Bad Boy

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?"

"What?" He asked breathily, still utterly confused. Poor kid. She put her finger to his lips.

"You don't talk, boy." She said, suddenly harsh. "In fact-"

She reached into the nightstand drawer and pulled out strip of cloth. I knew what was coming next. Before he had time to react, she had gagged him. "There," She said, brushing some unruly hair out of his beautiful eyes. "Perfect."

There was a pause, and she continued in her chirpy voice, turning to me. "Isn't he cute?" She asked, smiling wickedly.

I couldn't help it, I had to tell the truth. "Yeah."

He did look adorable, cuter than I remember him, all tied up and gagged, eyes half-open. And just so - new. A virgin to gay sex. I had to touch that little body. I reached my hand out before withdrawing it, looking at Tiffany like I was looking for permission. She paused, "Go ahead!" she said, amazed I'd hesitated.

I stroked his chest, which looked sort of meager until I felt the smooth muscle underneath his taught skin. God, how much I wanted to do this with the boys I went to high school with! He recoiled a little at my touch, though it was really soft, and so I moved to his arm, feeling the muscle and strong bone underneath it. It kind of made my breath quicken. His eyes got wider; he was starting to understand.

Tiffany let out a girly giggle and stroked his cheek again. "Yeah, he's a cutie. But he's a bad boy-" (again, that phrase) "who needs a lesson."

Before she got off the bed, she motioned for me to turn him over, so I took a deep breath (there was no turning back now) and got behind him, propping his hips up. Because of the way he was tied, his face was already pressed into the bed and his skinny ass was up in the air. It looked so inviting. "Turn his head toward the edge of the bed," she ordered. Without thinking, I did so. Clearly, when Tiffany wanted something, she got it.

When I turned around, she had taken off her top and was wiggling out of her jeans. I thought I was supposed to be the one fucking him. She stripped totally naked in front of us, and Kyle turned his head away, not wanting to see what his dad was fucking, I suppose. But I couldn't stop admiring the soft curve of her hips and her breasts that swayed when she turned, and she barely seemed to notice them. She stooped down to pick something up, and when I saw what it was, I let out a little "Oh, my God."

It was a dildo. She grabbed the kid underneath his chin and waived it in front of his face. "You know what this is?" She said in a demeaning sort of way. He didn't answer, so she answered for him.

"It's a dildo, and you're gonna suck it like a good boy. How does that sound?" She strapped it onto herself with incredible ease.

I heard him make a muffled sound, and she leaned in closer. "What's that?" She untied the gag.

"Nuh-uh," was the response. I looked at her. That wasn't a good idea.

"Oh really?!" she said. "Well, that's too bad, baby, because if you don't do it, we might just spank your naughty ass until you do. How does that sound, baby?" She looked at me. Her intense stare commended me without speaking. I had never done something like that before, just in play.

"Go on, Brandon," she ordered. She looked like a different girl without all her smiling and giggling.

I didn't think, I just grabbed the top of his jeans and pulled them down over his ass. They were undone already, and fell bunched at his knees. And there he was. I was overwhelmed at having his naked ass so close to me and I acted without thinking, rubbing my hands firmly over it and kissing it. He made another muffled noise when I did.

"No," I heard her say. "Don't baby him. Show him who's boss."

I got my hand ready and held it up. He was anticipating it and gave out a whimper before I even let me hand fall onto him. The slap rang out in the room. It scared both of us.

"Again!" she said. "Harder! Make him feel it!"

I put one hand on his lower back to steady him, and this time I put some force behind my hand. There was something strangely satisfying about punishing him. The next time I spanked him, I whispered, "Bad boy... Naughty boy..." His moans were becoming more pathetic sounding as the stinging began to set in, and he dug his face into the bed, embarrassed at his own weakness. Soon, his pale ass was pink and then red. The sensation of disciplining overwhelmed me, and after I was done, I pressed my hand onto his hot raw ass, liking the way he squirmed with discomfort at the burn.

By now, Tiffany had strapped on the dildo and walked up to us, Kyle's face still buried in the mattress. "Here! Here!" she grabbed him by his ears and lifted his head up. "Suck it!" He struggled to turn his head away, but the kid was tied up - he didn't have a chance. I anchored both my hands on his sides, pinning him down. She held her grip on him and found a way to force it between his jaws. I felt his body heave under my hands as he gagged on the first thrust. She pulled back just enough before plowing in again. He coughed and made a gurgling sound and she pulled back again.

"A little gentler," I said, "You don't want him to throw up."

"Don't tell me what to do!" She snapped. When I looked at her face again, it was a picture of anger and concentration. Her eyes were fixed on her prey, her lips snarled and her face red. Tiffany gets what she wants or she gets it tenfold. But she didn't go in so deep the next time, and she actually started moving her hips in a rhythmic way as she got used to thrusting.

She did this for a while, until I imagined his jaw was getting sore. I could see his face was flushed from exertion. But watching him take that big cock in his mouth was so enticing to me. I was ready to take him. When Tiffany's and my eyes met again, I said, "I want to now."

"Go, then!" she asked, almost sarcastically, like a dare. Maybe she thought I wouldn't go through with it.

"I will," I taunted back. She smiled and pulled out of his mouth. When she did, he coughed and cried a little, unable to hold back his tears. While he was sniffling, she grabbed the gag again, easily slipping it on him. He looked too exhausted to move, even if he hadn't been tied down the way he was.

I looked around. "Do you have any lube?" I asked. I didn't want dry sex for either of us.

She smiled, this time more mischievously. "Use your imagination." I got the picture.

I spread his ass open and saw the most beautiful thing I'd seen in my life, and in spite of myself, I whispered what I would say if I was fucking any guy - "Oh - hello, baby." And I dug in, licking and sucking and get him as wet as I could. He clenched hard and made it a little difficult for me, but I was up for a challenge. I was starting to get bolder now, seeing Tiffany and how rough she was with him.

I pulled back. "If you don't open up, you'll be sorry. I'll make your asshole hurt a lot." I didn't realize I was sounding so threatening, but I waited a bit while he made up his mind and the next time my tongue was there, he had relaxed much more. Still nervously twitching, but it was something I could work with, swirling my tongue around, getting plenty of saliva inside.

When I felt I had done enough to give us both a smooth enough ride, I unbuttoned my jeans and pulled them down to my knees, my purple hard-on popping up to look me in the face. I bent my head down to spit in my hands.

"No," I heard Tiffany say. I had almost forgotten she was there. I looked up to see her get onto her knees in front of me. "No, baby..." She cooed, and took my cock in her hands. She engulfed it in her soft, warm mouth, lubricating me just as good as any man I've slept with. Yup, Jeff was a lucky guy, I guess. It didn't feel sexual, though. It was a friendship thing, an "I've-got-your-back" thing. While she bobbed her head up and down on me, we looked each other in the eye and I smiled at her. "Thanks."

When she decided se had given me enough, I turned and got my grip on Kyle's ass again, forcing his back to arch up even higher toward me. In a last desperate attempt, he tried to wriggle out from underneath me. Tiffany wasn't having any of that. "Hey!" She yelled, and she grabbed the kid under his chin and brought her face as close as she could to his. Almost kissing distance.

"You think you can squirm your way out now, do you? Remember who asked for this, Kyle. You try something like that again and I'll fuck you myself. Is that what you want?" She didn't even give him time to answer before she shoved his face back down onto the mattress. Then she let go and left the two of us on the bed.

I lined myself up, and when the head of my dick touched his asshole, he cried out, trying to pull away. "No, no..." I said softly, like hushing a child. And I tried again. When he clenched up a second time, I got impatient fast. I put my arm around his waist and spanked him hard. "No!" I shouted.

"Yeah..." I heard Tiffany say. She was seated like a cat in the armchair by the bed now, her dildo still strapped on, with its stark erection jutting out between her lean thighs. She was studying us intensely, watching the scene unfold in front of her like a director. This was her show; Kyle and I were just actors.

I caught myself when I remembered I was being watched, and so decided to say nothing more, nosing my cock against him until I felt resistance. This was going to take some coaxing. I pushed in just little further, and he squirmed again and moaned. Really, he was just scared of the pain. I put my hands on his hips and leaned back, watching my dick inch its way in, stopping each time he tensed up again, waiting, and then continuing. Then I realized I could get the hard part done quickly, took a deep breath, and forced the rest of my length into him, until my pubes hit against his ass. He yelled when I did it, but then I leaned forward and let him feel my chest against his back, moving my hands from his hips and hugging him around his belly. There, he just cried quietly while we sat together, letting him get used to me in him. He was so tight it was almost overwhelming.

When I felt he had had enough time, I pulled out as gently as I could. I went nice and slow. "Shh" I hushed, stroking his back. "You're doing such a good job taking that cock." He squirmed and twitched underneath me, whimpering the whole way through. It sounded so sweet. Every time I would push in to the hilt and stop for a second, I'd feel him shiver a little, and then whimper again when I moved. "What a good boy."