Ladies Night at the Leather Bar Ch. 02

Now that you've met Chloe in Part One:

Today I want to remind myself of how much I owe her for luring me into the circumstances wherein I met a beautiful man, a man who would change not only my life, but my basic conception of myself. I found him in the most unexpected of places. A place where Chloe brought me.

SUMMER 2011. THE SAN FERNANDO VALLEY.

I had just gotten home from work, put on my makeup and changed into some old, torn black fishnets and garter belt, but I couldn't decide on a top. I was holding a black bra in one hand, and a black slip in the other. On week nights, with no plans, I usually wore old things when I went to bed. My cell rang. It was Chloe.

"Chloe sweetie!! What are you doing?"

"Oh, Faye, baby! I have got the most awesome party for us tonight!"

I frowned down at my shabby stockings, but smiled into the phone. "Really? Where are we going?"

"Fucking Heaven, sweetie: butt fucked, cum soaked gaping ass Heaven. Look, I'm just down here at Topanga and Shoup - I can be there in two minutes. Are you decent?"

I had to laugh out loud, "It depends on who you ask."

Two minutes later, she flourished into my living room, hugged me, gave a quick kiss on the lips and stepped back to look at me. She was dressed in a severely tight black pencil skirt, a white satin blouse with her black bra visible underneath, sheer black nylons and black six inch stilettos. Always perfection.

"Come on, we're going to have to get you ready."

I looked down at my shabby fishnets, and stammered, "I was just gonna wear this to bed."

She hugged me again, clenching me to her chest, then kissed me deeply, her tongue saying hello to my tonsils. I sucked around it, relishing, as always, this exquisite creature. Then she backed her tongue out of my oral driveway and from two inches away, looked deeply into my eyes with that special love she had for me.

She whispered, "You could wear a trash bag and you'd still be the most beautiful girl in the world, but you're going out now. Do you need to clean yourself out?"

"No. I'm good. I did it before work."

"What did you eat for lunch?"

"I just picked up a burrito from Chipotle."

She giggled and caressed my hair, "Oh God, sweetie, you'd better go do it again."

As usual, Chloe was right. I performed a series of enemas, using first a dilution of mild liquid soap, then several with plain water. Even though I had been fairly clean, my anus had certainly not been up to dinner standards. I topped it all off with my favorite spearmint douche, which left my bowels tingly cool and I presume, delicious.

Once I emerged in a robe, Chloe grabbed my hand and whisked me into my huge walk in closet. I have two opposing rows: my 'Naughty' wall and my 'Nice' wall (kind of silly, because technically, they're all naughty). I watched as she ran her finger across my 'Nice' wall of apparel. She stopped and pulled out one of my most girly things: a bright pink and white plaid latex schoolgirl getup with a pleated latex skirt. She held it up against me, and I took it as she stepped back to look.

"Mmm, eighty percent. Keep holding it up."

From opposing walls, she pulled down a satin blouse just like hers, only pink, and one of my naughtiest outfits. It was basically a bunch of leather straps held together by metal rings - the kind of thing that looks like something you'd use to bridle a horse until you put it on. I don't really go in for BDSM as a rule, but I love the clothes. She held it up against me and considered both outfits for a moment.

I was a little mystified. "Where are we going that these are the choices?"

That was a stupid question. Knowing Chloe, these two options would be viable in any circumstance. Her attitude alone would make either of them work at a White House dinner. Well, maybe the Clinton White House.

"It's a surprise. You trust me, don't you?"

I giggled, "Of course."

Chloe put back the leather harness ensemble, "Let's go virginal."

So, I was going as an ultra-feminine teenage schoolgirl. Okay, so my motif for the evening would be 'innocence defiled'. Totally down with that, I was already getting excited. Below, snugged up in my panties, my cock moved a little all by itself.

She grabbed a pair of pink six inch heels with 'fuck-me' straps around the ankles and whisked me back out into my bedroom, and snugged her arm around my waist, kissing my cheek.

"Let's get to work."

She painted clothes on me like Picasso addressing a blank canvas. Pink fishnets, pink garter belt, a pair of those cute little frilly schoolgirl white ankle socks, a white latex g-string and white latex wrist cuffs with cuff links served as my foundation, and over it the pink and white pleated skirt, with a tight pink satin shirt tied high above the waist completing my ensemble.

She reached out, gently holding my neck as if playfully choking me. "Now, what are we going to put here?"

She disappeared into my walk-in and emerged seconds later with a white leather dog collar with a metal loop in front that anchored a four foot chain leash leading to a white leather strap handle.

My curiosity reached a peak again. "So, just where are we going again?"

She giggled, "I told you - it's a surprise, you silly girl."

She stood behind me, fastened the collar around my neck, then turned me around to face her.

"Lift your hair."

I did. We didn't have any kind of Dom/Sub aspect to our friendship, but I have always found that doing what she told me would have nothing but rewarding results. She looped the chain around my neck loosely, so it hung down slightly like a necklace, the handle dangling just above the juncture of my open blouse's cleavage.

She stepped back and admired her work, grinning at my look for the evening. She reached out, tracing her fingers around the loop of the leash handle.

"Now remember, it's up to you who you give this to."

If I was a real girl, I would have had to wring out my g-string by now. As it was, my pussy-on-a-stick was in danger of springing free from its tuck, and I'm not even a sub! I've had enough occasions where I sort of played at it, but no man is really my master, at least not in that sense.

Chloe liked the way I looked. She smiled , "We're good. Grab your tests and let's go."

"Tests? Okay, I kinda like this already."

There were certain cliques around town, including some private clubs where you could not play unless you produced STD tests like porn stars need to have. Basically, it meant that bodily fluids could be exchanged freely, without worry. Like anything ever stopped us before.

Chloe bundled me out to her car, and we drove into the night. Just as we were entering the 101 freeway, she rested here right hand on my thigh.

"God, Faye - these car rides can be so boring. Maybe we should play a game."

"Ooh! Like the one where you name a country and I have to name one that starts with the last letter of the one you said?"

"Yeah... no. Like the one where you suck my dick and I jerk your cock."

"Oh, that one."

Chloe slid her hand from my thigh, slithered it under my pleated skirt and began fondling my cock through my g-string. I turned a little, parted my legs for better access, and wiggled my head down under her arm, hiked up her pencil skirt and rubbed my hand down into her crotch. The little slut was already hard!

I craned my neck to look up her torso at her chin. "I see you're ready, as always."

She looked down into my eyes and smiled as she wrested my own schoolgirl dick from its white latex cloakroom. She spoke with this wonderful fake reproach which she did so well.

"Don't you dare make me come, and don't you come either. Every time you shoot your cum tonight is going to be an event: well attended... and with no small amount of fanfare."

I giggled. Another Chloe adventure, under way. I licked around the head of her girly-girl penis, planting tiny kisses all around the helmet. She had my own seven inches at full staff, jerking it up and down, curling her hand around the length as she masturbated me.

Fed up with just kissing the tip, I engulfed her down to the root and began fellating her with slow, sensuous strokes. At nine hard inches, every blow job I gave Chloe was deep throat, and I certainly exercised the breathing control I had developed. My lips pursed around her boi version of the 'mons veneris', that hairless little mound where the cock meets the body. With her cock a good four inches down my throat, I nibbled and 'fish-kissed' her pubic bone while swallowing continuously around her shaft for that extra stimulation.

As usual, I did this just a tad too long, and ended up violently jumping my mouth off of her dick and hitting the back of my head on the underside of the steering wheel as I gasped for air. She swerved a little, pulling her hand from my cock to steady the wheel.

"Hey! I'm driving here!"

"Sorry."

She laughed, "Just suck it nice, bitch. Don't fucking kill us."

She wrapped her fingers back around my stiffie, and I craned my neck around to look up at her.

"You know, I didn't get a chance to open myself up today, and I have no idea what kind of monsters I'm going to get up in there tonight, so..."

"Ohhhh... alright baby, sit up."

I wriggled my head out from under the steering wheel, hating to part from her delicious mouth-filler, but loving what came next. She took her right hand from my cock and held it out toward me.

"Glove me."

I sat back in my seat and pulled a latex surgical glove and lube from my purse. She splayed her fingers slightly, and I worked the glove onto her. After coating it with lube, I slumped back against the door and wiggled my left leg behind her seat, pulled my right knee up to my chin and planted my right stiletto on top of the dashboard. She looked at me and smiled as I pulled my g-string away from my asshole and grinned back at her.

"God, Faye. You're such a slut."

With that, she extended her fingers and thumb, making a five digit point, which she pressed against the outside of my anus. I wiggled my ass for her as she twisted her way in. Deep, deeper, deepest. I expelled a massive breath and moaned as she began fist fucking me in earnest (one of these days, I totally want to fist fuck a guy named Ernest).

"Hhhhh, God, baby," I cooed, and began jacking my cock in sync with her thrusts.

"Hmph. You feel loose enough to me," she laughed. "You'll use any excuse to get my fist up your ass, won't you? Shameless whore."

I panted, "It worked, didn't it?"

"When does it not, my love?"

She drove on, the amazing little multi-tasker that she is, with one hand steering the car and the other hand steering me - straight to bliss. Somewhere in the back of my mind, I thanked God for the invention of the Automatic Transmission.

Sometimes I look at cars traveling the freeway and pick one out, wondering who they are, where they're going and what their life is like. Anybody doing that with our car would never guess in a million years that inside was one crossdresser fist fucking the other while driving somewhere for a huge homo gangbang. If anybody DID guess that correctly, I would certainly want to meet them.

"Oh, God baby, fuck me... yeah!"

I thrust my hole against her dainty wrist and picked up speed on my cock stroking. She was opening and closing her fingers inside me, getting me close. I held off, centering on using my anal canal's clench and release muscles to milk her wrist. She had smallish hands and a thin wrist, but God, could she fill me up. My asshole was warm and tight around her. Then she did it, Chloe's patented move: she started rhythmically snapping her fingers deep inside me.

"Oh no, baby! Oh my God! Sweet... motherfucking... JESUS!"

I scooted my butt up in the seat, spreading my ass as wide as I could in my cramped quarters, and she fist fucked my hole hard and fast, as if she was working a speed bag in a boxing gym. I tightened and released my fairly well developed anal muscles to meet and match her enthusiastic invasion.

"You like that, Faye? You feel all full up? Sweet Mother McCrea, you are such a nasty little butt whore."

By now, I could only moan in response. I wanted to come so badly, and I was so close, but Chloe knew me to a tee, and just as I got to the brink, she pulled out abruptly. It felt like her cork was unceremoniously yanked out of my wine bottle.

"Keep your powder dry, sweetheart."

The noise I made upon her digital evacuation of my bowels was unintelligible. I gasped, and my breath started coming out in short huffs. I collapsed back against the seat, crumbling into a shaking ball, dropping my foot from the dashboard. I giggled and looked at Chloe, who diverted her eyes from the road long enough to hold her gloved hand out.

"You mind?"

I pouted, but pulled the glove off her, dropping it in a trash bag behind my seat. Readjusting my thong over my newly formed gape like a tightrope strung across a canyon, I curled around, maneuvering my face back into her lap and sucked just the head of her cock. I slithered my hand down and cupped her taut little ball sac. She wiggled her butt forward, improving my access.

If I could have seen out the window, I would have known that we were taking the natural curve of the 101 Freeway, snaking through the Cahuenga Pass over the hill, and finally exiting near Silverlake. Once on city streets, I dislodged my mouth from her dick, sat back, reached over and caressed her crimson curls.

"Are we there yet?"

She giggled, "Almost."

Then she turned off the main drag and made a right into an alley. Halfway down, she pulled into a parking lot behind a bar. Lined up along the back wall must have been twenty-five motorcycles. I looked at the small neon sign over the rear door:

"Roughrider"

I got a little teeny bit crazy. "What the fuck? Chloe! You're taking me to a LEATHER bar?"

I honestly didn't know anything about the leather crowd, but was mindful that there are so many petty prejudices between factions within the LGBT community. I tended to feel it more from gay men, with my being a bisexual man than I did as a crossdresser. Being a CD, guys are either into it or not, which is a sexual preference, but but as a bisexual male, it seems like some gay men just don't like you or trust you because you also have sex with women.

It seems ridiculous - we've all spent so many years on the wrong side of society, that you'd think we would band together regardless of our queer niche, but some people don't see it that way. United, we stand. Divided... we end up with fewer sexual partners.

Chloe chuckled at my concern, "Don't worry... you'll be great."

"I don't know anything about... leather boys! You know...I uh... you know, I don't want to be ridden rough! Well, at least not the way these guys probably do it. I don't think leather boys like girls like us."

She parked and turned to me, brushing her fingers across my cheek and smiled, "It's gonna be fine... better than fine - It's Ladies Night!"

I was quite skeptical. "Oh - a bar like this has a ladies night. Right."

"Every Wednesday. Who knew?"

"Well how did you find out about it?"

She leaned in for a quick buss on my lips. " I met one of the regulars at the beach yesterday. Real nice guy. He should be here tonight. He invited me, and I'm inviting you."

"I don't know..."

"Have I ever steered you wrong?"

"Are you forgetting the truck stop in Barstow?"

"Come on, Faye. That was on you, not making yourself clear.'

"Well, maybe you always need to spell it out, but I have to run into the one long haul trucker in the country that couldn't tell by looking at me that I was a man."

"You're prettier than you think."

"I dunno... he must have come from a town full of ugly women."

"Faye, you are an exquisitely beautiful creation. There is not an ugly gene in the entire scope of your ancestry. But you still need to be clear about it with strangers."

"No. YOU need to be clear. I'm not fooling anybody."

"Except that trucker in Barstow."

"Yeah, Stevie Wonder with a tractor trailer."

She giggled, "Okay, well anyway, this isn't that. Come on."

She opened her door and got out. I clutched the door handle on my side, but did not pull it. She circled around to my side and stood there, hands on hips, with a slightly exasperated look on her face. She opened my door, but I made no move to swing my legs out.

She let out a sigh and leaned in putting her face an inch from mine, and whispered, "You know I love you, right?"

I nodded.

"And you know I'd never do anything to hurt you, right?"

Again, I could only muster a nod. She ran her right hand across my satin blouse, caressing me just below my neck. I was feeling a little better about it, but was far from convinced. Reasonable or not, I was scared. These biker, leather boys and their rough practices were diametrically opposed to me and mine.

She gave me a light kiss on the lips while she curled her hand into the handle of the leash that circled my neck. Gently, she pulled and cooed into my ear.

"The lady doth protest too much, me thinks."

She was right, of course. I didn't get all dressed up and come all this way to back out now. I trusted Chloe, and we both knew I was going in. She led me by the leash to the bar entrance, where she stopped, released the handle and adjusted the chain around my neck, which she had pulled tight. She stepped back, looking me over.

"You know I've got your back, sweetie."

"Am I gonna need you to have my back?"

She just gave me that look: 'enough already' and opened the door, curled her arm around my waist and ushered me inside this leather-bound den of iniquity.

We strolled along a short hallway to another door, and we went in. I felt like Dorothy when she opened the door of her fallen house into the full color world of Munchkin land. Definitely not Kansas, and certainly not populated by little people, as I would soon learn.

Inside, a burly bear sat, with his cub sitting on his lap, arm around his daddy's neck. We knew the drill, and both fished out our paperwork and handed it to him. He scanned over our tests and nodded, handing them back to us.

"Have a good time, ladies."

We thanked him and strutted in towards the bar. The place was very masculine, furnished with motorcycle decor. A classic Harley hung suspended from the high ceiling. 'Born To Be Wild' by Steppenwolf played in the background. 'Get your motor runnin', to be sure.

Chloe sat at the bar, but I felt more comfortable standing, scanning the room. There were all shapes and sizes of these strange, alien rough boys. I guessed there were about forty guys in the main room. I spotted two T-girls I didn't recognize mixed in with the crowd. I could smell the leather, and it was, I have to admit, immediately intoxicating.

I turned back as the lean, muscular bartender approached, cupping three shot glasses in each hand. He placed three, upside down in front of each of us. Chloe turned to me and gave me that demure smile of hers. I felt better already. The bartender was almost completely covered in tattoos, but looked cute, as far as I could tell through the artwork. He pointed to one of the glasses.

"Good evening ladies. The first one's on the house, the second, compliments of the gentleman at the end of the bar, and the third from the guys at that table."

We eyed the man at the end of the bar, an older black man in his mid-forties, who lifted his glass in a toast. He wore a white leather vest, open to his bare, muscular chest. I made a note to myself that I was definitely going to suck his dick at some point. Hell, I already knew I was going to going to get his cock in every orifice I had that was big enough to take it (they all were). Between his entrancing smile, the free drinks, and just the relaxed atmosphere of the place, my fears were melting away like cheap mascara during a sauna orgy.