The Ivy League Rake (Bad Boy Billionaires 1)

Elroy hadn’t met anyone this backward since the summer he’d spent in Greece. There had been an adorable young man he’d had a summer fling with who got turned on by wearing red high heels. It took weeks to get this little kinky fetish out of the guy, and a few more weeks to get him to put on the red high heels Elroy bought for him. But once the guy put them on, he couldn’t wait to lift up his legs so Elroy could fuck him. Although Elroy figured he had his work cut out for him with Kyle, he knew the shy types were always the most exciting once they finally let down their guards.

“Dude,” Elroy said, “You can’t miss this, seriously, man. If you don’t do the jock strap pyramid you’ll never fit in here. The last guy who refused to do it wound up transferring to another school because no one would talk to him.” He leaned forward and grabbed Kyle’s arms. “Dude, it’s the jock strap pyramid.”

“I don’t know about this,” Kyle said, as he glanced at the white jock strap in his hand.

“Trust me, man,” Elroy said. He smiled wider and spoke with encouragement. “I’ll make sure nothing happens to you.”

Chapter Four

It took a few more minutes to convince Kyle to remove his clothes and put on the jock strap. But Kyle finally managed to gain his trust. When he removed the gray pants and the white shortsleeved shirt and bowtie, Elroy looked beyond his white dime-store underpants noticed he had one of those tight lean bodies, with long muscles that stretched more than they bulged. Without the baggy, ill-fitted clothes he didn’t look nearly as skinny when he was naked. In fact, when he removed the underwear he looked good enough to fuck in the daylight, and without booze. The only minor flaw Elroy noticed was something Elroy would point out to him in the future. Although Kyle wasn’t a hairy guy by any means, he’d obviously never trimmed his pubes. It was a good thing he had six thick soft inches that overcompensated for that horrible big dark bush between his legs.

When Kyle put on the jock strap and turned to arrange his clothes on the bed, Elroy took a good long look at his ass. He had a natural arch at the small of his back with two prominent dimples. He also had a nice long crack and not a hair to be found. Elroy took a quick breath and fought the urge to reach out and grab him from behind to see if it felt as smooth as it looked.

Kyle turned around and asked, “Can I wear socks?” He was wearing black dress socks that older men wear. With nothing else but the jock, they made him look even more innocent and adorable.

Elroy pressed his lips together and shook his head. “Nope. Only a jock strap. Lose the dad socks.” He didn’t point out that the socks didn’t match.

Their room happened to be at the end of a long hallway, near a back stairwell that led to a side door on the first floor that opened to Harvard Yard. Elroy stuck his head out first and checked to see if the hallway was empty before he grabbed Kyle and dragged him into the stairwell. On the way down to the first floor, Kyle seemed apprehensive and Elroy had to pull him by the hand and tell him he would be glad he’d done this rite of passage. To make it sound even more impressive, Elroy mentioned that if Kyle managed to be the guy at the top of the pyramid in a jock strap he would get a special surprise. He emphasized the word surprise; he said it was different every year and no one ever knew what it would be. By the time they reached the first floor and were at the door leading out to Harvard Yard, Kyle seemed so interested in the surprise he didn’t hesitate at all when Elroy grabbed him by the arm, opened the door, and shoved him outside.

The minute Kyle was outside Elroy shut the door and shoved a wedge into the bottom. He’d planned all this ahead of time and he’d left the wedge next to the bottom step. The minute Kyle realized no one else in Harvard Yard was wearing a jock strap he turned and tried to get back inside the building. When he found the door impossible to open and saw the way Elroy was laughing at him, he pressed his palms to the glass and glared at Elroy. He said, “Open the door. This isn’t funny, man.” He banged on the glass with his fists a few times, as a crowd gathered behind him to see who the guy in the jock strap was.

But Elroy laughed in his face again and turned back toward the stairs. He didn’t want to get caught running around in a jock strap. He went back up to the room alone, without so much as a backward glance.

About ten minutes later, the door opened and Kyle walked into the room with some kind of scarf wrapped around his waist. The scarf had a bright green background with large yellow sunflowers everywhere. When Elroy saw this ridiculous sight he fell back on his bed and laughed so hard he doubled over sideways. “I got you,” he said. “I didn’t think you’d fall for it, man. Fuck, dude, that was too fucking easy.”

“Ah well,” Kyle said. He spoke with a clear, even tone. He glared at Elroy again and lifted one eyebrow. “You got me, oh yeah. That’s right, Elroy. You got me good this time. I’m glad I worked this hard to get into Harvard so you could have me prance around Harvard Yard in nothing but a jock strap on one of the busiest days of the semester. Oh, yeah, you got me good. You don’t know how wonderful it makes me feel to provide your personal entertainment.”

Though Elroy noticed his serious tone, he still couldn’t stop laughing. “You should have seen the look on your face when I shut the door, man. It was priceless.”

Kyle removed the sunflower scarf and threw it toward Elroy’s bed. It landed on Elroy’s head, which only made him laugh harder. Kyle walked to his bed and pulled off the jock strap. Then he threw that across the room and it landed on Elroy’s face. When that happened, Elroy laughed so hard his stomach muscles ached.

“I’m glad we’re roommates,” Kyle said. He opened his footlocker and pulled out a pair of gray sweatpants. “My only goal in this life from now on is to provide fodder for your entertainment. I can’t believe how lucky I could get to have you as my roommate.” Then he put on the sweatpants and slammed the lid so hard it made Elroy jump.

Elroy pulled the jock strap off his face and he stopped laughing. For the first time that day, he wondered if he’d gone too far. After all, this guy didn’t seem like trouble. He was attractive in an unpolished way with that longish brown hair. He might be a good fuck on a cold winter’s night, and he seemed smart enough in case Elroy needed help with any of his classes. He’d never been the best student.

So Elroy stood up and cleared his throat. He walked over to Kyle and extended his hand. “It was only a joke. I was just playing with you, buddy. Don’t get mad, seriously. I promise I will never do anything like that again. I swear on my life.”