Back to Modesty 2: An Obsession

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It had been 6 months since I decided to completely transform my look, with support from my boyfriend Jon and unending nagging from my mother leading me down a path to discover a new sexual magnetism toward transforming my look and becoming a new person in the salon chair and clothes store changing rooms.

Since then, I had forgone my old long silky hair for blunt cut bobs and even blunter fringes, keeping it trimmed with regular visits to the hairdresser and my fringe neat with a pair of grooming scissors. My wardrobe had completely changed, from skinny jeans, low cut tops and fashionable lingerie to flared, bootcut and wide leg trousers, turtlenecks, skirts, flat shoes, collared shirts under cardigans etc. I had never felt more myself being so modest. Guys who used to stare at my in class, no doubt into my stylish look now didn’t glance my way, and I liked it like that.

I had found in myself an unusual sexual desire for me to be conventionally unattractive in public. All I cared about was Jon, and he was really into my new look. Our sex life had never been better, and he would often encourage me to keep my hair neat and short, fringe blunt and would often help my choose outfits.

The second semester of my college degree was nearing completion, and I was now sharing a dorm room with Jon. We would often look online at retro hair cutting videos, arousing ourselves at the thought of me having another transformation. It was all so exciting, and we knew it was a matter of time before it was going to happen again. We started watching girls of a similar age to me getting retro style haircuts, bowl cuts, wedge bobs, perms, and shags, and would sit in silent admiration of their transformations, while I stroked Jon to full hardness, before we engaged in our intercourse. This was becoming an obsession for both of us, and our secret fetish we could share with one another.

It wasn’t long after we discovered the retro hair transformations that Jon clicked on a video of a woman getting her hair cut to a pixie, then the clippers met her forehead, taking her down to a 4 all over. I was unsure about these transformations at first, but I had never seen Jon so aroused by the videos. We went down the rabbit hole of headshaves, Chelsea’s and buzzcuts for a while before I reeled it in and stuck with our usual enjoyment of short retro hairstyles.

I could tell that our desire for me to transform was becoming too strong, and booked in an appointment at the local salon to surprise Jon with, allowing him to choose which hairstyle I ended up with. I told him I didn’t want it too short, and sent him a playlist of videos containing styles I’d be happy with. The thought of a surprise haircut aroused me incredibly, and only served to increase our lovemaking and suspense.

The day finally came, and me and Jon got dressed, me in my now becoming usual flare black trousers, white shirt with a cardigan and ballerina flats which kept me looking prim and proper. I stared at my hair in the
mirror, and bid this style farewell for now, the Bob that framed my face and the blunt fringe which sat above my glasses creating the impression I was a 40 year old librarian, yet underneath was a sex driven 22 year old with an incredible secret.

We drove to the salon, and I was shocked to see a closed sign on the door.

“This can’t be right, I booked an appointment for today.” I told Jon.

“Don’t worry honey, just follow me.”

I was now dying of suspense- what did he know that I didn’t? We walked in the door and it was completely empty, before a middle aged looking woman came out from a door in the back.

“Ahh! You must be Jon, and you must be his lovely girlfriend. I love your look, so classic! Not many women these days wears such modest clothing.” I thanked her and blushed, still unsure what was going on.

“So, Jon informed me that he will be deciding your haircut today, as a surprise, is that correct? He’s not trying to trick you, is he?” She asked.

“Haha… no.” I coughed nervously. “It’s just something I suggested for a bit of fun.” I replied.

“Great. Well you take a seat, and take those glasses off, I’ll ask Jon what we are doing and then we can begin!” She said, locking the door of the salon and drawing down the curtains before putting the lights on.

I was now throbbing with excitement, and becoming a bit wet in anticipation. I could see Jon and the lady whispering to eachother, with Jon showing her photos on his phone, in the reflection of the mirror. I was dying to get this started.

“Ok honey, let’s get this show on the road!” She said, caping me up tight, while Jon sat down at the side. I could see that he had set his phone up on the window sill, recording this transformation. This made me even more excited, no more watching random videos on YouTube, we could watch me. The lady tilted my head forward and begun cutting around my nape. I was staring at my feet, two flat black ballerina shoes poking out of the cape, draped in a long flare trouser leg. I couldn’t believe how much I had changed in a year.

As the cutting began, I had to follow the scissors, as without my glasses I had no clue what was going on in the mirror in front of me. All I could see was my Bob getting shorter and shorter. Before long, it was up to me earlobe, and I began to feel her trim around my bangs, shortening them and blending them into my Bob. What could it be? The trimming continued, until she stepped away and picked up a pair of clippers. My heart started fluttering and I looked at Jon who simply smiled at me and gave me the thumbs up while I drew some breath.

She clipped a guard on, and begun to take my sideburns down. I had never felt clippers on my head before, and was elated. My crotch was sodden at this point, and I just hoped she didn’t notice how excited I was getting. More cutting began when my sideburn were shorn, and I noticed I begun to resemble a mushroom in the mirror.

It wasn’t long after the lady asked me to put my glasses back on, and I was shocked to see I had been given a bowl cut, tapered at the side, higher up than my ears. Now this was a transformation. I was ready to leave and enjoy this cut with Jon, however I looked again and they were whispering to eachother once more.

I sat and angled my head, looking at different perspectives of my cut. It was by no means stylish, but the sheer look of difference on me made me moist with satisfaction. I thought the Bob with bangs was enough, but this was unleashing a new monster within me. The lady came back towards me, and looked at my eyes in the mirror from behind.

“Alright darling. Are you ready for the next step? Your boyfriend told me you were all mine.” She asked.

More? More?! I thought to myself. But I was ready to submit to the scissors, and the look on Jon’s face told me this would be worth it.

“Um, sure.” I croaked.

Within moments, the clippers had been adjusted with a new guard again, and chunks began to fall from the back of my head. I sat with my mouth agape, I expected a pixie, not buzzed! Words couldn’t form, and I watched as my now bowled hair fell into my lap. She carefully took the length off the top of my head, leaving the short fringe that was blended into the bowl cut. What was left was a short buzzcut, and a short, half forehead length fringe. A Chelsea. I knew Jon liked those videos a bit too much. The lady finished off and handed me my glasses. What stared back was the most shocking image off all my transformations, a borderline hairless woman, with a pair of oval clear lens glasses the most prominent accessory on her head, framed by an out of place fringe.

I turned to Jon, and he recognised how shocked I was.

“Do you like it honey?” He asked.

“Yes… I… love it.” I swallowed. I didn’t know how to feel. All I knew was my sex was going crazy, I couldn’t think straight for my moistness.

The lady took the cape off me and went to discuss payment with Jon, which couldn’t have been cheap as he had rented out the whole place for this. I stood up but my legs were uneven. I felt my head and was met with a prickly sensation, and flapped around my fringe, which acted as an island of hair in a sea of near baldness.

“Are you ok?” Jon smiled, knowing I wasn’t.

“Yes, let’s just get home.” I thanked the lady and we went to the car.

“Was that enough?” Jon asked as he clipped in his seatbelt.

I looked at myself in the vanity mirror, before turning to him.

“Yes, this was perfect.” I leaned in to kiss him, and in the darkness of the night we made out violently, him rubbing my fuzzy skull, me climbing onto him in affection.

Before long, we realised we had to get home and finish the job. Jon arrived at our dorm, and as we walked back I couldn’t stop feeling my buzzed head and looking at myself in car mirrors. I wouldn’t have known what to say if one of my friend saw us. I was buzzed within in inch of my life, and Chelsea cuts weren’t exactly common.

We got home, and before I could begin kissing Jon again, he led me into his bathroom, where a bag sat on the counter.

“That wasn’t enough, was it?” He asked, grasping my waist.

“Jon, since I first cut my hair, it never has.” I moaned as he felt my thighs.

“Well I can help with that. I’ve got the ultimate solution here.”

He opened the bag, and revealed clippers, shaving cream and razors. I was so ready to take it.
I sat down on the counter, and let Jon shave off the little fuzz and fringe I had on my head, rendering me close to bald as I touched myself. He then lathered me up, however I couldn’t help myself, and pressed against his hardness, rubbing and thrusting as he shaved every last bit of stubble from my head. I unzipped my flare trousers, kicked off my ballerina flats, and undid his jeans, slipping him into me as I moaned with extreme pleasure. I watched in the mirror as he thrusted into me, shaving me bald. The razor finished on my head and ran down my forehead, slicked by the cream, onto my eyebrows. In our moment of pure pleasure, he shaved my head completely bald. I looked in the mirror and saw an alien, a bald alien being penetrated and controlled by a man.

We soon reached elation, Jon coming into me as I draped over the bathroom sink, moaning and looking at my bald head in the mirror.

“I think we should keep this for a while.” I gasped for air.

“Yes… I think we should.”

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