The Best First Date

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I was 30 and I’d just gotten a divorce from the man I thought I’d be with forever.

Until our relationship went south for several reasons, we’d been very compatible. Well, in most ways, except one big thing.

I have a major haircutting fetish.

I’d bring it up to him off-handedly, saying things like, “Wouldn’t it be hot if I had short hair?” or when I’d come home from the salon, “Something about getting my hair done really turns me on.” He was not into short hair on girls, he told me, and laughed it off when I tried to admit it, telling me I was being weird. I had resigned myself to only being able to enjoy my fetish in private, watching videos while quietly masturbating when he was playing video games in the other room.

Our sex life was good, but I deep down I knew it was missing something for me.

The longer we were together, the more traditional he got. He even ended up asking me not to cut my hair at all for a long time, said he wanted to see it get as long as possible. Even though I longed to have my hair cut, him asserting any control over my hair was somewhat arousing, so I did what he said.

The day he moved out, my thick brown hair had grown to fall in waves to my waist. I had to admit, I did look good with it and got a lot of compliments from people on how healthy it was.

After a few months of settling into the new rhythm of my single life, I started to wonder what it would be like to be with a man who actually understood my secret fetish.

I went online and posted a personals ad:

“30 year old female in AZ with haircutting fetish seeks attractive male for FWB situation. I’ve never acted on it in real life and want to explore this side of myself with someone who gets it.”

Maybe I was naive, but I did not expect a ton of responses and was immediately inundated with more messages than I could keep up with. Lots of men came in way too aggressive. Many of the messages had horrible grammar. Several accused me of being a catfish or scammer. But one stood out:

“Hello, my name is Drew. Your message stood out to me. I’m a 34 year old living in AZ as well and I also have a haircutting fetish. I’ve never told anyone about it before and just being able to share this part of me would be amazing. Your boundaries and comfort are the utmost priority to me.”

He and I started exchanging messages and as our conversation continued, I grew more and more excited about him. We were into the same things. We both fantasized about giving and receiving. He sent me a picture of himself and he was tall and handsome with probably 6-inches of brown hair falling around his face. I sent him a picture of myself, picking one where my hair looked the best.

After telling me he thought I was beautiful, he admitted, “I’m going to be honest, I’m going to be dreaming about getting my scissors into your hair.”

We agreed to meet the following weekend.

I spent the days leading up to our meeting in anticipation, spending extra time brushing and playing with my hair, taking pictures of it. I do love my hair, but I also want it to be chopped off. This inner conflict is a weird feature of my kink—hair takes a long time to grow, and it can be gone so quickly.

I took an Uber to meet him at a bar downtown. Grinning, he pulled me into what would look like a hug of greeting to any onlookers, but I felt his hand grab my hair. He whispered in my ear, “I can’t wait to see this beautiful hair in piles on the ground,” before smiling and pulling out a barstool for me. I was soaking wet from the contact of him and his words and I could feel my heart pounding out of my chest.

Our conversation was flowing just as well as it had in messages and there was an obvious attraction on both sides. He took any opportunity he had to touch my hair and every time he did, electricity shot through me. He’d tuck a strand behind my ear or put a hand on my waist, tugging his fingers along the healthy ends of my thick hair.

I hadn’t been with someone new in so long that I was filled with excitement and nerves, a feeling compounded by the fact that I was about to live out my biggest fantasy. We finished our drinks and I asked him, “So, want to head back to my place?” Grinning, he called for the check.

In the quiet of the parking lot, he grabbed my hand and led me to the passenger side of his car and took a long look at me, up and down. I knew I was looking good in my sundress, which hug my curves, and he was wearing jeans with an impeccable fit and a white t-shirt.

I touched his hair for the first time, it was silky and brown and felt amazing in my hands. I gave it a little tug. “Your hair is going to look so good falling against your white shirt when I buzz it all off. It’s almost a shame because it’s so pretty.”

He growled low in his throat and abruptly lifted me off the ground so I could wrap my legs around his waist as he slammed me against the car door and we passionately kissed. I could tell he was hard as a rock and packing major heat through his jeans as he gave a few thrusts against my soaking panties. Our hands were all over each other’s bodies, especially our hair, and we both knew exactly what it meant to the other person:

“This beautiful hair is about to be mine. You are about to lose it tonight.”

We couldn’t get to my place fast enough. On the car ride there, we discussed boundaries and desires and a safe word, making sure that no matter what happened, either of us could stop anything at any time.

When we got to the house, we practically skipped up my front steps. He’d brought a bag with him, and he asked me, grinning like he couldn’t believe his luck, “So, where do we want to do this?”

I lead him by the hand to my bedroom. Together, we worked as a team, setting out all of our implements, getting a chair ready, setting up my full-length mirror. We wordlessly knew exactly what we needed.

When we were ready, he stood behind me in the mirror and gave my shoulders a little squeeze. We looked good together, he and I, and our long brown hair complemented each others.

“So,” he offered, his voice slightly shaky with desire. “Who’s up first?”

I leaned forward a bit so I could grind my ass against him for a while until he moaned. “I am,” I told him.

His eyes lit up and he leaned down to pull my dress over my head and threw it to the floor. I gasped. He unhooked my bra and added it to the pile. He then kneeled in front of me to slowly pull my underwear down so I could step out of them. He stood back up behind me so I could see myself totally naked in the mirror, except for my hair that covered  both of my boobs and most of my body to my navel.

“A goddess,” he said. “A Renaissance painting. I want to cut your hair naked because you’re a goddess and you deserve to be worshipped for this beauty you are about to give to me.”

He took his time combing through my long hair, kissing me and whispering little words of affirmation to me as my entire body lit up with sensations. My hair was tickling my nipples and I was almost sad that feeling was about to go away.

That is, until he started kissing my neck. “Such beautiful hair,” he said, “But it’s covering your neck, and we can’t have that. So it has to go.” That gave me shivers as he firmly took my hand and lead me to sit down in the chair right behind me.

We’d agreed in the car that I wanted to go to a chin length bob and that we’d check in from there to see how I was feeling and if I wanted to go shorter.

The shortest my hair had ever been before was collar bone length, so the idea of not being able to bring my hair into a ponytail was unthinkable.

It’s as if he read my mind as we saw the hair tie on my wrist, and cut it with the scissors.

“You won’t be needing that anymore,” he grinned.

The cutting sound sent shivers down my spine. Noticing my reaction, he lightly dragged the scissors across my body, leaving a light white mark on my skin and tingles everywhere it traveled—my arms, my breasts, my neck.

He pulled my face to his from behind and kissed me deeply while opening and closing the scissors in my ear, just to tease me with the sound.

“The question is,” he asked aloud, pulling back to slowly rake his hands down the length of my thick hair, “do I cut it off in stages? Or all at once?”

He made eye contact with me in the mirror and used his fingers to mark where he could cut it. “I could just cut here,” he pointed to what would be a modest trim of just a few inches.

“No,” I moaned.

“Oh, you want more?” he asked, teasingly.

I just nodded and he chuckled to himself. “What about here?” he pointed to the tops of my boobs, which would still be a major cut. I shook my head.

“I’ll tell you what, I’ll trail my hand up, and you just tell me when to stop, OK?”

He slowly brought his finger up the length of my hair, past my collarbone, then to my shoulder, and then to the middle of my neck, and then to my chin. He made eye contact with me since that’s the length we previously agreed on, but I didn’t say anything. His eyes lit up as he brought his finger even higher, to just below my ear.

“Stop,” I breathed.

He nodded and the confidence he portrayed cracked a bit as his hands shook a little as he brought the pair of scissors up against my jaw, opening them wide toward my thick curtain of hair.

He looked me deep in my eye. My lips were parting, my heart beating out of my chest. I’d never been more turned on or nervous in my life. “Are you ready?”

“Yes,” I complied, and he clamped his hand down.

A two-foot long tendril of dark hair fell down my naked body into my lap and even though this is what I wanted, what I longed for, I still started to cry as he made his slowly made his way around my head, throwing my long, beautiful hair into my lap. I wondered if I’d made a mistake, if I’d still be pretty.

The crunching sound of scissors echoed in my ears as I felt the cold metal make contact with my jaw and the back of my head.

When half of my hair had been cut off, Drew whispered, “Oh, look at you,” as he kissed the tears off my cheeks, and then moved aside so I could see myself in the mirror. I looked in the full length mirror and saw my naked body, with my legs spread, with long tendrils of my cut hair covering my body, spilling mostly into my lap. I picked up a piece of it in my hand.

“So long,” I whispered, in a daze of arousal and a little shock.

I looked back into the mirror and took stock of the contrast between the left and right sides of my hair. The left side was still long, covering my breast and curling almost to my thighs when I was sitting. The right was cut severely, above my jaw. I turned my head from side to side, observing how I looked with both lengths. I was worried if I’d be able to pull off the short bob, and I had renewed confidence in the fact that I could. “Keep going,” I said, and Drew wasted no time slicing through the rest of my hair so that both sides matched. After, he took his time evening out the sides, making snips here and there.

“You look beautiful,” he said, running his hand through my shortened hair, giving it a tug and pulling me back for a kiss. He reached through the pile of hair on my lap to find my soaking pussy with his free hand and took his time rubbing my aching clit with his thumb until I was quivering and then slid two fingers inside me roughly, rubbing against my G-spot until I erupted in a quaking orgasm.

He held me as my body went limp and he whispered sweet words to me as I came back to life. I nuzzled into his body and said, “You ready for your turn?”

He nodded and we traded places. Me, still naked, and him, still fully dressed. Something about the contrast of that was hot. I kept sneaking looks at my hair in the mirror. Having no hair to hide behind really made me feel confident, like I was standing up straighter. “I know I said early that I wanted to see your hair fall against this shirt, but I think I want to cape you up for this,” I said, and he grinned and nodded in a way that made it seem like that’s exactly how he wanted it.

I dragged the white cape around his shoulders and secured it tightly around his neck. I leaned over to whisper in his ear, “Last chance to back out of this, because when I start, I’m going to be ruthless.” He looked at me and just smiled, so I kissed him on the jaw and took a few minutes combing out his hair, a part of me lamenting that it was going to be gone so soon.

I bent over in front of him to grab the clippers, knowing it would give him a full view of my ass and pussy. He moaned as I did it and I innocently looked over my shoulder at him. I plugged in the Oster clippers he brought and turned toward him. “I’m not going to bother putting a guard on this,” I said and then walked over to straddle his lap. I flipped the clippers on and could feel his already hard cock get somehow harder just at the sound of it in his ears.

I thought again about how amazing it was to be with someone who got it, who got me and the deepest nuances of my desires. And on that thought, I shoved the clippers into his hair, right down the middle. I worked quickly, reducing his hair to the barest stubble, pressing his head into my breasts so I could reach the back and around his ears, whispering words of encouragement to him as I made quick work of my task. I was rolling my hips against him and extremely turned on by the feeling of power I felt.

I turned the clippers off and he held me closer to him to he could look at himself in the mirror. His eyes were wide, but I could tell he loved it. My body was covered in hair from both of us. I rubbed my hands along his stubbled head and he moaned in pleasure. “That was one of the hottest things that has ever happened to me,” he said.

“Same,” I said.

From his vantage point in the mirror, he could see the back of my hair. “You know, it’s up to you, but I really think your hair would look even better if we cleaned up the back with the clippers. Even like an undercut.” He ran his hand along the short hairs at the back of my scalp.

I shouldn’t, I thought…My hair was short enough already. I took a peek behind me in the mirror, and realized he was probably right. It was so short that the bottom part looked a bit untidy.

“Do you think I’d look good?” I asked.

“I think you’d look incredible.”

“Then do it.”

We switched positions again and I took note of the enormous pile of hair on the ground, his and mine commingling. It was honestly one of the most beautiful things I’ve ever seen.

“Does the buzz cut feel amazing?” I looked up at him as he removed his cape.

“The best feeling in the world.”

I smiled and looked in the mirror. “Do you think I would look good buzzed? Like all over?” I ran a hand through my bob. I did like the way the short hair made my eyes stick out more, and my lips.

“You know I’d think you look perfect,” he replied, a little breathless.

“How about, like a 2 all over?” I asked him, a little shy suddenly.

He swiftly clipped the cape around my neck, popped the guard on the clippers, and met my eye. “You sure about this?”

Too nervous to admit it out loud, I just nodded before the clippers roared to life in his hand and he pushed them right down the middle, just as I had to him. The sensation was incredible. I couldn’t believe I was doing this as he mowed my once beautiful hair down to stubble, strip by strip. He worked around me as what remained of my hair slid down the cape, meticulously pushing my ears down to work around them and abruptly forcing my head down so he could get the rest at the back of my head.

I couldn’t look in the mirror, could only watch my hair slide on the cape and then into my hands.

When the clippers shut off, Drew looked at me. “Oh my God. You’re beautiful.”

He moved aside and I could see a woman staring back at me that vaguely resembled myself, but with a crew cut. We both ran our hands over my soft pelt. My eyes and lips were more pronounced than they’d ever been. I looked sexy and confident.

That night, we had the most intense and passionate sex of my life. I knew it wouldn’t be the last time we saw each other and indulged in our little shared secret…

(Let me know if you liked my story and I may write more!)

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