My Top 5 Most Memorable Sexual Encounters

I already know before I even begin this list that it’s going to be extremely difficult to narrow it down to the top five.  That’s probably because I’m not listing my best or my favorites but my most memorable (good and bad).  There’s a difference.  I’m a bit of a “freak in the sheets” or so I’ve been told and I crave the excitement that comes from being with people with fetishes, people who can teach me things and people who are open-minded.  Not that I don’t like romance.  I’m all for romance, but that can get a little boring after an extended period of time with the same person.  And seeing as how I haven’t been getting much lately all I have now are memories.  So here’s my list.

1.  Having sex standing up in the bathroom of a gay club in Atlanta with a hot little go-go boy while people were outside waiting to get in.  They knew what we were up to.  LOL

2.  The night that I brought home a brother from the 24-hour club and fucked him on my friend’s bed.  Then my gay/bi (he didn’t like labels) male friend came in and caught us.  He just told us to finish up and for the guy to get the hell out.  I think getting caught was the hottest part. 😉  When he walked in I was on top by the way.

3.  In reference to my gay/bi friend above…one Easter Sunday we were hanging out at the pool getting loaded and high and somehow ended up calling a friend of mine that I had been casually dating and we asked him to come over.  He picked us up, took us to a girls & guys strip club and I got my first lap dance from a woman.  It was hot.  I think that’s when my jungle fever started.  The girl who gave me the lap dance was a gorgeous dark-skinned black girl with major curves.  She was wearing one of those one-piece bathing suit type outfits that has a deep-V all the way down to below the belly button and barely covers the nipples.  It was red, white, and blue, stars & stripes.  God bless America.  LOL

Later on we went back to the apartment and had a semi-threesome.  Me in the middle sucking my friend’s dick and then reversing and my male friend sucking my gay/bi friend’s dick with me doing hand-play.  In the end I was sucking my male friend off while my gay/bi friend was behind me.  Foggy memories, but fun ones.  By the way that was a very very long time ago.  I learned a long time ago that threesomes are fun at the time, but cause nothing but trouble afterward.

4.  From threesomes to transvestites.  While I was sowing my wild oats in Atlanta my two best gay friends decided that since I was a Rocky Horror virgin we absolutely must get high and go to the midnight showing one Friday night.  So we did and it was amazing.  I know, drugs are bad, mmkay?  Don’t judge me.  I was sowing my wild oats for Pete’s sake.  Anyway, I think this started my thing for transvestites.  Well, that and going to see Charlie Brown’s Cabaret three times a week.  God Bless the Drag Queens.

So one night while hanging out at our usual 24-hour club waiting on the drag show to start I caught a woman eying me from the other end of the very large rectangular bar.  I thought she was a woman.  Then my friend quickly informed me that she was a he.  I was a little shocked at first, but he/she kept on making eye contact and finally came over to talk to me.  Up close she didn’t look as much like a woman as from afar, but I still found her appealing.  I don’t know if it was more curiosity or horniness that got me to actually go back to the hotel with her.  Once we got to the hotel I was actually trying to get her/him to remove the wig, but he wanted to keep it on so I just went with the flow.  It was not really the greatest sex, but it was so exciting and different, and he was pleasantly well endowed, that I think I came at least five times that night before leaving him in a crumpled ecstasy-induced sleep on the bed and heading home.  If marijuana is a gateway drug into harder drugs like cocaine (bullshit by the way), then sleeping with a transvestite was my gateway into lesbianism.

5.  As I said in the beginning, not all of these are good memorable experiences.  My worst and most memorable sexual experience was all thanks to a cute frat-boy type sports writer.  He was in town covering the NY Knicks game and asked if I wanted free tickets and that I could bring a friend.  Once the game was over we would have time to go out for a drink and hang out.  I’m a sucker for anything free and especially if it involves a hot guy and possible hot sex with said hot guy, so I quickly accepted.  The game was great, I had a few beers with my friend and even got to see JFK Jr. sitting down in the floor seats.

After the game we all went to a bar and had some drinks.  My friend BSL decided it was time for him to split so that my hottie and I could have some alone time.  We had a few more drinks and then decided to go back to his hotel room.  This guy was so hot that I was ready to rip his clothes of right there in the elevator, but I kept my composure until we got to the room.  Things seemed to be going great, then he decided that he wanted anal.  I don’t do anal and I told him that I wasn’t into that.  I have a perfectly tight pussy, so why should a guy have to fuck me up the ass?  He insisted that I would enjoy it.  I should have gotten up and left right then but I didn’t.  He started doing it, no lube, nothing.  It was the most painful thing I had ever experienced.  I yelled at him to stop and finally had to push him off of me to get him to stop.  I immediately got dressed and left, never to speak to him again.

I’m not saying it was rape, but it definitely crossed a line.  I was in so much pain the next day that I couldn’t even get out of bed.  Lesson learned: never trust any man and never give in to their sweet talking.  Sad for me to admit, but I’m still working on that last part.  I give in to sweet talkers entirely too easily.  But when push comes to shove, I have no problem kicking a guy in the nuts if he is hurting me and refuses to stop.

I felt compelled to add the last one because there are pros and cons when it comes to sex.  Women especially have to be careful.  Besides being safe and using protection, you have to be safe in other ways too.  Not all sex is fun and exciting.  Sometimes it can be painful and traumatic.

With that said, happy humping.

12 thoughts on “My Top 5 Most Memorable Sexual Encounters

  1. Wow! Mrs… you sure do say it as it is.
    I admire you for being so open about your sex life and if I am honest I was no goody goody in my younger years, so I cannot throw stones ( English proverb)

    Now mine IS and WILL STAY just a memory

  2. Have you ever seen the series “Diary of a Call Girl” with Billie Piper? Not that you’re a csll girl, but your love life deserves to be documented somewhere. Good job.

    • Ah, thanks for the laugh! Yes, I have seen that show. I loved it, and Billie Piper is hot. LOL Loved her on Dr. Who too. 🙂

      This is the documentation of my crazy love life. Slowly, but surely it’ll all be here.

  3. Pingback: How’s a girl supposed to get any sleep around here? « Confessions of a Preacher's Daughter

  4. Pingback: My Top 5 Threesomes « Confessions of a Preacher's Daughter

  5. Somehow I missed this article. You my dear have run the gauntlet. I’m considering starting another blog dedicated to my wild and varied experiences, what do you think I should do?

    And no lube during back door entry, hell no!! Oh well, you live, you learn.

    • I will but I have had a problem with anal sex ever since it was forced on me. I just won’t try it again.

  6. Well I am not into force. You have no idea how pleasurable it is to have a guy licking and tongue fucking your anus. There are more pleasurable nerve endings there than in your vagina. The key is for you to be in control using lots of KY and you get on top and once you have fully impaled your self on him STOP and let your anus relax around his penis. Then start moving slowly according to your pleasure adjusting for just the right angle and gradually pick up speed and intensity as the feelings move you.l This is best done while simultaneously using a vibe on your clitty at the same time

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