The genesis for this story is the film "Dogfight" but the story is only very loosely based on that movie.
The "dogfight" refers to an "ugly date" contest among a group of men in which they each go out and find the ugliest female that they can, and persuade her to attend a 'party'. At the party the guy with the ugliest date wins.
- Wikipedia on the movie Dogfight.
Billy Cantwell was sitting in a quite comfortable easy chair staring at the dying embers of the fire in the large stone fireplace. Taking another sip of the hot eggnog nicely laced with brandy warmed him more than the remains of the fire. The large glass Christmas ornaments on the tree reflected myriad images of the coals now lightly coated with ashes.
Billy was troubled that night ... once more feeling the shame of that night those years ago, that night with Jenny. And the dance the next day—really a dogfight—how proud she had been when they announced the winners of what she had so naively believed a regular dance contest.
He shifted his leg slightly on the footstool trying vainly to make the phantom pain of the missing foot he had left behind in 'Nam go away. Jenny ... what had happened to her? She just disappeared; he never ran into her again. "God," he thought, "how she must hate me!"
He sensed the presence of another in the room with him. That situational awareness that came from the hell that had been the long siege of Khe Sanh was still with him—one thing he had not left behind. Yes, he knew there was a person in the room behind him, holding still ... maybe a faint smell of lilac—no smell like that in the foxholes. For some reason he was loath to simply turn and see whom it was. There was a feeling of something momentous about to happen in the air. Holding still, hardly breathing, he felt the soft touch of a hand on his shoulder.
"Hello, Billy," came the soft voice that shattered the illusions about his life he had been clinging to.
Billy Cantwell was happy! He had been a tough All-State linebacker and an All-American wrestler at Cherry Creek High School in Denver. Being a moderately good looking guy (in his own humble opinion) and smart as hell—it's not his fault he was so busy partying that he couldn't keep his grades up—and now Iowa State was going to be blessed with his athletic prowess.
The wrestling coach at ISU convinced him to concentrate on wrestling. The coach was desperate for a good competitor in the 184-pound weight class. Overriding his B- GPA was his skill in sports, his extra-curricular activities (driven by his do-gooder mom), and the fact that the Dean of Admissions had been Billy's dad's roommate at Iowa State. So Billy was at Iowa State and was going to pledge for his dad's old frat house: Zeta Eta Theta.
Billy was neither attractive nor unattractive. He did have a certain rugged handsomeness, an undeniable persona that attracted girls like a magnet, and he had a well-deserved reputation for having fun. The girls in his classes seemed to flock to him and he had more of the girls volunteering to tutor him than he could possibly use. This of course made many of the girls unhappy.
One of them, Jenny Lynne, was a somewhat plain girl from Rockford, Illinois. She wasn't really ugly but she sure wasn't getting any dates. She was a bit too tall, a bit too thin, and over-the-top too shy. But she was more than way smart and had a heart of pure gold! Still she had no dates, and less self-confidence. So from afar she adored Billy Cantwell with a passionless love that was as true and as bright as the dawn rising like a phoenix from the ashes of the night.
Billy had rushed right through pledge week. The silly initiations were meaningless and no one really wanted to mess with Billy anyway. His reputation for single minded, even ruthless aggressiveness in the ring was well known throughout the campus even though he was just a freshman.
Then on Thursday night before the pledge party on Saturday, all the new pledges were all taken to the basement of the fraternity house and sworn to secrecy. The key activity would be a dogfight or an ugly date contest. Each new pledge had one day to find a girl for his date and during the dance a committee of three would judge each girl.
At the end of the dance a presentation would be made of an appropriate sized trophy for first, second and third place. The largest trophy—the one Billy fully expected to win—was inscribed: First Place Zeta Eta Theta—Pledge Dance Contest. The winner would get a room to himself for the four years of school—beginning that night if desired (a key to the room would be quietly passed along with the trophy.
The girls, of course, were never to be made aware of what the trophies were really for but the guys would all have a great time laughing.
Now most of the pledges were frantic about finding a truly ugly girl in such short time. Once the girl had been singled out, she still had to agree to go to the dance—and the fraternity didn't have that great of a reputation around the campus. Billy wasn't worried. The president of Zeta Eta Theta, Kenny Ames, was Billy's brother's best friend and had been on the wrestling team at Cherry Creek when Billy was a freshman. Two days prior Kenny had taken him aside to have a talk with him.
After explaining about the contest, he continued, "Billy, my man, I don't want some asshole to get that room so I'm going to fix it so you win. I just ask that you find a girl that's believable. I'm counting on you, Billy!"
So Friday morning Billy started thinking about all the girls that had been sniffing around. Then it came to him—Jenny Lynne. He normally had pretty high requirements for his tutors but he was having problems with his pre-calc class and Jenny was clearly the smartest person in class. So he had broken his rule and asked her to help him out.
Her response had been almost pathetic. She had been so excited she had started stuttering. She wasn't really so bad looking, somewhat mousey, her nose was a little crooked and she didn't use any make up. Underneath her far from stylish clothes she looked like she certainly had a useful body. Unfortunately, every day was a bad hair day for Jenny. He called her and asked if she could come over to his dorm room and help him with the homework assignment.
Jenny came right over but after fifteen minutes or so, Billy called a halt, "My head is hurting too much for this today. Let's take a break."
He took a beer out of his small fridge and took a long swallow. "Here, Jenny, you finish this one and I'll get a new one."
Jenny nodded a strong no, "No ... Bil ... Billy, I don't drink!"
Billy, truly flabbergasted, stared at her, and then asked, "You mean you have never had a drink?"
"That's right, Billy; I don't like to drink."
With a smirk he handed her the can and got a new one. "If you have never had a drink, then how do you know you don't like it?" he said in a forceful tone. "Now be sociable and drink with me."
With that he held the can to her lips and tipped it up so she would have to drink or make a mess. He tipped the can higher and higher until it was empty while he drank his own beer in one long gulp.
"Now that wasn't so bad, was it? And just what else have you never done?" Billy asked, not giving her time to respond. "Here's another beer. Let's have fun."
Jenny was confused and a little fearful. Then she realized that Billy, the boy she loved with all her heart, wanted to have fun with her. She took the can and tried to stay up with him as they drank several more cans. During this Billy had started holding her hands and then put his hand on her knee whenever he made a point.
Leaving his hand on her knee, he said, "Jenny, I think I like you a lot. Could I kiss you?" With that he gave her a long, but somewhat chaste kiss, and slid his hand up a little higher on her leg.
Jenny tensed and grabbed his hand.
"Jenny, Jenny, I guess you don't like me," Billy said as he backed off a little.
Jenny was confused and more than a little tipsy from the beer. "No, Billy. I mean yes, it's all right," she blurted as she turned red and leaned into Billy and gave him what she understood was a passionate kiss.
Billy wasn't going to pass this up. He quickly removed her blouse and bra and started kissing her firm and larger than expected breasts.
By now Jenny was on fire and lost in the passion of the moment. As Billy took her skirt and panties off she offered no resistance ... she even lifted her hips to allow him to get the panties off.
Billy dropped lower, kissing her stomach, nuzzling her navel. Moving quickly he spread her legs a little and started licking between them.
Jenny was lost in the moment and quickly had her first orgasm as Billy went on to take her virginity.
The next morning Jenny was awakened as Billy entered her from behind. She was dry but Billy ignored her faint protests and quickly ejaculated in her.
Later, after they had showered and Billy had shown her how to go down on him, Billy told her, "Jenny, I guess you are my girl now. I'm taking you to a dance tonight so everyone can see you."
"Oh, Billy, you have made me so happy. I've loved you since the first time I saw you." Jenny blushed big time as she said this.
"One thing, Jenny. This is like a costume party. Come by here at six tonight and I'll have some clothes for you. Now don't forget, you are my girl." With that Billy gave her a big kiss and edged her out the door, a smirk not seen by Jenny on his face.
Jenny did come back to Billy's room promptly at six. Billy handed her a bag and told her to put the clothes on.
.... There is more of this story ...