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Old 03-05-2012, 12:15 AM   #1
DallasMan1970
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What is your biggest sexual regret, and why?

Your regret can be due to any number of things - you wished you hadn't, you wished you'd done more, you wish you'd done something you told yourself you always wanted to do it but, when the time came, you just couldn't bring yourself to do it - the entire gamut.

I'll start, and I'm not certain this is my biggest regret, but it ranks pretty high on the list. If I can think of others I will let you know. This biggest regret is actually a two-fer: I once met a man online; he was bisexual, and I had no experience in that area beyond some basic curiousities. and we spoke of doing 3 ways with us and his wife. I'd seen a few porn shoots with some minor bi male material but not much and not for long. He and I spoke of the 2 of us getting together with his wife and doing a 3 way. I met the husband of the couple first, alone. Nothing serious, just a couple of drinks and some loaded language to thin the ice, establish a rapport, and see if we got along okay. All in all it went well. It was over and we both went our separate ways.

A couple of nights later we were chatting online. His wife was out of town and he was horny, browsing porn on the internet. I'd been browsing porn for an hour or so and I was equally horny.Eventually, over the course of our chat it got to the point of it being either time to hang up and take care of ourselves or see how far we were willing to go. It would be only me and him; he asked if i was interested in getting together, that night. I had to make a decision: do what I'd always done and wonder "what if", or say "fuck it", take a leap of faith. His letters on the screen appeared as he typed, and as I looked up they said, "Do you want to?" I hesitated for just a moment, started thinking, wondering if I had the guts to follow through. My fingers slowly fell into place on the keyboard and, consciously or otherwise, I replied back, "I want."

He lived about 30 miles away and was on his way. He was going to rent a hotel room just off the highway, about 3 miles from my apartment. If I got there soon enough I could watch him enter the parking lot. If I decided not to do go through with it I could always tell him in the parking lot, before he got the room, and end it before it started. He actually spotted me in the parking lot and waved me up. So much for ending this ridiculousness in the parking lot.

Fine. I went into the hotel and found his floor. He let me in; he had been there about 10 minutes. Had I waited that long before leaving my apartment? He offered me a beer, and I gladly accepted. He was sitting on the bed wearing only a pair of jeans, and he invited me to sit on the bed next to him and get comfortable. I noticed there was a porn film on tv when i walked around the bed. I don't know what they were doing, i am only certain it was porn.

I was in a highly charged situation - I had never done anything like this before in my life! - I was only interested in 3 ways where a woman is not just present, but a hearty participant. I had never been in an erotic situation knowing that there would be no female that night. And yet here I was, stretched out on a hotel room bed with another man, sitting up with my back against the headboard and my legs stretched out in front of me, drinking beer and watching porn together, knowing that we both came here planning for more.

Slowly he reached over and started rubbing my cock through my jeans. It was already semi-hard and didn't take very long for it to become fully engorged. He rubbed my dick through my pants with one hand and took his own pants off with his other hand. Then, when he had gotten his pants and underwear off, he focused on me. He unbuttoned my jeans, inched the zipper down, grabbed the waistband and began pulling them over my hips. Apprehensive at first, I lifted my hips off the bed and let him pull my jeans off. My boxers got stuck in the jeans and they came off as a bonus. I was now laying there totally naked from the waist down with another man, and my dick was hard as a rock. Alien territory for sure.

He reached over and stroked me with his warm hand, then leaned over and drew me into his mouth. At first it was odd, nearly off-putting, but it quickly changed to amazing! By this point my cock was throbbing, and he sucked it with long, wet strokes of his mouth and jerked himself off simultaneously. He sucked harder, drawing my orgasm further along, causing me to moan while the pace of him jacking off increased noticeably. I could hear him moaning in short gasps as he sucked my dick for all he was worth, causing me to quickly approach the point of no return. I felt him wrap his lips around the head of my cock, suck hard, and massage the underside of it with his tongue. At that point I couldn't hold back any longer. My body was wracked with an orgasm, and I could feel my seed spilling out the end of my cock. I opened my eyes and saw that his lips and chin were covered with my cum, and his hand and the area under his dick were covered in his cum.

It was incredible, but I felt a little awkward afterwards. Our conversation for the short amount of time we remained together that night was a bit stilted and i needed to go home to absorb what I'd done. With that, I made up a reason to go home. I felt tired, excited, calm, pleased, and post-orgasmic. I also felt a little weird...maybe guilty, but i don't think so. Not quite. I think it was more stunned that I hadn't backed down, I finally went through with it.

You may be asking yourself, what does this have to regrets? Well, I was just about to get to that. You see, I regret that I wasn't more bold. I regret that I didn't have the nerve to reach over and stroke his dick while he sucked mine. I also regret not having taken his dick, put it in my mouth, and sucked on his cock with the level of passion I felt. I regret not feeling his warm flesh harden in my mouth, tasting pre-cum seeping from the head, and feeling it surge in my mouth as he gets ready to cum.

I regret that I did not seize the opportunity when it presented itself.

We never got together after that, and I wonder if there even was an attractive wife who traveled a lot, or if that was just his shtick to get naive, bi-curious men to join him for a night of pleasure.
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Old 03-05-2012, 04:55 AM   #2
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Je ne regrette rien.
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Old 03-05-2012, 06:28 AM   #3
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That I was circumcised as an infant.

Based upon what I now feel, having mostly restored my foreskin, I missed some mind blowing sex. I will always regret missing what I could have had, taken from me when I was helpless.
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Old 03-05-2012, 08:40 AM   #4
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I actually regret being too shy and afraid of rejection as a young man. I think I lost out on a lot of sexual experiences in my teens and early in college because I was too afraid to let my desires be known for fear of ridicule or rejection. It took me a lot of years to understand that a lot of girls/women (at least back then) were themselves afraid to speak up and be open about their needs, so we just lost out all around. Like they always said, youth is wasted on the young.

The fact is, like is also often said, as much emotional pain, anguish, and upheaval as some of my actions caused later in life, I don't regret anything I ever did, only what I didn't do. Unfortunately, at this point, it's pretty much too late now.

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Old 03-05-2012, 10:24 AM   #5
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Excellent post, pretty hot and I like your perspective, I bet by the end of the thread it will the majority regret (that of omission rather than comission).
I let my girlfriend persuade me to put it in and I guess you can figure the rest of the story. She ended up being the first Mrs.. Back then they forced hormone enraged teenagers to marry. But you know its takes everything it took to get us where we are and I'm pretty happy now so it is what it is.

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Old 03-05-2012, 11:13 AM   #6
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Mbsr . . .

Would have to be not having more sex.
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Old 03-05-2012, 11:15 AM   #7
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Quote:
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Would have to be not having more sex.
My sentiments exactly
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Old 03-05-2012, 11:35 AM   #8
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The incident comprising my biggest regret occurred when I was in high school. I was staying at a friend's house, and his parents weren't home. He got called into work at the last minute, so I was left with his older sister. She was hot, had a (well-deserved) reputation for being on the wild side, and loved to party. We sat and listened to heavy metal, smoked weed and drank beers for a while, and then she leaned in and started kissing me--very aggressively. I kissed her back, felt her tits through her blouse, and then she started rubbing my crotch. She told me her boyfriend was in jail, but he would be out in another week.

Her next words still haunt me: "If you know what you want, now is the time. There will never be another chance like this."

I thought about it, and though about it, and thought about it. Then she got up and went to her room.

I stayed in my friend's room until he got home.

I wasn't inexperienced at the time, and I had no misplaced sense of loyalty to my friend. Rather, I was intimidated by the thought of the boyfriend getting out of jail. I had met him before, and he was a bad dude.

Two weeks later I was talking to another friend of mine. He stayed at the first friend's house the night after I was there. He stayed up drinking with the friend and her sister, until the friend passed out. They ended up fucking on the floor just feet from the passed out friend.

The boyfriend never found out.

And that's my story about the one that got away.
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Old 03-05-2012, 11:38 AM   #9
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that my friend dan failed out of college first semester junior year. we we're both dating pretty wild chicks at the time and had talked about getting a foursome together. I had my girl judy convinced to try it, and he said he'd work on his girl over christmas break, but he never came back to school. missed my best chance at a group sex situation.

also, I never bedded an asian or black chick.
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Old 03-05-2012, 12:55 PM   #10
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You know, there are a lot of things that I was about to say I wish I hadn't done, but then realized it's not the sex I regret - it's the stuff that happened afterward, none of which was a necessary consequence of the sex.

I can't think of any great opportunities that I missed, either. I mean, there were some good ones, but I took them, so no regrets.

Not bad, eh?
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Old 03-05-2012, 02:17 PM   #11
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its much easier for a girl/woman to act on their sexual appetites than a guy.
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Old 03-05-2012, 03:40 PM   #12
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Quote:
Originally Posted by peebudy View Post
its much easier for a girl/woman to act on their sexual appetites than a guy.
Well, I do what I can to remedy that, but I'm only one person.
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Old 03-05-2012, 03:43 PM   #13
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Well, I do what I can to remedy that, but I'm only one person.
and I'm sure your efforts are greatly appreciated!
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Old 03-05-2012, 03:58 PM   #14
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I regret choosing a university that was so far from home.

It was a highly competitive and presitgious university, and being 18 I was thrilled with the idea of being a thousand miles away from my folks and free to do as I pleased.

The downside was that I didn't get to sleep with my sister again for many years. Between timing and one or the other of us becoming involved in serious relationships with others, it was a long time before the stars aligned again for another encounter.

Had I sayed close to home, odds are we'd have continued unabated.
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Old 03-05-2012, 07:39 PM   #15
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I had a fairly kinky affair with a bitchy woman.

She gave me some heavy dildo love which was nice. We planned to take it to the point where she got me fucked for real, but guilt got the better of me (for having the affair, not for what we were doing) and I broke it off.

She used to say 'we are going to get you fucked' and she was deadly serious.

I still fantasize about how it would've been; me on my knees, shafted, her fully dressed, watching, smoking a cigarette, smiling.
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Old 03-05-2012, 08:17 PM   #16
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Old 03-05-2012, 08:51 PM   #17
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Regret

Not many things I regret. A few missed opportunities here and there.
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Old 03-05-2012, 09:18 PM   #18
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Where do I start..so many but here's two.

My best mate at the time. We were staying over at his sisters. He feel asleep in the room him & I were sleeping in & the sister & I ended up making out in that very room while he slept. She pulled my cock till I came, she went to her room & I regret that I didn't follow or even try to follow her to her room & return the favour & maybe fuck her.

A girl I once use to smooched with in highschhol once rang me years after & invited me over.
I asked why & she said "cause you havn't done me yet"
I went to her place , we were drinking & she was basically begged me to fuck her, practically raping me.
I just couldn't do it cause she was drunk & because I had dumped her in highschool.
I just felt It would be wrong of me.
I regret that I could of at least went down on her.
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Old 03-05-2012, 09:30 PM   #19
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Quote:
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its much easier for a girl/woman to act on their sexual appetites than a guy.
I'm a girl/woman......I haven't found it that easy....could be the damn zipper on this sheep suit
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Old 03-05-2012, 09:35 PM   #20
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I used to work with a woman who was drop dead gorgeous. She was 35...I was 25. So it never really occurred to me that I had a shot.

One day, after she moved to the other side of the country, she asked me why she and I never fucked. (And she said it that way, using the word 'fucked', which turned me on beyond all recognition)

I was like "we had that option?"

And she was like "Yeah, I'd have jumped your bones in a second. Why didn't we ever do it?"

Because I'm 6 degrees of stupid. That's why.
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Old 03-05-2012, 09:43 PM   #21
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Old 03-05-2012, 10:53 PM   #22
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I'm a girl/woman......I haven't found it that easy....could be the damn zipper on this sheep suit
lol!
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Old 03-06-2012, 01:22 AM   #23
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My g/f tried to get me to suck a cock for her for years before i finally gave in. My regret is that I waited as long as I did.
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Old 03-06-2012, 01:42 AM   #24
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one of my best girlfriends started to become very flirtatious with me. She was definitely going through a "curious" phase. I already knew that I was attracted to women and to this friend, but at the time (the mid-90s), it was still pretty taboo to be openly bisexual or gay. I was very timid and insecure about my sexuality and, even though I wanted her bad, I was afraid to act. It never even occurred to me that I could.

One night, she slept over at my house. She slept over all the time, but this time was different. We were lying on my bed and goofing off; and then, out of nowhere, she kissed me on the lips and said that we should be "real" girlfriends. I don't know what the hell was wrong with me. I got so nervous that I laughed it off, and she never said that to me again. Then, a few weeks later, she whispered to me in history class that another friend of ours, also a girl, had gone down on her and that they were now "together." I felt so disappointed and frustrated with myself. It could have been me...

Those two ended up being in a lesbian relationship for a long time, but my friend still occasionally flirted with me. I think she did it because she knew I liked it and couldn't do anything about it. She was a major tease. I remember hanging out with her one night, and her girlfriend wasn't around, and she started sucking and licking my fingers. It almost made me cum. And I will always regret that I didn't have more courage back then to just get what I wanted from her.

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Old 03-06-2012, 09:52 AM   #25
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Quote:
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I'm a girl/woman......I haven't found it that easy....could be the damn zipper on this sheep suit
Yeah. A quality sheep suit will have buttons, 'cause all that fuzz gets caught on zippers.
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