Learning to Serve

Learning to Serve

Subscribe to Penthouse Magazine Print Edition
Subscribe to Penthouse Magazine Digital Edition

A submissive man learns his proper place in the world is at his girlfriend’s feet, and her punishments become the reward he craves most.

Dating used to be relatively uncomplicated — I’d meet a girl, ask her out, take her to dinner and then hopefully get laid. Then I met Cindy.

I’d occasionally see her on my morning commute, and I’d always spend the rest of the day fantasizing about her. It was like riding the subway with a porn star. Cindy has gorgeous eyes and lips that look like they could suck the dick right off you, plus a set of extremely large breasts on an otherwise petite frame. Sometimes I’d get so worked up I’d have to sneak off to the office gym so I could masturbate in the shower. Finally, I decided to ask her out and see if she could live up to my vivid fantasies.

Our date started normally enough: We met at a wine bar downtown for a bottle of vino and some antipasti, and when that went well, we moved on to a nearby restaurant for dinner. By that point, I was hoping the night would never end, and I knew she felt the same when she invited me to her place for a nightcap. I said yes immediately, my cock stiffening as I contemplated my good fortune.

From the moment we sat on her couch, I knew she was going to exceed my dirty dreams. She didn’t even go through the motion of pouring us drinks. We both knew why we were there. As soon as my ass hit the cushion, she straddled my lap so that her huge tits were practically in my face, at least until she threaded her fingers through my hair, pulled my head back and pressed her mouth to mine.

Caught off-guard, I didn’t open my lips fast enough. I felt her tongue trying to force its way in, and I relented. In return, she started grinding her cunt against the bulge in my pants, which only made me harder. I liked where this was going, so I wrapped my arms around her waist and motioned to flip her over, wondering how fast I could get us both undressed.

To my surprise, Cindy stopped me and stood up. “Did I say you could do that?” she snapped, and I expected her to send me packing. Instead, she surprised me again by pulling me off the couch and leading me to her bedroom. I wasn’t sure what was happening, but since we were once again headed in the right direction, I didn’t ask any questions.

I stripped when she told me to, expecting her to do the same. She didn’t, but again, I didn’t question her because I understood this wasn’t going to be a normal hookup. She regarded me until I was a little embarrassed by my cock jutting straight out in front of me, harder than it had ever been. She stepped closer, and my erection twitched, a movement that was perceptible to us both. Running her fingers over my shaft, she smiled mischievously, and I almost came right there and then. I was already dripping a steady stream of pre-come, and as much as I was enjoying the waiting game, I hoped she’d relent soon and let me fuck her.

Moving her hand upward, Cindy trailed her fingers to my chest to flick one of my nipples. I quickly grew more desperate with the need to slide my dick into her cunt, so I pulled her toward me with the plan of maneuvering her onto the bed. And once again, she stopped me, this time punctuating her shutdown of my advances by pinching my nipple so sharply that I yelped. As the sensitive bud started throbbing, I realized how much I actually enjoyed the pain.

“Do it again,” I whispered, surprising myself with the plaintive tone of my voice. Up until then, I’d taken the lead in sexual situations, and yet now I found myself happily and willingly relinquishing control to this diminutive femme fatale. She was totally in charge, and I got the sense that if she weren’t, this wouldn’t be happening. On the other hand, I knew she wasn’t entirely disinterested in my pleasure when she granted my wish and clamped my nipple between her thumb and index finger. Then she applied the same pressure to the other one, pressing harder and harder until waves of a pain-pleasure mix coursed from my chest to the rest of my body.

I started writhing and couldn’t help but moan. Once again, I reached for her tits, thinking she might like me to return the favor, which was when she let go of my nipples, stepping away so quickly that I almost toppled over. “Turn around!” she demanded, and I obeyed without considering why. A second later, I felt the first blow to my buttocks. That was followed by another, and soon her hand was landing on my asscheeks hard and fast.

My cock and balls started aching; unbelievably, the spanking had made me unbearably turned me. I stayed still, waiting for her to make a move or send some sort of signal that we were going to take things to the next step. The anticipation was both frustrating and exhilarating, especially for a guy who was used to getting his way. I realized that I liked relinquishing the upper hand, almost as much as I liked feeling Cindy’s hand landing on my now-tender butt. She packed quite a wallop for a woman her size.

Still, my balls weren’t going to hold on to their contents forever, and even though she’d only briefly touched my prick, I felt myself nearing climax. I didn’t want to come on her floor; ideally, I wanted to come inside her, preferably in her cunt. I got so desperate that I did the only thing I could think of to convey my need without pissing her off: I asked.

“Can I fuck you?” My voice was hoarse with lust, and I wasn’t sure if she’d heard me over the slap she’d just delivered to my ass. She abruptly stopped what she was doing, moved back in front of me and asked me to repeat myself. “Can I fuck you?” I beseeched, my voice wavering as the stern look on her face told me I’d screwed up again. Still, I decided I’d rather anger her with words than with a puddle of semen on her carpet, and since that was looking more and more inevitable, I was left with no choice but to beg.

“Please, Cindy,” I implored, and to my surprise, she nodded her assent. Yet when I reached out to unbutton her blouse, excited to bare those huge tits, she smacked my hand away.

“From now on, you don’t do anything without my permission,” she instructed. “Do I make myself clear?” I nodded, happy she was relenting, and then watched as she began undressing herself. “Eyes down!” she snapped again before continuing, “To you, I’m not Cindy. I’m Mistress Cynthia.”

I cast my eyes downward and mumbled, “Yes, Mistress Cynthia.”

This new role felt strangely natural, and I was getting the hang of this game. I only hoped that I could satisfy her enough that she would let me play with her again. As I stared down at the floor, I heard the rustling of clothes being removed, and when the noise stopped, she told me to get on the bed.

I lay on my back, the sheets rough against my sore ass and my cock pointing skyward. I was looking up at the ceiling, but I knew she’d joined me when I felt the mattress shift. Throwing a leg over mine, she straddled my torso, and then she gripped the base of my cock and began lowering herself onto it.

She started squirming so I dove in deeper, getting a good taste of my own load, which was still dripping from her hole, as well as her sweet juices.

My crown pierced her slick hole, and I almost cried from pleasure. When she began easing herself downward, I did let out a sob-like noise while instinctively raising my ass to thrust into her. She was so wet that I could have slid right in to my root, but she placed her palm on my stomach and pressed down to keep my butt firmly on the mattress.

From then on, I remained still and let her do her thing, content to look up at the undersides of her breasts, two perfect half-moons swaying above me. Before long, my cock was completely enveloped by her pussy — but only for a second because she quickly ascended until only my crown was lodged inside her. She immediately crashed back down, effectively ending our period of taking things slowly. She rode me hard, her tits bouncing wildly, and I was already so worked up that I was filling her with my cream after only a few strokes.

My come was still spilling into Cynthia’s pussy when she pulled off of me. I immediately understood my transgression, coming without her permission, and what was worse, from the way she was panting I guessed she’d been close to her own climax. The last of my load was released into the air to pool on my quivering stomach, and she looked down, disdainfully, at my still-drooling member.

Without speaking, she crawled up my body until her knees were at my ears, her cunt positioned at my mouth. She didn’t have to tell me what to do, but I still waited for her command. “Eat me,” she said, and I eagerly began tonguing her slit. She started squirming so I dove in deeper, getting a good taste of my own load, which was still dripping from her hole, as well as her sweet juices.

I didn’t let that bother me; redeeming myself with Cynthia was more important. Putting my all into eating her, I used every trick in the book, from sucking on her inner petals to stiffening my tongue and thrusting it in and out of her. The one thing I avoided was contact with her clitoris, wanting to build her arousal as she’d built mine while showing off my expertise in cunnilingus.

She started writhing so I slowed down, wanting to drag out this moment. She reminded me that I wasn’t the one in charge. Mashing her pussy against my mouth, she demanded that I work harder, so I vigorously sucked on her button.

Her thighs clapped against my head as she sighed blissfully. I yearned to see her face, but I had to be satisfied with merely hearing her breathy moans. At least now I knew better than to stop until I’d been told, so I continued darting my tongue over her quivering folds to drive her to peak after orgasmic peak. I only stopped licking her pussy when she slid off my face and, panting and exhausted, flopped onto the bed next to me. When she caught her breath, she said, “Good boy,” and invited me to spend the night.

Fast-forward five years and we’re still together; we even cohabitate. We’re not married, but we don’t need to be, because Cynthia knows my dedication to her is steadfast, and the collar I wear around my neck when we’re at home is testament to that. I am totally subservient to her, and I wouldn’t have it any other way.

The other day we had plans to go shopping for a new couch when she got home from work. I forgot and was still in sweatpants, my thoughts consumed by a spreadsheet, when I heard her key in the lock. Damn, I thought to myself as I glanced at the clock, and though I hoped she wouldn’t be too angry, my cock stirred at the notion.

I stood as she entered the room, my head already hanging. Glancing up through my eyelashes, I saw my collar in her hand. I stepped forward so she could secure it around my neck. Then I stripped without being asked, wondering what she had planned.

I didn’t find out for a while because she left the room, leaving me there to ponder my fate. Our play had progressed to nipple clamps, ball gags and whips a few years back. I didn’t know which she’d return with, but I did know that the person who came back into my office would be Mistress Cynthia and not Cindy, my fun-loving girlfriend.

Keeping my eyes downcast, I soon heard her heels clicking down the hall, announcing her return. Next, I heard a sound with which I’d grown very familiar: that of the business end of a riding crop landing on her open palm. “Turn around,” she demanded, and I did, painfully aware that my naked ass was now totally vulnerable to her.

There was a “swish” and then a smack, and I first felt a sting, and then I felt the burn. She smacked me again, and my skin started throbbing as a dull pain radiated from the spot where the crop had landed. Her next few strokes fell on my other buttock, which was soon pulsating, too. I had to choke back grunts as I grew more and more aroused by this well-deserved whipping.

As Cynthia rained slap after slap on my asscheeks, I could hear panting from behind me. The blows started coming down harder, jolting my body forward as they fell on increasingly tender flesh, which forced me to clench my hands, grit my teeth and struggle to keep my balance. My dick ached, too, which wasn’t helped by the way my balls bounced each time I was rocked by the lash. Luckily, it wasn’t much longer before Cynthia tired of the riding crop and decided to find another way to teach me my lesson.

She ordered me to turn around and look at her, and I nearly came when I did. She’d changed from her conservative work clothes to a black merry widow and a pair of witchy thigh-high boots. The top of her silky garment could barely contain her sizable breasts, and I yearned to bury my face between them and breathe in her feminine scent. Due to my recent transgression, I knew it was unlikely that she’d allow me to do that; I’d be extremely lucky if she’d even permit me to lick her pussy.

The top of her silky garment could barely contain her sizable breasts, and I yearned to bury my face between them and breathe in her feminine scent.

I felt hopeful as she walked over to my desk chair, swiveled it to face me and sat down. I stepped forward, ready to kneel between her thighs and work my tongue over her cunt, but that wasn’t what she had planned. Swatting me away with her crop, she directed me to turn around again, and when I did, she grasped my wrists roughly and attached a pair of cuffs. Then she turned me back around to face her again and told me to watch as she pulled aside the crotch of her skimpy outfit to display a carefully groomed strip of pubic hair and her delicate nether lips.

Spreading her legs wide, Cynthia displayed her moist inner petals, which couldn’t conceal the engorged clit they normally cloaked. My mouth watering, I impatiently waited for her to beckon me toward her to sop up her juices with my tongue. To my dismay, she left me hanging. Instead, she gently stroked her outer labia, her crimson fingernails in stark contrast to the lighter skin underneath, All I could do was stand there and stare.

Her fingers moved inward, and soon her digits glistened with pussy juice. My own fingers twitched as I yearned to reach for her, but not only was I restrained, I also didn’t have her permission.

Turns out she didn’t need me anyway. With her free hand, she reached for a bag I hadn’t noticed earlier and pulled out a large, realistic-looking dildo. First, she held it out to me to suck, and then she placed it at her hole. My eyes grew wide as I watched the knob-like head stretch her open. Then her aperture clenched around the base right above a pair of ersatz balls, but only for a second because she pulled the toy right out and plunged it back in immediately.

She fucked herself with that plastic phallus like I wasn’t even there, although I knew she was putting on this sensual show for my benefit. She knew how crazy I got when I couldn’t touch or taste her beautiful body, and while I was duly frustrated, other senses were satisfied by the sounds of her gasps and moans and smell of her musky pussy. Of course, I could see her every movement, as well as the way her labia clung to the shaft that now shone with her juices as she jerked it in and out.

The best sight, however, was when she moved the fingers not holding the dildo to her clit and pressed down. She shrieked loudly as she came, and fucked herself even harder as she rode the waves of ecstasy. Although I was happy for her, I felt dismayed for myself because I could only bear witness to this incredible scene, and having to watch but not touch only brought me closer to my own peak. My balls pounded as I imagined sliding into her, and I let out a lamenting moan, which Mistress heard through her own animalistic noises.

She looked up and I thought there’d be another spanking, but she took pity on me instead. She motioned me toward her and I obeyed, and then she grasped my hard-on and leaned toward me, pulling me even closer, until my dick was pointed right at her mouth. Then she wrapped her lips around my crown just like she’d made me do with her dildo, before swishing her tongue over the sensitive skin. Chills ran up my spine, and I had to struggle not to come right away, even though that’s something I’ve gotten a lot better at since the night of our first date.

My efforts paid off, so I was able to enjoy her skilled tongue skimming over my shaft as she swallowed me whole. When her chin nudged my sac she retreated slowly, tracing the vein on the underside of my shaft during her ascent, and the air felt cool on my saliva-coated skin. But that didn’t last long because she deep-throated me again a second later, burying her nose in my pubes.

My buttocks clenched as now I struggled to keep my hips from rocking back and forth wildly. I would have fucked her face if she’d let me, but I held still and let her control my pleasure. She didn’t often indulge me with a blowjob, though she was an expert cocksucker. Her head rose and fell at the perfect pace, slowing down whenever she sensed I was about to send my load blasting down her throat, and her lips formed a tight enough seal to tease me without being uncomfortable.

Still, I was so far gone at that point that we both knew I wouldn’t hold out for long. With her lips wrapped around my crown, Cynthia glanced up and gave a little nod, which jerked my prick in the process, and I immediately rewarded her with a mouthful of semen. Quickly, she slid back down my length to bury me in her throat and not lose a drop of my cream.

I groaned loudly through my orgasm, feeding her volley after volley until the contents of my balls were depleted. As soon as I finished, she released me from her mouth and the cuffs and told me to get cleaned up. “We can still make it to the store if we hurry,” she said as she extracted the dildo that was still in her cunt and left me to get dressed. Then we drove to the mall like any other couple, except for the red silhouette of Cynthia’s riding crop still emblazoned on my ass.