tagAnalThe Winning Halloween Costume

The Winning Halloween Costume

byRickyroma©

Halloween fate brings an anal hungry coed her fantasy

Terry looked over her shoulder at her butt in the mirror turning it side to side and said to Anna, "Do you really think wearing a G-string will make a difference?"

Anna was her long time loyal roommate. They had both been at the college together for three years now. Anna giggled, "Listen, if he is at all interested in anal sex, this will definitely push him over the edge. Look, either he is a butt man or he isn't. Face it, most guys are boob men. Finding a butt man can sometimes take a while. Frankly, I'm surprised that a gal with a butt like yours has not already attracted several butt men."

"What do you mean a butt like mine?" asked Terry.

Anna stood next to Terry and explained, "Look, my butt is just a butt, nothing special. Yours is rounder and firmer and kind of pokes out in the back. Here turn sideways. See what I mean?" Terry's butt stuck out easily twice as far as Anna's. "Guys who are into butts, into anal sex, that is what they are looking for. It doesn't matter if you are wearing a G-string or a potato sack, they can spot it a mile away."

Terry continued to look at herself and replied, "So do you think Jim just isn't into butts, and that's why he never tries anal? I mean I have come right out and asked for it and he just kind of shrugs his shoulders."

Anna giggled, "Well if there is any interest at all, showing him that G-string will do it." Terry hoped it would do the trick. She would be with Jim all night, and she knew there would be an opportunity for him to see the G-string and, just maybe an opportunity to try anal sex. She even picked a costume that might create that opportunity.

"So tell me again about what it is like to have a man pounding your ass" Terry asked.

Anna propped herself up on the bed and spoke in a slow delicate way, "Well, at first it is kind of scary. You feel this slippery, wet, fleshy knob pressing from behind. You are not sure if it is better to clench your anus shut, or to try to kind of push like you are going to the bathroom. Either way, it starts to enter and it really is kind of shocking at first."

Terry winced and grasped her bottom and said," Oh my God, then what?"

Anna continued," Well then when it first goes in it kind of feels like gravel all rough and scratchy. Even with tons of lube. But the guy will just start humping away. In your mind you are in a panic because it really does hurt."

Terry quickly asked," So then what do you do?"

Anna continued," So then you decide to try to push out while it is going in and then it starts to move easier. You realize the trick is to always be pushing out. It relaxes everything inside and then you can take the penis in really deep. But also your clitoris begins to throb and your pussy quivers so it kind of feels erotic, and you brain starts to relax. And it feels amazing at that point. You just give into it and go with it. You no longer care if it is messy or naughty, you are getting ass fucked now."

"Wow that sounds incredible. So do you end up having an orgasm?" Terry asked.

Anna replied, "Oh yes, the most fantastic kind. Your body just turns into one big orgasm from head to toe. But that's not all."

"What" asked Terry?

"Well after your orgasm, the guy still wants to go for it. He's still got plenty of steam going. So now you are in for the ride!" explained Anna.

Terry asked curiously, "So what do you do?"

Anna smiled, "You really only have one choice, take it. I reach back and spread my ass cheeks and push back against the thrusting because when they go as deep and hard as they want they finish quicker. But other times I just put my hand down onto my clitoris and masturbate because having another orgasm is really easy when a guy is pounding your ass. It is just so intense."

Terry closed her eyes and drew in a big breath of air. She moaned, "Wow, I really hope he goes for it. I get butterflies in my tummy just imagining it. "

Terry put on her sweatpants and started putting on her make-up. She and Jim were going to the Halloween party on campus. They were both in drama class together and had made a special costume for the party. The professor told the class that if they won the Halloween costume contest they would get an automatic A in the class.

As Jim and Terry had been working together on the costume they had become somewhat of an item. Jim was a cute guy but he just didn't seem to have very good sexual instincts. They had made out many times and even progressed to having sex a few times. But Jim was very timid and calculated. Terry wished he would be more adventurous. In particular she craved anal sex.

She had read about it in one of her health classes and from that minute she had been obsessed with the idea of it. She went on line and looked at some video clips of women taking it in the ass. It gave her butterflies in her tummy just imagining it. Late at night she would take the handle of her hairbrush, rub hand lotion on it and slowly insert it into her tight ass while she masturbated. It made her feel so naughty. The orgasms were spectacular.

A few times she looked for something larger, more along the lines of a man's penis. She wanted to know for sure what that would feel like. She bought a sausage at the grocery store that seemed the right size, but when she tried it was too soft to penetrate her tight ass. When she pressed hard it just bent in two and broke in half. Then she tried a small cucumber, but that time she used her hairbrush handle first to loosen things up. The cucumber went in and it hurt, but at least she knew she could take something the size of a man's penis. Now she just had to find the right man.

In a dorm not too far away, Rick was in the bathroom of his dorm room apartment looking in the mirror putting the finishing touches on his Halloween costume. Rick was looking forward to the Halloween party but at the same time he felt overwhelmed. He was not very good in a crowd. His mind always had many thoughts but it was difficult for him to articulate what he wanted to say. It always seemed like he would think of just the right thing to say a minute too late. He almost dreaded being in crowds, envying those who could be the center of attention. Most often, he would shrink into some corner somewhere and just watch everyone else having fun.

The only thing that made Rick want to go to the Halloween party was Terry. She was the apple of his eye. To him everything about her was perfect. Terry was the gal in his college chemistry class that sat two seats in front of him one row to the left. She had thick red shoulder length hair, blue eyes, and ruby red lips. But the one thing Rick liked most about Terry was her firm round ass.

Rick would sit in chemistry class and stare at Terry's ass. He was mesmerized. There was no angle that did not look fantastic. Seeing her from the front, the side or the back it didn't matter her perfectly shaped ass had the right curves. Some people might think she had a fat bottom. Some might say it protruded out too far, or that her hips were too wide, but not Rick. His favorite thing to see was when Terry would stop taking notes and stretch her arms up over her head arching her back. Rick would drink in the visual image of those amazing curves, Terry's small perky breasts straining against her blouse, her small waist curved back, and those luscious buttocks perching back. Often he would fanaticize about what it would feel like to have Terry perching those buttocks in the exact same way pressing them back against his crotch.

Sometimes Terry would be wearing a sweater and decide to remove it, pulling it up and over her head. Rick loved this most of all because he would often get a glimpse of her bare skin on the small of her back. Her shirt would come up slightly exposing the small patch of skin. Her skin was so delicate and fair. When he would try to imagine her naked he could hardly stand it. Imagining her luscious bottom without any clothing at all was more than he could take.

One time when Rick was staring at Terry's ass in chemistry class, he was imagining Terry naked and on her knees, bent over a couch looking over her shoulder at him with her ass exposed. He could imagine her firm round buttocks, her white creamy skin. He imagined himself kneeling behind her and pressing his throbbing penis against her tiny pink anus. While he was fanaticizing, he could not help but reach his hand down into his pants to carefully, secretly stroke his penis. It only took a half a dozen strokes and he lost it in his underpants. The guy in the row next to him looked over at Rick with suspicion. Rick knew it was risky but he just couldn't help himself.

Often, too often, Rick would be staring right at Terry's ass when she would turn back and notice. He would quickly look up at her and then away. He never knew what she must be thinking. Of course he assumed that she must be thinking he was a pervert or something. He tried to be careful, and make sure she was looking forward, but even so he would frequently get caught by her.

Rick put some rubber cement on the comically large mustache and then placed it on his upper lip completing his Yosemite Sam costume. He looked in the mirror at himself and said in his best cartoon voice, "Dead Rabbits tell no tales!"

Rick had a strategy. Last year Terry wore a bunny costume to the party, so he was hopeful that maybe she would be a bunny again this year. Dressing up like Yosemite Sam he figured could pretend to hunt Terry. It might give him a reason to actually talk to her. Last year at the Halloween party was the first time he ever saw her. Her bunny costume was just a bit too small for her firm round ass. She kept reaching back behind her and pulling it down over her slightly exposed buttocks. Rick kept positioning himself to get a good vantage point to see her from the back. When Terry would dance around a bit the leotard would work its way between her firm, round ass cheeks exposing those luscious buttocks. Rick forgot what planet he was on. His buddy and roommate, Jason, had figured out what was captivating Rick's attention and quickly accused Rick of liking the chick with the big ass. So a whole year had passed with Jason chiding Rick about it every chance he got. Even with that added pressure, Rick had still never talked to Terry. He was mesmerized by her while at the same time he was terrified to speak to her.

"Dude! You look like you just came off a Greyhound bus from Montana!" Jason barked from the other room. "What are you? Some kind of bronco buster? "

Rick turned to face his roommate pulling out the toy guns in his holsters, "Stick um up you lily livered snake!"

Jason put his hands up and laughed, "Dude, seriously you look like some kind of redneck. Not saying there is anything wrong with that. Some chicks dig that redneck attitude."

Rick kicked the couch, "No man, I'm supposed to be Yosemite Sam!"

Jason straightened out his John Belushi Toga and put his flip flops on, "No way Dude, you are just too tall and burly to ever be Yosemite Sam. You look downright scary like a kick ass cowboy or something."

Rick was kind of big and burly, he was always bigger than his peers. As he was growing up there was always one or two kids that would pick fights with him. Everyone wants a piece of the big guy. That constant badgering contributed to his introverted personality. His mom used to call him soft hearted. Probably what she really meant was Rick would think carefully before he would speak making sure not to give anyone reason to get upset or pick a fight with him.

Rick and Jason walked into the gymnasium where the campus Halloween party was already underway. There were all the typical costumes, Witches, Zombies, and a few character costumes, Pirates, and of course bunnies. Rick scanned the gymnasium to see if he could find Terry. After walking around for a while he spotted her. His face dropped.

Terry was with a guy. In fact, they were sharing the same costume. They were dressed like a prince and princess ridding on a horse. The clever costume was a white paper Mache horse covered in white canvas that had a large hole where the saddle would be. Terry and her date stood in that hole, with Terry in front.

The paper Mache horse was held at the waist by the canvas apron with a drawstring, kind of like the rubber apron of a kayak. Their real legs were indeed the horse's legs but they had white canvas leg coverings that tied just below the knee decorated with tassels to help create the illusion that their legs were the horse's legs. There were fake prince and princess legs stuffed with newspaper draped down the sides of the horse. All of this worked together to create the illusion that they were actually riding the horse.

All together, the horse costume was cleverly constructed. It really looked like a prince and princess riding a small white horse. There was no doubt this was a costume borrowed from a theatrical troupe. It was beyond the typical dime store cobbled together costume the average student would normally throw together.

There were three things about this situation that bothered Rick. First, Terry was with a guy. Second the costume completely hid her luscious ass from Rick's view. But third, and worst of all, her luscious ass was pressed against her date's crotch!! Rick's brain could not wrap around this situation, it was a major disappointment.

Jason also saw Terry and put his hand on Rick's shoulder, "Dude... see, I told you. You should have asked her out. Look at her date man! He's a total dweeb. I know that guy, he works at the bookstore. Dude, if she would go out with him, for sure she would have gone out with you. I think he's actually in the Drama Club."

Rick stood dumfounded. He had hoped so badly to find her wearing a bunny outfit like last year. Seeing Terry in this goofy team costume ruined his spirits for the night.

Jason punched Rick on the arm, "Come on Dude, there's about a thousand other gals here tonight."

Rick didn't say anything. Sure there were probably lots of other gals there tonight, but not like Terry. She just had the perfect combination for Rick. She had a perfect ass. Rick had dreamed of sliding his penis into her upturned ass many times over the past year. For some reason seeing her in her bunny outfit, seeing her perky firm round ass cheeks peeking out was going to give him the courage to approach her. Perhaps lead to his anal dream coming true. He was crushed.

Jason and Rick moved on through the crowd, meeting with friends and joking with each other. Whenever Rick would see a gal dressed like a bunny he would quickly draw his toy guns and pretend to shoot them. None of them has an ass like Terry's. A few of the gals pretended to be shot grabbing their chest and pretending to die with all the drama they could muster. Most of the gals just gave Rick a funny look and kept walking. Despite his effort, no one recognized Rick as Yosemite Sam. He was just too big and mean looking in that costume.

"Come on Rick, let's go check out the spook alley." Jason reached up and put both hands on Ricks broad shoulders and pushed him in the direction of the spook alley.

As they walked over to the spook alley a gal came up to Rick with her thumbs up and said,"Hey nice cowboy costume."

At first she didn't recognize him. Rick pulled out his toy six guns and said, "Stick em up!" The gal said, "Hey, your Rick from chemistry class... Wow, that costume makes you look... well... you look kind of like a bull rider or something." She pointed her hand at him like a gun and pretended to shoot back at him.

Rick normally just wore sweat pants and a hoodie. He wasn't much into fashion. Somehow this cowboy costume perfectly framed Rick's strong quiet personality. His dark eyebrows and tan skin went well with the theme.

Rick and Jason entered the spook alley. It was just a series of scary scenes one after another. First was a scene with zombies. The area was filled with fake smoke, and black lights lit up the zombie characters. The costumes were really convincing. One scene after another surprised them until they made their way completely through the spook alley which ended outside. They began to walk back to the entrance to the gymnasium.

When they turned the corner there was an ambulance and a small crowd gathered. Rick stood up on his tip toes to try and see what was going on. There were a few paramedics picking up a gurney and loading a student into the back of the ambulance.

Rick asked one of the students in the crowd what had happened. They told Rick that some guy started having an epileptic seizure when he went through the spook alley, something to do with the strobe lights. They said as soon as they got him out of there he was fine, but the University security insisted that he be taken to the hospital.

The crowd dispersed. Rick and Jason continued walking to the gymnasium. Students were out front goofing off in small groups. Then Rick saw something that caught his eye. Some gal was standing off the side near the parking lot by herself. The street lights were too dim for him to recognize her, but then she turned slightly and the curves became perfectly recognizable .It was Terry!! Rick stopped in his tracks.

Jason kept walking and then realized Rick was no longer by his side. He turned to look at Rick, "What now?"

Rick looked at Jason and motioned over in Terry's direction flipping his head.

Jason turned completely around, walked up to Rick, grabbed him by the collar and shook him, "Rick the God of Gals with fat asses has smiled upon you! Dude... come on, don't screw this up!"

Rick looked down at his Toga clad roommate, "Look, her ass is not fat. It's perfect, round, firm and amazing. "

"Come on, follow me, just let me do all the talking... you big ass loving lummox", Jason dragged Rick by the collar in Terry's direction.

As they approached Jason spoke, "Hey what are you doing way over here all by yourself?"

Terry responded in a crackling voice beneath sniffles, "I'm waiting for my roommate to come pick me up." Terry was standing next to the horse costume. Without the horse it was easy to see that the top half of her costume from the waist up was a princess, but the bottom half of her costume was just a pair of sweat pants. The sweat pants rode low on her waist. Even in the dim light of the streetlamp her shapely hips could be seen. Rick wondered what she might be wearing beneath those sweat pants, since she wasn't wearing them when she had the costume on.

Jason asked, "So that guy they took away in the ambulance, was he your boyfriend?"

Terry sniffled, "No he's not really my boyfriend. His name is Jim. He's in my drama class. He helped me make this costume. We were trying to win the best costume contest. We get an instant A in the drama class if we win that contest. We had been practicing walking and prancing in the costume all week."

Rick just kept staring at her sweat pants. The defined curve of her luscious buttocks emerged as she shifted her weight from one leg to the other while she talked. He could hardly breathe. Rick could not see a panty line. But as she turned slightly he swore he saw a thin neon yellow G-string peeking over the waistband of the sweatpants.

Jason continued, "Wow, that's a bummer."

Terry looked up at Rick and caught him staring at her butt. Terry laughed, "Hey I know you, and you're that guy who sits behind me in chemistry class. I didn't recognize you in that costume, but I could tell it was you because you are always staring at my fat butt in class."

Rick was mortified. He didn't even know how to respond. Was she serious? Was she just joking with him? He knew he had to say something quick, but what? He quickly drew his two pistols and shouted awkwardly, "Stick em up missy."

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byRickyroma© 14 comments/ 187398 views/ 150 favorites

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