“Freak by Night 6: Costs & Benefits”
When my wife Traci begged me to bail her little brother Trey out of jail a fourth time and let him stay with us, I was more than reluctant. We’d given his sorry ass so many tries and I honestly wanted to square up with him and knock some sense into his head. However, he was my wife’s only sibling and the uncle to my two daughters. So I gave in and bailed him out, and I even let him crash on our sofa until his trial date. My wife thought I was doing it out of my love for her, and I admit that was a small part of why I did it. The biggest reason why I did it was so that he would owe me and owe me big. There was gonna be a cost for his actions and he had no idea how big that cost would be.
Traci and the girls went out of town to visit her and Trey’s parents for the weekend. Since Trey had to wear a court ordered ankle monitor and couldn’t travel more than a mile away from our house, I told Traci that I’d stay behind and keep an eye on him to make sure he stayed out of trouble. The moment her and the girls left, I put my plan into motion for that night. If it all worked out, I’d be getting a benefit for the cost of taking care of his sorry ass.
“Trey, hang up the phone,” I told him as I stepped into the living room.
“In a minute,” he said without looking at me. He resumed his conversation on the phone and I walked over to him and snatched his iPhone out his hand. “Yo, what the fuck are you…”
“Shut up.” I put the phone up to my ear and told whoever was on the other line, “He’ll call you back later.” I hung up on them and put his phone in my back pocket. “I’m gonna keep your phone for the weekend.”
“What? Dex, why are you trippin’?”
“My house, my rules. If you don’t like it, then go sleep out in your car or better yet violate the court order and spend the weekend in jail.”
“My sister ain’t gonna like this when I tell her.”
“You tell her and not only will you be out of here, I’ll kick your ass before I throw you out. I spent my hard-earned money on your young and dumb ass. Not only did I have to bail you out, I had to get you a qualified attorney for your trial. Do you know how much money that cost?”
“I already said thank you.”
“Yeah, but I don’t like the way you said it.”
“What?”
“Boy, you heard me. Now, you’re not in a jail cell with some ruthless ass niggas because I helped you. And since I helped you big this time, you owe me big.”
“What you want me to do, man? You want me to clean the gutters or some shit?”
I laughed and told him, “You wish. Nah, I got some other shit planned. Trey, I got some shit planned that’s really gonna…” I stopped myself and said, “I need you to pick me up some stuff from the CVS up the street.”
“Why can’t you get it?”
“Because, I asked you to get it.” I pulled the list of items from my pocket and handed it to him. “Get everything on that list.”
“Uh…okay. But I’ma need some money to get it.”
Me (Dexter Holmes)
I pulled out my wallet and gave him two twenties before telling him, “Bring back my change, too.”
He stood up and asked, “Why couldn’t you go and get this stuff?”
“Because I’m going to the gym and it’s not in that direction. I’m going straight to the gym and then I’m coming back here. Your ass better be here when I get back or you’re gonna owe me even more.”
“Dexter, I understand I fucked up but…”
“You fucked up big.”
“I know and I’m sorry. How many times do I have to say that? I apologized to you, my sister and my nieces. Traci, Denise and Tamara forgive me. How come you don’t?”
“Because unlike them, I can see through your bullshit. Boy, you can’t fool me. I knew you’d turn out to be a sorry piece of shit back when you were fifteen and I first started dating your sister. Seven years later and you’re still getting into trouble and relying on others to help you. Well I’m here to tell you now that your luck done run out. Yeah, you might actually change your ways after tonight.”
Trey Michaels
The way he was looking at me told me all that I needed to know. I’d gotten into his head. I’d put some degree of unknown and possibly fear into his mind. I waited until he was gone before I grabbed my gym bag and headed out myself. When I got to the gym, I headed into the locker room and changed into my workout clothes. After bench-pressing, I did a little cardio but not too much. I had to make sure I’d be energized and ready to break him in. And by break him in I meant fuck the living daylights out of him.
You see, I hadn’t fucked another man since my college days. I played football in college and just like with my high school team, there were a small number of DL teammates that all knew about each other. I fucked four of them regularly until I met Traci on-campus and got serious with her. I married her after graduation and we started a family. I’d considered myself bisexual but never told her because I never felt that urge to be with another man the way I felt it back in high school and college. However, I still had an attraction to men and I’d been watching Trey ever since he turned eighteen. And now that he was twenty-two and a grown ass man, I had nothing to feel guilty over. His ass was literally mine.
“You got my change?” I asked the moment I reentered the house.
“Yes,” he replied with an attitude.
“Watch the attitude.” I snatched my money from his hand.
“Can I have my phone back please?”
“I told you I’m keeping it for the weekend. You won’t be making any calls or sending any texts until Sunday evening when Traci and the girls return. Is that clear?”
“Yeah man, whatever.” He sat down on the sofa. “So, what did you need that stuff for?”
“Some of it is for me, and some of it is for you.”
When I said that, his face scrunched up and he asked, “For me?”
I smiled and revealed, “Yeah, it’s for you. You’re gonna need both that Astroglide before and those stool softener pills after what I’m gonna do to you. The Fleet enema stuff is for both of us, I mean I wouldn’t want you to shit on my dick. That would be embarrassing as fuck for you and it would probably piss me off to the point that I’d knock you out.”
“Yo, what the fuck are you talkin’ about? What kind of shit you think is goin’ down up in here? Because whatever it is I’m not down for it.”
“Oh, yes you are. You’re gonna be down for whatever the fuck I say you’re down for. Traci’s not here, man. It’s me and you the whole weekend.” I tried to touch him but he flinched and then jumped up.
“Hell nah! That shit ain’t even gonna happen! And does my sister know you fuck niggas up the ass?”
I grabbed him by the neck and choked the fuck out of him while telling him, “No, and if you tell her you’ll be going to jail with an already opened asshole. Boy, don’t fuck with me. Your days of fucking with me are over. Did you honestly think I was gonna bail your narrow ass out a fourth time without you having to give up something? Nah, that’s not how it works, Trey.” I let him go and he started coughing.
“You’re fucking crazy!”
“Call me crazy all you want but you were the one who decided to beg your sister to beg me once again to help you out. Your parents are done with you, man. Me and Traci are all you got.”
“I can’t believe this shit. You played football! How the fuck does someone as big as you get fucked by other niggas?”
“There’s a lot you don’t know about what people do in private. If there are gay and bisexual men everywhere else, then why the fuck wouldn’t there be any on football and basketball or any other sports teams? You can’t be that stupid. And I never said anything about getting fucked. I’ve never been fucked. But I have busted quite a few asses open.”
His eyes began to water and his face turned red as he pleaded, “Don’t do this, man. I’m not gay or bi or any shit like that. I let a few trannies suck me off before but never no shit like this. I’ve never even let a girl lick my ass let alone touch it.”
“Mmm, I am gonna enjoy taking your anal virginity then.”
“Come on, Dex. I’ll do whatever you want other than this.”
“You don’t have any other options. You could either do this my way or leave my house and my yard.”
“Cool, I’m out then.”
“Fine, let me go get some scissors to cut the ankle monitor off with then.”
“What? Come on, man!”
“Nope, you can leave but the moment I cut off the ankle monitor, the cops are gonna come. You’ll have some time to get from here before they get here.”
He stepped back from me and asked, “Can I just suck your dick and that be it?”
“No. I haven’t done this since I got serious with your sister during my last year in college. I know you don’t wanna hear it but your sister has got some damn good pussy. That woman knows she got the juiciest and tastiest pussy on this planet. Her pussy grips my dick and…”
“Alright, alright. Stop! That’s my sister, nigga!”
I laughed and said, “My bad.”
“So if I do this, we’ll be even?”
“Yes.”
“And I only have to do it this one time?”
“Well, I’ve been told that once some dudes have been fucked they take a liking to it. But what do I know? I’ve never been fucked.” I chuckled and he shook his head. “So, what’s it gonna be?”
“No one will ever know, right?”
“Right.”
“And you’re not gonna kiss me or nothin’ like that?”
“Actually, you got them sexy puffy pink lips like your sister. If I wanna kiss you then I’m gonna do it.”
He threw his hands up and asked, “Man, what do I get out of this other than staying out of jail?”
“You’ve never had to stay overnight downtown before. I had a buddy get arrested and had to spend just one night there and he got raped because he was too small to intimidate the dude he was placed in there with. That place is a jungle.”
“That’s basically what you’re doing to me.”
“No, what I’m offering you is your very own costs and benefits situation. I make enough money to take care of my family and also to keep you out of jail from time to time. I have more than enough to continue providing for you since you have nowhere else to go even after the court lets you remove that monitor. I could talk Traci into letting the girls share a room for a while and let you sleep in the extra bedroom. Trey, there’s so many ways I can continue to help you but in order for me to do that, I need you to pay me back and the only way you can pay me back is by providing me with a service. And this…” I reached around him and grabbed his ass. “This is what you have to offer.”
“So if I do this, I can stay here?”
“That depends on how long you’re willing to pay for it.”
“Okay.”
“Okay, what?”
“I’ll do it. I’ll do whatever you want me to do. You’re right, I have nowhere else to go. Some of my friends won’t even answer my calls or reply to my texts.”
“Alright then, let’s go get cleaned up.”
I made him come with me to the bathroom I shared with Traci and we took off all our clothes. I’d seen him shirtless before but seeing him naked was different. He had a nice plump ass on him. His dick was much smaller than my ten inches but it wasn’t tiny. He was soft so I couldn’t judge it. I expected him to put a fight when I removed one of the bottles of Fleet from the box but he just bent over with his hands on the tub and his ass up in the air. I carefully inserted the nozzle into his ass and squeezed all of the fluid into him. After a few seconds of holding it, he went over to the toilet and released the contents from his ass. I was surprised by how well he was taking it all.
“What next?” he asked while still sitting on the toilet.
“I’m gonna fill it with water and you gotta keep pushing it out,” I told him. “Once it’s clear, you’re good to go.”
He wiped his ass and flushed the toilet before continuing. Normally, watching that process wouldn’t be pleasing but watching him go through it turned me on. His little tight asshole turned redder each time I inserted water into it and had him push it out. My dick grew hard and he did his best to ignore it and not look at it, but I caught him staring a few times. After he was cleaned out, I turned on the shower and we climbed in together.
“Clean my dick,” I ordered while staring into his face.
“Yes, sir,” he said while grabbing the body wash and squirting some out onto his hands. He rubbed it on my dick and balls and cleaned me.
“My dick big, ain’t it?”
“Yes, sir.”
I loved that he was cooperating and calling me sir. That shit was turning me on and I didn’t even have to tell him to do it. It was almost like he was getting into it but that couldn’t have been what it was. What straight man in his situation would be looking forward to taking a thick ten inch dick in their ass for the first time? Maybe the idea of being able to stay was fueling him. Either way, he was going to pay that ultimate cost.
“You go ahead and put on some clothes,” I told him after our shower. “Wait for me on the sofa.”
“Okay,” he replied while putting on lotion.
“I don’t want any resistance, Trey. I want you to be calm and ready.”
“Yes, sir.”
He left the bathroom and I looked at myself in the mirror. I didn’t feel an ounce of guilt for what was about to go down. I’d given Trey many opportunities to get his act together and since he hadn’t, I was giving him an incentive to do it. So I put on some lotion and other stuff to make sure I smelled good for him. I wrapped my towel around my waist because I just wanted to be naked quicker when the time came.
I left the bathroom and stood in the hall and watched him as he lied on the sofa watching TV. He was shirtless and had on a pair of Family Guy pajama pants. Just like I’d asked, he was calm. His legs were spread a little and his feet were together. And since he didn’t have on socks, his ankle monitor was right there in the open.
“You ready?” he asked when he noticed me in the hallway.
“Yeah,” I answered before stepping into the living room. He was about to sit up but I told him, “No, stay just like that.” I picked up the remote from the coffee table and turned the TV off. I then took my towel off and put it on the arm of the sofa.
“You are gonna take it easy, right?” he asked me. “I don’t wanna bleed or anything like that.”
“I’ve done this before, Trey. I’ve never made anyone bleed.”
I climbed onto the sofa and on top of him and was surprised when he didn’t flinch. I looked into his eyes before kissing him and after putting up a small fight at first, he kissed back. His lips were puffier than Traci’s so kissing him was quite hot. I got in between his legs and he wrapped them around my waist without me telling him to. My hard dick poked the crotch area of his pajama pants and I knew he could feel it because he’d gasp or move a little each time it happened.
“Do you want me to stay silent?” he asked. “Or do you want me to say some shit? Because the silence is makin’ me nervous.”
“I guess you can act like you’re into it,” I suggested before turning my attention to his neck. I sucked on it and he exhaled loudly.
“That feels good.” He put his hand on the back of my head as I gave him a hickey. “Do whatever you want to me, Dex. I can take it.”
“Is that right?”
I smiled and kissed his sexy lips again before kissing my way down to his chest. I licked, sucked and lightly bit his nipples. His breathing increased as I licked my way down his abs to his navel. I grabbed his pajama pants and pulled them down to his ankles before pushing his legs up and exposing his tight pink asshole. My mouth watered at the sight of it. This was the first man’s asshole I’d seen in person in years so of course it had me turned on to the max.
“You gonna rim me?” he asked while licking his sexy lips. “I’ve never had it done before so I’m a little anxious.”
“You’ll like it,” I told him.
I wet my lips before pressing them against his asshole and sucking on it, making him shiver. I then rimmed him with my tongue to get the outside wet. He was so tight that it was a challenge getting my tongue inside, so I placed my hand on his stomach and caressed his abs to get him to relax more. He exhaled and relaxed and allowed my tongue to enter him. I could tell he was holding back and trying not to allow himself to enjoy it, but I knew he wouldn’t be able to hold it in much longer. I pressed my lips against it again and rubbed on it aggressively and he moaned.
“Ah fuck,” he called out before gasping. His body jolted a few times but he quickly regained control of himself and looked up at the ceiling.
I kissed and licked his balls before rimming him again. By now, his dick was hard and leaking precum onto his abs. That’s what I loved about anatomy; no matter how against man on man sex a guy might think he is, he couldn’t stop the automatic reactions to stimulation. His dick was stiff while I ate him out and he was moaning and telling me to keep going.
So after tasting his virgin asshole for over thirty minutes, I snatched his pajama pants off and dropped them to the floor and made him suck my dick. At first he just licked on it and licked my balls, but then he took me into his mouth and wrapped his lips around my dick tightly. I could tell he’d never done anything like this before but he looked so sexy doing it that it still made me feel good. I pushed it in deeper a few times and choked him and he’d gag and get it wetter with his saliva. I loved hearing the sound of him gagging on it. That shit was like music to my ears.
“How does that dick taste, boy?” I asked him.
“It tastes good, sir,” he replied while looking up into my eyes.
“Damn right it does. Keep sucking that dick.”
I face fucked him, sometimes making it tap his throat and other times poking the inside of his cheeks. Every once in a while, I’d pull my dick out of his mouth and smack his face with it or rub it on his lips and under his nose. I wanted him to worship my dick and at the same time appreciate the opportunity I was giving him. I wanted to see it in the way he looked at me.
“You wanna get fucked?” I asked him.
He stopped sucking me and answered, “Yes.”
“Yes, what?”
“Yes, sir. I wanna get fucked.”
“That’s what I wanna hear. Damn.” I made him stand up and turn around. I smacked his ass a few times before sliding my finger between his butt cheeks and rubbing on his asshole. “I’m gonna open you up good. Lay back down on your back and spread them legs.”
He lied down on his back and spread his legs, and I grabbed the bottle of Astroglide from the coffee table. It had a mild numbing agent in it which could help him take my dick better. I put some on my finger and then pushed it against his asshole. He remained relaxed so his asshole didn’t put up much of a fight as I pushed my finger inside it. He did clench up a few times, but he wasn’t pulling away. He was just so damn tight. I’d never felt an asshole or pussy that tight before.
“Yeah,” I said with a smile on my face. “I’m gonna enjoy this. You really gonna let me fuck this tight ass?”
“Yes, sir,” he replied. “Take it, it’s all yours.”
“All mine?”
“Yes, sir.”
I kissed his lips before working a second finger into his ass, which made him breathe heavier and grab onto my arm. More precum dripped out of his dick and onto his sexy abs. When I started pushing my two fingers into him as far as they could go, he grabbed his dick and held it; making even more precum roll out of it. That shit had me so horny and turned on that I just wanted to ram my dick into his ass and make him cry. But I controlled my urges and continued to open him up slowly.
It took a good while, but I got him open enough to where I could probably get the head of my dick into him without him begging me to stop. So I put some of the Astroglide onto my dick and then sat the bottle back down on the coffee table. I got in between his legs and made him hold them back as I rubbed the head of my dick on his asshole a few times. His asshole contracted and loosened as if he were ready for me to put it in, so I began pushing it into him. That’s when he really started breathing heavy and squirming under me.
“Don’t bitch out now,” I told him. “You’re gonna take this dick.”
“Yes, sir,” he said, his lips now quivering.
He looked so fucking sexy like that. There was nothing he could do but embrace the pain and pleasure. His dick was steadily leaking precum as my dick made its way inside of him. I’d manage to move an inch more into him and he’d place his hand on my abs to stop me so he could get used to it. We did that back and forth for like ten minutes before I’d managed to get most of my dick inside of him. I held it deep in him and let him get used to its presence before I began a slow rhythm. Usually by that point with Traci during sex I’d have her squirting all on me and her legs shaking. With Trey, he was still holding back and I was determined to bring out whatever he was trying to keep me from seeing.
I tested the waters by banging him a few times and he quickly placed his hands on my stomach to stop me. His face turned red and his asshole clenched up on my dick. I leaned forward and kissed him a few times to get him to relax and he did. He let me restart my rhythm and I took it slow with him again. It had been so long since I last fucked another man but I couldn’t get too carried away with it. I didn’t wanna hurt him too much.
“Yeah, like that,” he moaned. “Fuck me just like that.”
“You like daddy’s dick?” I asked him.
“Yes, daddy.”
“Are you gonna share this dick with your sister?”
He looked up into my eyes and replied, “Yes, sir.”
Hearing him say yes to that made me want to fuck him more, so I pushed into him faster and harder. He didn’t put his hand on my stomach that time so I kept going. His dick was still so hard, which I’d never seen before. Usually when I fucked a guy, his dick would be hard at first and then would go soft while we fucked until he wanted to catch his nut. With Trey, his dick stayed hard and kept releasing precum off and on. His abs were pretty much covered in it. I used some of it to lube my dick up even more before fucking him even harder.
“Ah fuck!” he hollered. “Dexter!”
“Say my name, baby,” I told him as I wrapped my hands around his throat. “Take this fucking dick!”
I choked him lightly while fucking him hard and deep. His eyes filled with water and he gasped for air. I slammed my dick into him a few more times before pushing into him as deep as I could go and holding it. I removed my hand from around his throat and he sat up to kiss me. And I mean he kissed me passionately. His whole body was shaking and his asshole was contracting on my dick like crazy. He wrapped his arms around me while still kissing me. I found myself wondering if he was still pretending to like it.
“Get off my dick,” I told him while pushing him back and making my dick pop out of his ass. “Turn around and put that ass up in the air.”
He turned around on his hands and knees on the sofa and arched his back for me. I made him put his head down and arch his back even more. His now red asshole was now open but could still pucker. I kissed and licked on it again before easing my dick back into it and stroking him from the back. I loved the way his butt cheeks jiggled whenever I pounded him. And his high-pitched moaning made me want to fuck him harder so I did. I grabbed onto him and fucked the hell out of him. Doggystyle was my favorite position when fucking a man so I got carried away. I expected him to reach back and try to stop me but he let me fuck him as hard as I wanted to.
“Choke me again, nigga,” he told me with a serious tone in his voice. “Fuck this ass and choke me!”
I put my arm around his neck and fucked him harder. I dug balls deep into that ass. I was caught off-guard when he matched my rhythm and threw that ass back. And the squishy noises his ass was making was like music to my ears. It was almost like the sound Traci’s pussy would make after it got all creamy. He’d even gotten my dick creamed up, which drove me wild.
I put my right foot by his head and bent over so that I could fuck him harder. I stopped choking him with my biceps and he gasped for air but now I was making him run out of breath by fucking him so hard. When he started kissing and sucking on my big toe, I felt an orgasm coming. So I snatched my dick out of his gaping ass and made him get down on the floor. I jacked off over him until I caught my nut.
“Oh fuck,” I hollered out. “Get this cum, boy. Fuck!”
For the first time in my life, my dick actually shot out cum instead of oozing it out. It squirted all over his face and neck. I actually lost my balance and fell back onto the sofa as more cum rolled out of my dick. I’d never experienced anything like that before. My own asshole was clenching up and my toes were curled up tight. Trey massaged my balls and started sucking on my sensitive dick which made me go crazier. I kept convulsing and trying to calm my body but couldn’t. Like I said, that shit had never happened before.
“You motherfucker,” I managed to say, causing him to laugh. “Fuck you for that shit. Damn!”
“You’re the one that wanted to do it,” he said with a smile. “Now let me put that dick back in so I can cum.” He climbed up on my lap and grabbed my dick so that he could sit down on it. He moaned and clenched up as his asshole took my dick into it. His dick released more precum and he used it to jackoff with. “Help me get this nut, baby.”
“Bust it on my chest. Get that nut, Trey.” I sucked and bit his nipples while he did his thing.
He rode me harder and faster while jacking his dick. After a good five minutes, he started moaning and jacking his dick harder. He then tilted his head back and told me, “I’m gonna nut! Ah fuck, Dex!”
His body jolted forward as his dick shot out strong shots of nut, hitting my chest hard. His cum was so thick and pretty as it rolled down my chest to my abs. I tried to grab his dick and jack him off more but he stopped me because it was too sensitive. He kissed me again before slowly pulling up and off my dick. We stood up from the sofa and just stared at each other.
“So, does that cover the cost?” he asked me with a cute smile.
“Hell yes,” I told him with a laugh. “That more than covers it. You put on a good show.”
“Show? Nigga, that wasn’t a show. That shit blew my mind. I mean, at first I wasn’t likin’ it and it hurt like a bitch but when you choked me and manhandled me…bruh I don’t know how to even explain it. I’ve never considered myself gay but that was more intense than anything I’ve ever done with a female.”
“You really like it? For real?”
“I loved it. My asshole is so sore right now but I did enjoy it. I can’t even lie, man. And I could tell you really missed fuckin’ niggas.”
“Yeah, I’ve never came that hard before. It really was intense.”
“My sister never made you cum like that?”
I laughed again and told him, “Hell no. Not even close.”
“This shit is crazy. You got me thinkin’ if any of my homeboys were ever on the low. This shit is a trip.”
“Yeah, there’s nothing like two men doing something this intimate together. It is a wild ride, especially the first time. What I wanna know is if this is the only time me and you will do it. My offer is still on the table. You can stay here as long as you want, Trey.”
He grabbed my now semi-hard dick and asked, “As long as I want?”
“Yes.”
“Damn, I can’t argue with that.” He pushed me back down onto the sofa and climbed on top of me again.
“What are you doing?”
“My ass might be sore as fuck, but I wanna nut again before I go to sleep. And I want you to nut in my ass this time, bruh.”
“I got you, baby. I got you.”
We fucked again and that time I nutted in his ass and he busted another nut on my chest. We took a long hot shower together and actually spent the night in the bed I shared with his sister. After that night, things between me and him changed. Traci assumed that he and I had finally put our differences aside. I did feel some guilt about fucking my wife’s brother behind her back but she wanted me to help him out so that he could stay out of trouble. We converted the basement into a room for him and I’d sometimes sneak down there late at night and fuck him. Other times we’d tell Traci that we were going to the gym and would fuck in my truck. We had our own thing and I couldn’t complain about it. The arrangement had become beneficial to both of us, so there was no telling how long it would go on.
[Disclaimer]: Pictures used do not reflect the sexuality or personality of people in the pictures. They only serve as visual examples of the characters.
© D.A. Morrison 2016
