Bad Boy Billionaires #1 - The Ivy League Rake(15)

These feelings were mutual. Edwin Sutton would see Elroy walking through Harvard Yard and he would turn his head in an overly dramatic way and pretend he didn't even see him. If they were standing next to each other, Elroy would turn his back on Edwin and pretend he didn't see him. This vitriol went all the way back to a cold night in January when they were in boarding school. Hideous Edwin had become infatuated with a sweet young blond guy from Vermont. He'd bought the blond guy clothes and jewelry, and he'd taken him on vacations to Europe. He would have done anything for this sweet guy-until he caught him in bed with Elroy that cold January night. Elroy and the blond guy were in Edwin Sutton's bed, naked. From a distance, it looked as if they might have been playing leap frog, with the blond on the bottom. They thought Edwin was spending the weekend in Newport with his family. They had no idea he'd returned early because of impending inclement weather.

After Elroy got caught fucking the blond boy ass, Edwin would never speak to Elroy again. So this wasn't the first time Elroy had been overlooked for one of his parties. Elroy had come to expect it and he didn't mind in the least. But when Elroy found out Kyle had been invited to the big costume party that October, and that Kyle was going in drag, he wanted to find Edwin Sutton's newest blond boyfriend-he went for the same type-and sleep with him just to get even.




 

 

On the night of the party, Elroy remained in his bed staring up at the ceiling while Kyle rushed around in the bathroom, putting on his costume. Elroy had nowhere to go that night. Even the Weaver twins had been invited; they were going as football players. Not all that original, but they looked great in football gear and no one would mind.

When Kyle stepped out of the bathroom in full drag, Elroy sat up in bed and gaped at him. He sat there shaking his head, and said, "Unbelievable."

"What?" Kyle said. "Do I look dumb? Are people going to laugh at me? I feel dumb. I've never done anything like this before. I knew it was a mistake." Elroy moved to the edge of his bed and looked him up and down. "You look fine, seriously." Elroy thought he looked too good. Although it was obvious he was a man in drag, there was something so sexy about him that night Elroy wanted to bend him over. He wore a short, tight black dress that hugged his body and made his ass round out. It was so short he had to keep pulling the stretchy material down whenever he moved. He'd shaved his entire body and his long smooth legs looked good enough to lick for hours. The black high heels he wore only made his legs look even tastier.

"I feel so stupid," Kyle said. "I knew this was a mistake." He glanced into a mirror on his dresser and sighed.

Elroy climbed out of bed and crossed to where he stood. He put his hand up the tight dress and said, "I think you look naughty. You should stay here with me tonight instead of going to that boring party. Edwin Sutton's parties always suck." This was true. Elroy had heard all about Edwin's parties from other people. Portly Edwin always grabbed a microphone and sang Madonna songs and tacky show tunes at his parties. The only thing more offensive than his looks was his voice.

Kyle smacked Elroy's hand and pulled his dress down. "Stop that, you perv." He didn't shout. He actually smiled.

"Seriously," Elroy said. "You look hot, man." Kyle had recently stopped wearing glasses and he was wearing his new contact lenses. He'd done this at Elroy's suggestion, only he'd had a hard time getting used to wearing contacts. Elroy reached up and grabbed his fake breasts. They weren't huge obnoxious fake breasts; just a perky little handful. He squeezed the left one and laughed. "Stay here and you'll have a lot more fun with me."

Kyle smacked his hand again and smiled. "Stop that, you idiot. It took me a long time to get these things even." He pushed Elroy away and glanced at the mirror to check out his fake tits to make sure they were still even.

Elroy noticed he wasn't wearing much makeup; just lipstick, some powder, and false eyelashes. Elroy knew he would be wearing a black velvet mask with gold trim, so he probably figured the makeup wouldn't be that important to the costume. The long black wig covered a good deal of his face and it complemented his soft gentle features well. He seemed to have gone for all the details, but in an understated way. His fake red fingernails weren't too long and his gold hoop earrings were almost invisible. Although Elroy had never been into transgendered men or guys in drag, he felt so unusually excited about seeing Kyle in that tight dress he reached down again and put his hand up the back of the dress. 

Kyle gave him a shove this time and laughed. "Stop that, Elroy. You're making me nervous."

Elroy fell back on Kyle's bed and said, "At least you could have worn underwear." This time his hand had gone up his dress higher and he'd grabbed Kyle's bare ass. He never would have guessed that the first time he would grab Kyle's ass, Kyle would be wearing a dress.

"I don't want panty lines," Kyle said, in his usual deep masculine voice. "I'm wearing a thong, a good strong thong. And the thong keeps my junk from sticking out."

Elroy got up and went back to his own bed. He sat on the edge and looked down at his feet. Though he didn't care about not getting invited to one of Edwin Sutton's revolting parties, he would have liked to have gone to this one with Kyle dressed up this way.

Kyle must have sensed something wrong. Normally he would have been on the defensive with Elroy in a situation like this, but that night he walked over to Elroy's bed and glanced down at him. "What are you doing tonight?"

Elroy had a feeling Kyle felt guilty about going to a party to which Elroy had not been invited. So he sighed and said, "I'll just sit here alone tonight. I'll be fine. You go and have fun."

Someone knocked on the door and said, "Are you ready?" Kyle had mentioned a group of people were picking him up and they were all going in the same car.

"I'll be right out," Kyle said. He walked over to a small table near the door and picked up a black evening bag he'd borrowed from a girl in his chemistry class. "You should just go out like you normally do on weekends. There's no reason for you to sit in here alone all night."

"You don't have to feel bad for me," Elroy said. "I'll be okay alone. I'm a big boy." He spoke in a soft, dejected tone, hoping to make Kyle feel even guiltier for leaving him all alone.

Kyle hesitated at the door. "Are you sure you're okay?"

Elroy sighed again and looked up at him. He sent him a pathetic glance and said, "I'm fine. Go on. They're all waiting for you."

"You're sure?"

He was hoping Kyle would change his mind about going to the party and stay home with him. The things he would do to Kyle in that dress and those high heels raced through his filthy mind. For Elroy it wasn't about whether or not Kyle could pass as a woman. He couldn't pass, which was more than evident. The sexual attraction was more about how hot Kyle looked as a man in women's clothing. "I'm sure. I'll be okay. I don't want you to feel bad about me. Just go and have fun."

Kyle shrugged and said, "Okay. I'll see you later." Then he opened the door, joined his friends in the hall, and didn't even give Elroy a backward glance.

After he'd gone, Elroy sat there staring at the door for a minute. He thought for certain he'd be able to guilt trip Kyle into missing the party. When he realized he didn't have as much control over Kyle as he thought he'd had, he got out of bed, went to the closet, and changed his clothes. There was no way he'd stay home alone that night, not with Kyle out having the time of his life in a mini-dress and no underwear. Fuck Kyle, fuck Edwin Sutton, and fuck the goddamn party.




 

 

* * * * Elroy didn't want to be seen anywhere in Boston that night. If anyone did see him alone in a bar in Boston they would report back to Edwin Sutton and that fat little fucker would enjoy this too much. So he put on tight jeans, a tight black T-shirt, and drove to the Cape instead. He knew Halloween weekend in Provincetown would be filled with good-looking young men from all over the east coast. He figured if he was really lucky, he might even meet a nice gay couple looking for a threeway. He knew plenty of gay couples who went to Provincetown just for threeways. They would all claim they went for the shops, the beaches, the whale-watching, and the restaurants. But they really went there for the dick.

When he pulled onto Commercial Street, he found a parking spot near the post office, a comfortable walking distance from the bars. He reached under the seat and pulled out his trusty old handicapped card and hung it from the rearview mirror. Provincetown had the worst parking anywhere and Elroy hated to walk too far for anything. The best parking spaces were handicapped only, located in the center of town. He'd applied for a handicapped card after breaking his leg in a skiing accident two years earlier. At the time, he'd needed it to get around. After his leg healed he got so used to parking in handicapped spaces he decided to hold on to it for as long as he could. And it wasn't as though Provincetown was filled with crippled people. Most of the time the handicapped spaces were all empty anyway and he hated to see them go to waste.

He went to one bar closer to the East End of town and didn't see anything interesting. He was glad he'd worn his black leather jacket that night. The sea breeze there made it cooler than in Boston. After he left the first bar, he walked down Commercial Street with his hands in his pockets, staring down at the sidewalk. Everyone seemed to be with a group; no one walked alone. Many were wearing outrageous Halloween costumes that had glitter, feathers, and high heels. Most were high camp; some were downright hideous. Those who weren't walking around in groups were couples walking hand in hand. He glanced at one couple kissing outside the drugstore and thought about Kyle at Edwin Sutton's party. Without warning, a feeling of doom passed through his body and he couldn't seem to shake it.