I met Jeff Andrews in college. Back then, I was still in the closet. He was a handsome, cocky frat boy, and I found that as long as I played straight enough, I got to hang out with him. Of course, I never tried anything on him, and even after college when we had kept our friendship up and I eventually came out to him, I was surprised that he was so accepting. But he really didn't care. Jeff was as straight as they come. He was a notorious playboy all throughout school and throughout the time after. The fact that his company took off so quickly and made him rich in his thirties didn't help his own narcissism and revolving door of girls and girlfriends. But despite his egotism, I always liked him: There was something charming about him that I wanted to be around but dared not go for. Our lasting friendship was sort of a long-term tease that would never result in anything, but I was okay with that. I just lived day by day, always aware that I was different from the people I was friends with, but trying not to let it make me feel like the outcast of the group. Of course, that's often more difficult than it sounds.
When I was thirty-seven and Jeff had just hit forty, he finally settled down and got married. Again. This time, it was to Tiffany, an attractive twenty-five year old brunette. Tiffany was sort of like Jeff, only smarter. I could read girls better than any straight friend, and it was obvious the minute I met her that she was someone with goals in mind. She was flirtatious, feisty, and there was something a little dangerous in her eye. We quickly hit it off and bonded over movies and fashion, and one time she told me she trusted me more than any of Jeff's other friends. Jeff himself was ecstatic: He finally found his perfect trophy wife. His first wife, Miriam, was goal-minded, too, but a little less stealthy about it. She was boisterous and shrill and extremely arrogant. I had never liked her, but she and Jeff had a son who lived with him after the divorce.
Kyle was eighteen, and I had known him since he was born. He had Miriam's baby face, which he tried to cover up with a lip ring and hoodie: It only drew attention to his pretty eyes and smooth skin. I had always thought he was a cute kid, and he was just reaching the age of becoming handsome. When Jeff and Tiffany got married, I wondered how Kyle would take it. While the three of them were together as a family, I hardly ever saw them talk or much less even look at each other. Maybe they figured he would be gone off to college soon, so it really didn't matter. Besides, despite the success of his company, Jeff really wasn't too bright. He either didn't notice, didn't care, or both.
One time, Tiffany and I went out for lunch. We had been meaning to get together for some time, and she found a cute little Thai place downtown that I met her at. We hugged, and as we ate, I told her about my various dating and sex tragedies, how I liked fucking but was ready to fuck someone really special at this point. Good men are hard to find. She stopped eating and smiling and suddenly looked a little hesitant, like she was about to say something. I looked at her intently, waiting to hear it, and she leaned in a little, lowering her voice. "Do you like younger boys?" She asked.
I laughed. "Younger, like thirty? Honey, when you're my age, anything under thirty-five is young."
"Younger like eighteen?" She asked, with a twinkle in her eye I seemed to know well.
I paused with a smile still lingering on my face. "That's pretty young for me." I said. "Maybe for a one-night-stand. But nothing serious."
"This is pretty serious." She said. I blinked at her. My smile had almost faded off.
"You know, since I got married to Jeff, I've told you about the sex that we've had. I've made it sound pretty good, but I'm a great storyteller. Really, it's kind of sub-par. I like Jeff and all," ("His money," I thought) "but Kyle-"
"Kyle?!" I exclaimed. "Are you looking at Kyle?"
"I've been looking at Kyle since before I got married." She said. "But you see - He's been a bad boy." I got a little tingle when she said those words. I sort of love hearing that phrase. "I tried just being friendly with him at first, but I knew he didn't trust me. He's sort of aloof, you know?"
"I guess so."
"And since I've been in the house, he acts like I'm nobody, when I'm his legal guardian! Do you know what it feels like to live in a house where the kid you're supposed to be in charge of thinks he's better than you?"
"I'm sorry to hear that." I said slowly.
"But I have a question to ask you - Do you like younger boys? Like, Kyle's age?"
"I like looking at them."
"Would you like to fuck for me?" She said in a low voice. A naughty little smile spread across her pretty face. It looked out of place in that cute little restaurant. I imagined she'd used it on Jeff plenty of times.
"Tiffany!" I said, and laughed because it was the only reaction could make.
"Brandon, at first I tried not to let it get to me. I tried being understanding. Now, I just look at him and I just want to- to- to nail him, you know? The little brat."
"But Jeff's my friend!"
"I have a way to keep you safe." She said. "He's going to college soon. Plus, he tries to be tough. He wouldn't tell a single soul if someone ever fuck him in the ass." Again, those harsh words sounded so weird coming from her.
"Are you serious?" The whole thing seemed completely ludicrous to me. "And what would I do afterward? Just come over the next day for a barbeque with the family or something?"
"You've told me you don't like it here." She said. "You've said that sometimes you just wish you could quit your job and just move to the other side of the country and get away from everything. Honey, I can help you with that." And then she got out a checkbook. "A little early birthday present from me, courtesy of Jeff Andrews." She smiled again and winked.
That made me pause. "Let me think about it." I said quietly.
"Sure!" She snapped back to her bubbly self. "Take all the time you need. Just give me a text when you're ready."
We split the lunch and hugged before saying goodbye, and that night I sat on my couch with my phone in my hand. Another life if I fucked a cute little punk? When I was Kyle's age, I wanted to fuck so badly but was so scared of myself. Starting a life over again sounded better and better every passing second I thought about where my own life had led me.
"Okay," mumbled, and I texted Tiffany without thinking twice. "I'm in."
She told me to come by on a Saturday night, on a weekend I knew Jeff was out of town golfing with his buddies, who were basically like the frat boys we knew in school, just older and somehow even richer now. I parked my car in their driveway and walked up to the enormous house with nothing but my keys with me. Tiffany had told me I didn't need to bring anything. I told myself to not even think about it, just to do it. I knew Jeff, but he really never talked much about his son, and Kyle never talked to me, either, so he was sort of like a stranger, right? The most I knew about him was through Tiffany.
The door was unlocked. "Come in!" came Tiffany's cheery and playful voice.
I walked through the door and down the hall where she met me. She looked happy and energized and particularly lovely in her jeans and blouse. We hugged like we always do, and when she saw that I looked pretty nervous, she asked me if I wanted something to drink. "No, I'm fine," I said.
"Well, I'll get you something anyway. You might just need it." She smiled and winked at me again. What a little tease.
We went upstairs into Jeff's bedroom and she opened the door. "Shh," she whispered. "He's sleeping."
And there was Kyle. He looked drugged to shit, his hair mussed up and his feet bare. His shirt was open, showing his pale chest with a light dusting of hair, and his jeans were undone and hanging around his slender hips. His wrists were tied around his knees as he lay on his side. Tiffany had really done a number on him. And I have to admit, just seeing that boy there was enough to get my dick's attention.
She climbed onto the bed and crawled over to him, and I became strangely aware of her shapely ass and thighs. If I were straight, I'd probably love to bury myself between those legs. "Heyyy sleepy boyyy..." She cooed. "You've got a friend come to see youuu..."
I saw him strain his neck to lift his head in my direction. His eyes looked kind of blurry. He hadn't met me many times in his life. He might have remembered me from somewhere, but being all drugged up, maybe he didn't. He made a tired groan like a sleepy teenager having to wake up for school. Tiffany started stroking his hair and his cheek. "Come on, say hi?"
I didn't know if she was talking to him or me, but when she looked up at me, she cocked her head to the side, beckoning me over. I laughed nervously as I kicked off my shoes, my hard-on just coming to life. It was so scandalous I just didn't know what to think. "Your shirt" I heard her whisper with a strangely authoritative tone. I pulled it off over my head before timidly crawling on the bed toward them. It felt weird to be in Jeff's bed with his wife and his son.
As I got closer, he tried to pull himself up, not realizing he was tied. Tiffany put her hand firmly on his chest. "No, no, no," she said, and she pushed him back down onto the bed.
"You think you can do whatever you want, huh, you little punk?" Her voice never lost its sweetness, and for some reason being so close to them got me even harder.
"You know what? You're gonna do somethin' you do wanna do, huh?"
