I was in San Francisco for a training course being put on by the company I worked for. I was there to learn about some new products the company was developing. I worked out of the mid-West office, which meant that I still lived fairly close to home. I grew up in a small town in Kansas.
One day during the training, the instructor casually asked me about the hotel I was staying at. When I told him the name, he looked at me a little strangely, and asked, "Is that where the corporate travel people put you?"
I replied, "I don't think the booking people in my office used corporate travel. I think they just went on-line and found the closest hotel so I wouldn't need a car."
He looked at me a little strangely, and said, "Oh. Maybe that explains it."
Other people started arriving, so he never followed up on the comment, and I forgot it.
Friday night, I decided to check out the lounge in the hotel, since it was my last night in town, and I hadn't yet sampled any night life. I was too tired to wander far, so I left my suit jacket in my room, and took the elevator to the lobby. I was wearing a white blouse that looked like a man's white shirt, and like one was made from fairly thick cotton. My skirt was black, and pleated so that it moved easily. It was cut about four inches above my knees.
The lounge was quite large, but lit fairly dimly. Along two walls were circular booths that were very private because of their high backs and the low lighting. There was a small dance floor off to one side, also dimly lit, and a bar ran along most of one wall. Most of the booths were already filled; some people were up dancing to the fairly loud music, and about half the stools at the bar were filled.
I took a stool in a cluster of empties. The bartender came along right away. She was a cute young blonde wearing a very short skirt, and a vest that was held together by one clasp under her breasts. There was enough space between the sides of the vest that the inner curves of both breasts were visible. She was well supplied in that department.
"Hi. I don't think I've seen you before. What can I get you?"
"White wine, please. And, no, I've never been here before. I'm just in town on business, and I'm staying at the hotel."
"Oh, in that case, the first drink's free—hotel policy. And since you're staying at the hotel, I can start a tab for you, and charge the rest of your drinks to your room."
Before I could respond, a voice beside me said, "Not necessary. Put that and anything else she wants on my tab."
As I turned to look for the source of the voice, I noticed that the bartender's expression seemed to switch to something like disappointment as she said "Yes, Cynthia."
I looked into the newcomer's cold green eyes, and noted the flaming red hair and a scattering of freckles across the bridge of her nose. "So, if I heard right, you're a virgin."
"What makes you say that?" I asked, thinking "That was kind of rude."
She stared intently at me for a moment, sweeping her eyes over me, then said, "I meant that this was your first time in here, but since you asked, I'd bet that you were on the cheerleading squad all through high school and college, and I'd say you haven't gone beyond fumbling around in the back seat of your high school boyfriend's car. You may have let him feel your boobs, but I'll bet you never went beyond a handjob or two 'to keep him from getting hurt.' And I'd further bet that you've never had an orgasm caused by someone else, just your own fingers under the blankets late at night. I'd also be willing to throw in that when you looked at the rest of your cheerleader friends naked in the showers that you felt funny in your stomach, and didn't know why."
My mouth dropped open in absolute shock. Cynthia picked up her drink and took a swallow, all the while staring intently at me. I couldn't breathe for a moment, then tried to cover my shock by taking a sip of my wine.
Cynthia leaned forward, and dropped a hand to my thigh, resting it on my skirt, then squeezing lightly. "So, cheerleader, how would you like to rock your little world, and break out of your shell?"
"What do you mean?"
"Ever play 'Truth or Dare' in White Bread, Kansas?"
"My town wasn't called 'White Bread', and yes I played 'Truth or Dare'? What of it?"
"Okay, I would imagine that if you ever went back on a dare, you were pretty much ostracized by all your friends, and became the butt of all the jokes, right?"
"Yes, that's true. That's one of the reasons why I gave Bobby Wilson a handjob. I got dared, and if I hadn't followed through, I wouldn't have been able to show my face at school."
"All right. For the rest of the evening, whatever I tell you to do, you have to treat just like we're playing 'Truth or Dare', and you're being dared. You have to just do it, and not ask questions, unless you don't understand what I've told you. Agreed?"
I took another swallow of my wine before I answered. I don't usually drink much, and I was already starting to feel a buzz. Maybe that's why I agreed, or maybe it was because of the way my stomach had clenched when she talked about a series of dares. Quite frankly, playing that game had always scared me, and here I was agreeing to do it in a public place with a perfect stranger who said she was going to 'rock my world'.
"First dare starts with a question: are you wearing a bra?" I nodded. "Take it off."
I started to turn to get up and find a washroom when her hand tightened on my thigh. I looked into those cold green eyes as she said, "No. Here."
"You want me to take my shirt off here? I'm not saying no, I'm asking for clarification."
"Well played. No, slip your bra off through your shirt sleeves. Surely you've done that before."
I nodded, and said "Can you undo it if I turn around?"
"Sure, spin around."
She deftly unhooked my bra though my shirt, and I proceeded to work the straps down and out through my sleeves, ending with my bra in my lap, in stark contrast to my black skirt. Cynthia reached out and took it, saying, "That's mine for the evening, so you won't get tempted to put it back on." As she folded it, she looked at the size tag and saw that I wear a 34-C. "A C-cup, eh? Are they a full C, or on the small size?" She finished folding my bra, and stuffed it into her bag.
"They're a full C-cup. If I'm on my period I have to let my bra out a notch or two."
"Good. Are they pretty?"
"Yes, I think so."
"Show me. Unbutton your shirt. Slowly"
I swallowed hard, but instead of running away, I looked around and realized that no one seemed to be watching us. I started slipping buttons, one by one. I kept waiting for Cynthia to tell me to stop, but she said nothing, staring intently at my fingers. The hand on my thigh squeezed in encouragement.
When I reached the waistband of my skirt, I moved my hands away, but she gestured for me to pull the sides of my blouse apart, "I said to show me. I can't see anything unless you open your blouse."
Glancing around again, I slowly pulled the sides of my shirt apart, trying to avoid pulling it out of my skirt. As I felt the sides drag over my nipples, I realized that they were very erect. I stopped as soon as I knew my nipples were pointing out into the open. After a second or two, I started to move my hands back together.
"Stop. I haven't given you permission to cover up yet. You're right, they are very pretty, and look quite firm." Cynthia's hand moved into the opening of my shirt, and cradled my right breast in her palm. She lifted it a little, as if weighing it, and then squeezed it, gently at first, then more firmly. As shocked as I was, I couldn't help the ragged breath and low moan that came from my throat. As she fondled my breast, she looked up from it to my face, and stared into my eyes once again.
"You must be very proud of these. They're magnificent. Are they sensitive?" As she said this, her hand moved to the front of my breast, and she took my stiff nipple between her thumb and index finger. She rolled it back and forth, squeezing a little.
I moaned again, louder this time, and a little band of sweat broke out across my upper lip. Leaning closer, she wiped her tongue across my lip, tasting my sweat, and then kissed me as I moaned again. Her tongue invaded my mouth, probing deeply and touching my own tongue. She increased the pressure on my trapped nipple, squeezing harder and harder, and rolling it forcefully back and forth. It felt like she was going to twist it off, but at the same time it sent a massive jolt through my breast, and down to my groin. I was moaning continuously into her mouth, both fearing the pain and reveling in the pleasure that was coursing through my body.
She finally pulled back, and let go of my nipple, but moved her fingers to the other one. As she started to torture it in a similar fashion, she smiled at me and said, "Have to make sure that everybody gets equal treatment, or else it's not fair." She stared into my eyes as she kept up the harsh treatment of my poor little nubbin, then finally released it and gave my left breast a firm squeeze. "God, you've got great tits. I can't wait to get you alone so we can see what they can really take ... but in the meantime, I think I have something."
She opened her bag and rummaged inside for a moment, muttering to herself. Finally she came out with something in her hand, and motioned to me to lean closer. She startled fondling my right breast again, playing with my nipple. In the next instant, I felt something metallic on either side of my nipple. I looked down, and there was something like a pair of tweezers dangling from it.
She reached for the other nipple, and repeated the process. Next, she started sliding some kind of adjuster up the tweezers, and I could feel the pressure on my nipple increasing. It soon started to hurt, and I whimpered a little. Looking up at me, she said, contemptuously, "You can take more than that. These are only starter clips. Wait until I use the real ones."
At that, she tightened the clip even more, causing my breath to hiss between my teeth from the pain. Then she moved to the other nipple, and I hissed again. When she moved back, I realized that there was a chain connecting the two clips. She hooked finger in it and pulled me towards her. She laughed lightly and said, "There, now I have some control."
"Please what? Please you want some more?"
"Please could you take them off, or at least loosen them. They really hurt."
She tugged the chain, pulling my nipples out by the clips, and increasing the pain markedly. I whimpered again. "You didn't ask me nicely, so you'll have to wear them for a bit longer. Besides, I like the way they look on you.
"Now, what's next? Oh, yes. Let's see what you are wearing under your skirt? Pantyhose, or stockings?" With that, she put her hand back on my leg, but this time by the hem of my skirt. She slid it under the skirt and over my stocking until she reached the bare skin at the top. Smiling, she moved her hand between my thighs and cupped my mound. I realized that I was soaking wet, and so did she.
Her fingers pressed inward on my panties, forcing them into my wet slit, and rubbing back and forth. As she reached my clitoris, she pressed hard, and slid her fingertip back and forth over the button. My breathing turned ragged, and I began to fear that she probably wouldn't be above making me come right here. Then suddenly, she withdrew her hand, and stopped.
"Stand up, let's get those panties off. They're soaking wet anyway, so you must be uncomfortable."
I slid off the stool, and stood in front of her. Without saying a word, she simply reached under my skirt to my hips, grabbed my panties, and pulled them to my knees. I closed my legs and felt them drop to the floor.
"Well, pick them up. Give them to me."
I stooped to obey, and felt her hand on my head. I looked up, and she said, "Kiss my knees." After a moment, she spread her legs open and said. "Stand up between my legs, and give me your panties."
I moved into position, and placed the warm and wet panties into her hand. She wrapped her arms around me, and pulled me in for a long, deep kiss, her tongue seeking the inside of my mouth and fencing with my own tongue. One of her hands moved behind my head to hold me in position, while the other suddenly tugged the chain between my breasts, forcing me in tighter between her legs. The hand on my head slid down my back to my ass, and started rubbing through my skirt. In a moment, I could feel my skirt rising in the back as she pulled up on it, finally baring my ass to her hand. She squeezed my butt, feeling it move beneath her fingers.
"Hmm, nice and firm as well. It must be all that cheerleader training. All those high kicks. I think we should have a dance or two, but first I think you need some new accessories." She reached back into her bag, and came out with a few pieces of leather. "Give me your hands."
She wrapped something that looked like a leather bracelet around my left wrist, closing it with a Velcro strap. She tested it to make sure it wasn't too tight, and then did the same to the other wrist.
Taking each of my arms in one of her hands, she moved them behind me, and brought my wrists together. I felt a click, and she released my wrists. I started to move them forward again, and realized that they were locked together. I looked at her in panic, but she put a hand on my cheek, and said, "There, there, little one. Don't be afraid. Nothing harmful will happen. It's all part of rocking your little world."
She reached for the remaining pieces of leather, and moved her hands to my neck. Before I could comprehend this next step, she had wrapped a collar around my neck, and snapped a dog leash to a ring in the front. Stepping back, she looked me up and down, and reached out to my still opened shirt. Pulling it free of my skirt, she unfastened the remaining two buttons, and arranged it do drape exactly over my clamped nipples. The friction on my hypersensitive nipples was almost too much, but then she picked up the chain and slowly pulled until it was horizontal and my breasts were following my nipples, being extended into a cone shape. This caused the side of my shirt to open further, now fully exposing my nipples with their adornments.
This must have been the look she was after, because she grabbed my leash, and started heading for the dance floor. I didn't start moving, and she turned to me with a glare. "Either you come along nicely, or I'll get some nastier nipple clamps, and use those for the leash."
We proceeded to the dance floor, and once we arrived at the middle, she enfolded me in her arms, and started to move in time to the music. As she held me tightly, my nipples were sliding over the material of her dress, sending a series of shocks to my groin. Her lips moved to mine, and she started kissing me deeply, her tongue going into my mouth, then back to lick my lips.
I could feel her arms pulling my skirt up, and soon she was cupping both my buttocks in her hands, rhythmically kneading them in time to the music. My hips started moving in and out, as the pressure of her hands pulled us together, then moved us apart. My desire kept building, especially as I had no idea where this was heading.
Unexpectedly, she drew back, and allowed my skirt to fall. She spun me in her arms and then drew me back in, so that we were now dancing facing in the same direction, with her behind me. I could feel her hands moving behind me, and I thought at first that she was going to release me from my bonds.
After a moment, I could feel bare flesh, and I realized that she had rucked up her dress in the front. Moving tightly up behind me, my bound hands were now squarely on her mound, which felt completely smooth, and I realized that she must be shaved.
"Rub me. Make me come. Do it or your tits will feel it."
Fearfully, I extended my fingers and pressed back, finding her wet slit, and sliding two fingers up and down its length.
Her hands came around my waist, and moved upward to my breasts. On the way, she jerked the damn chain again, then continued upward until she had each of my breasts in one of her hands. She started massaging them painfully, squeezing and moving them around. It felt like she was trying to tear them off. The constriction of my breasts caused my nipples to swell, awakening the pain, which had dulled down to a low-level throb. Now they flared into life again, sending sharp pains into my breasts, and causing my groin to pulse with their flashes.
Her hands finally left my breasts, and moved to my hips. When I realized that she was pulling up the front of my skirt, I stopped rubbing her pussy, and started trying to pull away. Her arms pulled me back with surprising force, and she said, "Remember, you're supposed to go along with everything I say. You aren't going to be hurt, but I might have to spank you if you don't comply. Now, get your hands back in my pussy. You were just starting to get the hang of it. You let me worry about what happens to you, and especially your corn-fed mid-West puss."
With that, she started pulling my skirt up again, and I knew I wouldn't be able to stop anything from happening. I moved my fingers back to her clit, and resolved to bring her off as quickly as I could, since that might end this ordeal sooner.
As the hem of my skirt passed my crotch, both of her hands moved to my groin. When she discovered my pubic bush, she tugged on it and said in my ear, "We'll have to get rid of this later." I blushed at that, which surprised me since I hadn't blushed about anything else on this strange evening. Her hands moved lower, and she used her middle fingers to split me open, and then attacked my clit with her index fingers.
Her fingers moved in rapid flurries back and forth across my clit, battering it from side. At one point, she used her thumb to hold the hood out of the way, and scraped across my clit with her fingernail. The sudden, quick flash of pain to my pussy was all it took, and I started to come. I should have been hugely embarrassed, but I was beyond caring. My hips set up their own musical beat, I was groaning continuously, and started to wail loud enough to be heard over the music. Cynthia kept one hand in my pussy, madly rubbing over my clit to prolong the orgasm, and moved the other arm to hold me up while I flailed in the throes of the orgasm.
After a moment, I went limp in her arms, and she struggled to hold me. A woman who was just coming onto the floor with her partner came to her rescue, by helping to hold me up. She slipped an arm around my back, under my bound arms, and helped to hold me erect. Cynthia still had a hand in my crotch, and of course my breasts were bare for all to see. The other woman looked me up and down, and said, "Damn, Cynthia, you sure know where to find them. She's absolutely gorgeous, and she comes like a banshee. Who is she?"
"She's pure Kansas-grown, corn-fed cheerleader. I think that was probably the first real orgasm she's ever had. Go ahead and feel those tits, or take a taste."
The other woman reached over to my breasts, and palmed each one, giving them each a firm squeeze. Of course, she gave the damn chain a tug, and then moved her hand to my pussy, where she slid two fingers into me for a moment. I was still in the aftermath of the orgasm, so this set off a few pulses deep inside me. After lingering for a moment, she withdrew her fingers and raised them to her mouth where she licked them all over, then slid them into her mouth to get the final drops of my juice. Taking them out, she looked at Cynthia. "You're right. She's as sweet as they come. Absolutely delicious. I envy you."
After a moment, I recovered enough to stand up, and Cynthia started walking me off the dance floor back to the bar. She stopped to drain her glass of wine, and picked up her bag and my purse. Turning to me, she grabbed the end of the leash and started walking.
"Where are we going?"
"Your room. We've got some unfinished business to take care of."
I started walking after her. "Unfinished business? What unfinished business?"
She moved up beside me, and licked my ear. "For starters, my unfinished orgasm. You got to come, but I didn't. I guess I'll need to teach you how to eat pussy so I can get some satisfaction. And if you're a really good girl, I'll take those clamps off and fuck your brains out with the strap-on I've got in my bag."
We headed for the elevator, and the rest of the evening proceeded in exactly that manner. When we got to my room, she threw me on the bed on my back, took her dress off, and straddled my face. Holding me by the hair, she growled at me to stick my tongue out and get to work. She used my hair to move my head to where she wanted the most pressure on her clit, or to deepen the reach of my tongue into her snatch. Once I got the hang of it, I realized that I actually liked her tangy taste, and I learned that my teeth could be used to scrape her clit gently, or to clamp her inner labia while I tugged a little. She came at least three times, riding my face into the mattress. When she finally threw herself sideways off my mouth, my hair was soaked, and my face was covered in a sheen of her juices.
After a bit, she roused herself and said, "You've done that before, cheerleader. Don't lie to me or I'll tan your cute little butt."
"Honestly, I've never even kissed another girl. I've done more things with you tonight than I have ever done in my life. You really have rocked my world, and my head is still spinning. Could I maybe ask you a favour, though?"
"What's on your mind? After the way you ate me, I'm feeling charitable."
"Could you maybe lick me the same way, so that I can feel what it's like?"
"Oh, I think I could maybe do that, but first there's something else we need to do."
"What's that? Is it maybe taking these damn nipple clips off? Or untying me?"
"Nope. I don't mind licking your little corn-fed puss, especially since I know it tastes really good. But I refuse to eat pussy that's furry, 'cause I can't stand pulling hairs out of my teeth."
With that, she moved to the bathroom, and I could hear her rummaging through my stuff. In a minute she returned with a wet washcloth, a pair of scissors, and my razor and shaving gel. She spread my legs wide, then got between them and started snipping away at my bush. In a minute or two, all I had left was a crew cut. She used the washcloth to wipe up the left over hairs, and to soften the stubble, then spread shaving gel all over my mound.