I squirmed in my seat. Did she really just say that?
Claire sat across from me in the booth, smiling. Her thick black curls fell to her shoulders, untamed. Her red lips were full and inviting, just like the cleavage revealed by her low cut red sweater. She wore a calf-length flared black skirt that flowed with the sway of her hips. Her come-fuck-me heels were amazing. I noticed all this…because I’m a metrosexual.
At 40 I was fit, had all my thick brown hair and was a little better looking than average. My intense blue eyes could still charm the women and I dressed my slender frame well. Tonight I wore pressed khakis and a white dress shirt rolled up to the elbows. My leather loafers matched my leather belt. I wanted to impress Claire.
This was our third date. We’d met on a kinky website that was full of people with every kind of sexual preference imaginable. I didn’t want to do it all…I just wanted to indulge in a little sexual research.
The one thing I knew I wanted to try was…not being in charge. I’d been in charge the last 20 years. It was a good time. But one night porn surfing I came across some stuff where the women were in control.
I got hard as a rock and could not walk away from the computer. Hours were spent that night poring through every femdom porn site I could find. I realized that I’d been in control not because I’d preferred it that way, but because it had been expected of me.
I decided it was time to try something different.
Claire liked being in control. Her profile said that and I believed it. There was an air about her that was so confident and sure. Confident that I wanted her…which I did. And sure that whatever she wanted, not only would I do her bidding…I would enjoy it. This was all a fantasy in my head at this point, though, because so far we’d had dinner twice and our conversations had not delved into sex.
Claire shook my hand after our first date ended and directed me to call her the following Thursday at 6 o’clock. She was so specific. It was odd. But I called precisely on time and she praised me for it.
“Good boy, Lionel.”
I hadn’t been called ‘boy’ in years but coming from her I liked the way it sounded. We talked for a while and set up another date.
After the second date she asked me to walk her to her car. Arriving there, she leaned against her door without opening it and crooked her finger at me.
“Come here, I want to kiss you.”
No woman had ever taken charge like that. They always waited for me to make the first move. I found it refreshing…and unsettling; a fascinating combination. I was trembling when our lips met. Her hand came around the back of my head and grabbed my hair, using it to keep my lips attached to hers while she consumed me in a long, deep kiss. Jesus. I get hard right now thinking about it. Again she told me when to call her, the day and time. Again I complied and was praised.
“Good boy, Lionel.” Why did hearing her say that feel so damn good? At 40 I was hardly a ‘boy’.
Tonight our conversation was a little more probing. Claire tried to talk with me about what I was looking for sexually. That was tough for me because I had just discovered new parts of myself that I didn’t understand yet. How could I know what I wanted when I wasn’t clear on what my choices were? I just knew that the idea of a woman in charge in the bedroom thrilled me. Claire smiled when I said that during our second dinner.
“Don’t worry Lionel, I’ll take good care of you.” What an interesting thing to say. Yet the reassurance felt nice. I liked the implication that it would be safe to let her be in charge.
Claire’s dominance was quiet and under the surface, not like I thought it would be. In the porn I’d watched, some of the women were just plain mean. I didn’t want mean…I just wanted to let her run the show and see what happened. Maybe run me…sort of. To see if it felt as good as I imagined it would in my fantasies. The idea of a being with a dominant woman had me hooked like a dog after a bitch in heat. I felt powerless to walk away.
So there we were, sitting in an elegant Chinese restaurant, sharing another meal. Our third date. I was highly anticipatory. What would happen this time?
I could tell after we ordered that Claire was up to something under the table. She leaned forward and came back up, extending her closed hand out to me…holding something red. I took what was offered and suddenly blushed furiously, dropping my hand to my lap. It was her panties! She smiled wickedly at me. And said the words that made me squirm…
“Go to the bathroom, Lionel…and put them on.” Her voice was soft yet dripping with authority.
I felt my eyes widen at her request. I hesitated. Seriously? My expression silently asked the question. She nodded calmly. Without looking at my hands in my lap, I gathered the edges of the panties and tried to hide them in my fist so no one would see me carrying them.
“Yes Ma’am.”
Claire smiled at that. I slid out of the booth and went to the bathroom. Thankfully it was empty, but I went into a stall anyway. It took me some time to slip off my shoes, take my trousers and my briefs off, slip into Claire’s panties and put everything back on. But it was more complicated than that. It also took time to examine the soft red satin panties with black lace edging, time to slip them on slowly, feeling the fabric stretch against my cock, and time to calm down a bit so I didn’t return with a raging hard on.
I decided to leave my briefs in the stall. There was no way to carry them back to the table undetected. I grimaced at the loss of a pair of Calvin Kleins but there was nothing to do for it.
As it was, I felt like everyone in the restaurant knew what was under my pants as I walked back to the booth where Claire sat, watching me intently. My cock was half hard and grew quickly after I sat down, as if it knew that now it was hidden and safe.
The long white tablecloth hid almost everything. It hid Claire’s stockinged foot placed gently in my lap…right on my erection. Rubbing it. Stroking it with her foot. I could feel my cock begin to leak with excitement.
We ate dinner and talked as if nothing was happening under the table. The Honey Sesame Shrimp was always delicious at this restaurant but I hardly noticed. Claire’s foot pressed the satin against my crotch over and over again. It was so hard to sit still, so hard to know what to do, except let her play with me. It was fucking hard. And I loved it.
She kept me hard even right up to the point we got up to leave, necessitating a hand in my pocket to control my cock as we walked out the door. I wanted to fuck her so bad I could practically taste it. But I was not running this show. Claire was.
I walked her to her car. She’d parked in the corner of the large lot and we were well-hidden between her SUV and a wooden fence. She pushed me gently up against the side of the car and unzipped my pants. They were still fastened at the waist. Her slender hand slipped inside and caressed my cock through the panties. They were wet with my desire. I leaned into her hand, longing for release.
But where – here? In the parking lot? I couldn’t imagine…but Claire could.
She unbuckled my belt and slipped it out of the loops with an alarming snap. Then she unbuttoned my pants and pushed them down, exposing my cock in those lovely panties. She turned me around and I stumbled just a bit with my pants around my ankles. Crap, I hoped no one could see us.
“Grab the luggage rack, Lionel.” So much of our dance had been happening in silence that her words startled me a bit. I reached my arms up and did her bidding. I felt vulnerable, exposed, embarrassed…and so fucking turned on.
“Yes Ma’am.”
Claire pulled those sweet panties up between my cheeks to expose my ass. I watched as she doubled my belt, paused and looked me right in the eye.
Whoa – I hadn’t counted on this. Well, to be honest I hadn’t counted on almost anything that had happened so far tonight. Claire’s deliciously erotic way of keeping me slightly off-kilter was about the hottest thing I had ever encountered in a woman. Even looking at that belt in her hand – her intentions clear – I had no desire to stop her. I wanted whatever she had to give me. My hands tightened on the metal bar with anticipation.
The loud crack of the belt alarmed my senses almost as much as it took my breath away with pain. Right after the stroke of the belt, Claire reached around and squeezed my softening cock, coaxing it back to full mast. Then another stinging stroke. Jesus. I was sure she was leaving marks. It was intense! I scanned the parking lot reflexively and felt another stroke, even harder. I cried out a little with that one. Was I enjoying this?
Once again her hand played my cock expertly and my answer was immediately yes. This time she reached into the panties and grabbed me. I felt her finger slide around the head, playing with the wetness. My mind blurred with the combination of pleasure and pain.
Claire stepped back and swung the belt again, three times in quick succession. I gasped and tried to muffle my cries. My hands almost came off the bar to cover my ass; protect it. I stopped myself. I wanted to be a… ‘Good boy’. So I held on even tighter in an attempt to please her.
Her hand caressed my hot sore cheeks. Then she slid her fingers underneath, stroking my balls lightly through the panties. I almost cried with relief. She moved away and I braced for another stroke that never came. She opened her purse. The next thing I knew the panties were being pulled aside and her lubed fingers were rubbing my asshole!
Honestly, it thrilled me. Ass play was something I’d explored myself but never had the courage to ask a partner to try. The partners I’d chosen were not adventurous enough to suggest it, either. Well that had obviously changed.
Claire’s intentions were clear, once again. Her fingers were insistent. I tried to relax and felt one finger slide deep into my ass. Oh Christ that felt good. Her pace was just a little too fast and that felt intentional. Not giving me time to adjust, she pushed another finger in and I winced at the invasion but still had no urge to stop her. I made one soft mewling sound that spoke of vulnerability and intensity and my struggle with her pace. She left her fingers buried in me and stroked my prostate. Immediately pleasure shot through my pelvis and I swooned. All too quickly her fingers were gone and replaced with a cool surface pushing into me. It felt bigger than her fingers.
“Oh! Claire, please!” My words asked for time to adjust.
Claire sidled up to me and put her lips at my ear, kissing it softly and giving me chills. The pressure on the plug never lessened.
“Relax, Lionel. This isn’t even my largest plug.” Her voice was rough with passion. She took the hand that was not holding the plug and lifted her skirt, reaching towards her pussy. I wasn’t sure what she was doing because most of my concentration was focused on relaxing and letting in her toy.
“Open your mouth.” Immediately I obeyed. Her fingers slipped inside. They were dripping and delicious. The earthy, tangy flavor of an aroused woman; incomparable.
“You can do it, Lionel….”
I pushed out and my sphincter opened up a little more as I sucked on her fingers. Claire kept the pressure on and I felt the toy stretch me even further and then slip inside. I felt a huge sense of relief as my ass closed around the smaller diameter. It was heavenly.
Suddenly I was sensitive, emotional. I had tears in my eyes. Why? I didn’t know. From my ass finally opening up to take the plug…or maybe it was the way she’d kissed my ear so gently…or the hot burning where she’d whipped me…or her fingers back on my cock. Fuck, I think it was all of it.
My cock was swollen and heavy with wanting.
Claire picked up the belt again and lashed it across my ass…four times. It didn’t hurt as much this time. I actually felt it jostle the toy, sending thrills deep into me. Then she turned me around and my fiery ass touched the car. The cold metal felt good. I had to let go of the rack to turn and I didn’t know what to do with my hands. Claire did.
“Put your hands back on the bar, Lionel.” I reached up and back – it was a little awkward but I could do it.
Again I wondered what I’d gotten myself into.
I was in a fucking parking lot with a plug in my ass, getting whipped, cock raging and my pants around my ankles. Claire slid the soft panties down to be with my pants.
In that moment there was really no other place in the world I wanted to be than right there doing exactly what Claire told me to do and letting her do anything she wanted to me. Irresistible. Way in the back of my mind somewhere I hoped to God we didn’t end up getting arrested.
Claire pulled up her skirt and tucked it in the waistband. In the dim light of the parking lot I saw her dark triangle of pussy hair and I wanted to touch it, taste it, and smell it.
I watched as Claire slid my belt around my bare waist and buckled it. She pulled a condom out of her cleavage, ripped it open and slid it down over my cock in movements so smooth it made my head spin.
Then she climbed aboard the Lionel ride. Our bodies fit perfectly. Claire’s long legs and height gave me the perfect angle to slide my cock right up and into her startlingly slick cunt.
Amazingly slick, actually. Claire was obviously getting off on all this just as much as I was. She whimpered a soft cry as my cock slid into her. I was proud of my cock. It was plenty long enough to fuck standing up and thick enough to satisfy, or so I had been told. I thrust deeply into her and realized how fucking turned on I was. I needed to dial it back a bit if I was going to last for her.
“Lionel?” Her voice was breathy. “You may not come until I give you permission…do you understand?”
“Oh, yes, Ma’am.” I started the self-talk in my head that I use to delay orgasm. I was surprised that it worked at all because Claire had me so turned on for so long that my balls ached with need.
She worked herself on my cock, using it for her pleasure, using the belt to pull me hard and deep into her rhythmically, exactly the way she wanted. Soon I felt her stiffen and heard her squeal softly. Her cunt gripped my cock with her spasms.
Just then, A soft click nearby made me look in the direction of the sound. A few cars away a man had unlocked his door and he stood in the semi-dark, watching us for a moment. There was a lot to see. I saw him gesture a thumbs-up before silently getting in his car and driving away. He waited until he was almost to the street before turning on his lights. The consideration of a stranger. I hoped we had made his night.
Clair trembled as her remaining spasms had their way with her body. I let go of the bar and held her tight against me as she came down from her orgasm. Just seemed like the right thing to do.
After a bit, she tilted her hips and came off my cock. She untucked her skirt from the waistband and let it fall, covering her lovely lady parts once again. The condom was pulled off and thrown on the ground. Her hand grabbed my cock and stroked it, still slick from the lube in the condom. Standing at my side her other hand took the base of the plug in my ass and jiggled it. I moaned into the soft night. Good God this woman was going to drive me absolutely fucking bat-shit crazy before she let me come, I just knew it.
“Hands back on the bar, Lionel.” I obeyed.
She began to push and pull the plug a little while she worked my cock, carefully avoiding the head.
“Do you want to come now, Lionel?”
“Yes Ma’am. Please, may I?”
“No…You may not.” The words twisted inside me a little…in a not entirely unpleasant way.
Claire pulled on my cock and teased my ass with the plug until I was certain I was going to come without her permission; I felt it start. Then she abruptly bit my nipple, hard! The pain of it put a road block up for my orgasm as if by magic.
Then she began pushing the plug in deeply and quickly with short strokes. She was fucking nailing my prostate. I wondered if it were possible to pass out from pleasure.
In that moment I heard the words I had been waiting for all night, even if I hadn’t known it.
“Come for me, Lionel. Come for Claire.”
Her hand sped up on my cock and slid over the head with each stroke. She continued plug-fucking my ass. It was all too much. Insanely, astonishingly, almost violently too much…in the very best way possible.
I came with an intensity I’d never experienced before. I yelled and didn’t care who might hear. Each spasm grew more and more intense as did the volume of my cries. Hands still on the bar I watched the come shoot from my cock in ropes that traveled four feet to the wooden fence next to the car, making Rorschach designs of come. It felt like I came forever. I kept thinking it would stop but her hands seemed to know how to coax one more spasm out of me over and over again.
She could tell when I needed her to stop. I didn’t have to say anything. My legs were trembling and I was glad I had the bar to hold onto at that point, even though my shoulders ached a little. Claire let go of my cock and the plug and moved in front of me. She wrapped me in her arms and kissed me in that amazingly gentle way again, not caring about come or lube or anything as her body pressed against mine.
“May I let go now, Ma’am?”
“Yes, you may.” She practically purred the answer.
I let go of the bar and hugged her close, kissed her deeply.
“Good boy, Lionel.”
The words thrilled me to my core. She kissed me again. And then began giving me instructions.
“You will leave that plug in for your drive home. When you arrive, take it out and clean it. Then take a long hot shower. When you get out, put some lotion on your ass in these spots.” She touched my sensitive ass cheeks. They felt a little bruised and I couldn’t wait to get home and look in the mirror to see if they really were. Bizarrely, I was excited at the prospect.
“Call me on Wednesday at 7 o’clock. You do not have permission to have any orgasms before Wednesday. We’ll talk about when your next orgasm will be at that time. Is that clear?”
“Yes, Ma’am. Quite clear…I look forward to it, Claire.” I pulled the red satin panties and my pants over my hot ass cheeks. Buttoning, zipping, tucking my shirt in, replacing the belt through the loops and buckling. All of those movements seemed a little surreal after what I’d just been through. In a fucking parking lot!
Before I left, I took Claire back in my arms and kissed her sensuously; meeting her tongue in lazy circles…I gave her one of my best.
“Goodnight, Claire.”
“Goodnight, Lionel.”
I walked back to my car several rows away. With each step I could feel the plug in my ass and the soreness of my whipped butt. My cock began to stir again at the sensations.
It was Saturday night. Wednesday was already an eternity away. And even then, she might say no! I knew I could cheat and jack off when I got home to the vivid memories of everything Claire just did to me.
But I also knew I didn’t want to.
For the first time, I wasn’t in control…and I loved it.
©Ruby Ryder
His new GF is WAY into pegging. 
They have fun with "Pinkie".
pegmegently.tumblr.com
Podcast #181 mixup
