What's Your First "Holy Shit" Sexual Memory?

At a friend's house, he showed me some of his dad's porn mags and I learned the anatomical differences between males and females. Unfortunately, I had to leave early to get fitted for a tux for my wedding.

What a nice way to start the day, Eve. A great way for your brain to say thanks to your body for supporting it.

First one? As a young guy waking up to the same probably and making a bit of a mess of the bed.

Fucking my neighbors wife. She was 40 and I was 15

I was 24, living in a townhouse in OKC. The neighbors in the next 2 townhomes thru a party. I got drunk, woke up in my bed with a girl I only remember being introduced to sucking me off. We did the damn thing, showered and I walked her out. The door closing wakes up another girl who was asleep on my couch wearing only panties. She was still drunk enough to be escorted upstairs to my bed to do the damn thing again & again. That September 1994 weekend was everything. Shit was pretty vanilla until I moved to NJ and discovered Paterson in 2005

Hitchhiking home at Age 15 coming home from playing basketball (with a ball under my arm) in a Jersey Shore town in the late 70s. Got picked up by 2 older (18 maybe) girls who invited back to a party at their rental place. Crowded party with alcohol (obviously) and people snorting coke at the dining room table (new to me). After 2 beers and about 30 minutes I was in bed losing my virginity with 1 of the girls. The other girl was in the same bed at the same time with another dude. I left my basketball there that night and when I went back the next afternoon to get it, new tenants were in the house. Never heard or seen the girls again.

@EveHartley

If by "Holy Shit" sexual memory you mean Something you think when you experience a incredibly, surprising, amazing sexual event.

It has to be June of 2017 when I meet my ATF woman, it was a beautiful twenty something Russian blonde high end escort in Beverly Hills.

It was a great GFE, at a point when we change position and moved to doggie she laid face down on the bed with her feet on the floor.

The view was amazing, I couldn’t believe I was with this nice and beautiful girl whit a perfect body.

I went at it with all I have, her pussy was well lubricated and perfectly tightened, I was going in and out at a good pace, and going insane at the whole unbelievable sight and sensation.

After a few minutes she moved her right hand to push me back and my dick came out of her pussy at the same time she squirted, no like a stream, more like dumping a cup of liquid, got my feet really wet, I have never seen anything quite like it, not even in squirt porn.

She asked me how did you do that?, I did not answer, because I don't even know, I just went back in and gave her everything I had, I was sweating rivers myself, I had to get a towel to dry myself, and went back in with all my heart and soul, she dumped two mor cups of her pussy juice, and keep asking me how are you doing this? But I did not answer, because I don't know.

I have never been so turned on in my life, the girl was super beautiful, sexy, sweet, nice the closest feeling I can compare is the first time I saw naked pictures of Marilyn Monroe as a kid.

I stopped because I came, I was exhausted and she looked exhausted too but I was as happy as one can be.

It was one of the most incredible, surprising, amazing sexual experience I have had in my entire existence.

Thank you for making me remember and enjoy the memories.

This is the article I wrote about the entire event.

tuscl.net

I guess my first orgasm, which was self induced years before I was sexually active... I remember thinking, "oh, THIS is the spot I was supposed to hit all this time?!" It was a brand new discovery and I was like damn life is awesome!

Also, I guess the first time I tried anal?

@CJKent - I read your article, did she ever call you back? I suppose if she did you would've said so

@DeclineToState

To answer your question; I am sorry to say that she didn’t call me.

After a month, I sent her a text asking if she was in the States, she texted back saying:

“Hello Darling :) I am in London until the New Year”

After the new year se sent me a last text informing me she was sorry she was unable to come back to the USA.

"'tis better to have loved and lost than never to have loved at all"

~ Alfred Tennyson, 1st Baron Tennyson ~ Born: 6 August 1809, Somersby, Lincolnshire, England ~ Died: 6 October 1892 (aged 83) Lurgashall, Sussex, England

@Upright : Copycat.

@CJ : Ah, that reminds of the very first time I had a stripper squirt on me during a private dance. Totally unexpected, definitely one of my several 'Holy Shits'. I've got a written record of it here.

@Nina : I wish I could call my first anal a 'Holy Shit' experience in a good way, but that time and several other times I've attempted it, it's been more like "Holy Shit, why the fuck do people like this?". I don't knock anything until I try it, and I've tried many sizes, lubes, speeds, you name it. I can't get into it at all.

Other than the obvious first orgasm, first BJ, first real sex, etc. ...

I guess my "holy shit" moment was when I found out at a later stage in life that money can buy sex and not just a streetworker or at a brothel (which was my stereotype), but it buys sex with strippers in the club, outside the club and with escorts and SA girls. It's cost me a lot of money since I discovered this, but at least I have some amazingly good memories (and some horrible ones as well, truth be told).

I still need that "holy shit, she squirted" moment, that "holy shit" full sex in the car experience, that "holy shit" we did it in public sex, and that "holy shit, a threesome is awesome" moment, so plenty to still look forward to!

Was a virgin first time went into a stripclub. Met a dancer who was friendly and rather hands on. Told me she's like to do something more. I agreed. Pretty sure I said "holy shit" as I got my first BJ. Kept seeing the same dancer. Had a lot of firsts with her.

Sorry scat has never been my thing.

A then-girlfriend and I were getting heavy into some foreplay on her living room couch. Clothes coming off, the whole nine. She told me to lay down on the floor. Cool: I laid on my back because I'm always down for mouth and tongue action. I got mouth and tongue action, alright - but not until after she told me to turn over.

A lot of people (especially straight men) underestimate just how sensitive that spot is. :)

Probably the first time I figured out how to masturbate. Nobody taught me I had to figure it out on my own. The phrase "whack off" well I started out doing that but it didn't feel good. Then I started just squeezing it watching porn and then all of a sudden this goo came out and felt so damn good. I've been addicted since.

My first time at an fkk in Germany. I lost my mind seeing nearly a hundred European young girls strolling around naked ready to suck and fuck any man with 50 euros. Was apprehensive at first of having nothing but a towel to hide my boner. After a couple of drinks I am sitting at the bar and this gorgeous girl sits next to me and I just lean over and kiss her. We make out then she take off the towel and start blowing me. I then take her to the keno and we do it infront of everyone.

I was kind of a late bloomer and I recall a particular hand job in college. I was on a date with a hot, but very churchy gal at an amusement park. We were in the top of the Ferris wheel, sitting in place for a bit when she reached inside my shorts and jacked me off. That’s when I realized “holy shit, even churchy girls are down for fun”

My most memorable sexual "holy shit" moment was the first time I had sex without a condom. For three years, even when my first partner and I took each others virginity, I always wore a condom. A group of friends and I were watching Speed or Speed 2, but I was distracted by a new member of our group who was sitting next to me blatantly masturbating. We had been heavily flirting the entire time, so there was no misunderstanding her cues. She dragged me off to an empty corner of the theater, opened up my pants, and sat on my erection, no condom, and started bouncing and grinding. It was better than I imagined, I held out as long as I could before she made me cum in her pussy. She sat on me until I softened, got up and sucked me hard again, and the rode me cowgirl a second time and made me creampie her again! Our groups split up after the movie, I had to get home and clean up. I only saw her once after that, maybe three years later. We caught up a bit, but didn't reconnect. She was a nice girl, but prone to bad decisions (obviously).

I'm going to add a second story that was a "holy shit" realization several years after the act. As I wrote, my first was a virgin, but she had led me to believe that she was not. After our first time having sex she was bleeding, slightly, evidence on the condom. This occurred the second two times before it stopped. Many years later, I met my wife who was also a virgin. Breaking a hymen without condom is unlike anything else. The sensation is fan-fucking-tastic. I wanted to cum right then, but had to make sure her first time was all about her. There was a bit of blood after that, and the next few times after.

I literally saw the lightbulb explode over my head when I realized my first WAS a virgin, too! She had lied, and that bleeding was from her hymen. There's always a twinge of regret when I realize that my first time could have been on a whole other level.

my ‘holy shit’ moment was when a friends girl friend played with my dick. it wasn’t a bj or even a hand job... but OMG... it was nice.

@Jascoi: So what kind of job was it?

compared to a bj or hk it was really weak. but at the time it was over the top for me.

hk=hk.

damn seri. HJ.

@EveHartley

I am so sorry about your bad experiences with anal sex.

As long as commercial media is glamorizing anal sex without proper education, there will be plenty of confusion.

Despite the fact that there is a high concentration of nerve endings around and just inside the anus—so in theory the ass has the potential to be a stimulating erogenous zone—there's also plenty of room for error with anal play.

The majority of young women who had engaged in anal sex said the encounters were riddled with pressure and were often painful.

First things first, for anal sex:

“Doing things right” is probably more about technique, the thinking, and the emotional feelings that surround being penetrated anally and maybe penetrating as well.

For anal sex to be enjoyable, you have to get past the anus' biological purpose, and look at receiving anal as something pleasurable,

If you are with a partner, you both need to feel safe. That requires interest, curiosity, consent, condoms, and cleanliness.

Those are some easy ways to make anal easy, clean, and fun:

Bathe or shower together beforehand and wash the anal area with warm, soapy water.

Always use a condom and lots of anal lubricant on fingers, penis, or toys.

Start by stretching the anus with a small butt plug before inserting anything larger.

And increase the size of the butt plugs gradually, to a Medium, using plenty of lube, and to a Large, again plenty of lube.

Funally one large enough to match the size of the cock that is going to enter the back door.

The whole time, just breathe and relax, make sure you are having fun—it helps everything go a little smoother literally...

My very first trip to a club. :)

I was 17, and while I'd had sex before that, it was my first time with a pro who really knew what she was doing.

When i was in middle school i stumbled across my brothers porn magazine stash. I remember it was a foot or leg fetish magazine. In it the story that accompanied the photo spread was the model describing to the reader how to wrap her panties around your cock and stroke it. at the time i didn't know what masturbation was...needless to say that day changed my life forever.

My first time with a real squirter. I thought it was just when a woman got really wet. I was finger banging a girl and when she came I thought she was peeing on me! It was just spraying out. I needed a big towel to clean up after that.