The next day I had no classes. Thank god. I tried staying in bed, hoping that everything had transpired over the last week would simply cease to exist. My reverie was cut short by a burst from the telephone which was sitting way to close to my pillow for comfort. Unwittingly, I answered, still weary from the prior evening, “Hello?”
“Good morning Stevie,” Kirsten practically chirped. “What’s the matter, is my little bitch tired from last night? That was nothing, you better start getting in better shape.”
Ten seconds before, I would have done anything to sleep. Now, despite the heaviness of my head, my cock started to rise…just from her voice. “Yes Mistress.”
“Oh that is how to be addressed first thing, very good Stevie. I want you to know that I was proud of you last night. You let a lot of inhibitions go. I you perform as well tonight, I have decided to give you back the original of the video from your room.”
“Really!..I mean, thank you Mistress.”
“Oh that is sweet, self-educating. Just what one would expect from one of one’s professors.” I cringed as I did every time I was forced to recognize that one of my students now controlled my every move, my professional future and increasing the rise and fall of my sexual arousal.
“Anyway…Stevie get a room at the Motel 6 on Route 87 by five o’clock and call this number back to let me know the number. I expect you dressed to the nines, blindfolded and ready…”
I gulped. Was I supposed to fill in the void. The silence was deafening. To be fucked, Mistress.”
Suddenly noise again, she had simply put me on hold. “Well that is good too, but I was just going to say for anything. But wishes have a way of coming true, don’t you think Stevie?”
Not really a question, but an answer was required anyway, “Yes, Mistress.” I could not believe how quickly I had succumbed to Kirsten. Was it me or her or both? All I really knew was that evening I was to be dressed as a woman, undoubtedly humiliated in some machiavellian manner, fucked like a little sissy all at the whim of one very hot but getting twisted coed, and my cock raged hard at the prospect.
I showed up at the hotel early and paid in cash. I went straight to the room to prepare. I had new stockings and took some pride in getting every hair off my body. I had lost it; there was no longer any doubt, but now the thought of getting something back was driving me. When I stopped to be honest later, I realized that was not really the case. I had been pulled in by the thrill and, frankly, Kirsten’s good looks and the freedom that was living on an edge, any edge: mine just happened to be on the fringe of decent society. I knew that I had to go along with everything that she said that evening and tried to prepare myself. I should have known better.
I was all set, but when I tried to use the phone it would not work. I was informed that I would have to come to the lobby to sign a waiver to pay the charges. Already dressed up, there was no way I could go back down now. “Is there any other way?”
“Well, you could always use a credit card.” There was no way she could have foreseen this, or had she. Was she that far ahead of me.
Sighing, “OK, the number is….”
The call finally went through. “Hello.” Definitely not Kirsten!
“Uh..Is Kirsten there?” I managed.
“Hmm Kirsten….” The silence deadened. “And who is this?”
My turn to hesitate. Was this some form of test. “Well!” she demanded.
“MLS.” slipped out before I could stop it.
“And what the hell does that mean….Professor.” I literally started to shake. Even as I tried to assess the situation, I heard Kirsten in the background, “Make him tell you,” and the giggle.
It chilled me right to my panty clad cock already stiff as a board. “My little slut,” I whispered.
“What? You will have to speak up professor, I thought you said my little slut.”
“Yes, that is what I said,” cheeks aflame.
“So why do you want to talk to Kirsten slut-boy.” No relief. “Is it to remind her how much you like being dressed in panties for her, waiting to suck and get fucked by her hard cock while I watch you?”
There was no good response, “I..uh.”
“No. Maybe it is to tell her that you have been thinking about your promise and that you do really want to suck a real cock and have it shoot all over your face as she cums from pounding your pussy ass with her strap-on…”
“Well, Professor which is it? You can tell me you little perve. After all I’ve seen you in action. You like it!”
Kirsten now, “Yes what, slut. Make me believe what you want: what I need to hear you want.”
“I want to make you cum. To feel you against my face.”
“I don’t think you would be dressed as a whore on you knees in a hotel room, if that were all. Do you Steffie? I like that better, no?”
“I would do more to please you.”
“What do you expect to do tonight?”
“Everything you tell me to do.”
“Good. Is you blindfold on?” I heard the door open. “No need to say anything more. I am pleased with your obedience so far Steffie. Better than before. I do like a quick learner. You can put down the phone now.”
“Steffie, what a pretty skirt. Good call having it flow so it is easy to lift out of the way!” As if to prove a point, I felt the material pull from my legs and a cool draft shimmy up the stockings towards my crotch; where my rigid cock had to be visible.
“Kirsten. Do you really think he is going to believe your friend Stephanie is who you say?”
Who was he. What was going on. She must have sensed my sudden concern. “You know Summer, I do like Stephanie. It adds something; a complete submission.” Her voice chilled over the last.
Turning to me, I felt her breath on my cheek. “You told me you wanted to suck cock. To feel a hard cock push into your mouth as I watched, enjoying your show. Didn’t you Stephanie?”
“Don’t hesitate Stephanie. I have warned you about that before. I wont tolerate it in front of my friends. They don’t believe everything I told them, and you certainly don’t want to embarrass me, do you?”
Embarrass her. I was the one cross-dressed apparently about to beg to suck one of her friend’s cock as her classmate, my student, looked on. “I did say that.”
“That I would suck a cock for you.”
“For me?” How she could feign incredulity, I did not understand.
“So if you had a hard cock slapping on your face right now, you would not reach for without my telling you to do so?”
How could I respond.
“I mean,” she move closer to me so I could feel her, smell her, as her hand slipped up my skirt (my skirt?) to my raging cock, “Be honest, the thought of having a hard cock slapping on your cheek then sliding over your lips, across your tongue, filling your mouth with hot smooth flesh turns you on, doesn’t it?”
No time. “I feel what talking about it does. How you react to thinking about being my cock whore. Why won’t you admit what I know; what you are, Stephanie?”
“I don’t know…Mistress.”
“Why you won’t admit that you want cock or what you would do with a hard cock on your lips?”
A knock on the door. I felt my hands drawn back. Shocked, I did not struggle as they were clamped together. “Well, Stephanie, I guess we will soon have the answer to at least one of my questions.”
“She, Stephanie. You may look the part of a cock slut, but you still sound like my professor. I don’t think our new guest needs to know his servicer…yet.” And she laughed as Summer giggled.
“Come in Dan.”
Dan? What Dan did I know. I couldn’t think of a one. “Summer promised you a little show first, didn’t she?”
“Yes, please is what I think you meant to say, right Danny.” Her voice was gilded. I almost yelled for the poor bastard to get out, but somehow remained silent.
I heard her slip off her dress. I knew that had to have an impact. “Yes please Kirsten. I would love to see whatever show you wanted.”
“Good. But if you are going to see my friend Stephanie suck my strap-on, I want to see your cock. It turns me on to watch you get big.”
“Sounds fair.” I heard a quick zipper and pants falling away, even as Kirsten bent down to my face again. “Don’t disappoint me or you’ll be sorry. If you trust me, all will be fine.” she whispered.
As she straightened, I felt the familiar shape of her strap-on graze my chin. Instinctively, I reached for it. She responded by thrusting it sharply into my mouth, almost making me gag. “I guess that is one question answered,” I heard Summer murmur.
“Not yet, but soon,” Kirsten responded even as she picked up her rhythm. I barely heard the word. I was focused on her cock. I guess I was a quick learner in some respects. I was totally keyed in to her excitement, wanting, no needing, to feel those final thrust leading to the spasms of her first sharp orgasm. They came remarkably quickly, and she sat back.
Her breath still ragged, “Come here.”
Not knowing whether she was speaking to me, I inched forward. Dan had too. “It seem you liked what you saw, didn’t you Danny.”
“Yes,” almost strained. The voice came from above me.
I felt Kirsten’s hand slide up my skirt and push into my cock. I pushed back against her. “You like that don’t you Stephanie.”
Even as I opened my mouth, “Yes, Mist….” I felt the head of Dan’s apparently very hard cock push against my lips.
Kirsten in my ear, “Don’t disappoint.” I opened my mouth further. His cock pulled away. I followed, unconsciously.
“Oh you do want it don’t you Stephanie.”
I hesitated. My voice. She told me not to speak. Had I already said to much? Did this guy already know?
“Yes.” I gave in.
Now fully in role, “Please let me suck his cock Mistress.”
Inhaling deeply, knowing somehow I was about to cross another line. “Because, I want to know what it would feel like. Because you want me too. Because the thought of being yours turns me on.”
“How could I say know to that?” I felt Dan’s cock against my face again. It length stretching across my left cheek from lips to ear. I thought I heard some whispering by the door.
Before I could turn my head towards his cock. “Wait, I want everyone to hear that again.”
My voice cracked, luckily I suppose, “Please let me suck his cock Mistress.”
“Please. I need to. I want to feel him fill my mouth, slide in and out over my lips.”
“I think you actually want it, don’t you slut!”
“Yes Mistress,” actually believing it.
“I can’t believe that I have made you into such a tramp in only two weeks, can you Steffie.” I felt the hard cock slap one side of my face as her strap-on grazed the other.
Should I say something…
“I mean talk about a transformation. I should have gotten more before and after shots.” More whispering…something familiar about one of them.
My attention was directed above me again. Kirsten squatted. I felt her wetness encase in the leather straps of her harness rest on my now exposed thigh. She whispered warmly in my ear, “I think you need to beg Dan to fuck you now Stephen.” WHAT!
“Wha….” was all I managed, however.
“Stephen,” she continued nibbling my ear, “This is what I want. I told your reward for behaving, and you certainly can figure out the penalty for disobeying.” Before I could respond, she continued, “As a little extra insurance, I brought in someone who just might enjoy the show.”
My mind reeled, who could serve as insurance. Hadn’t she humiliated me enough? “Do you want to know who is watching you Steffie,” now louder again.
“I…” was unsure. “I…”
“Well I for one want to see your eyes as Dan fucks your little ass; that is what you want isn’t it P…I mean Steffie?”
“Sorry, did you say something.”
Broken, not realizing how much blacker things were about to become, “Dan, please fuck my ass. I want to feel your hard cock deep inside me when it explodes.”
“As much as you want him in your mouth?”
“Good, then with every thrust, I want you to picture his hard cock sliding into your mouth getting ready to burst while I look on.”
Dan was behind me then. I was pushed forward and I felt her guide his cock to my ass. He must have blindfolded as well, as I felt Kirsten guide his hands to my hips. “Start slow,” she instructed.
I felt his cock head on my ass even as Kirsten pushed the blindfold down my face over my chin. I blinked in the dim light of the room. Kirsten blocked my view. Squatting in front of me her strap-on pointing at my face obscenely bobbing from her glistening crotch. She had put on a corset which hugged her tan waist and pushed her perfect breast higher. She hitched a strand of hair that must have escaped her ponytail during the first fucking of my mouth that evening behind her right ear as she whispered again, almost conspiratorially giving me the death knell to security, “When I stand, take a good look at the woman in the chair. If you don’t want me to disrobe your piece by piece as Dan fucks you, you are going to beg to be fucked hard like the slut you want to be. I want you wanton. I think you will agree in a moment. She was the cat with ten canaries as she sat back preparing to revel in my facial expression.
I knew what she was waiting for and was determined not to give in. She won, however, of course. My ex-girlfriend Erika sat in the chair and listened as I begged to be fucked, screwed, filled with cock over the next five minutes as Dan fucked me onto Kirsten shiny hard strap-on. I was a whore for all intents and purposes, a slut debasing myself solely so Erika didn’t learn that it was me begging to suck cock earlier that night at the behest of one my students no less. I should have known better.
“Oh God, this is one tight ass,” Dan muttered as I felt him speed up pushing me hard into the plastic cock in front of me.
“Isn’t it the best.” Kirsten gasped, baiting the hook further.
“Yeah, I am going to cum.”
“Wait, turn her over.” I felt my leg being raised through the thigh-high as my skirt billowed down to my neck.
Kirsten slid to the opposite side of my head as Erika gazed intently at the enfolding climax. Kirsten dropped her gentle lips to my mouth forcing her tongue where her cock had just left. Pulling back, she whispered, “Jack off slut and come with Dan like a good girl.”
She couldn’t recognize me from there. Could she? I was still dressed up. As Kirsten’s thrusts became shorter so as to hit her clit me quickly, I felt my cock respond despite myself. Of course Kirsten took that opportunity to assert, “Erika, didn’t I tell you he was a slut. See how hard he gets from being fucked for us.”
I thought I would die even as I heard Erika low voice, “Yes, he’s everything you promised.”
“Tell them what you want. Its your show too, Erika.”
I could not believe she was getting into this. I never knew, but then I had never done anything like this either. “Come on the little slut’s face Dan. That is what I want to see,” she directed.
He thrust deep inside me then pulled back, me hips falling almost to the bed even as she moved around behind him. I saw his cock directly in front of my face, her hand reached around its girth even as mine slipped from my grasp. “You want this cock, don’t you cunt.”
I looked at Kirsten. She nodded. “Yes,” I managed as Kirsten withdrew her cock from my mouth for a moment.
“Say it again, Steffie,” Erika chastised as she stared down at me.
Somehow, I felt even more exposed now than while being fucked. “I want to suck that cock. To feel it come.”
“Really,” one eyebrow arching. “And what will you do if I let you suck it, Steffie?”
As she looked down at me, she grasped the base of my cock, pushing her finger down my shaft almost to my ass. My cock twitched in her hand, nearly exploding. Would she recognize the feel; it hadn’t been that long ago. I thought I saw a flash in her eye as Kirsten pulled back and bent over me, “You better play along or all the clothes will come off and who knows what she might do when seeing her ex like this. Troubling isn’t it professor.”
“Whatever you wan…” my mouth was filled again by Kirsten’s cock.
“I want you to beg to let me fuck your ass, Stephanie. That is what I want!”
I was talking too much, she had to know, but no acknowledgment yet. “Beg!”
Kirsten did not stop this time. I mumbled, “Please..want you to…fuck…my ass…with your…cock.”
My dainty little ex bent over and picked up a shiny black phallus. You want me to fuck your ass with this Steffie.
“Yesss.” I managed.
“Oh God, I love this. This is my new class picture every time you open your mouth.” A flash went off. “That is going to make me come,” Kirsten rasped.
“Again,” demanded Erika.
“Please, let me…”
“Yes, yes, take it slut.” Kirsten rasped driving against my cheeks harder as she squeezed me head between her hands fucking my face at will, before finally pushing me off and squatting back on her haunches. “Go, I love doing that,” she murmured, a light sheen making her tan skin shine in the room’s dim light.
Even as I tried to catch my breath. “If you want it, you better put it on me now. I want you to show me how much you are willing to do to suck cock you little tramp.” Hearing Erika degrade me like this should have shriveled my cock and made me take some sort of action, but tellingly I was still under Kirsten’s spell. This further abuse only made my cock more rigid; the elastic of the panties holding it tightly against my stomach.
She pulled me from the bed, and I rose kneeling in front of her. I held the straps as she stepped into the harness; only placing her cock against my face as I snapped the last of the closures of the harness in to place. “Make me wet,” Erika directed as she pushed the head of her cock past my lips. Soon her hips found a steadier rhythm even as she pulled Dan’s cock to my face, dragging across my cheek, slapping on my nose. I was out of my body. This all could not really be happening.
She grabbed my hair, pulling me off her cock, turning my whole body around. “Tell me what you want Steffie.”
I should have been more prepared. “I want you to fuck me Er…”
Oh my god, “I want you to fuck me mistress.” I tried to cover.
“Because you want to…”
“Why else slut?”
“Because I would love to have you come by fucking me.”
“What about you? Don’t cunts like you like to be fucked?”
“Yes, Mistress. I would like it too.”
“Then why should I let you suck this cock.”
“Too late slut, why don’t you watch Kirsten stroke that big dick in your face and think about it pushing through your lips, stretching your mouth, its warmth filling you even as it swells before exploding into your mouth, down your throat, over your face.”
I felt my thong being pulled to the side and her hard plastic cock push into me as I saw Kirsten’s hand grab the base of Dan’s cock and swing towards my lips.
Erika grabbed my hips as she worked her cock into my ass with short thrusts at first until she was buried and I could almost feel her short hairs tickle my ass as the leather from her harness pushed into my skin. She did not waste any time and has soon fucking me hard, Slamming deeply into me with each thrust. Each thrush pushing my whole body forward so that my lips grazed Dan’s now dripping cock being stroked before my very eyes.
As Erika’s thrust began sharper and her breath quickened as I knew it would, the continued abuse combined with the stimulation of my prostrate began to have its effect as my own cock neared explosion.
Almost without stopping, I was turned again. “I want to see him shoot on your face as I cum,” Erika explained.
“Oh god reach for it Steffie, use your tongue, and we will all come.”
The possibility of release was too much. I didn’t care anymore. I need to cum. I felt the elastic of the panties cutting into the hardness of my cock as it pulsed trying to free itself. I reached out with my tongue and caught the soft underside of Dan’s cock.
“You are a cocksucker, aren’t you.” She gasped.
“For you,” I responded.
“No, but you will be our cum slut yet, Steffie. Look up.”
My tongue still extended. I looked up into Erika’s eyes even as the first load shot over my cheek in to my mouth. I winced despite myself as the second, then third and fourth salvos streamed onto my face, on my nose, into my hair. He must have been saving this load too. I felt covered even as Erika moaned. Her own orgasm triggered by my humiliation and the building pressure against her clit.
Kirsten seemed to know exactly what Erika wanted and slapped Dan’s cock against my cum-covered cheeks pushing his cum into my skin and towards my mouth, “Lick!”
Erika stopped, just as my own orgasm was about to begin. I teetered on the edge of no return when my cock now pointed towards my face would have thrust of its own accord for what seemed like minutes, but was probably a millisecond.
Still buried deep inside me, Erika freed my cock from the now damp, but tightened panties. Grasping the base tightly, she resumed tiny movements with her cock. She was done, completely spent. I was already covered with another guys cum. Kirsten smiled above me: the Cheshire again What? I couldn’t think. All of my focus was between my legs.
I felt my whole body start to tremble. This time I could not be stopped. My come literally percolated and began to push down my shaft. “I always did think you would make a passable girl, Steven,” was the last thing I heard before the first blast of my come caught me n the chin. Her voice, so matter-of-fact, even while I was experiencing one of the strongest orgasms of my life, exacerbated my complete humiliation, “but I never thought you would make as good a cum slut as all this,” she continued as my cock continued to spasm, further covering my face and neck. I felt the come start to liquify and drip down.
I was almost in another place as I heard the beeping. “Just in time, the battery must be almost dead.”