TMI - Will I regret writing this?

Any Regrets?

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?

When I think of sexual regrets, it is much more than simply picking the wrong person or the right person or the right/wrong time/place whatever.  It brings into question my faith, my beliefs, my upbringing, and eventually, well, now, it makes me question how I raise my kids, how I answer their questions, how I conflict with my wife, and what I tell my 16-year old daughter when she starts dating and liking boys. 

So forgive me if my answers are conflicted, this week’s TMI might really be TMI.  Or, most likely, with only a few minutes to write I will give the funny, sexy, interesting answer instead of the real one.

1. Do you regret how you “lost” your virginity? If yes, why and to whom would you have preferred to have lost it?

I lost my virginity to my wife on my wedding night in a hotel bed we only slept in once.  We had tried in the shower after the reception, but it didn’t work, a great disappointment to her since it was one of her few fantasies.  I think I’ve blogged about this before, but I came in about three thrusts, luckily, she came in two.

Who should I have lost it to?  KS in college.  She was stunningly beautiful, artistic, troubled, funny, wild, and she realized I was still a little boy trapped in a man’s body.  She knew what I wanted, what I needed, I loved her madly, but couldn’t give her what she needed.  There were moments when I stopped myself, when I put limits on what I would do in the name of virginity and marriage and God.  I don’t denigrate any of those ideals, but looking back, I should have loved her more.  She needed me, and I know I needed 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.

Where to start?  Is there a statute of limitations on these stories?

There was the naked circle jerk with 5 teenage boys in the woods.

The time I got Mindy to undress for me, I think we were 12.

The time my brother made my friend and I give him a hand job.

After turning 18 I got a little smarter, but not by much.

I made out with my best friend’s girlfriend, which backfired on everyone.

I dated my boss.  Very bad idea, though now days, I could have filed a harassment suit and paid for college.

3. Do you regret having acted on a sexual impulse? If yes, please describe.

I dated Michelle, the broke up, and then took her out again months later.  She was even more straight-laced than me, but I had discovered boobs by our 2^nd round, and boy did I want hers.  Later she described our date to her little sister, who told my brother, as “date rape” and I always felt bad that she remembered it that way, but worse, that I acted in a way that made her feel that way.  I was an ass at times.

Early on, after just discovering Skype, I had an encounter with a woman who was so obviously messed up that by the end of our time, she was in tears and I was a bit freaked out.  I didn’t find her attractive in any way, I was just fascinated that another human would do that, on camera, for me to watch.  In retrospect she should not have been there, I should not have enabled her, and we should have both called our therapists.

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?

Someone I could have had sex with?  Because I always regret not nailing Christy Brinkley in the 80’s and Elle McPhearson in the 90’s…..  But they don’t count.

But, I should have been with KS, KA, and KH.  I had a thing for “K” names I guess. 

KS because we loved each other.

KA because she would have been amazingly good.

KH because she needed me to accept her without condition.

BJ only because she was a prickly little bitch who could have used a good ass fucking, but that sounds pretty “rape-y” so I won’t write that down.

LB so she would have not been so scared on her wedding night (her confession to me many years later).

AB because she was so amazingly hot and, after her divorce, she would have taken me.

And a couple of very special blogger friends that just didn’t workout (yet).

Would I do it differently if I could have?  That’s an impossible question to answer.  If I would have said yes to KS, then I would have had to break with my church upbringing, my faith, my parents might have kicked me out of the house.  Had I slept with KS we would have moved in together as we discussed and everything would have been different.  Same thing with CJ, the connection was deep, instantaneous, and powerful, sex with them would have changed the entire trajectory of my life.  And when you start examining regrets at that level, it’s a deep dark pit you are digging.

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.

Rejection, both actual and feared, has ruled my life, so YES.  I was pretty clueless in high school about who liked me.  At my 10^th class reunion, I introduced my wife (then fiancé) to several old girlfriends, a couple of which described me as the target of their affections back in the day.  I had no idea.  I missed out on so much.

6. Do you regret having done a particular sex act? If yes, please describe.

I made CJ cum again and again over the course of 3 days of making out and dry humping as freshman in college when we first discovered the beauty of a shared orgasm.  She fell in love with me, I did not return the favor.  It got messy after that.

Bonus: Do you regret not having told someone you love them? Romantic, not familial or friendship love.

There are bloggers that I love and who love me, but it seems pointless to say it, to entangle ourselves further when nothing can be done about it.  However, being loved, and loving, is never pointless.  Frustrating, perhaps, but never pointless.

I should have told KS that I loved her, because I truly did.  With all of her flaws, her troubled past, our differences in practically everything, I should have wrapped her up in my arms and told her that I loved her.  Perhaps then I would have had the courage to move forward with her, for what would have been an amazing ride.

OK, I need to stop now.