My plan began at seven, staggering my visitors with enough time to spank, maybe have a quick drink, then be on their way as I readied myself for the next. If one failed to show I’d get a break, if two, even more. I didn’t really want any of them running into each other. Despite the fact that I was kneeling across the bottom of the single hotel bed at seven, naked except for a pair of two-inch heels, my ass cold and quivering in the direction of the door, I really did want this evening to be as private as possible for the great guys who agreed to join me.
What was I hoping for? Was this a last attempt at some sexual excitement Anthony didn’t show me? Would this night throw me back to the “good ol’ days” and cause me to break my engagement? Certainly not. I knew what this was all about. My husband-to-be treated me well, both in and out of bed, even spanking me often. I merely wanted to enjoy a last fleeting taste of many hands on my bottom, feel the wonderful nuances of different men, all in one night, all for one last time.
I sighed into the coarse bedspread as I looked up at the digital clock on the side table. The hour was upon me, and hopefully Gregory, the man I requested first, would show.
There was a knock. I said hello as calmly as I could, and the hotel door opened to admit my old lover. He had wide blue eyes and curly brown hair.
Gregory.
“What a nice sight,” he whispered and closed the door.
“Haven’t seen this in a long time, huh?” I asked, looking over my shoulder.
If I had needed to, I would have wiggled my hips, but I knew the way I was bent, I afforded my ex-lover of six years ago a good view of my meaty backside. Greg and I never had any problem getting hot for one another. He had loved my voluptuous body, as I had loved his rather thick frame and slightly larger-then-average cock. He had been a bright young man our sophomore year in college, and now he was a successful businessman, and he looked well kept in his khaki pants, brown loafers, and vanilla-colored button-down shirt. Always the picture of decorum, Greg exuded class and charm with his low-metered speech and slightly slanted eyes. I was as attracted to him then, bent over and naked, as I had ever been…and I could see by the smile on his clean-shaven face and the bulge in his pants that the feeling was reciprocated.
“I don’t think I ever really understood to what degree you liked to be spanked,” he began, coming to sit on the bed next to me.
As the mattress sagged slightly, I became even wetter. Greg was just sitting there having a nice little chat with me, while I was bent over bare-assed!
“Well, now you know,” I offered, looking up at him.
“If you don’t mind, I’d like to get you across my lap,” he said. “I mean, you lying there like that is great, but…”
“Anything you want,” I said and stood on my two-inch heels. Again another surge of wetness flooded my pussy as I faced my old lover, my trim brown “landing-strip” right in his face.
“I mean, I never gave it very much thought before,” he added, “when we used to do it. I just spanked you, however.”
“Yeah,” I sighed as a hundred memories of hot nights in Greg’s cramped apartment came rushing back to my mind.
“But when I received your letter…” He scooted forward and I bent across his strong, thin legs. “I began thinking about positions and…”
“Um,” I agreed, adjusting myself to feel his bulge against me, then…
SWAT!
Greg’s hand landed dead center on my cheeks so unexpectedly the breath shot out of me as I settled across him to ride the sting.
“I remember you liked it hard,” was his only comment as I squirmed and literally draped myself across the man.
I felt him raise his hand and—SWAT SWAT—I was smacked again.
This time he had landed a heavy blow to each cheek and I was aching between my legs as much as on my ass. I didn’t dare look over my shoulder at his expression. That would have been just too much for me at that moment.
SWAT. SWAT.
“You look as good as always,” he said as the heat seared across my buns.
SWAT. SWAT.
He hit me again, exactly like the last two.
“More then halfway,” he whispered, shifted, and then I felt Greg bend and actually kiss my ass.
“You don’t mind, do you?” he asked, sitting back up again.
“Um, na… no,” I sighed, squeezing my legs tight to relieve some of the building squishiness.
“I just wanted to taste that beautiful butt one last time.”
SWAT.
SWAT. SWAT.
Cheek to cheek, the hardest he had struck me yet. I held my breath, spread my thighs, my belly clenched.
“I’ve got to say, Jane,” Greg offered, shifting his weight to poke me in the side with his cock. “This was a very good idea.”
I’d say, I thought as I tried with all my might not to roll to the side into him. I felt an impending orgasm I feared I’d be too weak-willed to halt. I was getting so very close, so very quickly, to that point of no return where I would begin writhing and pressing myself into the man under me…no matter if Greg would want me to or not. I had suspected I would be turned on, especially in this oh-so-basic a position, but this quickly?
I felt Greg raise his hand again and reposition himself. Going rigid, I waited, pressing down, willing the orgasm to hold off at least for a few more seconds.
SMACK.
He hit me dead center, high, hard and even, and I jumped as Greg left his open palm on my ass and pressed down. Though I had an entire night ahead of me, I really couldn’t stop myself. It was a matter of having a quick release now, but maybe denying myself a real explosion later…? That was if there would be a later, since I had no real idea how many of my “invited” would show.
What to do?
My mind pulled one way and my pussy another. I was starting to circle my pelvis, grinding down, the heat really coming up through me now, Greg’s hand on my ass…
“Is that champagne for us?”
Fuck!
I wanted to scream. Greg leaned back, took his hand off my ass, indicating in no uncertain terms we were done.
I reluctantly rose off him, my knees shaking, my pussy hot, but my mind, at least for the moment, sliding down off that precipice of impending need. I stood to look down at his wide, thin-lipped smile. He was so goddamned matter-of-fact.
Fucker, I thought, and smiled at him
I managed to cross the carpet and poured two glasses of champagne. I had plenty of plastic ones on hand).
“Thanks,” was all I could manage as I passed him the drink. “Thanks for…coming.”
We both ignored the loaded meaning in that simple word. Greg knew how close I had been. And he knew that I knew he’d stopped short on purpose.
“I wouldn’t have missed it,” he said, raised his glass in salute and downed the sparkling liquid in one gulp.
I sipped mine. I had a long night ahead of me.
“I assume there are more guys scheduled,” he said and stood.
“I…” I demurely answered, looking up at him from under my curly bangs. I sat down, suddenly aware of how naked I was…not that I was about to get dressed, though.
“‘A last night’s indulgence,’” he quoted the invite. “I’m flattered to have been invited, since knowing you, there’s got to be a couple more coming.”
And just like that, Greg kissed my lips, stood back from me, smiled, handed me his glass and turned to leave.
“See ya at the church,” he said and then left the room. Yeah, Greg was one of the guys who had been invited to the ceremony.
He knew exactly what he was doing by leaving so quickly. He wanted to tease me as well as spank me.
I had thirty minutes to wait for my next…if he showed.
* * * *
Ronald never did make it, but I had promised myself no regrets or recriminations. I had heard my slightly chubby red-haired ex was involved with a woman quite a few years his senior and I assumed Ronny couldn’t reconci
le my request with his monogamy. He had always been a very honest guy with an acute cause-and-effect type of outlook. I missed him, to be sure, but held nothing but fondness in my heart for the guy.
I settled back to wait with two Everybody Loves Raymond reruns. When the time came for my third man, Gerald, I assumed my position again and there came a knock at my door not a mere minute past the hour.
The first thing I heard, even before Gerald’s heavy footfall, was the “swish” in the air behind me, followed by a tight, “Don’t turn around.I was hoping I’d find you like this when you said you’d ’be waiting,” he added.
Fear shot through me then, delicious, clutching fear as again I heard a short, quick flick in the still air of the room. God, what had he brought? Gerald always had a very good imagination, but I had not mentioned props or toys. I had had various implements used on me over the years – too few for my liking, actually – and I fetishized common items even at that late stage of my sexual awareness. (Tony’s mom had a wooden spoon in her kitchen that made my heart go into spasms if I looked at it too long.) But for Gerald to have brought something with him? Jesus Christ!
“Remember that time at George’s house, during the party?”
My mind quickly flittered back to a night some seven years before. Gerald and I had skirted off to a small bedroom at his friend’s house during a Super Bowl party and I was soundly spanked right on our host’s bed, my face inching into the coats of the other partiers. That was one of my most erotic memories, as well as one of the hardest spankings I ever endured, Gerald and I urged on by the chance of exposure.
“This is going to be ten times worse,” he added, and then I heard the cut in the air again.
This time the fucking thing landed!
It had to be a thin branch of some kind. It stung like all hell. But not only was I stinging, I was struck with a picture of Gerald, long and lanky in his usual black jeans and tight T-shirt, walking across the hotel lobby attempting to hide the long stick.
SZIP the thing said and I rolled to the bed to try and get away from the searing sensation.
Two more times the thing connected across my cheeks in the silence and I managed to look over my shoulder at the man with the steely blue eyes behind me.
“Hiya, doll,” he said and I watched as his hand rose and the wooden stick flicked through the hotel room air and bit me just below my ass, on the upper part of my thick thighs.
SZIP SZIP.
“Ah, Gerald, ah!” I screamed. Shit, we were getting loud. Would Bobbie be running down the hall any second from complaints to the hotel switchboard?
“You never said what I could hit you with,” he remarked and I just lay my face down into the cool bedspread, knowing he was reaching back again.
“Man, look at those little red marks,” he teased and again—SZIP SZIP SZIP—I was cut.
I started to cry as the heat rode up my flanks. God, could I take this? Did I want this? I lost count. Had that been eight or nine? How many more were coming?
“One last one,” Gerard said. “Let’s see if we can get you to stand.”
I did as he asked, looking at him fully then. He was regarding every inch of me from under his heavy lids, his cheeks aglow, his thin-lipped smile wide on his tight, dark face. Even then, as terrible as those searing cuts had been, I felt safe with Gerald. He wasn’t a big guy, to be sure, actually almost skinny in a way, but his confidence had always made me feel safe and warm when I was around him, safe like I felt right then. Although I knew the last slice would really hurt and although I feared feeling it, my fear was delightful since I trusted Gerald. I was so aroused in my blind safe terror—or because of it.
I put my hands to the edge of the bed and thrust my ass out.
“Last one is going to be bad,” he promised. “Worst yet. But when it’s over, it’s over.”
I braced myself and whimpered, tears rolling down my cheeks, legs shaking. God, was this wonderful, I thought as I heard the branch flick the air.
SZIP!
I fell to my knees. I was hurting to be sure, searing red pain, but the endorphins mixed with my clutching arousal and I came. Kneeling forward on my knees, feeling my hot ass for marks, a quick, gulping undulation gripped me as I crumbled there, gulping tears and coming.
“Wild,” Gerald announced, coming to my aid.
He knelt, I sat up best as I could, and he took me in his sinewy arms as we both rode out my sobs.
“That’s what you wanted,” Gerald reminded me, as I looked up at him a minute later.
Our lips met.
This was last thing I was expecting, but we kissed for a while, Gerald’s strong tongue finding an easy access through my thin lips, the pain on my ass numbing as I concentrated on rolling my tongue over his.
“Um,” I said when we finally broke apart. “Um, help me up.”
He helped me to stand, then walked me to the mirror that ran from one side of the bathroom sink to the bathtub.
“Feels a lot worse then it looks,” I said, looking over my shoulder to the sight of ten thin red lines on my tan cheeks.
I was red. I was stinging. But truth be told, my ass didn’t look bad at all. The sting of the cane, the slice it had made in the air before it connected, all this added to the idea of how lethal the thing was, but there really were no bruises on me. Crafty Gerald had hit me just enough to cause those quick searing jolts, but not enough to make a lasting impression any place else but my mind.
And even then I was thinking about the last two men I hoped would still visit me.
“Wild,” Gerald said again, kissed me on the shoulder, and walked from the bathroom.
“Really fucking wild,” he announced at the room’s door.
“Stay for a drink?” I asked.
“Honey, if I stay I’m going to want to do more then whip you,” he explained, tickling a lock of errant straight black bang from his high forehead. “That’s why I just came in and got right to it. I couldn’t give myself any extra seconds looking at your body and imagining what it would be like to be with you again.”
“I…” I tried, smiling.
“You are one hot lady, Janey,” he added. “Always were and always will be.”
Gerald smiled wide, then chuckled, took up his cane from the side of the bed, and left the room.
* * * *
For the next fifteen minutes, I vacillated between short quick sobs and laughter, all a delayed reaction to so hard a beating and the memories of Gerald, Greg, and even Ronald that flitted through my mind. This night was as much a rite of passage as anything else I knew. I was leaving one life, the single world I had so long ago physically left, and stepping into my life with my soon-to-be husband. For sure, I had been faithful during the two years I had been with Anthony and wouldn’t have wanted my life to have been any different, but with Gerald and Greg I began to remember that a great part of me was being a sexually submissive woman. It was good I was hurting, that my ass was stinging; like everyone, I needed to be reminded from time to time of my real feelings.
There was no way I’d be going into my marriage without asserting my non-assertiveness.
I was sitting on the bed when the door slowly slid open.
Carl was undoubtedly one of the best-looking men I had ever dated, and also one of the gentlest. He spoke barely above a whisper, smiled easily, and was by far one of the kindest guys I had ever known. He had also been meticulously sexual, taking time, setting candles, pouring wine, drawing scented baths, easing me to heights of such abandon that at one time, I could imagine no other lover. But as things go in life, we broke up. Carl was ten years my senior and building businesses all over the country, and I wasn’t leaving town. But I never forgot him and had managed to discover his address through a friend of a friend. He was the one man I had thought wouldn’t show given the three hundred miles that separated us, but I was tickled to no end that he had. I rushed over to the door, as if I was clothed and we were just meeting for a normal Saturday night da
te.
“Ah,” he said, breaking from my quick embrace. “Now, now. Let’s have a look at you.”
I turned completely around like I always had when Carl inspected me. He liked to have me model outfits he bought for me, which I always readily did.
“I guess you weren’t joking, huh?”
“No,” I admitted, slithering against him again.
I guess Gerald’s whipping had gotten the better of me. The delightful smirk on Carl’s face, his cool blue eyes, and fine-cut jaw were so enticing I ached to jump him then and there.
“You know…” he began, sitting on the bed as I followed. “I don’t remember spanking you all that much.”
This was true. Although he had swatted me a few times, soft over-the-knee spankings, and he knew well how I loved them, Carl had other ways of making me submit. Those modeling sessions I mentioned often led to us going to dinner with me wearing the skimpy outfit in public, sans underwear or bra.
“But when in Rome…” he quipped and pulled me up and over his lap. “Ten, right?” As I lay there I felt his fingers snake in between my thighs. I opened and ached as he tickled my tight wet lips.
“As wet as always,” he whispered, exploring my suffering sex. This was the first time all night I had been touched and I was aching for it.
But then I was hit.
My ass was alive, even more so after Gerald’s numbing caning. I bucked as Carl began to swat evenly and soft. He had a way of pushing down on me after every swat, as if willing me to grind against him even harder then I already was.
On his fifth swat I began to moan aloud and really grind.
“Going to come?” Carl asked and—SWAT SWAT—I was hit cheek to cheek.
“Go ahead, go ahead,” he coaxed as he hit me two more times.
I clenched down with all my might, rubbed my pubis against his strong legs, and grabbed the bedspread in my fists.
Wicked Pleasures: Stories of Kinky Love Page 12