Thank you to ‘Rants from the Erotic Rogue‘ for this week’s TMI Tuesday.
Looking back on our lives, we can have a mix of reactions to the things we’ve done. When it comes to sex, our memories can color us with pride, fondness, nostalgia, indifference, or all too often, regret.
This week’s TMI Tuesday questions delve into things that people typically regret later in life. How much do you regret, if at all, any of the following?
Jack’s Answers
1. Do you regret how you “lost” your virginity? If yes, why and to whom would you have preferred to have lost it?
Of course I regret the manner in which I “lost” my virginity. (Why is “lost” in quotes above?) I’m guessing that no teenager who first has sex with his sixty-year-old biology teacher in exchange for a passing grade is going to be particularly proud of it. On the other hand, I sure as hell didn’t want to repeat the tenth grade; at the very least there was no way I was going to willingly sit through this guy’s class for another year. So I guess that I did what I had to do to ensure that said repetition didn’t happen, and I have no business regretting it. On the other hand, it being 1992, I would much rather have lost my virginity simultaneously to Cindy Crawford, Heather Locklear, Pamela Anderson, and whoever in hell Kim Basinger played in Cool World.
Yeah, her.
2. Have you ever lived a moment in your life where you said “Yeah, I’m not going to ever tell anyone about that.” Describe that moment or incident.
See above.
3. Do you regret having acted on a sexual impulse? If yes, please describe.
I don’t believe that I have. Unlike Jill, I can’t honestly say that any of the sex I’ve ever had was bad, or had immediate negative consequences or obvious risks, i.e. it wasn’t part of a plot by a roaming gang of criminals to distract me while they stole my car or something. That is not to say that I don’t necessarily regret entering into relationships with women I knew were bad for me beforehand, or even with women I found out were bad for me in the middle of it or afterwards. But as far as meaningless sex goes, no, I don’t think I really regret any of it. I’ve definitely had sex with people I probably shouldn’t have had sex with, in particular women who were already attached. But my assumption is that if I didn’t fuck them someone else would get to; I didn’t see the point of not fucking them, especially if I didn’t know their significant other. So I don’t regret it. I’m more likely to regret not having acted on a sexual impulse. See below.
4. Do you regret not having had sex with someone who you could have had sex? If yes, would you do it over and have sex?
Here’s a secret: I don’t believe in having regrets. I do my best not to concern myself with things I can’t change. Even if my own action or inaction led to the destruction of the Seattle Kingdome and the deaths of the twenty-thousand disabled children and their families watching a charity football game there*, I acknowledge that once it’s done there’s no way to reverse it and therefore I see no reason to dwell on it.** However, if I did have to pick something to regret, somewhat, it would be the handful of people who could have become sex partners and for one reason or another did not. There aren’t too many people who fall into this category, but there have been enough that I wrote a blog post on the subject. And if I had the opportunity I don’t know whether I would throw caution to the wind and remedy the situation. I say “throw caution to the wind” because I am a firm believer in the notion that the choices we make in the past determine our present. I am very happy with my life at the moment, and I would hate to change my present by altering my past even in a miniscule way. On the one hand, there are people I could have had sex with who I haven’t seen in years but who are still part of my regular fantasy rotation. I’d love to finally have sex with them. On the other hand, I’d hate to return to the present day and find that I am no longer married to Jill and enjoying the life to which I’ve grown accustomed. (Actually – is it possible to return to the present day? The question doesn’t specify if it’s Back to the Future-style time travel, or The Terminator-style time travel.)
Or even better, Time Bandits-style time travel.
5. Do you regret not having asked out or tried to hook up with someone you really liked out of fear of rejection only to later learn that person wanted you, too? If yes, please describe.
I don’t believe this has ever happened. It may have; I’ve lusted after a lot of people in my day without consummation. But I don’t recall ever finding out after deciding not to pursue that the object of my aborted pursuit would have been receptive. The closest I’ve come to this was telling M (our occasional third) that I would have loved to have fucked her in high school, but never tried due to the fact that I was in a relationship when she was single and vice versa (i.e. not out of fear of rejection); and having her tell me that she wouldn’t have said no. Oh well – water under the bridge.
6. Do you regret having done a particular sex act? If yes, please describe.
Beyond the thing with my biology teacher, which was, of course a joke? No, I don’t think so. Bearing in mind that there is a vast assortment of sex acts I’ve yet to try, I don’t think that I’ve regretted any of the ones I’ve actually done. If I put sufficient thought into it, I guess I might regret having done a particular sex act with a particular partner, or in a particular location, but I have never done something sexually that I regret in and of itself. I really wracked my brain and tried to think of specific incidents with specific people wherein I might have said something after the fact like, “I really shouldn’t have eaten her pussy that night because it sent the wrong message.” But I have no such incident in my past; I am far less analytical than this.
Bonus: Do you regret not having told someone you love them? Romantic, not familial or friendship love.
No. While I may have given my love to women who hadn’t earned it, planned to abuse it, or otherwise didn’t deserve it, I never did so under duress, and probably not even under false pretenses. When I told someone I loved them, it was how I honestly felt at the time. It may not have lasted; it may not have even been real. I may regret, in retrospect, spending as much time with the individual(s) as I did. But at the time it felt like the right thing to do and therefore I can’t regret it.
*Yes, I’m aware that the Seattle Kingdome no longer exists. I didn’t want to name an operational entity.
**Okay, this sort of thing I would probably dwell on.
Jill’s Answers
1. Do you regret how you “lost” your virginity? If yes, why and to whom would you have preferred to have lost it?
Yes, I do regret my first time. I wish I hadn’t had sex with the guy I gave my virginity to. I had waited a long time to finally have sex, much longer than most of my friends and actually longer than I wanted to. Thanks to my Catholic upbringing, I was planning on waiting until I got married to lose my virginity, but I was in my mid-twenties and began to think I might never get married and thus I might never have sex. Plus, it wasn’t like I hadn’t done other sexual things short of intercourse, so it probably seemed hypocritical to not simply do it. Anyway, I wasn’t sure that i wanted to wait until my wedding night to find out that my husband was terrible in bed. I figured that I’d better make sure that we were sexually compatible before I got married. The guy, Adam, turned out to be a liar, and an all-around asshole. First of all, Adam wasn’t even his real name so don’t worry about the possible legal ramifications of using his real name here on the blog. He was the guy I’ve occasionally mentioned who thought it was okay to fuck my ass without lubing up or even warning me. You can read more about what a piece of shit he was here. I wish I had lost my virginity to the hot guy that I made out with on the beach when I was eighteen. He and I went pretty far, including oral sex. He was an amazing kisser, and very sweet. I’m sure that I would have enjoyed having sex with him. I know it couldn’t have been worse than it was with Adam.
2. Have you ever lived a moment in your life where you said “Yeah, I’m not going to ever tell anyone about that.” Describe that moment or incident.
I’m sure that I’ve had many embarrassing moments in my life that I would love to forget about, but there is one night that I don’t think I’ve told anyone else about. It’s not something that I am proud of, nor is it something that I would ever do again. I need to preface this by saying that once I became sexually active, I enjoyed it so much that I wanted to have it all the time. As a result, I didn’t always make the safest or the most intelligent decisions. One night I went dancing with a friend. I met a cute guy, and having been drinking most of the evening he and I went out to his car and made out. He suggested that we go back to his place, and since I was drunk it sounded like a terrific idea. I found my friend and told her that I was leaving with him. She tried to talk me out of it, but of course I didn’t listen. On the way, I told him that I needed to be home before morning for whatever reason. He promised that he would drive me home when we were finished. Once we got to his place, we had great sex for hours. It was probably the best I’d ever had up until that point. When I asked him to drive me home, he said he was too drunk. He lived ten miles from my place. I walked. Looking back, walking drunk and alone through some seriously shitty neighborhoods was one of the most questionable decisions I’ve ever made. Not to mention getting in the car with a drunk stranger. I’m glad he didn’t turn out to be a serial killer.
Granted, some serial killers are easier to spot than others.
3. Do you regret having acted on a sexual impulse? If yes, please describe.
I definitely regret the night I wrote about above. While the sex was great, I don’t know if it was worth the insane risks that I took that night. I put myself in several dangerous situations, and while it ultimately turned out fine I realize that under a different set of circumstances it could have been disastrous.
4. Do you regret not having had sex with someone who you could have had sex? If yes, would you do it over and have sex?
I regret not having sex with the hot guy I mentioned in my first answer. If I had the opportunity to live out that experience all over again, I would definitely have sex with him right there on the beach. Despite the abundance of sand and its tendency to get literally everywhere, as I said before I know it would have been better than my actual first time. I also would have called the beach guy, as I said I would. I’m not sure why I didn’t call him afterwards. Maybe it was because I didn’t think I was ready to have sex and I didn’t think I would have been able to say no to him. He was a nice guy, and very hot. I could have had a great summer with him.
I can’t not invoke Grease here.
5. Do you regret not having asked out or tried to hook up with someone you really liked out of fear of rejection only to later learn that person wanted you, too? If yes, please describe.
Years ago there was a guy who was dating my friend. He was really sexy and I liked him a lot. We didn’t get together then, but about a year later I saw him again at my boyfriend’s house. We hooked up, and we were fuck buddies for about a year.
6. Do you regret having done a particular sex act? If yes, please describe.
I have enjoyed just about every sex act I’ve ever tried. The only time I can recall doing something that I didn’t like was the first time I had anal sex with the asshole I talked about above. Of course, it wasn’t consensual, so I guess that’s really not the same as deciding to try bondage and finding out that it isn’t your thing. Fortunately my sex life with Jack includes a lot of wonderful anal play. His concern for my comfort is one of the things I love about him. I’m glad that Adam, or whatever his real name was, didn’t ruin anal sex for me forever.
Bonus: Do you regret not having told someone you love them? Romantic, not familial or friendship love.
No. Not even familial. When I was younger, I remember my best friend always telling her parents she loved them, and her parents saying it back. My family wasn’t like that. We’ve always been close, but there were no outward declarations of affection. I wanted to change that. I started to tell my parents that I loved them. I remember feeling awkward and embarrassed at first. Eventually, it became normal and everyone in my family started saying it to each other. Ever since then, I have always told the people that I love that I love them. Life is too short, and I want to make sure that those to whom I am closest know my feelings.
How to play TMI Tuesday: Copy the above TMI Tuesday questions to your webspace (i.e., a blog). Answer the questions there, then leave a comment below, on this blog post, so we’ll all know where to read your responses. Please don’t forget to link to tmituesdayblog from your website!
Thank you being a very honest as always.Made me think about my own answers.Loosing my virginity was like a fairytale.What happend in the years after not so but if I ever write my own blog I let you know and you can read it (still no balloons?;)
I always adore your answers .. both so honest and open!
Happy TMI xx
I’m working on like 3 hrs sleep thanks to our baby so things are cloudy…, but I’m glad you made it explicitly clear that the biology teacher was a joke.
I didn’t pick up on that at first.
omg, i was so into Cool World when it came out, it was magical to my young adult eyes, the combination of animation and sex, i’ve never looked back since, with either the animation or the sex…
I love the answers. Jack, you crack me up. I’m kind of sad that biology teacher is a joke though. 😉 Thanks for stealing my newest, hot, man-on-man fantasy. :-p
Jill, we have so much in common in our sexual past. Plus, I made stupid decisions on the regular, so don’t feel bad about your one. I am super glad it all turned out okay, but you must first do stupid things to be old an wise! Look at it that way. NOT that you’re old. LMAO! You get the idea.
Great post, lovlies. Happy Tuesday!!
You know… that image at the top with the saying… sums everything up quite well.
I like that.
I hope you are all doing great…
~shoes~
I have to admit I read the biology teacher thing and thought it was a joke and then had a moment of “What if it wasn’t?”. I am glad you cleared it up.
Jill’s answer to No.3 reminded me of some things I did when I was younger as well. I don’t recall anything sexual that I regret but like all young people we don’t think about consequences much.
I kinda figure the biology teacher was a joke when I caught the part about you didn’t want to be in HIS class again. I know you are kinky but not that kinky. I still could kick Adams ass with my foot and no lube for the way he did Jill. Wrong just wrong. I am so glad that you helped her overcome that with you Jack.
Okay I was seriously confused about Jack’s first answer, haha. Not in a bad way, per se, but I did read it twice to clear things up for myself =P Should have opened the comments sooner, that would’ve been easier!
Love how open both of your answers are! Enjoyed reading them, as usual :)!
x
Great answers, I enjoyed reading them and look forward to reading more from the 916.
I enjoyed your answers, per usual. I’m finally up. It’s been a hectic few weeks, and I finally got regular internet today.
I posted a few more things via pre-scheduling last Friday and this Tuesday for all the naughty monkeys who want to know more. 😉