4 - Getting Her Life Together

We were headed to a local bar in my car, where she was apparently a regular, and along the way, I admitted to myself that it was a good idea to have some separation between hers and mine. It rarely works when two people are giving and getting spankings, especially if any role play is involved that implies the spanking is for punishment.

We parked the car, went inside to friendly greetings, and found an out-of-the-way corner booth where we both sat on the same side and could see the rest of the bar and its patrons. We ordered wine, and I realized we’d forgotten the wine she served at her place, getting right to dealing with her oh-so-spankable bottom. The wine arrived, and I got right to the question burning in my mind.

“Taylor, I have to say that you look so good, not just your appearance, but your confidence and even how you walk. I hope it doesn’t sound condescending when I say I’m proud of you!”

“Thank you! And no, you can’t overestimate how far down I was. You didn’t see the worst of it, by the way. I was one step away from being completely homeless, with me and my son living in my car.”

“So, what happened to turn everything around?”

I listened attentively as she told me how desperate she was in the weeks before she started her turn-around, just hanging on by a thread. Then, a cousin offered her a real job at the company he owned but warned her she’d have to be there and work hard. If she did, she’d have a chance to do more and make more money. The situation couldn’t be any more dire, and she knew this might be her last chance, so she took it seriously and was very successful.

She’d managed her life before, but several events conspired to create this downward spiral that she couldn’t find her own way out of. She needed sustained help to get back on track, and her cousin provided that.

She did get in trouble with her cousin once, and when asked what she thought he should do about it, she suggested a spanking! She remembered how much it had hurt when I’d spanked her and thought a real spanking, like those she’d given me, would be painful enough for her to remember the lesson. She said it was very long, very hard, and very painful, reducing her to tears, but afterward she was so wet and horny! So, while it was a deterrent to more bad behavior, it was also the reason she’d called me many months later.

“I’m flattered that you thought of me when you decided you wanted a real sexy spanking. I gather you don’t have a boyfriend to ask?”

“Actually, I do, but I don’t think he’d do it! And I wanted to be sure I really liked it before I even thought about asking him. I figured the worst that could happen is you’d give me a good fingering like you always did!” she admitted and leaned against me, pulling my arms around her.

“Always?” I questioned, “I know I made you cum a few times, but I thought those were just happy accidents, and you were just tolerating me wanting to touch you.”

“Almost every time, Mark! I was good at hiding it. You know you were always so good to me. Most guys didn’t show me the kindness and respect you did because … you know, they were paying for it and were just using me, but you didn’t. Even that first time at that lingerie place, you were polite and so careful about the way you spanked me. That birthday spanking you gave me, twenty-something spanks all on my bare bottom, and when I started crying, you stopped … and I could tell you felt bad about it!”

“It went both ways. You didn’t make me feel weird about what I wanted, whether getting spanked over your knee or fingering your pretty little pussy! Which I’d like to do again right now!” I slid my hand down between her legs, pulling her short skirt up an inch or two as my hand slid up her thigh, reaching for her panties at the top. I love being surprised by a woman with no panties and smiled broadly while Taylor looked up at me, biting her lip as if to say, ‘I’m so naughty!’ when my fingers slid easily through her wet slit.

“Mmm, you are a naughty girl, aren’t you?” I said as a finger slipped inside, and her body tensed. My fingers did what they are so good at, and before long, she was breathing unevenly as she went over the edge, containing her orgasm in this public place. “Do I need to spank you again, young lady?”

“No. No, it's your turn to get spanked! And I’m gonna spank you so good! Let’s go back!”

5- My Turn

So, we left with Taylor asserting her authority with a dozen or so spanks in the parking lot when no one was looking. We were back at her apartment in minutes, and once inside, I was instructed to take her skirt and blouse off, which left her naked once she’d slipped her sandals off. She did the same to me, except for my underwear, and with my pants pooled at my ankles, she turned me sideways and spanked me hard enough to sting.

“Now, let's see what kind of toys you brought me,” she said, going to the backpack I had used before to carry my implements of ‘ass destruction.’ “Okay, the hairbrush. Ooo, what’s this?” she asked, pulling out a small round paddle with large holes drilled around its edge.

“That’s a new one I just made. You’ll be the first to use it!” I said, hoping it sounded like a privilege.

“Oh, I like that idea!” she said, smacking it against her hand and then her butt. “Does it hurt a lot?

“We’ll see, won’t we,” I replied vaguely, though I knew it hurt quite a bit used on myself, but in the hands of another, I was sure it would be even more painful.

“A bottle of lube, which means there must be a … there it is!” she said, pulling a new anal toy from the bag. “That’s different!’ she commented on the shape of the prostate stimulator.

“Well, you have been a bad boy, haven’t you? First, thinking about all those naughty things you wanted to do to my body, and tonight, you did them, didn’t you? Yes, you did, so you’re gonna get spanked! I’ll put you right across my knee for a good spanking!” Taylor knew I liked hearing the word ‘spank’ in all its forms, especially when threatening me with one.

Placing all the toys, including the paddle I’d used on her, on the coffee table, she sat on the sofa, pulled me down onto her lap, and began spanking immediately. Incorporating the dirty talk about what we’d done into more threats of how I would be spanked mercilessly and left with a sore bottom for days had my dick hardening still, and I imagined she could feel it against her thighs.

After at least a hundred warm-up spanks, my underwear was yanked down and off, which led to a new pattern of spanking and paddling. Starting with five good smacks in a row on each cheek, she changed to the large paddle with the same pattern, then the hairbrush, and finally the new paddle. After a short rest, she repeated the pattern with ten on each cheek, which had me squirming when she got to the new paddle. Oh, and that new paddle was likely to become my favorite. Though lightweight, it packed a real sting, and the weight allowed the user to swing it even more forcefully.

A longer rest this time, during which I was treated to having her fingernails scraped roughly across the most sensitive spots on my now-red ass. My back arched, and my body stiffened in reaction to this most pleasant torture.

“Fifteen this time!” she warned and began the same pattern, and only halfway through the hairbrush, she had me writhing and trying to escape the punishment I still wanted. Another rest with more fingernails and a fingertip pushing into my bottom prepared me for what would come later.

“Oh fuck, Taylor! This is so … so … just spank me!” A devious laugh preceded the resumption of the pattern, now up to twenty at a time, which I loved with her hand but accepted as my fate when she started with the implements. I loved this pattern and resolved to remember and use it myself, though it would have to be someone who could take it. For those who aren’t counting, this amounted to four hundred spanks in fairly rapid succession, not counting the warm-up! And she wasn’t done yet!

“Mmm, that was nice!” she said, and though ‘nice’ isn’t the adjective I’d have used to describe it, I wasn’t complaining. My bottom felt as good as it ever had after being spanked, and from Taylor, that was even more of a surprise.

While she’d had spanking experience with this other client, she handled me unlike all other spankers had. She asked me what I wanted, taking suggestions on both positions and implements. The only things she decided on her own were when she’d get her ‘play’ spanking and when I’d finger her pussy. Otherwise, she didn’t just allow ‘topping from the bottom,’; she encouraged it. Clearly, she’d learned the error of her ways.

“Don’t think I’m done with you!” she warned. “There’s a lot more spanking to come! Now get up,” she instructed, adding, “Follow me,” when I stood. I saw her grab something from the table and disappear into a short hallway to her bedroom. Sitting on the end of the neatly made bed, she called me to her side.

“Back over my knee, naughty boy! You’re getting a nice, long spanking, and just because I’m only using my hand, don’t think it won’t hurt!” Again, I was barely in position when her hand rained down on my already well-spanked bottom with a ferocity I’d not felt with her before. Had she used this much force with an implement, I’d probably be screaming, but as it was her hand, the intense pain was delicious, especially with her repeated scolding about how much I needed this spanking and how she’d spank me until she wore my bottom out.

I have no idea how many she gave me this time, and frankly, I didn’t care as it left my bottom with the most incredible soreness that I knew I’d be feeling most acutely for hours to come.

“How was that?” she asked softly. “You liked that spanking, didn’t you? Hm? … but you always like it when I spank you with my hand! Mmm, I liked it too! But we’re not done yet, and I think you’ll love what’s next. C’mon, up!” Standing up, my hands went right to my cheeks, only to be swatted away by her hand, prompting another series of hard smacks to both sides. “Get on the bed on all fours,” she instructed.

Getting on the bed herself to kneel at my side, she took my hard cock in hand and stroked, but only for a few seconds. I knew what was coming next when I saw her reach for the bottle of lube and closed my eyes, preferring just to feel what would come after the slippery liquid dripping onto my tight hole and her fingers smearing it around and into my ass.

When I heard the bottle cap snap shut again, I assumed she was coating the dildo as well and knew I’d be feeling its intrusion quickly, but she surprised me again by spanking me with her dry hand. She was just finishing when I felt the pressure of the toy being pushed slowly but relentlessly into my bottom. Once fully inserted, she just let it sit there, providing that wonderful feeling of fullness, as well as the stimulation from an extension that pressed on my perineum.

She seemed to know that you didn’t stroke in and out of the bottom with this but instead just squirmed it around inside, pushing and pulling it only a little to reach the sensitive prostate. Using it by yourself, you’d clench your cheeks slowly, and the specially shaped tip would provide the desired stimulation. Taylor added to it all by stroking my cock with her left lubed hand while her right alternated between spanking me and manipulating the plug in my ass.

It wouldn’t be long now, and my writhing body passed that information on to her. Leaving it in my ass like a giant butt plug, she stroked me with one hand and spanked me with the other. I’d never felt anything quite like it and was gasping as I tried to hold on as long as possible before I finally erupted and fell to my side on the bed while the shuddering climax crashed over me, enhanced by clenching on the stimulator.

“Wow!” she cried as she gently caressed various sensitive areas. I was still breathing unevenly when she started working the stimulator in my ass again. “Lay on your stomach,” she instructed and alternated between rubbing my sore cheeks with single, extremely hard spanks. Stroking it in and out maybe an inch, it started working its magic again, and combined with the rubbing and spanking, I was starting to get hard again.

“Up on your knees again,” she instructed as my body again betrayed its arousal. Repeating the prior performance but with exaggerated movements in all areas. She’d stroke my cock with a slick grip, tease my ass with the toy, and spank me as hard as she could, eventually bringing me to another convulsive climax as Taylor held me close, pulling me in against her tight body.

“Holy shit, Mark! You’ve never cum like that with me before!”

“Taylor, I’m not sure I’ve ever cum with anybody like that before. How did you know what to do with that anal toy?”

“I did some studying the past few days,” she said with an innocent smile. “I wanted this to be very special for you because of how nice you’ve always been to me and because we can’t do it again.” This last statement was disappointing, though not entirely unexpected, as she had mentioned a boyfriend.

“Your boyfriend?” She nodded. “He doesn’t know you’re here, does he?”

“Actually, he does. He knows about my past and your part in it, so when I started hinting around about doing this with you, for you, he was okay with it on two conditions. One, that I didn’t let you fuck me, and two, that it would be only this one time.”

“Oh,” I said, my disappointment evident.

“Yeah. This was special! I enjoyed every bit of it, and you have no idea how much I want you inside me right now, but …”

“I understand. Would it be okay if I licked you one more time?” I asked and saw a smile creep across her face, her answer obvious. Turning to lay on my back, I said, “Why don’t you sit on my face!” She wasted no time straddling my body and pinning my arms to my sides, limiting me to using my tongue only.

The taste of her prior orgasms lingered as my tongue went to work, slowly building her excitement as she squirmed on my face. Riding my face like a galloping horse, my tongue licked from her anus to her clit and worked at a fever pitch to bring her to the most intense orgasm of the night, or should I say orgasms, as when she came, she sat hard on my face with my tongue still licking and making her cum again and again. Even when she tried to get up, my hands pulled her back down to get a few more licks in while watching her body jerk spasmodically.

“Oh my God!” she cried when she could breathe again and mashed her lips onto mine as our tongues danced together.

Finally, getting up and dressed was a sad process for both of us. I imagined I could make her break her promise to her boyfriend, but I wouldn’t be the one to screw up any good thing she had going now. I picked up all my toys, getting a knowing smile from Taylor when I put the stimulator in the bag with the other items to be cleaned later.

It was time to leave, and tears ran down her face as we hugged at the door. I wiped a few away with my thumb, and she gave me a sad smile.

“You were supposed to make me cry when you spanked me, not when you left.” We kissed once more, and I walked out the door. Looking back, she was still standing in the doorway watching me walk away, and very briefly, I wondered if she was having second thoughts, but then she stepped back and closed the door.

~~~~^~~~~

Well, she showed Mark how much she's gotten together! I hope you enjoyed Taylor's story! Please remember to 'like' and/or 'favorite' my story if you did! Thank you!