Expectations be Damned

The car came to a slow stop. I could hear the engine idling for a few seconds before it stopped abruptly. The silence was amplified by my nervousness.

It's not like I'd never done this before, but it had been a while. "Ready?" I heard a playful voice from the driver's seat chip in. Looking over at Caroline for the first time since getting in her car I saw her contagious smile and nodded shyly.

"You don't need to be nervous," she said sympathetically. "I've been here a million times and my friends get special treatment." I tried to smile convincingly. "I'm fine, don't worry about me," I dodged. We both knew I was avoiding conflict.

I had known Caroline for most of my adult life. We met in college and had remained good friends ever since. Like many friendships I've had with beautiful women, it started as a crush. I just wanted to be near her. I never made a move, and it didn't bother me after a while. I was so used to this recurring theme that we pretty naturally moved into a regular friendship.

She was always much more outgoing than me, dragging me to parties and get togethers that I probably would have avoided altogether without her persistence.

"You think too much." I could hear her voice in my head as she'd said it so many times before. Maybe she was right.

Beautiful as she was, we had been through so much together that I rarely felt nervous around her, or really thought of her in a sexual way. Tonight, she had called me after work and said she needed to blow off some steam at the bar.

So here I was, about to wander into the socially lubricated chaos of "The Stetson", a surprisingly divey joint downtown. I had heard plenty about its wild tendencies, but had never experienced them myself. Following the slam of the car door I was pushed mindlessly inside the 19th century building by the relentless cold.

A fireplace burned near the center of the room nestled inside of a brick chimney. I settled onto the bar stool closest to it, removing my jacket.

"You get started without me," Caroline said. "I'm gonna go to the bathroom." Caroline disappeared into the back of the place.

Left on my own, I tried to get the bar tender's attention. It would be nice to take the edge off as soon as possible. Of course, something like that is easier said than done in a crowded bar. The boisterous, the outgoing, and the beautiful were rewarded one by one as I watched a brick wall of anxiety build around me.

Thirty voices chattered together to make an incomprehensible pool of sound. As it engulfed my ears and poured into my stream of racing thoughts, I considered going home. Caroline would probably understand. She knew me pretty well.

Just as I wondered to myself what was taking my good friend so long I noticed someone in my peripheral. If I didn't know any better, I would think she was watching me. I could tell it was a woman, and I dared not turn my head. If I wasn't shy enough already, there was something eerily predatory about the feeling I got from her gaze. Sitting in my head, I began to speculate if she was actually looking at me at all.

What if I looked and she wasn't? Then she would surely notice me when I tried to check, and I did not have the confidence to flash her the kind of smile I wished to. It had happened a million times.

I always felt like a creep for looking. For getting my hopes up. For those dirty thoughts that preceded my morals. In my head I would be screaming respect, but all that would be seen was my wandering eyes that I just couldn't help. I felt sick. Something had to change.

Gathering my nerve, I wondered what was the worst that could happen. I turned slowly, gears grinding. I was fighting a magnet that held my head in the world of the safe and known. When I met her green eyes my own snapped into place and then ricocheted around the room. Her confident smile gripped me. She WAS looking at me. I was frozen, looking back at her now.

She wore a short black dress with maroon leggings. Since she was sitting down, I couldn't yet tell how tall she was. What I could see was that she was stunningly curvy, with muscular thighs that transitioned perfectly into her wide hips and slender waist. Looking further up she was showing a moderate amount of cleavage, enough that I just about drooled on myself. Her face was beautiful, her features sharp. With sculpted eyebrows that added an intimidating air to her bright green eyes. Everything about her screamed confidence.

She crossed her legs. And even though the leggings covered all, my eyes still darted down and back up again. She saw, and her smile grew. My face grew as red as her lips. She motioned for me to come over.

One foot and then another, I somehow managed to make it the four steps over to her without falling on my face. I took a seat next to her on the booth, carefully measuring so I would be pretty close, but not crowding her.

"I'm Mara." As she introduced herself her foot gently kicked me in the shin. Something immediately began to stir in my pants.

"Tim." I shook her hand and it lingered a little bit long.

"Pleasure," Mara responded, still grasping my hand. The way she said it pierced me

Maybe I should pause a second and let you in on some of my proclivities. I'm extremely sensitive to being touched in a sensual way. It doesn't happen often, so when it does I'm pretty much immediately under a spell. I have always tended toward the submissive side.

I had really only had fantasies until this point, and they usually had to do with being tied up by a strong woman and used for her pleasure. Since I was very small, I had been swept away by reveries of dressing in women's clothes, sometimes even having female body parts. I had never told anyone.

Just borrowed clothes in secret when I could, often taking them from donation bins or occasionally a laundromat. But no one could know. It would bring me too much anxiety.

"You seem a little nervous," Mara ventured. Wherever did she get that idea? I was smiling a dopy smile. It was stuck on my face. Tension was building around my temples. "Yeah, it's not often I meet someone like you," I stuttered.

She kept a playful demeanor. "And how would you describe someone like me?" Despite her accessible tone I fumbled to think of an answer. "A woman so beautiful and confident and flowing with allure," is what I wanted to say. Sounds good, right? My tongue stayed stationary.

After a pause she broke the silence. "Mmm, luckily I know a lot about someone like you. You like someone to direct you. Your so shy, but redeemingly cute. And you've been waiting a long time for someone to bring it out of you." There was so much complexity crammed into the way she said the word "it". She had released it with such impact, and it sent a slight chill through me.

Right then, at probably the most awkward moment possible, Caroline returned. "Wow! Making new friends?", she beamed happily. "I'm Caroline!" Mara cooly looked up and said "I'm Mara, and actually we were just about to head back to my place." I was mortified, but managed to look up at Caroline with a confused smile. She didn't seem as shaken as I would have expected.

Here I felt horrible because that would mean leaving her here on her own but she grinned back and said "Alright, have fun! Nice to meet you." She couldn't help but laugh part way through. And just like that, Mara stood up and said "And you as well." before walking toward the door. I trailed behind, looking back at Caroline and mouthing "sorry". She gave me a goofy thumbs up that let me know it was okay.

When I got outside, Mara grabbed my hand and we walked presumably toward her car. It was a jet black jaguar, almost as intimidating as she. I approached the passenger door, waiting for it to be unlocked. "Aren't you going to get the door for me?" she asked flatly.

I stumbled over as quickly as possible, muttering an apology as I let her into her own driver's seat. "Sorry, what?" Mara asked teasingly, and not as harshly as her previous question. I knew the drill. Though I had no experience, I had spent more than a healthy amount of time researching my kinks on the internet. "Sorry Mistress!", I blurted out. Mara seemed pleased. "Not bad, but let's go with Goddess."

As we pulled away in the car, she wasted no time. "So what's your deal, are you a sissy slut?" I've never felt the blood move so quickly away from my brain. "Um, maybe. Yes," I replied bashfully. "Do you want me to hurt you?", she continued onward. "I'm not really into extreme pain, but I do like it a little rough."

"A little rough", she mused to herself. "Alright, and do you want me to play with that cute little ass of yours?" I gulped. Her hand reached over and ran up my leg. Slowly making her way up my inner thigh. She felt my rock hard bulge. "Mmm, I like that answer sweety, but I want to hear it from your pretty lips." I responded quietly, almost whispering "Yes." "Yes, what?", Mara pressed further. "I want you to play with my cute little ass, Goddess." "Music to my ears, slut."

She hit the gas, and the car hummed through the darkened streets like a cat on the prowl. I wondered how this woman could know me so well, just at a glance. Had she been watching me? The drive back wasn't long, but it felt like forever with my thoughts racing. Her impossible calm stood in stark contrast. Despite my fears and reservations, she pulled me in.

Made me want to be close to her, and rest my head against her shoulder. As we drove, her hand continued to work it's magic, teasing my leg. I was breathing deeply to try and keep calm. It seemed she was aware of my breath as her hand moved up toward my crotch as I breathed deeply in, and then down the inside of my thigh as I exhaled.

She had quickly pulled me into a trance. It wasn't long before we pulled up to where she presumably lived. The car came to a slow stop. I could hear the engine idling for a few seconds before stopping abruptly. The silence was amplified by my nervousness.

I realized she wanted me to go get her door for her. I scrambled out and opened it up. Mara climbed out and squeezed my butt before smiling at me. "Quick learner," she said. "Come on."

She walked gracefully toward a floor-level door with bars across it. We weren't in the best neighborhood I could tell. "She must have spent it all on the car," I thought to myself. Once inside I knew I was wrong. The place was an aesthetic wonderland. I took a deep breath of the intoxicating aroma. It smelled like the most beautiful flowers, mixed with the smell of her. Her arousal was evident as she forcefully pushed me onto a pink love seat.

The goddess climbed on top of me and kissed me deeply as her legs spread over me. I went to grab her hips to push them down onto my cock. Before I could get a grip she took my hands and stretched them over my head. I moaned in complaint but she lapped it up just like a sweet dessert.

I didn't have anything to complain about anyway. I was now in my naturally subservient position with her tongue exploring my mouth and her hips grinding against mine. I was letting go. Breathing, moaning, and listening as she told me everything she wanted to do to me.

"We're going to make you sooo pretty." She freed my hand momentarily so she could trace my lips with her finger. "Then I'm going to tie you up and make you beg." Her voice was so full of intimate heat and kept me hanging on each syllable. As her words penetrated my ears, they sank into my head leaving no room for anything else. I was fully concentrated on her without any effort. I was so willingly under her control.

"There are so many surprises in store for you tonight. I can't wait to take your slutty little hole. It's a shame I won't get to take your virginity!" This confused me. First of all, I was definitely still an anal virgin. But even so, she couldn't know whether I was or not. I was so caught up in everything that I just brushed it off as she continued to whisper in my ear, and nibble on my neck.

After another short eternity, Goddess Mara rolled off of me teasingly saying, "It's time to get you ready." With that, she handed me a small baggy full of hygiene supplies. "In here I have some hair removal cream, an anal douche, and some pretty smelling soaps. I want you to be hairless and all cleaned out. Oh!" She skipped over to a bag over by her front door and pulled out a skimpy pink thong with white lace. "And you are to come out wearing these, and only these. Take your time, cause I have a phone call to make. Now go!" She slapped me hard on the ass and I gasped before running into the bathroom.

It was simple enough cleaning myself up. I just focused on trying to calm my nerves. I'd never done this before. An hour ago I had never imagined I would let anyone in on my secret. Now I was in a stranger's bathroom making myself more vulnerable than I had ever been. I didn't even know this girl. Let alone know if I could trust her. But something seemed natural and right. And let's face it, I was desperate for outlet. I turned off the hot water, drying off and slipping into the panties. Then checked my handiwork in the mirror. I was clean and hairless alright.

One deep breath later I was turning the door handle. When I opened the door, the strangest thing happened. Seated on the couch was Mara, dressed even sexier than before in large-holed fishnets and all black lingerie, with bare feet. But sitting next to her was a woman identically clad. And strangely familiar.

There sat Caroline, like I'd never seen her before. Remember when I said I was never nervous around her or thought of her in a sexual way?

Well this was different. As they both smiled at me something clicked in my brain. This was too much. This was someone that knew me. Someone I had real history with. Someone who knew my family and all of my friends. Tears welled up in my eyes. I quickly retreated back into the bathroom, locking the door. I was back where I had been so many times. Dressed up, behind a locked door. I was crying.

"Sweetheart," Caroline's voice spoke softly through the door. "I know you weren't expecting this. And I know it's not easy for me to spring it on you like this. It's just...I had to know." In all of our years knowing each other I had always seen Caroline's bubbly personality. She had never used this tone with me.

It was so heavy, and so real. "You see, I've had a feeling that you were a kinky girl on the inside for some time. And that's what I like. But we're such good friends. And I didn't want to ruin it. And I could only think of one way to know for sure."

It clicked into place. Of course she had known Mara from the very start of the night. Mara was helping her find out the truth. With everything coming together in my mind I had zoned out and was missing what Caroline was saying. I tuned back in just in time to hear a familiar sort of sentence. "I could never just ask you. I was afraid you'd think I was some sort of..."

"Freak?" The word came out of my mouth mindlessly. It came out like vomit, and my tears flowed freely.

Caroline was silent for a while. I was too. The next time she spoke something had changed in her demeanor. Her words came pouring through the locked door like a master key. "I want to know what you're thinking. You look so sexy in those panties that I don't know what it would be like to go back to normal. Well..." I moved to the door and slowly turned the knob. One click and one creak later I fell at her feet. I looked up at her and she ran her fingers through my long hair.

"Whaddaya say?" There wasn't an ounce of hesitation left in me. "I want you," I said as sure as I had been in my life. Caroline came down to my level and embraced me. "I understand if you need time to process this. It's been a long day." I'm not so sure she understood how long I'd been waiting to get this part of me out.

I looked in her eyes and grinned so big she got the message quite easily. "Mmmm, someone is ready. Back into the bathroom, cutie." I looked over at Mara and noticed that she had been crying too. We all had. But we were all smiling now.

The two gorgeous goddesses cornered me into the bathroom. Mara held the bag from by the door, and Caroline held my hand. My surprises were far from over. "On your knees, bitch," said Caroline. Once again, her tone of voice had changed. There was so much more going on inside her than I had ever thought to consider. I complied. She stuck a heel into my back and asked, "What do we say?" "Yes mistress. Thank you Mistress." Mmmm, I quite like that," Mistress Caroline cood.

"Now here's what's going to happen. You're going to do exactly as we say, and without hesitation. You will thank us as often as possible. Afterall, if not for our actions you would either be at home jerking off or at least awkwardly sitting on a bar stool."

"Yes Mistress. Thank you so much Mistress," I replied sincerely.

Mara procured my outfit to be from the bag. And damn, had they picked something straight from my fantasies. It was a pink nighty that matched my panties and had built in garter straps to connect with matching stockings.

The nighty didn't quite cover my ass and barely kept my nipples hidden. The back had very little material, finishing in a V shape near my lower back. Finishing the look was a pair of five inch heels and a little pink collar that said bitch on it in bold, black letters. "Get dressed, slut."

I moved as quickly as I could but the two shoved me back and forth a bit, making it difficult. It was playful but deliberate and I felt so helpless. Yes, these women were physically stronger than I expected but their extraordinarily smooth demeanors in connection with their stunning bodies had me truly at their mercy. When I finished getting into my lingerie they sat me on a stool in front of the mirror, turning on a blinding light.

Caroline washed my face with a moisturizing wipe, preparing me and simultaneously wiping away any trace of tears on my face. Next, Mara began to apply foundation. The jaw-dropping duo tag teamed for probably 45 minutes, applying contours, blush, eye liner, mascara, eye shadow, and finally lipstick and shiny pink lip gloss.

They plucked at my eyebrows, curled my hair, and removed traces of sideburn. I probably don't even know everything they did. But when it was over and they turned off the bright light I looked into the mirror.

I could not believe my eyes. How beautiful I had become. This beat the hell out of every single time I sat at home and applied a mediocre attempt at eye-liner and what was probably a lot more lipstick than was tasteful. No, this was different. I looked like a woman.

It made me want to cry for entirely different reasons. At last I felt like the creature I was meant to be. My moment was short lived. As soon as we had all drank in our success the two each pinched a nipple and used it to drag me out of the bathroom and toward Mara's bedroom.

Mara pushed me onto the bed as forcefully as she had pushed me before and they both mauled me. Sitting on top of me and stroking all over my body. Mara pulled my hands up above my head and locked them into a pair of cuffs conveniently placed at the head of the bed. Caroline did the same with my feet on the other side. They were spread out wide, exposing me. Just like that, I was quickly immobilized.

"Now we've got you completely at our mercy. Do you like it when I slap your ass?" Caroline landed a rough hand on my panty-clad butt. As I began to cry out Mara put a finger across my lips and said, "Shhh...the real answer is it doesn't matter." "Now," Caroline interjected, "The safe word is mercy. And until we hear you utter it, you will be shown none." She lightly touched the head of my cock through the panties.

"Ooh, our sissy little bitch likes this. She loves being dressed like a little whore." "Well of course she does, that's exactly what she is." Mara retorted. The two goddesses continued to lay their hands all over me. Mara pinching my nipples and intruding between my lips, and Caroline teasing my hard cock lightly while violently groping my butt. My new mistress stroked the inside of my thighs. Leading up slowly toward my crotch, and trailing down between my ass cheeks and teasing around my hole.