Classic Variations: Ms. Benson’s Chauffeur

Happiness. Relationship. And fulfillment. They’re all words that people use to describe their goals in life.

I have finally reached a point where I have them all. The way I’ve done it may seem to be awfully strange to you, but that’s not too terribly important to me. What is important is that I was willing and able to find a unique and intense satisfaction in a way I had never dreamed possible.

It began when I was separated from the army. I suddenly discovered that my smart-aleck ways had left me high and dry. I was certainly done with military life, but while I had been in the service I hadn’t learned a damned thing. The other guys who were getting out had been taught to work in electronics or ordnance or some other field that had an application in civilian life. I had dedicated my own army career to the avoidance of as much work as possible.

As a result, I had no skills to take into the job market at all. I moved back to my hometown and went to live with my mother. While it was okay in some ways, there were others I didn’t take a liking to. For one thing, I didn’t feel it was the right thing for a man of my age—I was twenty-five—to be taking advantage of his parents.

I had already made the rounds of employment agencies. I told them that I was looking for something that would lead to a decent career; I also wanted a job that would offer an opportunity for training. After a couple of months of inactivity while I watched my army savings being eaten away, I went back and told them I’d take anything, at least for the time being.

One of them told me there was a job offer for a houseman/chauffeur at the Benson house, which stood on the ridge overlooking town. While I didn’t like the idea of being a servant, I did need a job—any job— badly. Besides, I had some experience in the service, where I had to put in time as an orderly. The pay, which included room and board, looked good too.

So I went up to the address they gave me for an interview the next day. It was quite a mansion, all brick and dark wood on the outside, with an enormous lawn on the slope of the hill that led up to it. It was probably the biggest house I’d ever seen outside the movies.

I knocked on the door and was pleasantly surprised when a very attractive girl opened the door, wearing a maid’s uniform. We smiled at each other. After I told her my business she spoke in a French accent and led me into the waiting front room. “Madame would prefer you not to sit on the furniture,” she cautioned as she left me standing there. I shrugged. What the hell?

“Madame” entered the room shortly. If the maid was good-looking, this woman was striking. Her rich red hair was severely pulled back into a bun on the crown of her head. Her skin was creamy smooth and I didn’t think she wore any makeup except for dark lipstick. Her eyes were beautiful, and I thought the thick lashes were natural.

She wore a suit that was so masculine in its cut that it would have looked like a man’s if the bottom of it weren’t a skirt, and a tight one at that. She sat back with her back as stiffly at attention as any drill sergeant’s and announced that the most appealing part of my application was my recent military experience. She hoped it would allow me to mesh with her household’s very efficient principles.

She went on talking about the responsibilities of the job as though she assumed I was going to take it. I would have to drive her around to her business appointments during the day and do the errands and shopping for the cook. I would be expected to keep two cars in immaculate condition, a limo and the station wagon she had for the housework. Also, I would have to keep the lawns in shape.

I said, “Sure.” She quickly and sharply corrected me: “It will be ’Ms. Benson’ at all times. Do you understand?” I did. She rang for the maid, who showed me my room. The schedule of the day was given to me. I was expected to report in time to drive Madame to the shops and the banks in the morning. We would also get me a uniform at that time.

I spent that night thinking about the two women I had met. I had always thought a guy like me should be attracted to a cute looker like the French maid, with her pert little breasts and nice round fanny. But I always had trouble with those frilly girls. I always felt awkward around them. I held my cock and rubbed my hard-on with a hand slippery with my spit to get my come boiling in my balls, but I couldn’t keep the French maid’s image in my head. Instead, a picture of Ms. Benson crept in.

She stood there in an outfit like the one she had worn that day. But there was a big oval cutout of the suit jacket and blouse. The round opening left her large breasts bare, her deep red-brown nipples were easy to see against the milk-white of her skin. She wasn’t really smiling when I shot my load onto my belly. It was more like a smirk.

The image shook me. I couldn’t understand what it was that I had been so turned on to. It was a new experience for me and I wasn’t comfortable with it at all. I decided then and there that Ms. Benson was dangerous. I’d have to look out for her.

The next morning found me waiting in front of the house with the limo—it was a great old Cadillac—for Madame’s morning trip. I drove her into the downtown area and waited patiently for her to do her banking and pick up a few things in some of the shops. I didn’t like it very much when she took me into Sampson’s for my uniform. I knew all of the guys who worked there; many of them had gone to high school with me.

Still, I stood quietly while she told Joe Sampson what kind of uniform she wanted. She sat there, smoking a cigarette, while he took my measurements. He brought out a set of clothes and I had to put them on and let him pin and mark them up to be tailored for me. She insisted on a cap as well. I felt like I was back in the service by the time she was finished.

Then she wanted a pair of high-gloss boots for me. She picked out a pair that came up over my calves. They were designed to be worn outside your pants. I also knew they would be a horror to keep polished.

That was that. Joe said to come back in a couple of days and pick up the altered things. She paid for them and I drove her home. I watched her in the rearview mirror. She couldn’t have been more than thirty years old. She possessed every gesture of a person in command, though. Something in the papers she was reading was ticking her off. I knew that. She was scowling. I could feel my cock rising in my pants as I saw a glimpse of her leg that was being showed off as her skirt rode up.

That little bit of leg was what did me in. We were going up the long driveway while I was staring at it in the rearview mirror. I wasn’t paying enough attention. Before I knew it I had sideswiped a little tree with the car. “You idiot!” she screamed at me. I stopped the car and we both jumped out. While it was only a scratch on the side of the two doors on that one side, I knew it would cost an arm and a leg to get a car that size fixed. She stood there and kept yelling. She worked herself into a rage and then roundly slapped me across the face. She left me standing there rubbing my hot cheek while she strode up the hill and in the door.

“Madame wants to see you right away!” I figured I was in for the big heave-ho. I went down the stairs and into the same big room where I had first met her. She was waiting this time. She told me to follow her as she led me into the garage. We stood there and looked at the damage.

I was surprised when she didn’t fire me on the spot. I was even more surprised when she apologized. She said she shouldn’t have lost her temper like that; she called it acting like a silly girl. Then her eyes got very hard and she looked right at me. She told me I was a man and that I deserved a man’s punishment. If I wanted to take it, I could stay on the job. I couldn’t quite figure what she wanted, but I had somehow gotten an idea.

“Okay, give me a man’s punishment.” I said. I was going to show her that just because I was hired help, it didn’t mean I was less than anyone else.

“Give me your belt.” I took it off and handed it to her. “Turn around.” I did. “Pull down your pants.” I hesitated. I was ready to walk out by that point, but then decided I was going to prove something to her—or to myself. I unzipped the trousers and let them fall to the ground.

“Bend over.” I felt the breeze cool my ass and my heart beat in my ears as she pushed the back of my neck down onto the hood on the limo.

Whack! That little bitch had laid the leather right into me. Whack! Again. I was damned if I was going to give her the pleasure of hearing me yell. But I also couldn’t get that image out of my head. It was the same one that had come over me when I was dreaming and beating off. I felt the pain in my ass, but I saw that cool, confident woman in my imagination with her open-tit dress and those sharp nipples sticking right out as though they were taking aim at me. I clenched my teeth. Whack! She belted me at least six good ones.

I was panting. But I had to take it, by God. I had shown the bitch that I could take it! She told me to stand up. I hesitated. I had shown her one thing, but I didn’t want to show her something else on top of it. But I stood. There on the car was a pool of my come that had shot out while I was leaning on the hood, thinking about that hard woman behind me with that belt landing on my ass.

She never said a word about it, directly at least. She ran a finger through the ooze on the metal, then smiled and wiped it on my shirt. “Polish the car,” she said, and then walked away.

Shaking with fury, I pulled up my pants. I had let her belt me to prove I was a man and then I had shot my load while she was doing it. Some man! I smashed a fist against the concrete wall of the garage. I thought I should leave. But I told myself I needed the money and that she wouldn’t do anything like that to me again. I wouldn’t let her get away with it.

The hated image of her in that bare-breasted outfit kept recurring. I couldn’t erase it from my mind at night. Or hide my feelings when I felt the warmth on my ass where the belt had landed. I got the car fixed and went about my job conscientiously the next few days, doing everything so well there was no cause for any comment from her. Our conversations were limited to: “Mornin’, Ms. Benson” and “Good day, young man.”

Things changed again about a week later. When she came out that morning she had a sly grin on her face. After the usual errands she told me to swing by the store. The uniform should be ready. She wouldn’t let me take it home but made me put it on right there in the men’s changing room—boots, cap and all. Then we got in the car.

“One last stop, Jamie.” She directed me to the little store near the riding school on the outskirts of town. Usually I stay in the car and wait for her when she goes shopping. I wasn’t sure why she wanted me with her this time, but I followed her orders and fell in behind her. She went directly over to a rack of mean-looking little whips. The clerk called them riding crops. She flexed each of them, and then picked out a stiff one coated with black leather. There was a little loop of dyed cowhide at the end.

Hoping the clerk didn’t see the blush I had creeping over my face I looked at the crop, knowing full well what she meant to do with that thing, but I was damned if she was going to get away with it. I drove her home. I couldn’t figure out my response, though. My head was stubbornly rehearsing the words to use to quit, but my cock and balls were sweating in the shorts where my hard-on was cramping them.

Pulling the limousine up in front of the house, I jumped out to open the mistress’s door. She told me to bring the packages inside for her. I grabbed them and followed her. I saw no way out of accepting her lead as she walked up the steps. We went into her room, an enormous space. The large bed was in one corner and there was a sitting arrangement with a settee and chairs in front of a bay window, and a dressing table with a large mirror.

She told me to put the things on her bed. I did, and waited for a moment to see if she’d say anything else to me. She just stood there, neither giving me leave to go nor telling me to do anything else. Instead she stared at me while she slipped out of her jacket, saying, “Take this.” I laid it on the bed. As she unhooked her pearls she explained that the maid was off that day. Then she started unpinning the bun at the nape of her neck; she wanted me to help her brush her hair.

Burning with humiliation, I told her in no certain terms that I was a man and not about to do a woman’s work. She only smiled. She purred something about having seen evidence of my manhood. The comment only increased my discomfort. The last of her pins came out and the full stream of hair fell over her shoulders. She picked up the brush and very coolly asked me again, this time sitting down in front of her mirror. There was still an edge to the way she talked, but not as chilly as before.

Finally I gave in and took the brush. I have to admit that I wanted to touch that long beautiful hair. I worked the bristles through the strands, pressing down after each stroke. The silky feel was sensuous beyond belief. I felt my cock rising again, but this time there was no confusion as to why. I loved the feel of her. I knew she was watching me through the reflection of the mirror. I only hoped she couldn’t see the tent in my pants so I kept the bulge right at the back of her neck, out of view. When I had done enough brushing she told me to stop. I went back to my room.

I couldn’t wait long enough to take off my clothes but just ripped down the zipper of my uniform pants and grabbed my cock. The odor of her hair was still on one hand. I held it to my nose while I used the other to rub my desperate meat. I shot a jet of come just from the smell of her in an orgasm so powerful that I nearly felt off the bed.

Everything changed after that. The very idea of her became intensely erotic for me. I stopped trying to fight her. The next week it was almost impossible for me to keep my cock from raging with stiff erection whenever she was in the car or I was in the same room with her. I didn’t even mind so much that she seemed to know what was going on.

Subtle little things happened inside me. I found myself being more careful about polishing my boots than I had been in the army; they glistened each morning. I was careful about the appearance of my uniform and the interior of the car. I discovered that I wanted to please her. I knew why, too: I was just waiting for the opportunity of the maid’s next day off.

When it came she took me to her room the same way as before. Again she had me stand there in my uniform while I watched her unpin her hair. I took the brush when she offered it to me. I was slower this time. Something had snapped inside me. It wasn’t a humiliation to be doing her hair—it was a privilege.

Because I was so involved with her hair it took me awhile to notice something else that was different. Usually her blouses were very formal and buttoned to her neck. Today she wore a silky one, without a bra. It was open enough in the front for me to see the cleavage between the two mounds that were as creamy-white in real life as they had been in my dreams. I felt my knees go weak. Somehow I stood upright while I watched those taut breasts rise and fall with her breathing. I could see the line where her tan met the pale area that had been covered by the bra of her bathing suit. The dark skin looked warmly inviting; the ivory skin looked succulently tender.

She was doing it on purpose, I realized, as she began to talk and unbutton her blouse. On the one hand, the way her casual conversation about the house was phrased to put me in my place as a servant. On the other, there was no mistaking that she was seducing me.

Finally I couldn’t help myself anymore. I watched my free hand slowly move inside her almost—open blouse and shivered with delight as I felt my palm come into gentle contact with her first nipple and then her whole breast.

Her voice came calm and firm. “You should have asked permission.”

I froze then. But to my amazement she undid the rest of her blouse and took it off while my offending hand stayed in place. She stood up and faced me. The two large breasts were as beautiful in real life as they had been in my dreams. The nipples’ brown circles were even larger. She put her hands on her hips and curtly asked if I like what I saw.

“Yes, Mistress.”

“Mistress?” I had never called her that before. Out loud. She smiled again. “I like that.” I was blushing furiously, pained by a trapped lump in my pants and mesmerized by the sight before me. She suddenly asked if I’d like to suck on her tits. The words didn’t sound crude on her lips. My voice didn’t simply say yes, it pleaded for permission to take them in my mouth.

Then she quickly undid her shirt and took off her panties. She stood there totally naked and told me I’d have to earn her tits. I told her honestly that I’d do anything for the honor. I meant it too. She spread her legs and told me to kneel. As though the sight of her naked body had hypnotized me, I feel in front of her with my face positioned before her cunt.

I wanted to bury myself in the strong odor of her pubic bush, whose rich redness was ever so slightly lighter than the hair on her head. But somehow she had gotten hold of that riding crop. She slapped her palm with the black leather and warned me not to do anything before I was told.

She gave me careful instructions on how to eat her. She wanted my hands behind my back and only my face touching her. She directed me to lap up and down between the halves of her hairy flesh first. I kept skimming across the nub of her clit as I followed her every order with care. I felt the rush of warm, sweet—smelling liquid coming down for inside her before she told me to finally stick my tongue inside her. I fucked her with my lapping motions, rubbing my nose against her belly and sucking as much of her juice down my throat as I could.

When her legs began to quiver I knew she was getting close to orgasm. But she drew back, taking her precious flesh away from my hungry mouth. “Strip,” she snapped calmly. She watched as I took off my uniform and boots and finally stood in front of her with a hand trying to cover my urgent erection. I thought she was going to slap the riding crop on my hand to force it away, but she only used it to push it from its protective position. She smiled at the result of her discipline.

She commanded me to resume my kneeling stance. Then she ordered my hands back behind me and my knees spread apart. I trembled when the tip of the crop casually touched my nipples . . . then my erection. I was terrified she was going to use it on my tender penis. She only played with it though, constantly building up my fear.

I longed to go back to her cunt. Instead she leaned over and rubbed her breasts against my face. The large ovals were so smooth and satiny soft as they brushed my skin. She told me I had done well and deserved a reward. I was to lie on my back and stretched out my arms and legs. When I was sprawled on the floor, she crouched over me and used a hand to guide my cock to the opening of her cunt.

Unable to restrain myself, I let my hips move up, forcing myself inside her to the hilt of my shaft. She collapsed onto my midsection and let my cock be engulfed in the moist warmth of her cunt. “Be still,” she said. I lay there passively while she rose and fell on my erection, fucking herself with its hard length.

Her large breasts swung in the air as she increased the speed of her movements. We were both so hot that it took only a short while for the two of us to explode into orgasms so violent they shuddered through our bodies as her pussy’s spasms clasped my cock.

As soon as she regained herself she stood up. I was blind with passion for her but somehow knew I shouldn’t get up myself. I moved around on the floor until my head was at her feet. Tenderly, I supposed religiously, I bathed her toes with my tongue. I adored her feet and the sensations of my body on the floor in front of my mistress.

When she gave a signal I got up and followed her into the bathroom. We showered together, but it wasn’t like anything I had ever seen or heard of in any sex magazine. I followed her orders and massaged her and lathered her body. When we were done I toweled her dry from head to toe.

The whole process revived my hard-on. There was no hiding my aroused state from her. She smiled at the sight. I thought I was supposed to leave, but when I gathered my clothes she stopped me. She gave me a talk about my understanding that while sex was going to happen again when she decided it was time, our relationship was strictly mistress and employee— if anything, even more so.

I told her I understood that, but she kept going. She explained that because of what had just happened any infraction of the rules would have to be dealt with severely. She said it was only fair that I understand the consequences of her displeasure. She picked up the riding crop. Still smiling, she laid my towel over the hassock by the window and told me to lay myself over it. “Ten strokes, Jamie. Be a man.” My ass was wet from the recent shower, but as she laid into it with ten hard strokes of that vicious crop, each one left a line of burning skin behind it.

Goddamn it, I took those ten lashes! I couldn’t hide the tears of pain and humiliation they brought to my eyes. And I couldn’t hide the second puddle of come that was captured in that towel from my second orgasm. But I took the beating! She rewarded me with a kiss on my forehead as I did finally leave.

A month later the French maid was let go. I got a raise, which was only fitting, since my duties increased so much. I stopped wondering about the whys and wherefores that have made me fall in love with Ms. Benson—and I think she is in love with me too. I do know that the memory of that crop makes sure I do what she wants, how she wants, when she wants. She hasn’t had to use that one again.

It’s been a year now. Mistress says it will all last for many more. The other day I went back to the store by myself to get another uniform. The clerk there said he couldn’t understand a healthy American male being happy as anyone’s servant in this day and age. I only smiled and told him it suited my temperament just fine.