***
I begged out of work early, making up some errands I needed to run. The same woman who commented before, Susan, grinned as we passed on my way out. Pitching her voice low, she said, "Karen must be worn out- look at how you fidget after just a couple days. Have fun!" Susan was usually a staunch ally, a buddy in corporate trenches, and still she managed to make my blush flare up. I was going to get a reputation if I didn't learn to think on my feet regardless of whatever distraction Jan was lobbing at me.
The rest of the trip was uneventful. Knocking at her door, I heard her call me in. She had drawn down heavy curtains, plunging the room into night like darkness, broken by a couple of soft lights. She walked into her living room, a large robe cinched around her, hiding whatever- if anything- was underneath.
"Oh, darling. How long do I have you? Be honest."
Taking a breath, I admitted, "The rest of the day. No one expects me back and..." I trailed off. I couldn't believe I was saying this next bit, "Karen is busy and probably thinks I'm working." Her face lit up. She led me about, not making any reference to why exactly she was wearing the robe. Before I knew it, she was bombarding me with small talk, once again pretending that absolutely nothing had happened. This time the anxiety and fear- and if I'm being honest hunger- kept me on edge. After a few minutes, she declared that I was far too tense and she had the solution and disappeared into her bedroom. She trotted back in with an ashtray, a grin, and what I'll euphemistically call a hand rolled cigarette.
"You are such a sucker." Her face was filled with genuine amusement. "You thought you were so totally fucked, didn't you?" She lit paper cylinder and passed it to me. I shook my head, confused. "You don't remember, do you? Last Halloween?" I hung onto the joint, mind racing. I had no idea what she was talking about, my head shaking out a no as I tried to remember. "Halloween. I had the pitchfork?"
"The only thing I remember about Halloween was my hangover." This seemed to amuse her even more. She moved my hands up to her lips and took a very small puff.
"Oooh. You were being such an asshole. You were in a mood, all big man-y." She pulled her hand to cover her mouth as she excitedly proclaimed, "Which also means you don't remember the bet." I had been lost, hanging onto a plank in the middle of a raging ocean and suddenly there was a light on the horizon. My head continued to rattle out its little back and forth no while I prepared to leap to whatever this tiny sign of safety was. "Long story short, it was a hundred bucks that I could get you into panties before the year was over because women are the superior sex." She leaned in to my ear and whispered, "The other stuff... that was just booze and going too far. You don't tell, I won't."
This was it. I was free. My chest was suddenly light again. I took a deep hit, let the relaxation flow over me. It was over. I tried to ignore how quickly the bulge in pants- in my panties, really- deflated because, so unexpectedly, I was free.
***
"The thing is," she said an hour later. An hour of me letting out all my tension, relaxing into an intoxicated state. I was floating, but I was in no way out of control. I don't get any excuses. "The thing is," she repeated, "it did happen. But it was a bit one sided. And that isn't fair. And the girlfriends' club really is a thing." She stood up, finally shedding the robe. Under it, she was wearing some kind of corset that gave way to a diaphanous little skirt. I can try to pretend it was my lowered inhibitions, but I knew what I was doing when she put her hand in my hair and used that grip to guide me to the couch, where she settled down comfortably, pulling me between her thighs.
She didn't have to tell me what to do; I just started kissing my way along her thighs. She slid them slowly wider as I kissed, a lttle tease of tongue. Paying attention to each inch forward. This wasn't new territory for me, after all. Unless she had changed significantly in the intervening years, I had a very good idea of what she wanted and how to give it to her. When I breathed lightly over her sex, she inhaled sharply. When I lightly kissed the close shaven, soft skin around the little strip of pubic hair she maintained, her hand gently clenched an unclenched. Some things don't change. My tongue had just parted her lips, tracing out an incredibly light pattern as a way of saying hello, when she pulled my head back a little.
"This is about me, girlfriend", she said with almost a sneer, I thought. "Take off your shirt. I want to feel your shoulders against my thighs" I quickly shed my clothes, no thought of resisting entering my head, but when she gestured to my pants, I paused. "Oh! Oh!" She was joyful again. "You're wearing them. Pants, too. Show me." I was frozen. I couldn't do this again. Could I? Her eyes narrowed and she stuck out her phone, turned to me. I expected to see a still of me from the video, but instead it was a conversation with Karen.
Janice: Guess what I'm doing?
Karen: Robbing a bank?
Janice: Guess again!
Karen: A football team?
Janice: Close! I'm getting a tongue massage and texting about it. It's lady day!
Karen: Show off! Who? Who?
The threat was obvious. I exhaled, closed my eyes and kicked off my shoes and socks, followed by my pants. I was trying to be as utilitarian as possible. I opened my eyes when I heard her giggle. I followed her gaze down and saw what had her attention: my cock was hard, sticking out of the panties she had put me in, but the panties themselves had a wet spot, remnants of my early excitement. She leaned back and struck a pose. I just gave in went to my knees, tongue returning to its previous work.
I became lost in the experience, as I almost always did. Making a woman moan and scream with my tongue is one of my favorite things and I think that appreciation shows. Jan's increasing squirming, thighs regularly clenching against my ears, and her hand snaking in and out of my hair. After a few minutes, she first pulled my face hard into her and then pushed me away again, panting. My cock had been hard throughout, not softening as I focused on her. I could feel the line of precum dripping off it. I went to stand up, but she caught me. "More. Again."
I started over again, beginning on her other thigh this time, a mirror of earlier. I'll admit it, I was taking some satisfaction in making her squeak and jump, perhaps teasing her too much. But in my experience, "too much" teasing often leads to an incredible finish. I had been lapping at her with a slow, steady pressure when she pulled my head back again, panting out, "Read."
Janice: Newest member of the girlfriends' club.
Karen: You're the worst, the absolute worst. Is she any good? Does her guy know?
Janice: Yes. He's learning all about it. You know, you haven't paid dues lately.
Karen: The worst! Beyond the worst! You know why.
Janice: Fine, the new girl can pay your bill. :P
Karen: Haha! Oh my god! You're doing the Miss Janice routine, aren't you?
"Did you see that? Karen says 'she'. I mean, you're in the club and have panties. We'll have to think about that." Her words just ran over me, forgotten the moment they hit my ears. What did she mean, "lately." Had Jan been serious with her innuendo about Karen? And Miss Janice? Where had this woman been when we were dating? She was always sex positive and adventurous, but this? All this? And my Karen had known? She used her grip on my hair to guide me back down to her, my tongue seeking resuming its work almost automatically. Karen had known?
"Faster," she barked. I could hear her tapping her phone when her thighs weren't muffling all sound around me. I could only imagine what danger she was adding to my life with each stroke. I desperately tongued her, my fear and excitement keying me to follow her every little cue, the way she shifted and moaned, trembled and clenched. Finally she clamped down on me again and then I felt her go completely limp. Her hand lazily drifted up and patted me on the head, "Good boy." She seemed to reconsider, "Good girl." I went to straight up, face going red, and her hand clenched around my hair. Her other hand pointed down at my still hard cock, at the pile of precum below me. "You enjoyed that. Stay here, don't move. I want to show you something." She paused a moment, "Put your hands behind your back; I don't trust you."
She stood and walked to the bedroom and my eyes followed her. She was a beautiful woman, but I realized that it wouldn't have mattered, what was holding me here was that sense of perfect control. She could have been thirty years older, twenty years younger, any shape. It was the confidence that was holding me. Well, that and the suggestion of blackmail. It was all melding together, anxiety, fear, excitement, need, and my bobbing cock wasn't helping.
"Eyes front," she ordered. I snapped my head back from where it was turning to track her return. More importantly, I did it without thought. I needed to get out of this. I couldn't get out of this. A moment later, I knew what it really felt like to be literally locked into this path. Yes, you probably guess it; she cuffed me. She was quick and methodical about it, as if she had trained not only in cuffing people, but cuffing resisting people. I didn't resist, though. Let's not kid ourselves, those cuffs were doing nothing to hold me in place. They were just another symbol. Like my cock in panties. Like the pictures. Like the video. A symbol of what she wanted. Of course, I had no idea how far that might go. Hell, I didn't even know how today was going to end because I would have never been able to predict it.
She dragged two little padded footstools over, sitting on one and pushing the other in front of me. She gave me a smile, fiddled with her phone and then presented a picture of a pair of handcuffs with a soft lining against the inside of the metal. They clearly weren't just for show. The picture was titled 'A'.
"Karen picked these for you! She wanted you all tied up and unable to stop whatever happens! Can you believe that?" She pushed me over, leaving me bent across the foot stool. "Now I can do whatever I want, like this!" She reached out and wrapped her hand around my cock, below the head. She just rested it there a moment, as if weighing me, then she pulled her hand up and coated it in the copious precum that had been drizzling for what felt like ages. My eyes slipped shut as she began to stroke me. She had always been an expert with my cock, always seemed to have an intuitive sense about it. She would often tell me that it was perfect for her to play with, always mentioning that it wasn't too small, but then with a kind of half smile telling me that it wasn't too big. Here I was, bent over, cuffed, pantied, and still her hand was all I could feel, all I could focus on. Her strokes were long and slow, her hand occasionally going down to caress my balls. It didn't take very long before I was completely lost to her. I was sober. I was aware. I just wanted to be... I'm not sure. Possessed? Used?
"She picked out a second thing, too! Plus backup, if that's not enough. How thoughtful was that? You should say thank you." I kept my eyes closed, lost in her hand. Her other hand brought me to my senses, slapping down on my ass. "You're not very respectful of her, are you? We're going to have to change that." The hand on my cock went into overdrive, twisting and tugging. If she continued at that rate, I wouldn't last long. Until her other hand come down on my ass, again. I yelped and twisted. I have no idea why I was silent. Somehow, if I didn't talk, it wasn't real. She swatted me three more times, then repeated, "You should say thank you."
"Thank you! Thank you, Jan!" Her hand came down again, the stinging layering on top of the burning that has already spread across my cheeks. The hand on my cock slowed.
"So disrespectful. Thank Karen." She twisted her hand on my cock, punctuating Karen's name with an intense spike of pleasure.
"Thank you, Karen," I blurted out, "Thank you for the cuffs!" And had a genuine wave of thankfulness spread through me, endorphins raging away wildly. My ass was hot and my cock felt like a heavy lead bar to me, and I was certain I was going to start trembling at any moment.
"That's better," she cooed. "Good girl!" She punctuated the girl with another twist. If she kept making me feel that spike of pleasure, she was going to have me begging for it. "I bet you're dying for her other present, aren't you? Hungry little thing like you?" She moved behind me, out of sight. I heard her rustling around and then the top pop off what sounded like a bottle. Soft, wet sounds drifted out. "I was actually pretty surprised about her choices. They went a bit further than I expected." I felt her move close to me and she reached down, between my legs from behind. She used her arm to nudge my legs apart as her hand once again wrapped itself around my cock. It was incredibly slick, coated in a lubricant. I groaned at the new sensation, which earned me a chuckle and her arm spreading my thighs more. She could easily hold me in place with a hand on my back, now, if she wanted.