Bobbing for Apples
by PVCnLeather
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© Copyright 2013 - PVCnLeather - Used by permission
Storycodes: F/m, halloween; cd; maid; butler; party; bond; rope; bfold; straps; bdsm; hum; sex; climax; reluct; X
Ghoul-gle jpn
Bobbing for Apples PVCnLeather F/m, halloween; cd; maid; butler; party; bond; rope; bfold; straps; bdsm; hum; sex; climax; reluct; X

It was October 31st and I was laying on my bed in my dorm room deciding if I wanted to do anything tonight or stay in and surf the internet. I knew there were a bunch of parties going on at the frat houses and other usual party places but I had never really gotten into Halloween and hadn't put together a costume anyway. I could throw on a pair of jeans and a white T shirt and slick my hair back and go as a 50's greaser but that would be lame. That is all I had. Just then my phone lit up and it was a text from Tisha. A girl I had hooked up with a handful of times this year and was always good for a little fun.

[ Hey you. What are you doing tonight? ]

[ Just deciding. I didn't have any concrete plans. Maybe just hang out here. ]

[ Lame! Come to this party with me. ]

[ Is it a costume party? ]

[ Yes ]

[ No thanks. I don't have a costume ]

[ I have one for you. ]

[ What is it? ]

[ It's a duo thing. We would have to go as a combo. you know, like Salt and Pepper. It's the rules. I'll fill you in when you get here. ]

[ I don't know. I wasn't planning on dressing up. ]

[ C'mon. It will be a blast. We'll hang out, get drunk and I'll let you stay here tonight. ]

[ When is it? ]

[ Hurry. Come now. Don't be a chicken shit! ]

[  you twisted my arm. On my way. ]

I didn't have a car at college. A rule my parents made. But Tisha did. I slipped a jacket on and got on my bike and rode to Tisha's. She was just a couple of blocks off campus in a house she and three other girls rented.

I rang the doorbell and Tisha answered. Well, Tisha in a Butler's costume anyway. She was wearing a black suit with tails, patent shoes, a white mens dress shirt with a black bowtie. Her short black hair that was normally spiky and cute was wet with hair gel and combed over like a business mans. She wore a fake mustache and was carrying a silver tray with two filled shot glasses on it and a bottle of Makers Mark. A bar towel hung over her left forearm.

"Welcome sir Joshua" In her best British accent. "The car will be pulling up shortly so you had better get upstairs and start getting ready. I have prepared your favorite drink for you. Please." As she motioned to the shots.

"Cute Tisha"

I entered grabbing a shot glass and I threw it back.

I followed Tisha upstairs towards her room. We stopped at the top landing and she motioned at the second shot.

"Please Sir. This one is yours as well. You have some catching up to do."

"Are you trying to get me drunk?"


We entered her room and layed out on the bed was what looked familiarly like a maids uniform.

"Clearly you are wearing that and I am changing into your Butlers costume right?"

"Nope. Clearly my costume will not fit you as I am petite and you are not. A chamber maid is the perfect compliment to a butler and I told you we had to go as a combo."

"I am NOT wearing that. There has to be something else we can go as."

"There isn't. C'mon Josh. You promised and I really want to go to this party. The invitation said "Risqué is encouraged and there is nothing risqué about you being the Butler and me being the maid. That would be mundane. I bought the maid stuff in your sizes because I knew you would be a good sport about it. I spent a lot of money on it."

"You should have asked. I am not comfortable with this."

"You should have answered my text last week before I had to make decisions. Besides, when I am done with you, no one will recognize you anyway. If you think they will, we won't go.  No harm no foul. Please Joshy. You don't know any of these friends anyway."

"I don't know Tisha."

"Just humor me to start with at least."

Tisha is up against me at this point pleading for me to say yes. She has a way of using her hands all over your body and placing her mouth just millimeters away from your neck and face as she talks in her sultry voice luring you in.

"Alright., alright. I'll humor you. But I'm not comfortable with it."

"You are such a good friend Josh. You won't regret it. I promise you a big pay off."

"Uh hu."

"First I need you to take a quick shower and shave your legs while you are in there."


"Humor me josh. It's October. You won't be wearing shorts again for five months. Plenty of time for it to grow back. We can't have hairy legs under fishnets."

Reluctantly I moved to the bathroom and did as she asked.

Out of the shower I dried off and put my boxer briefs back on and entered the room. Tisha was on the bed holding somehting black and shiny.

"First the skirt. Here you go" as she tossed it my way.

Catching it I noticed how smooth it felt.

"What is this?"

"PVC. You'll like it. Step into it."

I stepped into the skirt and pulled it up to my waist. It hugged my hips and just barely covered my ass.

"I think it is too small. This isn't going to work."

"No. It's perfect. Don't zip it up. We will do that in a bit. But the only thing not working here is your drawers. They can't show. Pull them off."

"I won't go commando under this."

"You won't have to." as Tisha was digging through her discarded clothes in a basket in the corner.

"Here." As she tossed me a pair of black satin panties.


"Oh you c'mon. It's perfect. Pull the skirt up and slip them on. A little piece of me with you at all times."

Embarrassed, I stepped into the panties and pulled them up. Clearly seeing my junk was not going to fit Tisha told me to pull my cock down and back and tuck it up between my legs. As I did this my nuts descended into my groin. I pulled the panties up tight and they secured my cock and balls into their hidden position.

"Holy shit."

"Funny isn't it. How quickly you lost your manhood."

"Not funny Tisha. I'm doing you the favor here. Be nice."

"You are right. Leave the skirt pulled up I have one more thing first."

Tisha stood and walked over with another PVC item in her hand. She wrapped it around my waist and clipped it in back. "A garter." She said. "To hold your stockings up."

She pulled the skirt back down. You could see the outline of the garter through the skirt.

"OK, stocking time."

One at a time I pulled up a pair of fishnet stocking that had a wide PVC band at the top. Tisha clipped the garter at four places on each stocking. Next Tisha handed me a black matching PVC bra.

"C'mon Tisha. A bra. What do I need that for?"

"To hold your boobies up of course. How do you think we girls keep them floating all the time?"

I noticed that displayed in each of Tisha's hands was a silicone boob. Nipple and all. And they were not small.

"I guessed on the bra size so I hope it fits."

"I don't."

Tisha helped me into the bra and clasped it in back. She moved around to my front and stuffed a silicone boob into each cup shifting them to get the nipples even and just right. They were very defined through the PVC.

Tisha moved back to the bed and grabbed a white satin button up top.

"Put this on."

I pushed my arms through the sleeves and began buttoning from the bottom up. This top was tight too. It hugged my sides and I couldn't quite get the top buttons buttoned.

"Perfect!" exclaimed Tisha. "A little bra and cleavage showing. Tuck your blouse in."

I looked down and saw that I was 'nipping' out through the stretchy white satin and rolled my eyes as I tucked in the top.

"Getting close Joshy. This is going to be so much fun. You look amazing! Just a few more touches."

Tisha moved closer and had what I recognized as a corset in her hands. Black and satin. She stood in front of me and wrapped it around my back and clasped six eye hooks in the front. She pulled the skirt up over the corset and moved around back.

"I am going to tighten this a little but not a lot. You will need to move around a bit for a while."

I felt the corset begin to tighten and squeeze my waist. It got tight on my hips and the bottom of my rib cage. My got just a tad smaller and she stopped.

"That's good for now. And look, no worries, the skirt zips up just fine now. It fits perfect!"

Tisha poured me another shot and hesitantly I threw it back. I was just starting to feel the first two.

"Josh, I need you to bear with me now while I do your nails and make up. It just wont be complete if you go as a dude in a maids uniform. Are you going to be alright with this?

"What choice do I have? We've come this far haven't we?"


Tisha had me sit in a chair while she put fake nails on me and painted them Ferrari red and then began to apply makeup. It felt like it took a long time and it tickled. She applied something to my entire face - Cheeks, nose, chin, forehead. And then spent a lot of time on my eyes and even put on fake eyelashes. She outlined my lips and then graciously applied lipstick over and over. Next she held up a short black wig and pulled it over my hair adjusting and teasing it.

She asked me to stand and she wrapped a white round maids apron around my waist and tied it in back.

"Just need the shoes." She said.

Tisha reached under the bed and pulled out a pair of black heels.

"I hope these fit. I am pretty sure I got your size correct. Slip your foot it."
Tisha guided the first heel onto my foot and I stood down. I recognized that she had to help me with the heels because the rigidity of the corset kept me from bending over. The height of the heel made my other foot stand on it's toes. She slipped the second heel on and pulled the straps up and around my ankle.

"The only pair they had in your size had this locking strap so I hope you don't mind." As I heard the 'snap" of a lock.

"What the hell?"

"Don't worry Josh. I have the key." As she closed the second lock.

"I'm not worried about a key. I'm worried about walking in these things!"

"HeHe. We'll lets practice on your way to the bathroom. I think you are going to be amazed with my work."

I followed, or rather hobbled behind, Tisha to the bathroom.

"Holy Fucking Cow!!" Is that fucking me?!"

"You bet your hot ass it is."

"I can't fucking believe it."

"So you don't recognize yourself?"

"Not a bit. Holy shit. I look like a chick!"

"Good, then we are going. You said..."

"Can't we just stay here and fuck?"

"You are not my type."

"I'd fuck me?"

"Ha ha! C'mon, we have a party to go to."

"Hand me that bottle." I retorted.

We arrived at the party a bit later. I had never been to this house before. Set back off the road in a neighboring town. It was a long drive and I was feeling a bit drunk with a few swigs of the bottle on the way over. This made it much easier for me to have the nerve to do this.

We got out of the car and Tisha came around to my side. She adjusted my skirt and told me to lean on the car with my hands. I did and she grabbed the dangling strings of the corset and began to tighten it more. She jammed in her knee into my back as she pulled hard.

"You don't need the room anymore."

Tisha yanked and pulled for about five minutes asking me to breath deep and slow. With each deep breath I took she pulled the corset tighter. My exhale was never the same output as my inhale. Finally she finished and I could see I now had a true hour glass shape. Tisha tied the laces off and bundled up the slack.

We walked up to the front door and Tisha rang the bell.

"Tisha, What a pleasant surprise! I was so disappointed when I heard you hadn't confirmed your partner. I am thrilled you made it and what a great combo costume! The contest will be a little later so please grab a drink and mingle."

"That was Amber." Tisha said. "Our host. Be especially nice to her."

Tisha and I mingled. I saw a Witch and Dorothy together, Sonny and Cher, Raggedy Ann and Andy and other combos. In each case I had a hard time telling whether or not the female character was a male or a female.

Women definitely out numbered men at this party and I began to get a little nervous of the odds. At least the perceived odds. I couldn't tell anymore. Based on my transformation I could be dead wrong on either character at this point.

Walking in the heels was taking its toll. It was a good thing Tisha had me practice more at her place so at least I wasn't awkward about it.

Tisha and I were sitting on the couch as Tisha was rubbing my crotch saying "I think you just might be my type after all." I was getting horny. Then Amber entered the room and announced that we were going to be bobbing for apples. Each apple was numbered and after all of the apples were retrieved they were going to draw a number out of a hat. Whomever had retrieved the corresponding apple was the winner and the prize was a full treatment at the Russian spa in town.

Tisha lit up with excitement.

"Oh My God! We have to do this. I want to win. I mean, I want you to win for me. For us."


"Yes, no offense but you have the bigger mouth." Your chances of even getting an apple are better. Look how little my mouth is." as she opened wide to show me.

"All right, what the Hell. No guarantees though."

Amber was still giving directions but I missed most of them. The room cleared and most of the guests headed downstairs to what I assume was a basement. The couples playing stayed behind.

There were five couples remaining and the Wizard of Oz couple and the Raggedies were among them.

Amber walked around the room and handed a small satchel to each contestant. As she handed one to Tisha, She politely asked if she could demonstrate the next instructions with me. Tisha obliged.

Amber asked me stand up and while describing to the teams she withdrew a coil of rope from within the bag.

"Bobbing for apples is a hands free game so please tie your contestants hands behind his back. It is important to do it just like this so please follow along.

"his back" I thought. It's all guys bobbing?

As she explained, Amber crossed my wrists behind my back, folded the rope in half and began looping a coil around my wrists pulling the rope back through the folded end. She synched it tight and began wrapping the rope around and through my wrists several times. The last loop she wrapped between my hands and forearms and pulled it tight down on the other wraps. She explained this part carefully to the group. She tied it off and held up the remaining rope telling everyone they should still have about two feet of rope remaining. This she wrapped around the small of my corset and brought it back around and through itself in the back and back around my waist yet again in the opposite direction finally tying it off in the back. Amber explained that there needn't be any wandering arms trying to get at the apples.

This woman was serious about her games!

My wrists were now effectively secured and crossed together pined tightly against the small of my back.

Amber looked at Tisha and said "I hand him now helpless back to you."

Amber explained that each bag was numbered and that was the order in which we would be called downstairs. We had bag #3. She went on to explain that bobbing for apples was more fun if we couldn't see them so in the bag was a pair of blacked out swim goggles for us to put on before we went down.

I was now even more nervous but Tisha was having so much fun and was giddy with excitement that I didn't want to say anything.

First went the Wicked Witch and Dorothy. The Witch leading a blind Dorothy through the doorway to the basement. I heard muffled announcements and a lot of cheering going on.

A long ten minutes later it was Raggedy Ann and Andy who descended into the basement. I knew we were up next.

"How are you sexy?" asked Tisha.

"Ready to bob my way to your heart Jeeves." I was lying.

The door opened signaling our turn and Tisha pulled the goggles over my eyes effectively shutting off the world around me. She kept close as I leaned into her for guidance as we took the first step. A few steps down I heard the announcer.

"And here comes Tisha with contestant number three. Maybe the sexiest chamber maid I have ever seen."

Lots of cheering and cat whistles.

"Look at those legs will you! And what do you think she has on under that skirt?!"

"Roaring cheers now and I feel hands touching my ass and waist as we descend the final few steps. I am turning beet red even though I know nobody here knows me.

"And those lips! With the "fuck me now" red lipstick. Great choice Tisha!"

I am moved to a spot in the room and told it is time to bob for an apple. That there is a support beam in front of me that I can lean into without fear of falling over. I am told to lean forward now to locate it.

I lean forward with helping hands on both sides and I find the padded beam. It rests squarely at my hips. What I don't see or feel is that the person on the side of me feeds a strap over my waist and under my pinned arms and through a buckle on my other side.

"On the count of three, open wide and bob away for the winning apple. One, Two Three!"

As I open my mouth and move my head downward instead of getting a face full of water like I expected I was met with a hand holding a round object - not an apple - that was crammed into my mouth and quickly strapped around my neck. At the same time the strap at my waist was pulled tight and fastened and my legs were kicked out to either side and simultaneously strapped down.

I fight with everything I have but it's too late. I am stuck. I am screaming into the gag but to no avail. People are cheering so loud I can barely hear myself.

The goggles are pulled from my eyes and I look up but only see a wall. I scan to my left and there is Raggedy Ann and Dorothy in the same position I am. Ann lays limp and has her/his head hung low and drool is dripping from his mouth forming a pool on the ground. Dorothy's veins are popping out on his forehead and his muscles are pulsating as he struggles to free himself from his binds.

A voice behind my ear speaks.

"Welcome to the initiation of Tisha, This next part is going to hurt you a lot more than it will hurt her."

With that I hear the announcer again.

"Let's hear it for contestant number one - Jessica's Dorothy!" - Whoops and cheers ensue.
"And contestant number two - Molly's Raggedy Ann!" - As she says "two" I see Raggedy Ann stiffen up quickly and brace for something that does not come. - More cheers but not as loud as the first.
"And now contestant number three - Tisha's Chamber Maid!  And with "three" came the hardest "whack" on my exposed ass I have ever experienced in my life. I could hear the paddle whistle through the air before it made contact. I let out a muffled scream that nobody could hear over the cheering and hollering. Tears welled up in my eyes and I cursed the situation I was in.
The evening saw three more contestants that met identical fates as I watched from my secure position. Raggedy Ann stiffened every time the announcer said "two" as if expecting another blow from the paddle but one never came... for any of us after the first.

I was aided to Tisha's car at the end of the ordeal still bound. I was placed lying down on the back seat and driven to Tisha's  house. She helped me upstairs and still bound she cut her panties off of me and rode my rock hard cock into the morning.

She untied my wrists and I was too defeated to do anything and my ass was too sore to ride my bike home. I slept the day away with Tisha. Still clothed and corseted we fucked a few more times through the day as Tisha kept calling me her little slut.
At one point when I made it to the bathroom to pee I inspected my red ass in the mirror and saw in outlined letters across my right cheek "SLUT". I smiled.



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