The Craziest Night Of My Life

I’m the one on the right.

Prologue

As you read this story, keep the following in mind:

None of it would have happened, if it wasn’t for one key decision. When I was standing around at an after-party, the girl I had brought as a date, who is full of herself and disrespectful to most men, including me, decided to run off and say hi to a guy she recognized across the room. Instead of calmly inviting me to join her, she insulted my masculinity and ran away from me, leaving me standing alone awkwardly.

At that moment, I could have just waited there and sucked it up. But fuck that, I don’t let silly girls dictate my value based on their limited perception.

I walked out to the dance floor and approached a group of three blondes– two girls and a guy. They were shaking it and having an awesome, sexy time. In fact, my date and I had just been watching and talking about them.

I stopped in front of them, and all I said, with a playful smirk on my face, was:

You guys look like you’re having an awesome time.

The taller blonde girl pulled me in to join them and started grinding up on me, and when my date finally turned back around, her jaw almost hit the floor.

I smiled at her, and waved.

****

A Regular Night

Everything starts off normal. I get tickets to a concert through work, so I bring a hot girl who I’ve hung out with a couple times, but seem to have been friend-zoned by. I up the game tonight, but she has basically already ruled me out. At times I can feel her reacting to my dominance, but it is never enough to flip the switch.

On the bright side, she wants to go to a bisexual designer friend’s after-party at his clothing store, and I figure there will be plenty of talent there. It turns out I’m right.

We hang out for a while, and as described above, she is flakey and annoying, so I go off on my own and do plenty of mingling. I get a couple numbers on okay leads, and I also meet the above group of blondes.

After grinding with the tall blonde for a few, she says they are going to get more drinks. She leans in and gives me a very sensual kiss on the neck and then my cheek.

I like this chick’s style.

****

Things start to get interesting a few minutes later. I run into the tall blonde (Jess) again, and she tells me they are leaving to go back to their apartment and get in the jacuzzi. She says I’m welcome to come, and tells me the address. I’m still there with my date, so I am skeptical that this is really going to happen.

I finally leave with my date, and drop her off at her apartment nearby. She gives me a polite goodbye hug and bolts. Fuck. Aside from getting a couple of numbers at the party, I’m left bulbul bayad (a useful Hebrew phrase I learned in Israel, meaning “dick in hand”).

****

The Moment Of Truth

It’s 2 AM now, and I’m feeling pretty tired, but thoughts of a jacuzzi party are on my mind. The girls seemed really sexual and forward, so I feel like good things will happen if it actually goes down.

I could just show up there, since they told me the address, but I feel like that would be shady, and since it’s so far from where I live, I want to be sure I’m not wasting my time driving there in the middle of the night.

So I text Jess: “You guys heading to the jacuzzi now?”

No reply. I start driving home.

Then a couple minutes later: “Yep! Now!”

I turn the car around, and start heading toward them. But I’m still not convinced I’m in. To make absolutely sure, I text her again:

“What’s the address again?”

I know what it is, but I want my invitation to be rock solid.

Minutes go by as I continue driving toward them. A voice in my head is telling me I’m wasting my time and should go home to sleep, but I press on, imagining having to pass out under a dock on the beach, or in an alley somewhere.

Finally, my phone vibrates.

“(Address)… buzzer is (code). we are by the pool.”

I let out a little cheer in triumph, knowing the first hurdle has been overcome.

The jacuzzi party is happening.

****

A Fest Of Sausages?

My next concern is the sex ratio when I arrive. I can tell that this will be a slam dunk as long as I’m not the extra dude showing up.

When I finally get there, I’m greeted at the pool gate by Jess, completely naked, large natural tits on display, who kisses me as she lets me in. A polite, sensual kiss on the lips.

Very good sign.

Pretty much from this moment forward, I feel like I am being led through Willy Wonka’s factory on a magical journey. Almost every single second, I want to start giggling like a moron and screaming “I CAN’T BELIEVE THIS IS HAPPENING!!!” But I keep it together.

She leads me to the hot tub and tells me I have to get naked like everybody else. I count the two blonde girls with the blonde guy from before, a curvy asian chick, and a nerdy but muscular dark-haired guy who seems to be paired off with her.

I get in the hot tub, and Jess straddles me immediately, rubbing her great ass all over my cock. She truly has a stripper’s body. She also gets out of the jacuzzi to do yoga poses on the steps for all of us, completely spread-eagle.

Then, Jess switches back to the blonde guy, who I later find out is her boyfriend (Scott), and leads the petite blonde toward me by her hand. This is Ashley.

Ashley climbs right onto me; we wrap our arms around each other, and start making out. She is completely into it, and even though I had said only about one or two sentences to her earlier at the party (when she told me she is in town for two weeks from the midwest to do some modeling shoots), she is completely mine now, and will do anything and everything I tell her to the entire rest of the night. So yeah, I pretty much hit the lottery.

She strokes my cock and I start fingering her in the jacuzzi. The other two couples are also making out, and it has a pretty relaxed atmosphere.

Jess’ phone buzzes and she checks the text. It turns out there was another guy they invited who is on his way over. In my mind, I’m like fuck. Luckily, the other two dudes are totally in command of the situation, and veto it immediately. “We have to keep the numbers even,” they say.

Jess texts the guy to tell him the bad news. She then laughs and tells me, “If you had shown up 5 minutes later, you would’ve been the one getting turned away!”

We all laugh about it, and I say, “Well I guess I have good timing.” My internal monologue is saying something like, HOLY FUCKING SHIT I AM THE LUCKIEST MAN ON THE FACE OF THE FUCKING EARTH.

****

Things Go From Great To Better

The guys say it’s time to move upstairs and take a shower, since the hot tub is cooling off. I get out, and I’m fucking freezing. All my clothes are soaked. Ashley lets me share her towel, but we’re both shivering. I’m trying not to look like a total pussy, but yeah… my whole body is shaking from the cold. At least I have this girl’s nice ass and tits pressing up against me.

Jess says her apartment door is open, but we get upstairs to it, and it’s locked. Shit.

So there are six of us locked outside, naked. Luckily, her apartment has a window right next to the front door… over a ledge, but close enough that you can climb in. As long as you don’t fall down to your death. Thankfully, one of the other dudes (Scott, who lives there too), volunteers to climb in.

We move inside. The three girls get in the shower, and start acting out the best porno you’ve ever seen. I realize the other two dudes have bathing suits on, and I feel awkward about not knowing orgy protocol. I ask them if I should put some underwear on, since I’m just standing there naked, but they say they were only wearing bathing suits to walk upstairs.

The girls are soaping each other up, making out, sucking each others tits, spanking, rubbing each other’s pussies. The guys are just watching. Both the other guys leave the room at one point, and then, the girls invite me into the shower.

So I get in and join them, and suddenly I have three girls rubbing soap all over me and grabbing my cock, while I make out with Ashley and squeeze her tits.

Yeah, that happened. Fuck.

Soon the other guys join, and at this point I’m so happy, I don’t even give a shit that it’s kind of gay being crammed in a shower with two other dudes. In that moment, I’m starting to understand the whole free love and sharing thing. None of the guys touch each other at any point during the night, but we all respect each other and it seems like the dudes are genuinely happy for me that I’m enjoying myself. Cool, bro.

I definitely could not have handled myself properly in this situation had I not banged many girls and gotten completely comfortable with sex before. Also, changing at my gym locker room over the last year has gotten me over the weirdness of being naked in front of other people. I can just go with it.

Also, while I was going through this whole experience, Tyler Durden’s Secret Society post kept popping into my mind. I think having read that article a while ago helped me out in this situation. I felt like I sort of knew how to behave, i.e. not making anyone feel any negative emotions at any time, and that kind of thing.

****

Phase Two

After we’re all “clean” we get out of the shower and begin the coconut oil massage phase. Yes, apparently that is a thing.

We all lay on the king size bed in different combinations, and before I know it, I’m laying on my back with Jess straddling my cock and massaging me, while the Asian girl massages her, and the Asian girl’s boyfriend massages the Asian girl. So all these different people’s movements are pushing Jess into me, rubbing against my hard cock while she massages my chest with the warm coconut oil, and I squeeze her tits.

I notice Scott massaging “my” blonde girl and making out with her next to us. I feel a little pang of jealousy, but realize that I cannot entertain any thought like that here. He’s the host and I’m basically here on his terms, and I also think they are all trying to exist in a judgment-free space of only positive emotions. Plus I am squeezing his girlfriend’s tits right in front of him, so I guess it all evens out.

Before I know it, people are in a daisy chain of oral and manual sex. It’s a twisted wild human centipede. Someone is eating a girl’s pussy while she jerks a guy off. A dude is fingering a chick while she sucks my dick. Etc. Etc. Again, the entire time I want to start laughing and yell “I CAN’T BELIEVE THIS IS HAPPENING!!!”

But I keep my cool and don’t blow up my spot.

****

Let’s Start Fucking Already

The host couple starts banging with a vibrating cock ring. My girl then asks me to fuck her with the vibrating cock ring, since she’s never done that.

So after a quick rinse, I put on a condom and Scott’s vibrating cock ring. I fuck her with that for a while, on a separate couch. (Earlier I had heard the hosts casually discuss laying a sheet over this couch, since people were probably going to fuck on it. I had known I was in a great situation at that point, since “people” was pretty much just me.)

We pause to take a break (and I wanted to postpone my orgasm), and the nerdy dude takes her onto the bed and starts spanking her a lot. Jess is now wearing a sexy leather outfit and is hitting Scott in the ass with a flogger. He screams loudly and runs away from her, which scares the hell out of me. Jess comes after me next and I resist, saying “no ass flogging for me.” She makes me let her do it, and starts very gently. When she gets up to speed, I realize its not actually bad. “I have an ass of steel,” I remark.

So nerdy dude is just about done turning my girl’s ass cheeks red, so I take over, and start fucking her on the bed (missionary with her head hanging off the side). I fuck her hard while everyone watches. Having an audience makes me focus more on my thrusting technique, and Ashley loves it. I even get to hear the Asian girl’s commentary lying right next to us on the bed: “Oh my god she really likes it… look at her toes curling… and there go her fingernails…. oh wow, im jealous, she is having fun…”

Since I drank and am wearing a condom, I eventually go soft. In my mind I wonder if it’s going to be weird having performance issues in front of an audience, but I don’t make a big deal of it. I make one remark about alcohol and condoms, and they all agree that condoms suck, and offer support. Ashley strokes me back to hardness while I stare at Jess’ body in her leather outfit. Then I flip Ashley over and fuck her doggy style.

I’m going really hard again, and Jess comes over and starts flogging my ass while I’m banging Ashley doggy style. I let her continue; it’s kind of nice having more participation.

I have a great orgasm, while fucking a hot blonde stranger doggy style, getting my ass whipped by a stripper-looking blonde chick in a leather bondage outfit, with a sexy Asian girl lying next to me cheering me on. Surreal experience.

Right after I finish, everyone gives positive comments about how the two of us were going at it. The Asian girl says I came “like a boss” and then gives me a hug.

****

Afterglow

I clean up, and we are all just chilling out. Everyone is acting pretty normal. The two couples start talking about seeing each other at the last LA swingers event. They do this often, apparently.

They also fill me in on how they met Ashley earlier that day at bar before the after-party we were all at. Apparently Scott saw her across the room and knew she was Jess’ type, so he brought her over as a “gift.” It seems there was instant chemistry, and the girls recognized each other as kinky kindred spirits.

Before I leave, they invite me to the Bondage Ball in July, but unfortunately I’ll be out of town that week. We exchange numbers (and later Scott and Jess look me up on Facebook), and I also find out that Ashley is staying close to where I live. So we decide we’ll hang again before she leaves town in two weeks.

****

And that concludes the story of my first group sex experience. A night that I will never forget, but can strive to replicate again. It was an extremely positive experience; even though at times I was waiting for the other shoe to drop, and some Eyes Wide Shut cult members to suddenly emerge and murder me, it ended up that I was just in the company of some adventurous, generous, fun-loving free-spirited people.

As we said our goodbyes, I saw that it was customary for the dudes to give each other a nice hug. I guess once you’ve had a girl jerk you off at the same time as another dude, and then he watched you cum while his girlfriend flogged your ass, you’re familiar enough to hug it out.

It was a night of approaching and then crossing boundaries, and leaving them completely behind. To go to extreme places, you have to make some compromises and sacrifices, and completely let go of your inhibitions.

In a sense, the sex was so normal and easy that it changed my perspective. It showed me what the world looks like for people who just assume sex is abundant and welcomed by all. It reminded me how important it is for girls to feel safe and comfortable, and know that you’re just cool and stable and can have a good time. On this night I was just completely easygoing, cool, and relaxed with them. If you keep that up, just being natural, girls will continue to gravitate toward you.

So now we’ll see what the future holds. I hope sex is still interesting one-on-one, because I can tell you that group sex is pretty much awesome. I actually liked that after I finished, I had some dudes to talk to and joke around with, instead of having to just have a post-sex conversation with one girl I’m stuck with. The whole experience was completely positive from start to end. I fucking loved it, and I feel blessed to have had it.

And for the record, if any of you guys are wondering/concerned about being in this situation, I did have the smallest dick of the three guys, but not by that much. Honestly, I don’t really give a shit. If you’re not living on the African savannah fucking girls raw dog right after another dude, penis size is mostly irrelevant. I just owned it, didn’t comment on it, didn’t think about it, and everything worked out fine.

****

On a final note, it’s been my policy to withhold the stories of girls I’ve slept with, since I’ll be publishing the first 25 in my upcoming book, The Quest For 50: Volume 1. But after tweeting about this experience and seeing the fervor people had to know more about it, I decided to share it with all of you immediately.

I hope you enjoyed the story, and look out for my book soon.

  1. Very interesting perspective on the whole thing.

    I think that the experience for you was very eye opening but in my thoughts it transforms ones view more to a social rather than an individualistic sort of thing where by everyone really did have fun and you feel not only good but great to be accepted by other people.

    The problem from my perspective is that there are always trade offs. Nature makes us greedy, jealous, and individualistic for lots of reasons some good some bad but that’s what it is. Loosing some of this perspective and gaining some other broadens the acuteness of how you perceive the world in one way or another in a sense. Anyways good for you dude.

  2. Wow! Thank you for sharing that experience and giving us a glimpse of something that most would otherwise never know about. I disagree with it coming about as the result of just one decision though. IMO it is the reward karma, the universe or whatever, has given you for taking the “red pill.” You have done the work internally and externally to prepare you for it. Enjoy…

  3. Jack

    Cool.

    I think most average guy’s first reaction to an orgy is “okay as long as I don’t have to do gay shit” Sounds like that’s either not an issue with the orgy crowd, or you just lucked out. I don’t know. That whole scene is sketchy to me, probably the only way I’d get involved in an orgy is the way you describe.

  4. Senior Beta

    Now that’s a story. Well done.

  5. jon

    Was the tall blonde taller than you? I’m on the short side (5’6”) and my game is weak, I think I would have blown it.

    • Author Dagonet

      I think she is about 5’9 or 5’10 (if you don’t count the heels she was wearing). But I wouldn’t discount yourself when a girl is taller than you. That would be like me saying “I had the smallest dick there, so I should have just left before I embarrassed myself.”

      If you’re confident and congruent, owning who you are, then these things are trivial, and won’t stop girls from wanting to fuck you.

      • jon

        Unfortunately, dick size only matters after you have already sealed the deal. Its not really comparable to height, which is readily visible for all to see, and easy to judge upon. Getting beautiful girls is much harder when you are short. Not impossible, just harder.

  6. I don’t know what to say this.

    Congratulations, you have graduated into the secret society.

    Inspiring.

  7. FFY

    Dayamn.

    Respeck.

  8. Phoenix

    After reading this I felt a surge of confidence in my existence.

    Have you considered telling this event to the girl you dropped off beforehand? Maybe it’ll spike her interest in getting involved in a possible future orgy!

    • Author Dagonet

      Haha, good idea. I’ll fill her in on what she missed.

      • Phoenix

        You know how to play it, right?

        Not as a big deal – just an exciting night. Then say “You gotta meet this girl, she’s really cool when you get to know her”.

        Ashley comes out – talk positively about her. Throw a positive comment about the hot babe that FZ you. Act natural … play a game or two of darts and bet drinks. Flirt with both.

        Get them to like each other. Touch them both. Invite back to your place for champagne.

        You start making out with Ashley. Then Ashley makes out with hot girl. Then you start making out with hot girl. They should know it’s on.

        And I tell you what – if hot girl isn’t feeling the vibe enough yet, then fuck it. She can watch you two go at it. (And I’ll bet you $10,000 that she’ll get so wet that she can’t resist joining in)

        There’s your next fantasy, bro! Make it happen!

  9. Doug11111

    Great stuff. Very hot read. Great group of people you ran into.

    How would you rate Jess and Ashley on the HB scale?

    How did you like the vibrating cock ring?

    • Author Dagonet

      With clothes on, I would’ve put Ashley at an 8 and Jess at a 7. But once they were naked, I realized Jess had a ridulous body, and I’d say they are both 8s.

      The cock ring was fine… didn’t really affect my enjoyment much, though she seemed to like it.

      • Doug1111

        Thanks.

  10. Doug1111

    Jack–

    Sounds like that’s either not an issue with the orgy crowd, or you just lucked out. I don’t know. That whole scene is sketchy to me, probably the only way I’d get involved in an orgy is the way you describe.

    There was very little or no AMOGing going on in this circle of swinging friends and new friends, which is by no means always or usually the case. Also Jess seems to have been the leader really, which may have effected that dynamic.

    • Author Dagonet

      Yes, that’s a good observation. Jess was really the boss, and Scott was just really relaxed and having a good time doing what they do.

  11. adsaf

    where did you cum on her? whats the orgy etiquette on this?

  12. Pingback: Orgy Blonde Part II | The Quest For 50

  13. Pingback: Linkage Is Good For You: 7.1.12 | Society of Amateur Gentlemen

  14. AJ

    Dude!!

    First thanks for writing it up, this must have taken a couple of hours at least. And it was a great read, a lil jealous but it means I ain’t putting the hours in like I use too.

    Second, just well done, you read the situation well, you managed it well, and that starting from a date with a hater. Kudos.

    You must be so psyched, great feeling!

  15. Pingback: New interview series: 20 minutes with Dagonet « rivsdiary

Leave a Reply

Your email address will not be published. Required fields are marked *

You may use these HTML tags and attributes: <a href="" title=""> <abbr title=""> <acronym title=""> <b> <blockquote cite=""> <cite> <code> <del datetime=""> <em> <i> <q cite=""> <strike> <strong>