The Sissy and the Pet

I sipped my drink and let my eyes dart back and forth between my phone and the entryway. I hadn't wanted to risk being late, so I tried to make sure to arrive 10 minutes early. Maybe I had just estimated the traffic wrong, maybe I had just been more eager for this meeting than I was prepared to admit to myself. I showed up almost 40 minutes ahead and schedule. I took my scotch to a booth in the back and did my best to be patient. I was nervous, but I tried to remind myself that the point of meeting in public this way was that, if things didn't go in a direction I liked, I could easily just stand up and walk away at any time. Moreover, I reminded myself, no one knew why I was really here. Well, almost no one.

I knew surprisingly little about the woman I was meeting. I'd never seen a picture of her and I'd never even be given a rough description of her, so while my eyes searched for her, I had to acknowledge the relative futility of the task. All I knew was that she was in her thirties, that she was very dominant, and that she was there to meet me. When a woman walked alone into the bar and started scanning, I felt my body tighten with anticipation. I wondered if I should wave, or make some kind of gesture, but when he scan came my way she locked into my instantly. I suddenly felt very exposed as she stared me down, a knowing smirk creeping across her face.

She moved quickly toward the table, like a predator that knew if had the advantage of a captive quarry. For a moment I felt myself panic as I things became real faster than I had expected. I felt very aware of the fact that they only exit to the bar was on the other side of the woman fastly approaching my booth. I expected her to take a seat in the booth across from me, but she stopped at the edge of the table and stood there, looking down on me as she spoke.

"You must be James," she said with a knowing smile.

I looked up into her eyes for just a moment, but I wasn't prepared for the intensity of her stare, and I gave in to the overwhelming urge to look down and away.

"Yes, I uh...I'm James." I replied and was greeted by silence, I realized why and quickly corrected myself. "Yes miss, I am james."

"Good boy James," she said as she put her fingers under my chin and tilted my face back to look at her. "Make room for me."

I had just expected that she would take the seat facing me on the other side of the booth, but the way she looked into my eyes had me obediently scooting over to make room for her before I had time to think about it. As she slid into place next to me, her hand went to my thigh with such a familiar casualness that I didn't even notice for half a moment. I felt her stroke up my leg and felt her eyes up and down my body. "Did you follow my instructions pet?"

"I thought...I thought you said it was optional miss." I replied as I felt my stomach tighten. She had instructed that, if I was feeling particularly brave, I should arrive for our first meeting without underwear on. I hadn't been feeling particularly brave when I had dressed to leave this evening.

She smiled and her hand stroked every close towards my cock. Even I was surprised about how hard it was already, just the way she was treating me: so bold, so assertive, so confident. "It was."

I relaxed for half a moment, but something about the way she had placed the emphasis on was lingered in my mind. The way she was raising her eyebrows at me made it evident that there was more to that phrase than I had realized. Then it clicked: it wasn't optional anymore. She saw the understanding register on my face.

"Go to the bathroom James, and when you come back you will hand me your underwear." she instructed softly but firmly, this wasn't a request.

I knew that if I did anything other than obey, this would be the end of the evening, and despite my mounting trepidation about all this, I wasn't prepared to let that happen.

"Yes miss," I said as I shifted in my seat, expecting her to stand so I could get out of the booth. But she didn't.

"No pet, I want you to crawl out under the table instead." She said with another wicked little smirk.

I hesitated for a moment, could she really be serious about that? She certainly was, I realized as I started to sink down lower and lower in the booth and slide underneath the table. I felt her gently caressing me with her feet as I crawled past her. I dared a glance to the side, hoping to peek up her skirt, but she closed her legs as if she somehow knew I was looking and wanted to deny me a glimpse of her. I crawled out from under the table and scurried to my feet.

"Oh and pet," she said as I headed towards the bathroom. "Bring a very girly drink back from the bar."

I couldn't feel my feet against the floor as I floated to the bathroom, dazed and dizzy. I was half walk to the bathroom by the time I realized that I was sporting a very obvious erection, but there was nothing I could do about that now. I tried my best to turn my body to hide it until I slipped past the swinging door to the men's room and hurried to one of the stalls. I clumsily unbuttoned my pants, dropped them, and tried to step out of them. I realized with embarrassment I hadn't taken off my shoes first, and I almost fell against the wall of the stall. I took off my shoes and stepped out of them, socks on the dirty bathroom floor. I slide off my pants and underwear, and separated the underwear from the pants. I pulled my pants back on and stuffed the underwear into my pocket.

I went to zip up, and I had to wrestle with my cock to get it back into my pants. Despite my efforts to avoid this, it quickly turned into me helplessly stroking my cock in a public bathroom. I stroked furiously, overwhelmed by how turned on I was by all this. I bit my lips as I felt myself start to go over the edge, but suddenly I panicked and stopped; my cock pulsing as it reluctantly backed away from the edge of an explosive orgasm. I realized that I had nothing to cum on, I was grateful I stopped myself before I was in a humiliating situation of cleaning up my mess from a bathroom floor with toilet paper. I waited a moment and collected myself, then zipped up and headed for the bar.

I tried to think of the girly drink I could, so when the bartender finally looked my way I ordered a fuzzy navel. I didn't even know what was in it, but it was all I could think of. I tried to make sure he saw me looking back at miss. For some reason I wanted him to know the drink wasn't for me, but he didn't seem to care either way. I took the drink back to the table where miss slid over to offer me the outside seat. I slid in next to her and her hand quickly returned to my thigh and leg, checking by touch that my underwear had disappeared. I remember her instructions and reached down to my pocket to pull out the underwear and pass it to her under the table.

"Good boy," she smiled and took my boxer shorts. She folded them once and placed them on the table where everyone could see.

"Miss, what are you doing?" I said with shock as she displayed my underwear for anyone who happened to look. She shot me a look the challenged me to dare speak like that again, and I fell silent.

"Drink your drink pet." she instructed with a gesture. I gave her a quizzical look, why was she pointing to the drink she asked me to bring her? And had she drank the rest of my scotch?

"Drink this?" I asked, confused but less confrontational.

"That's right James," she confirmed with a subtle smile. "Sit there quietly and drink that like a good girl."

Her hand slide to my cock and started to stroke me through my pants. I melted to her touch and moaned a little before I started to drink the girly beverage and let myself slide a little further under her control. I sank deeper as I felt her unzip me and start to tease me with two fingers along the underside of my shaft. I gulped down the drink quickly, feeling more light headed than I would have expected as she touched my naked cock in a semi public setting.

"Do you like when I play with your clit little slut?" she whispered into my ear, and I realized she was touching me in the way I might tease a girl. All I could do was nod my head yes and try to keep quiet.

"Good girl." she smiled and slowed her stroking under the table. "I like you James, I am going to offer to let you come home with me, if you promise to be a very obedient little slut for me."

I nodded my head again, I didn't even need a moment to consider. I wasn't sure I was doing my own thinking at that point, miss might have been doing it for me. But she cocked an eyebrow at me.

"I need you to say it out loud slut." she corrected as she moved her two fingers faster. My cock head was pulsing against belly button as she stroked my sensitive underside.

"I promise to be a very obedient little slut for you miss." I said as loud as I dared, my face flushed with shame.

"Good girl," she told me before gently sliding my cock back into my pants and zipping me up. "My car is in the garage, let's go."

Miss clasped me by the wrist and led me out of the bar, I stumbled behind her trying to hide my erection and failing utterly do to do. I could see several eyes falling on me widely opened, and I knew that the site of me being led out of the bar this way was as shocking as the tent between my legs. I was grateful that we were out of the bar before anyone had time to say anything about it. She led me through the empty parking structure to her SUV, which was parked a few spaces away from the closest car. She led me to back and popped open the hatch.

"Can't I just ride up from with you?" I joked as she opened a duffle bag in the back.

"Yes James," she replied without looking at me. "But you are going to change clothes for the drive back to my house."

A moment later I saw that she had laid out a pair of tiny pink panties, and a sheer blue nightgown; both a little too small for me, and both far far too feminine for me.

"You can't expect me to--" miss silenced me by placing her fingers to my lips.

"Quiet James. You agreed to be a VERY obedient little slut for me, and what I am not asking but telling you to do is to climb into the back of this SUV and change into nothing but the clothes I have laid of for you. You are going to be a good little sissy slut for me, or I am going to leave you right here in this parking structure and drive away. Not another word pet, get in and change."

I opened my mouth to say 'yes miss' but my instincts told me that with miss, 'not another word' meant exactly that. I crawled up into the back of her SUV and resignedly pulled the hatch back down to give me some modicum of privacy as I changed. Miss watched through the smoked glass with a satisfied smirk, but I doubted anyone else would notice me. I pulled off my slacks, my socks, my shoes, and buttoned my shirt. I paused for a moment, naked in the back of a strangers car, and realized I hadn't even had that moment I had expected to decide whether or not I really wanted to go through with this. Was it too late? Had I let me desire sweep me past the point of no return already? I couldn't deny that a substantial portion of me genuinely hoped that I had. The rest of me pulled on the panties and the nightgown and started crawling from the back seat to the passenger seat. Miss saw me move into position and took her position in the driver's seat.

"Very good girl," she said as she leaned over the seat and started to kiss me sensuously. It wasn't until now that I realized I had let her touch my cock before we had even kissed. I knew this wasn't going to be a traditional experience in any sense of the word. Her lips retreated from mine and she started the engine.

"I want you to play with your clit through your panties all the way back to my house slut." She put the car into reverse and we started to move. "It's about a 30 minute drive, so be sure to pace yourself. Under NO circumstances are you to cum in my car."

I obeyed her, closing my eyes and rubbing myself with two fingers as she had been doing earlier under the table in the bar. I moaned quietly and did my best to go slowly as she navigated the surface streets. Even I was surprised how quickly I had to slow myself down to keep from going over the edge of a quickly approaching orgasm. Miss didn't say anything to me until we got to the highway, but kept looking over and smiling at the way I was obeying her. Finally on the highway she asked me a question.

"How do you feel about pets?" she asked. It was the kind of question you asked 5 mins into a date. An icebreaker question, and here I was already deep into an intense psycho-sexual escapade and she was asking? It didn't make sense. My hormone soaked brain took what felt like half an hour just to register it.

"Pets...miss?" I askes as my fingers slowed.

She nodded. "Yes James, I have a dog, his name is John, and I think you are going to like each other." she said with a wicked grin.

"Oh, uh...well...sure I like dogs miss.But John is a funny name for a dog." I mused.

Miss gave a knowing smile. "Rub a little faster sissy slut, I want you soaking wet by the time I get you home."

***

I bit my lip at the humiliation and excitement of her feminizing me this way; I rubbed myself faster before I decided I should tell say something, after all no matter how much she treated me like a girl I would never be able to make myself wet for her. I opened my mouth to tell her as much, but then I noticed a little dark spot on the panties I was wearing. My cock had started to pump out precum. I had never been teased like this before, and didn't even realize that with the proper control I could leak precum without immediately cumming afterward. Miss noticed it as well and pushed my hand away from my cock.

"Good little sissy slut, no more touching, we don't want you cumming yet." she instructed.

"Ohhh god, misssss." I groaned in frustration but obeyed, having to sit on my hands to keep them from wandering back to my cock.

It wasn't much longer before we arrived at Miss' house. She pulled into the driveway and opened the garage door, but she didn't pull the car into the garage, she stopped in the driveway, the car still running and the headlights still on. She turned over and looked at me.

"I want to watch you get out of the car and walk into the house you little slut." She smirked.

"But miss," I hesitated, "I'm dressed like a girl, and people might see."

Miss gave an almost amused look as her hand reached over and started to grasp me through my panties.

"Silly little sissy slut," she started as she squeezed slightly. "You don't realize it yet, but you are going deep under my control, and you'll do anything I tell you to, absolutely anything. If I told you to crawl up on the hood of the car and dance against the windshield while I revved the engine and honked the horn, you would do it for me; and you're going to go so much further than even that for me tonight."

She released my cock. "Now let me watch you walk inside, and make it sexy."

I silently obeyed, opening the door and getting out of the car. I stepped into the light of the headlights, praying no one was looking. I let my hips sway both seductively and submissively as I felt her eyes on my half naked ass. I decided to take things even further, hoping that if I pleased her she might be more understanding and gentle with me. I sunk down to all fours and crawled through the garage. I waited by the garage door as she pulled her car in after me and finally closed the garage and got out of her car.

"Such a good girl," she said as she walked over and started kissing me, her hands all over my ass and her fingers sliding between my cheeks to tease me. "Are you ready to go inside?"

"Yes misssssss." I groaned as I pressed my body against hers.

She took me by the wrist again and lead me into the house, through the living room, and straight to her bedroom where she pushed my uncerimoniously back onto her bed, my legs falling open as she did.

"Take off your panties slut, but you can leave that little nightie on. It's almost time for us to fuck." She said as she unwrapped her skirt and dropped her own panties, then started looking through drawers for something.

"Oh god, yes miss!" I replied eagerly, my cock throbbing and pulsing at the thought of feeling her pussy slide down around me. I knew I wouldn't last long inside her, but hopefully I could quickly get in a second round where I could please her.

"Are you nervous about losing your virginity little slut girl?" she asked with a giggle off to my side.

"Oh miss," I smirked at the thought. "I've had sex plenty of times. Did I lead you to believe I was a virgin?"

"Who said anything about sex James?" she replied with an eager cooing. "I said you were going to get fucked."

I turned and saw her standing next to me, an ample 9" plastic cock hanging between her legs and a look of confident superiority in her eyes. She drank in the shock of me coming to the realization that I was about to get that massive toy pushed inside me. She savored that sensation for as long as she dared, but when she saw me getting ready to speak she knew she had to act quickly. It wasn't fair or right to give me time to think about this, I was to be her fucktoy, and I was to have no agency in that process. Miss would do with me as she pleased, and I would obey her. She was on me suddenly, pushing my knees up and aligning her cock with my tight virgin hole.

"Miss, please, I've never--" I started, but it was too late, she pushed and I felt the warmth and wetness of the lubricant she had already applied. My eyes went wide as, for the very first time, I felt the foreign sensation of something going up my asshole. I tried to move my hands to her hips to slow her penetration inside me, but she grabbed me by the wrists and pinned me down against the sheets.

"Be a good little cocktoy James, take every last inch of my cock inside you." she ordered, starting to buck inside me, thrusting in deeper and deeper. I found myself making deep and lasting eye contact with her as she broke my will, feeling my ability to anything but obey her dissipate more and more as she made me surrender to her anally. She started to reward me with slow strokes over my clit

"Good girl, let me fuck that tight little pussy of yours." Her thrusts become a little harder now, and I could see her lean her head back and pleasure at the bottom of every stroke as her strap on pressed back against her clit. Her cock head drove into my prostate and I felt a new kind of orgasm creeping closer and closer. Miss felt it to, and she suddenly stopped.

"You little anal whore!" she said and flipped me over onto my face. "If you're going to get fucked in the ass, we had better do it right."

I felt her drive hard inside me, my face pressed down into the sheets with every thrust. She was rough now, taking me hard enough that I would have begged her to stop if I had the capacity, but my face was buried in the sheets and my surrender to her will nearing completion. Something about being dominated this way was far too intoxicating for me to escape. I found the most feminine of moans escape my mouth as she relentlessly pounded my nearly devirginized asshole.

I was nearly in tears at this point, feeling my ass being stretched, my will broken, and my masculinity shattered and lying on the floor somewhere in the back of this woman's SUV. Despite how hard I was, an orgasm felt a million miles away against the pain, degradation, and overwhelming extremity of being fucked this way. But as I heard Miss moaning and nearing an orgasm of her own, I suddenly found myself right on the edge.

She bucked hard and grabbed my ass tight as she started to scream and pant; and as she went over the edge she decided to take me with her.