This is halloween!! A day that everyone goes out and dresses up in costumes and other things, and go to parties and drink and show off their wild side until the wee hours of the next day. And I thought to myself, since everyone goes out and wears costumes, why not dress up myself into something wild and willy?? Or in fact, why not dress up in a manner of expressing who I am and what I feel inside??
That gave me a great idea. While I am still 16 and seeing many older men getting off on younger boys and girls before they reach adulthood, I thought I should be the wild girl I am inside and express that on halloween night just to see how lucky I get that night. So, without missing a beat, I went out shopping at thrift stores and look for skirts, blouses and high heels that look sexy enough to wear. While shopping at a nearby goodwill store, I found a mini pleated navy blue skirt that was about mid thigh length, so when I bend over, I could give the guys a good upskirt view of my white shiny silky thong panties that I will wear underneath my skirt.
next, I found a good black thick turtleneck women’s sweater, it doesn’t cover my lower back so much, but I didn’t care, I loved the way it looked. next, I found a pair of nice black high heel pumps. I don’t like anything that are open toed, so I found some very nice and sexy shiny closed toed heels with an elastic band on the ankles so that my shoes don’t fall off.
in total, I spent about 9 dollars. so that still left me with enough money to buy a girly wig at a nearby discount store. and I found the most perfect brunette wig that goes straight down but slightly curves up at the tips, and my favorite part of the wig was that it had long bangs that would cover my eyes, so that I don’t really see the guy who will fuck me, that’s if I get a guy to fuck me and doesn’t freak out that I am a guy dressed in chick’s clothes.
then I went to buy make up. I got red lipgloss that stays on my mouth and won’t smudge, and some eye shadow and some powdered foundation to hide my 5 o’clock shadow that was starting to creep up on me so young. I didn’t worry about mascara because a lot of girls complement me on how full and thick my lashes look, even in jealousy they complement me on that. how cute 🙂
So, it was getting dark, the sun was setting, so I go to this community college located near the mall, and I go to the locker room to change up. luckilly no one was in the locker room after 6pm even though they stay open until 10pm since there are other p.e, classes in session that require the use of the lockers. Anyway, the college is where I met the horny old man that fucked me for the first time, where he fucked me underneath the bushes on my knees rocking on the lazyboy chair. in a way, I hoped to meet him if he was there to see if he could give me a good deep one before I get any more guys to fuck me. but I thought, not yet, maybe later at night after I had enough fun.
Funny that I brought some alcoholic drinks with me that a friend gave me to drink if I ever go to any of the parties, so, I decided to drink 2 canned long island iced teas before I turn on the shower, so that I can feel ready to go. Well, while I take a warm shower, shave off any hairs that are growing so that I stay smooth, suddenly, I felt the alcohol kick in too fast, and I quickly got horny while in the shower.. of course for my protection, since I don’t want to be caught naked, I had on a black nylon thong, and the thong was starting to shrink on my bulge because of the warmth of the water. this got me hard, and got me to lean on the wall of the shower while I stand on my toes and arch my butt upwards. I was really feeling sexy. I noticed the shower has a water setting that can go from full coverage to a simple but strong jet massage stream, so without thinking twice, I set the shower head to jet stream, and the water came pulsing out so fast that it started to hit my butt cheek. it turned me on. so, I dediced to lay on the floor of the shower and arch my ass up as the water came streaming down really hard. the water felt so warm and the hardness of the waterflow got my cock harder than ever. so I started to set the water temperature a little warmer, but not too hot. this made me want to set it a little warmer still, and..wooooow…it felt sooooooooo good!! so good, that I began humping my cock up and down on the floor while I had my thong on, and my thong was still getting smaller and smaller from the temp of the water, this put pressure on my hole, and I just couldn’t help myself. I began to moan softly until a few more humps on the floor and I came so much on my thong. it felt wonderful being drunk, wet, and extremely horny. then, the lights turned off. and I heard footsteps. I couldn’t see anything. then I heard the footsteps get closer, which actually got me hornier than before.
And then, I heard a voice of an older black man saying “you sounded sexy little boy. you still horny?”
“Yes, I am”, I said in my somewhat girlish voice that I had tried practicing on my own. “what would you like me to do to you??”
“just bend over and let me fuck your hole. i’ve been watching you how sexy you look in that thong, so I just wanna fuck you with it on!”
While still on the floor with my ass arched, and the water running, he took off his clothes, and then set the water setting back to full, but kept the water really warm. then he came up behind me, both of his hands grabbing on to my hips, and began rubbing his thick cock. it felt thicker than my fuck buddy’s. in a way, I was kind of getting worried.
“you like how my cock is rubbing up on your ass?” he asked
i replied with a soft moan and then began to move up the pace of my ass rubbing his thick dick.
have you ever gotten fucked by a guy before?, he then asked.
I lied to him by saying “no”. it’s not like he will know or anything. “by the way, I hope you like 50 year old men, cuz you look really young. I like em young.” he said. I told him I was sixteen, and that’s when he moved my thong to the side, and then placed his already gooey cockhead on my hole and said in my ear: “trick or treat, baby, tonight’s your lucky night. imma make sure you enjoy this treat deep inside you real good.”
“just fuck me now!” I said.
then I felt his cock sliding inside me so easy, yet with pain, because he was very thick! I began to clinch my hole, and told me not to fight it. after a few minutes, I felt my butt soften and had to drink another canned long island tea to get the mood going.
this got me pretty damn tipsy, after already drinking 2 of these earlier.
i felt him going deeper in me as he was holding my hips with his hot thick hands. I loved how he was grabbing my hips. it felt so sexy. suddenly after 3 minutes, he began to pump a little faster, and I was starting to moan loud “oooooooh, fuck me! come inside me now baby!! please cum in me!! cum in me now!!”
this got his cock thicker, which only meant one thing…and this got me to also pump his cock a bit quicker on him, and without holding back, his cock swelled inside me and I felt him shoot cannon loads of his creamy sauce deep in my lusty horny cunt! I never felt a guy shoot that much cum in my life!! I wanted him to fuck me forever. after he came inside me, I pumped him still until he softened and then slapped my ass, making me moan as he pulled out. I loooooooooooooved how much he came in me!! after that, he got dressed and left. I hope to feel him again soon. so, without wasting time, I got back to cleaning myself off, and then the lights came back up. I felt so great sexually, and also still pretty tipsy from the drinks I had while he fucked me so good.
So, I got dried up,,.then went to the mirror and changed into my “costume” bit by bit. first came my thong, I got an XS size lycra stretch thong, white color. I like this thong because I can easily tuck my cock in so it looks like I don’t have a cock at all. it holds my cock in well. But before I put it on, I needed to cut a big enough slit on the thin part of my thong so that if the moment came, then the guy can just slip his cock through the panties and fuck me from behind while he’s grabbing me my hips. I so love being fucked that way everytime. After I cut a hole, I put my thong on, making sure the hole I cut was hidden. I felt nice and sexy on me. Then came the bra, which I stuffed myself with some small socks, making sure it looked about right on each side of the bra. then the turtleneck sweater, and thank goodness I needed the sweater. it was getting rather chilly already, so it served its purpose. also, it covered up my adam’s apple, which would have given it away, really. then came my make up…applied my foundation, making sure it covered all over my neck and face, so that none of my “shadow” is visible. then came the lipgloss, and concealed it with a shiny protectant on my lips, then applied the toner on my foundation, then the eyeshadow, and just a touch of perfume. Then came the brunette wig, and finished it off with a pair of sunglasses, just to cover my eyes in case anyone I knew saw me. I didn’t want to be seen by those I know. Then came the skirt, and then the high heels, and wow!! I was ready. But after looking at myself, I forgot one thing. how was it gonna look from under my skirt?? so I bent down a little to see how much would show. To my surprise, the crotch part of my thong was visible enough, and luckily my cock and balls were NOT visible, as my cock was very well tucked in. Wow, I was already getting wet and hot with anticipation to see if i’d get lucky tonight. Now, off to parade out in the campus quad and to see if I could get lucky,
Fortunately, it was about 7pm, and the quad was already empty, except for a few other students who were planning what to do and where to go and drink and things like that. As I was scoping them out, I decided to sit in a concrete bench in the middle of the quad, which is the most visible area, where you can find just about anyone you know, which was still a problem because I didn’t want anyone I know to catch me out. As I sat down, not realising how short my skirt was, my butt cheeks touched the concrete and DAMN, that felt chilly. but I managed. Then I crossed my legs, hoping someone I don’t know would take notice, and pulled out a cigarette and lit it up.
Then I hear a voice from behind me
“Hey, baby! Got a light?”
I just handed him the lighter as he lit his stoke. Then he took a good look at me and said, “Oh, pssshhh, sorry dude, I thought you was a girl. my bad”
“It’s alright. you wouldn’t be the first to make that mistake tonight. It’s halloween after all.”, I replied.
“Haha, thanks.” and walked off.
Luckilly he wasn’t my type. He looked too young for me. I hoped someone much older would notice me. And he did.
“Hey there. I just heard you talk to that guy. he was asking if I had a light too, and then we started checking you out because we thought you were a girl”, he told me. I just giggled and told him not to worry. Then he sat down and started chatting me up, as if he really liked the fact that I looked hot as a girl. In a way, this made me feel hot and wanting of him to fuck me now. He looked handsome and old, just how I love my men. He was black, had a ponytail, average build, clean shaved and all,
“So, can I let you in on a little secret?”, he asked, as if I didn’t know what he was gonna ask me, and I was right about that.
“Go ahead”
“I love guys who dress like chicks, I always fuck crossdressers on the first night.”
I wanted to melt so badly. I really needed this guy to fuck me here and now!! But I had to keep my cool and chat back to him: “Wow, that’s cool. so, did you think I was a crossdresser?? It’s ok if you thought so.”
“Well, are you?”
“Yes, I am. At least, I am new at this. This is the first time I dressed up as a girl in public”, I told him, which was also true. I never imagined I’d do this out in public, let alone on a day when everyone wears costumes.
“Well, baby, if it’s ok with you, I want to make this your lucky night”, he said, as he lowered his hand onto my left thigh, softly caressing my smooth thigh, sending shivers down my cock, already feeling the precum soak onto my thong.
He made sure no one looked, and then lowered his head onto my thigh and began massaging his lips on my thigh, sending more rushes of adrenalin to my heart. Damn, it felt good the way he was doing that on my thigh!! And not to give out any attention, I moaned quietly as I was patting his head while he was lip massaging my thigh, and then started to tickle my thigh discreetly with his tongue. This made me nearly shudder in a wave of euphoric desire. WOW, I thought to myself, I can’t believe this feels so good. Do girls really love this?? I really started to feel more like a girl than a guy for sure.
He asked me “have you ever been fucked by a guy before?”
“Um…yeah I have actually. not too long ago. He thought I had a cute butt and wanted me to wear his wife’s panties and fucked me with them on.”
He then put his already warm hand under my skirt, feeling up from my thigh to my butt, and he was surprised to know I had a thong on.
“Oh, baby, you got a thong on! can I fuck you with your thong on?? can I fuck you in a bathroom or something?? I just gotta put my cock in you until I fill you all up inside you!”
WOW, this guy was serious!! I put my hand on his already hard throbbing fuckstick, massaging it so sensually!! damn, his dick is the hardest i’ve ever felt…and the hardest I was about to have in me!!
I leaned and whispered in his ear: “Fuck me baby. fuck me somewhere secluded from here.” and then licked his earlobe with the tip of my tongue, which sent him flying.
He took my hand, and took me to this empty locker room located in the restaurant building next to the quad. no one was there, and it really seemed safe and away from sight.
As he started stripping, I grabbed 2 more cans of long island iced tea, and this time I just downed the entire cans. I wanted the alcohol to kick in fast…which it did! NOW I was ready! He pulled his pants down and there it was, a really thick black cock, about 8 inches, and it really looked fat, and with a lot of precum seeping out from him. I hope it won’t hurt me after it’s all over. Without warning, I went on top of a bench inside the locker room, and got on my knees, while stroking his cock, I grabbed it and let my tongue go straight for his cock, licking the precum, and then taking it in my mouth little by little. And it’s funny because I never sucked cock before. His was my first, and it really tasted good. I began to bob my head back and forth slowly, making sure he enjoys what my mouth and tongue could offer. He looked so wonderfully relieved and excited just noticing how strange he was by making his eyes go in the back of his eyelids. I started making popping sounds as I started to pump his cock a little faster with my mouth!! Wow, baby. you trannies and crossdressers sure know how to please a man!! that’s why I love getting it from you!!”
I took his cock out of my mouth for a minute just to say thanks, and returned to pumping him more.
He lowered his hand and flipped my skirt up over my butt to expose my butt and the thong I had on. there was a mirror behind me, so he got a great view of my ass while he began to caress it. and then, he did something that got me really wild. He grabbed the middle part of the waistband on the back of my thong and gave it a good tug, making me spread my thighs in enjoyment, and letting out a slight moan to let him know I love it. And he tugged my thong again up my butt, and again, and again…making me shake my ass making him do it more and more, and increasing my moans, and increasing the speed of my pumping his cock with my mouth. It was getting harder still, and then while still in my mouth, I started to rub the underside of his cock with my tongue in a very passionate way that made him stop me from sucking him further.
“Baby, I don’t know what you were just doing there, but I was just about to cum in your mouth. no tranny or cd or even a woman has ever done that to me!! I gotta fuck you now while i’m still hard!!”
So, while bent over, he found a hole on my thong, and just slipped his stick through it and then started to slowly put it inside me. I was already beginning to feel queezy and sexy so much from all that booze!! I was in heaven!! I needed him to cum inside me!! It seemed like he was able to get as much of himself in, and great for that since there was still some cum left from the last guy who fucked me good in the gym shower earlier in the evening.
I started to arch my butt, trying to not hurt myself, but I was trying to push more of his cock as deep inside me as I could take. then he grabbed my hips, and started to fuck me like a wild man, starting to make me moan so loud that I loved how he was fucking me!! I needed him so badly inside me!! I wanted him to shoot his cum NOW!! I wanted him to stay inside me and fuck me forever!!
“OH MY GOSH!! PLEASE, FUCK ME!! FUCK ME!!! OH, BABY PLEASE FUCK ME!! I LOVE HOW YOU FUCK ME!! DON’T STOP!! DON’T STOP UNTIL YOU CUM INSIDE ME!!
This made him get THICKER AND THICKER inside me!! Damn, I need his cum in me NOW!! I was at the point of no return! As he hit my organ really hard, he made me cum so violently and I began to scream so loudly for him to lust me so deep!! I never felt this good IN MY LIFE!!!
OH BABY!!! YOUR ASS LOOKS SO SEXY IN YOUR THONG!! I GOTTA HAVE YOU ALL TO MYSELF TONIGHT!! PLEASE CAN I KEEP YOU UNTIL THE MORNING?? I WANNA CUM INSIDE YOU SO MUCH UNTIL THE MORNING!! just what he was saying made me arch my ass up higher so he could fuck me deeper. he responded by stabbing his cock harder into my ass. I started to moan so loud, not holding back the loudness of my sexual desire any longer!! He grabbed my hips so strongly, hitting my organ with his cock hard again that this sent me to the curve again, and then I came a second time…
I let out a long and loud “Oooh!” after he hit my organ. I began to sound hoarse from all that hard and lustful moaning coming out of me. I continued begging him: MORE!! PLEASE CUM INSIDE ME!! I NEED YOU TO FILL ME UP NOW!! OH BABY FUCK YOUR NASTY LITTLE TEENAGE SLUT!!”
Before he came, he forgot to ask me one question “BABY, HOW OLD ARE YOU BY THE WAY??!!”
“I’M 16!!!”
“16?!?!?! WOW, WHAT A DREAM COME TRUE!! YOU’RE MY FIRST TEENAGER!!”
“SHUT UP AND PLEASE CUM INSIDE ME!!!” I demanded him.
“BABYDOLL, YOU’RE GETTIN’ AN “A” FOR HOW GOOD A SLUT YOU ARE!! HERE I COME!!!
And that’s when his hardness swelled inside me so damn thick, and I felt his cock vibrate as he shot BUCKETS AND BUCKETS of his cum so deep inside me!!! He started to kiss my neck, and tickle it with his tongue, and giving me another tug of my thong while he was still inside me!!
“WOW, your cock feels SO good!!” and as I said that, I teased him by bumping my ass with cock inside me a few times to get him to want me more.
“So, baby, you wanna cum and let me fuck you good tonight?” I promise I’ll cum in you a lot more than tonight!!”
“Ok,” I said. I’ll let you take me again!”
Then, he pulled out, and damn, my ass was leaking so much from all the cum this guy had to drain out of his body! I’m glad that all of it went inside me. Soon after, I cleaned my butt, put on another thong I brought with me, this one also having a hole cut on the back…and we walked outside the room hoping nobody would suspect how kinky our fucking was inside the room. I promised to wait for him after he got done talking to a classmate of his. then he flipped my skirt up, and gave me a kiss on the butt and then a good slap which made my butt jiggle and made me moan. Then gave me a pinch and left to go see his classmate.
I went back to the quad and sat down again, a little uncomfortable from the magnificent fuck my new friend gave me. Afterwards, another man noticed me and asked me if I was gay or a tranny or whatever. He was a white guy, about 40 to 50 years old, skinnier and had a goatee. I told him i’m just a crossdresser for halloween.
“How old are you by the way??”, he asked
“I’m 16. is that ok?”
“That’s wonderful. i’m sure you get fucked my much older men because of how young you are, huh?”
I nodded “yes”
“You got a sexy way of walking for a boy. you doing anything right now?”
“Nothing really, why?”
“Well, you’re a crossdresser, right? Have you gotten fucked lately??”
“Yeah, I have,”, I replied. “but if you want to fuck me, just say you want to”
Then he came up behind me, and slightly lifted my skirt, feeling his cold hands on my buttcheeks, feeling him breathe out from his nose, and started kissing my neck, saying “i got some time now before I see my wife. she’s about to get out of class in 20 minutes. in the mood for a quickie?”
I pressed my sexy ass onto his thick tool that’s bulging from under his jeans, and said to him “only if you promise to cum inside me”
“C’mon. I know a place here in campus where I can fuck you!” So he took me to an empty classroom inside the humanities building. it was an lecture hall, and inside the lecture hall, there was a door that led to an underground basement. since his wife was taking a class in that same building, he felt more at ease and confident he could let his frustration out inside me. There was a couch there, so he made me get on my knees and arch a little, keeping my ass out, and then he put some lube on, and then found the hole on my spare thong, and began slipping it inside my butt without any struggle.
Knowing we were in a room where our voices could probably be heard if we were to ever get loud, I decided to keep my moans very low and soft, but sexy enough to get him off in me.
“wow, your cock feels so nice and small. I love that!!”
He whispered to me, “so does size matter to you, in a sense that you don’t like them so big?”
“I like them all as long as they are not HUGE!” I told him.
As he kept fucking my ass, hands grabbing my hips ever so gently, he asked me “you ready to get filled up?”
“i’m ready anytime, baby”
“damn, for a guy, you got such a wonderful ass…an ass a girl would definitely kill you for, and an ass a guy would pay to fuck anytime!!”
“wow, thank you…mmmm…cum inside me please. I want you to fill me!”
He stopped moving, his cock swelling, holding onto my hips with all his strength, then he grunted and shuddered as his cock started to vibrate inside my butt, coming really deep and hard, but still trying to keep quiet as he was grunting. I pushed my butt to make his cock go deeper in me, still feeling his cum shooting in me.
Wow, that felt really warm! And it felt really nice the way he fucked me so gently. I loved it. After I pumped him all out with my butt, he gave me a nice slap on the ass and pulled out, and got out another thong I had in my purse. I had about 20 thongs on me, all with holes on the back, just in case of an event like these were to happen. Ha, lucky me. Then, we exchanged numbers so that if he needed to fuck me again, he’ll call ahead. After that, he wanted to kiss my mouth, but I told him I never kiss guys, so instead he gave me a nice soft bite on my neck and kissed my neck all over, lifting my skirt up again, and patting my bubbly butt cheeks, and gave my thong a good soft gentle tug to make me moan and spread my legs so that he could do it some more. but what is it with guys and tugging girls’ thongs?? Then he left and gave my butt a good pinch that made me squeal.
As the night ended, I walked back to the quad, met back with my new fuck buddy that gave me the best fuck i’ve ever had!! and then I called my mom to tell her that I am gonna spend the night with my best friend, which wasn’t true. but she believed it. And so, from there, he took me to his place, and he fucked me as he had promised to. as many times as he could until the morning! Damn, he was so good to me. I loved how we even slept and woke up without even pulling out of me that whole night…and he gave me a wonderful morning fuck!! I was so in love with his cock! Afterwards, I went home, and promised I would meet him again and to just email me whenever he was ready to cum deep in me.
What a wonderful halloween night!!
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