TMI Tuesday: October 23, 2012 - Then & Now

Thank you to the TMI Tuesday reader who submitted the following THEN AND NOW questions. He wanted to remain anonymous.

Jack's Answers

1. What one part of your sex life today would most surprise the 17 year old you?

Probably the quality, and for that matter the quantity, of sex that I have.  At seventeen I was relatively new to sex, and while I enjoyed my early sexual experiences there was nothing particularly great about them.  Sure, having sex at seventeen was a pretty big ego boost, but it was fairly unimaginative in comparison.  Nothing against my girlfriend at the time, but it's clear to me today that she was somewhat repressed and not very open to new experiences.  The sex we had was limited to missionary and cowgirl, and if memory serves she never gave me head.  In light of that, the thought of the oral sex I get from Jill on a regular basis - and for that matter just how much better sex can be than what I was experiencing at seventeen - would likely blow my teenaged mind.

2. What one thing might shock that younger you?

I'm inclined to repeat my answer to #1 here, but in the interest of coming up with something fairly original I'll instead say my interest in exhibitionism.  I've always been a voyeur, obviously.  But being an exhibitionist doesn't necessarily go hand in hand, and the amount of gratification I get from having sex in a public or semi-public setting, or on Skype, is something that not only could I not have foreseen when I was younger, but in fact I considered a turn-off.

3. What part of the younger you’s (not necessarily at age 17) sex life do you look back on with the most nostalgia?

I'm going to say the early stages of a new sexual relationship.  There's something very exciting about the anticipation that precedes a first-time sexual encounter, and about seeing someone naked for the first time.  I'll wager that most people feel the same way I do, and this is why I find monogamy such a spurious arrangement.

4. Is there anything in the younger you’s sexual ambitions or fantasies you have not yet fulfilled?

I don't think so.  The most outlandish fantasy I harbored when I was younger was to have a threesome or some other manner of group sex, and I've had that.  I suppose that I fantasized about specific individuals, including not only people I knew personally but also celebrities; however I gave up on such fantasies many years ago, realizing that in many cases it was futile, and I find few things more unsatisfying than an impossible-to-fulfill fantasy.

Bonus:  Give your 17 year old self a piece of sexual advice.

Be honest with potential lovers about just how important sex is to you.  Don't downplay your need for an exciting, varied sex life for fear of scaring them away.  If the truth about your sexuality scares them away, you're better off.

Jill's Answers

1. What one part of your sex life today would most surprise the 17 year old you?

Probably my exhibitionist side.  I was very shy at 17.  I never would have imagined that I would have sex in public, notably at a sex club in front of a wall of men with their cocks out, and enjoy every second.  I couldn't have foreseen webcamming in front of strangers, or doing a striptease and masturbating in front of close friends.  But today these are all treasured memories, and for that matter things I would do again in a heartbeat given the opportunity.

2. What one thing might shock that younger you?

That I've had sex with women.  I don't want to make it sound like I was a prude when I was younger, but while I've always considered women attractive I don't think that having sex with one in the context of a threesome was something I was expecting to do.  Actually, scratch that.  The thing that would probably shock the younger me the most is the fact that I've allowed my husband to interact sexually with another woman during a threesome.  

3. What part of the younger you’s (not necessarily at age 17) sex life do you look back on with the most nostalgia?

Probably the early stages of a new relationship.  The first kiss, the first touch.  Sharing and exploring your sexuality with a new partner, finding your way around his body, learning his sexual likes and dislikes.  Learning his sexual responses.  Being explored for the first time.

4. Is there anything in the younger you’s sexual ambitions or fantasies you have not yet fulfilled?

No.  I have fulfilled most if not all of my younger fantasies.  Those sexual ambitions were very romantic and sweet.  My current fantasies are more about enjoying, and being enjoyed by, two guys at once.  That one still remains a deeply-held fantasy.

Bonus:  Give your 17 year old self a piece of sexual advice.

You are sexy!  Embrace it!  Don't ever try to hide it.

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