This happened seven years ago, when I was 24, and it was one of my favorite buzzing events.

Billy was a 20-year student studying at a local college. He came into our shop one day in January badly in need of a trim. He had long, dark brown hair that looked limp due to its weight. It was fine, but thick, and it didn’t become him. Billy had the makings of a handsome guy, but his hair covered up his pretty ears and didn’t bring out his stunning hazel eyes.

He ended up in my chair by the luck of the draw, or so I thought, and asked for a consultation. It appeared that he was having trouble reading with his eyes always focusing on his hair instead of his books. I warned him that I had a highly-opinionated view and didn’t like long hair on guys.

He asked me some other questions, and my radar detected he was looking for more than a haircut. He wanted to know how I cut my husband or boyfriend’s hair, and I told him I wasn’t married and was dating a few guys with nothing serious. He asked how I would cut his hair if he were my boyfriend, and I knew where he was going with this.

So, I came out and asked him if he wanted to be screwed after he got his hair cut. You should have seen those gorgeous eyes dilate. He laughed nervously and then asked me if I was serious. I told him for the right haircut, I would wear him out.

Billy said I could do anything I wanted, and so I pulled my Osters out of the drawer and attached a 00000 attachment on them. I was about to start buzzing him when I had a thought: why not let this haircut take place at the same time as the other event we had planned.

I grabbed Billy by his right shoulder and whispered gently into his right ear, “I’m going to cut your hair at my place tonight, and I want you to be in me when I’m doing it.”

Billy asked me what he could bring over for dinner and what wine I drank. He was trying to put on his perfect gentleman act knowing he would be a deviant little boy in a couple of hours. I thought it was cute from this 20 year old to want to treat me to dinner and drinks even though he already knew he was going to get lucky with a cougar. He almost forgot to ask me where I lived. So, I walked him outside, pointed at the low-rise up the street and told him what unit I lived in. I told him to be there at 7:30 PM and not a moment earlier or later.

At 7:29, the doorbell buzzed. I was about to give Billy the shock and ride of his life. I came out in my special Victoria’s Secret black bra and panties and nothing else. If it had been someone else by accident, I would have really been embarrassed. It was Billy, and his jaw dropped to the floor when he saw my athletically-fit and well-built body. It usually gets me what I want, and I wanted some young cock.

Before he could say anything, I was attaching my body to his and giving him a warm French kiss. He took a few seconds to get used to my aggressiveness, okay my nymphomania, and he began to make his tongue do nice things.

I asked him where his protection was, and he told me he didn’t even think about it. I thought to myself, “Yeah, right,” but then Billy told me something else. “Annie, I… I haven’t ever done something like this,” he said. I told him it was fun to do a little kinky stuff now and then to keep sex interesting. He stuttered back, “I mean I haven’t ever done anything more than felt a girl’s breasts once by accident. I have never had sex, and that kiss was my first with tongue ever.”

I had deflowered virgin boys before, just not any that were 20 years old. I tried to imagine why a good-looking boy like Billy had never had sex, and I couldn’t think of the best possibility. I asked him if he was sure about this, and he replied that he was super shy around girls and had not even been on a real date before.

This was a Wednesday night, and I began to have some doubts about having sex with him if he later might regret having his first experience at the expense of my fantasies. The more I talked with Billy, the more I realized he was a really sweet boy and needed to have a better first experience than to have his head shaved while I was on top of him.

I talked with Billy, and we ate dinner and a couple glasses of wine. I told him he needed a better first experience, and then he told me he had chosen me three weeks ago as the girl he wanted to lose it to. He had seen me giving a guy a burr haircut through the shop window and immediately was attracted to my amazon appearance. He had watched me give some more cuts and saw that most of my clients wore very short hair. He began to fantasize about me shaving his head to fuzz and had begun to masturbate while he imagined me buzzing him.

I had never had an experience like this with a boy before. I thought only girls were that straight-forward about things like this, and here was Billy telling me that he fantasized about me and wanted me to do to him what I had been fantasizing doing to him.

We made an agreement. There would be no haircut or sex that night. He would wait 48 hours to Friday and come back with a suitcase prepared to stay the entire weekend.

I borrowed my work mate’s video camera and brought it home Friday. It was the perfect weekend to stay indoors. It had started to snow around 3 PM, and the city lights and snow made it a romantic setting.

Billy came over at 6:15, just as planned. This time, I made dinner for him. I fixed my grandmother’s sausage lefse recipe. I told Billy not to bring alcohol because I wanted him wide awake. I served strong coffee with chocolate syrup for a dessert drink to make sure Billy would be alert.

I took him into my bathroom and showed him that everything had been set up and ready to go. He asked about the camera, and I told him that was for the haircut, and it would not become a XXX movie.

Billy took off his shirt, and I put one of my old capes on him. I told him he was going to become G.I. Joe, and he had one minute to reconsider before I rid him of all his hair. He told me he was ready, and he wanted me to tie him up. I went into my bedroom and retrieved the ties to three of my house coats. I tied them around his arms, legs, and chest and then popped the camera on.

This time, I was wearing my tiger-striped haircutting blouse and nothing else. On came the Osters. I had the 00000 out and nothing else. Billy was about to be buzzed. I gave him a nice kiss and massaged his neck and then put the clipper to his nape. I wanted the first shavings to come from out of his sight, in order to give him more tension. I spent a good minute clipping all the hair off his back side. As it began to become burred, Billy began to look more like a he-man. He had a small scar near his crown, and it showed up when I swiped over that area.

I stopped the cut when all the hair was gone from his back side. I took a brush and brushed off all the loose hairs on his head. I then lowered my blouse and rubbed my breasts on his freshly burred head. Billy was starting to get hard and creamy, and it was visible in his pants.

The next swipes came around his left side from back to front. Billy finally got to see huge clumps of hair meeting their demise. He began to take his hand and rub where he was now close to bald.

After finishing the left side, I took away the right side. Now, all that was left was his top. Normally, when you shave the top of a head, you do it from behind and pull the clipper back toward you. I decided to get in front of him and make sexual facial expressions and sounds while I shaved him the opposite way. By now, Billy was about to cum. I quickly finished the cut and took my hair dryer to blow away all the hairs that had fallen about him. I brushed him all over his head and neck and removed the cape. Billy looked more like a lifeguard at the beach than the 20-year old virgin that he was. By now, I was extremely aroused and ready to explode myself.

Our first foray in the bed didn’t last long, and I knew it wouldn’t. I got on top of Billy
because he was unsure about taking the lead. I inserted his stiff penis in my vagina and in about 10 or 12 thrusts, he exploded and then collapsed. I was on the verge of doing the same, and I kept going even though it appeared that Billy was temporarily paralyzed by this experience. In about 15 seconds, I began to have a long, protracted orgasm. It was multiples right off the bat. I had never experienced anything like this myself.

20 minutes later, I woke Billy up and cleaned him up. Then, we started over again. Now that he had cum hard, it would take a while for it to happen again. This time, the condom broke, so we went ahead and did it without it. Billy felt much better with his bare skin. I realized how much I enjoyed being on top and from that moment on, I only had sex when I was on top, except the week I tried to get pregnant.

Billy came again, but not until I had experienced another multiple orgasm. I had rubbed his burred head so hard, it was starting to get red all over.

We only left the apartment to walk to the nearby pizza parlor on Saturday night and to go buy oil to give each other hot oil massages on Sunday. The rest of the weekend was spent in my bedroom or in my bathtub.

Billy and I kept having sex for the next few months until it was no longer a novelty. We remain friends to this day even though we have other partners. Billy keeps coming in like clockwork every two weeks to have me cut his hair. He has transitioned into a short flattop because his new girlfriend likes it that way. She occasionally accompanies him to the shop to watch me buzz him, but she has no idea about our history, nor does my current boyfriend know about it. I think one day Billy and I will hook up for another long session. I really want to un-flatten that top and shave him to clipper stubble. Now that he knows about this website, he will read this and hopefully plan how it can happen.