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Sometimes, when I'm away on business, I have to find ways to satisfy my urges on a whim.
This time was no different.
Friday night I found myself in the darkened hotel room, closing in on 3am, with a 20-year old cocky little thing trussed up and gagged, recently penetrated, humiliated, and looking to me for some answers as to why he felt the way he did Broken, vulnerable from his surrender, he surely would never been the same.
The semen was still fresh on his lips, and his lashes were still wet with tears.
How it all came together still amazes me.
**
I found Taylor at a liquor store.
I had not gone out that night with the intent of finding a man to bring back to my hotel room and seduce and torture. I had simply gone out for a walk, to gather my thoughts, to try to find some serenity in the cool Chicago air.
The concierge at the hotel told me there was a music store a few blocks away. Music is always a nice diversion, so I decided to go pick up a few new compact discs. The day had been hell for me - back to back meetings with clients, a few horrific presentations and barely being able to slip out of entertaining for the evening because I was just too exhausted.
Instead I wandered down the avenue and was half way to the music store when I saw Taylor standing outside a liquor store, smoking, alone.
The only urge that I have which is sometimes as unbearable as the urge to dominate is the desire, randomly, for chocolate. Not a lot of chocolate, not a specific kind of chocolate, but something sweet. So I detoured into the liquor store and b-lined for the candy aisle, only to find Taylor lurking behind me.
He was following me.
This was odd to me, because he hardly looked like the stalker type. He looked to be about 18 or 19, in torn jeans and a black short sleeved t-shirt. His hair was dirty blonde and he had great blue eyes. As sort of a grungy type, he also needed a shave - but I guess that look is still in.
Taylor watched me pay for my small black bag of plain M&Ms and then followed me out of the liquor store.
I wasn't really worried; after all, he looked harmless.
We only got about half a block before he sped up to me, to my side and said "Excuse me."
I stopped and turned to him.
"Can I ask you for a favor?"
I wonder if Taylor ever wished he had not asked that question. Because that's what started it all.
**
Taylor wanted me to buy him a six pack of beer.
He explained this to me nervously, his hands shoved down as far into his pockets as they could go. And all I could keep thinking when I was listening to him explain how he lost is ID was, "Those are beautiful eyes."
He stammered a few times, tried small talk when I just stared at him blankly after his initial request.
"You're from out of town," he observed. People have told me I look like I'm either from LA or New York , depending on what I am wearing. I guess I didn't look Midwestern enough, even for downtown Chicago . Or maybe it was the fact that I was in a business suit.
"You aren't 21," I told him. "You didn't lose your ID. You just want someone to buy it for you. Don't lie to me. That isn't a good way to start this off."
He chuckled a little, looked down, and was shuffling his feet in that kind of "oh shucks" kind of way. Good lord, I thought to myself, is this an act, or is he really that nervous? The vibes from him were inundating me. I was totally overstimulated, to say the least.
The only thing I can compare it to is being like a starving, hungry predatory cat, wandering through the brush feeling sorry for herself, only to come upon a venison with a broken leg.
He was just asking to be captured.
"If I walk in there and buy you liquor," I pointed out to him. "It'd be on camera, and I'm sure that guy working there has seen you pull this before."
Taylor was about to defend himself, but I cut him off.
"If you want a beer, come up to my hotel down the block. I'll take a few out of the bar in the room."
Of course, I didn't expect that he'd go with that. After all, he probably wanted to go take a six pack home and party with his grunge buddies.
He bit his lip, looked at me, and said, "Which hotel?"
**
Taylor was 20.
I got him to admit that to me on the walk to the hotel. In fact, as soon as I got Taylor talking, he wouldn't shut up. He was pleasant enough, but he definitely talked too much (nervous, I would imagine).
I knew the gag would come in handy.
In fact, as Taylor probably excitedly pondered that he was about to score a few free beers, I was pondering about how I was going to score Taylor .
I went through all the thoughts in my head. How he would look bound and gagged. How he would endure pain. How he'd handle being totally used as a sex object - this hormonal, sweet little 20 year old who stands outside of liquor stores asking women ten years his senior to buy him a six pack.
Taylor had a lot to learn.
And I felt like I had struck gold.
**
Of course, the moral side of me kicked in, and I reasoned that the boy would have no more than two beers over the course of the evening, because there was no way in hell I'd deal with an inexperienced, naïve, horny kid agreeing to all sorts of humiliating acts while bombed out of his head.
No, I'd have to be careful with Taylor . And also, I didn't know if he was damaged goods.
In the hotel elevator, Taylor looked up at the illuminated room numbers with big, blue eyes. Staring at him, I noticed that he had underlying features that were quite striking - he had amazing cheekbones, for a start, and really nice lips. His face was somewhat hidden by a mop of hair and he needed a good shave. But other than that, he was quite striking.
And boy, was he nervous.
When we entered my room, I could sense that he was trembling.
Grade A venison. Ready to be devoured.
**
When I travel, I tend to stay in fairly nice hotels. After all, if I am going to be away, I at least want to be comfortable. I have learned to hate two things in the last five years: airplanes and hotel rooms.
This hotel was marginal. I'm drawn to luxurious bathrooms, large bathtubs and really nice beds. This one had all three.
Taylor , apparently, had never been inside anything other than a dark motel room for $29 a night. He tried to hide it, but his eyes were drawn around the room and I could hear him clearing his throat.
My room was equipped with a full bar, in case I needed to do any entertaining (and I guess that was good planning, on my part). I rummaged through the refrigerator and pulled out a Corona for the boy, fixing myself a Stolichnaya on the rocks.
When I handed him the beer he said "Thanks."
Then I said, "Take off your clothes."
**
I guess I prefer the direct approach. But I figure that even a naïve 20 year old has been around the block enough to know that if a woman invites him up to her room to give him a beer, she probably has some other things in mind as well.
It felt, suddenly, like a scene out of The Graduate.
Taylor was holding the beer bottle tightly, half chuckling, looking at me, as if waiting for me to bust out laughing and say "Just kidding."
But I just stood there, sipping my cocktail, and waited for him to react.
"Are you serious?" he finally asked, in almost a whisper.
"I'm completely serious," I responded.
**
Taylor finally snapped out of his daze, probably because the shock wore off and the hormones kicked in. He set his beer down on the nightstand and crossed his arms over his chest to pull the black t-shirt off.
I pulled my hair out of its large, black clip and went to the closet. I never, ever travel without an arsenal of toys, and this trip was no different - even though I knew I would only be gone two days.
When I opened my black leather bag it all started to really sink in.
I was going to have him. I was going to have him in my way, and he was going to learn to submit. I was going to use him and humiliate him and force him to make me cum, then hold him and rebuild him and make him understand why I had to do it.
I'll never forget the look in his eyes when he saw what I was holding.
**
Taylor had never seen anything like what I had. The shackles, the gags, the vibrators and of course the strap-on. I'd taken off my business suit and was just in stockings and bra at that point, and the leather strap on harness was hanging off my fingertips.
:"Oh, shit," was all Taylor could manage.
Before he could weasel away, I took his face in my hands and kissed him. He was just wearing jeans now, after managing to remove his shirt and shoes. I kissed him hard, holding his chin with one hand and moving the other hand around to his ass, pulling him close to me.
Of course I could feel how hard he was in his jeans at that point. I reached down, and under, and rubbed him through the jeans, making sure I massaged him to complete erection before parting lips and whispering, "I want you to submit to me."
His eyes were shut, his lips were still parted and he was breathing softly toward me. He was in a daze. I started unbuttoning his jeans and then he started to tremble again. He was shaking, breathing uneven now, and he was reaching around, blindly, for the beer bottle he had left on the bedside table.
I pushed it just out of his reach and said, "In a minute."
Then I reached down into his briefs and took him full in my hand.
I knew I had him. Literally.
**
It was about fifteen minutes later that I had sweet Taylor hogtied, his balls trussed up and my soiled panties tucked carefully into his mouth,. He'd thrown a bit of a fit about that, until he tasted them of course, and I quieted his protests by lowering my body onto him and resting my soaking pussy right on his nose and mouth.
I knew he couldn't breathe.
"IF you stop being such a brat about this," I said sympathetically, "I'll be much easier on you."
His legs flailed a bit, what they could with his ankles tied together and pulled up behind his back. When I eased up, I lounged momentarily in the feel of his ragged breathing at my thighs, up against my pussy. I took his face in my hands as I slid down, I looked into his eyes and I said, "Do you want to make me cum?"
He nodded. Taylor nodded with boyish enthusiasm, trying to ease up onto his elbows, find any way to get leverage, thinking he was about to be freed so he could fuck me like mad, or that the gag was going to be removed so he could lick my pussy for the next half hour.
Instead, Taylor got to watch me reach back to the dressing table and pick up the heap of leather straps, silver buckles and single, shining black dildo.
His eyes widened, he shook his head and his sweet, muffled voice said, "No."
**
Taylor was terrified. I took his face in my hands again, this time kissing him all around his lips, my hand between my legs masturbating practically on his lap. He was breathing hard, whimpering a bit, and his eyes, when they weren't screwed shut, were pleading with me.
Using my mouth, I bit down on the panties that were spilling from his mouth and pulled them out slowly. He let out a gasp and said at once, "I can't let you do that to me."
Kissing him, holding him, I reached down with the panties and started rubbing them all over his erection. I stroked him with the panties until he was dripping with pre-cum, twisting, moaning, agonizing over the need to cum.
When he looked at me, his eyes had a sweet, innocent glisten to them. I was already in my own world - just one sip of my stoli cocktail had been consumed, so I knew it wasn't the alcohol. No, I was consumed with Taylor , and his innocence. I wanted to have him
I needed to have him.
But because I was in that intense, passionate femdom mood, the one that is even more demanding that my usual mode, I wanted more than that. I didn't just wand Taylor to surrender to me, to let me fuck him in the ass and to beg for more.
I wanted him to kneel before me and fasten the buckles. I wanted him to put the harness on me, knowing full well what was going to happen. Virginal, staring right at the big, black cock that would be soon pounding into him. Methodically, gently tightening each of the leather straps so that the harness rested right on my hips and the base of the cock was positioned right at my crotch for the best stimulation.
Looking into Taylor 's eyes, which were starting to well up it with tears, I knew it was going to take some careful planning and a lot of patience.
But, I reasoned, it was only 11:30pm…
**
I released Taylor .
I released him because I knew he was on the edge of freaking out, and I knew that he was dealing with an overload of feelings and sensations. But as soon as he was freed, I locked him into handcuffs, his wrists in front, and made him kneel before me.
I made him kneel while I sat on the edge of the bed, and I reclined and ordered him to go down on me. I told him just how I wanted it, and just how long he would have to do it, and I used both hands in his hair, at the back of his head, to give further direction. By pushing, clenching my fists, pulling his head back.
Taylor was moderate in his abilities. The young ones, I noted, were always too eager and too sloppy. But he showed good promise, and I was patient. After all, this was not the end for me, this was just a step to getting what I really wanted - which was him bent over, vulnerable, begging me fuck him deeper, harder, to show him no mercy and to use him like a total whore.
While Taylor was going down on me, I told him about why I liked my harness so much.
"You need to see what it looks like," I breathed heavily, "To really appreciate it."
He just kept licking. Licking, diligently, probably to try to drown out what I was saying to him.
"When I fuck a man in the ass, I cum," I added. "And nothing excites me more than holding him by the hips, pulling him back with each thrust, feeling him open up to take me, seeing the humiliation in his face.."
By then, I was clenching Taylor 's hair so tight with both hands that I felt him wince. His whimpered were muffled by my thighs, pressed tightly around his head. I lifted my legs and wrapped them around tight, moving my hips to raise my body so he could go deeper, deeper with his tongue and bury himself right into me.
By then, I was essentially fucking his face.
In fact, the one-sided conversation was enough to set me off. I pushed him off of me, into the floor on his back, watching him raised his shackled wrists defensively, unsure of what was going on. His face was wet from going down on me, his eyes half shut, his cheeks slightly pink. Without warning, I mounted his face.
Reaching around with my hand, I took his cock full in my palm and gripped him as I fucked his face. This time, it was ruthless, unforgiving. "Tongue out," I ordered. "Keep sucking. Lick harder."
He moaned. He moaned as if it hurt, but his cock was already spurting bits of pre-cum. Taylor produced more precum than I had ever seen. I coated my palm and fingers with it and lifted my body off of him to rub it all over his lips.
He had no idea what I was doing until he licked it and tasted it, making him nearly gag from the realization, but by then I was kissing him on the lips, devouring his mouth. And I didn't give him time to complain out loud, because immediately, after that, I was sitting on his face again.
This time, I rode him until I came.
**
I think Taylor believed he was off the hook at that point. After all, I had cum - didn't that mean it was the end? And that we could move on to HIS orgasm?
Apparently Taylor had never been with a woman in her 30s.
The night was not even close to over. After all, I still had not received what I really wanted - the chance to fuck him mercilessly in the ass. I wanted to put my harness on and take him completely, to take his virginity, to use him in a way that he would never forget.
Taylor was so turned on, so desperate, I knew I could get just about anything from him. It was just a matter of time, and proper pacing. His face was still glistening with my juices, his lips were slightly swollen. His hair, disheveled, made him look even younger than his 20 years.
I tied Taylor up again. I tied him up this time so that his wrists were locked around his knees, his ankles together, his legs pressed to his chest. He was sitting on the floor and looked delightfully helpless.
So much so that I told him that once again I would masturbate. This time, for him to watch. This time, so that he could learn to please me. To want me more than anything.
Taylor looked at me apprehensively when I unfastened the black dildo from my strap on hardness. I brought it to his face and he turned away, inhaling sharply, nervous, unnerved by what he saw.
"Do you want me to stick this in my pussy?" I asked clearly.
Naked, I could see his cock start to once again stiffen. Just the naughty words did it to him.
I held him by the hair, holding his head terribly still, and started to stroke his cheeks with the dildo. I will admit, at that point, I wished it was strapped into my harness. Because I wanted to hold my hands on my hips and torture him by slapping him square across the face with my latex dick, to tease and humiliate him.
But I needed to be gentle with Taylor .
His breathing was ragged, his eyes were shut tight. I could see him clenching his fists, and the mere sight of him made me ache once again. So vulnerable, so nervous and scared. I pressed the tip of my latex dick to his lips and he shuddered and turned away.
"You will learn," I told him. "It just takes time."
**
Right then, I considered, seriously, the long term potential for Taylor . After all, I had a few slaves strewn across the United States - because I travel so much, sometimes I like to know I have a whore in a city just in case I need to use someone while on business.
Taylor had all the qualities I wanted in a whore-slave. He was young, impressionable. Passionate, a little bit nervous. He was someone I could mold into the perfect little cunt sucking whore, if I wanted.
And he was completely unable to hide his emotion - or his arousal. His cock was now fully erect, bobbing precariously even though it was tucked between his thighs and front of his body, in the tucked up position I had him in.
I was masturbating with one hand, two fingers massaging my pussy, while I pressed the dildo, again and again, to his virgin lips.
"Suck on it for me, Taylor."
I could see him shuddering, trying to speak. He was so terrified. Terrified, I know, because his dick was rock hard.
And it wasn't because I was there massaging my own pussy near his face. It was because he was turned on at the idea of being fucked in the mouth with my dildo.
"You're hard," I said, stating the obvious. "You need to lower your resistance, Taylor. Accept it. You want it."
I was sweet to him. Sweet and reassuring. I crouched down to be eye-level with him, put my hand against his cheek and he looked at me. I saw what looked like tears in his eyes, but it might have been his gag reflex kicking in at just the mere thought of having a nine inch latex dick shoved down his throat.
He said to me, sweetly, softly, his words barely coming out. "Can I have a sip of my beer?"
**
Taylor was terrified. He was terrified, but totally turned on. I fed him his beer - two large sips, that was all he could have, right out of the bottle. The feeding process turned me on, of course, and led to a whole side-event of me masturbating with the head of the beer bottle while he watched, only to make him suggestively, eagerly lick the rim while I mocked him.
Then I made him start with the beer bottle. Licking it. Licking all around the head of it, sticking his tongue in the whole. He had his eyes shut tight, nervous, but I encouraged him with words, and sometimes by reaching over and massaging his cock.
"Lick slower," I ordered. "Wrap your tongue around, slowly. All around. Suck on it now, suck on the tip. Deeper."
I pushed it in slowly, watching the neck of the bottle disappear more and more into his mouth. The sight of this made me so hot, I was soaking wet. I stopped, wet my fingers by moving them between my legs, over my pussy, and then brushed them over his lips.
He gasped, startled, tasted my wetness, then opened his eyes. They were glazed, shy. Terrified, still, but now so turned on again.
"I loved watching you suck on this," I said to him, looking carefully at the beer bottle. I hesitated a moment, then took a sip from it, suggestively, letting my tongue linger. Then, I added, "If you suck my dick, I'll cum. You do want me to cum, don't you?"
**
That's the ultimate question for a man. Any man. I don't care if he is 18 or 58.
He wants to make a woman cum.
Watching her writhe, moan, gasp. And knowing he did it to her.
Taylor wanted me to cum. There was no doubt. He wanted it bad enough, that he was starting to consider, even desire, things he thought were unthinkable only an hour before.
His eyes were so soft - timid, anxious. But not on fire anymore, not bouncing. Just staring, thinking. Shaking, only slightly.
He looked beautiful.
I held his face in my hands, this time holding the straps of my harness between the fingers of my right hand, letting it dangle next to him.
"Can I have you, Taylor ?"
He swallowed, staring at me.
I wet my lips, looked at him sweetly, and asked again, "Can I have you?"
Again, he swallowed, this time closing his eyes briefly, then nodded, and said, in a barely audible whisper, "Yes."
**
Taylor was kneeling beside me, fumbling with the buckles of my expensive, all-leather strap on harness. I stood, feet separated slightly, having to lift each leg, slowly, delicately on the spiked heels, to allow him to pull the harness up around my thighs.
He had this sweet look of concentration on his face, obviously unsure of what he was doing, watching me point here and there, at which end of which strap went into which buckle.
He was visible shaking the entire time. When the cock bobbed precariously in his face, he shuddered a bit and turned the other way.
Taylor fastened each of the buckles on either hip, making them tight, the way I like it. Then I ordered him to ease back, on the floor, and admire me from afar as I stood before him, in spiked heels and a leather strap-on harness, but with nothing else on at all.
Obviously, Taylor was speechless.
But his hard cock gave it all away.
**
Needless to say, taking Taylor 's virginity was the highlight of the evening. And probably enough for its own piece - I could write for pages about the sounds he made, how he tensed his body, how it took me twenty five minutes to lubricate him enough to even accommodate the head.
He was passionate, and innocent, and he made me want to possess him entirely.
I fucked him for a half hour. I rode his face once more, and then I tied him up and made him sleep at the foot of my bed.
In the morning, I made him bathe me before work, and then I shoved money into his palm for a cab and told him to be careful who he asked for beer when standing in front of a liquor store.
In my own taxi, on the way to my first meeting, staring idly out the cab window and reflecting on the night, I was a bit sad. Sad that I had not found out anything more about this mysterious boy, not taken down his email address, anything, to keep him touch with him for my future travels.
Until I opened up my briefcase to find a slip of hotel paper among my notes for the meeting. It said, simple, " Taylor " with a phone number. He'd obviously put it there when I had gone to sleep.
Needless to say, I found reason to be in Chicago in two more weeks.
And this time, I'm bringing a girlfriend.
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