If you could have a 'do over' from age 18...?

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I would have gotten naked with a lot more men.

I wish that I had not been so shallow. Twice there have been women in my life that loved me unconditionally. They failed to meet my "requirements" so I instead ended up with wives that were beautiful but cared only superficially for me.

Do Over

I most certainly would pursue my bi side. I would also not turn down all the older women that approached me. So many chances!

Lily_Wight said:

I would have had a lot more sex.

I had this stupid notion that sex was only about love. I missed out on a lot of physical fun with some very enthusiastic and fit teenage boys.

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This, a lot.

I clung monogamy and straight sex.


4 years at university wasted. I should have got naked, sampled the world

When I was 18 there was a restaurant owner that took an interest in me and my college career. He later took me out to a very, very nice dinner and as I was young and dense, it only just occurred to me in that moment that he was interested in me romantically. At the time I'd already had one gay experience but it was really just experimental. I opted to play obtuse and distanced myself from him. If I had it to do over again I'd let him have fun with the 18 year old me.

Zeen said:

When I was 18 there was a restaurant owner that took an interest in me and my college career. He later took me out to a very, very nice dinner and as I was young and dense, it only just occurred to me in that moment that he was interested in me romantically. At the time I'd already had one gay experience but it was really just experimental. I opted to play obtuse and distanced myself from him. If I had it to do over again I'd let him have fun with the 18 year old me.

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Yep, when you're young and inexperienced, it can be hard to read other people's intentions.

I've told this story here before, but when I was in my early 20's I became friends with a coworker, Jim. He had a girlfriend and I was single, but we both had high sex drives, and a couple times we went to a porn shop together to get (straight) videos and magazines.

He had half-seriously suggested that we jerk off together sometimes, and I kind of agreed--but we never pursued it, and a few months later he left the job and we fell out of touch. Looking back on it now, I think there were a whole bunch of hints:

- He made several references to the fact that he had a really big cock.

- He mentioned that his younger brother was gay, and it was no big deal.

- He told a story about watching a porn movie with a friend, and his friend had to take his cock out and jerk off--and then afterwards his friend thanked him for not giving him a hard time about it.

- The same friend was over one night I was there, and we got talking about porn. The friend said something about "don't ever rent all-male videos--it's just guys doing stuff to each other." My friend Jim nodded in agreement, but afterwards I was thinking "well, ONE of them must have suggested getting a gay video in the first place, and if it wasn't him it had to be Jim."

- Jim told me that he had a video of his girlfriend giving him a blowjob, and he wanted to show it to me.


Putting all of this together years later, I'm pretty sure Jim really wanted me to give him a blowjob, or at the very least he would have gone along with it. I would have gladly sucked him off--right there and then, and pretty much any time he wanted from then on.

But, if that's what he wanted, he couldn't come out and say it. And I think I was so inexperienced and cautious about revealing my gay desires at that age that I didn't respond to his hints with any hints of my own.

As both of us were only interested in women romantically, I think it would have been an ideal "casual sex" scenario. I think I might have missed out on a lot of great cocksucking with no strings attached. And if we were doing that regularly, he wouldn't have had much trouble talking me into an assfucking, either.

Then again, maybe he wasn't interested in that at all. Who knows.

.....

midwestdude said:

admit to my bi-curiousness, and seek out that dominant woman

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By the way, very nice profile pic!

Astroman72 said:

By the way, very nice profile pic!

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I'll second that.. really nice profile pic..

My Bicurious Past

I'm glad I finally started to fully pursue my feelings and curiosities.... I wish I had begun earlier in my life. This was my first experience:

When I was 19, I worked a summer in a factory. I was slim, very blond in the summer. I was probably 5-6, 28 waist, clean shaven face....cute boy. A guy I worked with was gay, about 45 or 46. He was tall, about 6-3, and pretty muscular, and quite good looking. He would talk to me about his experiences with other men all the time, and this night I went to his apartment, something I did quite a few times. I was quite amazed by his stories, and learned a lot about male gay life.

I was fascinated by him, maybe a little attracted, and would visit him a lot. He lived alone about 15 minutes away. We'd usually just talk and he'd touch my leg sometimes. One time he came out of the shower, and asked me if I wanted to see it. I was curious and I did want to....because I assumed he was bigger than me. I touched it and held it, but not for long, but I was still amazed how big he was. And kissing it or putting my mouth on it was out of the question! That was the first time I held someone else's in my hand. He never tried to kiss me, or even talked about kissing, which is quite unusual, in hindsight.

Another time I went there, he shyly confessed that he had wanted to see my body for a long time, and he asked me to undress for him. I was very flattered, and excited, and after thinking about it for a minute or two, I said I would. I remembered the excitement on his face as I undressed, his anticipation as I turned my back on him to take my underwear off, and how he looked me up and down, and the arousal I felt as I stood there completely nude in front of another man for the first time in my life. And, surprising to me, I was completely hard and aroused.

He came over to me, and he couldn't take his hands off me, stroking and caressing...telling me how shocked he was at how much bigger I was than he expected. It was so weird to feel another man's hand wrapped around my cock. I think he even kissed it a little..... but he was cautious and afraid to offend me and risk that I'd leave. He kept telling me that I had the most beautiful body, and asked me to lay on his huge king bed....face down so he could look at my ass. I've always had a small ass, and he liked it a lot.

He stopped caressing me briefly, and he started to undress too. I remember turning to watch him, and getting excited watching him undress, an excitement I feel with other guys I watch. I was waiting to see again how hard and big he was. He was much bigger and thicker than me.

I remember wondering how he'd feel if I tried to take it in my mouth. He was so obviously infatuated with me. But I couldn't. If I sucked him that would mean I was gay, and I knew I wasn't gay! I told myself that for years.

He was telling me about this guy he met, and showing me how he got on top of him just like he was doing to me. I wasn't sure whether I should stop him....I didn't know what to do. He was very hard and big, and I felt the head against me from behind, and I didn't fight him as he slowly spread my legs. He was cautious with his pressure, he told me that's how he did it with his other guy, and how he had slid it all the way in with him. But eventually he stopped and gave up, saying I was just too tight and it wouldn't go in. I didn't see any way it would fit, and I had no idea then that with a little patience, foreplay, and lubrication, it might have eventually gone in. (I'm sure I was clenched up very tight!)

I must have been curious, because I don't remember trying to stop him or give him any resistance. I do remember a pleasurable feeling as he pushed, but I was probably kind of relieved when he stopped. He didn't try to use any lube, or lick me, or make any effort to enter me more easily. I felt a little guilty that he was disappointed.

I don't remember seeing him too much after that. It was only a summer job, and I went back to school. But nothing went any further with him at all. I had a GF at the time, who I eventually married, and she knew about him, but I never told her about that night or my experiences with him.

What I always wondered was what if things worked out differently that night? What if he had relaxed me, got me drunk, lubed me up, and slid it into me? I probably would have let him. Would I have liked it? Maybe. Would I have seen him regularly for sex? Maybe, or other guys. I would have been very popular, as cute as I was! Would I have had sex with every guy who came onto me? I would think I would have been somewhat selective. (Those were the pre-HIV days....) Who knows which way my life would have gone? In my 20s, but more in my 30s, a lot of guys came onto me. I would only let them touch me, and some begged me for more. I was never oral on a guy until I moved to Florida, and that even required some gradual, slow, and cautious experimentation.

Probably 2 things.

I wouldn't have got married. Because I am not at an age that I recognize that I was always a girl at heart.

Second, I might have followed through with the sex change operation that I was researching as early as 16--

I would have stayed only with girls lol......

I would have opened myself up to dating a passable transsexual. I lived in NYC and could have had a lot more fun. Might have explored my bi tendencies too. I also would have tried to live alone so that I could have cross dressed more. I always wanted to just wear panties and lingerie at home. I would have gotten a studio apartment and stripped when I got home and put on great stuff.

Had the mind to just be bi and be open and upfront about it so I would have met a woman that was ok with that quality.

If the do-over started from the same points of ignorance as the first time, life would still be filled with pain. If I restarted with what I know now, I would be a much more kind, considerate, and busy lover.

But... I see myself as having made bookoo fuckups... that led me to a good place in life. If I restarted, I'd be off elsewhere, without the love, joy, beauty around me now.

If your life sucks now, go for the restart. Otherwise, enjoy!

Well put, Hypoxia.
I have nothing to add after reading that.

Well, I would run amok among the house of student musicians I lived with at age 21-22 for a start.
I missed so many chances.

I had a broken heart, I'd had a mad engagement to an older woman that said a lot of bad things to me.
Things you just wouldn't say to a young man whose cherry you'd taken. I do not forgive some of those things even now.

I could have been off to Sweden by now!

Zeen said:

When I was 18 there was a restaurant owner that took an interest in me and my college career. He later took me out to a very, very nice dinner and as I was young and dense, it only just occurred to me in that moment that he was interested in me romantically. At the time I'd already had one gay experience but it was really just experimental. I opted to play obtuse and distanced myself from him. If I had it to do over again I'd let him have fun with the 18 year old me.

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Same here. Looking back I realize men wanted me in a sexual way. I had no idea. If I could go back....play it up, flirt like crazy and give them a thrill

do over

Hitchiker69 said:

If you could have a 'do over'...starting your sex life all over again from age 18...what would you do differently?

I would have a lot more gay sex. I passed up so many opportunities in years past, so many propositions passed up. For example I had a bisexual roomate who hit on me, and would have given me a blowjob almost any night of the week. I never did take advantage of that.

I lived in gay towns and cities where it would not have been considered out of the ordinary for me to have guys over for a night.

At one point my girlfriend had a gay roommate, and several younger gay friends who were available.

So I definitely would suck a lot more cock, and do every type of sex with men.

What about you?

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No doubt,

I would have come out of the closet (believe my parents had thoughts about me being gay) but got married, made 3 kids.. divorced.... doing it more and more

If I knew then what I know now, I'd be much more of a slut...

And I'd have bought Microsoft and Apple stock when it was cheap

I knew quite a few sluts who were attracted to me or dated me but were worried that I was too nice and would get hurt since they had no intention of being monogamous. I would tell them to go ahead and fuck whomever they want and let me share.

I would also have sucked at least one of the several cocks that were offered to me.

It’s probably a good thing. I didn’t know about the myriad of cocksuckers and trannies that would have been more than happy to suck loads out of my virgin 18 year old cock. I probably wouldn’t have gotten through college.

I would have taken the natural road to where my instincts wanted me to go. Hormones and medical help and become the girl I should have been.