The damndest things can happen on Halloween

You want me to do what. I doo no. I’m not sure I can, I mean look at how big that is.

I was at a Halloween party with a bunch of people I didn’t know after my girlfriend got pissy because I looked better then she did and left.
Let’s back this up two days !!!
We’ve been invited to Tammy’s Halloween party Saturday night, my girlfriend Carol told me. It’s a maskarade party. We gotta get costumes.
Oh great I said. Tammy is the rich bitch that’s been after my dick since grade 9. I’m not into her. Way to snobby for my liking.
Carol on the other had is the complete opposite. Loving, Caring and a great mind and body. Believe me, I’m one lucky guy. But she is a bit self conscious. Don’t get me wrong, I’m good looking and all and I am a loving, caring honest person. I’d never cheat on her.
What kind of costume are you thinking I ask knowing she already has a plan.
She gets this devilish grin, you know the type of grin that says she’s in the mood for sex.
She’s the dominant one in our relationship so I usually just let her have it her way.
She leans in and kisses me then pulled away and says I’m going to be your boyfriend !
I have a slim sleek build with chestnut brown hair down to just above my hips.
I just smiled and said well I guess that makes me your girlfriend ! Not letting that sink in at all.
You got that right she says.
Wait, what ! Me your what ? I stammer out.
You are going as a girl and I’m going as a boy !
So let’s go. We’ve got a few appointments to make it to. And out the door we went.
A short drive later we were at the salon she always goes to.
Carol, it so nice to see you a lady behind the counter says. And you must be my one o’clock appointment. She looked right at me as she said that.
Um ya, I guess that would be me I said. Like I said when Carol gets to planning something, I just need to show up and do what she says.
Come on handsome. We got a bit of work to do as she pointed to a chair.
I looked at Carol as she gave me a quick peck on the lips and said have fun and I’ll be back in a while. She spun on her heals and was out the door just like to that.
So what are you going to do to me I ask.
Hunny, your not gonna recognize yourself when I’m done.
A couple hours went by in a blink of an eye.
Oh wow sweetie, you look amazing Carol said when she got back holding a bunch of shopping bags.
I was a bit pissed when I ask her what the heck am I going to to with these as I held up my manicure nails. Bright red with gold and silver zig zags on them.
Carol ignored my displeasure and complemented the lady on a jod well done.
My hair was cut just below my shoulder blades, styled and permed. My finger and toe nails we’re painted to match.
I have to admit, I did look pretty good. But I’m definitely a straight guy.
Okay, let’s go. Your next appointment is only a few minutes from now.
Carol paid and we left.
Walking out to the car I had my hands in my pockets but my toe nails stuck out like a sore thumb in my flip flops.
We stopped at our next destination, a beautician. Carol looked at me and said just trust me sweetie.
I didn’t say a word. I just went in and sat in the chair. I saw Carol talking with the lady at the counter then she left.
Okay so have you ever applied makeup before she asked. I just looked at her, I didn’t think so but I gotta ask, ok let’s get started she says.
Again the time seemed to just fly by. This time I was done before Carol got back so I was sitting in the waiting room as she walked right past me to the counter.
Can I help you one of the ladies asked Carol.
Yes, I’m here to pick up my boyfriend. She just pointing at me and said is that him.
Carol looked at me and for the first time she was speechless.
She walked up to me slowly as she looked me over. My God you look fabulous she said to me.
Ya can we go now I ask as I got up.
The car ride back home was awkward to say the least. She kept stealing glances at me.
Once home we got inside and she says I got you your outfit, I’ll help you get into it so we know everything fits.
Carol has a great eye for sizes. Everything she got fit perfectly except the heels.
I looked at myself in the floor length mirror and was stunned. A smile was on my face in no time.
I had on a white long sleeve pullover cardigan with a slight plunge to the front neck line. A light blue tight skirt that had a cut up the middle back. Black low platform heels about 2” with thick bands and a buckle up on the outside. Along with a regular beige bra and some C cup breast forms and matching granny panties.
You like it, don’t you Lisa, she says.
Looking back at her confused I say “Lisa”.
She smiles and says we’ll I can’t very well call you Todd dressed like that now can I.
I looked back at the mirror as I said Lisa. I like it.
Something happened to me as I adored myself in that mirror that I didn’t understand right away.
Well let’s go Lisa, we gotta get you some heels to go with that outfit Carol said.
She grabbed her car keys and headed for the door.
I just stood there and said, what, like this ?
She stopped and gave me that look that says move your ass ! I put my runner’s on and followed her out the door.
Embarrassed as I felt I also felt liberated and proud.
We got to the shop she got the shoes from and the male attendant ask if he could help us.
Yes I bought these shoes for my girlfriend Lisa here and they don’t fit I need to get a different pair please, I’m not sure about the color so can we try a few different shoes on now. I was asked to sit at a chair and this guy asked me what kind of shoes I wanted.
Something easy to walk in I said.
She’s such a kidder Carol laughed out. Can she try on the 6 inch red stilettos please in a size 9.
He was back before I could ask Carol what she was doing.
He grabs the back of my foot and tries to fit the shoe on my foot.
Seems to be a size too small he says as he gets up and disappeared into the back again.
I just look at Carol as he came running out again. Carol was grinning from ear to ear. She was enjoying this so I decided to show her I could have fun too.
This time I lifted my lower leg up exposing my panty clad penis to the guy. He stopped dead in his tracks for a moment. As he looked me in the eye. Knowing he saw everything I said oh dear. I’m sorry, I still getting used to being a lady. He slipped the shoe on and I stood up to walk around.
Carol’s smile was gone now, instead she was just looking at me like I did something she didn’t expect.
Carol handed the attendant my runner’s and asked him to toss them in the trash. She will ware the stilettos out.
That put a smile on her face again.
Will that be all for you sir the attendant asked me.
Yes, thank you I say as I tried to walk in them.
No, Carol said. I think the gentleman needs a pair of black knee high boots to please.
He went to get the boots as I ask why do I need them for.
Well you can hardly walk in these and boots are lower heel so you will be able to walk in then easier.
I tried on a couple pairs of boots and found a pair that fit nicely. Black, very shinny with red ribbons and a 5 inch heel that came down to a point.
I paid for them and expected to head home but Carol had other ideas. We stopped at a clothing shop and Carol looked at me and said I realize now that you’re dress is not inappropriate enough so let’s see what we can find for the little slut. She left me stunned in the car. She never talks like that.
I followed her in the store and she headed to the Goth section. She pulled a very skimpy dress like thing off the hanger and held it up to me. No she said as she throws it on top of the rack.
She tries another and another until she finds one that would have shown a lot more then it would have covered and said here slut. Go put this on now.
I knew I’d better just do as she asks as she was really mad.
I got into the changing room and took off the dress I was wareing and slipped this skimpy thing on. The under garments Carol had me put on before were very visible.
Carol asked what was taking so long so I opened the door, well slut get out here and let’s see you she insisted.
I stepped out in front of the mirror and Carol leaned in and asked me if I felt like a slut yet.
I asked here if this was the right under garments for this outfit ? She said wait right here. She headed off into the store, a male attendant aproched me with a huge smile and said wow. That looks great on you. Can I help you. I asked him what kind of under garments I should ware with this dress.
He just laughed and said that’s not a dress, it’s just a low cut t-shirt.
If your going to ware it as a dress I’d recommend some pantyhose and probably a skirt of some kind.
Okay can you get me some please.
I thought you’d ask so I brought you some designer pantyhose.
I went into the changing room and put them on over my beige panties. I came back out and looked at myself again. That’s better I said.
Are you gonna ware that bra under the t. Or can I recommend something else. He hands me a black lace low cut bra with a pink bow where each nipple would be.
I took it and went back to the changing room.
When I was changed I came out and Carol was standing there. I looked at myself again and was very happy with how I looked.
Carol wispered in my ear. Lisa’s looking rather sluty in a very good way.
The bra was a push-up type bra and with the breast forms made it look like I had rather large tits. The low cut croped t-shirt came down to just below my waist. And revealed almost my full bra. The pink bows we’re on the very edge of the T-shirt. The black embroidered pantyhose had a high shine to them with a red stripe down the back of them from my heel to my tight little ass. Carol handed me a very short silver shinny skirt so I slid it on. It didn’t do much more the hide the waistband of the pantyhose. She handed me a french style cap and helped me put it on.
Carol hung a necklace around my neck that came down into my fake cleavage.
She also gave me a few bangle bracletts and a gold anklet. Last she put a slave ring on my middle finger and said I own you now !
Carol didn’t sound mad anymore. I wasn’t sure until we got home. We were walking up the walkway when she pushed me up against the tree and kissed me very aggressively she reached into my pantyhose and pulled my cock out. She pulled on it hard making me wince in pain. Then she dropped to her knees and blew me right there.
I came quickly as this was the first blowjob she’s ever given me. Fuck was it ever good.
She cleaned me up then pulled my pantyhose and skirt back into place.
She got up and kissed me hard forcing some cum into my mouth. This was the first time I ever tasted cum and I loved it. I swallowed it and showed her my mouth was empty.
You naughty little slut Lisa !
Hearing her call me that made me feel so good.
We went inside and she told me she was so mad at me in the shoe store but then when I put this outfit together she just felt so fuckin hot for me. She asked if I wanted to fuck to witch I said of course.
Our love making sessions were usually tame, not on this night though. I truly felt like a piece of meat as she took me every way she could.
The next day, Halloween, Saturday we woke up after noon. So we were well rested. Hunny your makeup is ruined, we will have to get you an appointment to get your makeup done again.
Ok I said. I’ll go get it done, you gotta get ready. I put my new outfit on with the the stiletto high heels and headed out the door.
As I got in the car I heard Mr Watson from across the street cat whistling at me. I just smiled as I drove off. I got to the beautician and ask her if I could get my makeup redone, she said not the same way it was, not if you’re wearing that let me see what I can do.
When I left me makeup was done a lot darker, black eye shadow and eye liner and blood red lips.
Walking back to the car I ran into Brad, a friend from back in grade 6. He started talking to me but I got the impression he didn’t recognize me.
Are you from around here, I’m only asking because I might be able to help you out, if you know what I mean.
I told him I was going to Tammy’s Halloween party tonight.
Cool. I’ll be there. See you later he said as he stopped and I kept walking. I really was getting the hang of these heels.
I got back home and Carol, or should I say Carl was ready to go. She was dressed as a hittman complete with a mustache and goatee.
Carol commented on my makeup and I told her this is what she did so I went with it.
We got to the party and no one recognized me or Carol all night. Tammy got druck and disappeared upstairs somewhere.
Brad was there but his girlfriend had him on a short leash it seamed.
Carol and I were nominated for best costume along with half the people there. Carol was drinking most of the night and got really pissy when I won. She left me there and took a cab home.
I stayed and mingled. I didn’t know Most of the people there. Except Brad. His girlfriend had left too when Brad found me and started hitting on me.
I wanted to have fun with him so I didn’t tell him who I was. He was trying real hard to pick me up and I was stringing him along.
Hay what you say we go up stairs and fool around.
Im not sure your girlfriend would approve I said.
Well she’s not here and I’m not gonna tell her so what do ya say. I’m hung like a horse you know.
I’m not sure what happened but when he said that I got intrigued.
A horse you say, well I’ll need proof of that ?
Put your hand on my thigh he said as he looked me in the eyes.
He moved in closer to me on the love seat we were sitting on. I put my hand on his knee while I looked him back in the eye. I didn’t have to move my hand far when I felt his cock in his pants leg. My eyes got big as i realized he wasn’t lieing. Let’s go see this horse cock of yours I said as I got up and grabbed his hand.
Maybe it was the alcohol I had that night, maybe it was lust but all I know is I felt so right, so intrigued, so horny, I didn’t hesitate at all as I went upstairs with him.
We found a bedroom that looked like no one was in and we entered. Brad locked the door and turned on the light. No, trun the light off I said. So he did.
The full moon light was shining in through the window. He came up behind me as I was looking out and kissed my neck.
My body reacted a lot different then I expected. I leaned my head to the left as he kissed my right side. I seamed to melt in his grasp. He put his hands on my waist and my ass seamed to search for his crotch. He stepped closer and slid his hands up to my fake tits. I tilted my head back to his shoulder. He kissed my lips and slid his tongue in my mouth. I returned his kiss and let my arms hang down. I felt my way to his crotch. My hands searching for his manhood. He turned me around kissing me full on my mouth. My hand move almost instinctively. As I undo his zipper. He slides his hands down to my ass and pulled me in closer, pinning my hands tight to his crotch. Now I can feel it. It’s a hell of a lot bigger the my 6 incher but I don’t panic as I’m literally lost in the kiss we share. I’m still trying to free his cock almost feeling desperate. He steps back a half step and I undo his button of his jeans he’s a fantastic kisser I’ll give him that.
Finally I’m at the point where I can pull his pants down so I break our kiss and slide down with his pants.
His massive cock springs up out of his pants and hits me in the face hard.
Ouch I say as I close my eyes.
I open my eyes a moment later knowing full well his cock is mear inches from my lips. As I study his cock in the moon light for what seamed an eternity. I finally reach out with my right hand and touch it ever so softly. Almost afrad I might break it.
Told ya didn’t I, now suck it all down Brad says.
You want me to do what. I doo no. I’m not sure I can, I mean look at how big that is.
You can do it. Trust me.
I grab him in my right hand and as my fingers tightly try to rap around his girth I’m left speechless. My fingers could not close around it like they do with mine.
I don’t know why but I felt so turned on at that very moment so I closed my eyes and started to lick his shaft. As my tounge made contact with him, I felt so hungry, so dirty, so sluty. I had to have as much as possible. When I got to the humongous mushroom head I opened my mouth wide and took his head in my mouth. I started bobbing up and down on him slow at first but the slut in me wanted more so I went faster. Licking and sucking louder and louder. Suddenly a light was turned on and I realized someone else was in the room with us. I didn’t seem to care as I kept going. Brad was breathing heavily as Tammy walked up to us completely naked and started to kiss Brad.
I didn’t know it was Tammy until she took her place beside me and sucked his massive balls. I had about half of Brad’s cock down my throat and I didn’t want to share. Tammy got around back of Brad and pushed him forward causing me to lay back with my head tilted back. Brad now had to fuck my mouth as Tammy gave him a rim job.
Brad really like this and fucked my mouth harder and harder. He grunted and shot what felt like gallons of cum down my throat.
Pulling his cock from my throat and licked my lips.
Fuck that was awesome he said, no one has ever taken all of my dick at once.
I wiggled out from under him and bent over the bed. Brad needed no other hint as he ripped a hole in my pantyhose. Tammy applyed a huge amount of lube and then layed under me and started to suck my cock. Brad steped up and slowly pushed his massive head in my ass. The lube helped a lot but fuck did it hurt bad. I came in Tammy’s mouth but she didn’t stop. Brad held still with just the head in for a long time. Tammy was stroking his cock as she sucked me. My head was spinning.
Slowly at first Brad started to cut into me small strokes at first. Then deeper and deeper. My eyes were closed. I came again into Tammy’s mouth. Again she didn’t stop. Faster and deeper Brad fucked. Finally he was balls deep, he held there for a minute allowing me to get used to his girth and length. Brad reached down pulling me up to him, forcing me to arch my back hard. I turned my head and we kissed. Tammy was still sucking my somewhat soft cock. When Brad stopped kissing me I opened my eyes to see a large black cock pointed at me I grabbed him with my left hand and slammed my mouth down on him. Swallowing him in one fast gulp.
Brad pulled almost all the way out and slammed into me hard cousing me to lurch forward on to the black cock and slamming my little dick into Tammy’s mouth. She slid out from under us and sat on the black guys face.
We got into quite the rhythm fucking and sucking for quite a while. The black guy pulled his meat from my face and Tammy quickly sat on it reverse cowgirl style. Tammy and I kissed as we both got royally fucked. I was cumming buckets but I didn’t touch myself at all.
Brad pulled me to him as he lyed Down, I was riding him now. Gawd what a feeling. To take as much or as little as I wanted. I wound rise up until his cock would just exit me then slam back all the way down. Brad saw my dick and gave it a tug or three but I kept sliding in him until he came in my ass.
He spun me around and layed me on the floor without taking his cock from me. He raised my legs up to his broad shoulders. I rested them there as he made tender love to me. Long deep tender strokes. I could hear Tammy grunting like mad.
Brad fucked me like that for the next hour. Then he filled me again with his seed. Tammy and her friend we’re fast asleep when we got up.
Brad handed me as he got up a large buttplug. I turned around and he pushed it in. It was bigger then Brad so it was snug.
I kissed him and gave him my phone number as we left the bedroom.
He programmed it into his cell phone and my name came up. Puzzled he looked at me and said Todd ? I smiled and said yep. And just so you know you are my first man I ever let fuck me.
He smiled and said I’ve wanted your sweet ass ever since grade 9.
On the way home I needed gas so I stopped at a service station and filled up. Then I realized I didn’t have any money. I walked into the store and the guy at the counter was the same guy at the goth store.
Well you look like your night was full filling he said.
You could say that I respond.
I’ve got a problem. I just filled up and I don’t have any money with me. Can I go get some to pay you with ?
He looks me up and down and says you must have something I want ?
I flashed him a grill and asked him what he had in mind.
Come around this side of the counter and give me a blowjob. I was on my knees in no time. He smelled awful. Like he hadn’t bathed in a week. But I didn’t care.
When the door opened and a state trooper came in I thought I was in deep shit. I just kept sucking. He looked around for a few minutes and came to the counter. Kinda a slow night hay, he says. Ya, slow that’s right. He rang up the sale and bagged the purchase. Who’s car is at the pumps he asked. Some broad had left her money at home. She started walking home to get it.
Oh, I see he said as he paid. Then left.
I sucked harder and as the door shut he grunted and cumed in my mouth.
I stood up and thanked him and left.
I didn’t get very far when the state trooper pulled me over. I rolled down my window and asked what the problem was.
He said I saw you in the mirror behind the counter sucking that guy off !
So what I say. We worked out a small problem I had.
Ya, no money for gas so I’m guessing you have no money now ?
No sir, I don’t.
And what about ID ?
No sir I don’t have my ID either.
So is this car stolen ?
No, of course not !
Who’s car is it ?
Mine and my wife’s !
Step out of the car please !
Why ? What did I do ?
Step out of the car please he repeated !
I stepped out and he asked me to put my hands on the trunk.
I did as he asked.
He frisked me. Then he steps back and says your a man.
Yes sir I am. I just left a Halloween party.
I’m gonna let you off with a warning this time. Make sure you carry your ID and always keep some money on you. Now get outta here.
Yes sir I say and I left. I got home to find Carol asleep. It was 5:30 am after all. I was so tired I didn’t get undressed, I just layed down and fell asleep.
When I woke up Carol was standing over me. I was face down. What is that Todd ? She asked.
What’s what I ask.
What is in your back side ?
Oh, that’s a but plug.
What’s it doing there ?

Well that’s another story !

Please give me feedback good or bad. I’m trying to see if I can be a writer. I know I need to work at it.
Thank you

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