About 6 months ago I got lucky and had 2 beautiful collage girls for roommates living in my house. They were both tall about 5’11” 130 pounds or so Amy had long brown hair to the middle of her back and Jen had dirty blond hair slightly past mid back that needed a healthy trim to fix the frazzled split ends. Amy’s hair was in perfect shape and she was proud of it. We had a few drinks that evening and Amy told Jen she needed to take better care of her hair. It looks really frizzy and dry. Jen gave Amy a dirty look and said she was planning on going to her stylist this Saturday at 10 to get it trimmed.

I wanted to see Jen with short hair, I had a “thing” for girls with short hair, and fantasized about seeing Jen getting her hair cut short. I had asked her if she ever considered cutting her hair short and to my surprise she said yes but she always chickened out when she got to the stylist. I told her she would look amazing with a nice short layered style and Amy agreed. Jen sighed and said maybe someday I will do it but I’m not ready to part with my long hair. I jokingly said awwww no short haircut for Jen tomorrow then I guess and pretended to be upset about it. Amy giggled. Jen smirked and said Don’t guys like long hair more than short hair? I said not me, I much prefer a girl with short hair over long hair, in fact I convinced 2 of my girlfriends to cut there hair short shortly after we began dating. Cutting there hair was a incredible experience I will never forget. Jen asked why was it so special? Uh Oh I thought should I tell her about my hair “thing”… I wanted to but not with Amy there. I really liked Jen and hoped that someday we might get involved with each other. So I I played it safe for the time being and said that we had a lot of fun doing it.

It was getting pretty late and Amy said she was heading to bed, said goodnight and went off to her room. Jen was absentmindedly playing with her hair as she sipped at her drink. That was getting me a little excited, wishing she would ask me to cut it nice and short for her. I imagined what it would be like to clipper her neck and give her a short layered little boys cut. The thought made a huge bulge appear in the crotch of my pants. I wanted to do all sorts of things with Jen in the worst possible way but didn’t think she would be receptive to me so I dreamed about her. That only made my crotch begin to throb and strain the seams in my pants more and more.

Jen asked me if I would be able to drive her to town for her appointment with her stylist, and said lunch would be on her after she got done. I smiled and said I’d like that , and asked her what time she wanted leave and Jen said around 9. If you wouldn’t mind could we make a few stops on the way home? I said not a problem Jen anywhere you want to go just say the word and were there. She smiled and said thanks, I need to pick up my mail at my PO and pay a bill. Jen smiled and said I’ll see you in the morning, I’m off to bed. Goodnight, and she went to her room.

I sat there and thought about tomorrow, even if she was only getting a little bit trimmed off I was going to be there and get to see her get her hair cut. I was close to cumming in my pants and hoped I could control myself tomorrow. That could be embarrassing if something like that happened! What I didn’t know is tomorrow was going to be a “turning point” in our relationship. One that would test my resolve to it’s limits. Tomorrow was going to be a very exciting day…

At 9 the next morning Jen and I were on our way to town and a turn of events that would change both our lives forever. Jen asked me if what I said last night about short hair was really how I felt and I said defiantly. Wow, Jen said, thats kind of interesting and refreshing in a weird sort of way. Every guy I’ve gone out with, well lets just say they hated the idea of me getting my hair cut. Jen didn’t say anymore about it and we arrived at her stylists shop a while later. I hold the door open for her and follow Jen into the shop. Jen talks to the receptionist a bit and I sit down looking into the shop and see a stylist that I couldn’t take my eyes off. She had a very short tapered back and sides boy cut that made my heart skip a beat! Oh My God she was a very sexy looking woman.

Moments later I hear Jen shriek and say Oh My God! Julie! Your Hair! It’s gone! She ran up to her friend and was at a loss for words until Julie grinned and said she wanted a big change so a week ago after the shop closed she had one of the girls cut her hair. Jen told her she looked stunning. Simply stunning. Julie smiled and said thanks. I’ll be done in about 10 minutes. I’ll come get you when I’m ready. Jen came and sat down next to me and was telling me about her friend Julie and how she had hair down to her waist the last time she saw her, last weekend she had her friend cut it. I am so surprised. I mean she looks fantastic!

I’m still staring at her friend nodding my head and continue staring at her. Jen notices me looking and suddenly she feels unsure. Jen wonders if I would stare at her if her hair was cut like Julies…. Jen is getting nervous and uneasy, she realizes that today could be the end of her long hair. Jen shudders and decides that she’s going to do it. She’s going to ask Julie to cut her hair just like hers. Jen puts all the doubts out of her mind and tells herself she’s doing it because she wants to do it….

A few minutes later Jen is laying with her head being massaged as her hair is washed and conditioned. Her eyes barely open but what she sees just makes her want to do it that much more… Julie looks amazing… Jen finds herself walking with Julie, she feels like she is dreaming or asleep, Moments later she hears Julie asking her if she wants the usual.

Jen manages to say in a nervous voice no, I want it cut just like yours…. I want a short layered boy cut! I see Jen talking to Julie and see Julies look of surprise and wonder what is up…. Then I see Jen nodding and Julie gathers Jen’s hair up and in one swoop hacks her long ponytail off almost at the scalp!!! Then Julie puts the tail and her scissors on the counter and picks up her clippers… Holy Shit I think Jen is going for it!! She told Julie to cut it like hers!! I watch as Julie begins to get very serious running the clippers through her hair. My Cock is throbbing madly. Another pass of the clippers and I feel my throbbing cock oozing and hope no one will see the wet spot… Jen turns and looks at me smiling. I smile back and blow her a kiss which she returns to me!

20 minutes later Jen is standing next to me just beaming as she looks in the mirror. I’m speechless. She is the most beautiful woman I have ever seen. I tell her that and she kisses me and then she notices my obvious excitement the huge bulge in my pants and giggles. Julie sees it too and says to Jen, I think he likes your new look! I take my wallet out and hand Julie a hundred dollar bill telling her to keep the change for doing such a fantastic job on Jen’s hair and walk towards the door with Jen close by my side.

We barely get to my car before we are grasping and grouping each other like animals. We get to the car and once inside Jen is taking me in her mouth outside of Julies shop. Moments later I explode in her mouth and feel her hungry mouth draining every drop out of me and licking her lips she sits up and says lets head back home OK?

I smile at Jen and say ya we can eat later…. and it wasn’t until 2am that night that we got “busted” by Amy as we were raiding the refrigerator! Amy saw us together, then saw Jens hair and giggled. She said, I wondered what all that commotion I heard was… I could hear it a block away! You two sex starved kids were tearing the house apart eh? It’s about time Amy said giggling Happy that two of her best friends had found each other. Amy smiles and said must have been one helluva day… and I grab Jen and drag her back to my room saying and it ain’t over yet either as Jen squeals with delight!