Sports Night With the Guys

The look I gave her was one of mild surprise. "What are you doing here?" I said. She smiled as I pulled on my drink.

"Your wife told me where to find you, Raymond."

"My wife wouldn't tell you jack squat, Jan. She knows about our history." Her smile grew wider.

"She didn't realize what she was telling me at the time, hon." Jan had never been given to alcohol, so she sat with her 7-Up, sucking on the straw and eying me playfully.

"You tricked her?"

"Mm hm."

I looked for the bartender, somewhere between ordering another whiskey and closing out my tab. Then I looked at Jan. She wore a dark blue one-piece skirt cut mid-thigh, showing off not only her divine cleavage but her firm legs. A few pounds heavier than when I'd known her in high school, her fitness kept her legs nicely toned. Toes painted red stuck out through black sandals with a three-inch heel. Or maybe it was four. I felt my groin stir. She watched me watching her, and her smile widened.

Tuesday night was sports night, a mid-week refuge my wife and I had agreed upon to keep televised games, along with my beer-guzzling friends, out of the house. The bar was on the bottom floor of a downtown hotel. Jan had long considered me unfinished business, partly because I'd gotten her pregnant but bailed before we could tie the knot. Whether revenge or unfinished business, I could not be sure. Now happily married to the sister of my first wife, I was not about to cross any lines.

"Where are your friends, Raymond?"

I shrugged. "I guess I got stood up. Rob had something going on, Randy had to work late, Brian? I don't know."

"I see." My eyes followed her hand as it went between her inviting boobs, boobs I had years ago sucked and licked and covered with slobber, the memory of the taste and feel not having dimmed with time. She removed a plastic room key that resembled a credit card, laid it flat on the counter, and slid it to me. "Room 248. I'll be there for the night."

I placed my hand on the back of hers and slid the key to her. In a flash, I remembered fucking her doggy-style, the way our hands now were. Our eyes met, and in them I saw she had the same memory. My heart jumped ahead.

"Jan, I can't."

"Sure, you can." She pushed the key back to me, our hands holding the suggestive position. Her eyes held mine the way a snake stares down a bird. "Through the elevator, turn right, halfway down the hall." She stood, exposing the naked flesh of her legs, my eyes coming to rest on her ankles, toes, the arches of her feet. My eyes followed up her legs, pausing at breasts that were now inches from my face. Her lips were shiny, full, inviting. "No one knows your kinky side better than I do," she said in a whisper. "See you upstairs."

"No, wait." But it was too late. She turned and walked toward the lobby, her hips swiveling seductively, with my eyes in tow like a fish hooked to a line. I ordered another drink and settled my tab, remaining on the stool while my mind ran through a hundred excuses to give my wife. I had a flat tire, or I got too drunk to drive so I stayed overnight, or an old friend dropped by and we lost track of the time. None of them worked. Melissa wouldn't buy any of them. Even the best would earn me a long trip over her knees or a discussion with her leather belt. But the excuses kept coming. I was no match for Jan and both women knew it. What Jan had to offer was at least as good as what I had at home. Dammit.

I slid the card into the lock and watched as the light flickered green and the latch made a snick. I gave the door a nudge and watched it open. Facing me from the middle of the room, Jan was standing, her hands behind her back.

"I knew you would show, Raymond. Come in. Close the door. Would you like a drink?"

"No. I'm not staying. I have to—"

"Sure you are, Raymond. You wouldn't have come here just to tell me no. Remember, I know you better than Melissa knows you. I know what you like and how much you like it." She brought her hands before her. In her right hand was a leather strap. Her smile was back. "We're going to have fun tonight, Raymond. You and me." She took a step toward me and I held out my flatted palm. She stopped, cocked her head. "Hard to get. I like that in a man. Always have," she said with a wink.

"Seriously, Jan. You have no idea what Melissa will do to me."

Jan laughed. "Sure I do, Raymond! You forget who you're talking to. She'll beat you until you bawl like a baby, probably leave you tied to something heavy in a dark room. Does she put your cock in a cage, silly boy?"

"I—how did—"

"Raymond, my love, she needs those beatings as much as you do. I need them, too."

I gave her a funny look.

"No, not like that. Some women need to beat men, even beat other women. We crave the power in the same way you crave giving it to us. Yes, that's right. And you thought you were in a minority, a secret society of submissive males? Tsk tsk tsk. Not a chance, honey." She eyed my waist. "Has your bottom healed up from her last whipping? Mind if I see?"

I felt myself weakening as the power to resist began to fade.

"I never should have come here. You're going to wreck my marriage."

"Nah. I wouldn't do that to you, even if you did leave me at the altar." Her demeanor began slowly darkening as the power shifted to her. We both felt it. "I do plan to do serious damage to parts of your body, but your marriage I will not harm. Remove your pants so I can see how your wife has been treating you."

"Really, I don't think—"

Her eyes turned cold. The hand with the strap came up, stopping in plain sight of us both. "Remove your clothing, Raymond. Now."

Slowly and reluctantly, I toed out of my loafers, removed my shirt, and began to undo my own belt, stopping at her words.

"I should whip you with that," she said. "Maybe I will."

After a shaky sigh, I slid my pants down to my knees, then pushed them to the floor and stepped out of them. My cock was fully engorged but still hidden behind my boxers, earning a brief smile from her.

"Slide those off, too. There. Good boy." Eying my stiff cock, she said, "I see you still respect me, Raymond." Her fingers closed lightly around my cock and she began to work it slowly, down and up, down and up. I could feel my dick throbbing, aching for release I knew would be a long time in coming. A very long time, if she granted me the privilege of cumming at all. If she didn't, I'd have to jerk off in the car on the way home, whenever that might be.

As I stood naked before Mistress Jan, I worked to push away thoughts of my wife. I began to tremble in anticipation of Jan's fury, though I doubted she could see this. Jan had always enjoyed giving a whipping, doling out pain the way some people give out candy at Halloween. She prided herself on denial and mastery, demanding servitude, demanding to be worshipped. She knew my weaknesses the way a mechanic knows which spark plugs to use.

"Your bottom looks like it's healed up from your last punishment." She smiled. "I like to think of it as a canvas, my implements paintbrushes. It's a fitting analogy, don't you think?"

"Yes, ma'am, fitting indeed." My words were robotic, my voice weak.

Jan turned away and stepped toward a table, and after removing a wooden hairbrush from her purse, she removed a chair and sat on it. She motioned to me by crooking the index finger of her spanking hand, the one with the wicked hairbrush.

"I think I'll warm up those buns of yours, Raymond. Lie across my lap. I know you do this for Melissa, don't you?"

I approached her timidly, meekly taking the position she had ordered. "Yes, ma'am."

"Yes, ma'am. I have trained you well." In her voice was a smile. Her right leg came down across my thighs, holding me in place with the added weight.

"Yes, ma'am, you have."

"You remember well how I insist on respect. Good boy."

"Yes, ma'am. I remember to always respect you, Mistress."

"Now, for your initial trip to the penalty box, I sentence you to one minute."

"One minute?"

"Yes, dear. I like to spank in even, measured strokes, once per second. Rather than worrying about sixty and a hundred-twenty, I just think of one, two, three."

"I see."

"You will." The brush came down without warning and made a loud cracking noise that startled me as much as the pain. Crack, crack, crack, Jan alternated cheeks, expertly hitting her bullseye in the center of each. I saw the shadow of her arm reaching high up on the wall, felt her weight shifting with each spank. Tears began to coat my eyes and pool in them, but I closed the lids and squeezed down hard. She loved the sight of my tear-stained face, and I knew she was liable to keep spanking me until she saw it. But it was early, and she had a long time to achieve whatever results she desired.

The paddle finally stopped. My bottom glowed warmly. Jan brushed each cheek lovingly with one soothing hand, relief that would be short lived.

"Oh, Raymond. That felt so good. When was the last time I gave you a good paddling? Has it been ten years already?"

My breathing steadied and she motioned me to stand, which I did. My cock was no longer offering her the salute it had earlier. But the night was young, and as soon as the pain subsided, I would be respecting her with a stiff dick.

"Yes, ten years," I said.

Jan stood, then retrieved something from the table, and fastened cuffs onto each of my wrists. Then she slipped a collar around my neck.

"Ah, my pet. I have longed for this day," she said dreamily. "It's going to be a lovely night, don't you think?"

The fear in my eyes was all the answer she needed to hear.

"You know, I should call Melissa. Then we could take turns spanking you. I could give her some pointers, maybe lay my strap across her ass too." Jan and Melissa had remained friends through my divorce and remarriage, though they had not been close since our high school days together. Melissa rightly recognized the threat Jan had posed to our marriage. I feared Jan's beatings, but I feared more the awful thrashing I would get once I got home and my wife found all this out.

"Please don't whip me. I beg you."

"You'll have lots of time to beg me, Raymond. Save your strength. Now, come." She led me to the foot of the bed, pulled my hands to the floor, and instructed me to kneel. Then she looped the restraint where the bedpost met the floor and fastened the cuffs together. From this kneeling position, with my face low to the ground, my ass poked up nicely for her to spank.

"This is an excellent position for a long, hard whipping, don't you think?"

"Yes, ma'am." I watched as she wiggled out of her dress and let it pool around her ankles. I struggled to recall why I had left this sexy woman. Stepping out with her delicious heels, she brought her toes to within inches of my face.

"I know how much you love my toes, Raymond. You always have. Do you remember the taste?"

"I—I think so."

"Think so?" She produced a camera phone and began snapping pictures to further humiliate me. "You must remember, silly boy." Another few pictures, and she reached down to slip out of her shoes. Then she brought five toes to my lips. "Lick. See if you remember." I did as I was told, clearly in no position to do anything but please her in any way she wanted. "That's right. Oh yes. Good boy. Between the toes, yes like that. Mm. You do remember. You have no idea how happy this makes me."

I continued licking her toes for a while, and then she changed feet and I serviced five more toes.

"There will be lots more of that, my dear, don't you worry. Now, do you remember how your first wife used to spank you barefoot?"

"How did—"

"Women talk, silly man. Oh yes, her balance was so much better once she got out of those heels and she could really bring the belt down hard. I taught her that, did you know? See, we women use sexy footwear to lure you in, then we control you with our pretty feet and our pretty boobs and all our lady parts." I craned my neck upward to see her wide grin. "We only let you males know what we want you to know. You're useful to us." She hesitated. "Do you know I once changed the sexual orientation of one of my old boyfriends?"

"What? How on earth—"

"See, cocks are actually quite enjoyable. Giving a blow job can be—"

"You're crazy. I'm not going to do anything like that."

"You just added a minute to your penalty, dear. Would you care to try for two?"

"Not especially."

"Then do not interrupt me again. Now, where was I? Oh yes. Dominic was my boyfriend after you. We were together for about a year, and then sex got boring, so I decided to spice things up. I invited a girlfriend over for a threesome, and then a guy I knew from work."

"A threesome with two guys?"

"Yes. If you can have two women, we can have two men, can we not? Well, we did. I made Dominic suck a dick."

"Not a chance."

"Yep. He didn't like it at first, but I eased him into it, showing how it was done, how a penis can be like any part of the female anatomy. I got him used to kissing me with Sandy's dick in my mouth, then we took turns licking the shaft, and finally Dominic took Sandy's dick all the way. He even swallowed him once."

"You're kidding, right? What's this got to—"

"Not kidding at all. Now Dom swings both ways. I have his number. We might have to have our own threesome tonight."

"Untie me this instant, you crazy bitch." The air left the room after I spoke the words. Jan stared at me in heavy silence. I looked for any way to retract what I'd said, and finding none, I lay limp at her feet. Finally, she spoke in a quiet voice.

"I will not untie you, Raymond. I am going to beat you with my leather belt. You are going to know what it means to be whipped mercilessly. And, when I'm through and have taken your will from you completely, I will call Dom. Together, we will change your sexuality."

"No," I croaked. "You can't. It can't be done."

"Sure it can. But, first things first. You now have four minutes to work off."

"Oh, dear God. Jan, I beg you. Please! Not that! Not four minutes! I can't handle that much. Please? Safe word? Please? Please!"

As suddenly as sunbreaks appear after a tropical shower, she unlocked me from the bedpost. Then she led me to the bed, crawled next to me, and slid underneath.

"Fuck me right now, Raymond. Fuck me the way you used to."

My cock sprang to attention and found the moist entrance to Jan's vagina in a heartbeat. For the first time in ten years, I was inside her, sliding all the way in, thrusting deeply, all the way in, in and out, in and out. Our mouths met, and as our tongues danced together, I remembered her kiss but none of the reasons I had left her. From deep in my balls, a powerful urge grew, the next wave of cum boiling up within me, and before I could contain it, my wad shot into her. I stopped thrusting, holding myself deep inside of her, as deep as my erect cock could reach. Our bodies writhed and quivered together, and I remained inside as all of my cum drained into her. With my chest resting against her magnificent breasts, I kissed her tenderly, our eyes open. She liked kissing with our eyes open so there would be no mistaking she had been the woman I was fucking. Finally, she nudged at me to roll off, and I did, and in one fluid motion, she overturned me onto my back. Bringing her used muff down on my face with her weight to secure me, she ordered me to clean her out thoroughly with my tongue, which I did with great reluctance. Afterward, we sat together on the edge of the bed.

"So Raymond, how did it taste?"

"Your pussy?"

"Your cum."

"Oh. I don't know. I didn't really notice it, I guess."

"You've tasted cum before?"

"A woman's," I said.

"What about a man's cum?"

"Good God, no. My own, well, yeah."

She smiled. "Dominic will be joining us. You will get to compare yours with his."

"Jan, no! I said no! That's out of bounds!"

"Then you will be whipped for ten minutes."

"I still can't."

"Twenty."

"Nope."

"At some point, you will regard the pain of spanking to be far worse than whatever it is you fear. At that point, you will take his dick in your mouth, and you will swallow, and if you don't, he will cum again and again until you finally do."

"Jan, please don't make me do this. Please."

"It was that way for me, too. Women aren't born loving to swallow. You'll see. It can be fun."

"Fun?"

"Oh, yes. Quite enjoyable. Here, get on the floor. Now lie on your back." Standing over me, she put one toe in my mouth, her great toe, and began fucking my mouth with it. "Do you like this? You do, don't you?"

"Yes, but this is your anatomy, female anatomy, and I love it." She put her toe back in and I sucked it like candy while she kept up the fucking motion.

"When Dominic slides the head of his cock into your mouth, you'll close your eyes and pretend it's my toe." She was smiling, thrusting one toe, and then two, in and out of my mouth. "Now open real wide, hon. Good boy." She gently slid all five yummy painted toes into my mouth, pushing until the tips of her toes rested just short of where my gag reflex could begin. Opened to its limit, my jaw began to hurt and saliva oozed to my lips. Then she clicked pictures of her foot deep in my mouth and smiled.

"I love the sight of a man obediently servicing his woman this way." After a while, she changed feet and I serviced her other toes while she masturbated and brought herself to climax. I really did enjoy everything about her toes in my mouth. I just couldn't transfer that to any part of a male's body, least of all a dick.

After she was through, she removed her foot and ordered me to stand. As I did, I enjoyed the image of our nakedness as we stood in full view of each other.

"Jan?"

"Yes, my pet?"

"Um, you're on the pill, right?"

She smiled. "Nope. I planned this out long in advance."

"Planned what out?"

"Your seduction. Nope, no birth control at all."

"Shit! You do realize how fucking virile I am, don't you?"

"Yes!" she beamed. "It's lovely. I could use another tax exemption, child support, all that good stuff. So if I'm carrying your child..."

"Abort it!"

"Not a chance, Raymond! Never going to happen."

"You'll ruin me, ruin my marriage!"

"This choice was yours to make, hon. You could've backed out at any time. But it doesn't have to be bad. If I'm pregnant, just make timely payments to me, maybe an occasional return visit to this place, and no one ever has to know."

I sighed. I'd been beaten, figuratively, and for the next hour, she beat me with her strap and with her hairbrush. By the time Dominic got into bed with us, I was eager to do whatever else she wanted just to keep her from beating me. Dominic and I took turns fucking her, and at her skillful coaxing, I did finally take him into my mouth. Just as she had said, the first time was awkward and disgusting and I gagged. The second time, with the help of a few shots of whiskey, I let him hold the sides of my head and fuck my throat, and when he did cum, I was ready and swallowed it all.

But she wasn't right about changing my sexuality. What I did, I did out of duress. This was something she and Dominic would work to change in the future as we planned another threesome the following Tuesday, and the one after that. Sports night with the guys had come to mean something entirely different. Though I didn't regard myself as bi-sexual, I did begin to look forward to our romps in room 248.