Highs and Lows – My answers
Here is a link to these questions (without my answers) to copy and answer on your own blog: Your Sex Questions Set 6: Highs and Lows
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Highs & Lows
Question 1: Describe your worst all time sexual fail?
Lexy was by far the hottest sophomore cheerleader and everyone new it. I had a crush on her since the first time I saw her, the first week of high school – she was cheering at a pep rally,
Lex wasn’t just hot, she was authentic and interesting – she barely knew I existed, until my senior year when she participated in the class play with me. Lex and I became good friends, she even kissed me once and then immediately returned me to the friend zone. She was too good for me – out of my league.
I went away to college and became cool (LOL), and then moved back. I must have ran into Lex somewhere, I don’t remember, but we reconnected and ended up hanging out one night. We both had recently become single – the first time ever that both of us were totally single and in the same town.
We hung out on the patio of a popular brewery for several hours and talked, and drank. We got talking about sex — she was complaining about her sexual experiences and telling me how she never has an orgasm.. The guys she had slept with had been selfish, or not good in bed, and none of them ever lasted long enough.
As we talked, without telling her directly how much better I would be than the others, in so many words I let her know that I was a good fuck, and that I do right all the things that she complained others did wrong. I think I even told her right out that most girls that have sex with me have orgasms. That part was true, and I didn’t suck in bed, but I was way over selling.
Lex must have believed my big talk because she made a bold move — after we had been talking about sex for a good hour, Lex calmly asked if I wanted to leave and go have sex at my place. I doubt that she even considered dating me . I think she was just convinced the sex would be good and maybe make her cum finally – perhaps she was open to an ongoing fuck buddy, I ever got to find out.
After all of the big talk, I came as soon as I got inside of her. I had wanted Lex for so many years, and never dreamed that she would be on her back naked, spreading her legs and letting me in. It was the biggest fail ever and Lex never gave me a do over. I wanted to do it again and redeem myself that night, but it got weird quick and she took off soon after the sex disaster. That was the last time I saw her until our ten year high school reunion – she was married.
Question 2: Hottest sexual experience with someone who you never dated? (doesn’t have to be intercourse) Could be a hookup, incident, interaction.
Hard to say which was the hottest, so I’ll go with the hottest (perhaps) that I haven’t blogged about already.
My family went to Club Med for two weeks over the Christmas holidays when I was 19. I made friends with two women who were their. They were friends in their early forties, I don’t think they were married but it’s possible that they were and left their husbands at home. The one I connected with most was an accounted – her name was CJ – I still have some photos of us three.
I met them on the third or fourth day of the trip at the tennis courts – they were tennis players too. The day after I met them on the courts, I partied with them at the disco – we had enough shots to kill an elephant.
I went back to their casita with them and had a three-way of sorts. They were topless – CJ had her pants off (panties on) and lost my trunks at some point. I took turns making out with them. They were both touching me and CJ swallowed while her friend watched.
Somehow, after we were in CJ’s bed and before we actually started having sex, the two got in a fight. I can’t remember what started it – I don’t know if I ever knew what started it. I guess I passed out right after that, because the next thing I remember was waking up naked in CJ’s bed. They were gone, to breakfast or tennis or somewhere.
I felt guilty and uncomfortable after that, they probably did too because of the age difference, and I didn’t hang around them after that. A couple nights before we left, CJ approached me in the disco, wanting to talk – asked if I would take a walk with her. She said she wanted to say good by and wanted to apologized if they freaked me out. (again, I was over 20 years younger).
On our walk we started kissing and she asked me to have sex with her, right there by the beach on a patch of grass. No condom, no knowledge if she was on birth control – thank god I didn’t catch anything – can’t guarantee I’m not a father but unlikely.
Question 3: One or two hottest things somebody has done or said – those moments that stick in your mind – the hot little highlights of what you’ve seen people do? This could be something you just saw happen, or something you participated in.
One of those times I wrote about – here is a link: Janice: True Story – Most interesting thing that ever happened camping – Scandalous
Another thing that stands out that someone did — when a girl had a rose and a note delivered to me while I was in makeup before performing in a play my last year of college.
“Good luck tonight, signed someone who’s had a crush on you all year.”
After the play she revealed herself – I think she was a costume designer – someone one in the theatre department. She asked if she could drive me back to my apartment (I must have walked to campus). She wanted to sleep with me, but I didn’t want to – in a circle like we were in, your next girlfriend or lay would only be of the sexual market value as the last person everyone knew you hooked up with. It’s gross I know, but it would have been a hit to my prospects. She then asked me if she could give me head at least, and I let her. Please don’t think I’m a pig, I was young – I’ve long since discovered empathy and been humbled in every excruciating way you could imagine.
Question 4: Describe your most interesting sexual height or extreme. This could be the time your got the most wild, did the naughtiest – longest, craziest, most over the top, most people involved, sluttiest, most sexual day – most partners in a day, your personal sexual Guinness record of some kind?
These questions are trouble – can somebody please shoot the author?
Most extreme for sure was demonstrating my mind masturbating trick in front of a number of friends, four girls two guys. Thank god I pulled it off or it would have been a much more embarrassing memory. But, what could have been weird had I not pulled it off, was to astound and amuse my audience in nearly legendary fashion.
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