The Damndest Affair Can Happen On Halloween


Anal, Blowjob, Cum-Swallowing, Fantasy, First-Time, Gay
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 Hallowe'en party with a bunch of people I did n'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 Hallowe'en party Sabbatum night, my girlfriend Christmas carol told me. It 's a maskarade party. We got ta get costumes.
Oh great I said. tam-o'-shanter is the rich gripe that 's been after my dick since class 9. I 'm not into her. Way to snobby for my liking.
carol on the other had is the complete opposition. Loving, lovingness and a enceinte intellect and body. trust me, I 'm one lucky guy. But she is a bit ego conscious. Do n't get me wrong, I 'm good looking and all and I am a loving, caring honest soul. I 'd never chisel on her.
What sort of costume are you thinking I ask knowing she already has a plan.
She gets this devilish smile, you know the type of grin that says she 's in the humor for sex.
She 's the predominant one in our family 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 slenderize silken body-build with chestnut chocolate-brown whisker down to just above my hips.
I just smiled and said well I guess that makes me your girl ! Not letting that sinkhole in at all.
You got that right she says.
delay, what ! Me your what ? I stammer out.
You are going as a young woman and I 'm going as a boy !
So let 's go. We 've got a few appointments to puddle it to. And out the door we went.
A short driving force later we were at the beauty salon she always goes to.
carol, it so nice to see you a gentlewoman behind the counter says. And you must be my one o'clock designation. She looked right at me as she said that.
Um ya, I guess that would be me I said. Like I said when Christmas 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 raft on the lips and said have fun and I 'll be back in a spell. 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 gon na accredit 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 steamed when I ask her what the heck am I going to to with these as I held up my manicure nails. Bright red with amber and ash grey zig zigzag on them.
carol ignored my displeasure and complemented the dame on a jod well done.
My hair was cut just below my articulatio humeri steel, styled and permed. My finger and toe nails we 're painted to match.
I have to admit, I did face pretty unspoilt. But I 'm definitely a direct guy.
Okay, let 's go. Your next appointment is only a few minutes from now.
Christmas 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 summersault flops.
We stopped at our next terminus, a beautician. Christmas carol looked at me and said just trust me truelove.
I did n't say a word. I just went in and sat in the hot seat. I saw Carol talking with the dame at the heel counter then she left.
Okay so have you ever applied makeup before she asked. I just looked at her, I did n't think so but I got ta ask, ok let 's get started she says.
Again the fourth dimension seemed to just fly by. This meter I was done before Christmas 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 piece up my boyfriend. She just pointing at me and said is that him.
Carol looked at me and for the maiden clock 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 clumsy to say the to the lowest degree. She kept stealing glances at me.
Once home we got inside and she says I got you your outfit, I 'll assist you get into it so we know everything fits.
Christmas carol has a swell eye for size. 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 typeface in no time.
I had on a white foresightful arm pullover cardigan with a slight dip to the front end neck line. A light blue tight skirt that had a cut up the center back. Black low political platform blackguard about 2"with thick bands and a buckle up on the outside. Along with a fixture beige bra and some C cup white meat human body and matching granny panties.
You like it, do n't you Lisa, she says.
looking at back at her confused I say"Lisa ”.
She smiles and says we 'll I ca n't very well address 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 did n't realise right away.
Well let 's go Lisa, we got ta 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 make a motion 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 class she got the shoes from and the Male attendant ask if he could serve us.
Yes I bought these shoes for my girlfriend Lisa here and they do n't fit I need to get a different distich 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 professorship and this guy asked me what kind of place I wanted.
Something easy to walk in I said.
She 's such a kidder Christmas 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 of it 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 clip I lifted my scummy leg up exposing my panty clad penis to the guy. He stopped all in in his tracks for a moment. As he looked me in the eye. Knowing he saw everything I said oh dear. I 'm drear, I still getting used to being a lady. He slipped the shoe on and I stood up to walk around.
Christmas carol 's smiling was gone now, instead she was just looking at me like I did something she did n't anticipate.
Carol handed the attendant my base runner 's and asked him to toss them in the codswallop. She will ware the stilettos out.
That put a smile on her fount 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 want them for.
wellspring you can hardly walk in these and boots are lower berth heel so you will be able-bodied to walk in then easier.
I tried on a yoke pairs of bang and found a couple that fit nicely. Black, very shinny with red medallion and a 5 inch heel that came down to a point.
I paid for them and expected to manoeuvre home but Christmas carol had former estimation. We stopped at a article of clothing shop and Christmas carol looked at me and said I realize now that you 're garb 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 talk of the town like that.
I followed her in the entrepot and she headed to the tike segment. She pulled a very lean 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 got covered and said here slut. Go put this on now.
I knew I 'd amend just do as she asks as she was really mad.
I got into the changing elbow 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 movement of the mirror and Christmas carol leaned in and asked me if I felt like a hussy yet.
I asked here if this was the right under garments for this rig ? She said wait right here. She headed off into the store, a male attendant aproched me with a huge grin and said wow. That looks outstanding on you. Can I aid you. I asked him what kind of under garments I should ware with this dress.
He just laughed and said that 's not a frock, it 's just a low cut t-shirt.
If your going to ware it as a dress I 'd urge some pantyhose and probably a doll of some kind.
okeh 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 panty. I came back out and looked at myself again. That 's dear I said.
Are you gon na 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 white meat human body made it wait like I had rather large teat. The low cut croped tee shirt came down to just below my waistline. And revealed almost my to the full bra. The garden pink bows we 're on the very boundary of the T-shirt. The black embroidered pantyhose had a high refulgence to them with a red grade insignia down the spine of them from my heel to my loaded little ass. carol handed me a very short silver grey shinny annulus so I slid it on. It did n't do much more the skin the waistcloth of the pantyhose. She handed me a Daniel Chester 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 bobbysock. net she put a hard worker halo on my heart finger and said I own you now !
Carol did n't go mad anymore. I was n't sure until we got home. We were walking up the paseo when she pushed me up against the tree diagram and kissed me very aggressively she reached into my pantyhose and pulled my pecker out. She pulled on it hard making me wince in pain. Then she dropped to her knees and bungle me right there.
I came quickly as this was the foremost blowjob she 's ever given me. fucking was it ever good.
She cleaned me up then pulled my pantyhose and wench back into place.
She got up and kissed me laborious 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 niggling strumpet Lisa !
audition her telephone 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 enchant I said of course.
Our dear making Sessions were usually tame, not on this night though. I truly felt like a piece of music of meat as she took me every way she could.
The side by side day, Allhallows Eve, Sabbatum we woke up after noon. So we were well rested. Hunny your physical composition is ruined, we will experience to get you an appointee to get your makeup done again.
Ok I said. I 'll go get it done, you got ta get set up. 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 cosmetician 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 phantom 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 did n't recognize me.
Are you from around here, I 'm only asking because I might be capable to help you out, if you know what I mean.
I told him I was going to Tammy 's Halloween company tonight.
sang-froid. I 'll be there. See you later he said as he stopped and I kept walking. I really was getting the knack of these heels.
I got back habitation and Christmas carol, or should I say Carl was ready to go. She was dressed as a hittman complete with a moustache 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 shortly 3 it seamed.
carol and I were nominated for best costume along with half the people there. Carol was drinking well-nigh of the night and got really pissy when I won. She left me there and took a cab home.
I stayed and mingled. I did n'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 did n't recount 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 stair and fool around.
Im not sure your girlfriend would sanction I said.
wellspring she 's not here and I 'm not gon na tell her so what do ya say. I 'm hung like a gymnastic horse you know.
I 'm not certainly what happened but when he said that I got intrigued.
A gymnastic horse you say, well I 'll demand 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 script on his human knee while I looked him back in the eye. I did n't have to move my hired hand far when I felt his cock in his pants leg. My heart got big as i realized he was n't lieing. Let 's go see this sawbuck turncock of yours I said as I got up and grabbed his hand.
Maybe it was the alcohol I had that dark, maybe it was lust but all I know is I felt so right, so intrigued, so aroused, I did n't waver 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 threshold and turned on the light. No, trun the light off I said. So he did.
The full Sun Myung Moon light was shining in through the window. He came up behind me as I was looking out and kissed my neck.
My organic structure reacted a lot different then I expected. I leaned my head teacher to the left as he kissed my right hand side of meat. I seamed to melt in his compass. He put his manus on my waist and my ass seamed to search for his crotch. He stepped nearer and slide his hands up to my fake teat. I tilted my straits back to his shoulder. He kissed my backtalk and slither his knife in my mouth. I returned his buss and let my munition hang down. I felt my way to his fork. My hands searching for his manhood. He turned me around kissing me full on my sass. My mitt move almost instinctively. As I undo his zip fastener. He slides his hired man 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 bighearted the my 6 incher but I do n't panic as I 'm literally lost in the kiss we share. I 'm still trying to liberate his prick almost feeling desperate. He steps back a half footprint and I undo his clit of his dungaree he 's a fantastic osculator I 'll hand him that.
Finally I 'm at the point in time where I can pull up his bloomers down so I break our candy kiss and slew down with his pants.
His massive dick springs up out of his pants and smasher me in the face hard.
Ouch I say as I close my eyes.
I open my optic a mo later knowing fully well his cock is mear inches from my lips. As I study his cock in the moonshine brightness level for what seamed an eternity. I finally reach out with my right hand and trace it ever so softly. Almost afrad I might break it.
Told ya did n't I, now suck it all down Brad says.
You want me to do what. I doo no. I 'm not surely I can, I mean look at how big that is.
You can do it. confidence me.
I grab him in my right field paw and as my fingers tightly try to rap around his girth I 'm forget speechless. My fingers could not close around it like they do with mine.
I do n't know why but I felt so turned on at that very mo so I closed my middle and started to lick his light beam. As my tounge made impinging with him, I felt so hungry, so dirty, so sluty. I had to let as a great deal as possible. When I got to the humongous mushroom-shaped cloud read/write head I opened my verbalize wide and took his promontory in my mouth. I started bobbing up and down on him slow up at foremost 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 did n't seem to deal as I kept going. Brad was breathing heavily as Tammy walked up to us completely naked and started to kiss Brad.
I did n't have intercourse it was tam-o'-shanter until she took her position beside me and sucked his monolithic balls. I had about one-half of Brad 's cock down my throat and I did n't want to ploughshare. Tammy got around back of Brad and pushed him forward causing me to lay back with my nous tilted back. Brad now had to jazz 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 corresponding gallons of cum down my throat.
Pulling his cock from my pharynx and licked my lips.
fucking that was awesome he said, no one has ever taken all of my dick at once.
I wiggled out from under him and knack over the bed. Brad needed no former hint as he ripped a gob in my pantyhose. tam-o'-shanter applyed a vast amount of lubricant and then layed under me and started to imbibe my cock. Brad steped up and slowly pushed his massive head in my ass. The lube helped a lot but fuck did it pain bad. I came in tammy 's oral fissure but she did n't hold back. Brad held still with just the head in for a long clock time. tammy was stroking his tool as she sucked me. My principal 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 oral cavity. Again she did n't cease. Faster and deeply Brad fucked. Finally he was balls rich, he held there for a moment allowing me to get used to his girth and duration. Brad reached down pulling me up to him, forcing me to arch my back voiceless. I turned my headspring and we kissed. Tammy was still sucking my somewhat soft cock. When Brad stopped kissing me I opened my eyes to see a bombastic 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 keel forward on to the dark peter and slamming my little tool into tammy 's mouthpiece. She slid out from under us and sat on the black guy rope face.
We got into quite the musical rhythm fucking and sucking for quite a patch. 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 bucket but I did n't match myself at all.
Brad pulled me to him as he lyed Down, I was riding him now. Gawd what a tone. To exact as much or as little as I wanted. I wound lift up until his prick would just kick the bucket 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 hammer from me. He raised my legs up to his tolerant shoulder joint. I rested them there as he made tender love to me. Long deep tender strokes. I could see tammy grunting like mad.
Brad fucked me like that for the next minute. Then he filled me again with his germ. Tammy and her friend we 're libertine gone when we got up.
Brad handed me as he got up a enceinte buttplug. I turned around and he pushed it in. It was swelled then Brad so it was snug.
I kissed him and gave him my phone identification number as we left the bedroom.
He programmed it into his prison cell phone and my epithet 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 sweetly ass ever since grade 9.
On the way place I needed gas so I stopped at a military service station and filled up. Then I realized I did n't have got any money. I walked into the store and the guy at the counterpunch was the same guy at the tike store.
Well you look like your night was full woof he said.
You could say that I respond.
I 've got a problem. I just filled up and I do n'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 accept something I want ?
I flashed him a grill and asked him what he had in mind.
Come around this side of the retort and give me a blowjob. I was on my knees in no sentence. He smelled awful. Like he had n't bathed in a week. But I did n't care.
When the threshold 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 up nighttime hay, he says. Ya, slacken that 's right. He rang up the sale and bagged the purchase. Who 's car is at the heart he asked. Some tolerant had left her money at home plate. 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 did n't get very far when the state trooper pulled me over. I rolled down my window and asked what the trouble 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 trouble 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 do n'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 ?
stone's throw 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 gon na let you off with a admonition this time. name sure you carry your ID and always preserve some money on you. Now get outta here.
Yes sir I say and I left. I got menage to rule carol asleep. It was 5:30 am after all. I was so tire out I did n'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 Sir Alexander Robertus Todd ? She asked.
What 's what I ask.
What is in your hind side ?
Oh, that 's a but plug.
What 's it doing there ?

Well that 's another story !

Please give me feedback just or bad. I 'm trying to see if I can be a writer. I know I need to crop at it.
Thank you
Sign-in {% trans 'to add this to Watch Later list' %}
{% trans 'Sign-in' %} to perform this action