Fratboy to Femboy (part 2)

Part 2 (it hasn’t been to long since part 1 has it? *laughs nervously* sorry for the long wait)

Link to part one:

Fratboy to Femboy (part 1)

Please let me know what you think and whether you would like to see another part or more stories like this. Trigger warning for very explicit sexual content, feminisation, bondage, tattooing, piercing, femdom, spanking, S&M, bdsm and just a touch of masochism. Viewer discretion is highly advertised.

 

 

I pulled up beside where Amy eagerly waited on the pavement. She did a cute little hop as she realised it was me. God she was beautiful. Her hair was half up with two white ribbon tying the back corners of her crown, the midnight black locks beautifully curled. Despite the moderate weather, she was wearing a large wool jacket and a scarf as well as a short plaid skirt. Much to my delight her rounded ‘librarian glass’ also framed her delicate features. Her look was somewhere between comfy cottagecore and a dark academia ascetic.

“Sorry for keeping you waiting” I said as she entered the passenger side.

“You were perfectly on time, I was early” she planted a kiss on my lips before doing up her seat belt.

“Where are we going”

“Just an old friend, Kim’s, place I think I sent you the address”

“Oh that place I tried looking it up but it came to some closed café downtown”

“Yeah that’s it, it’s a tattoo parlour now Kim works there and she gets cheap rent on the flat above”

“Oh cool” Amy rolled her eyes at that comment.

We had been arguing about rent for a while. The two of us wanted to get a place together but we struggled to find somewhere suitable. The problem was mainly money, Amy had it, I didn’t. I wanted to be able to split rent down the middle but that left only a few cramped studios if we didn’t want to share with five other people.

Amy on the other hand had cash to spare. She had a significant trust fund, and her parents sent her money monthly to help with her studies. Not to mention, the portfolio of shares brought for her when she turned 16. Her plan was for us to get somewhere nicer even if she had to cover most the cost.

Something about that felt emasculating. It was strange for me to be embarrassed by that, she did stuff to me that most would consider far more emasculating. She was dominant in the bedroom and she enjoyed getting me to cross dress in her clothes. But, that was in private. I liked that despite that we had a pretty normal relationship. Normally, I would wear long sleeves and avoid shorts to hide my hairless skin. My hair was now long enough that I could throw it into a man bun without looking to feminine.

We talked a bit more until I arrived at the tattoo parlour. Amy lead the way. There wasn’t separate access to Kim’s place so we had to enter and go through the staff only backroom. We passed through another door and now arrived at a flight of stairs. Amy stopped and removed something from her bag.

“Really babe” I had an uneasiness in my voice.

“Yes” she smirked, holding out the pink and white collar with attached leash she would put on me during roleplay.

“But Kim”

“You think I don’t tell my best friend about our sex life”

“But…”

“Jordan” she interrupted me. I knew she only used my name when she was serious and I learned not to defy her when she was.

I leaded my head down. My voice softly begging “Please” as she ignored me.

The collar was strapped tight around my neck. I felt it being pulled forward as Amy used the leash to drag me up the stairs. She didn’t bother to nock, just pushing open the door to a messy apartment.

“We’re here” Amy announced herself.

“About time” a voice called back before a woman, who I assumed was Kim, walked into sight.

She was wearing a massively oversized t-shirt and shorts so short you could barely see them under said t-shirt. Her tanned skin was adorned with a few tastefully placed tattoos. What was most striking was her hair. Long, all the way to her tailbone except for the straight eye length bangs. It was dyed black with blonde underneath. Neither where her natural colour.

“And you’ve brought your boy-toy”

“Yes” Amy tugged on my neck in a way to keep me from speaking.

The pulling made me bow my head allowing for Kim to rub my head. She wasn’t as tall as Amy but I suspected still slightly taller then me.

“He’s cute”

“Thank you?”

“But I do see why you brought him to me”

What did she mean by that?

“Take a seat Jordan” she pointed to an uncomfortable looking reclined chair. It sort of resembled an office chair and was made out of a black plasticity looking material.

I wasn’t sure until my leash was pulled over towards the chair letting me know I was going there. The material wasn’t soft but also wasn’t uncomfortable having a slight amount of give. I leaned back expecting to feel the backrest but not feeling it. The pulling on my leash lead me to lean back further until I felt it when I was almost horizontal. Then I felt the neck rest but no headrest.

“What is this…”

Riiippp. The sound of Velcro straps holding first my arms then my torso in place. I tried to push against the straps to no avail.

“Is he normally like this” Kim asked.

“Sometimes. But the second you put anything inside him he turns nice and submissive”

“I have just the thing”

Kim left to another room leaving Amy to finish strapping me in. Once my legs where held in place she moved to attach a strap around my neck. My eyes caught hers but there pleading was only met with a gentle smile.

“I found it” Kim returned, her hands rubbing lube onto the biggest vibrator I had ever seen.

It was far bigger than anything Amy had used on me. I found myself pre-emptively shuddering. The area around my pelvis was lifted so Amy could slide it under my underwear and inside me. I gasped as it pushed deeper and tighter then anything had before. Then, they pulled the last strap around my pelvis tight. I released a moan as they caused it to shift around inside me.

“You really are a sensitive boy, it isn’t even on yet” Kim teased.

Then she pressed something and the vibrator started to pulse. Each pulse made me release a soft moaning noise only interrupted by my heavy panting.

“Why don’t you start preparing the bleach. I’ll get this thing gagged.” Kim leaned over me, allot of her weight pressing onto my chest.

“Ok” I could barely register Amy’s reply as my eyes rolled back.

I felt Kim brush something over my face. It was silky and individual strands spread out as it slivered over my face.

“Do you recognise this? It was your girlfriends years ago, until one ill thought out bet and suddenly 12 inches of her beautiful hair was now mine. I think maybe you should have it now”

Her hand tilted my mouth open allowing her to feed in the long black ponytail. I felt the silky strands run against the back of and then down my throat. I could feel its smoothness run all the way to the base of my tongue. Where the end of the ponytail had been tied in a cut zip tie she dropped in my mouth leaving it to just fall out ever so slightly. A smug smile spread over her face as she pressed on the remote.

The vibrations gained intensity and felt more forceful. They started to laugh seeing me trying to thrash around only to be unable to move the slightest muscle. Amy had a bowl of something she mixed around with a brush. My head went light. Thoughts unable to form under the force of the vibrator.

Amy removed my ‘man’ bun then started to paste something sticky over individual strands of my hair. She used some kind of foil to keep the strands separated. To my relief Kim turned the vibrator down slightly allowing me to think. She had what looked like a plastic gun in her hand only the end resembled a clamp.

“What are we doing about piercings” Kim asked.

I screeched and screamed but the only noise to leave my mouth was muffled.

“Nock yourself out” Amy instructed.

My head pushed against the straps recoiling away as she approached the side of my head. It was too no avail, Kim grabbed my left ear and placed the piercing gun to its lobe. A stabbing pain cut into me. I would of screamed expect for the hair down my throat. She inserted an earing it was heavy and I could tell it was on a chain. She walked around and did the same to the other ear.

“Some studs as well” Kim suggested and Amy made an approving noise.

She had finished with my hair by this point and watched approvingly as Kim stabbed three holes into the back of my ears. These where filled with studs making my ears feel slowly heavier.

“What about the top?”

“A bar here perhaps” Amy poked at the top of my ear.

Two further sharp stabs as Kim pierced then inserted a bar between two holes in my upper ear. She did the same on the other side.

“And the nose?”

My eyes pleaded with Amy to stop.

“Something small”

Kim placed the piercing gun to my left nostril. She pierced into before attaching a small nose stud. By now tears where forming in my eyes. The pain of the piercings matched by the burning sensation of bleach and the painful vibrator inside me.

“Your being such a good boy” Amy rewarded me with a peck on my forehead.

“Mind if I have some fun while we wait for the bleach to do it’s thing” Kim asked.

“He’s all yours” Amy had a smile on her face “I might just do his nails while you’re at it”

Kim picked up a large pair of fabric scissors and started to cut down from my below collar. Slicing through my t-shirt until she was able to pull it off without unstrapping me.

“That’s a nice surprise, yours I presume” she poked at Amy’s bra that I was wearing.

“Yes, but he’s not supposed to wear it without asking. Remind me to punish him later”

Kim now started to cut of my jeans revealing the pair of Amy’s underwear that I was wearing. She pulled of the jeans leaving me naked except for the collar and Amy’s underwear. I thought that was it when she put the scissors down until pulled my panties down revealing my erect cock.

“Aww it’s so cute I’ve never seen one this small before”

I felt humiliated until she pressed on the remote again and I could feel nothing other than the vibrator. Kim picked up a second ponytail. I had realised that the hair in my mouth wasn’t as thick as Amy’s. They must have cut it in two ponytails.

With two bobby pins she finished wrapping the ponytail around my shaft. Then she placed a clawclip around it, it’s claws digging into and pressing on the shaft. She ran the hair up and down my shaft jerking me of to the rhythm of the vibrator. Once she sensed I was about to cum, she removed the hair and the clawclip taking the payload in her mouth and swallowing quickly. She gave my penis a demeaning pat on its head. Then she put the ponytail and clawclip back around it and pulled up Amy’s panties to cover it. While this was going on Amy had painted my nails a pastel pink colour and applied long fake eyelashes to me.

“What was the hair inspo”

“I was thinking Sabrina Carpenter only longer”

“Well you’ve definitely got the colour”

They washed the bleach out of my hair and applied dye and toner. I caught a glimpse of a hair as it fell over my eyes. It was blonde. Like blonde blonde, not dirty blonde or coppery blonde but a vibrant yellow gold colour. The hair that had been brown all my life now just wasn’t.

“Did the extensions arrive?” Amy asked. She was excited in a way I would normally call cute.

“Did they arrive?” I could hear the eye roll in Kim’s voice.

She retrieved something from a box by the door. I could see her raise her hand and something long trail behind it. At first it looked like a yellowy gold ribbon until I noticed it was formed of tiny stands. It was hair, over a metre long strand of hair attached at the top somehow.

“This must have cost a fortune” Kim’s voice shot across the room.

“Yes, but I figured he deserved the best”

“Why’s there so much of it though. I swear there isn’t normally this many strands”

“I wanted it to be very thick. Figured it’ll look better that way.”

“Won’t that make him really hot. And be harder to look after”

“Probably, but I’m sure he can manage”

Kim brought the box to behind me, where I couldn’t see. I felt the two girls picking at small sections of my hair. They pulled them tight until they were painful then did something to them before dropping them back. As they finished my hair felt heavier then before.

“Nearly done now” Amy planted a kiss on my cheek before returning to the extensions.

Where they had started on the left they now approached the right side of my head. I could feel my head becoming uncomfortably heavy. Once they seemed to finish at the right, I could feel something move from side to side underneath my head.

“I think we need him up for this last part”

Much to my relief the girls started to take off the restraints. I could finally move again and I sat my body upright. As I did I felt something run up against my shoulders and down my back. I realised it was the extensions, where my hair barely tickled my shoulders it now spilled over them and all the way down. My bangs fell into my face, they weren’t longer but they were a yellowy gold colour.

“These just need a little shaping”

Amy brushed my bangs to the side and cut them. She was gently cutting into the hair until it resembled the ‘fluffy curtain bangs’ she was after. They pulled me up only for my legs to collapse under me. I couldn’t feel my whole lower body around where the vibrator was pulsing.

“Come on”

The girls took my weight as they lifted me to my feet. I slowly began to regain control of my stiff legs. As I stood straight I could sense a smooth sliver of hair sliding over my shoulders down my back until the ends tickling my lower thighs. They turned me to face a mirror, revealing the silhouette of a woman.

By now I was use to being made to look like a girl. But this was the girliest I’d ever looked. My skin was hairless and in much better condition than before I met Amy. Her underwear seemed natural rather then like I was cross dressing, except for the claw clip shaped bulge. My face had become more feminine from the skincare and eyebrow shaping Amy would do. The subtle makeup only layered upon the femininity.

But what I, and anyone who would see me, noticed first was my hair. Around my face and shoulders it resembled the ‘Sabrina Carpenter’ cut they where going for but the ends stretch a foot past my my butt. You couldn’t tell by looking at it that it was unnatural, it all flowed around me as if it had for years. Somehow making me look even smaller.

The two girls stood ever side of me admiring there work. Both of them taller then me and I sort of shrunk in there presence. Kim lifted my chin and pulled Amy’s ponytail from where it had gagged me.

“Are you thinking what I am”

“Definitely” Amy replied.

Before I could get a word out Kim’s hand was in my throat pulling out my tongue. By the time I realised what was happening, it was too late. A sharp pain filled me as the needle gun ripped a hole though my tongue. It was quickly filled by a large metal tongue stud. The metal felt strange rubbing against the inside of my mouth.

“Wwhhaaat…” my tongue began to swell. Slurring my speech.

“Shhhh, don’t talk unless we ask ok” Kim chastised me. She gathered my hair together. “What do you think Amy”

“Well it’s something I can tug on while I’m railing him” Amy gave the high ponytail Kim had just tied a playful pull. “That was the main goal. But also he can’t just dress as a guy anymore. Even without makeup, everyone can see your my good little girl now.”

I squirmed a little bit. Her pulling my hair reflective made my ass cheeks clench. It must have been foreseeing it’s future.

Kim pressed a button that caused a pleasant surprise to pound into my hole. I ducked my head and kept my mouth shut. My body seemed to know it’s place underneath these two beautiful woman. More and more my mind seemed to learn that place. The collar around my neck felt as if it was growing tighter. It’s faux leather chocking any hints of remaining resistance.

The slightest wimper left my lips. I worried the girls would realise what was going on in my head. And to my horror they did.

“He’s awfully submissive”

I yelped when Kim pulled my ponytail to make me face the mirror. The woman who stared back at me whimpered. My mind still not processing that she was me.

“Yes, he’s so cute this way” Amy carefully caressed every part of me she knew to be sensitive.

“I don’t know why you don’t keep him like this all the time”

“I don’t either. His personality wasn’t that annoying at first but he’s so bratty and never has anything interesting or funny to say.”

“He didn’t seem the type anyone normal would go for. If I where you I’d just keep him around as a dress up doll slash sex toy. And try to find someone more manly for an actual boyfriend.”

“I was thinking something similar a couple days ago but do think it’ll be funny to keep him around as a muse. Also if you want to borrow him as a dress up doll or for sex he doesn’t do anything important so you can have him anytime”

“Thanks Amy. Would you mind if I let some of my other friends have a go on him as well”

“Guys or girls”

“Both. Is that fine?”

“Yeah that’s fine as long as they clean him. I don’t want him coming back covered in cum”

“Well they’re probably going to want blow jobs so he can just swallow it and clean his teeth later. If not I can just lick it off for you”

“That sounds good. I bet he would love having some cum in that mouth of yours wouldn’t you”

My tongue had stopped swelling so I could have talked if I wanted too. But I didn’t. My eyes looked down at Amy’s feet. I realised something then, this humiliation felt right. Every time Amy had dressed me as a woman I had told myself it was for her. But it wasn’t, it was for me. I actually liked this.

“My only worry is if this brat ends up forgetting who he belongs too”

“I think perhaps that’s something we can fix downstairs” Kim gave Amy a knowing look. Or atleast a look they knew. All I knew was it caused dread to grow deep in my stomach. “Come on, downstairs”

Wait downstairs. Like with people, and me looking like this. The hair. Or the fact I was wearing nothing but a collar, leash and Amy’s underwear. I looked at Amy, her eyes locked into mine, and they pleaded one last time.

“Oh sweetie. You look so adorable when you’re desperate” Amy stroked her hand over my face, mimicking the motion of tucking hair behind my ear. I hoped for a second that she might let me go. “But you must learn your place. When someone tells you to go downstairs. You obey.”

I felt a hard yank on my leash. It turns out I was going downstairs whether or not I wanted to. As we stepped outside into the tattoo parlour, I felt every eye on me. I wondered what they thought. If they even realised I was a man. Because there hadn’t been a hint of femininity in that reflection in the mirror. The only things that could give me away are the bulge in my pants or the flatness of my chest.

They dragged me over to a seat by the window. Of course it was by the window, right where everyone passing by could see. They would glance as they passed but some took out their phones to take photos. I felt myself shrinking into myself. My body reclined into the seat hoping it would melt me away.

“I doubt I need to tie you down. But I will anyway. I like to see you in chains and in truth I think you like not having the option to leave. Even if you wanted to.”

I simply looked up at my girlfriend as she seemingly pulled maniculs form nowhere and locked me in place. And I let her. Every thought in my mind was about why I didn’t stop her, why I was allowing this to happen. But my body seemingly knew it’s place.

“Good girl. Good, Vanessa. Did I tell you that’s going to be your knew name. Vanessa. My good little Vanessa. Such a pretty name.”

I felt the last manicul snap shut. My leg tried to move but the cold metal didn’t even budge. It felt restrictive and comforting in a strange way.

“I think this could remind him who he belongs to” I turned my head as much as I could. Out of the corner of my eye I caught a glimpse of Kim standing tall with what looked like a tattoo gun in her hand.

My eyes grew wide seeing the needle. But I didn’t resist as my head was pushed to the side. I felt my ear being pinned forward and a stencil being printed on the side of my head. Then the stinging as the needle carved into my virgin flesh. It hurt, but not as much as I expected.

Before I knew it, the needle was gone. Amy snapped a photo and brought it around for me to see. It was her name. Written in a stylised cursive font was a single word. Amy, no Amy’s, written into my skin, permanently.

“Do you like it?” I couldn’t tell if she was being serious or not.

“Oh he loves it” Kim hadn’t put down the needle. “But I think we still need something else. Back here.” She poked my nape with one of her sharp, claw like, nails “only he can see, personal sure. But don’t you want everyone to know who she belongs too”

She?

“Isn’t that what this is for?” Amy touched the collar.

“Yes, but that can always been taken off” Kim pulled off the collar. Leaving my neck exposed. “Don’t you want something more permanent, a nice little mark everyone can see.”

“Little?”

“Maybe more than a little”

“What do think Vanessa”

I didn’t respond at first. I didn’t think she was talking with me.

“Doesn’t that answer your question.” Kim chimed in before I could answer.

“Perhaps” Amy grabbed my chin and so she could look into my eyes. I mummered and sighed and hated how pathetic I was being. She stared me down until I had to begin avoiding her glance. “Yes, go ahead” she didn’t have full confidence in her voice.

But it was still enough for Kim. “I’m going to enjoy this” my eyes grew wide, jaw agape. Only for a ball gag to be forced into my mouth.

She called over a few of the other artists. Each with a tattoo gun in hand.

“Try not to squirm”

 

“He’s taking it so well” one of them said, as she was finishing drawing a butterfly on my right ass cheek.

I moaned against the gag stuffed in my mouth.

“Doesn’t he just” Kim was finishing a blackbird on my opposite shoulder.

I felt the third tattoo artists claws scrape down my skinless thighs. Choosing one of the still untainted spot left on my skin.

There needles had carved over my body. Each marking my skin with individual artworks. Each distinctly feminine. I could imagine the stories about each of them a white girl might tell me when I talked to them at a bar. Not that I thought I would be talking to girls like that in any bar anytime soon.

But what story did I have to tell. More importantly what stories would I tell people. The hair the tattoos, what would my friends think, what would my family think. I didn’t even know what to think myself and yet all this was just too much.

Not long after they seemed to finish. My newest tattoos were covered by a thin plastic wrap. It felt like most my body was covered with that same wrap by this point. They rolled me back onto my back. Much of my still wounded skin burning at the movement.

“I know you weren’t sure yesterday but I really think it would complete the transformation. She would be completely unrecognisable.”

The question was addressed to Amy, as I had expected. But I would have struggled to answer either way. Not just because of the gag in my mouth. The fact Kim’s needle was just over an inch from my face caused my eyes to grow wide.

“I’m sure it would. But isn’t that a bit too far.” Amy stroked a blonde hair off my face.

“We’ve gone this far, surely a few freckles won’t be too much. She can always wear makeup over them”

“I don’t know. What do you think Vanessa” she finally removed the gag and started to stroke my face and head with uncharacteristic tenderness. “Do you want freckles?”

I don’t know why I didn’t run. Not now or anytime since the first day we met. But I was tired. Tired of everything. I didn’t want to fight anymore, didn’t want to pretend to be a fighter. Amy cupped my face in her hand and I felt words slip out my studded tongue. “If you want me too”

She looked at me like I was nothing. Not like dirt, with discussed. More like I was a pet she felt guilt bound to treat with kindness. Both of them did. I liked that idea, being a pet of these women. Having them stroke my hair as I lay on there lap. Or tighten my collar when I misbehaved. I was too tired to hide that fact, even from myself.

“She would suit freckles” Kim chimed in. She had been brash before but wasn’t now. We both knew what Amy was just realising. How powerless I was. How she was now responsible for me.

Amy thought for long moments. The gravity seemed to finally hit her. “Ok” she had been trying so hard to break me. I don’t think she knew what to do once I had cracked.

Kim took my head from Amy’s hand and layed me flat against the head rest. My long hair blonde hair spoiled out beneath my head.

“Close your eyes sweetie” Kim said and I did.

“Good girl” she purred. I smiled

“Now don’t move an inch. One wrong move and my needle might slip. Instead of cute little freckles I’ll be drawing a penis on your gorgeous cheeks.” I felt a moan escaped me.

Kim waited for it to pass. Once I was ready her needle poked at my skin. Over the rim of my nose and onto my cheeks. The pain didn’t hurt and I was calm. Every worry had seemed to leave me, I didn’t miss them.

It was done quicker than I hoped. Cute little freckles now formed an upside down v on my face. They cross the rim of my nose then plunged under my eyes. Framing my eyes just right.

I was unrecognisable. Completely and utterly so.

 

Amy didn’t talk much. When we got back into my car. Although this time I was the passenger. Partly as a sub dom thing, but me driving with this many endorphins was not a good idea.

Kim had talked allot. About how cute I was. I looked up at the mirror in the passenger seat. And agreed with her.

The feathery blonde bangs across my forehead. The art that adorned my skin. Kim had done my makeup before I left and I looked super human. Like a painting, a great masterpiece, that’s how I felt.

Kim had given me some clothes to wear. Not that they were really clothes. That implemented the covered anything. The jean shorts where so short you could see and so tight it felt like I was being pegged again. The only reason you couldn’t see my penis through the blue demin was that it couldn’t get any circulation.

The top was no better. It wasn’t a bikini. You couldn’t tell it wasn’t a bikini but it wasn’t one. The black fabric left nothing to the imagination. Each inch of hairless skin was exposed. Each tattoo displayed on a gallery of… me.

My only protection was the long blonde hair that cascaded over me. It hid the tattooed collar around my neck as well as my shoulders and back running down to my… shit. I realised I know had to worry about sitting on my hair after adjusting myself in the car seat.

“We are going to get food” it wasn’t a question.

Good I’m ravaged. My eyes looked in the mirror at Amy. Will be.

We pulled into the parking lot of a fast food place.

“Turn around” Amy commanded. I wasn’t sure why she wanted me to but I obeyed. “I want people to really see you.”

Her hand began to stroke through my hair. Don’t let the word stroke fool you into thinking she was gentle. I felt the long blonde locks being pulled tight. Painful tight, I groaned in pain but that only invited her to pull tighter. She tied it all into a tight high ponytail, careful to not let any tension escape. I couldn’t think over the tension pulling at my skull.

“Come on” she got up and I followed after her. My scalp burned from the tension. An unfamiliar weight swung behind me as we walked. My hair reaching down to my thighs even up.

Every eye was on me. I don’t know why I didn’t feel this… what did I feel. Embarrassed? Was that it. Why was my cock trying to grow against my jean shorts. Why did my cheeks blush under my makeup. The feeling of my ponytail felt, right? It was heavy and as I moved my head it dragged on my scalp but for some reason I didn’t mind the pain. We passed windows and I caught a hint of my reflection, hair as thick as my thighs cascading down my toned and exposed back. I felt warm. In, what I was realising was just, a bikini top and jean shorts I felt warm. I suppose the heat must have been coming from the inside.

“Your going to need to practise a new voice” Amy told me when we sat down. She was right. I couldn’t just go around looking like this and speaking with my old voice. Not if I didn’t want to give cashiers heart attacks.

“Aww don’t act so soppy” she watched me pawing at the chicken salad she had ordered me while tucking into her burger. “What do you think.” Her posture adjusted itself to point out a guy watching us. “I bet you like the attention”

The noise that left my mouth resembled no but the wine wasn’t quite distinguishable as such.

“Poor thing. But what do you think, I could invite over. You have an amazing mouth it would be a shame, wasted, on, only, my, lips” she smiled again.

I made the same pathetic moan and tried to distract myself with the ‘wonderful’ salad infront of me.

“How many of your old fratboy friends would want to be friends with now Vanessa. I suppose all of them” her voice felt light as she giggled. “Though friends might not be the right word.”

In my reflection I knew the answer. All of them.

“Maybe I need to make some phone calls. Silicone is nice and all, but it has nothing on the real thing.”

 

By the time we where back in the car I was numb to her words. Not numb like with pain or  white noise. Numb as in her teasing didn’t bite anymore. Something in me just began accepting all she said as true.

Amy took another turn. I didn’t recognise where we where heading, into town and the posh part of town at that. The buildings got taller and older, the little greasy spoon cafés turned to hipster coffee places, then restaurants who would have charged more than I had in my bank account for a glass of wine.

Amy pulled up outside what looked like a hotel. But as I looked closer I realised it wasn’t that, but an apartment block. She got out the car without a word, and I found myself chasing after her. The keys to my car where handed to a chaperone. He seemed all to happy to rush my car to a parking lot far from the sight of the distinguished patrons of, whether we are.

“Welcome back ma’am” A doormen waved us through into the lobby that screamed sophistication.

I continued to follow my girlfriend deeper into this monolith of a building. Eyes wondering across the georgian flourishes and the neo-gothic arches. We passed the lobby and entered one of the lifts. Amy asked for the penthouse. The smartly dressed young man pressed the button while Amy admired the perfectly ironed lines of his waistcoat and uniform.

“… Amy?” I didn’t want to talk with the man with us, but I worried I wasn’t going to get a better chance.

“Yes, dear”

“Where are we going?”

“To our apartment sweetie.” She stared me down through the elevators mirror. “Did you think I was going to make my sugar baby pay for her own place. Or did you think I was going to let reduce myself to living in some squalid let just to be with her” the disgust in her voice hurt.

“The penthouse ladies”

Ladies

I followed Amy wanting to say something but there was nothing for me to say. She unlocked the door and guided me into my new home. Light flooded the huge space. But I wasn’t given time to admire her, our, apartment. Amy wanted to show me something, and dragged me by my wrist to the farthest, most hidden, edge of the large penthouse apartment.

“Your room” Vanessa was written over the door.

It was dark. Intentionally so, I couldn’t get a good look inside until the harsh clinical light was switched on. The walls where painted a militant grey. My eyes grew as I saw what she had put inside this room.

There was the normal things you might expect, a bed that didn’t look at all comfortable tucked into a corner and a vanity stocked with makeup and hairstyling tools I didn’t recognise. But most the room was filled with a variety of contraptions more suited to a medieval dungeon then a bedroom.

Four pairs of cuffs attached to a metal array against one wall. A chair not dissimilar to the one my hair had been dyed in was fitted with straps. What looked to me like a gymnastics pommel horse was in the middle of the room, cuffs around it attached to chains.

“I’m going to be back in a minute. Get yourself ready sweatpea”

Just like that she was gone. The door behind her slamming shut. Get myself ready. That could only mean one thing. My ass quivered in anticipation.

I looked around but stopped myself. I didn’t know what so much of the equipment did. Those that I knew scared me. Especially the locked metal cupboards whose rattle let me know they where full. So I sat myself at the vanity and just stared at my reflection.

My bangs fluttering over my forehead. My freckles and my tattoos. The way my smooth hairless skin looked in the light. My high ponytail.

I pulled the hair out of its tie. The instant relief of taut hairs releasing made me numb. I basked in that feeling and my reflection until something tapped on the door.

Amy crept inside. Her toned body framed in a tight black leather catsuit. Six inch heals rat-a-tap-tapped on the hard wood floors. She had a cane in her hand.

I tried to turn but her sharp fingernails appeared like pins on either side of my rapidly growing eyes. She made my face keep still staring down my reflection. I looked down as long blonde hair slipped over my shoulders.

She pulled a piece of fabric from somewhere and pulled it over my eyes so not a slightest light could enter. Her fingers scratched the back of my head while tieing the blindfold.

Next I was womanhandled out of the chair into the centre of the room. My mind tried to ordinate itself. The pommel horse? I was lifted onto it and moved to lay, face first, on it’s back.

Those sharp nails and cold fingers wiggled off my socks then my jean shorts, and panties. Her hand stroked down my lower back. Over my vulnerable butt crack to my thigh, down beyond to my calf and along the sole of my foot. Leaving icy tremors in it’s wake.

She locks my ankles in solid steal cuffs then returned to my upper half. The black bikini top and my (her) bra was thrown to the ground. As I suspect was the last foot of my hair that was brushed over my shoulder. My wrist where cuffed ever side of the horse.

“Awwh” I moaned in pain as she pressed something. The cuffs where pulled tight until my limps felt like where about to snap. At the same time the pommel horse was tilted so my arse pointed to the sky.

“Did I say you could moan Vanessa”

Something was shoved into my mouth. It was massive, round and felt like silicone. My jaw was split open while it pushed deeper. The sides of my mouth ached and my teeth where forced into the gag. Droll was already building up and leaking from my mouth. Amy tied it behind my head as I tied to moan and groan and struggle. Nothing helped.

“Still resisting” she smiled. Her hand stroked over my ass. Each touch eased my sensitive skin.

Crack.

Her paddle smacked down hard into my arse cheek.

I moaned in pain but only a gurgled noise escape the gag.

Crack.

I moaned harder.

Crack.

Again.

Crack. 

Her paddle slammed again and again.

Crack.

The pain radiated from my bright red cheeks.

Crack.

 

Crack.

 

 

Only once I was spent was she satisfied. But even after that her paddle bruised my arse half a dozen more times.

I don’t know what sounds I was making now. My throat felt scared from moaning against the gag. Tears wet the inside of my blindfold.

Her hand touched my nape again. The pommel horse moved again. Readjusting to a new posture.

“I brought this specially for you” She whispered and I tried to clench myself in preparation.

Her heels made a sound as she flicked them to the side. Then I felt it, her mounting behind me.

Her hands grabbed my arse cheeks and pulled apart. The fresh brushes roared in pain from the touch.

“Arggghhhhhhh…”

I screamed as she began her first thrust into me. The rock hard strap on was larger and thicker than anything I could have ever managed.

I tried to roar in pain as she forced herself deeper into me. Only once she had pushed as far as she could did her hips began to thrust. Hard silicone rammed against my prostate.

“Arrrgghh” my attempts to moan grew loader and loader. But with each moan Amy began to thrust with more and more force.

Her ruthlessness cracking into me as she thrusted against every sensitive spot inside me.

Thrust. Unswallowable saliva made me choke against the gag.

Thrust. Tears escaped my blindfold to mix with the coat of sweat trickling off my face.

Thrust. My penis erupted against the pommel horse. Warm seaman stuck my chest and cock to the fabric horse.

Amy continued to thrust and thrust. It felt like it went on for a lifetime. Only because a different person lay there. Once it was all over.

 

An hour later? Who even knew. Once Amy had taken all she wanted she lay on me.

Pointed nipples scratched me back through the catsuit. Gentle fingers reached up to remove the gag from my mouth. I tried my best to swallow the masses of droll inside me.

“Vanessa” her voice was softer then she deserved.

I gulped up another mouthful of saliva. “Yes mistress”

“Clean up this mess”

“Yes mistress”

 

To be continued…