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.
.... There is more of this story ...