The Joys of High School
A true story……….
I don’t exactly know when it happened, but I have always liked short, or long, being cut, hair. The times where I can recall it most frequent and strong are about my freshman through junior year of High School. It started with my friend Ashley and has never stopped.
Ashley was a year older than I was but we always talked. I liked talking to her online, because I could say things easier. I felt somewhat awkward saying I wanted her to cut her hair in person. Nevertheless, she liked the idea and even had thought about a short style herself. With a little convincing I hopped in my car and drove her down to the nearest Unisex Salon. She had beautiful shoulder length curly hair that flowed to a little past her shoulders, but it didn’t suit her, she needed a short style to match her gorgeous body. When we arrived I asked her what style she chose and she showed me a picture of a stunning girl with a short pixie. I was ecstatic! The girl’s hair in the pic was almost cut to nothing on the sides and nape and was tapered up to a curly 1 1/2in. length on top. You should have seen the look on her face when she saw my eyes light up. But watching those clippers go to work on her was the most sexual thing I had ever seen. I quickly grabbed a newspaper to hide myself, because I could feel my cock start to harden, she caught a glimpse of this in the mirror and let out the most teasing, erotic grin. Good thing her parents weren’t home. We went back to her house and I couldn’t keep my hands off her neck, it felt so good. With that, she dragged me to the bedroom and off came her clothes – I WAS DYING! Being able to lose my virginity at 16 to a girl older than me, who just received the best haircut of her life was truly amazing.
Things were somewhat awkward in school but we got through it. She dropped out the next year, and I really didn’t see much of her. What I did see a lot of was Jenny and Cindy!
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I was now a junior and Jenny and Cindy were freshman. Just the sight of the two, I knew I had to do something. I started talking to Jenny (online of course) and she introduced me to Cindy. Jenny had a little longer than shoulder length hair and I knew it would be easy to get her to take some of the length off. However, Cindy was another story. She had long curly hair to mid back, it was dark brown and had never been permed or dyed and was so healthy it shone. A few weeks later I took Jenny to get the first haircut of many. She shortened her below shoulder length hair to chin length, in an incredible bob that fit her perfectly. We talked about her haircut the next day, but I could tell there was something there that was saying “shorter!” I asked her if she would like to go again next week for a trim and she immediately agreed. On approaching the salon I asked her if she wouldn’t cut it a little shorter and all she did was put a finger in front of her mouth, as if to say shh! Just the site of that was getting me aroused. We walked in and shortly after her name was called, a little lump started to grow in my stomach. I had to see what she was doing. She sat down and whispered in the stylist’s ear something that I thought was ear-length chili bowl cut. Jenny knows how the shorn nape drives me wild and with that, the scissors came out. Jenny’s hair was wet and the scissors were placed just above her earlobe. The scissors worked on a slight upward angle toward the back of her head. When the cut was finished the clippers came out and Jenny gave me a quirky smile that drove chills down my back. The stylist didn’t put a guard on and drove the clippers straight up her neck. Jenny looked great and the sex was better than with Ashley. I didn’t take my hands off her nape the whole time; she gave me a thrill!
I now had Jenny right where I wanted her; to be able to have her cut her hair whenever I wanted. And although I liked that a lot, I wanted a challenge… Cindy. Cindy was aware that I liked Jenny cutting her hair short and I frequently talked about it with her, but I never asked her to cut hers until now. She was a bit skeptical about it but was looking for a change. I talked to her about it for about a month and then the night came, the night I will never forget. Cindy told me Jenny was coming over and she would like me to come too, without saying another word I was over her house in 20 minutes. When I arrived, I didn’t see her parents’ cars so I knew something was up. I knocked on the door and to my surprise, Jenny answered the door in a short skirt and tight top with huge gold hoop earrings hanging below her freshly made chili bowl cut. Her nipples were coming through, I could tell she wasn’t wearing a bra, and she asked me to come with her. I felt my cock start to harden but tried to keep it tamed, I didn’t want to speculate anything. Jenny led me to the bedroom where Cindy was awaiting us, she was wearing the same thing as Jenny, and said, “We could be twins, everything’s the same except for the hair,” and after she said that Jenny let out a little giggle and kissed her on the cheek. They stared into each other’s eyes and began to kiss. I couldn’t believe what I was seeing. Jenny’s tongue was vigorously moving in and out of Cindy’s mouth and then they began to strip, each girl helping the other.
Once undressed Cindy looked at me and said, “I want to be a twin!” She then handed me a pair of scissors and the clippers and asked if I would do the honors. My prick was harder then ever now, and they liked it that way. She pulled up a chair and sat in it; she wanted to be naked to feel the hair falling on her shoulders, and back. I wet her hair and sliced the first snip at her ear, she never noticed it before but she had great ears, especially with the huge gold hoops that were hidden by her long mane of hair. I didn’t want this moment to end so I slowly made sure all the edges around were straight, then I plugged in the clippers. With no guard, I put them up to Cindy’s nape; I was so focused on cutting her hair I hadn’t seen Jenny in Cindy’s lap. She was helping along the orgasm, and doing it quite well. They started kissing once more as I pushed the clippers up Cindy’s nape. Three, now four, paths and one more to finish, she put her right hand back to feel it and exploded all over Jenny, but she just ate it up. Cindy loved her new haircut and looked great especially standing there naked; I couldn’t take it anymore and tore my pants off. I grabbed Cindy and threw her to the bed and savagely fucked her, while she fingered Jenny. The two were switching on and off, on who gets to be fucked. If I was fucking one than the other was being fingered. They even stopped me to have a little excavation on their own with a quick 69, while I played with their nipples. Sex lasted for hours and we all fell asleep in each other’s arms. I woke up a little later and just stared at the two of them in each other’s arms; naked and shorn.
I have a great life don’t I!