Stuart and the Sex Party

New York City, Summer 2015

Stuart and I had fallen in love in high school in the middle of America.  We were each other’s firsts for everything and explored each other’s bodies every chance we got--in moonlit parking lots, hidden corners of the school auditorium, stolen moments in a friend’s basement.  I was a year older than Stuart and had to put our relationship on hold when I left home and moved to New York City for college at 18 years of age.  Stuart and I stayed in touch, doing our best to maintain what we used to have over text and phone calls.

A year after I arrived in New York City, Stuart came for his first visit.  I drooled over this boy, tall and slender, dark chocolate hair that fell effortlessly, and green eyes that lit up when he smiled.  I was a tad taller, with lighter hair that I never gave much thought to.  He was an artist and, I an academic, but we were a good match for young love.

As young gay men from the midwest, New York City was a whole different world, and for Stuart’s first visit to see me I had planned a real treat.  Earlier that summer, holding my breath while handing a bouncer my fake ID, an older man grabbed my ID and scrutinized it, and then me.  It was clear to anyone that I wasn’t 21, and that is exactly what interested this older man.  He waved away the bouncer and guided me in, chatting with me, telling me about the fabulous parties he hosted for the prettiest young twinks.  He took my number and promised he’d invite me to his next event.

Soon enough I got a text with details for an “underwear party.”  A first for me, I didn’t even realize such a thing actually happened.  This man had arranged for a penthouse apartment in Chelsea for the night, open to gorgeous young men to lounge about in their underwear or even less.  It just so happened to line up perfectly with Stuart’s visit.  I sent this man a picture of my boyfriend asking if he could be included, and the man became even more eager to have us there.

Stuart and I wore matching underwear for the event--his, a bright blue Andrew Christian brief and mine a bright coral.  We walked to the party, nervous for our first experience with something like this.  Arriving at the apartment we were greeted by a twink a little older than us, handing us bags and markers for our clothes.  We stripped quickly, a little shy and chilly.  The older man found us quickly and gave us a tour.

The penthouse was magnificent.  It was three successive floors, each smaller than the last but replacing the lost indoor space with two levels of outdoor terraces.  The walls were largely windows peeking out to the summer night over the city.  There was soft candle lighting warming up the image of plenty of men already stripped to their underwear and mingling.  Stuart and I joined the party, chatting with strangers, smiling sheepishly as we explained that yes, we were only 18 and 19 in this room full of late 20-somethings.

The alcohol was flowing but Stuart didn’t want me to have any--he hadn’t really started drinking yet.  The alcohol would’ve helped my nerves as I explored the second floor nervously.  Here were two bedrooms and a massive bathroom with a tub fully in the center.  Two men were sitting on the edge of the tub laughing and dipping their toes in warm soapy water that was flowing out.  Stuart and I joined them, slipping into the conversation quickly.  I lost interest and wanted to check out the other room, connected to the bathroom by a massive closet.  I stepped into a darker bedroom, sneaking peeks at men paired off in the shadows kissing and fondling each other.  I lingered, enjoying the view, before making my way back to the bathroom.

My eyes shot straight to what should have been an expected sight.  My eyes traced the bulge of Stuart’s blue briefs, up the soft, tanned skin of his stomach, the subtle curve of his collar bone lit by the candles in the room, until I saw his lips pressed against another man’s.  This man’s hand is on my boyfriend’s cheek, pulling him closer, to touch more while their tongues explored each other.  I let this continue for another minute, jealousy pooling in my stomach.  Stuart and I hadn’t discussed this real possibility, and I became quickly territorial, clearing my throat to catch Stuart’s eyes and giving him a meaningful look.  I spun and left the bathroom, waiting in the dark hallway for him to join me.

He left me waiting at least two minutes.  That bastard.  Finishing up what he started I guess.

Two minutes felt like an hour as my frustration mounted.  Looking down at my own bare skin in the half light, feeling suddenly vulnerable.  Stuart finally appeared.  He knew, of course, how I was feeling.  We both knew I was the jealous type.  He interlaced our fingers and brought his lips to mine.  His soft kiss, I could never get enough.  I tried to forget that another man’s tongue had just invaded my Stuart’s mouth.  

Stuart pushed me against the wall while holding our chests close, skin to skin, warm and silky.  He wanted to make it up to me.  I saw it in his eyes and he slowly sunk to his knees, the two of us finding a moment of peace while pairs or trios of men slid by, some pausing for the show.

Stuart traced my sides with his finger tips, and pressed his cheek to the side of my bulge, sighing deeply.  He looked up and locked eyes with me as he pulled the sides of my briefs down and released my cock.  I was slowly getting hard, pushing away any feelings other than lust for this beautiful boy at my feet.  He gently wrapped his hand around the base of my cock and I gasped quietly at this first touch.  He pulled smoothly, the perfect amount of pressure to really get my dick rock hard and ready for him.  He gave the head of my 7” dick a kiss and slowly let his lips wrap around it.  The warmth of his mouth was so welcome after the breeze flowing through the penthouse.  Stuart went down as far as he could on my dick, maybe about three-fourths of the way.  Pressing his tongue along the length of my dick before slowly pulling back.  He picked up speed, bobbing back and forth while I breathed deeply and arched my dick further into his mouth.

A man observing us gave an appreciative sound, encouraging Stuart and I both.  I pulled Stuart up and led him into the nearby bedroom.  More couples had paired off and were recreating Stuart and I’s show.  I pushed Stuart’s back towards a wall and knelt before him in return.  I spun him around and quickly pulled his coral briefs over his ass, slightly hairy and noticeably paler than the rest of his tanned skin. I took a deep breath as I started to savor licking and biting around his ass, taking my time as I narrowed in on his crack.  I’m a firm believer that the first touch is most sensitive, and was careful to take advantage of every new inch of his ass as I explored.  I pulled his ass cheeks apart with my fingers, finally getting a view of his hole surrounded by a ring of fine hair.  I dove right in, one long lick pressing my tongue flat against his hole.  I swept my tongue across his ring a few more times before starting to spear inside and really slobber on the edges of his sphincter.  God, I loved eating his ass.  That boy could’ve suffocated me with his ass and I would’ve died happy.  

My cock took over and I rose up, pressing my back to his chest, letting my dick fall into place in his crack.  I reached around and palmed his stomach with one arm and gently held his neck with the other as I licked his neck, enjoying every deep sigh I was pulling from him.  He twisted roughly to finally kiss me again, fed up with pent up arousal before dropping to his knees and swallowing me once more.  Those around us had been busy while I was rimming Stuart, with couplings claiming precious space on the bed.

I saw couples grinding on top of one another, underwear lost in the fray.  A cute young guy laying back on the edge of the bed was suddenly hoisted up by a hunky man to rest his legs around his waist and ass on his crotch.  A familiar face from earlier was devouring a thick cock just feet away from Stuart and I while another man loosened our new acquaintance up with two fingers.

I spotted an opening on the bed and lifted Stuart up again and prodded him to the edge of the bed to lay down.  His ass, now elevated, was the perfect height for me to dive in with my mouth.  I was soaking up all this intense, sexual energy being so close to these other pairings, in different stages of kissing, sucking, and fingering.  Stuart writhed first with his head in the bed, but leaned up to watch.  I refocused on the privilege I had of excavating Stuart with my tongue, finally glancing up to catch Stuart kissing one half of another pairing on the bed.  

Jealousy is a bitch, and I immediately got up and flipped Stuart back over and fell on top of him.  This boy was mine, and I wasn’t going to share him.  I pressed my head in close to his, staring intently as I growled that only I was going to fuck him.  Stuart wasted no time grabbing a pump of lube conveniently left on the bedside table.  While his hand slicked up my rock hard cock, I saw the pairing next to us similarly ready to start fucking.  I overheard the bottom begging the top to put his cock in.  Just past them, the muscle man was fully buried inside his chosen partner, whose head lolled back in enjoyment.  At least three couples were about to fuck on this bed, with others surely balls deep in each other just out of my view.

Stuart had my cock ready, and plunged his own lubed up finger into his spit slicked hole.  He lined me up and pulled me in for a deep kiss as I pushed inside him.  I was fighting back jealousy, my hormones were in overdrive, and I had something to prove, so I won’t pretend I gave him time to adjust.  Fortunately, Stuart was just as overcome by the orgy around us and his ass opened up beautifully to me.

Stuart’s ass.  It really was a gift.  Even now, six years later, I get hard thinking about it.  If I thought his mouth was warm, then his ass was a furnace.  Velvety smooth, rippling around my dick as I started hammering in and out.  Stuart’s groans joined the chorus around us, overpowering the sounds of my deep gasps for breath.  

After so much buildup, with this much tension in the air, this wasn’t going to be a long fuck, just a deep one as I bottomed out into Stuart and then shoved a little harder for good measure.  We were wrapped up with one another when the old man host of the party appeared next to us.  I saw the lust in his eyes as he watched, and I’ll admit, the feeling of objectification was exciting.  

My knees were locked underneath Stuart’s legs, hoisting them up to the best angle for my strokes.  His 7.5” dick was fully erect, fully appreciating the feelings of pleasure reverberating from our fuck.  Strings of pearly precum were falling onto his tanned stomach.  The host saw his opening.  As the intensity of our fucking built, the host grabbed a pump of lube and kneeled down with his eye on the prize.  

He grabbed Stuart’s dick in between our two sweaty bodies, slicking it up and moving in motion with my own strokes.  Stuart threw his head back and groaned in appreciation, his dick finally getting the attention it needed.  That brew of feelings inside swirled, the arousal of being watched, anger at this man touching my boyfriend, subtle shame that my boyfriend clearly loved it, excitement at the orgy around us, the pleasure of Stuart’s ass cannel squeezing my cock, all collided and pushed me past the point of no return.

With a heavy groan I slammed into Stuart one last time.

It’s necessary to use metaphor to embellish a story like this, but I promise you the feeling can quite literally be described as if fire burst out of my dick.  An absolute geyser of pleasure flew out of me, creaming the walls of Stuart’s hole, leaving me pulsing after at least 6 waves.  

Meanwhile the host’s hands flew, adding more pressure at just the right moment, bringing Stuart to his own ejaculation.  I watched Stuart’s face twist up while his body went rigid, finally blowing his thick load all the way to his chin, and dousing the grateful host’s hand in the line of fire.

The host pulled away, taking a quick taste of my boyfriend’s cum.  I glared at him point blank, giving him the clear message that he needed to fuck off now.

I gently lowered myself down onto Stuart, reveling in the feeling of his sticky cum between our chests.  I let our heart beats slow as I kissed him softly.  My focus narrowed so much during our fuck, but I now started to notice the other couplings around us, each building up to the same ending.  

After a tender moment, I pulled Stuart to his feet for the difficult task of finding our underwear amidst this mass of writhing bodies.  For our first sex party, it really went beyond all expectations.