A Gentleman's Wager

 

"Hey Frank! I bet you can't get into Donna Douglas's hot pink pants!"

Frank looked over at Roger and gave him a disgusted look. "Christ man! It would be like taking candy from a baby. How much you want to put on your big mouth?"

Roger Hemmings walked up to his school chum who wasn't really quite a chum. In fact, deep down inside, Roger didn't much like the super senior. Frank Timmons was one of those premier English gentlemen with the long side burns, perfectly trimmed mustache, cool blue eyes and a head of hair that would make Richard Green envious.

Young Hemmings resented this Brit who'd migrated across the Atlantic to enroll at Harvard. Why didn't the Limey stay at Oxford or Cambridge? Frank had made some snide comment like, 'Just wanted to see the world chap.' or some such inanity.

As far as a large bet was concerned, Roger came from a wealthy family so he knew his dad would understand if things didn't work out. But he figured, deep down in his gut, that this chick, Donna Douglas wouldn't give this fancy fop the right time of day. All right Frank, I'll slap five hundred bucks on the counter. I say you can't get Donna into the sack and I'll give you till Christmas to do her. That's almost the entire semester."

Frank actually snickered. "It's as good as in the bag, my lad."

That was another thing Roger hated about Frank. The supercilious bloke thought he could accomplish anything and usually did. The Brit was on his way to getting an MBA once he'd completed his Bachelor's degree in business. The man was sharp and almost always dressed to kill. What struck Roger a little odd was that Frank didn't seem to be dating anyone currently. One would have thought that this elegant Brit would be getting more ass than the common toilet.

Roger smiled with genuine malice in his dark brown eyes. "So how will you be able to prove that you've done Donna when the time comes?"

Frank thought about this. Obviously getting properly laid was usually a private thing. "Well, if I can get her to my flat, I can set up a special camera in a strategic place and record us making the beast for all posterity. Will that do?"

Roger grinned, "Hell, you might spend more on the camera than you'll win from me."

Frank chuckled, "Already have one for bird watching, don't you know. The film will only cost a few shekels. Maybe I can sell it on the net at some disreputable porn site and make a bundle. Sounds smashing, doesn't it?"

Roger gritted his teeth and thought, smashing indeed! He actually said, "I'm so sure you'll flunk out of the crash course in laying Donna Douglas that I want this bet to be witnessed by our other members in our friendly little frat, all right?"

Frank smirked and extended his hand. "Anything you say, Roger, my lad. I'll not betray the family honor for a piddling 5C note."

***

Donna Douglas was a lively, busty blonde with curves in places where many girls didn't even have places. She had a way of swaying her hips that sent shivers into many male student's dicks. She wore her hair in a fetching combination of bangs and pig tails to give her the little girl look, but she was an all American woman at age 21. She preferred wearing hot, dark nylons, four inch heels and foxy skirts that came to about two inches above her sexy knees. Her 36 d knockers always looked like they would burst from beneath the blouse or sweat shirt she invariably wore. To complete this rather juicy package, she had a tantalizing habit of occasionally licking her lips in a very seductive way. That was the startling apparition that drew males like moths to a flame. It got to the point that she could not even go to the college book store or attend a class without some stupid lunk trying to hit on her. Oh, she'd fucked around some but she hadn't met that special someone that could make her hot blood boil. She just had not seen those fireworks that her older sister, Samantha had told her about when she'd hooked up with Walter.

The problem for Donna was that she was getting so many requests for dates or what she sometimes called bed requests, that she was finding it difficult to wade through the piles of bull shit to find that glowing diamond that would change her life. The thing that interested Donna about Roger Hemmings was that he didn't ask her out. He just kind of had a way of sitting down near her at the cafeteria or the library and occasionally offer her sage advice as to who to avoid in the small world of Harvard University. Donna had known Roger for almost two years and he'd never asked her out for anything more than a cup of coffee at the local greasy spoon on Cambridge Street.

Donna found it puzzling. Roger was above average height, well-mannered and quite clean cut. He possessed an assured self-possession and was never pushy. It was as if he were doing all female kind a favor just conversing with them. His soft brown eyes, ready smile and thick, chocolate curly hair could trigger strange, tingling reactions in her own easily aroused cunny.

But it came back to the ultimate question in her intuitive mind. Why hadn't he ever gotten serious with her? Did he have a secret girl friend? Was he stuck up? Was he gay?

***

He was talking with her one morning, about a week after the fateful bet had been made with Frank. "Just wanted to tell you the latest Donna. You better avoid that Brit boy in business. I here he is a shark. And I don't mean that he just nibbles. I've heard from someone reliable that he's real smooth in public and very nasty behind closed doors. He's one of those warped Victorian type chaps who's into leather straps and such. If I were a girl I wouldn't go near the guy without an armed platoon. So how was your Romantic lit class, yesterday? Keats wasn't it?"

Donna had seen the Brit boy around. The man exuded confidence and charm but how could Roger know this man was a closet sadist? She had to admit to herself that Roger had never actually steered her wrong yet. She sipped more of her coffee. "So you think this Frank chap is bad news?"

Roger shrugged, "I'm just telling you what I heard from a lower classman or I should say woman. Maybe it's true, maybe he was a little aggressive on a date. I wouldn't know for sure because I obviously wasn't there but...."

That hanging but was Roger's most effective little weapon. He'd discovered it back in high school and had accomplished many minor turns and twists in the realm of spinning gossip only slightly the wrong way. He simply let his victim or associate fill in the blanks with their own mental images and in this case, he figured Donna was already picturing Frank whipping some poor little coed with a fancy cat and 9 tails, sporting soft leather whip ends to extend the agony.

"So Donna, you didn't tell me how you're doing in Romantic lit."

That was another subtle trick. Start talking about something else so his subject would think he had more important things to pursue than some ugly rumor. On a subconscious level, it meant that he, Roger, was so certain of the veracity of his accusation, that he didn't waste time attempting to convince. You either accepted his observation or you did not. Most of the time, people like Donna Douglas did.

Donna licked her lips in that salacious way. "That new professor, Mister James is so dreamy. I could listen to him quote Keats and Byron all day long. It's my favorite class."

Roger smiled, "I see you are really getting into your studies. What are you going into when you escape Harvard?"

Donna giggled, "Oh, either teaching or maybe into advertising. I'm not sure yet."

Roger thought to himself that she could make some serious coin by performing sex acts in front of cameras or being the display cunt for auto car commercials but he wisely held his tongue.

"Well Donna, I best be off to another boring class with Doctor Feldman. See you."

Donna procured another cup of Expresso and began to really think. One of the girls knew something about this Frank Timmons, but who? It was a large campus and there must be hundreds of girls. Perhaps she could bring up Timmons name during some female bull shit sessions in the dorm and see what hit the fan. Then her thoughts went back to Roger. Why didn't he ask her the big question? It looked like he was attracted to her and she sure was attracted to him. More than one evening ended with her finger fucking herself as she moaned his name into her pillow. She'd even thrown out a few hints lately and once she thought he was going to ask her up to his room, but one of the other guys had broken into the conversation, bragging about some test he'd aced and the moment was lost. What was even odder was that Roger had never mentioned Timmons before at all. Why now? Did it really matter? Donna smoothed her skirt a bit and got up to get to her own class.