1 - A Surprise From My Past

When the caller ID came up, ‘Taylor,’ I answered the call carefully. She’d been someone I’d had sort of a relationship with a year or two ago, but she’d seemingly disappeared. When I’d try to call her, I’d get voicemail with a system greeting. I’d leave cryptic messages that only she’d understand, but I never got a reply. I got no response to texts either, so eventually, I gave up trying to reach her but kept her number, just in case, which, at the moment, I’m thinking may have been a good idea.

I answered with a tentative ‘Hello’ to let her identify herself first in case it was someone else.

“Hi, this is Taylor. Is that you, Mark?”

“Taylor! I haven’t heard from you in ages! Where have you been?”

“That’s a long story for another time. How are you?”

“I’ve been good. I tried to reach you a bunch of times but never heard back. Are you okay?”

“Yeah, I’m fine; in fact, I’m doing really good now. I’ve gotten my life together, so I thought I’d give you a call. I finally got a good job that I’m doing great at. My son is doing much better in school, and everything is settled down; no more just barely getting by. So, the other day, I thought of you and decided to give you a call. See if maybe we could get together again?”

“Um, yeah, we could do that,” I replied, confusion evident in my voice. “Taylor, if you’ve gotten everything together so well, why would you want to return to …”

“No, not like before,” she interrupted, “This would be different!”

It had been a long time since I’d had a girlfriend who shared my interest in spanking when I first met Taylor. She worked at a short-lived establishment that offered ‘Lingerie Modeling.’ Presumably, you’d pay to watch attractive girls modeling sexy lingerie for you. It sounded more legit than a stripper bar, but in reality, they were eventually identified as fronts for various forms of prostitution and closed down almost as quickly as they’d opened.

One night, my curiosity got the better of me, and I picked one I drove by often, went in, and Taylor was the model on duty at the time. She was young and cute and a little flirty. At one point, I suggested that she was being rather naughty when she replied with something like, ‘Ooh, are you gonna spank me?’ My antennae went up, and the flirting continued along that line.

“What’s your name, naughty girl?” I asked.

“Taylor.”

“Do you get spanked when you’re naughty, Taylor?”

“Sometimes. I like a little spanking. Would you like to spank me?” I suspected that would come at an added cost, so I was reluctant to accept her offer. She placed herself over my knee and let me give her a dozen mild spanks over her panties. “I’m sorry. I won’t be naughty anymore,” she said as she got off my lap, smiling.

“So, is that the kind of spanking you like?” I asked to see if she was really into spanking or just a few well-timed swats on her bottom during sex. The sexy swats being her idea of spanking was of little interest to me, but I had to take the conversation further.

“Have you ever given someone a spanking?”

“Yeah, I know a guy who likes getting spanked, but he wants a real spanking. I pull his pants down, put him across my knee, and spank his bare bottom really hard for a long time! His cheeks are deep red and usually bruised by the time he’s had enough.” She could probably see the renewed interest on my face and asked, “Do you like getting spanked like that?” I just nodded in reply.

She motioned me to get off the chair, sat down, and patted her thigh. “Come here. I’ll give you a spanking,” she offered, and not needing to be asked twice, I eagerly lay across her lap. She smacked my fully clothed bottom maybe ten times and told me how much it would cost if I wanted it to continue. The cost was exorbitant because they charged for the ‘room,’ the establishment, and the ‘model.’ She could see the price had turned me off, so she leaned over and whispered, “I’ll do it for a lot less.”

2 - Paying For a Spanking

I’d never paid for any kind of sex before, but between the fact that it had been a long time since my last spanking and her tight, little body being very appealing, I decided to go for it. I’d gotten the impression that these sessions were either watched or recorded since she’d been so careful about what she said aloud, so I gave a slight nod of agreement.

She went to a table and picked up a business card from a plastic cardholder. “I hope you come again,” she said as she shook my hand and gave me the card. I left slightly confused, but that ended when I got outside and looked at the back of the card where it said, ‘Taylor. Call me,’ with a phone number.

I waited till the following afternoon before calling the number because, being the skeptic I am, I was at least a little suspicious. I said a quick ‘hello’ before identifying myself as the guy from last night. It had been a slow night, with only two customers, so she remembered me quickly.

“I’m sorry about last night,” she said apologetically, “but we have to sell the club’s services, and they’re always watching for someone trying to set something up outside.”

“I understand,” I said, leaving the talking to her while I assessed the situation to ensure I wouldn’t just be ripped off.

“So, you’re into spanking,” she said more as a statement than a question, “I told you about the guy who wants what he calls a ‘real’ spanking. We do it a few different ways, but mostly, he wants to be across my knee like a ‘naughty boy’ while I spank him with my hand. 

“We start with his pants on, but he gets most of it on his bare bottom. He likes me to call it his ‘bottom.’ Once he’s over my knee, he gets spanked for most of the hour! I must give him many hundreds of spanks on his bare bottom before he’s been ‘properly punished,’ as he calls it. He really gets off on it! So, tell me what you like!”

“Yeah, that’s pretty close. I like paddles or a hairbrush as well.”

“I don’t have any …”

“I’ll bring them,” I interrupted.

“Oh, good! So … “. She discussed logistics and price, and we agreed on a date and time a couple of days away. She said she’d arrange a meeting place and call me with the address.

After the call, my initial reaction was, ‘What have I got myself into?’ but I chalked it up to the normal jitters of getting together with a new spanking partner. There’s always a bit of apprehension when you don’t know the other person well. The biggest problem with first spankings is either getting spanked too hard or not hard enough, and it might take several times before your partner learns how you like it. 

Having never ‘hired’ a person for something like this, I still worried whether it might be a setup, but I allayed my fears with the argument that she couldn’t conduct much of a ‘business’ if she ripped off every first-time client. At least if I didn’t like the outcome, I didn’t have someone expecting me to call back, and I could easily walk away.

She called the following day to give me the address where we’d meet. Though I didn’t know it till I arrived, it was her friend’s apartment who allowed her to use it for an hour. I wondered whether the friend knew what she was going to do there.

I made sure I knew exactly where it was as it was more than twenty miles from my home in an unfamiliar area, hoping it would be a reasonably good neighborhood. I would text her when I’d arrived, and she’d text back when she was ready.

The time came, and I drove to the location more nervous than I would be on a first date for all the reasons I’ve already mentioned, plus a few more. I arrived early to scope out the location to give me a little more comfort. About ten minutes before our agreed time, I texted that I was in the parking lot. Her return message said she would text me when she was ready.

I watched the entrance, hoping to see her as she entered. The truth is, I didn’t remember her face as well as I thought I would, but I did remember her tight body and small but enticing tits. I had no intention of doing anything beyond the spanking, but I had no idea what she was expecting. I never saw anyone go in, but I got the text a few minutes after the agreed time that she was ready. Having not seen her arrive, she must have already been there when I’d messaged.

I went to the door and knocked with a raging case of butterflies. She answered quickly and invited me in. I wouldn’t expect her to be as enticing in regular street clothes as in the lingerie I’d met her in, but she looked kind of cute and sexy, not quite girl-next-door, but close.

She was shorter, not wearing the heels she’d had on, but her tight jeans accentuated her legs and waist and everything in between very nicely. A striped sweater and bare feet completed her clothed image. 

Though somewhat plain, her face was cuter somehow in a normal setting, perhaps shedding the image of a sexy model. She had a nice smile framed by long brown hair that hung straight over her shoulders and perky small breasts. The overall appearance of someone you knew well who hadn’t dressed or cleaned up to impress you.

“Hi, Taylor,” I said, smiling but still nervous, “You look nice in street clothes.”

“Thank you! Come in!” she said as she turned to lead the way. “There are no good chairs for me to put you over my knee,” she said, jumping right into the subject at hand, “but we can use the sofa. Is that okay?”

“Sure, that’s fine.”

“So, what have you done to deserve a spanking?” she asked as she stripped off her top to reveal a plain, half-cup bra. “Hmm? Have you been a naughty boy?” she continued unbuttoning her tight jeans and shimmying her way out of them as well. Her tiny panties barely covered her in front, and when she turned, the thong allowed a clear view of her plump cheeks. I suddenly wanted to spank her again.

“I’ve been thinking about your tight, little body and what I’d like to do with it!” I lied, inspired by her near-nakedness.

“Oh? Now, is that nice? No, it’s very naughty, and I think you need a good spanking!” she said as she reached for the buttons of my shirt and quickly had me bare-chested. “Should you be thinking about my body like that?”

“No, ma’am.”

“No, you shouldn’t! So, you’re gonna get spanked!” And with that, she turned me sideways and started spanking me over my pants. They were mild spanks, but I doubt I would have felt much through my pants, regardless. “Come over here!” she commanded, leading me to the sofa and sitting down.

“You won’t feel a thing with these pants on, and spankings are supposed to hurt, so pull your pants down!” I’d barely got the belt open when she took over and took them down herself. Leaving them bunched at my ankles, she pulled me down across her knee. “You’ve been very naughty! What should I do with you?”

“You’re gonna spank me, aren’t you?” I replied, getting into the spirit of it and positioning myself on her lap.

“That’s right! You need a good, hard spanking! And on your bare bottom before we’re through!” The spanks that followed were felt more because they fell on my tight briefs. She knew what she was doing, and I raised my hips to meet her spanking hand. Perhaps a hundred or so spanks later, she declared that my underwear needed to come down so she could ‘spank my bare bottom till it’s nice and red.’

She pulled them down to the top of my thighs and wasted no time resuming my ‘punishment’ on my bare butt. She spanked the fleshy tops of my cheeks, alternating sides for twenty or thirty at a time, with minimal chatter about my misbehavior. Gradually, she spanked harder, but not too many at a time, as I imagined she might not have the strength to keep it up for very long. It felt really good to be finally getting spanked again. It had been too long.

“Did you bring me something to spank your bottom with?” she asked as she ran her fingers over my sensitive cheeks.

“Yes, ma’am. Shall I get them?” she lowered her hands to her sides, and I got up with my underwear still pulled down in the back. Opening the shopping bag I brought, I took out a large round paddle I’d made fashioned after a beach Smash ball paddle, but much thicker and heavier, and a wooden hairbrush.

“Ooo, I like the look of that!” she said, getting up and taking the paddle from me. “Bend over!” I bent where I stood and felt a tentative swat and a loud report. Again, she managed a pretty hard smack, followed by several more. “I like the sound of this! How does it feel on your red bottom?”

“It stings a lot, Taylor. Maybe I should bend over the end of the sofa?” I suggested.

Without waiting for an answer, I moved to the end of the sofa and laid over a high, barely cushioned arm, giving Taylor a prone target she could swing down at. Initially standing at my side but then moving behind me, she laid down at least ten good swats that covered both cheeks well. ‘Now, we’re getting somewhere,’ I thought with a painful sting in my cheeks. Even so, I lifted my bottom to meet each stinging swat.

“Tell me what you were thinking about my body! What was your dirty mind imagining you’d be doing to me? Hmm? Tell me!” she demanded with a volley of paddle swats that had me wincing.

“I thought maybe I could give you a spanking, too. Maybe just a little one?”

“Oh really? I’m just supposed to stop spanking you and let you put me over your knee for a spanking? And why would I do that?”

“Well, after the spanking, I thought I could do something to make you feel better. I’d love to lick your cunt, make you cum with my tongue.” The dirty talk got me aroused despite the pain in my ass. “I’d like to run my tongue through your slit and nibble on your lips till you cum in my face!”

The paddle gave her additional strength, and she took full advantage of it as she peppered my bottom with repeated swats to the same spot, giving both cheeks a good beating. She continued as she scolded me about my naughty thoughts and told me how I deserved such a good paddling. It must have been at least fifty swats before she finally stopped.

“We’ll see how far you get with those ideas! Now get up!” She picked up the hairbrush and sat on the sofa again. “Get back over my knee! I’m gonna spank you with the hairbrush,” she said and started as soon as I was back in position across her knee.

Again, she gradually found her way with the brush as she had with the paddle, and before long, I was getting a steady stream of spanks on my already sore bottom. I think she realized she’d been going at my bottom relentlessly with the paddle and then the brush and finally stopped for a while.

“How does your bottom feel now, naughty boy?  Hmm? It's developing a nice deep shade of red!”

“It hurts, Taylor! It hurts a lot!” I replied honestly. “Will you let me thank you properly for spanking me so well?”

“And that would be by licking my pussy?” she asked, and I nodded. “I don’t think I know you well enough to let you put your tongue in my slit!” Being inexperienced in this setting, I hadn’t considered the possibility of STDs and was thankful that she had.

“I’m sorry, Taylor! I didn’t think …”

“That’s right! You didn’t think!” she said, peppering my bottom with a hard and fast barrage of swats with the hairbrush. “Why don’t you get up!” she said and stood up with me. “Think you can make me cum with your fingers?”

“I’d love to try,” I said hopefully.

“Okay, and since you’ll have to pull my panties down anyway, I’ll let you give me a little spanking too!” She took my waist and rotated us in place, suggesting I sit on the sofa and crawled over my lap. “Not too hard now!” she warned as I pulled her skimpy, little thong down.

After gently rubbing her fleshy cheeks, I gave her a very light spank on each cheek. “Mmm, a little harder!’ she said. ‘Only a little harder?’ I thought and realized this was going to be a totally unsatisfying spanking. I spanked a little harder and then a little harder again, but after no more than a dozen swats, she got up and rubbed her bottom as though it really hurt.

Turning to face me, I got my first look at her pussy which had me still wishing I could lick it as she was shaved bare, a tight slit between her ‘Y’ that hid her inner folds with her legs together. Taking her bra off, she was now completely naked as she sat next to me, turned to lie down, and spread her legs as an invitation to explore her pretty little pussy.

Sliding my fingertips up her thighs got a quiet ‘Mmm’ but an audible moan when they slid up her slit and onto her mons, which was a little nubby. Back down to her moistening slit, my fingers teased her plump, swelling lips, already surprisingly wet. ‘She enjoyed spanking me,’ I thought to myself and slid first one, then quickly a second finger into her slippery hole while the other fingers probed for her clit, eliciting a gasp when discovered.

Her squirming hips told me it wouldn’t take too long to make her cum, so I put my thumb to use, pressing hard on her puckered star. “Oh fuck!” she cried as I pressed even harder on it, and between the fingers in her pussy, the pressure on her anus, and a finger flicking her clit, she came as her body jerked in time to each wave passing through her.

“You are a very naughty boy!” she said as she sat up and kissed me on the cheek. “No one has ever made me cum like that without licking me! You weren’t supposed to find my sensitive spot! I think you need another spanking!” she said as she patted her lap.

Smacking my bottom before I’d laid down was a pleasant surprise that continued for several minutes before she stopped and reached for the hairbrush on the coffee table. The pain was exquisite as she spanked even harder, mostly on my sit spots. Apparently, she’d learned quite a bit from her other spanking client, and she put that training to use beating my ass with the brush.

Glancing at my watch, I noticed my hour was nearly up, and I tapped on the watch face to call her attention to it since I was hoping I’d cum before she was finished with me.

“That’s okay,” she said, “I won’t count the time you spent doing me! Why don’t you get up.” I stood by the sofa while she went into the kitchen, came out with a towel, and placed it on the floor, telling me to kneel in front of it and bend over the sofa.

Again, before I was in position, she started spanking me with her hand, except this time, her other hand went to stroke my rigid cock. “Naughty boys, who like having their bottom smacked cum when they get spanked, don’t they?” I just groaned in response to the dual stimulation of being jerked off and spanked at the same time.

“Maybe give you a taste of your own medicine,” she said as she stopped spanking and pressed a fingertip on my tight butthole, which I reacted to at first with alarm but quickly changed to pleasure as she pressed harder and harder until she pushed her fingertip in, and I erupted spewing on the towel.

“Mmm, that was really good, Taylor! I didn’t expect to …”

“You liked that, didn’t you? Having my finger in your butt? Next time I’ll bring some toys to fuck your bottom with! Maybe even a plug while I spank you! I hope there will be a next time!? I enjoyed it too!” she said, running her finger through her slit, remembering the excellent fingering I’d given her.

“Yes, I would like to do this again! I’ll call you?” She nodded her agreement.

I did see Taylor again a dozen or more times over the next year or two before she disappeared. During that time, I got to know her and her rather messed up life living day to day; at times homeless, sleeping in her old SUV with her son, who had learning disabilities she had no idea how to deal with. We’d meet at various friends’ apartments and condos, and even a dirtbag motel on one occasion. I felt sympathy for her and tried to help with both money and advice, but in the end, I wasn’t overly surprised when she was suddenly gone. I just hoped she was alright and alive!

~~~~^~~~~

I hope you like this new episode it the You Need a Spanking saga. Remember to 'like' and/or 'favorite' it if you did. Thank you!