Doesn't Hurt to Ask

She came across as being kind of wholesome or innocent. There was some truth to it. She'd had a few boyfriends before me, but was definitely the "relationship type" and had never had a one-night stand. She told me that she had never looked at dating as just "having fun," it was always to find someone compatible for a long-term relationship. She was in her late twenties and was ready to get married and have children if she met the right guy. I was honored that she considered me a contender.

I was somewhat less innocent. I actually hadn't been with that many women, but there were a few hookups and casual flings in there. I'd also not long before sought out and found a few women who shared my particular proclivities, though we didn't have much else in common. I'd gone back to the original plan of just get a girlfriend first and then try to bring up the kinky stuff once we got to know each other.

We'd first slept together around the fourth date I think, and had been seeing each other for a few months now. I'd mentioned spanking at one point and she didn't think anything of it. I didn't expect her to - she wasn't all that innocent, and it's not that weird of a thing to be into. But up to this point I had only ever given her a few light, playful spankings with my hand.

I was a little hesitant about telling her everything. I was sure she knew I was a nice guy and would never really want to hurt anyone, but I guess I was afraid it might sound a bit harsh or sadistic to her, given her lack of background with this sort of thing. There was always that little bit of fear, when I really put myself out there, what if this woman I'm close to now is horrified that I'm turned on by this?

But the moment felt comfortable and I went for it. Snuggling in bed late one night, the subject had come up. She had always been perfectly agreeable to the idea, but I knew that she didn't really quite get it. It wasn't her fault. How could she know, if she wasn't wired that way? It was on me to try to help her understand exactly what it was that I wanted, what really did it for me.

So I ended up just narrating through, in detail, a particular scenario of something I would want do with her. I assured her that I wasn't expecting it, I knew it was a lot to ask, and that I was happy being with her even if she never wanted to. I meant all that too. The most important thing for me was being able to be honest with her, and be able to share this part of who I was and have her really know me.

She was obviously turned on listening to me talk about it. Something about erotic storytelling just seems to appeal to women, hence the popularity of those romance novels I guess. I wasn't even quite done with the story when she said sure, she would do it! I guess I went into it expecting a harder sell.

So it was agreed we would do it sometime, but no specific plans were made. It was late, and we soon drifted off to sleep. But my mind was going now, I was eager. I would seize this opportunity. She didn't know it yet, but I was thinking the very next day.

We were meeting some friends for brunch at noon. We slept in a little and then had a small bite to eat just to hold us over. We puttered around, took our showers, and got ready.

All morning, nothing had come up in conversation about the night before. It was about the only thing on my mind of course. She probably wasn't thinking about it at all, maybe had almost forgotten about it.

Of course it wasn't going to come up at brunch either, being with other people and everything. I felt myself not being very engaged in the conversations at brunch, just too preoccupied. I had a plan now, and started to feel anxious about it going well. Fortunately one of our friends had a lot to say about a recent trip, so it was easy enough to withdrawal a little and just eat.

We didn't have any particular plans for the rest of the day. In the car on the way back, we talked about possibly walking around downtown, maybe a movie later, should check online if there were any events going on. I nodded along and didn't strongly suggest or agree to anything yet.

We got back to her place and I went straight to the bathroom, the one beer from brunch apparently having caught up with me. After washing my hands, I lingered and looked at myself in the mirror. I felt butterflies in my stomach. I gathered up my resolve and opened the door.

Walking into the next room, I approached from the back and the side as she was sitting at her computer. She was absorbed in scrolling through Facebook posts and didn't even seem to see me coming.

"Hey... so that thing we talked about last night..." I said. She turned her head and saw the expectant look on my face.

She looked confused for a second and then I could see it dawn on her. "Oh!" she said with a nervous giggle, "wait... you mean like now?"

"Seems like as good a time as any, we don't have anything else going on," I said with a little shrug of the shoulders, and waited for her reply.

I could already feel my persona shifting. That was the interesting thing about all this - I was not exactly a dominant, take-charge personality type in general. Probably more like the opposite. I mean, I had a reasonable level of self-confidence, but I could be described as quiet, reserved, agreeable. I was kind of a sensitive guy, and I think she liked that about me. And yet...

"Um... Ok!" she said, brightening a little, standing up from the computer and turning towards me, arms hanging at her sides, looking unsure how to proceed.

"I'll be right back," I said, starting toward the sliding door that opened to the deck.

Her townhouse complex backed up to some woods with a small stream. I walked toward the stream, then continued parallel to the bank, scanning around. I made quick work of it and hurried back before the mosquitos discovered me.

She must have gone back on Facebook while she was waiting. I saw her stand up again as I walked in. Her eyes went to the slender branch I was carrying in my right hand by my side. It was two to three feet long, less than a half-inch in diameter, freshly cut green and flexible wood.

"Ooh..." she said apprehensively, leaning back a bit, as if trying to get further away from it, as I set it down on the dining room table.

Her place had a sort of open floor plan, where the dining room and living room were just one big room. I pulled out one of the dining table chairs and turned it completely around so that the back of the chair was up against the table and the seat faced out towards the open living room area. Then I picked up the switch and took a few paces back from the table and chair.

She looked confused for a second. "Oh, ok... I thought we were going to the bedroom."

"No, this will do," I said. "Ready?"

"I guess!"

She said it with a nervous smile, but nonetheless seemed to have some genuine enthusiasm, like it was an adventure. Those Fifty Shades of Grey books had been something of a cultural phenomenon not long ago, it seemed like every woman was talking about them for a while. Perhaps I flattered myself too much, but I imagined that part of her thought it was cool that she was actually doing something like that for real, and that it made me more interesting to her.

"Get undressed," I said. I was getting into it now.

She hesitated, and looked at me as if seeking confirmation. Maybe she was still adjusting to the idea of being just told what to do, or maybe she felt self-conscious about stripping in front of me. Sometimes women are funny like that about their bodies. Obviously I'd seen her naked plenty of times and she had to know I loved her body because I lavished kisses and caresses and compliments on her. In any case, she knew this was part of the plan.

"You can leave your clothes on the couch," I said, pointing to it.

I loved ordering a woman to take her clothes off and having her comply. It was one of my favorite things in the world. And honestly, whatever the cause, her reluctance made it even better.

First she pulled her top off over her head, throwing it onto the couch. Then she turned away from me to unfasten her bra, which she slipped out of and tossed aside as well. I was focusing on the sexy little curve of her hips at her lower back. She bent over to undo the straps on her sandals, then kicked them off. She had her toenails painted this sort of lavender color.

She turned back toward me, flashing a shy smile, her cute petite breasts standing at attention as she unbuttoned the top button of her snug jean shorts. She wriggled side to side to work them down over her wide hips. As she stepped out of the shorts I took in the view of her invitingly ample thighs, with her light pink cotton panties hugging the contours in between.

I just stood watching, holding the switch, flexing it occasionally. Looking away, she quickly slipped the panties off too, and as she turned to add them to the clothes pile I got my first glance at her bare bottom. It was round and full, very feminine. I felt a twinge of excitement imagining the switch cracking across those pale, plump cheeks. So soft and sensitive, just asking for it.

With her fully nude, standing in her bare feet, and me having clothes and shoes on, she looked deliciously vulnerable. She was tall for a woman, about five-foot-eight, a little taller than me in fact. It didn't bother me, and I don't think it bothered her. In fact I kind of liked it, I felt like getting a taller woman was something of an accomplishment. And I was a lot stronger than her, for one thing, so I certainly wasn't intimidated.

Nonetheless, height is associated with physical dominance in a lot of people's minds, and I got extra pleasure from it being reversed now, having this tall girl so obviously under my command.

"Ok... like we talked about, you're going to get ten strokes, and I want you to count each one," I said. "Bend over and put your hands on the chair."

After a deep breath she took the couple of steps towards the chair. She stood squarely facing it and gracefully folded forward, letting her palms rest on the seat.

I took an extra step back to survey this beautiful scene. A naked woman bent over, presenting her bare bottom to me. The anticipation was the best part, I took my time and let it build.

Finally I stepped forward and off to her side. I held my arm out with the switch, moving my feet here and there, making small adjustments, trying to gauge just the right angle and distance. I tapped the switch lightly across her bottom a couple of times.

She turned her head and watched me anxiously. "Look straight ahead," I said, with a little sideways nod of my head. "Hold still."

I felt a certain seriousness and determination come on, as I turned my arm and shoulder, drawing the switch far back. Keeping my eyes firmly fixed on the target, I sent the switch whistling through the air. I loved the sound it made. It landed solidly with that satisfying "thwack."

She bolted upright, turning to face me, hands shot back to her bottom, and she just froze, mouth open, speechless for a second until all she could come up with was "Oh my God!"

In that moment she seemed to completely lose any previous consciousness of being naked. I found myself distracted for a second, just staring, appreciating the incredibly cute little lips peeking out between her legs.

I got myself refocused and looked her in the eye. I said in a stern but slightly playful tone, "What number was that?"

"One! Ow... Oh God..."

She would end up taking the Lord's name in vain quite a few more times before all this was over.

"That was an absolutely adorable reaction," I told her. I paused for a second, smiling, taking in the possibly exaggerated look of wide-eyed distress on her face. "Mmm... that really stung didn't it?"

"Ugh... I don't know if..."

"Let me see," I said, turning her to the side a little. "Ooh... I got you good!" I said proudly, running my index finger lightly along the raised pink stripe.

I stepped back, glanced at her, paused briefly, then gestured toward the chair with the switch. "Back in position."

She hesitated, and I could see the look on her face slowly turning from disbelief to resignation that yes, I really was serious, she wasn't getting out of this. I saw a tiny bit of a smile though, as she shuffled over in front of the chair. She flipped her hair out of the way as she slowly bent back over.

I felt a sense of relief mixed with a flutter of excitement. I had a moment of real concern that she might actually bail out. But now it was really happening. It was on, she was submitting to it.

I felt a strange growing sense of power. I looked down at the switch, it felt good in my hands.

I paused once again to admire her curvy body, made extra sexy with the addition of that deepening red stripe. I liked being able to make her wait, bent over, obediently, for as long as I wanted.

I got myself set up again. "Straighten your legs," I said firmly, tapping the switch on the backs of her thighs.

Being limbered up and more at ease now, I didn't seem to have to think about the mechanics of the stroke so much. The switch just glided naturally in a fluid motion. It felt effortless, and the sound seemed a little higher pitched than before.

She was more prepared for it this time. It struck lower, right on that delectable little undercurve of her bottom just above where it meets the tops of her thighs. She cried out and kicked one leg up and back, showing the smooth sole of her foot.

"Two!"

She stood up and was shifting her weight from one foot to the other, trying to shake it off. She took a couple of quick breaths, with pronounced exhalations. I loved watching a girl struggle to get through it.

"Ow... " she said, laughing a little. She twisted to get a glimpse at the mark it left. "Oh God it really hurts!"

"This is what happens to bad girls," I said, really having fun with it.

"Uh, I'll be good..."

When she got into position the next time she did it without hesitation. She planted her feet, and had her head up and back arched. There was an air of confidence now, as if to say ok, let's do this, I can handle it. I knew she was a strong woman, and that women in general were pretty tough. They weren't fragile. They just give you that damsel in distress routine sometimes, and don't get me wrong, I like that too.

I got into the groove now, delivering the strokes at a slow pace, allowing plenty of time for each one to really sink in. I tried to spread them around and cover her bottom thoroughly, having to be increasingly precise as it went on.

She was vocal throughout, and she twisted and flailed every which way you could imagine, which I found delightful. But she was a trooper. She always remembered to count and mostly stayed in position. I did have to tell her to stop stalling a couple of times, and at one point warned her that she could get extra if she wasn't cooperative. It was an idle threat, but I liked saying it.

We finally came to the last one, number ten coming up.

"Not too hard..." she said, trailing off.

"I'll decide."

She wasn't getting off easy. The last one wouldn't be extra hard or anything, just the same firm stroke as all the others. I looked carefully and didn't see any spot that I'd missed, so I just casually let it fly. I savored the final swish and crack of the switch, and the final squirm and squeal from my girl.

"All done!" I announced.

She stood up and stepped away from the chair. Now she had a broad smile on her face and I could see her looking very relaxed. I can be certain that she felt relief that it was over, but there also seemed to be a sense of accomplishment at having been able to take it and not giving up.

I approached and wrapped my left arm around her lower back, pulling her naked body next to me, feeling her breasts against my chest. With my right hand I lightly took hold of a fistful of her hair. "Thank you for that," I said, and gave her a long kiss.

I pulled back and took her by the upper arm. I wasn't done with her yet. I walked her into the bedroom and she followed along without a word. When we got to the edge of the bed, I gave a little nudge and she scrambled up and laid on her back.

I quickly stripped off my clothes and made my way onto the bed, kneeling facing her. I took hold of her ankles and lifted her legs straight up, examining her wonderfully welted bottom.

Then I let her legs fall to the sides and let my fingers lightly explore in between, opening her up a little. I noticed she was quite aroused. "Hmm... I guess you liked it," I said teasing, "maybe I should give you a few more?"

"No!" she said laughing.

I slid forward and entered her. It probably didn't take very long. I kissed her neck and started replaying in my head everything that had just happened. I don't think I'd ever been more turned on. She was pretty worked up by now too, and I made sure she was taken care of. When we were all done I told her to roll over on her stomach so I could put some lotion on her.

She said later that there was something about all this that she found kind of sexy, even though it really did hurt a lot. She was surprised about this dominant side of me that came out, it was something she hadn't expected, and she liked it. We stayed together, and she knew what she was getting herself into.