Ladies Night at the Leather Bar Ch. 01

Chloe McGill never led me astray. I was a full time, tax paying citizen of 'Astrayville' long before I met her - I just wasn't that good at it. Then Chloe came along, and that girl would end up getting me into some of the most outrageous adventures. I adore her. It must be made clear how much more she is than just a cohort in gang bangs and sexual trysts of all sorts and sizes.

She is the most influential person in my life after my parents. She found me as an insecure fledgling bisexual crossdresser, wobbly in three inch heels, with bad wigs and makeup, and turned me into a (mostly) confident girl out to take the world on my terms, striding through life in six inch stilettos. She was my Henry Higgins, and I was her Eliza Doolittle. She was my Sidney Poitier, who took me from crayons to perfume. To her, with love.

Me? I was her wing man (girl?), proud and grateful.

I met her at the West Hollywood Pride Parade in 2009. Even after the parade was over and the streetlights illuminated the advancing night, the crowd was heavy, with all manner of homos milling about, the sexuality thick in the air.

A band played in a parking lot and I headed there. I was supposed to meet up with a friend by the bandstand, so I waded in, trying to move forward. The closer I got, the denser the crowd became, until I found myself just another sardine in the rainbow tin of the moment.

Wedged in, I looked for a way out, but fate had brought me to this spot, at this exact minute in time for a reason, and there she was. I found myself shoulder to shoulder with this stunning redhead. She wasn't really watching the band, she was grinding against a guy directly behind her. With almost no space between us, I looked down her body and saw that her skirt was flipped up in the back. The guy behind her was fucking her right there!

I looked at her closely. I've always thought my gaydar for trannies and crossdressers was fairly good, but I was in awe. She looked like a real girl. It was only the circumstances that caused me to think that she wasn't. After all, why would a straight couple wriggle themselves into a mob full of gay people and fuck? Some new kink, maybe. I looked hard but could not see the boy in her (no pun intended).

Her face contorted in lust, I could see, but not hear her moans over the music. Then she turned her head. That was it. That was the moment I met Chloe McGill. She looked into my eyes through her 'I've got a big fat dick in my ass' facial expression, and focused on me. Clearly taken out of her butt-fucking for a moment, she smiled at me like a long lost friend. It was obvious to both of us that we were looking at someone different, someone that would possibly attain gravity in our lives.

Wriggling her hand free, she reached up, and cupping the back of my neck, pulled me in for a kiss. No introduction, no 'pleased to meet you', no nothing. We didn't need that. The connection was there from the start. We began our friendship with her tongue in my mouth. So fitting.

As our tongues mingled, dancing the Saliva Samba, I freed my own hands from the crushing mob, cupped her head in my palm and made love to her mouth. It must have been two minutes before we drew back. She said something I couldn't hear, and gasped hard as the man in her anus thrust in and out with a vengeance.

I leaned back in, lifting her hair with my right hand and licked and kissed her girlish neck. My right hand slithered down her front and my question was answered. Her sizable penis stood rigid at attention, held in place by the elastic band of her thong. I wedged my fingers in, sliding the flimsy fabric down and took a firm grip on her long and very thick cock. I could tell she was moaning from the vibration my lips felt on her neck rather from the sound which I could not hear over the band.

She settled into me as I stroked her. I walked my lips from her neck to the side of her chin and traversed that small distance to her lips with small, delicate kisses. God, she was such a good kisser! I knew what I wanted to do, even though I had rarely been so bold before I met her. I wedged myself in front of her, face to face, and with considerable strength, I used my own ass to force the guy in front of her to move forward just enough for me to slide down her body.

I had to time my movements to the 'en-masse' dance of the undulating crowd as they swayed to the music: down a little, stop and wait: repeat. It took a few reps to get my face in position to meet that beautiful cock for the first time. I managed to slip the gorgeous head into my mouth, but how was I going to suck this? My head was pinned to her abdomen, and the swaying of the man in front of us didn't allow for the speed necessary to ensure a proper blowjob.

The girl I would soon learn was Chloe McGill, picked up the slack, thrusting her hips to and fro. As the cock in her ass was on its out stroke, her dick thrust deeper into my mouth. I sucked hard and maneuvered my hands up and around to cup her bubble butt cheeks. She was so perfect, a sculpted work of art, and the warmth, girth and length of her would soon become my muse as I began to author my future, a script in two acts: Before Chloe and After Chloe.

Once our positioning and rhythm solidified, we became a three 'man' unit of sexual urgency. I realized momentarily that if the crowd surged, I could literally be trampled to death. Crazed faggot that I am, I didn't care. I worshiped this amazing girl's dick with mouth and throat, which precariously blocked my breathing with each thrust.

I became aware that even if I wasn't trampled, I could actually be suffocated. The crowd pushed us together, pinning my forehead to her abdomen, forcing about four of her nine inches to lodge in my throat, blocking my windpipe, not even allowing me to breathe through my nose. I pushed hard against the body in front of me and clutched Chloe's hips, frantically pushing her back. She must have become aware of my predicament, because she wiggled her ass back, bringing precious air flow to my trachea as her dick receded.

Was I really willing to put my life in danger to suck a cock? I could see the headline in the paper: 'Faggot Dies Giving Blowjob', although I'm not sure what paper would report in such a fashion. Still, after a few gulps of oxygen, I was back at it, sucking her beautiful rod and fucking it with my throat. I have always thought of the weirdest things during sex, and my mind flashed to the bible quote from John 15:13, 'Greater love hath no man than this, that he lay down his life for his friend's blowjob' (or something like that).

No worries from me, I was busy. I squatted, sitting on my heels and my own stretched asshole began demanding attention. I managed to reach my purse, which was on a long strap over my shoulder, and fished out my emergency masturbation kit: an eight inch fat dildo and lube. It took some doing, what with me teetering on my heels with a nine inch cock fucking my face, but I got the lube open, squeezing out way too much onto my fat little toy.

Fumbling, I dropped the plastic bottle, which I would never find again, and maneuvered the dildo down between my wide spread cheeks. I gasped around Chloe's dick as I penetrated myself to the hilt. She caressed the top of my head as I added this new movement to our ensemble dance. I never realized that heaven could be located in a cramped, crushed together place such as this, but I had found it, and in the end, it would be the gates of my mouth that would end up pearly.

He fucked her, I fucked me, and I sucked her incredible Irish cock while furiously stroking my own, and it worked beautifully. We picked up speed, soon reaching a frenzied pace, like a finely tuned racing engine hitting the red line. I could feel Chloe's dick stiffen even more, while the nameless man fucking her asshole started wavering in his synchronization, and I knew the time was near.

Chloe began bucking her hips erratically, and I picked up the pace jerking my own cock. There was no way I was going to miss this. I needed to be on the mark and in tune, and I was.

Chloe clutched my skull hard and hurled her first stream of cum deep into my throat. I didn't taste that one, but the way she came, with huge blasts in quick succession, allowed the second spurt to coat my tongue on her out stroke. She tasted so good, my sweet little slut. There was no room for her to pull out and facialize me even a little, so I missed out on that pleasure, but as the next squirt filled my mouth to near capacity, I let some ooze out from the sides of my lips.

Through our series of bodily contact points, I could feel the short, orgasmic thrusts of Mister Anonymous Chloe-Fucker as he exploded deep in her bowels. It was as if he was cumming through her into my mouth as she continued to ejaculate at a pace that was faster than my ability to swallow. More of her luscious sperm spilled out the sides of my mouth as she savagely fucked my gaping maw.

I could feel the trembling in Chloe's body as she slumped, satiated. It was only the tightness of the crowd that held her up. As her precious cock had nothing more to give me, I let it slip from my mouth with one last sensuous lick along its underside. Even in the dim light, I could see her fucker's unsheathed dick exit her hole. I did not hesitate, and wiggled my tongue in there for a taste.

I lathered her now gaping asshole with peppered licks, shoving my stiffened tongue up inside her anus to meet the coming flow of gravity-driven sperm. I didn't know either of these people, but somehow, I figured that if this beautiful girl allowed this man to shoot his cum into her ass, he must be okay. Quite frankly, when a taste of ejaculate is available, I tend to abandon all reason anyway.

Soon, I felt the flow of warm cum across my tongue, and I lapped it up eagerly, with my own version of whorish abandon. The anonymous man had given her a good amount of himself, and I took it from her, coaxing it out of her asshole with my flickering, digging tongue. Some dripped off to the ground below, but I swallowed that which I had captured. My throat warmed to the sticky flow as it slid down my gullet.

As I would have expected, the pure taste of the escaping semen told me that Chloe cleaned herself meticulously, as I always did myself. There was no 'ass-to-mouth' funkiness at all. I briefly entertained the notion that, if I could wander up her asshole, through her anal canal and into her bowels, the walls of her rectum would sparkle in purity like a crystal cave.

Above me, Chloe shook hard, her body still jerking from her intense orgasm as she ground her gaping asshole onto my face. Even in my precarious position, preoccupied with my search and sperm-rescue mission inside her anus, I felt like I loved her already. Feeding on the cum leaking from her well fucked hole, the pickings had become slim. I swallowed two or three times, and I was sated. Now I'd sampled him and her, but I really didn't care about him.

As I humped on the dildo penetrating my anus, I felt my own cum rising, that spectacular warmth spreading from my balls, up my shaft to the tip, rushing me headlong into my own orgasm. Licking Chloe's gaping asshole clean of the last vestiges of her paramour's ejaculate, I enjoyed the topography of her crater surrounded gape. I struggled to burrow my hand down between our sardine-close bodies to aid in my own release.

Hands-free, my cock spewed its first mighty spurt onto my palm as it neared my engorged rod, lubing it for the job at hand. Grasping myself firmly, I stroked and lunged my ass up and down on my toy. I couldn't see it, but I knew that I was squirting my most copious load in recent memory. I was in pure bliss, wedged precariously within this massive throng of humanity, an ultra-nasty, cum-breath sissy masturbating in public with a dildo up my ass. This was actually very unlike me at this point in my faggot career.

Shot after gooey shot burst forth from deep within my writhing body. If not for the mob holding me firmly in place, I would most certainly have lost my balance and fallen, squirting my cum all over myself. Although I couldn't see, I would soon learn that I had coated Chloe's stocking clad calves, ankles and patent leather stillettoes with my pearly seed. I slumped in exhaustion, fortunately propped up by the crowd around me.

Soon, I felt her hands on my head, sliding down to my neck and pulling me up. Struggling to my feet, no sooner had I brought my face to hers, when she lunged in for a deep kiss. I felt the vibration of her moans as she tasted both her and her friend's sperm on my tongue. We cum-kissed for a prolonged period, oblivious to the crowd as it undulated around us, our arms wrapped around each other. The dildo slipped out of my asshole, and I would never see it again. C'est La Vie.

The guy whose cum now coated both of our mouths had vanished, and we extricated ourselves from the mob, finally reaching the street full of partiers. She kissed my hand, gazed up into my eyes, and for the first time, I heard her most excellent girl voice.

"I'm Chloe McGill, and it's a very distinct pleasure to make your acquaintance."

"The pleasure is all mine. I'm Faye, Faye Gella."

She giggled, that most endearing of sounds which I would come to treasure, and leaned in, whispering in my ear, "You most certainly are."

We became the textbook definition of fast friends. I soon learned what an ultra freak she was when I discovered that she had no idea who the man whose sperm I had just sucked out of her asshole. Because of the density of the crowd, she never clearly saw his face. He had been crushed up behind her with a huge boner rubbing against her ass cheeks, so she had reached behind her, freed his anonymous cock, and guided him into her anus. A few minutes after that is when I showed up.

God bless Chloe McGill, my little maniac.

As of this writing, Chloe has been living in Australia with her new husband for four years. I've seen her only twice since then, had a rambunctious three-way with her and hubby Sean (not our first), and once we met up here in Los Angeles when she was settling some of her late mother's business affairs. Naturally, we didn't play then, but it was enough for me just to see her, honored to provide a warm shoulder to cry on for this amazing, unique creature.

While she was at first just a casual hookup, it was not long before my dearest Chloe would become my most treasured friend. A truly real person, the only 'lie' about her was the nine inch shaved Irish penis lurking underneath her girly frills.

On occasion, I've wished that we could have loved each other as life partners, but both of us wanted the same thing: a 'real' man. For me, a man or a very understanding woman would do, although I had only ever been in love with women. At that point, I wasn't sure I could ever have that emotional relationship with a man, so in theory, Chloe would have perfectly bridged that gap. Fooling around and having mind-blowing sissy sex together was one thing, but Chloe and I were destined to be soul-mate friends at best. And that best is far better than good enough.

She is a striking beauty, like Maureen O'Hara in her prime, and every bit as strong and willful as Maureen's screen persona. With a 28 inch waist, long toned legs, and that flaming mane of wavy red hair flowing down to the middle of her back, she could (and did) get the straightest of men to kneel down in front of her.

Before Chloe, I rarely went out in public dressed, because I don't pass nearly as well as her. The only times I would brave it were at events like the Pride Parade, where I felt protected by a huge buffer zone of people like me. She was the one who convinced me that crossdressing and passing was a sliding scale, and wherever your God given looks placed you on that scale, you needed to own it, and do the best you can with what you've got.

I gradually accepted that the men who wanted me would want me not because they could fool themselves into pretending I was really a woman, but because I was a man wearing women's clothes: a faggot, possibly the naughtiest (in my mind) of all the sub-phyla of the gay family. It was true, and she taught me that about myself. I am bisexual, but when I play gay, I want to be the biggest fag I can be. I don't want to be a woman: I want to suck cock and get butt fucked dressed as a woman, but I am always a man nonetheless.

When Chloe and Sean first saw each other, I was there. Unfortunately, my boyfriend was out of the country, but we played separately with each other's knowledge and permission. It was a huge party in the Hollywood Hills, at the intersection of bi, gay, CD and tranny. I liked Sean well enough, but Chloe and he fell in love, literally at first sight. I had only seen this in movies, but leave it to Chloe to prove once again that fantasies can become reality.

That night, I literally watched her life transform. It was like a movie, where everyone else in the room froze in time, leaving only Chloe and Sean animated as they discovered each other. She saw him first, talking to the host and his tranny wife. Chloe made a beeline for them, giving the wife a hug and kiss. She introduced them, and that, as they say, was all she wrote.

A while later, I could feel their new love course from his body into hers as he fucked her anus from behind while she sucked my cock. I was pounding my own asshole up and down on some guy's eight inch rod. I didn't even know my butt fucker's name, but that was not uncommon the way these parties unfolded. All around us, at least forty people fucked, sucked rimmed and generally slobbered all over each other wherever there was a foot or two of free space.

As Sean slammed himself into the new and future love of his life, she looked up at me. I'll never forget that look. Even with her lips on my dick, I knew. I saw her, and I knew. I can't explain how, but this incredible thing that happened between them was obvious from the first hello, and snowballed from there+. I had never seen Chloe look at any other person the way she looked at Sean.

It was in her eyes as she blew me. She was happier than I'd ever seen her, and I'd seen this girl pretty goddamn happy. But it was not the 'I'm getting fucked really well' kind of happy, this was so much more. Tears of joy welled up in my eyes, causing my eyeliner to run. She was so beautiful, so deserving of true unconditional love. I loved her and was overcome with happiness for her.

She had been there when I had met my own boyfriend, and showed no jealousy, only full, loving support. Now I knew what that felt like, and was happy beyond tears to feel that for her. I think very few people could detect the sadness of the unfulfilled that lurked deep within her soul, even while she joyously attacked her life of wanton sex. Even through the front she put up, I knew it was there.

So there I was, bouncing on a cock, with Chloe sucking my dick, and I'm crying. Sean and Chloe both noticed. As impossible as it sounds, she knew exactly why. She lifted her mouth off me, steadied her doggy position with one hand, reached up, cupped the back of my neck with the other, and brought my face close to hers. It reminded me of the moment we first met, and it only made me cry all the harder.

Cheek to cheek, she whispered, "You know I'll always love you."

I kissed her hard, as passionately as I ever had, and slobbered, "I love you Chloe. I hope it's real."

She sucked my tongue from its root to its tip, letting it go, and pulling back. "It is."

I straightened back up, my eyes still locked with Chloe's. The trance was broken as a huge pole of black cock closed in on my face, framed by a white garter belt and stockings, which swooped in towards my mouth. I opened wide and giggled. It reminded me of the way you feed a baby, swooping the spoon towards their mouth like an airplane. I hungrily wrapped my lips around the massive head of this gorgeous fat black rod. I was at a party, and I needed to break this weird trance and be the fun girl people rightfully expected me to be.