I drove to my appointment with a mixture of nerves and anticipation. I expected the nerves I’d felt before my previous attempts to sate this desire I’d lived with for so long, but there was another element to them this time. What if I didn’t like it? What if I was again disappointed that it didn’t measure up to my lifelong fantasy? Would it then never happen?

The anticipation felt different than before. Yes, I was excited as Nicole seemed very different from the others. I’d discovered her internet listing in what seemed a more reputable site where several similar listings didn’t include those I’d previously tried. She responded quickly and had me call to be sure she understood my needs and that I understood what she was about. I would get all I asked for and more. In other words, I wouldn’t just walk in, take my pants down, and get my spanking over her knee.

This would be my fifth attempt. The first time was purely accidental as my curiosity got the better of me, and I went into one of those short-lived "lingerie modeling" storefronts. One assumed that you’d get a private modeling session with some girl showing off her body in enticing underwear, and that’s what you got, sort of.

Pamela was attractive in a sultry way with a thin body, store-bought tits, and a tiny ass, but her face could be pretty given a chance. I paid the fee and was shown to another small room where I sat, and she removed her robe, modeling her black bra and panties. It wasn’t all that different from a stripper bar apart from the close proximity and one-on-one service.

I wondered if there was anything more to it, and I didn’t have long to contemplate when she asked me what else I would like. Having left the door wide open, I figured, "What the hell?" I’d almost certainly never see her again, nor would we know any of the same people. I told her I’d like to get spanked. She smiled and told me to stand up. Taking my place in the chair, she took me over her knee and spanked me a half dozen times. When I asked what it would take to make it a real spanking, she wrote a price on the back of a business card and said I should call her. So, I did.

I had similar, though more extreme, bouts of nerves and anticipation that first time, and I wish I could report that it was all I was hoping for. It was a different location, a mild dungeon of sorts, and I got my first ever bare-bottom spanking across her knee, but it wasn’t what I was expecting. Disjointed and uneven in its delivery, it wasn’t what I wanted. In addition to being high on something, she was frequently pulled away to answer a ringing phone. Better than nothing? Just barely. I gave her a second chance, but it was no different.

I met Seanna by returning to the same location I’d been with Pamela. Very young, not even twenty if I had to guess, she had a youthful body with tiny tits but a full round bottom. I got a dozen spanks over my Dockers from her, and I could take it further right then and there, but the price was astronomical. Not surprised at my stunned reaction, she also handed me a card and whispered she would do it somewhere else for less than half that price. She had me hooked when she said she liked to get spanked as well.

To make a long story short, she didn’t meet my expectations either, as she was very inexperienced and needed constant direction to get even close to what I wanted. I gave her a second and even a third chance, but nothing changed. I did give my first spanking ever, but after less than ten swats, she was crying and rubbing her bottom as though in extreme pain. Maybe I started too hard, but ten?

I gave up at that point, and it was years before I decided to try again, this time using the internet. Finding someone whose description seemed a good fit, I called and spoke to Breanne for at least ten minutes. I made sure she understood that while I might like some of the other services she offered if I spent ninety percent of the time across her knee getting spanked, I’d be very happy. And if I were happy, I’d be a repeat customer.

She said she understood. I’m not sure why because clearly, she didn’t. We spent the entire hour in what I later learned was called a "tease and denial" session, where I kissed and rubbed her feet while she teased me, repeatedly asking if I wanted to get spanked. Of course, my answer was yes, but I got no more than six or seven spanks the entire time and not even all at once. I would have refused to pay if I hadn’t already given her my money.

Again, I gave up for a while, but any spanko knows those unrealized desires don’t just go away. Another internet find went the opposite way, where I was literally beaten from the outset with all manner of implements: paddles, straps, floggers, almost none by hand, and no OTK. It’s in my makeup to just take it, but I was in more pain than I imagined twenty minutes in.

It was certainly better than previous attempts, and I made another appointment, hoping to explain better what I was looking for. I called an hour or so before to confirm the appointment, but she told me I had the wrong time and she couldn’t do it now. I told her I’d come whenever she wanted, but she hung up on me and didn’t answer any future calls. I had no idea what I’d done wrong, and another path to my fantasy had become a dead end.

I’m not a quitter, and after the one overly severe session, I was hopeful that, in time, I could find someone who would bridge the gap between the two extremes I’d experienced.

Her name was Nicole, and she was gorgeous. Her pictures on the site didn’t do her justice, but they were still exciting. Tall with long, blonde wavy hair, she had a shapely body with a cute little butt, perfectly sized firm tits, and long well-toned legs made longer atop four-inch heels. Costumes ranging from motherly or school marm to full-on dominatrix increased her allure. The photos of her in full swing, with paddle or strap in hand, about to strike an already red bare ass, convinced me, and I fired off an email.

Dear Nicole,

I got your contact information from the Eros website. I would very much like to schedule a session with you, but I want to make it clear that my primary interest is in spanking. I prefer to be taken over your knee for a long, hard, hand spanking, but other positions and paddles are interesting to me as well. I’m NOT into domination, like being tied up, gagged, or tortured, but I do want you to decide how I should be punished. I look forward to your reply.

I was encouraged by a quick response that same evening.

I can do that for you. Call me tomorrow at noon.

So I called and was pleased from the outset at her friendly but confident tone. When she asked, I gave her the highlights of my previous unsatisfying experiences, and she assured me an hour with her would be nothing like those.

“So, are you up for a little role-playing?” she asked.

“I’ve never done it, but I’ll give it a try,” I answered, trying to be open-minded.

“Good. I have several rental properties, and as my manager, you will collect the rent from the tenants. One has been delinquent for more than a month, and they will be your priority. Get the rent from them or else. I think you know what will happen if you fail.”

“I’ll get punished?”

“You’ll get spanked!” she replied with heavy emphasis on the last word. “A long and hard spanking on your bare ass! Do you understand?” she added authoritatively.

“Yes, Miss!” I replied, my dick already reacting to the threat.

“Call me Goddess when you address me!”

“Yes, Goddess!”

“Good. I’ll see you the day after tomorrow!”

I got off the phone more excited than ever. I went to the bathroom to take care of my raging erection, picturing myself lying across her bare thighs, finally getting the spanking I’d imagined all these years.

I drove past her house to be sure I knew where it was and continued to the other end of the street to park in a convenience store parking lot while I waited.

‘In the neighborhood,’ I texted as instructed.

‘Good boy. I’ll bring you in when I’m ready,’ she replied.

Not wanting to be late, I’d arrived early, and those fifteen minutes seemed like forever until finally, ‘Come to me.’

I slammed the car in gear, and with screeching tires, I left the convenience store on my way to my dream.

I pulled up to the nondescript small house in a very ordinary neighborhood and parked in the street, the driveway taken by a Chevy Nova in muscle car garb. I went to the trunk to retrieve the gift I’d brought her and walked to the door, my insides quivering.

Rather than using the doorbell, I knocked as instructed, and the door opened seemingly on its own. I stepped inside, the door closed, and there stood my Goddess.

“Hello,” she said to my stunned face and smiled at my reaction. A silky robe was about all I could see except for a hint of cleavage in a red bra and towering red spike heels, which made her a bit taller than my five-eleven height. Her long blonde hair, in twisted curls, flowed over her shoulders and framed a face that could be both strikingly beautiful and steely stern.

“Oh. Um. Hello, Nic … um, Goddess!” I stammered.

“You like?” she asked, standing close enough to feel her warmth and smell her intoxicating scent.

“Oh yes!” I said, smiling meekly. With one hand on my cheek, she kissed the other.

“Is that for me?” she asked, indicating the gift bag I was holding.

“Yes. Yes, I made this. I hope you like it,” I replied, handing her the bag.

Pushing the tissue aside, she pulled out the paddle I’d made. Fashioned after the large round paddles used on the beach, it was made with thicker, heavier wood and coated in many layers of polyurethane, making the surface smooth and glassy.

“Ooo, I love it!” she replied genuinely, with a smile that ensured she’d use it on my bottom before long.

“The bathroom’s to the right if you need it. Come across the hall when you’re ready to begin,” she said with a sly smile and turned to leave.

I went to the bathroom, not because I needed to use it, but to prepare my mind for what would come. I was so excited; I just knew this would be different. I had no idea how much.

I walked into the room with nerves raging, which was appropriate for my situation and role.

“There’s my trusty manager! Have you got good news for me?”

“Um, yes, I do! I’ve collected all the rents you asked me to …”

“Good!” she interrupted. “And those deadbeats on Floral Avenue?”

“Well. Um. No. I …”

“What do you mean, ‘no’?” she asked angrily.

“I tried! Really, I did. They weren’t home the first two times I went there, and the next two times, they said they didn’t have the money!” I replied, offering my well-rehearsed excuse.

“And then?”

“And then I … I left. What do you want me to do? Demand the money at gunpoint?”

“No, I expected you to be threatening enough that they’d want to pay to get you off their back. But you couldn’t do that, could you!? You remember what I said would happen if you failed, don’t you?”

“You said I would be … punished.”

“No, I said you would be spanked! On your bare ass!”

“I didn’t think you really …” I started.

“You didn’t think I meant it? Well, I did and it’s going to be one helluva spanking after those lame excuses! Take your pants off!” she finished, but I was distracted by her opening her robe and letting it fall to the floor.

The lace-trimmed panties that were barely more than a G-string demanded my attention as I imagined a smoothly shaved pussy under that tiny triangle of red satin. Bending over to arrange something on the futon bed behind her, she thrust her cute, round cheeks out, undoubtedly for my benefit.

She turned around to see me just standing there staring.

“I guess you didn’t hear me!” she said haughtily and stepped up to face me. “I said to take … your … pants … off!” she said, punctuating each word with a smack on my ass.

“Yes, Goddess!” I said as I opened my pants and pulled them down with my underwear to my ankles.

“I didn’t say to pull your underwear down!” she said, smacking my now bare bottom again. “No, don’t bother pulling them up now!” she added. “You may as well have this off, too,” she said, pulling my polo shirt up and off, leaving me completely naked.

“Does this excite you?” she challenged, taking hold of my erect cock and pulling me to her side on the futon. “We’ll see how long he lasts while you’re getting your ass spanked. Now get over my knee!”

I tumbled across her lap, my cock falling between her spread thighs that closed around me once in position. She’d barely started, and I already knew this would be better; the first OTK spank on my bottom was proof of my conclusion.

She spanked firmly but not hard at first, gauging my reaction to determine how quickly to escalate. It felt so good I was lifting my hips, inviting more, harder, faster, and she delivered. She scolded her ineffective rental manager as she punished me.

“Are you going to get my money from those deadbeats?”

“I’ll try, Goddess!” I replied, feeling real pain now.

“NO TRY! YOU … WILL … GET … MY … MONEY!” she said, emphasizing each word with both hands spanking at the same time.

“Yes! YES! I will!” I responded, and she stopped for the first rest in several minutes.

“Good boy!” she cooed as she raked her long fingernails over the very tops of my cheeks.

“Oh! Oh! Oh, fuck!” I gasped as her sharp nails stimulated the sensitized top of my cheeks, causing my back to arch and my body to writhe in her lap. She repeated it on each cheek, spanking hard and fast, then quickly the fingernails, and each time, my body convulsed in reaction. It was an extraordinary feeling, like being tickled without the laughter.

The spanking resumed with random patterns, force, targets, and even hands as she peppered my stinging bottom, finally getting the gasps and grunts she wanted from me.

“I thought you said you’d never had a proper spanking?” she asked during another rest, her hand just caressing and squeezing my burning bottom.

“I haven’t Goddess. Not like this!” I replied, hoping she’d take it as a compliment.

“Then why did it take this long to get a reaction out of you?” I didn’t answer partly due to her exploring fingers running down my crack, tapping and gently pushing on my anus, but mostly because I was embarrassed. “Tell me!” she demanded, spanking harder than ever and still getting no answer, added, “How!”

“Ow! OW! I … I spank myself!” I admitted finally.

“Really!?” she responded with interest as her fingers tested my backdoor again. “Show me!” she demanded.

“What!?”

“Show me! Come on, get up!”

She made me stand up and reach back to spank myself with my hand. Harder and harder until I could see she was satisfied with the result.

“Well done!” she complimented, “Most people don’t do it hard enough, subconsciously holding back. How long do you do it?”

“Hundreds of spanks usually. Often over a thousand!” I said with some pride mixed with my embarrassment. “The paddle is more effective,” I added, indicating my gift lying next to her.

She handed me the paddle with the instruction to give myself twenty swats and jumped at the first report, liking the loud pop this paddle made with each impact covering both cheeks. I started with moderate force but had built to painful swats before I finished.

“Impressive!” she said as she stood with her hand out. “Give me the paddle!”

She bent me over, my side pinned against her hip, and wrapped her arm around my waist before giving me a few playful swats to get the feel of the paddle’s size and weight. The first pop was as loud as those I’d created.

“Ooo, I like this!” she enthused as she swatted relentlessly. “I love that sound!” she said, repeatedly giving me three or four swats in rapid succession.

Crying out repeatedly and gasping for breath, I took my punishment, the pleasure diminishing as the pain increased. I was nearing my limit when she stopped again.

Fishing around a nearby shelf, she was looking for something, and having found it, she dropped it on a large padded bench at waist height. She pulled the bench away from the wall, giving me a closer look at her find. It was a black glove made of soft, supple leather, and I assumed it was a spanking glove. Motioning me to the bench, she had me bend over it and put my hands on a rail on the far side. I was surprised when the spanking didn’t resume, wondering whether the glove would provide a new sensation.

“I think you’ll like this,” she said, showing me her gloved left hand. The back of the glove had been unremarkable, but I breathed in sharply when I saw the palm. Covering the entire palm and fingers were sharp, metal points, a couple of hundred of them. I looked back at her in fear but jerked forward with the first hard spanks. Mixed with the renewed pleasant pain was relief that it wasn’t with the spiky glove. Spanking one cheek at a time, the tempo and intensity built quickly to the hardest today.

“Oh, my God!” I screamed as the spikes in her glove covered my bottom with that amazing hyperstimulation all over my cheek that her fingernails only hinted at. My back arched, and I gasped, writhed, and squirmed at the sensory overload all those tiny sharp points created. Even more than before, I wanted more at the same time that I wanted it to stop. Each cheek given this treatment twice, with longer, harder spanks and swats of the paddle between, left me a twitching, heaving mess draped over her bench like an electrified corpse.

“I told you you’d like it!” she said when I was allowed to stand. “I think you’ve earned a little reward,” she added with a cute, disarming smile. “Put your arms behind you.”

No more than a foot away, I watched as she reached back to unclasp her bra. Cupping her hands around her firm tits, she held the bra in place while she played with her ‘girls’ before dropping the bra and thrusting them toward me.

“Lick them!” she ordered, stepping forward, and I quickly brought my tongue’s tip to her erect nipples. Told to suck, I did so greedily, my lips covering her perfectly shaped areola. Grasping each tit from below, she mashed them into my face before gripping my face between them, her soft flesh caressing my cheeks and prompting a brief thought that this was every bit as good as I was anticipating and much more.

“Kneel!” she commanded, interrupting that chain of thought.

Sitting back on my heels, I looked up at her statuesque body, the tits so recently in my mouth, fondled by their owner again. Taking a step back, her hands glided down her tummy to that tiny triangle of satin concealing her pussy. My erection, which had softened under the punishing barrage of her hands, grew again as she pulled it down far enough to see she was shaved smooth.

Like a stripper teasing her captive audience of one, she pulled the strings this way and that, giving me glimpses of one swollen lip at a time but never the full view. Turning around, she pulled the elastic strings down over her hips, but before letting them go, she bent to push her cute, round ass in my face. With one hand on her thigh, the other reached back and pulled my face into her crack, ordering me to kiss and lick whatever she stuck in my face, including her winking rosebud.

Standing but bent slightly, her hands pulled the elastic free of her hips and let the panties fall around her feet, still teetering on those impossibly high heels. She giggled as I groaned, an audible plea to turn around and let me see. She kicked the discarded garment away and slowly turned around.

“Oh, Goddess!” I moaned as her perfectly smooth, perfectly shaped pussy came into view. Two meaty lips, defined by a tight slit with a glistening line between revealing her arousal, disappeared between her legs.

“You like?” she asked as if my moaning wasn’t an answer. “Kiss her!”

Leaning forward, I placed my lips on the tiny tongue of her inner lips protruding from her slit and kissed lightly. When my tongue tried to get a taste, she pulled back.

“Not yet,” she said softly. “Try again,” she said, and I obliged. My lips kissed up and down her slippery slit, and she pushed it into my face when I insinuated my mouth into the folds, then grabbed my hair and pulled me away.

She stepped back again, this time to the futon, and sat down, her closed legs hiding my prize.

“Do you want her? Hm? My hot, wet pussy?” she teased as she spread her legs and let her fingers torture me while they parted the magnificent petals of her sweetly fragrant flower. “Do you want to lick my pretty, little pussy?” she asked as she saw the pained look on my face.

“Goddess! Please?” I begged, and she motioned me forward.

On my knees, my hands came away from my back to balance my awkward walk to her, but she quickly cautioned that, again, no hands were allowed. Kneeling between her feet, I bent forward, looking at her face for approval, and getting it, my tongue slithered into her waiting slit.

As much as she knew about my prior spanking experience, she didn’t realize that this was a first for me. Sure, I’d licked pussy before, but this was the first that was shaved, freshly shaved by the feel of her silky smoothness, and I was instantly spoiled. Even one with only a sparse tuft of hair on the mons couldn’t compare to the smooth curves and precious, pink folds of flesh I tasted.

Humming and groaning in delight at my fanciful feast, I licked and probed as my face buried itself in her wetness. Impatient with my progress, she grabbed a shock of my hair again and pulled me into her gyrating hips. Holding my face in her hands, she moved it in time to her rhythm, grinding against my mouth and nose, my face a scratching post for her playful kitten.

With nowhere near enough time in this heavenly place, she pushed me away and closed her legs.

“Not good enough! Get over my knee!”

Again, in total disbelief, I lifted my hips, offering my bottom for more of this exquisite torture. The sensual interlude with her ass and pussy had provided enough of a respite to appreciate another good spanking. And it was good, the almost-too-much pain returning after minutes of continuous, quick-tempo spanks covering my flaming red ass.

“Get up and bend over the bench like before!” she ordered. I got up, feeling the stinging pain as I stood and hobbled over to the bench, welcoming its strong support of my weakened body.

“No peeking!” she said when I turned to look at her. I heard some rustling mixed with a jingling metallic sound that left me wondering what she had planned next, but I kept my eyes averted as instructed. My first clue to what was next came when the paddle that had been lying on the bench next to me disappeared, to be followed quickly by the first swat of what would be the finale of the best spanking ever. At a steady pace, the sound of the paddle was as impactful as the pain it produced.

“Ah-ah!” she cautioned again when I tried to look, catching only a brief glimpse of her arm swinging the paddle to impact my blazing, hot ass. Unable to avoid the paddle, I was getting to the point of wishing I had a safeword when she finally stopped.

My bottom was on fire, so the feeling of a cool liquid dripping between my cheeks was a welcome contrast. It ran down my cleft and was caught by her finger, smearing the slippery fluid all over my tight anus, clenching even tighter when her fingertip pushed inside with the aid of the lube.

“Maybe next time you’ll do a better job eating my pussy!” she said, moving close to me and stroking with her other hand what she hadn’t wanted me to see before now.

I wanted to object when I saw the long, black cock strapped to her hips, but I couldn’t. I didn’t want to get fucked in my ass, but I also wanted to do whatever she told me to, and my submissive side won out.

She stepped back, and with one hand on my hip, she guided the tip of the fake phallus to my tight hole. Pushing gently, she told me to relax, a suggestion that sounded utterly ridiculous when someone was trying to shove a six-inch pole up your ass. Nevertheless, I tried, and when the tip was finally in, she pushed a little further, two steps in, one step out.

Gasping and grunting at the intrusion, I finally relaxed a bit and found the feeling not unpleasant. I pushed back a bit, wanting more, when she told me to ‘Take it easy.’ Another pullback, and I felt I was ready for it all, having no idea how much more there was.

“Oh, my God!” I cried as it went all the way in. She kept her hips pressed against my hot ass, moving ever so slightly in and out to let me get used to the fullness.

“Good boy!” she whispered in my ear, bent over me and jerking the cock forward.

Pulling out just an inch or two felt like a full retreat, and plunging back in, a full insertion. A little further each time, and before long, the hard shaft was gliding smoothly in and out, my hips moving in rhythm with hers. The feeling was incredible, and even now, I’m at a loss to find words to describe it.

“Oh, good boy!” she repeated, liking the active role I was taking in having my ass fucked. “You like having my cock in your ass?”

“Yes! Yes, Goddess!”

Just when I thought it couldn’t get any better, I felt her hand on my cock. The remaining lube in her palm provided a smooth, gliding stroke as she jerked me off. I held my breath as my body stiffened and muscles tightened, wanting to hold back the coming explosion as long as possible. The combination of the cock in back, fucking my ass, and the cock in front fucking her hand created the most incredible ascension to a climax I’d ever felt. When I couldn’t hold it any longer, it shot out of me like a flame thrower, splatting on the wall just inches from my face.

“Oh, fuck!” I panted as my body, lying limp across the bench, quivered inside when she pulled the intruder out of my ass. The emptiness was replaced by the reminder of the stinging pain I felt despite her soothing, caressing hands.

Remembering how I felt when I first arrived, a bit of fear and a ton of anticipation, I concluded that I’d been right in expecting this time to be different from all the rest, though admitting to myself that I’d had no idea how much. I had wanted only the kind of spanking I’d fantasized about for so long, but she had given me so much more.

She took me in her arms when I could finally stand and held me against the body she’d shared with me unexpectedly.

“When would you like to come back?” she asked, knowing I would return for more of the same and more.

“Tomorrow?” I said jokingly to our combined laughter.

~~~~^~~~~

He finally got what he was looking for, even if he did have to pay for it. I hope you liked my story. Please remember to 'Like' and/or 'Favorite' it if you did. Thank you for reading!!