, he swallowed my load again. He wants to try again Thursday, and told me flat-out, no matter how much he bitches, lol, just shove it in, because he's going to have my ass right after. Ha ha.

Heck, the $95 hotel room rate was worth it, just to watch him walk about the room naked. For somebody that purports to hate kissing, he was all lips and tongue that night. Lol ... I'm not going to tell him, but Thursday will be my 6th stay at our local Best Western, so it's free. I've received exactly 11 nudes of him total yesterday and today. He wants my ass and to make me his bitch, lol, but acknowledges that he has to be my bitch first.
 
imariver said:
In my younger days, I was living with my girlfriend and on a couple of occasions, she mentioned that she had a co-worker that wanted to watch two guys having sex. Looking back and putting more pieces of the puzzle together, I'm positively sure that she was hinting about me and the co-worker's boyfriend. Fast forward a number of years and the opportunity to have "same sex" sex presented itself again and this time I took advantage of it and the rest is history. So . . . . now I often wonder how my life would have progressed, if I had taken advantage of that situation.
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Same kind of thing with my GF of 2 years. We worked at the same company. She told me her and a GF from work were eating each other out. I jokingly said’ I’d love to watch that.”. Days later she told me her friend was up for it if both of them could watch me suck dick. I had never actually sucked a dick before, had some experimentation in JR High but it never got around to that. My GF told me there was a gay guy at work who was willing to let me suck him but he wanted me to fuck him in the ass too. GF was excited and wanted me to go through with it.. She badgered me for days but I didn’t want to get involved with a guy from work thinking it would get all around work afterward. I always wonder how things would have turned out if I had gone along with it.
 
Many times. Here are a couple.

I spent the night at a friend's house one summer night in high school. It was really hot that night and the house didn't have air conditioning, so we were on top of the blankets in our underwear with the lights off. He was in his bed and I was on the floor. We were up late talking about how hard it was to sleep in the heat and my friend said he had an idea. He suggested the best way to cool off would be getting completely naked. I agreed and was quick to strip off my underwear. I was rock hard in a matter of seconds and couldn't wait to hear his next idea. I started to rub my hard cock while I waited in anticipation, but he never said anything. I really wanted to climb up in his bed with him to see where our nakedness took us. I didn't want to cross any unspoken boundaries, so I stayed on the floor and continued to rub myself. As I rubbed and thought about a naked guy being just a few feet away from me, I started to feel something that was very new to me. I rubbed faster and then it happened. My first cum load shot out on my chest and stomach. It was amazing. I laid there naked and played with my cum for a while until I finally fell asleep.
I woke up before he did the next morning and went straight home. My parents weren't home when I got there, so I knew what I had to do. I went directly to the bathroom and started to experiment with some stroke techniques. It didn't take long before I shot my second cum load. I've been hooked ever since.
As good as that night was, it would have been better if I had climbed into bed with my friend and shared each other's loads. That would have likely turned into a frequent thing.

A few years later, I worked with a gay guy who I was very attracted to. Something about him really turned me on. I would always feel myself getting aroused whenever he was near. He didn't need to say anything to get my blood flowing, but he was rarely quiet. He liked to talk about needing his cock sucked and how good he was at sucking cock. It took a lot of effort to not get fully hard at work when he talked like that. He would occasionally invite me to his place for drinks, but the sex talk and invites were never in the same conversation. It was pretty obvious what was going on though. As much as I wanted to go to his house so he could be the first cock to fuck my ass, I was afraid of people at work finding out about us. I had a "straight" reputation that I wanted to protect. If he had invited me over to fuck instead of just inviting me over, I don't think I would have been able to resist. I have no doubt that that would have turned into a regular thing, too.
 
I was a young phone technician dispatched to a older guy’s apartment in the city to fix a trouble. There was no question he was gay. There were gay magazines laying on the table and he’d follow me around while I was working. He talked about a theater in town where you could get a blowjob. He did just about everything he could with out asking me directly if he could blow me. I told him I had a girlfriend and he backed off. Probably best I didn’t go for it bc if he called the company on me I could have gotten fired. I could have used a blowjob though
 
boomer54 said:
I was a young phone technician dispatched to a older guy’s apartment in the city to fix a trouble. There was no question he was gay. There were gay magazines laying on the table and he’d follow me around while I was working. He talked about a theater in town where you could get a blowjob. He did just about everything he could with out asking me directly if he could blow me. I told him I had a girlfriend and he backed off. Probably best I didn’t go for it bc if he called the company on me I could have gotten fired. I could have used a blowjob though
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something similar happen to a friend of mine. He too work for a company were you go into peoples homes. He ran across a gay guy. My friend gives off big dick vibes. plus shows a print in certain pants( he' 9"). The guy went into another room from where he was working, When he came back he was butt naked and he ask/told my friend could he ride him. My friend said that he told him no. The guy looked disappointed when he said no.
 
boomer54 said:
I was a young phone technician dispatched to a older guy’s apartment in the city to fix a trouble. There was no question he was gay. There were gay magazines laying on the table and he’d follow me around while I was working. He talked about a theater in town where you could get a blowjob. He did just about everything he could with out asking me directly if he could blow me. I told him I had a girlfriend and he backed off. Probably best I didn’t go for it bc if he called the company on me I could have gotten fired. I could have used a blowjob though
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I've found every guy with a girlfriend could use a blowjob. Girls don't do it nearly often enough. I don't think any gay guy would blow you then report you though! He was more likely to say you could come back any time 😉
 
At that time I was just married and couldn’t risk losing my job but I agree about a gay guy inviting you back at anytime. When I was 20-21 my buddies and I went to a house party. The guy was older maybe in his 40’s. He was a church youth group mentor my one buddy knew when he attended youth group. I had worked 2 doubles and got there late. I dank too many beers and fell asleep in a back room. When I woke up everyone had left including my buddies. Our host had my pants down and was blowing me. I stayed over and blew me 3 more times. I couldn’t bring myself to return the favor because I still had a GF. He invited me back anytime. I went back after work a few times. My buddies never knew. I stopped after I got serious with a girl. As I look back I regret not returning the favor.
 
I had a hugely missed opportunity.
I cut my finger off while working, my wife drove me to the hospital.
The nurse was a guy (I was in a lot of pain but I noticed he was a good looking guy), he was hitting on me but I didn't realize until my wife pointed it out.
He asked me out for a drink or somewhere else of my liking, he said "you can bring her too" refering to my wife.

Again I was not clearly thinking.
My wife explained to me afterwards, he was (her words) "HOT" and would have loved for him to join us.
I went back to the hospital and asked someone I know that works there who he was but she couldn't find out.

I'd give a finger to be able to go back.
 
Way too many times, the few times that stuck to me

Many years ago, I think in 2011, this guy was a cute redhead guy. He would comment on my posts, and we chat here and there; he asked to hang out and grab lunch. I never responded to his message, and I bashed my head for not hanging out with him.

A guy I was crushing on in high school many years later he made a Facebook and we reconnected, and somehow the conversation went to sexual stuff and he wanted me to come over and do stuff, and I turned him down (I forgot the reason) and we talk here and there, but he ended up moving an hour away, and we rarely talk. its always a random message, a dick picture, and he goes his Mary way.

I was friends with this guy, and I always randomly touched him, and he didn't really care. One day we were at the bar, and he was going to hook up with a girl he was texting, and it didn't work out, and he was upset. When we left the bar, he was rock hard, and he was just smoking a cigarette and had a bulge in his pants. I kind of wish I made a move to see what would happen, but I never did.
 
I came late to getting fucked. Now my current obsession. All I can think about. Years of doing everything with my men and never getting a cock and cum in my pussy. That I regret, especially since so many were willing, had cocks that would have stretched and ruined and destroyed me. Yeah, that I regret. I have to respectfully disagree with MoaningMike who wrote, "If it was meant to happen it would have, so there must be a reason why it didn't." I am not a fatalist. Nothing is either meant to happen or not happen. The opportunities were there for me getting many cocks in my pussy. And I didn't do it. For whatever reason. Fate had nothing to do with it.
 
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