Adventures with the Pizza Guy, Pt. 1 by myboyfriendisbald

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Before I tell this tale I will give you a little insight as to who I am, and the scene of this encounter. I’m thirty two, female with long dark brown hair, and of average height and build. I inherited a barber shop from my father, along with the apartment that he used to rent out over the top of it. I now live in the apartment which I’ve remodeled to be much more comfortable and stylish. I live alone, though I do desire a partner. I cut both men and women’s hair in my shop, which I’ve rebranded since my father died to have a more relaxed, unisex, atmosphere rather than the dusty old school barber’s vibe of yeseteryear. I have a good number of clients, and I really enjoy what I do for a living.
Recently I’ve had a bit of an itch I couldn’t scratch, though. Most of my clients are regulars, who come in and know what they want. My walk-ins are few and far between, and they’re almost exclusively guys just wanting a quick tidy up. In the three years I’ve owned the shop I’ve never gotten to do a complete transformation on a head of hair. I really wanted to be able to plunge my clippers into a full mane and strip it down to a short short buzz, or take my shears to a long thick ponytail and chop it off, revealing a nice short bob. What would be even more exhilarating was doing so while either having a guy pleasure me, or me pleasuring them.

All of this brings me to what took place a few months ago. I decided to take a risk and post an ad online looking for someone to help me fulfill my fantasy. Rather than scare off a walk-in by scalping them unexpectedly, I decided to invite someone to my shop, and with their consent I would tie them down and enact my wildest dream. I didn’t expect a respond so quickly, but I ended up getting an email within two days of posting. It was a guy who claimed he was thirty and named Tom. He told me he had long thick blond hair that he’d been too scared to part with, but that he secretly wanted it gone. I wrote back and told him I was just the person for the deed. I told him a little about myself and told him we would need a safe word, which I suggested would be "pidgeon". He wrote back and gave me a time that was convenient for him, and the date was set! It would take place on a Friday night after my shop was closed for the evening. He would come around 8 pm and I could do whatever I wanted to him. He’d told me he was nervous, but to be forceful with him, as it would really turn him on. I was so excited to finally get to do a full transformation on someone AND get to live out my sexual fantasy!

On that particular Friday I got dressed up for the occasion in tight black pleather leggings and a tank top. I pulled my hair back in a long loose ponytail and put on my favorite lipstick. The closed sign was up, and now all I had to do was wait for Tom to arrive! Soon enough I heard a knock on the door and I went to open it. He was early, but that was more than ok with me! In the doorway stood Tom, with his thick hair flowing out from under a garish red visor that read "Pizza Emporium" on it. He was wearing a bowling style shirt with the same logo on it, and black trousers. He had one of those warming bags slung over one shoulder with what I assumed was a pizza box inside. I hadn’t expected him to come in character, but it was kind of fun! I took a good look at him, he was about six foot even and fairly lanky, but good looking. If it weren’t for the long greasy hair and sparse facial hair he’d probably be a real catch!
"Come on it," I said warmly, "You can just set the pizza down right there on the front desk."
He looked puzzled, but came inside anyway.
"You know, I’m closed, but I can make time for you."
"I’m just here to deliver your pizza," he said, removing the box from it’s sleeve.
"Ah, yes, of course," I walked closer to him and put a finger under his chin, lifting his gaze to meet mine, "But I’m sure you have time for a little trim, no?"
Tom shook his head, "Listen, lady, you’ve got the wrong idea. I have to get back to work."
"Don’t make me ask again," I whispered in his ear, "I can get testy when I don’t get my way."
Tom’s eyes went wide with confusion. He was new to this type of role play I guessed, but that was ok, I would lead the way. I took his hand and gently started to take him over toward my chair. He immediately resisted, "Wha-what are you doing? I said no!"
"But darling, this will make me so happy! And you want me to be happy right? You’ve already been so kind, bringing me dinner and all, now let me return the favor, won’t you?"
"Bringing you the pizza is my JOB that I have to get back to! If you want to return the favor just give me a tip and let me out of here!"
I gave him a stern look, and tutted, "Oh I don’t do favors in the form of money, darling."
I took his other wrist firmly, so my red painted nails dug in slightly. "Let go of me!" Tom started to squirm.
"You’ve hurt my feelings," I purr, "I gave you such a nice offer, and I asked so nicely, and you say no!" I drag him the rest of the way to my chair and push him down into it. I’d planned ahead, so there were already lengths of rope at the ready. Positioning one of my boots in line with his manhood to keep him immobilized, I began tying him down.
"You’re f-king crazy, let me go!" Tom’s eyes were wild, and he began to try to stand up, so I pushed my toe a bit more firmly toward his family jewels.
"Don’t insult me," I growled, "Wouldn’t want to have a high heel spike through your little friend now would we?"
Tom gulped and went ridged, his eyes were practically bulging out of his head, "I’m sorry," he mumbled, clearly deciding to try a new tactic, "You’re right, that was rude of me. What’s your name anyway?"
"Vanessa," I said, and glanced at his name tag, "And you’re Jake, I assume."
He nods and gives me a tentative smile, "So if we could just talk about this, Vanessa, I-"
"Uh-uh," I coo, "Don’t even try to sweet talk your way out of this Jakey."
I finish tying off the last knot which holds his left wrist firmly to the chair, and I step back. My finishing touch is slipping my candy-stripe cape around his neck.
"Look at you, all helpless. Doesn’t that just drive you wild, knowing now I can do anything I like with you?"
Jake’s face flushed cranberry, "Seriously, please, just let me go. I promise I won’t call the cops. I won’t tell anyone about this, ok?"
"Call the cops? Whatever for," I muse, starting to finger comb his long hair. It’s tangled and greasy, and I can tell he doesn’t properly care for it. All the more reason to shave it off!
"I don’t WANT a haircut!"
"Guys like you always say that," I reply, "And then once I shear them down like a sheep they’re left with a hard on and begging me to pleasure them. You’ll find you’re just the same, you can’t help it. There’s something very erotic about having your head shaved."
Tom, or Jake as he’d decided for the evening, begins to really pull against his restraints, "Oh no, no no no no! You are NOT shaving my head! I didn’t agree to any of this!"
"Oh but you did," I purr in his ear, "The moment you walked in. Now, any last words my darling?"
"Go to H3ll!" Jake spits on the floor. In response I grab a fistful of his hair and yank it hard.
"If you apologize for that, I’ll consider sparing you the straight razor."
Jake looks like he’s going to vomit.
I decided to get both my thrills in, starting with hacking off Tom’s hair with shears first, and then shaving his impromptu bob off with a #000 blade. If he decides to beg me, I’ll spare him the hot lather treatment, but if he’s naughty I’ll make sure he leaves fully bald.
I gather his hair back in one hand and unceremoniously fling his vizor off to one side of the shop. Posing sexily behind him, with my hand clenched around his ponytail, and my shears in my other hand poised to strike, I ask him in my most sultry voice, "Any last words?" If he was going to tap out for real, this would be the moment! Tom just gives me a bewildered and angry stare in the mirror, but doesn’t say a word.

His hair is so thick it takes me a while to cut off his tale. Little by little my scissors snip through the thick bundle, and Tom is slack jawed and red faced in my chair. As soon as I’ve made the last slice I take the severed hair and let it fall onto his lap. Tom looks about ready to cry, "Why are you doing this to me?"
"I told you, it will make me so very happy," I tousle his cropped hair, "And I promise, it will make you happy too. Just give in, and let the thrill take over."
"I hate you!" Tom looks ready to cry, "I din’t ask for this, I don’t even know you! I don’t care if you’re happy! I’ve been growing my hair out for years!"
"What a waste," I reply, "All that potential hiding under all that hair. Well, not for much longer!"
"You’re not really going to shave my head bald, are you?"
"That depends," I say, "Are you going to be a good boy and apologize for insulting me?"
He nods vigorously, "Yes, I am sorry. Please, please, please don’t shave my head."
I press a kiss to his lips and he shivers, "Just a nice clean buzzcut then," I purr, grinding myself gently against his crotch.
"No, just leave it alone!" Tom’s eyes welled with tears which I wiped with my thumb. Despite his protests there was a noticeable bump forming under the cape where the mass of hair lay lifelessly.
"If you insist, I’ll give you a #1 instead, since you did apologize."
I press another kiss to his lips and then lean back and grab the waiting clippers off the table. I put on the #1 guard, as I’m true to my word, and resume my position behind him. "I can’t wait to get my hands on you once all this hair is gone."
Tom goes white as a sheet when the clippers whir to life.
"Please," he cries, "I’ve never used clippers on my hair, please!"
"First time for everything," I coo, stroking his hair back from his face. I place the clippers dead center of his forehead and slowly draw them back. Fresh tears roll down Tom’s cheeks, but the tent in his pants grows larger when I stroke the newly shorn swath.
"See darling, it feels great doesn’t it?"
I make several more passes, then move around to the front of him and start clearing the hair around his ear with one hand, the other hand begins stroking his attentive member. Within moments he’s fully erect, and I’ve shaved nearly three quarters of his hair. I make quick work of the last quarter and then I switch the clippers off. I pull Tom in for a deep kiss and rub my hands over his freshly clipped scalp, "Doesn’t that feel divine?"
A soft moan escapes Tom’s lips and I reach down and stroke him again.
"You’ve been such a good boy, Tom," I whisper in his ear, "Don't you like being a hairless little boy for me?"
"My name’s Jake," he squeaks.
"Mhm," I purr, remembering his name tag, "That’s right, sorry Jakey boy."
I take the cape off him, and I’m just about to unzip his fly when I hear a knock at the door. I ignore it, and slip my hand down his pants, wrapping my hand around his thick girth.
"Tell me how much you like your new haircut," I purr in his ear.
We’re interrupted by another knock, to which Tom says, "You should get that. I’m not going anywhere anyway. I promise I won’t scream."
I kiss him tenderly and go to the door. When I impatiently throw it open I’m greeted by a stunning young man with long thick blond hair that flows over his shoulders. He’s wearing a black leather vest with nothing under it and dark wash jeans with rips all up and down them.
"Vanessa?" He smiles, "I’m Tom, I’m here for my appointment."

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