Night of Firsts

At some point I would ask Nicole how she found out about my fetish for women's panties. At the moment, I couldn't ask her anything, a pink pair of her sodden satin underwear was stuffed in my mouth and serving quite ably as a gag.

My wrists were bound to the bedposts with silk scarves, my ankles pulled back toward my head and also tied to the bedposts. A pink dildo had been worked into my ass over several excruciating minutes. The word "SLUT" had been written on my cheeks in lipstick and was clearly visible to me in the mirror on the wall adjacent from the foot of the bed. She'd even been thoughtful enough to write it backwards so I could read it clearly.

To say the least, I wasn't very comfortable, but my cock was betraying my enjoyment of the situation. My hard on had been raging since the panties had been put in my mouth.

For her part, Nicole had left the room, and I couldn't imagine what she had in mind to continue my pleasurable suffering.

I had been left in my predicament for perhaps a half hour before the door knob turned and Nicole entered the room that had become my torture chamber. She was dressed as she had been at the start of this, in a black cocktail dress with spaghetti straps and a plunging backline. Her mocha brown hair was pulled back in a strict pony tail; her green eyes sparkled as she surveyed her handiwork. Her gorgeous legs were clad in thigh high stockings and her feet were adorned with shiny 3 inch heels.

"Comfy?" She asked coyly.

"Mmmm" I mumbled through the panties.

"Ahh, cat got your tongue?" She teased as she approached the bed. It was at this moment that I noticed the riding crop in her hand. She noticed my eyes lock onto the toy. "That's right; I'm going to spank you now." She purred.

She caressed my butt cheeks with the business end of the crop, running over the protruding phallus. "You've been a good boy." She said, referring to my adherence to her parting instructions. "You kept that cock in your ass this whole time, and those pretty panties are still in your mouth. I like a boy who can follow simple instructions."

I tried to mumble something but was cut off by the slap and sting of the crop across my ass. My stifled mumble turned to a stifled scream. A second soon followed, and then another and another. In no time at all I had been whipped fifteen times.

"Go ahead and cry little boy, you're my bitch, you may as well ball like one." Nicole said as she used the tip of the crop to caress my stinging backside. I was wincing in pain when she grabbed me by the hair and jerked my head up. "Look in the mirror." She commanded, and I obeyed. My behind had been turned a bright shade of crimson by the crop.

"I suppose you didn't like that whipping that much." She grinned as she picked up my flaccid cock in her hand and stroked it back to semi erect. "Punishment time's not over yet though." She said venomously. Nicole gave my cock a final hard squeeze, and then let it go. She trailed her long manicured finger nails up my stomach and chest, stopping to twist a nipple before reaching for the panties and jerking them out of my mouth. She placed the garment on my cock, the silk felt exquisite against my most sensitive areas.

"I'm going to whip you now Slut. You are going to do two things. First, you will thank me after every strike, and second, you will not let those panties fall off your body; so no jerking around. Understand?"

"Yes."

"And keep this cock in your ass." she said, grabbing the exposed end and twisting the dildo around in my rear.

"Okay." I barely gulped the word. Suddenly the whip came down on the back of my thigh. I had been expecting to get more on my ass, hitting the sensitive part of my leg made me jerk. The panties slid off my body, it was all I could do to keep the dildo where it was.

"It didn't take you long to fuck that one up did it slut?" Nicole said as she landed the crop on the other thigh.

I let out a tremendous yelp. "What do you say?" She reminded me.

"Thank you."

The crop next landed on the bottom of my left foot. I was totally surprised again and could feel the cock sliding out of my ass. The next shot landed on my right foot and the torture was too much to handle. I could feel that the head of the dildo was the only thing holding it in. I struggled to close myself around it, to keep it within me. Keeping it in became my single focus, which made the next blow to my thigh a little easier to deal with. It was at this moment, that I realized I was completely in Nicole's power. I was humiliated, taking a beating, and struggling to do what? To hold a fake cock in my ass! Why? Because she had told me to and that was all that mattered.

It was when Nicole struck my ass with the whip and reminded me that I hadn't been following her other command that a full on flurry of swats descended upon my exposed and aching flesh. The whip seemed to hit everywhere at once. My thighs, my ass and my feet were all assaulted. I have no idea how many times she hit me, but it was enough to make me lose the dildo from inside me. By the time it was over, I was sobbing uncontrollably, sweating profusely, and begging shamelessly for her to forgive me.

"Shhhh. It's okay slut." She calmed me as she untied my ankles. I lowered my legs painfully as blood flowed freely back into my feet. I watched her as she picked up the panties and placed them back on my cock; she stroked me slowly as she looked at my sweaty face. "You've been a good boy." She said in soft tones as she stroked my cock to full erection.

"Thank you." I murmured.

"Do you like the way my panties feel around your cock?" She teased.

"Yes."

"You're a panty boy aren't you?" Se continued.

"No." I don't know what last shred of dignity I thought I was protecting with that lie.

"Please!" she protested, "You love fucking my panties, you're the biggest panty slut I've ever seen. Admit that you'd do anything for my panties or I'll stop jerking you off with them."

"I love your panties, please don't stop." I begged way too fast for my own comfort.

"Silly boy," She laughed. "Did you like the taste of my panties in your mouth?" She asked as she continued to stroke my cock with the garment.

"Yes." I answered.

"Do you know that I masturbated in these very panties this afternoon?" She said.

"Really?"

"Oh yes. I had very nice afternoon cum in these panties, could you taste it?"

"Yes." In truth, I had been so completely caught off guard by the whole event; the whole thing was a blur. But it was clear that no was not a word Nicole was interested in hearing at the moment.

"Would you like to have an orgasm in my panties too?" She asked as she caressed my raging hard on with the warm underwear.

"Yes." I stammered truthfully.

"Ask me." She purred.

"Can I have an orgasm in your panties?" I asked.

"May I?" She corrected me.

"May I have an orgasm in your panties?" I asked again.

With her free hand she slapped me across the face. "Where are your manners?"

The humiliation of the moment only served to make me more turned on. I could feel the orgasm rising within. "Please may I have an orgasm in your panties?" I managed through gritted teeth.

She stroked my cock harder and faster. I was going to cum any second. And then she stopped. "You may not." She said as she released my cock and stood up. "Ladies first," She smiled as she raised her little dress over her head and deposited it on the floor. She was naked except for her stockings and heels.

"You're going to eat my pussy, if you make me happy, I'll let you fuck my panties some more." With that she climbed on the bed and straddled my body, lowering her ass onto my face. I reached out with my tongue and licked her sex eagerly. Being tied to the bedposts made the task harder, but I was so eager to please Nicole I lapped at her like a man possessed.

Nicole ground her ass onto my face. I tongued the folds of her pussy and only realized I couldn't breathe when she raised her perfectly shaped ass to allow me to do so. The positioning was awkward, so Nicole turned around so she was facing me. Her knees rested on my biceps, but I hardly noticed after she lowered her clit to my mouth for servicing. Nicole rode my face, using the headboard for support. As my lips and cheeks became sticky with her cream, and the sound of her moans reached an octave I hadn't heard before, I knew I was succeeding at pleasuring my tormentor. I nearly suffocated as Nicole climaxed.

"Mmmm." She moaned as she extricated herself from the bed. "Goooood Boy." She said grinning at me. She picked up the panties and used them to clean my face. Then she carefully wrapped the panties around my cock and began to stroke me again. I was aroused in moments. Nicole mercifully left out the teasing this time around.

"Fuck my panties whore." Was all she said as she stroked my cock hard and fast. It took only moments, I convulsed and moaned as I shot my cum into Nicole's very dirty underwear.

I should have seen what was coming next, but in the post ejaculation euphoria, I could barely remember my name, let alone discern what torment she had yet to inflict on me. The taste of my seamen on her panties as she shoved them back into my mouth drew me back from my post cum reverie into the moment.

"Lick up your cream Nancy, and turn over." Nicole commanded. She had already completely emasculated me this night, but giving me a girl name was a nice additional touch.

The silken ropes that bound my wrists were long enough that I could turn over, crossing them in over my head as I did so. Nicole ordered me onto my hands and knees and I found the restraints accommodating to this new position. "Get all of your nasty cum out of my little panties whore." She commanded as she took the garment from my mouth and gestured for me to extend my tongue. She ran the cum soaked panties across my tongue over and over, then wiped the panties all over my face, making sure to push the most fragrant spots against my nostrils. She left the garment on the bed beneath my face and told me I had earned the right to keep licking her panties while she changed. I did as I was told, sneaking a peak at my dominatrix's shapely derrière as she sauntered out of the room for the second time.

When Nicole returned maybe twenty minutes later, I had tired and nearly fell asleep. The door opening startled me back to full consciousness, but I wasn't fast enough to hide my sin from my Dominatrix. "Am I boring you?" She asked.

"No." I stammered.

"I guess giving you an orgasm wasn't such a good idea." She cooed as she ran her fingernails over my ass. "One of the reasons women are superior to men is that we can go on having orgasm after juicy orgasm, while you pathetic losers cum once and your done." She squeezed my balls as she spoke the final phrase through clinched teeth. "I won't make that mistake again Nancy. You simply will not be allowed to cum again tonight. I dare you to disobey." She grinned.

Nicole had changed into a black see thru robe that hung down to mid thigh and nothing else. She wore the robe open. To say that she looked sexy was an understatement. She had released her hair from the pony tail, and it now flowed freely around her shoulders.

"I don't think we need these restraints anymore." She said as she untied my wrists. "You want to be here, don't you slut?"

"Yes." I said

"You will address me as Mistress, or Ma'am. Do you understand me?"

"Yes Ma'am." I responded.

"Thank you for untying me Mistress." I offered trying to gain favor.

"Oh you're so very welcome. There's no need for bondage once the slave is broken." She said as she undid the last of the bonds.

The words "slave" and "broken" hung in the air as I considered what I had been through and what may yet be left to come. I realized all at once that I was in fact both of those things. I would follow Nicole's every command, which made me a slave to her, and I would do so willingly, which meant that I was in fact broken.

As if to accent the point, Nicole wrapped a leather collar around my neck and fastened it tight enough to make me understand what it meant. She clipped on a leash and my transformation from boyfriend to sex slave was complete. She took hold of the end of the leash and led me off the bed. I instinctively went to all fours once I was on the floor. Nicole seemed to approve as she led me out of the room and across the hall to her master bedroom.

The room was lit with dozens of candles which made it bright enough to see, but not bright enough to notice the array of toys Nicole had set out on the dresser. She led me to an oval carpet at the foot of the bed and told me to stay there. Nicole kicked off her shoes and climbed onto the bed. She sat up against the headboard, her legs extended out in front of her. "Do you think I'm pretty?" She asked.

It was such a silly question, I almost didn't answer.

"Do you?" Her voice didn't rise, but it was clear I was to respond.

"Yes." I said.

"Did you forget your lesson already?" She asked in the same soothing tone.

"No Mistress. Yes I think you are pretty Mistress."

"Don't make that mistake again. The room next door is for punishment, this room is for pleasure; where you spend the rest of the weekend will depend on if you can be a good little fuck slave."

"Yes Mistress."

"What part of my body do you like the most slut?" She asked the question as she opened her robe all the way, and raised her right knee, dragging her toe along her left leg.

I was certain it was a trap, so I hesitated to answer.

"Come on now, be honest with me, what part of my body do you think about when you are stroking that little cock of yours?"

I still wasn't sure, but offered an answer anyway. "Your backside Ma'am."

"I might have guessed; a panty slut like you would have to be an ass man wouldn't he?"

"Yes Ma'am." I didn't know what else to say. My girlfriend had turned into the sexiest dominatrix ever, and I had no idea how to handle it.

Nicole rolled over on the bed. She propped herself up on her elbows and looked at me over her shoulder. "Come here and kiss my ass slave." She cooed.

I did as I was told, crawling onto the bed and between her parted thighs. Before tonight, we hadn't done any kind of anal anything. Like everything else so far, I had no idea what I was doing. I tentatively placed a peck on her cheek, ah, ass cheek.

"Pathetic." Was all Nicole said, "Try again."

I pressed harder in about the same spot. The curve of her buttocks melded with my lips, and I dared a little lick of her soft skin.

"Better." She said. "More." She commanded.

I ran my tongue along the curve of her gorgeous derriere and planted a series of kisses where her buttocks and thigh met. To my delight, I heard her purr as I kissed her in this newly found erogenous zone.

I was in the process of trying to figure out what to do next, Nicole was kind enough to make the decision for me, "Now my asshole." She said it like she was asking me to pass the salt. And I dutifully passed it, slipping my tongue into the crease of her ass and rimming her puckered little hole.

"Mmmm," She purred as she nestled her head into a pillow and closed her eyes. "Finger my pussy while you lick my asshole slave." She ordered.

Her sex was wet and I slid two fingers inside of her with little trouble. She put her right hand beneath her and started fingering her clit as I stimulated her from behind. At some later time I would realize that all five senses had been immersed in her sex in that moment. The sounds of my fingers sliding in and out of her wet pussy, along with her soft moans were music to my ears. The smell of sex, candles and perfume filled the room. The taste of her ass certainly wasn't something I had experienced before, but I was eagerly lapping at her as if it were my final meal. And the feel of her soft sexy body against my face and hands was amazing. I was completely under her control and loving every moment of it.

The pitch of her moans changed and brought me back to full focus, I realized I was about to give my sexy tormentor another orgasm. Bringing her to that place suddenly became my sole mission in life. My tongue grew more eager, and my fingers slid in and out of her aggressively. I curved them inside of her trying to reach her sensitive spots. She bucked against my face and moaned uncontrollably. When it was nearly over she pulled away from me, rolling over and off of the bed. "Hands and knees bitch," She growled seductively as she crossed the room to her dresser.

From my position I couldn't see what she was doing, but her next statement gave me a clue. "You like fucking doggy style right slut?"

The correct answer, both at that moment and any other moment; all be it for different reasons, was yes; and I said as much. But I thought I knew what was about to happen and the way I was about to have doggy sex wasn't going to be like any time I'd had it before. The suspicion was confirmed when I felt her lubricated finger begin to work some cream into my ass.

"It was nice of you to pleasure my ass dear; I thought it was only right that I return the favor." I could hear the wicked smile in her voice.

I'd never done anything like this before and was seriously considering protesting when I felt the head of her strap on press against my back passage. I clinched out of reflex and was rewarded with a slap across the ass. "Don't you want me to fuck you in the ass slave?" Nicole asked.

Remembering that no wasn't a word I was using tonight, I said "Yes Mistress."

"Yes what?" She teased, pressing the head of the cock harder against me without fully penetrating me.

She wanted me to say it. I didn't want to say it. She spanked me again. I said it. "Please fuck my ass Mistress."

"Good boy." She said dragging out the word boy and sliding the dildo inside of me as she did. I thought it was going to be more difficult, but she had trained me with the other dildo earlier. I began to wonder just how long she'd been thinking of this little plan.

She started slowly, but worked herself into a pretty decent in and out pace. Her hands clutched my hips and pulled me into her pelvis with every thrust. At first I wasn't really that thrilled about things, but in short order I was rocking back to meet her thrust and enjoying the sound of my ass slapping against her. It was a sound I had heard before, but not from this perspective.

She put her hand in the center of my back and pushed my face down into the pillow. She fucked me like this for several minutes as I moaned into her pillow with every thrust. I lost track of time and had no idea how long I'd been fucked when I felt the dildo slide out of my ass. "Roll over she commanded.

I did as I was told and she straddled my body. The black faux cock jutted out from her body and inched its way closer and closer to my mouth. I knew she was going to make me suck it, and I was sure that I was going to draw the line right there. Ultimately however, the line was crossed with little fanfare and the dildo was in my mouth with no resistance. I was mortified at the moment, but would learn later that it had been wrapped in a condom in my rear, which she had removed while I was rolling over.

But I didn't know that then, and I couldn't believe what new depths I was being taken too by my formally sweet, relatively innocent girlfriend. I was sucking a cock that had been in my butt. Thankfully Nicole didn't give me a lot of time to think about it as she started telling me exactly how to suck a cock.

"Lick the head, swirl your tongue around it. Mmmm, good boy. Now take it into your mouth, just a little bit..... Deeper...... Deeper. You're a great cocksucker slut."

The humiliation knew no bounds. I was glad I didn't taste anything terribly nasty and so I sucked the cock like I knew what I was doing. Somewhere along the way she unsnapped the harness and removed the dildo from it. She told me to keep it in my mouth as she dismounted the bed and went back to the dresser. I watched her strip out of the strap on harness and take something else with a bunch of straps off the dresser. When she returned she straddled my body again and rested her ass and pussy on my chest. I could feel her wetness against me and wondered how happy I should be that she seemed to be endlessly turned on by tormenting me.