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Blog Chain - Best Sex Ever?

This month’s challenge is a difficult one. “The best sex you’ve ever had”. Where do you even start?

I have written a lot about a lot of sex over the past 6 ½ years I’ve been doing this blog, actually closer to seven, but what does it mean, “The Best Ever?”

Do I talk about first times with various friends? Those rare and precious moments of discovery when you realize that you can make another person come? Do I talk about the shiver I felt as I held her tightly in my arms while she talked on the phone to her mother and my fingers sneaks down the front of her jeans and underneath the thin silk of her bra? Do I talk about fumbling discovery underneath the bell tower during freshman year when I realized that even with jeans on things can feel pretty good. Do I recall that moment when I realized that she was going to come as well and all she could say was “don’t stop, don’t stop, don’t stop.”?

Even though I complain a lot about sex, and the lack thereof, I am sitting at my desk enjoying a lovely refractory moment after a phone call with a very special friend. 

Is the best sex you’ve ever had the most recent sex? 

I know I’m asking a lot of questions instead of giving answers. I can say that I had some really bad sex on Sunday night but it was bad sex only in retrospect, the sex itself was great, it was the conversation that it sparked afterwards that was discouraging and will be part of a future post. Sometimes the best sex you ever had only becomes that as it becomes a memory. You realize it was the last time you are with someone special so it takes on nostalgic importance. Sometimes you realize that by comparison, it was the best, you just did not know it at the time

You can categorize “best” and put it in context.

  • Best first time
  • Best time at a strip club
  • Best time with the wife
  • Best time on the phone
  • Best time at a dance club
  • Best time in a car, dorm room, swimming pool.

How do you pick out of so many wonderful memories?

I would imagine that my friends who are actively seeking new partners would have the same dilemma. How do you compare lovers? How do you compare cocks and cunts? They are also different, so wonderful in their own way, or so horrible in just as many different ways.  How do I compare online friends to real-life lovers? I have never had a lover in real life have eight orgasms, but online, when the stars aligned, it happened twice. Online I’ve had conversations that lasted for two hours, two hours of play, fun, touching, and cumming, while, in the real world, 30 minutes is impressive, and 45 is a marathon. At least, that is, since I’ve been married.

And how do you compare married sex to single-sex? Are they even the same thing? Single sex is about fun and exploring and daring and discovery, and married sex, well, it’s different. Married sex becomes familiar, intimate, powerful, loving, vindictive, or just routine. Do I compare my best sex of the last year to the first year my marriage? How does Year 1 compared to Year 20?

And I have had a lot of good orgasms that had nothing to do with sex with someone else. Does that count?

Blog posts that ask more questions than they answer are fairly pathetic but I can’t pick without giving some context.

I sit here and think back about all the wonderful friends I’ve had. Friends, lovers, strippers, random strangers, two lesbians (not at the same time), my best friend’s girlfriend, my girlfriend’s best friend, my girlfriend’s roommate; if I look back over the years I’ve been very lucky. I really should stop complaining.

Let’s stop philosophizing and get down to some favorites.

I’m going to list more than one, maybe that’s cheating, but too bad.

“Best first for me”- You have to remember I was a late starter.  It was my freshman year at college and I stay up started dating a girl from my hometown. I think we had gone bowling and decided to make out on the way home underneath the statue of the school’s founder. It was a popular spot. I remember she was wearing velour pants, (forgive her, it was the 80s) and as she locked her legs around me, pulling my hard cock tighter and tighter against her soft folds, I realized that I was about to make her cum and I exploded. She soon followed. I remember it like it was yesterday and it was 30 years ago. I think that qualifies as “best.” We stayed together for three more months, it ended badly.

“Best first time for her” - I almost married this one, cute, blonde sweet, and she liked to hike and play outside. We were in her car tangled up on the passenger side as my hands slipped down her pants and touched her intimately for the first time. It might have been the first orgasm she ever had, it certainly was the first one with a boy, and it was insanely powerful  I mean insane as in crazy, wild-eyed, loss of control “oh fuck what is happening to me” crazy.. I can still remember her in my arms panting, gasping for breath, and all she could say was “I want more.” I was silly and misunderstood and gave her another with my fingers. That is not what she meant by “more.”

“Best time with a stripper” – Two fit into this category. #1 is easy to pick.  Niagara Falls Canada, I don’t remember the name of the club, but they allow full contact naked lap dances and I fell in love. She stayed with me for a half an hour though I only paid for three songs, she actually kissed me, and when I finished while she rode me gently to orgasm, I was ready to move north. #2 makes the list only because it was the first time I climaxed in a room full of people while someone else watched. It’s hard to forget that moment.

I shouldn’t be saying all these, they all would make great blog posts of their own, and I’ve gone over my thousand word limit by quite a few. Maybe I’ll save some for later, some of those that improved with memory, some that faded, the first time with my wife, the first time with someone else besides my wife. I’ve been lucky enough to have many “best” times. I hope you have been as lucky.

If you want to join in the blog chain, please go to "Prowling with Kat " and let her know!!!
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