The best Halloween I had was the year of 2005. However, let me explain a few things about me 1st to start I am a bondage freak I love it. I am 31 and have yet to be in a BDSM relationship so I do allot of self-bondage but this story is not one of those times. It all started September 1st, a female friend of mine who knows about the stuff I am into but are too good an old friend’s to-do anything with each other’s. We were drinking coffee at her house and she asked me if I wanted to go to a Halloween party with her, I said yes but was not sure what I would wear since I wasn’t to good at the whole dress up thing. She stated she would call me few days before with some ideas.
A few days before I get her call what she said sort of shocked me. She stated she was to go as a Domme since it would be a simple costume. What shocked me was the fact she never was interested in BDSM. I asked her what changed her mind she laughed and said nothing changed it it just sounded like fun. Cool I told her she asked me what I would be going as or did she still need to give me some ideas I asked for the ideas.
1st Idea: Spiderman. I hate spider man so I said no
2nd Idea: Death I laughed and said no to normal
3rd Idea: Was to go as a girl / Laughing my ass off I said no I was so not into crossdressing <thou I do have a little hiding fetish NO ONE knows about but me.>
4th Idea and the one that shocked me for the 2nd time in less thing an hour was to simply go as her slave
Laughing I said how was this suppose to work? She said just wear some shorts, a t-shirt and maybe some cuffs for added effect. Hmmmm simple cheap and sort of a simple thrill for me. I laughed and said yea sounds like fun.
Halloween Day
My cell phone rings at 9am, grrrrr I growl to myself as I answer the phone Its my friend asking me if we're still on for the party.
"Jess," I say, that’s her name of course, "we're still on for the party."
"Good!" she said, "I'll be there in a hour." and the phone went dead .
A freaking hour what the hell its only 9am and the party is not until 9pm, 12 hours from now, a little damn early I think to be picked up for it.
10am my doorbell rings, damn I think must have fell back to sleep, rolling out of bed I answer the door and there is Jess.
"What do you want?" I groan half-asleep still.
"Got you some clothes for tonight," she said and tosses a bag on the chair.
Looking at it I said, "I thought I was only suppose to use shorts and a t-shirt?"
"You are, but this is a black leather shirt and shorts, thought it would look better."
Nodding I say, "Sure whatever, come in for some coffee".
She comes into the house and heads for the kitchen, SHIT I think I forgot to put my bag of toys away from the night before. Yes she knows what I am into and what I do but have never shown her any of my toys or told her about them.
Looking at the bag she laughs and says, "This your little bag of toys, you naughty boy!"
Blushing I answer her with a soft yes.
She just laughs and says, "Cool can I look to see if there is anything else in there we could add to yours or my costume?"
I simply nod yes, thinking they'll be too perverted for her simple taste. Looking through the bag she pulls out a few items that I do not pay much attention to since, I am now sipping my coffee just trying to wake up. Staring me she says, "I put what I need and we can use in my bag, I'll see you at my house at 8.30." Nodding again I said sure not thinking of what she would have taking since I am still not very awake.
7pm Halloween night
I arrive at her house wearing the black leather shirt and shorts and my CBx26m < this CBx26m is a chastity belt allot like the CB300 but made of an uncutable metal alloy > It is now 7 pm just early enough to piss her off. Hey, she woke me up why not bug her some. Knocking on her door she open it wearing what looked like a catwomen costume without the mask. "Nice outfit," I say.
"Ggood your early we can get ready!"
Damn didn’t piss her off any. Looking down and back at her, I tell her I am already dressed and btw these shorts suck.
Laughing she pulls me into the door and says, "You're not ready yet, I want to win the costume contest!" < as if her in an old catwomen costume and me in a leather shirt and leather shorts this won't win > Tossing a bag next to me she says, "Put those on, they will make us look more real."
Looking into the bag, I find my red ballgag, my leather collar and my waist belt that has a D ring in the back. "You sure you are not into this type of stuff Jess?" I jokingly say.
"Nope I am not, I just want to win the $500 prize."
Laughing I slip on the waist belt and buckle it in front and slip the cuffs thru the back D ring, not locking the cuffs on yet.
Looking at me Jess says, "Well?"
" Well what?" I ask.
"Are you going get ready so we can go!"
"What do you mean?" I reply.
"Tthe cuffs and gag!"
Shit I think she really wants me to lock them on to look real. "I'll put them on as soon as we get there."
" No, no can't do that!" she jumps in with, "they have valet and I want to look good from the start."
Sighing I reach my hands behind myself and lock the cuffs, the keys are on my keying I inform her.
Turning around looking at me she says, "Shit you forgot the gag!"
"I am not wearing the gag," I said, "this is real enough!"
Nodding to me she agreed with this so I thought. "Let me double lock those for you." Turning around and holding out my hands as much as I could I feel her double lock them. "Shit the key broke!" I here her say as I open my mouth to say 'what!!!' She slips the ballgag between my teeth before I can stop it I hear it buckle shut. Looking back at her with an evil eye, I let out a loud 'MMPPPFFF'
Laughing she says, "You have to admit this does look more real."
I roll my eyes to this.
"I have few more additions I want to make to your costume." she says as she reaches into the bag on the table and pulling out three small locks and my leather collar. I shake my head no and MMMPPFF into my gag.
"It's this or I go to the party without you and I'll just put you outside before I go, don’t want you in my house without me here."
Now yes its Halloween night and this might not look too out of place to walk home in, but still if I did make it home this would be a bitch to get out off, so I roll my eyes and nod at her. I feel the soft touch of the collar go around my neck. Lucky I am wearing my CBx26m, unknowing to her so my liking of this does not show through to her. As I hear locks being snapped shut I moan from behind my gag, this is the 1st time anyone else had me fully at their mercy and needless to say I was a little nervous.
"Ok we're ready, let us go!" she says. I simply roll my eyes at this.
The trip there was very simple. We get there and she pulls up to the Valet. 'Big house!' I think to myself, 'damn. should have asked her before all this whose party it was.'
Jess goes to the passenger door, opens it up for me, and snaps a leash onto the collar, I keep an evil eye on her. As she leads me into the front doors, I look around the big house and see everything from space men to big adult babies walking around, well at lest this will not look strange I think to myself. A tug on the leash has me following her into the main room and onto the main dance floor for the next hour or so, we dance around the floor looking somewhat funny but having fun.
The award speech
It's now midnight and there starting to announce the winners of the night. Best costume went to a bear; most original went to Frankenstein; strange went to a big adult baby boy with a dirty diaper. In addition, most unique couples costume to my shock went to us, the Domme and Slave. As she leads me up to the stage I think, 'Well at least she won the big prize, maybe she will split with me.' The announcer ask us both to make a small speech I mumble under my gag mostly to say thanks to him, since I know that that gag will have to be removed for me to do this and at this point I want it OUT, its hurting and my shirt is covered in drool . Jess does her little speech making it short and simple, she turns to me and back to the mic. "Since my slave can't talk I'll read the speech he wrote in case we won."
' What speech! I did not write any speech, hell I didn’t know about this until she told me!' I MMMPPP over the gag but it just make it look like I am agreeing with her. "The speech he wrote goes like this.."
My speech
"Thanks to everyone who voted for us. This money will be put to good use < I roll my eyes at this> the money will be donated to my fav charity but 500 is just not enough to do allot of help, so I'd like to make you all an offer."
I am really starting to worry here what the hell she is talking about. She keeps talking and my heart sinks with each word.
"I have given my Mistress the keys to my locks, all four of them."
'Four of them I think, wait there not four there 3, one for the gag, one for the collar and one for the waist belt what is she talking about?'
"All these keys are up for bid, they maybe resold or used in anyway you wish within the law and safety to my slave with no harm to him. I will not tell you what key goes for what."
At this point, I am in shock and am almost yelling over my gag and all it is doing is making the room more into this.
"The first key will start at $100."
The big baby boy I see raise his hand, 'shit no this must be one of her jokes!'
" 100 I have 100, do I hear 150? Anyone?" From the back of the crowd I hear "I'll give you 500 each if I can have them all."
It was a very young girl in a cheerleader outfit most likely in her early 20s. "I have 500 each do I hear more?? 500 going once, going twice, sold to the cheerleader. You can pay me at the bottom of the stairs." she says and grasps my leash and leads me down to the bottom of the stairs.
The cheerleader
The young girl arrives at the stairs and I almost die, it's my sisters best friend who I always tease and give her a bad time every time I see her with my sis . Winking at me she hands Jess the money and takes my leash. "Time for payback slave!"
My heart skips a beat as she pulls me away from Jess. 'MPPPGGGFFF' from behind the gag shaking my head no, looking at Jess who just gives me a wink as she turns and walks away counting the damn money.
The Girl who we will call Val, since she asked me not to use her real name was tugging on my leash as she lead me down a dark hallway away from the main house where every one else is. At this point I am really pulling on the cuffs hoping they will break or something, but to my horror they do not. I 'MMMPPPPFFF' into my gag and as we walk into a dark room, she pushes me onto the bed, I look up at her with pleading eyes.
"Do not worry slave, thou you did not agree to this, I'll stick to Jess's rules."
My eyes widen how did she know I did not agree with this. Looking down at me she can see the questions in my eyes.
"You couldn’t be so dumb as to auction keys off to your bondage Shawn, so either your were tricked or you're just dumb and I think you were tricked, am I right?"
I shake my head yes still pleading from behind the gag.
Laughing she holds up all four keys in front of me, what the hell is that fourth key for I think.
"Let us see what the keys go to that, Jess gave me, she says lets start with this one." Taking one of the keys and pushing it into the padlock on the ballgag. "Nope that’s not it, lets check the belt."
She slips the key in and it unlocks looking up at me she smiles and relocks it, "We're not ready for that yet!"
Taking the 2nd key and placing in the collar it unlocks. "Hmmm!" she says, "we will just leave that on as well."
Taking the third key and trying it into the ballgag lock it does not fit. "Well that means the fourth key goes to your gag, but what is this fourth one for? It is not the cuff key, that I got free hmmm I wonder?"
Pulling me by the leash back onto my feet she smiles at me, reaches down, and pulls down the leather shorts. Blushing redder than ever and trying to yell stop before she looks, too late. There I am standing in front of her with a red thong of hers that I snagged last time I was at my sisters and my dam CBx26m poking out from behind it.
"You freaking pervert!" she softy says, "those are mine!" Pulling them down and revealing my CBx26m. "And I bet this is where this key goes!"
My heart stopped as I realized that Jess must have seen the key and the CBx26m in the bag and took the key. Laughing and pushing me back onto the bed and straddling over me, looking down with an evil grin on her face. She pulls out her cell phone and starts snapping pics with it as I yell and wiggle beneath her begging her to stop. Shaking her head no, she just laughs and sets down the phone and softy spoke. "I have password protected my phone and have set a time delay message to send your pics out to everyone on my phone in 55 mins."
I start yelling from behind the gag trying to kick her off me.
"I have over 200 contacts!" she tells me, "and those include your sis and your parents."
My eyes widen in shock and horror, there nothing I can do as I feel a tear roll down my face.
"You are now mine for the next hour and if you try anything those pics will be sent out, so its up to you to behave, do you agree?"
I shake my head no, still not realizing the full Crud I am in. She simply shrugs and gets off me and head for the door with her cell phone in hand .'MMMMMPPPFFFF' I scream from behind the gag. Turning to look back at me, "Do you agree slave?"
Nodding yes fast this time, I lay there shaking.
"Good boy!" she says."I am about to remove the gag now and you are not to speak or make any noise unless spoken to first understood?"
I nod yes with tears rolling down my face. Slowly but softly she unlocks the ball gag and pulls it out with a pop, my jaw is killing me now its 2am and it was in since 8pm. I wiggle it to get it loose again and start to speak. "Don’t you dare speak Shawn remember what I said, you don’t obey I leave and just let those pics get sent."
I just nod my head looking at her with puppy eyes. Shaking my head I realize she is stroking my member with her foot. Shit I think I cannot get hard in this damn thing, after getting the cobwebs out of my mind I realize she is sliding up my chest, I can feel her wet pussy pressed up against me.
"Let us hope your good with that mouth Shawn!" she says as she lowered herself onto of my face. Her heat and wetness engulf my face and mix with my tears and sweat. I lay there trying to breath under her, hardly able to as I feel her slap my balls with her foot.
"Lick it Shawn or I'll kick it twice as hard."
I slowly raise my mouth to her hole and start to lick her out, breathing through my nose I suck up a nose full of her wetness, after a few minutes I feel her rocking and can hear her moaning loudly. I feel a rush of wetness engulf me as her first orgasm hits. Sliding down off me and laying next to me she softy asks "Did you enjoy that Shawn?"
I simply nodded yes. "You may speak as long as it is nice and not to fight what I am doing with you."
I softy say, "Yes Val I did."
A fast and loud smack to my balls with her hand has me in tears looking at her. "That’s yes Mistress to you Shawn!"
Gasping trying to catch my breath from the pain in my balls. I mutter out yes Mistress as best I can.
The set up to go to her house
"Good boy Shawn, we're gonna go on a trip to my house, so you had better behave as we leave, just remember I have not reset the timer on my phone yet."
I simply nod still gasping in pain, "Yes Mistress," I say as she pulls me back to my feet and slides the thong and leather shorts back on me, softy smacking my balls. Gasping from each smack in fear of another hard one, I see her pick up the ballgag and lock Shit I think.
"Open up Shawn!" she says with a stern voice.
"No, please Val my jaw already hurts, I'll behave I swear."
" Ok Shawn you do not have to wear the gag, but if you don’t wear the gag you do not wear the shorts either."
At this point I am in a catch 22, if I wear the gag there's no way I can tell anyone to help, if I don’t I'll be walking out in a thong and a CBx26m and they’ll be too busy laughing to help me. <What would you do?> Sighing I agree to the gag and open my mouth. Popping the gag back behind my teeth she relocks it and I hear the lock snap shut again. Reaching into her purse I see her pull out to my horror a pair of alligator nipple clamps.
"Your sis never told you that I am into this as well did she?" she asks me.
Shaking my head no I feel the sudden snap of the first clip snap onto my left nipple. 'MMMMMppphinh' and yelling from behind the gag as the pain kicks in as she scratched up and down my right nipple with her fingernail. Leaning down and softy licking it, I lean my head back in a small amount of pleasure before having the 2nd clamp slip on with a loud yelp from behind my gag as the pain rises in the other nipple. Reaching up she undoes the leash around my collar and clips it to the chain between the nipple clamps. Sitting down on the bed smiling at me she starts to untie her shoes, slipping them off, and removing her socks, I just stare at her with wonder and fright. She stands and picks up one of her socks and proceeds to blindfold me. Shit now I cannot see to tell if I can get someone to help me out of this.
The trip to her house
A sudden tug on the nipple clamps tell me to follow the pull, as I am lead out of the room. I can hear the music playing and people still having a good time. Mpphing from behind my gag in hopes to get someone to stop and talk with us seems futile as no one does. All I can do is follow the tugs on my ever-increasing sore nipples. A sound of a door open and the rain falling on my face indicates were now outside as I hear her talking to Valet. The female Valet tell her its $5 for the parking fee. "I'll show you something funny as hell if you do not charge me!" I hear Val say.
The female Valet must have just nodded because I did not hear her say anything and the next thing I knew my shorts were getting pulled down. 'NOOOO!' I scream from behind the gag only to be heard as MMMPPPPOOMM. The sound of the female laughing told me the $5 fee was just paid at my expense. "In addition, for your tip why don’t you play with the little prick!" I hear.
Struggling pulling back on the nipple chains I try to avoid this due to the fact that I can't get hard in this damn CBx26m. Moaning loudly as I feel her stroking my cage my member strains against it trying to get hard. "You can keep the shorts or toss them if you want, he won't need them anymore."
My heart skips a beat hearing this now I am going have to ride to her house in nothing but her thong and a CBx26m, 'Could this get anymore humiliating' I think to myself as I feel a tug on the clamps and am lead to the car door. Pushing me into the front seat and closing the front door all I can do is sit there as I hear the car start. Most of the trip there was uninteresting. All I can do was sit there and think about what was to come next. I am shook out of my thoughts with the sounds of sirens behind us .'Ohhh this is just great!' I think to myself, now we're about to be arrested. I feel the car pull over to the side of the road and the siren stops just behind us.
"Remember the pics Shawn do not try anything!" I just MMMPPPPP from behind the gag in agreement <I mean what else could I do?> I hear Val roll down her window and a female officer speak, "Licence and registration please Madam".
The Officer
Ohh great I think it had to be a female officer. A Laugh from the female officer indicates to me she has just noticed my outfit, I blush an apple red as I feel her eyes on me. "Just come from a kinky Halloween party?" the Female officer asks.
"No my friend here just gets a thrill doing this from time to time." I hear Val respond to her. I am blushing so bad right now; I must look like a human tomato. I Mpppp from behind the gag trying to indicate that it is a lie.
"Is she lying Sir?" the female officer asks. I am about to nod but the sudden thought of her cell phone and those damn pictures comes back into my head. I simply shake my head no and roll my eyes from behind my blindfold not believing I just let maybe my one chance of help slip through my fingers.
"Madam this licence is expired." I here her say. I hear Val plead with the officer not to write her a ticket since she has had too many and would loose her licence. "I'll be right back," the officer says as I hear her walk away from the window.
I laugh from behind my gag thinking I just had a little payback myself with a loud smack and a rush of pain through my head as Val’s hand lands on my balls. A fresh tear rolls down my face as I hear the Officer walk back up to the car. "Please sign this Madam," I hear the officer say. Val starts pleading with her again not to give her it, that she would mail the officer money if she would not give a ticket to her.
"I'll make you a deal you give me the key to that CBx26m and I'll hold onto it until you send me the money and I will not issue this ticket."
I hear keys rattle, I start to yell from behind my gag but it seems like both of them are ignoring me. "Here's my address to mail me the money," the officer says as I hear her walk away at this point I am sobbing from behind my sock blindfold.
"Well that’s one ticket I won't have to pay!" Val says as I hear the car start up and began it journey to her house again. At this point, I would give everything I own to get out of this. The rest of the trip I just sit there crying behind my sock blindfold wishing I had just gone as Spiderman ohhh why did I not just go as Spiderman. The car comes to a halt and Val announces we are at her house. Her door opens and shuts as I hear mine open and a tug on my nipple chain tell me to get out. Not sure what time it is I pray its still dark out and no one will see me as she tugs on the chain leading me up to her front door. I can make out the sound of the key sliding in and the door opening. My only thought is what will lie behind that door for me.
To be continued in part 2
/ If you like this story please email me and let me know. Also in part 2 I will be including anyone who wishes a part in it. If you wish a part in part 2 please email me the name you would like used and the type off role you would like to have for example < Jane Doe Bi female Doctor . / And a description of yourself if you wish that to be included. Let us give part 2 a personal flare people. Depending on who emails me for a role and how many will determine were this story goes from here. The deadline for a role in part 2 will be November 1 so that I can get part 2 out by Dec 1st
Thanks for reading this and I hope you enjoyed it and will join our victim in part 2 of The Bondage Halloween
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31.10.07 | updated - 07.05.17