Urban

Androgynous Boyfriend - Part 3

Added 2023-05-03 14:08:46 +0000 UTC

"We've just been invited to Gaston Maraposia's Halloween party," Max said smiling at me from under the pink wig she'd taken accustomed to wearing while we were home alone.

"Is that a big deal?" I asked.

"Is that a big deal? Sometimes I forget you've only been at this for a few weeks." She winked. "Yes, it's a very big deal."

"Ah, some big mucky muck, could help build your career?"

"Not just that, geez, Maraposia's a hero of mine, well back when I was thinking of going into fashion."

"What's the party like?"

"It's a who's who of style, but it's also a costume party. "

"Like Halloween costumes?" I asked.

"His parties tend to be a little stuck up and snobbish, except for the

Halloween one, where all the stuck-up snobs get a little freaky."

"Whips and chains freaky?"

"I don't know about whips and chains, but there will be a lot of naked people there. Well naked costumes"

"How can someone be naked in a costume?"

"One year he had topless mermaids in his pool, so I hear."

"That's going to be hard to top."

"They were paid, not guests. I think it would be in bad taste if a

guest tried to use the pool, but I don't know, not really."

"So what are we going to go as?"

"I don't know, I thought maybe we could take our personalities up a notch. Do you have any ideas?"

"You mean like more androgynous or more pompous?"

"Actually maybe a little less androgynous." Maxine had a wicked look in her eye.

"Oh I get it, you want to make me your bitch don't you?" I joked rolling my eyes.

"I wouldn't have put it that way, John. More like I want you to be my special lady." she leaned over from the chair resting her chin on her hand, and gazed into my eyes. "Come on, it's just for one night. It should satisfy my curiosity. It's not like anyone will take it too seriously, it's Halloween after all."

I sat and thought for a minute until I found myself gazing out the window. "Oh well, I don't suppose it would kill me. But if this somehow hurts the business, it's on you."

A few days before the party we were back at the stylist's with Leslie.

"This time we want to go all out, turn him into her."

"How far should we go?" asked the stylist.

"Well it's just for a party, but if we had time for a sex change we'd be on a plane to Thailand," Leslie laughed and winked at me in the mirror.

"Well in that case why don't we start with laser?" asked the stylist.

"How permanent is that?" I gulped "Oh don't be a baby," said Max. "It'll grow back eventually, the first

few times" I spent the next hour and a half getting zapped until my skin, my face, and my chest was as smooth as a baby's.

Max continued, "I thought it might be fun to feminize your hands while we're at it. I don't think you ever got to try living with long nails before. I tried it once, it drove me nuts. But some girls like it."

The stylist cleaned up my nails and used some very serious glue to attach long false nails that stuck out over the edge of my fingers by about half an inch. She coated them in bright red, then brushed on a clear coat and a top coat. She continued onto my toenails as another stylist started on my hair.

They bleached it a much lighter platinum blonde. The girl snipped at my hair while it was still wet, so I couldn't see the full effect, and set my hair in curlers.

Max came over and started rubbing my neck, "I know the party is still a few days away, but I want to get your makeup done anyway, so we can see if it's going to turn out."

The stylist dipped a sponge in some foundation and started on my face. The eye makeup seemed like it took forever, Leslie ordered them to give me Doe's eyes, with strong dark liner. All the while Max looked on, enthralled; I thought she was going to lose it when they attached the fake eyelashes.

I heard Max whisper to Leslie, "I want her to have naughty lips."

Leslie gulped and smiled first at her, then at me. The lipstick came in three layers. The bottom was done entirely with a red pencil, first, my lips were outlined, just a touch beyond their natural borders with a gently arching cupid's bow across the top, then they filled them in entirely with the bright red of the pencil.

The second layer was done with a richer, darker, smudge-proof red. And finally a coat of candy apple red gloss.

I hadn't even noticed that my hair had set. When they released it from the curlers, it cascaded in spirals down either side of my face.

Looking at myself in the mirror was embarrassing, not only did I see a

the woman staring back at me, but a sultry sexpot.

"How do you like your lady self?" Max whispered into my ear.

"Are we done then?"

"Not by a longshot."

"Oh boy." I gulped.

"Oh, girl." Max laughed. "Besides I know you like it." And when the

stylist turned around Max brushed the tip of my now erect penis through my pants.

The next step was to pierce my ears, with a little diamond stud on each side.

"Okay, I'm going to take her to get dressed now," Max announced and walked me into a private dressing room.

"Here you go sport." As Max handed me a wisp of lace, I realized she was using her regular voice again.

"What is it?"

"It's a garter. You clasp it around your waist."

I was having a little trouble with it. "Man, these nails, are really awkward. Maybe we should have waited until the night of the party."

"Yeah, but they look so damn sexy, and at least I'm not the one who has to put up with them. Here I'll help you," Max said with a snarky smile,

pulled down my pants, underwear, and all, and clasped the black garter

around my waist. She removed my shirt, so I was just standing there in

the garter, still erect and at attention.

"Sit down and give me your legs," she instructed, before touching my candy-red toes with the lacy edge of a black stocking. She rolled it up slowly, stopping to look me in the eye from time to time. Then picked at it until the back seam was straight, before pulling up the other. She tightened the garter, and attached each of the straps, pulling them tightly so that I felt each snap against my skin.

"What's that?" I asked as she pulled out an even more serious-looking undergarment.

"Oh this, this is just a corset. You don't really need one, with your waist so small, but I thought it might be fun just the same," she said before pulling it up my legs, and over my torso so that it settled on my new, somewhat higher waistline.

"Breathe out for a second, Honey."

"Why?"

"Oh don't be a baby just breathe out." She pulled my shoulders back and gently pressed against my tummy until I started to exhale. She kept me exhaling for a lot longer than I expected until I was entirely out of breath. All at once, she strained pulling the laces of the corset as tight as possible. I gasped for air but was only able to take in a short breath, as she tied it off.

She slapped my bottom. "Good girl. Sorry about that, but hey check it out," she said pointing to a mirror. My waist had taken on a distinct hourglass shape.

"Yeah, it's nice," I wheezed.

"Just take more breaths. But stay calm, and don't overexert yourself. You'll get used to it. Come on now we're almost done," she said, as she clasped a black padded bra around what was left of my chest. "I didn't want to go with breast forms, we're going for more of a supermodel look, and they don't have big boobs anyway. Just enough padding so it'll hold its shape."

She sat me down again and slid a lacy pair of panties up my legs. "This isn't going to work," she said when she reached my penis, "And you act like you're not enjoying yourself," she said stroking the tip. "But let's save the fireworks, for when we get home hunh?" she ran out and got a cup of ice, and held it against my unit until it went down. I was surprised that it did, and she tucked it between my legs and fitted the panties into place.

"Those are really tight," I protested.

"They're supposed to be. They're what's called a gaff. Plus it'll be a good test run to see how well they work under pressure."

I felt my member trying to get hard again, and it did, a little, but the gaff limited it.

"Ta-da," she said with a smile holding up a red swing dress, covered with black lace.

I stepped into the dress, and Max slid it up my body. She pulled my arms through two cap sleeves and started zipping me up the back.

Then she slid my feet into a pair of black 3-inch heels, with a little red bow sitting just above each open toe.

I stood up and almost fell over myself. "I've never worn such high heels before. I don't know if I can manage it."

"Don't worry," she said, lightly touching my nose and switching back to the accent, "See it's a good thing we got started a few days earlier." she helped steady me, as I stepped out to show the others.

Maxine couldn't get me back to the loft quickly enough. But oddly enough once she did, she just stood there staring at me.

"Want to go back to the, umm bedroom," I asked.

"Yes," she said licking her lips, "But if we do, it'll be over too quickly. I want to savor this."

"I don't think this ever came up before, but you like girls don't you?"

"Maybe, but that's not it, I just like seeing you like this."

"Like a girl?"

"Like a sex toy," she said smiling and arching a brow. "Don't get me wrong if you really didn't like it, I don't think I would either. What do you think of yourself?"

"The nails are a pain," I said stretching out my fingers in front of me, "But they do look nice. And the rest of it too." I stood in front of the mirror and looked myself over. "And I'd be lying if I said I didn't enjoy having you do those things to me."

"You enjoyed the attention?"

"It's kind of interesting. I feel helpless and powerful all at the same time."

"It's a trip to see you that way. Makes me want to do all sorts of nasty things to you."

"Like what?" I asked with some apprehension.

"I almost don't want to say. But I suspect you'd enjoy it."

"Enjoy what?"

"Okay," she sat me down on the couch where I could see myself in the mirror. And then went to get a box from the bedroom. "A lot of girls like the thrill of being helpless," she said as she unzipped my dress and pulled it off over my head. "I suppose it's a biological thing, to make sex with forceful men more exciting. But you don't really need the guy."

She pulled out a pair of black leather cuffs and took one of my hands gently in hers. "Shall I continue? Just to see if you like it."

"Okay," I nodded. She latched the cuffs around each wrist pulled my arms behind me and locked them into place.

"Do you trust me?" she asked looking me dead in the eye.

"Yes."

She brushed a rubber ball against my lips. "Open up," she said. And when I did, she pressed it into my mouth and locked a harness around my head.

"It's less complicated if you can't talk. You don't feel the need to protest what we both know you're going to enjoy."

She buckled a pair of matching black leather cuffs around my ankles and latched them with a small brass lock. "Don't forget to look in the mirror, that's half the fun."

I looked at myself and saw a blond bimbo, helpless and gagged.

"I've only tried this stuff out on myself before. I've always been a little embarrassed about liking this sort of thing, but I thought you might enjoy, being my helpless little slut." she started whispering baby talk to me. "Do you like being my slut?"

I nodded with apprehension, unsure of where Max was taking this.

"Oh I know you do." she pulled my legs behind me and locked the two pairs of cuffs together. Then we watched ourselves in the mirror as she stroked my hair. "Bimbo, slut, cunt" she whispered in my ear with affection.

She pulled my panties down to my knees. "What should we do about this?" she licked her forefinger and touched the tip of my penis. "Maybe I should let you suffer for a while first? That would just be cruel." she got up, went into the bedroom, and closed the door. Leaving me to watch myself on the couch. The stylists had made me up to last. My lips hadn't smudged, and my hair was still holding together. I tried struggling against the cuffs just to watch myself.

When Maxine did finally emerge she was wearing a matching red set of lingerie: garters, stockings, bra.

"Ohh, how's my little slut holding up? Does my little whore like wearing pretty clothes? Does she?"

I nodded, hoping to move this along.

"Does she like having pretty hands with pretty nails that make it hard for her to do anything but be my pretty little whore."

I nodded.

"Look at yourself in the mirror, do you see any sort of man there?"

I paused for a second and shook my head.

"Do you want to be my pretty little slut forever, and ever?"

I wasn't sure if she was serious. She lifted up my chin, gazing into my eyes, and asked again, "Do you

want to be my pretty little slut forever, and ever?"

I nodded and she didn't say anything but instead produced a black

laced trim blindfold mask, she pulled it down over my eyes. I felt hands rubbing my thighs. I pulled at my arms and legs and couldn't move them. The weight of a warm body on my chest making it hard for me to breathe, and darkness I couldn't get away from.

"You like that do you?" she asked, as I felt my body shiver. Within seconds I was drenched in a cold sweat.

I tried to tell her something was wrong, that I hadn't felt this helpless since the hospital, but my words came out as smears of lipgloss against a rubber ball.

"Are you" her question trailed off as I bit into the rubber ball. There was shooting pain at the base of my teeth when they sunk in. My penis went flaccid in her hands.

"Fuck, what's wrong?" she asked and yanked off the blindfold. That helped but I was still exhausted, dripping with cold sweat, and unable to move.

Max fumbled with the key, she was shaking, but eventually, I heard a click behind my head, then she pulled the rubber ball free of my teeth.

"Are you okay?" she asked again.

"Sorry," I said tasting blood in my mouth, "it's just it feels a little too much, like back at the hospital."

Max continued to fumble with the locks, tears streaming down her face.

"Oh my God, I'm so sorry."

She released my hands and started working on my feet.

"Don't be. You couldn't know. I didn't know." My voice sounded weak to me. I found myself looking at the bright red nails on my hands and sighed.

She unlocked my feet and helped me sit up on the couch. She placed a blanket over my shoulders, went to the sink, and brought me a glass of water.

I drank it slowly, with her kneeling beside me. Noticed the blood in the water was the same color as the lipstick smudges on the glass, and the same color as the fake plastic nails glued on top of my own.

She looked at me as if to ask what was wrong, but didn't utter a word.

"It's just I kind of feel like a man in lingerie with a bunch of shit glued to me right now."

"Why don't we take some of that stuff off you?"

The stockings drenched with sweat felt like wet tissue paper stuck to my legs. I heard a sticky thwack against the floor when we finally cast them aside.

My whole body relaxed when she loosened the ties on the corset. I kicked it away once it was free of my legs.

She gently touched my face and pulled the false lashes off. When she started pulling my fingers toward the jar of removal gel, I protested, "It's okay they'll look good at the party."

"I don't give a damn about the party," Max said and proceeded to remove each one of the bright red nails.

She wiped my toes clean with acetone and started using cold cream on my face. Finally, she used a wet towel, and a bowl of water to clean my skin.

When she was done, she took everything off of herself: clothes, and makeup, and then settled in beside me on the couch until we were two naked bodies holding each other.

Hours passed as the sun began to go down again. She spoke in a whisper, "I still remember the sting of duct tape pulling against my hair, and the cold wet feeling of him oozing out of me. Sometimes I feel like I'm still trapped on that chair like I'll never get away. That's why I slit my wrists at the hospital, to get away from him, from myself." I wanted to tell her everything would be alright, that he was a corpse decomposing in the ground. But I wasn't sure if I believed that myself, not really. "Do you think you'll ever be alright?" I asked.

"I hope so," she answered.

I kissed her forehead and she laid her face against my chest.

The next day things were, understandably, a lot more relaxed. We tried on our costumes for the party, we were doing a gender-bent mad men, with Max as the male boss, and me as her secretary. We replied with the nail polish, though this time to my own nails. And then spent the rest of the day having sex games. We'd take turns tying each other up, though the blindfold and ball gag went in the trash. At the end of the day when we decided to go out to eat, and I found my regular clothes looked freaky with my new hairstyle, I went in a dress. And although we went to a gay-friendly restaurant, I don't think anyone knew we weren't a lesbian couple.

Max couldn't keep her hands off me during the cab ride to the party. She'd keep picking at my stockings or adjusting my hair. She looked cute herself even with her hair slicked back, a touch of gray makeup on her face to mimic a beard shadow, and her breasts tightly bound with an ace bandage. But her face was too cute and she would have looked like a ridiculous young boy dating a full-grown woman save for the lifts she had in her boots, which allowed her to keep her height advantage over me, at just about 6' compared to my 5' 10" in heels.

Maraposia's house was a few miles outside the city, and we weren't sure we had the right place until we found a line of limos backed up. We felt a little self-conscious stepping out of the cab, but people were too distracted to notice. The doorman was just that. A door with the face of a man, or rather a man with his head poking out of a door, covered in foam latex and paint to make him look like part of the building.

He'd joke with each of the guests before letting them in. He asked Max how "he'd" gotten a date with me, implying that blackmail was somehow involved.

When we finally were let in, we were in for a treat. The doorman was just the beginning. Mariposa had hired actors to portray most of the furniture. A grandfather clock was serving drinks at the bar, and several of the molding angels, the top of the stair rails, were all people, covered in paint, sunk flush with the building's structure. Much of the hanging art was people too. And Max and I would go around criticizing each one. Eventually, she got quite busy meeting people, she was a little more on her game than I was, and I found myself wondering by myself.

I had just stepped out on the balcony and was about to step back inside when I saw a great oaken chair blocking my way, it was upholstered in rich red velvet and had a suspiciously human-looking wooden head atop its high back.

I chuckled to myself and pronounced, "And here I was looking for a place to sit. Only to find a place to sit looking for me."

Though the chair's face remained frozen, I thought I saw a smile from

the corner of his mouth trying to force its way onto his face.

"It's really getting quite chilly out here, I just suppose I'll have to burn the furniture." I jested, pulling a zippo out of my purse, and sparking it near the chair. "You're a man right?" I stopped and asked the chair, to which he stood up, and bending his great wooden arms, took a bow.

"Forgive me if I do offend the lady," the chair asked in a deeply mature voice, "but I might ask the same question of you"

"A man in a dress, you are correct."

"Ha I knew it!" said the chair. "And then I trust no offense was taken."

"None Sir Chair, but I must warn you that unlike yourself," I slapped my own ass, "This seat is taken."

"Personally or professionally?" the chair asked in a truly concerned manner.

"Both, I guess, but more personally than professionally. What business does the chair speak of?"

"Ah good." The chair saw an opening. "Well, not to be too cliché, but has anyone told you, you ought to be a model?"

At last, the lights flickered signaling the night had ended. I hadn't seen much of Max, but she found me to tell me the cab was waiting outside.

She was happily clutching a fistful of business cards. "So how did you enjoy being a woman at the party?" she asked.

"It was a lot of fun. I kept worrying that some dumb guy was going to hit on me, but that never happened."

"Not with this crowd. My dear lady, you might be one of the more manly men here. So can I get you to go in drag again next year?"

"Do you like seeing me this way?" I asked.