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Sugar Mommy

By Kfod

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Views: 10,051 | Likes: +61

*This story does not take place in the US, so some everyday dynamics may not be too familiar to some of you guys – which does not prevent you from enjoying the story. Happy reading!

 

It was my first semester at the University. I had joined Law school without knowing exactly what to do with my life. Those first few months were a big mess, there was almost a party every day, and I ended up not dedicating myself as much to the subjects as I should have. At the end of the semester, then, I ended up owing grades and had to take some recovery tests so as not to repeat them. One of them was Criminology, with Dr. Paula. She was a successful lawyer in her forties, about  5′57″ tall, with straight black short hair cut at chin length. She had clear eyes and exuded a sophisticated perfume. Her presence was intimidating because she had a firm voice, always looked into people’s eyes, and walked very well-aligned. I don’t need to say how many new students were mesmerized by this woman, right? And, of course, there were rumors that she had already hooked up with some student in the past, but anyway, just rumors.

On the day I took Dr. Paula’s test, I dedicated myself quite a bit to studying and took a very extensive test. The class time was ending, and I was the last person in the room. Me and her. That’s when she asked if I had finished yet, and that I should hand in the papers because time was up. In fact, I had managed to finish and went to her desk to hand in the test. She was looking down, correcting something when I raised my arm holding the test. She then raised her face, looked me in the eyes, and took the papers. She read it over and just said “Henrique, right… okay! Keep an eye on the website, I’ll include the grades there…”. I thanked her and, right when I was turning around to leave the room, she interrupted me by offering me a ride home. It was kind of surprising since I didn’t know where she lived and imagined that she didn’t know where I lived either.

— Oh, you don’t need to do that, professor… Many buses are passing by at this time.

— Are you sure?

I didn’t answer immediately and paused for a second.

— Where do you live, Henrique?

— It’s not too far away, sometimes just walk home.

— Ah, silly, I’ll take you then!

I accepted without much reluctance. We went to her car, a large, apparently armored, black SUV. We didn’t exchange many words on the way, just some trivial matters to fill the void. I noticed that she didn’t ask the way to my place, she just followed a route that I didn’t know. I only realized when she started massaging my cock through my pants. I felt a chill down my spine – I was horny but also afraid. Her intoxicating perfume, inside that closed car, was like poison. My dick got hard and she started masturbating me while driving. She stopped a moment later when we arrived at a very large house surrounded by a high wall. We went down to the garage and she took me to a room upstairs. She threw me on the bed and told me to take off all my clothes while she also undressed herself, standing up. I’m not going to lie, I didn’t last long on that attempt. In just under two minutes I must have cum. I was embarrassed and she seemed to find it funny, but I also felt a hint of disappointment – she said it would be better if I left. At the height of my stupidity, I thanked her for the ride and left the room, putting my backpack on my back. On the bus back home, I received a message from an unknown number. “Next time, I’ll want to be a priority. And needless to say, nothing happened, right?” I couldn’t believe it, how did she even get my phone number? Will there be a next time?! I couldn’t say what she saw in me, I wasn’t ugly but I was an ordinary guy, without any exceptional beauty – tall, yes, but a little thin for my age, couldn’t grow a decent beard yet, and had a wavy brown hair that reached my shoulders. A few days passed, it was vacation and I stayed home all day watching movies, reading, or playing video games, I only went out every now and then to a movie, drink a beer with my friends, or relax in the park.

After about three weeks, I received a message from the same number, telling me to go to her law office the next day, the address and emphatically saying “Come well dressed”. I didn’t even think about not going, whatever the reason might be – in those previous days, I hadn’t stopped thinking about that afternoon at her house even once.

The next day, I put on a button-up shirt, jeans, and casual sneakers and went to her office. I arrived at the building and was greeted by a secretary. I told her that I had an appointment with Dr. Paula and then she asked me to wait in a meeting room. The office occupied an entire floor of the building, very sophisticated and well-decorated. After about forty minutes, the door opened and Dr. Paula entered with two more men, probably partners of the firm. She looked beautiful as always and had her hair a little shorter, revealing a bit of her shaved nape under her straight dark hair. She introduced me to them and said that I was there for the internship position. This caught me by surprise: I didn’t know that was the reason for being there. I wasn’t exactly looking for anything to do at that moment, but I also didn’t show any surprise in front of them. After an awkward conversation of a few minutes, they left and only the two of us remained in the office. However, this room was surrounded by glass, partially visible from the outside. Sitting next to me at the table, she ran her hand over my pants, massaging my cock. “I was worried that someone passing by might see, although the table covered her gesture. She whispered not so close to my face:

— …I told you to come well dressed…

I smiled embarrassedly and, when I made a gesture to caress her, she left an envelope on the table and got up.

— Bring it signed by tomorrow… — and then, left the room.

I left still full of lust and didn’t even see what was in the envelope. Only on the bus back home, I opened it and saw the papers. It was indeed an internship contract. I was shocked by the amount of the scholarship – it was what I imagined earning only after graduation. In addition, I had to consider that her office is one of the most prestigious in the city. Basically, every law student’s dream is to intern there, simply because of how much weight it carries on a resume.

The next day, I woke up early, got dressed, and ran to the office. I signed the papers, presented the documents, all that bureaucracy and it was almost lunchtime when I saw Dr. Paula coming out of the elevator. She looked at me and gave a slight nod of her head, almost imperceptible, and went into her office. Sometime later, I was leaving the office for lunch when I saw that she had sent me a message: “Meet me in the parking lot”. I went there, located her car, and waited nearby. About ten minutes later she appeared alone. We didn’t kiss or caress each other. We got into the car quickly and drove off, but I was surprised to see that we ended up at a mall.

— To work there you need to dress like a man, Henrique. I told you to come well dressed. Don’t embarrass me. I’ll take you to a salon while I pick up some clothes for you.

Her authority intimidated me as she spoke. She was going to take me to a salon whether I wanted to or not. I hadn’t cut my hair short in some time; it hadn’t even crossed my mind that I would have to cut it to work in an office although I had heard some complaints from my parents about it.

She took me to the salon, waved at a guy, and introduced me as her nephew, always speaking very politely. Then she showed him some images, references of haircuts, and showed me quickly, as if I had already consented. She told me he would take care of me and left. The haircut in the image I saw at a glance was something very short, with the sides shaved in a fade, showing the skin and the top very short, maybe one and a half, at most two inches long. There was no time to think, much less say anything. Soon after covering me with a cape, he began to shave my nape with the clippers. I felt the cold of it touching my skin which, now exposed, felt the freshness of the air for the first time in years. I also felt cold in my stomach. I left home with long hair and was going to return with very short hair, almost shaved; what was I going to say? What excuse was I going to give? I also felt a certain excitement in realizing that Paula had control over everything, even how I would cut my hair. The clippers were now shaving the side of my head, revealing a pale skin that I had never seen before – the excitement increased. It wasn’t no-guard-at-all, there was some residue of hair there, most likely it was like n.1 guard. The hairdresser finished shaving the sides and started cutting the top. He passed the scissors without mercy in three movements; I heard the sound of the blades opening and closing while long strands fell over my lap.

– Quite a radical change, huh! – said the hairdresser excitedly with the transformation.

– … yeah! Quite! – I muttered embarrassedly and somewhat incredulous.

– But you’re going to look handsome!

He was finishing the cut, and the bangs that used to cover part of my face now didn’t even reach halfway up my forehead. That’s when I saw Paula out of the corner of my eye arriving with some bags from men’s stores. I saw the expression of surprise contained in her eyes when she saw me like that. In fact, I even didn’t recognize myself immediately either, but I liked the image that reflected back from the mirror. It no longer showed any boyish expression I looked more mature, even more masculine. I ran my hands over the back of my neck and felt strands so short that they gently prickled when I touched it. We left and immediately went to her house, Paula paid for everything. She seemed more excited, running her hands eagerly over my shaved neck and moaning as I penetrated her. I also found it nice to feel her hands spreading over my almost naked head, it was a new sensation and an almost erogenous region that I had discovered. We fucked all afternoon, this time I didn’t rush things – I made her cum. Before I left, she told me to keep the haircut, which she thought looked much better than that boyish hairstyle.

After that, my life changed. She took me to sophisticated restaurants, gave me a state-of-the-art cell phone, expensive clothes, perfumes and shoes, and one weekend we even traveled together to one of those luxury resorts on the coast. I had to always keep my hair very short, take French classes, and go to the gym almost daily – she paid for everything. My role was to fuck her, when she wanted and where she wanted. Most of the time it was at her house when she called me, but we ended up making out in airplane bathrooms, in the college garage, beside the “quickies” we had at the office sometimes. It was all hidden, although I had to deny some suspicions to a friend from time to time. Perhaps more by luck than precaution, we were never caught together. And boy, I got used to this life. I satisfied Paula and then I went back to my routine.

One day, already at the end of the first six months that I was working in her office, we went to her house. She was a little more serious than usual, didn’t talk much on the way, and didn’t touch me, as sometimes happened. Already in her garage, I saw a car that wasn’t there before. A brand new sedan, it even smelled like new. Going up the stairs to the bedroom, she asked if I had seen the car and asked what I thought about it. I couldn’t believe it, was it really for me? I had a driver’s license but didn’t drive because I didn’t have my own car. I told her it was a great, very beautiful car. She noticed in my voice or in the change of my behavior my suspicion and turned to me before opening the door of a room that was always locked.

— It’s yours.

— What?

—The car, of course.

— What do you mean? Paula, I… wow! I don’t know, I don’t know if I can accept… — I was speechless, of course I wanted it! But I thought about the consequences, would someone suspect something? Clothes and cell phones were fine, but how would I hide a car?

— Say it’s from the firm.

— My God, I… it’s beautiful, I…

— But there’s a condition… — she said, no longer as serious as before, looking me in the eyes knowing she had me in check.

At that moment, I admit, for the first time I became apprehensive about our dynamic. It was an interesting relationship, I liked it, but there were always counterpoints. And the counterpart for such a gift had to be big. I paused for a second while she unlocked the door and went in. Still outside the room, trying to imagine the possible consequences of accepting this gift, I also thought about how life was great: a good job, hot woman and everything else. Didn’t want to give up on that so I breathed and went in. While locking the door behind me, she looked at me and said almost smiling: “Good boy”. She asked, in a sweeter tone, for me to take off my clothes and sit on the chair. I looked in the mirror and realized how I had changed in these months. My body was beautiful and strong, and my face, shaped by very short hair and stubble, was fierce, and masculine. She, also without clothes, went behind me, opened the trunk and took out a hair clipper. As I suspected, she seemed to feel horny about it before. She looked in the mirror and turned on the clippers. The buzz filled the room immediately and made me shudder. As suspected, I was about to go bald. To be honest, the price was not as expensive as I had imagined. I could stand the excuse that I shaved it out of curiosity or that I made a bet or something like that. She moved away from me and didn’t want to prolong the waiting – from behind, she positioned the clippers on my forehead and looked at me through the mirror smiling, observing my reaction. I also smiled, partly out of concern, partly out of motivation. She then ran the clippers to the top of my head, leaving a path of pale skin between the forehead and the top, and in fact, it was zero, no guard, as the size of the hair left was even smaller than the one on the side of the hair. Once again, now from the side to the top – the sound of the machine became more aggressive when it was l actually shaving the hair; Paula was smiling, she seemed to enjoy the game and me watching it, becoming bald with each pass. At the end of this process, I saw myself bald for the first time in my life. I ran my hand over my head and it felt like touching my unshaven face, as well as feeling the sensitivity of my head. Paula also ran her hands over my head, removing the hair that fell into my face. And she looked at me with admiration. I pulled Paula by the waist to kiss her, but she broke away.

— Wait, I’m not done with you…

— What? 

She opened the trunk again and took out some razor blades and foam. I thought she was going to shave my beard, but what she really wanted was to make my head smooth. Since we were there, and I was already bald, I wouldn’t reject it. After all, in two or three days the appearance would return to the way it was. She began to spread shaving foam with her hands all over my head. And using a razor, she began to shave off any remaining hair that went beyond the skin of my scalp. The feeling was actually good. It took about fifteen minutes and Paula was done. She removed the foam with a towel and I actually saw myself, completely bald. A white head, limited by a rounded silhouette. When I ran my hands through it, I noticed how smooth the head was. The fingers slid without any friction. I felt the cold of my hands and the tips of my fingers touch my scalp. Then I felt Paula’s fingers until she approached me. 

— You’re a baldie now! — she said, laughing in a playful tone.

I smiled as she sat on my lap facing me. She kissed me while feeling my shaved head with her hands. Then she licked my bald scalp. I felt the touch of her warm tongue slide over my head. It was exciting for me, too. We had sex on the chair and then went to her room. We continued our night, experiencing this new sensation more and more. The next day, as I was getting ready to leave, Paula excitedly told me: 

— I’ll wait for you in my salon again next week… 

I thought this would be an eventual thing. But apparently, it would be permanent. Apparently, I would be bald for a while. And that’s okay, I liked it. 

— Yes, ma’am.

 

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