In March, I went to my first ‘official’ orgy. That is, one that was set and planned to be an orgy, not a situation that just happened to turn into one. Its a night that I remember best in flashes of moments.

I spent the day before my first orgy doing what any girl would - trying to figure out what to wear. Because that’s the biggest feature of an orgy, of course. What you wear walking in the door. That, and the salad bar. I spent nearly two hours running in and out of Daniel’s room waiting for the ‘Daaaamn!’.

Sadly, Daniel was no longer going to the orgy, as three days before hand, he and Dianna decided to be exclusive. So sad. I had wanted Daniel/Jefferson D.P.

I finally settled on basic black underwear, and a one piece outfit of Capri pants and a tube top. I figured the answer to what to wear to an orgy is a simple ‘Easy on, easy off, and easy to find”. I made a few preparations before I left that turned out to be well though out. I had already called in to work. (No way was I gonna get all the way out to Long Island for a crappy part time job after an orgy!). I closed the blinds, turned down my bed, and set it up the way I like. Then I did my hair and make up all nice, packed up a few toys and my wine, and went on my merry way, arriving 8 pm on the dot.

One of my biggest worries about the orgy was shallow, but probably fairly common. I was afraid I would be the only big girl there, in a sea of hot skinny chicks. That would not have been good for my ego, or libido. (I like thick girls! I need some ass on my ladies. ^_^ ) I was so happy to walk in the door, and see other big girls! That was what really relaxed me the most. The fact that I immediately started in on my wine probably helped a bit. Everyone there was very awesome. The fact that they were all people I enjoyed conversing and drinking with helped a lot. Who wants to have sex with people they don’t like?

There was one very awesome moment before everyone got naked. A couple walked in the door, and I looked at the boy. I totally knew him already!

“You! I know you! Your ______ from OKCupid!”

“You’re ___!” Nearly a year previously, I had been messaging back and forth with him, and while we got along, nothing really came of it. He lived in Brooklyn, I lived in Nassau County. I had no desire to travel that far, and I doubt he did either. But how funny to run into someone you already sort of knew at an orgy?

I was tipsy enough at this point of the evening to share my favourite party trick. I can guess, by feel, a women’s bra size both cup and band, usually within two inches of the band. Carlotta, OKC boy’s girlfriend, had just gotten fitted for a bra, so she was the perfect test case. I performed admirably, and had more wine. At this point, I was pleasantly suffused with wine, was quite probably red faced, loose and happy, loud of laugh and loose of tongue. When a bowl was passed, I took a few hits, and soon enough, I was beautifully mellow.

The naked part of the orgy was rather slow to start, but soon Jefferson came out to announce they were having a screening of the Bi Apple. Everyone piled into the main bedroom, and sat down to watch. I was sitting next to Emily and in front of Lily.

As the movie progressed, the clothes started to come off. I know I shed my outfit and tossed it in the corner pretty quickly.

Now, I finally felt I was in my element (being naked with good people!). I looked around, and saw all these beautiful women around me. Naked. I swear, in my head, I turned into a fourteen year old boy. “OMG! Naked ladies! That its perfectly acceptable to touch! Boobies! Whee!”

At some point, I started making out with Emma before sliding down to the floor to eat her pussy. Someone, I don’t know who, was playing with me while I was working on her. After she came, she pushed me back down on to the floor, and started in on me. She was the first girl to eat me out. (Yes. I had managed to sleep with six women without really being reciprocated. Such is life.) A boy came over to us, stroking his cock over me before sliding it into my mouth. Things start to get a bit fuzzy at this point. I know that nice young man who had his dick in my mouth and I fucked on a chair. I recall pulling a classic porn star move with Emma, sliding underneath her and eating her pussy while her boyfriend fucked her. (That move, by the way, looks very sexy on film. In reality, when people are actually fucking in real life, it takes a lot of coordination to be able to breath. Not knockin‘ it. It was fucking hot. Just saying.)

After that, I took a bit of a breather. Still in the bedroom, I over heard Calico talking about a website she modeled for. The same website Princess Donna works for! Amazingly, there was another ‘we sort of know each other moment’ at the same orgy. Millicent, Princess Donna’s ex, got a kick out of this story. My world has been growing progressively smaller.

Aside:
When I was a little pre-pervert, growing up on Long Island, it was Millicent,a library coworker turned friend and her girlfriend Princess Donna, who helped shape my formative years. They took me to my first strip club, on my 18th birthday, to see Jenna Jameson dance, and to my first real porn shop, to rent bisexual porn. They showed me my first Leather Daddy video, and Bend Over Boyfriend. They bought my my first riding crop. They taught me what fisting was, and about Toys in Babeland, the wonders of lube, Tristian Taromino and her Ultimate Guides to Anal Sex for Women, the difference between a dyke and a lesbian, that sexual orientation was fluid, about Drag Kings and packing and that I kinda dig FTM trannies, that trying to take naked pictures in the supermarket is a fun and exciting way to spend a Tuesday night in the summer, and all sorts of other wonderful things. Some people are raised by wolves. I was raised by dykes. I firmly believe that if it were not for these two ladies, I wouldn’t be the woman I am today.

Calico is one of the most beautiful women I’ve had the fortune to meet. When I first saw her at the party, I did a double take. She looked like a grown up version of the first girl I ever kissed, during a game of strip Monopoly in high school.

Aside:
I had such a crush on that girl, but alas, it never really materialized. Though, I think she was curious herself. She twice asked me to have a three way with different boys she was dating. I turned them both down. The first one, because I just wasn’t all that into the gentleman in question, though we were friends and had fooled around a bit, and the second one, because it was Coconuts. I’ve known Coconuts since we were four years old. It would just be too weird if we ever had sex. Or even got kind of naked in the same room. Or. Anything really. To be honest, I really didn’t want to share her either. I wanted her all to myself, if only for a little bit.

The memory of my first girl crush combined with the beauty of Calico, really turned me on. I ate her pussy like a woman starved.

Goddamn that was fun.

Now, we come to the two moments of my first orgy that rocked my world.

The first:

After I finished playing with Calico, Jefferson and I started fucking on the bed, next to a few other people. By this point in the night, my head was in an absolutely amazing place. Every thing he was doing to me was sharp, clear and intense, yet everyone and everything else started to fade into the background. I was completely and utterly in tune with myself, the sensations rolling through my body, any inhibitions I had left blowing away in the storm rolling through me, in a way I have rarely ever experienced before in my life. When Jefferson slid out of me, and started fingering me…my god. That. Was. It. I was gone gone gone, pushed over an edge I didn’t even know was there. I had the most intense, rolling, orgasm, screaming, literally screaming, at the top of my lungs. Jefferson, that bastard, kept on going, more and more, and the waves kept rolling over me. When he finally stopped, the aftershocks rushing through me, I was a dizzy, shuddering, fully satiated, content Wendy.

Jefferson officially blew my top five orgasms (I keep a mental list of the top five) out of the water, out to sea, and took over all five spots.

The second mind blowing moment involved the lovely Sebastian.

When I saw Sebastian walking around the apartment, I was blown away. I have never met a man who was more my ‘type’. Tall, skinny, long curly hair, beautiful. Beautiful. He was walking around topless, with these snug jeans and a big belt buckle. Fuck man, if he had had a cowboy hat, I would have been done for. I nearly was done in, when I found out he loved ass play.

To this day, I don’t remember how it came up. I remember sucking him off in the crowded bedroom, exclaiming in delight over his cock, and the next thing I know, we’re both running for our strap ons, comparing dicks. Mine was deemed too small (!!), but I managed to fit his dick into my harness, while he was getting things together. (I now have a much much bigger dick. So big, *I* can’t take it. Yeah. That big.)

I waited for him in the back bedroom, sitting there with this amazing cock on me, more excited than anything. There is nothing, and I mean NOTHING I love more then fucking a man in the ass. To meet a man who’s actually willing, and not just willing, but eager for me to fuck his ass? All I could think was ‘What did I do lately to deserve this?’ I think it must have been karma from the shitty break up. The gods work in funny ways sometimes. “Well, she was just dumped and had her heart stomped on, but she took it well….let’s send her a beautiful ass-loving size queen! She’ll like that!” (Thanks guys! I do!)

Sebastian came back with a black glove, lube and a little bottle. He settled back on the bed, and handed me the glove.

“I want you to finger me first” Quite possibly, the hottest thing a man could ever say to me. Ever. (Keep that in mind boys.) He lay back, knees bent, legs spread, his hair fanning around his face, the tea lights flickering the backround…my god, I get tingles just thinking about it. So beautiful. So hot.

I slid up closer, my legs under his knees. I stroked the dick I was wearing, while he fumbled with the lube, squeezing it out on my fingers.

I started gently, probing with my index finger, before pushing it the rest of the way in. I savoured the feel of his warm, tight ass around my finger. I could feel my self getting wetter, juices starting to flow down my thighs. He asked for deeper, and then for another finger.

“Anything you want baby. As much as you want. You just say what and when, and you’ll have it.” He was breathing heavy, the sort of deep breathing you only get from an assfucking.

“Move them, just a bit. Just like that…” So tight, so warm…after a few moments, he asked for more. The third finger went in with just a bit of tension. I bent over, sucking his dick while working my third finger in. I couldn’t stay that way for long and continue finger fucking him, but when I eased back, fucking him in earnest, he started stroking himself.

(I’m so terrible, I know, at recalling what was said, aside from ‘more’ ‘harder’ ‘oh god’ and ‘fuck that ass’. But in my defence, all the blood had flowed out of my head, down to my pussy. I’m such a man sometimes.)

He reached for the small bottle, and when he opened it, there was such a terrible odour, and he inhaled from the bottle.

“Do you want some poppers?” Aaaah, so these were poppers. I’d never come across them in person.

“No, I’m good.” My god, I was more than good. I felt his ass tense, then relax around my fingers, and slid one more in, four fingers working his ass, his legs on my shoulders at this point.

All I kept thinking was “Oh my god. I’ve got on a black latex glove, and I have four fingers in this beautiful man’s ass, he’s doing poppers, and I’ve got this giant erection strapped on. I feel like such a fag! This is the hottest thing I’ve ever done! My god, I’m so turned on right now.”
I truly was. I can’t really explain what it does to me, fucking a man, but I was soaked behind the strap on, my mind totally blank but for the task at hand (Hur hur, no pun intended)
When he came, I damn near saw stars. Watching my fingers work his asshole while he stroked his cock, the both of us keeping up a flow of dirty talk in low voices…I was gone.

After easing out and getting the glove off, and cleaning up some, I curled up next to him, stroking his hair back and kissing him, telling Sebastian, who’s name I couldn’t even recall at the time, how well he did, how beautiful he was. Eventually, he had to go clean up a bit.

Everyone was back lounging in the main bedroom chatting naked, chilling out. Sebastian and I both wound up back there, sitting on the bed. I sat near him, stroking his back and arms, kissing down his wrist.

“Woah. What did I do to deserve all this attention?”

“You let me fuck your ass, baby.”

“Wow. You really like it that much?” He had an interested gleam in his eyes.

“You have no idea!” I forget, sometimes, that not all women love fucking a man’s ass the way I do. To me, its…trancendent, almost. Intense. I mean, I like getting fucked in the ass myself. I like it a lot. I fuck a man with everything I have. I just…I can’t get over it. I could wax poetic about anal sex for hours, but I just can’t describe it properly, especially not right now, all hot and bothered thinking about it. We mentioned getting together outside the party, but in this instance, did not get around to exchanging info. But that wasn’t the last I saw of Sebastian.

And thus, I ended my first orgy.