Best/worse sex you ever had...

Patryn

Literotica Guru
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Feb 29, 2000
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Okay people, back to the matter, umm....at hand. :) Warning, long ass post.

What is the best sex you ever had? What was it that made it so good? Conversely, what was the worst, and the reason for that?

I'll go first, obviously. Best sex I ever had:

There was a married guy I was seeing shortly before I myself got married. (I know, OK? You don't have to say it. :)) To this day, I can't really classify the relationship, but believe it or not, it was one of the best, healthiest ones I've ever had. We were amazing close as friends, and also extremely in lust with one another. He told me, and knowing him, I believe it, that he never loved his wife any less the whole time he was in love with me, which leads me to believe there is more than one "perfect" person out there for everyone.

But I digress. There was a lot of flirting and teasing when we first got to know each other, stopping just short of actually doing anything. One night I just finally couldn't take it any more, and being 99% sure he'd let me, I kissed him. Well, he did let me, but only to a point. I never forced him to do anything, because, basically, I couldn't...how do you force a man? And if he really didn't want to, I would have stopped. He was after all, and above everything else, a friend. This was one of those cases where "no" meant "maybe".

So I kind of had to talk him into it. I knew he wanted to, or he never would have done or said some of the things he did or said, and he wouldn't have played tonsil hockey with me for 10 minutes. I know how smarmy it sounds, but it was a rush getting him to realize that fact and give in. Like I said, I didn't coerce him, and it was totally consensual. Location was part of his nerves...we weren't exactly in the most private place.

What made is so good was that he was slightly dominant, while I am slightly submissive. He wasn't afraid to "take", and I wasn't afraid to let him. Also that it was finally the culmination of months and months of fantasies and flirting. We were finally going to do what we'd both wanted for so damn long.

It was also good because we completely and totally trusted each other, and knew there was no committment...that it was just whatever it was for however long it lasted. On the physical level, we fit each other perfectly, and he was never afraid to ask me what I wanted, or if I liked it. Neither was I. The sex was a physical expression of trust, but it was also about exploration and experimentation, not totally about "making love", if you will. It was mostly just to feel good with someone we trusted. We remain friends to this day, though we don't have a physical relationship any more.

The worst...hmm...that would be a few months after he and I "split up"....or whatever I was at a friend's house, who I knew was attracted to me, but I didn't reciprocate. We both got pretty drunk, and he said to me, "You've been here all this time, and I haven't even gotten a kiss". I don't know why I did it, honestly. Again, it was consensual, if I had said no, he would have respected it. I suppose it was just an "I'm drunk, why the hell not" sort of thing. :)

I had no real feelings for this guy, we weren't even terribly close friends. The sex was, well, less than stellar. What are those British soldiers called? Oh yeah, minute men. I don't really regret it, but it's just like, why?
 
The best:
With my wife. I know what you're thinking, but she doesn't even read the board. Even if she did, I wouldn't say anything different. She is my fantasy Goddess and even while masturbating, I think about her. She and I have always been open to experimenting and playing and the trust that she shows me and I have for her make the sex incredible.

The worst:
Hate to say it, but also with my wife. Right now we are trying to get pregnant (her, not me) and the doc has us on a schedule that has us "shagging" every other night. While some nights are spectacular, other nights are just mechanical. Damn shame, but there it is.
 
I hear that one...for a while my ex and I were trying to start a family, and while having sex every night sounds fun in theory, it can get pretty dern boring after a while.
 
One of the Best Sexual Experiences I Ever Had was with the guy I told you all about awhile back (the one that I met online here at Lit). It was so good because there was such an intense emotional connection between us. Oh yeah... he was also just good at sex to begin with! But anyway, we knew everything about each other... even from the first day we "met." We'd talked for about 4 months online every day for at least 2 or 3 hours, but mostly for about 8 hours while we were both at work, and then at night on the phone. By the time we finally met, how could the sex have been anything else but spectacular?

Worst Sex?? Hmm... which to choose, which to choose!
AHHH!!! It would definitely have to be with this one guy I'd seen around at parties and such, and eventually met through a friend. We ended up hooking up at one of my friend's houses, and one thing led to another. I knew I wasn't all that into it... and I didn't realize he wasn't either until I reached down to touch him (we'd been making out for about 20 miutes... my shirt is off, everything), and he's as limp as a wet noodle. I am happy at first... maybe I can leave. But no. He says he's always like that blah, blah, blah... so I say, okay. Maybe I can give him a BJ and that'll be that. I'll just go home and hopefully never see him again. But no. He can't get hard from a BJ. Shit, I even masturbated for him at the same time... I tried EVERYTHING I knew, and he couldn't get it up. This is about an hour later. I stop, visibly angry. I want to go home. But no. He starts CRYING. I feel bad and stay and try some more. Another HOUR AND A HALF goes by. Finally he has somewhat of an erection, and he says, "NOW NOW! Let me put it in you... " It took some work to force it in... the condom was baggy and his dick was soft. Needless to say, he eventually DID get an erection and it lasted for all of 30 seconds. Complete waste of my time. And the worst part of all... He doesn't understand why I won't go there again?!?
 
Mmmm.. ok, worst sex was with my ex hubby. We were together for 8 yrs and God knows how I stayed with that man for so long when all he could do was get it up, put it in and pull it out. 2 min. max. whoo hoo... Not fun. Pissed me off. I faked orgasms with him for 3 yrs until I finally told him that he'd not been doing his job. Needless to say THAT didn't help our sex life. hehe.

Best? That's hard. Two instances stick out in my mind the most. One was with a guy I started dating about a year after my divorce. I was just starting to bloom sexually and was up for just about anything, mostly he was conservative but would attempt my little experiments. One night he "forced" himself on me and I swear, it was so damn hot... we did A LOT of things together that were really cool and fun. I dominated him one time and he LOVED it.. hehe..

The other one was just last weekend. MMmmmmmm... let me say that that man knows his business!! He's an old friend of mine and we'd been lovers in the past but had just got together last weekend because it had been 3 months for me and I was OVER it... laughing... he's black 6'8 and built... mmmm... very hot lover, never enjoyed oral sex until he rolled around and let me tell you,that man can lick pussy! laughing...
 
Best was with a scorpio mom. She had 4 kids, was in her early 30s, but could have passed for early 20s. I came 5 times in 3 hours. Now I've met another Scorp who had sex with a Scorpio man 7 times in 5 hours. My goal is surpass that.

worst? well.. you forget about those
 
Stealing a DCL line but I can't resist...

Scorpio women ... nahhh. The truly great sex is to be had with women whos first name begins with a vowel. They are without fail THE best.
 
You mean it gets better?

Tiggs told me to come back and post under this so I thought... "What the hell?"

Anyway, I would have to say my best lover was my first... I was young, he was a bit older (3 years) and I thought back then that I was a rebel because my parent's hated him and I would have done anything to make them mad. So, one stormy night, we went to an empty baseball field and had our first sexual encounter. I thought that was great then but it did get better over the 4 years we stayed together.

My worst, all I can say is... Remember Jay, Tiggie? haha

http://smilecwm.tripod.com/net/smileysex5.gif
 
Patryn said:
What is the best sex you ever had? What was it that made it so good? Conversely, what was the worst, and the reason for that?

Best sex I ever had? Well, I can't narrow this down to one specif time, but I can narrow it down to one person. He was a man I met from Yahoo back when I was 21. Then, he was 40. Though I was quite experienced sexually by the time I was 21, I still had many firsts with this man. He did things to me that no other man ever had. :) Over the course of 2 years, I have been with him off and on, and I would have to say he's the best lover I've ever had.

Worst sex I've ever had? Again, I'd have to answer this one in the form of a lover, not a specific act. Once again, I was 21 for this one... ;) There was a girl, who was a pretty good friend of mine. She married a guy who was an ex b/f of mine (but that's another story all together). She was "bi curious" and we had been together a few times. (One time being a 3some with her husband.) Anyway, she'd just lie there and not move. Her breathing never changed, and she never made a sound. It was like she was dead. (And I know it was not my "fault" because I have had many other female lovers, and they were quite vocal!)

~Goddess Tiggs~
http://smilecwm.tripod.com/net6/lew.gif http://smilecwm.tripod.com/cwm/la.gif

P.S.
ROFLMFAO Ezzie!!
 
The worst would have to be a tie between my first time (I didn't know the first thing about what to expect) it hurt and it turned out he was gay - and the time that I literally fell asleep "during".

The best, hmm...gonna have to break tht down a wee bit: Best oral was a guy I knew who had a pierced tongue. Best ride was my the brother of a good friend. Best over all: still taking applications.
 
My first was the worst and the best was a girl who was a sprinter with a local athletic's club ( lord she could wear a boy out ).
 
Ya' have ta' appreciate athleticism Outsider;)
 
Ohhhhh yeah you got that right EX.

And long leg's and shaved pussy and a willingness to at least try anal and then find out they like it.
 
Athletic women in an "experimental stage"... pass the vitamine E please.
 
Worst was with my ex-husband, great step-dad, wonderful cook, lousy in bed. He was at heart a good Catholic school boy & no matter what, I could not get rid of his inhibitions.



I hope the best is yet to come. The man I am with now is amazing. In the 4 years we have been together, the sex just keeps getting better & better. I never dreamed it would be like this. He is a non-smoker & non-drinker, so oral sex is awesome. I never liked giving oral before, now I love it! He has no inhibitions & is up for anything. He is also very intelligent & well read, that is a huge turn on for me.

P.S. Outsider, where are those kilt pictures?? I thought about you when I saw the guys in their kilts at the Faire today. (wink, wink, nudge, nudge)
 
Bad new's

I moved in to my present flat just over a year ago and had my highland dress in storage at a mate's house and when I called him last week about the stuff he checked on it for me and found that his wife had given my stuff to charity...?

Ho hum never mind I'll just have to get new gear when I get a new job.

BTW read ho hum as "fuckingcuntingshitingassholeingwank".
 
I was a little taken aback at your blase atitude....at first. That stuff is hugely expensive!

The kilt alone (a quality one) pushes a thousand canadian
 
Oh you better believe I was not a happy bunny but the guy and his wife are friend's from my school days and have known me for more than half my life and have dug me out of a hole so many time's I can't count.
 
Major bummer for us ladies, Outsider. I have a friend who makes kilts for some of the local Highland gamers. I was amazed at how expensive they are. Well, once you get the new kilt, remember you owe us some pictures. That will definitely give us something to look forward to.
 
WriterDom...that's interesting. The guy I mentioned as best happens to be a Scorpio. Though I've never taken much stock in astrology, that does set me to wondering.
 
BTW

I just remembered something I happen to live half an hour from a shop that does nothing but highland dress and they are good people so if Laurel ( hope I spelled your name right ) doesn''t mind I'd like to plug them.

The Tartan Cupboard 2a Greenwich Market London SE10.
Telephone:- 020 8858 0038

Sorry I don't know the international code but they are good and will find a tartan to go with just about any name, also a new range of Irish tartan's are now available.
 
I was once with a guy who only took less than a minute to finish. I think that's enough said.
 
For the U.K. diall 011 for international access, then 44 for the country code. I think when calling from out of the country, you drop the first 0. Thus, 011-44-20-8858-0038. Hopefully that's right.
 
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