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?
1. Do you regret how you “lost” your virginity? If yes, why and to whom would you have preferred to have lost it?
No, I don’t regret either of the ways I lost my virginity. I say “either of the ways” because some people don’t consider my first time as having officially lost it. The first time I had sex, I fucked a prostitute that an older friend of mine pushed on me. The reason people don’t think it counts is because I didn’t orgasm. The second time was with a woman I loved deeply. She said nothing as I entered her bare, and when I came inside of her, she stroked my back and got downright giddy as I confirmed that I did indeed let loose inside 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.
Yes, but like the question states, “I’m not going to ever tell anyone about that.” In fact, those moments are a bit too copious in my personal history. Cop out? Hells yeah.3. Do you regret having acted on a sexual impulse? If yes, please describe.
Yes. The most immediate memory is with my wife and my first co-girlfriend. We had left for a year and Raquel and us had fallen out prior to our departure from the area. Shortly after we returned, a friend brought me over to visit Raquel because she had found out I returned and wanted to see me again. One thing led to another and I had sex with her for close to 10 hours straight. This should have been a clue that something was amiss. The very catalyst of our previous break-up was her out-of-control drug use. I allowed myself to not even question why she was all over me and eager to get it on. I guess most of me wanted to believe she missed me that much. In the end, she treated me like a user, an exploiter. She had expected better of me, expected me to decline sex, try to talk her out of doing anymore drugs, and so on. I was blinded by her eagerness and that amazing sex drive she seemed to fling my way. The night severed the final ties between us in her mind and for years when I’d see her out and about, she was visibly frightened of me.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?
No, but there are times I wish I would have. Most of these types of unrealized sexual encounters were when I was in high school. A couple were even with girls I had crushes on. At my English Major end-of-year party in 2005, two women all but said “Let’s fuck, like right now.” Those two blew my mind because I had no clue they wanted me in any way whatsoever. About a month later, one of them who was also my upstairs’ neighbor banged her boyfriend for a few hours. She was loud and sounded incredible...Okay, so maybe she was someone I really regret not having hooked up with at least once.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.
Yes, especially those girls in high school that later told me they had crushes on me. It’s just I had such abysmal self-esteem that I didn’t believe any except the ugliest and most desperate of girls would want to be with me. College did wonders for my self-esteem.6. Do you regret having done a particular sex act? If yes, please describe.
Not that I can think of at the moment.
Updated 30 September 2012:
I completely forgot about one sexual encounter that I stopped before it got into full swing. I have since performed the sex act itself, so it's not a completely accurate answer to the question. However, I deeply regret not having moved a man one inch lower when he tried to fuck me when I was twenty-one.
We both worked for a company that had us staying over night on each run in a distant town. They would put us up in these two-room apartments each with two beds. I knew the guy I was rooming with was openly gay. He was my friend and I had no problem with that. In fact, I secretly hoped he'd make a move some day. Then one night, the first and only time we shared a room, I swore I heard that distinctive fapping sound. I rolled toward him, heard the fapping cease then continue once I faked sleep breathing. Sure enough, the guy was jerking off to me. That's when I said something.
Next thing you know, he's on top of me in missionary and pushing the tip of his dick into my kack. I'm pretty sure he thought he was lined up properly and just had to bust through my sphincter. The bed was squeaking like a mother and that worried me with an overtly macho and big mouthed coworker in the next room, so I stopped him. Had I merely moved him one inch lower, he would have worked his dick up my ass and I wouldn't have stopped him until he was a quivering mass atop me.Bonus: Do you regret not having told someone you love them? Romantic, not familial or friendship love.
I have a tendency to fall in love and tell the person I love them a bit too quickly, so no.