Back to Modesty

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It was a cold winters day in my freshman year of university when I first met him. My best friend Erin had taken the day off, and I was left sitting alone in my psychology class, until he walked through the door and was introduced to me as Jon. Jon stood quietly with books at his side, and was instructed by our professor to sit down beside me. He asked if I would run him through todays reading material, and help him catch up. I was more than happy to.

We got to talking and he told me he was in his second year, but needed to take this class to earn some extra credits. We laughed and joked with eachother and got on really well. That class ended and I had butterflies in my stomach, we exchanged numbers and I headed back to my dorm to relax and study for the night.

I slinked into my room and locked the door behind me, taking off my glasses and letting my ponytail down, getting changed into my joggers and hoodie to relax for the night. My mind couldn’t escape Jon, how he was so sweet and kind, happy to speak to a shy girl like me. I think I officially had a crush.

The next day I had a shift at the campus coffee shop, free from classes. On my lunch break I sat and drank my latte when my phone buzzed, a text from Jon. My heart skipped a beat, and I went to respond.

‘Fancy coming to my dorm later? We can head out for dinner if you’d like :)’

With that I put down the phone and smiled to myself, hoping no one noticed, before gathering my thoughts and replying.

‘Of course! What time?’

And with that, our relationship blossomed. Months went by and we were inseparable, I struggled concentrating in my lectures due to his presence. We could have fun and enjoy each others company wherever.

Our sex life was fun too, it had been years since I’d had a boyfriend and was happy to be back, exploring a partners body and sharing in the love. However, Jon began to lay hints at a more intense kind of romanticism.

I have had silky auburn hair for my teenage and now young adult life, which I took great pride in, since I was forced to keep it in a chin length Bob until I was 16. When I finally had autonomy over my hair I decided to grow it out, and kept it that way, to my mothers frustration, but she knew I was old enough to make the choice. By the time I was 17, I trimmed it back down to a shoulder length lob, just to keep my hair healthy. As couples do, we shared funny pictures of each other from when we were younger, and alas, I showed Jon a picture of me, 17 years of age with a freshly chopped lob, which I could now admit characterised my features nicely. I was now 21, and so was Jon, so this was a few years ago. The laughing stopped and Jon caressed my face, looking at me sheepishly.

“Wow, I didn’t realise you could pull off short hair so nicely”. He smiled.

“Well, it has been years and my face has changed a bit… I’m quite happy with my long hair now. It took ages to grow out”. Butterflies began to stir once again.  Just like my mother used to tell me, I suited short hair, and it was ‘more tidy’ in her words. If she had it her way I’d be wearing skirts with a tidy chopped Bob to this day.

“I’m imagining you with short hair now, and I can totally see it”. Jon kissed me, and my cheeks blushed.

“Yeah, it was pretty manageable to be honest”, I whispered between kisses. The kissing grew more intense and evolved into lovemaking, to which Jon seemed more excited about today.

Another month flew by, and our relationship continued to improve and we were getting to know everything about each other. By this point it was coming up on Christmas, and we would soon be heading home for the holidays. We came from the same area, different schools as it happened, so it wouldn’t be an issue to see eachother, just a half hour drive.

As I went home for the holidays, I took Jon with me, introducing him to my family and they were very supportive. We settled in my old bedroom for the night, where I showed Jon all my old belongings and stuff I left behind when moving for university.

“Check out these old clothes. I was 17 before my mum let me hear skinny jeans.” I professed to Jon, holding up a pair of bootcut black trousers that acted as a uniform for most of my high school days.

“Hell, these might still fit.” I tried, pulling them on, giving me a more modest, professional look.

“They suit you babe.” Jon remarked.

“Thanks, I guess I just abandoned all this when I had some freedom as an adult.” I replied. I also pulled on an old sweater which was the opposite of revealing, a turtleneck burgundy jumper that I used to hide under in school.

“And check these out, my old glasses.” I held up a pair of clear lensed oval rim glasses, which did the job before I upgraded to a more stylish pair. I looked in the mirror and was startled to see a more grown up version of the teen I once was, shy, in reserved clothing with chin length hair that was now down to my breasts.

“You look cute.” Jon smiled and held my from behind.

“Are you kids coming down for dinner?” My mum bellowed from down the stairs.

“Yes, just coming!” I replied.

Me and Jon got up and went to join my family at the table. My mum was startled to see me in my old modest trousers, turtleneck and glasses, but soon complimented me and asked Jon if he preferred this to my more stylish, revealing clothes I frequently wore about campus.

“God, that suits you so much. I don’t understand why you have to follow those trends, you were such a nice looking young lady, isn’t that right Jon?”

Jon nodded, he didn’t want to upset me or co-sign my mothers condescending remarks.

“And I wish you’d cut that hair again! A nice short style would do you the world of good in university. Less maintenance, so you can focus on your studies!”

“Alright mum, I get it”. I barked back. She settled down, but I couldn’t lie, it was nice and familiar to be back in my old clothes, comfortable and modest.

As we finished up dinner, me and Jon headed back up to my room, I slinked up the stairs and felt strange as my bootcut trousers flapped around my ankles again, instead of the skin-tight jeans I normally wore.

“I have to admit, your mums right.” Jon said cheekily as he sat down on my bed. “You look professional. Less revealing means less competition for me!” He said laughing.

“Alright you.” I kissed him on his forehead.

As I looked at myself in the mirror I held my hair up to my chin, simulating how I’d look with a Bob again. This shocked me even more, it gave me a feeling deep in my stomach I wasn’t prepared for.

“It’s an idea.” I whispered, and coughed, trying to hide my arousal at my new/old developing look.

I stared down at my clothes I arrived in, which were now in a bundle on the floor. Tight jeans, low cut shirt and white sneakers. Maybe it was time to be a bit more professional, I was 21. Clothes like that were for teenage girls.

We got ready for bed and instead of taking my revealing nigh set out of my travelling case I opted for my button up collared gown I used to wear, courtesy of my mum. Jon didn’t comment, but he knew I was transforming, and found satisfaction in this new look.

Then next day arrived and Jon had to drive back to his parents house, across the county. I bid him farewell and returned to my room, looking at photos of myself with my old Bob, which soon developed into feelings of arousal. I couldn’t help it and soon began touching myself at the idea of transforming my look completely. Imagine going back to college, no longer one of the ‘cute’ girls, rather one who dressed modestly and wore her hair short and tidy.

The idea began to take over my mind, and before long I was trimming the ends of my hair in my bathroom with a pair of scissors I took from my mums home grooming kit, which she used to trim her blunt bangs between hair appointments. Millimetres became centimetres, and when I nearly took an inch off my hair I decided to relieve myself of the feelings and call Jon.

“Babe, I’m really thinking about cutting my hair.” I said sheepishly.

“Listen, I think this is what you want honey, I can tell. The clothes you’ve started wearing, the glasses, all of it. You seem to want a big change, and I can’t stop you. Im sure you’d look fantastic whatever length of hair you have.” He was so supportive of me.

And with that, I phoned up my local salon I used to frequent for my short haircuts, without informing my mother or Jon. It was Monday, I had an appointment for that Thursday, and was due to see Jon that night at his house. As the days passed butterflies continued to grow, the thought of sitting in that chair again limited my concentration on my midterm essays, and fully occupied my mind. I didn’t tell the hairdresser what I was after yet, as to be honest, I didn’t know.

I scoured the internet for photos of lobs, bobs, and even shorter. I had hatched a plan to ask for a lob, and if I wasn’t satisfied, take it shorter to a Bob, then possibly chin length. The thoughts made me wet, and it was becoming an obsession in more ways that one.

Thursday finally came. I got up and dressed in an old pair of high waist flare jeans, which were not the fashion at the time I wore them as a teenager. I stood out in high school wearing these. But now, I wanted to blend in. I put on an old collared sweatshirt, some plain black slip on flats which were almost hidden under the wide trouser leg, chose my modest oval clear glasses and got in the car. As I looked at myself in the vanity mirror of the car, my stomach did backflips. I had to remind myself that this is what I wanted, not to be dressed like a teen, or any of my peers. I had a desire to be modest, clean cut, professional.

I walked up to the salon door and was greeted by a receptionist. She told me to take a seat where I observed other people getting their haircut. I saw a girl of similar age to me, getting a blunt fringe cut into her long blonde hair, which only served to excite me further, I crossed my legs and tried to calm myself down.

“Hey sweetie, are you next?” The lady said while drying off the aforementioned girls hair.

“Yes, I think so.” I said sheepishly, my voice croaking.

“Ok, five minutes, just finishing up here.”

I was transfixed on this girls hair, the bluntness of the bangs caressing her forehead, nearly hiding her eyebrows. Looks like I had found another level to my transformation.

“Alright sweetie, come take a seat.” I was waved over by a nice old lady who was to be the artist of my transformation.

“So, what are we doing today.” She asked, wrapping me tightly in a black salon cape.

“Well, I was thinking of taking quite a bit of length off, a lob maybe?” I sheepishly inquired.

“Sure honey, no problem.” She said, like it was the most normal thing in the world.

My stomach turned, and my heart was beating fast. I took off my glasses and placed them on the desk in front, leaving me a bit blind to proceedings which the idea of continued to excite me.

Soon, the scissors were plowing through my long hair, and I watched as whisps fell to the floor, feeling my head get lighter with every stroke. Soon enough, the kind hairdressers was done,  and asked if the length was good. I turned my head 45 degrees to see, and wow, the length difference was staggering, and I think she noticed my shock. But it wasn’t enough.

“Well, I was thinking a little bit more. The lob was just a start, to see how I feel, can you take it shorter?”

“Of course.” She smiled, and the process began again, riling me up as the scissors took inches away again.

Soon, my Bob was forming, about mid-neck length, and I was looking on at the blurred picture in the mirror with fascination.

“Any shorter than this?” She asked, midway through chopping more hair off the bottom of my now much shorter head of auburn.

“Yeah, that would be great, I’m thinking chin length?” I swallowed as I said this, and I think she started to notice I was enjoying this transformation.

“Sure honey.” She said with growing bewilderment yet understanding I was just testing the water with every stroke of the scissors.

Soon enough, my chin length Bob was back, and it was incredible to see. I looked down, shaking my head and whisps of hair grazed my chin, a sensation I hadn’t felt in 5 years.

“Is that alright for you?”

I hesitated before answering. I felt my stomach rise, and the wetness underneath my flared jeans began to swell. I coughed out my answer.

“That last girl you had- would you be able to give me a similar looking fringe?” I asked, relieved that I got it out.

“Sure, a blunt, straight across full fringe, is that okay?”

“Yes.” I said, assuring myself that this was what I wanted.

Work began on my new fringe, and hair fell on my face as the scissors grazed my forehead, leaving a full fringe behind that covered a third of my face. I was now in a state of elation. I  began to sweat and could feel the wetness in my crotch swelling. As she dried off my hair I saw the image of a chin length Bob, complete with a full fringe form in the mirror. I couldn’t wait to put my glasses on.

I was then freed from the cloak, and the nice hairdresser handed my my glasses, in what second felt like minutes of anticipation. I put them on and my new image was revealed to me in all its modest glory. I looked almost like a librarian, smart, professional, with my collared sweater completing the look. I felt like a different woman, completely different to the long hair, trendily dressed girl that arrived in town days before.

I left the salon and the feeling was sensational. The wind took up my fringe in what was a feeling completely new to me, pushing my chin length hair upwards, with not much give.

I got into my car and stared at myself in the vanity mirror, entranced by my new look. I compared myself to pictures taken only weeks before on my phone, and the feeling inside me grew into a frenzy. I had to go home and sort this out.

I arrived home and quietly stepped in the door.

“Mum?” I said sheepishly, before she came round the corner with a shocked look on her face.

“My darling! You look so much smarter with that hair!” She hugged my tight, feeling my fringe and the bottom of my Bob. “I have my sweet modest girl back!” She was elated.

I walked away, happy that she accepted my new look, and headed to my room, staring at myself in the full length mirror, aroused by what stared back at me. I slipped my clothes off and got into my collared nightgown, leaving no pants on,  so I could enjoy my body in full, exploring the intense wetness. I felt my hair, the sensation was incredible, the shortness of it was causing me to have the best experience of my life.

I cleaned myself up and prepared to go see Jon. Complete in my black ballerina flats, collared shirt and black wide leg trousers, I was nervous as to what he would say, however as I knocked on his door it all flooded away with the smile on his face.

“Babe… you… look… amazing…” He exclaimed, and hugged me, again feeling my hair as my mother did.

“I never thought I would find you this attractive… without, yknow, hair… and tight clothes. But you look amazing.” He struggled to get his words out, but I just smiled and followed him up to his room.

Our relationship continued to flourish, and he would comment that my hair was getting a bit long, or my fringe was a bit unkempt. We arrived back on campus, and I would head to his dorm for fringe trims. It was an incredible sexual experience for us both, my transformation. He had a new me, a modest one, comfortable with her sexuality and her self. Shy, but happy. My friends all commented how strange the transformation was- but I didn’t care. I was me again. I was free from trends, free from long hair. Free to be modest. However, I had found a new feeling inside me, one that yearned for change, sexually. One that couldn’t be satisfied. It wasn’t long before I was showing Jon even shorter hair, and we both made love to the thought of it all.

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