Jack, Jack of Spades

Jackson, here. I really am named after the city I live in, which ironically was named after Andrew Jackson, a white supremacist. Friends call me Jack for short, and those I serve might call me Jackie, whenever a master is generous to gift me a proper name.

My story isn’t earthshattering or terribly unique. It is a tad bit interesting, hailing from the capital of Mississippi, of all places, especially those who don’t know the ascent into my world.

I’m Jack. I am a Jack of Spades, a nice, coded way of saying I’m a gay white bottom that proudly serve superior black men.

I’m 48 years old. Father of five, grandpa of two, once divorce, and currently married to a man this time. None of my kids are with my spouses, just three baby mamas. I’m decent-looking, average height with far more salt in my otherwise almond grains than I would like, but not vain enough yet to dye it. Weirdly, it pairs well with the meat on my bones after skipping out on the gym for the past couple of years. I still preserve a respectable shape. Respectable enough for me and my husband Eaton to maintain a twice-weekly threesome with the cute prissy blond twink from Bed, Bath, and Beyond.

Eaton doesn’t know a thing about me bottoming, much less being a Jack of Spades. Sadly, he isn’t into black guys. He isn’t racist or anything, as we got a few black friends, but black men aren’t a sexual drive for him as they are for me now.

One day, a couple of years ago, my black friend Jack and I were drinking heavily and got to watching Blacked.com on his smart TV. Although I like guys, I’m not repulsed by women, like some gay guys. And Jack freely helps me scratch that itch since guys are more of a special occasion for him than a main aim. Aside from his big black member bouncing through his basketball shorts, he kept on alluding to his horniness. Of course, you are, I rolled my eyes at the single thirty-eight-year-old going from four in the stable to none. Now that his harem had put him down after finding out about each other, I was expecting him to politely ask if I could put in a good word for him with the prissy blond twink. In certain parts of the most racist state in the Union, coupled with sexual secrecy, it isn’t like lines can freely be crossed without walls of serious repercussions being built if things go left. So, it came out of nowhere when he asked him if I would blow him like the white girl in the clip.

“Not unless you’re packing like that, buddy.” I chuckled.

Jack whipped it out. And sure enough, he was packing equal if not more than the guy on the screen getting sucked off.

Needless to say, I spent most of the afternoon and half the night on my knees taking care of my good friend Jack. While he wasn’t my first black cock, that was the day I was pretty much sold on being a black cock slut.

Jack wasn’t complaining. He knew he could get head now anytime he wanted, and being that Eaton thought I took the same stance as he did concerning black men, he was none the wiser.

Three weeks and countless blowjobs later, I was back over at Jack’s place and while I was sucking his big black cock, he started to play with my asshole through my jockstrap. When I couldn’t stand it any longer, I stood up, bent over, and told him to fuck me.

This was a total betrayal to my total top image, seeing that I’d only bottomed a handful of times while working in corporate. The last time being when I was thirty-one. The motto in that world was it wasn’t gay if it was for pay. I had an asshole of a client that had nothing better to do than dangle multi-million-dollar deals over our heads at the price of our humiliation.

He was best known to hint at persuasion, which was rumored to be a succulent blowjob. Not because he was closeted or anything. He prized himself as a high valued man, and any underling that wanted his John Hancock for a hefty commission needed to drink his essence, as water cooler talk dictated.

I was engaged for a second time after my divorce to a rich bitch that cost and arm and a leg. It ain’t gay if it’s for pay, I reminded myself through the seventh fuck of my life. And boy, did I get paid!

Jack slathered me with some special jack off grease he had on hand, and it was great! I’d gotten fucked before where it wasn’t bad. Mostly, it cut a little hole out of my soul, but this was like I had a song in my heart.

Jack and I fucked around the days Eaton and I fucked the twink, sometimes even more. Jack knew I didn’t want my cock touch, at the risk of being done for the day, if my hubby dared wanted to play a little later. Jack was perfectly happy with me being a slut for him, painting my guts and all.

After one of our sessions, I told him that I would be down in Biloxi for a few days helping my boss shore up a business deal through gambling. The next day he told me his cousin Steve was visiting from Texas, and he wanted me to meet him down there.

“He’ll call,” Jack said, grabbing his schlong in earnest, giving me a heads up about what it was all about along with his blessing.

Steve rang just as I was boarding the elevator to my hotel floor for the evening. He wanted to come over. When the balding fifty-six-year-old got there, we sat and talked a spell and started drinking from the handy stash I brought from home. Steve became very blunt after he burned through a six-pack. He flat out told me Jack told him I was his whore. He demanded details, so I humored him.

“Not a lot to tell, bud. I go over to his place, suck his cock, and then he fucks me.”

Steve required more details. I’ve caught snippets of hypnotized sissy videos to know what he was itching for me to say. “I’m your cousin Jack’s whore. I like being his whore because my name is Jack, also, and I’m a white whore named Jack for a man with a big black cock named Jack.”

I saw his bulge arched in his pants.

“Can I be frank with you, Steve?”

“Sure.” He took a gulp of his beer.  

“I shamelessly tease your cousin in jockstraps waiting for the day he orders me to strut around his place in some panties. This makes me excited and nervous all at once because I know I can’t keep them at his place, because eventually he’ll get another girlfriend or two. I can’t keep them at home, because I got a husband to think about, and together we got our own whore who also thinks I’m a total top, too.”

“Go on.” Steve ordered.

“If Jack orders me to wear panties, I worry about where the hell I’m going to hide them. And if I slip up and get caught wearing them, I’ll have to try to explain them away to my husband.”

“Continue.”

“I suck Jack’s dick as many times as he likes. I love it when the bastard brushes my teeth with his big black cock, but I hate it when he comes in my mouth.”

“Why?”

“I love his taste, but I love it even more when he buries his load deep inside my ass like the whorish slut I am, like that’s where it belongs. Right in my man-womb. And you know what’s worse than that, Steve? If I can’t push Jack’s load out of my ass while I’m at his place, it’ll seep out onto my pants while I’m driving, and no matter how hard I clench, I can’t always hold it in until I get over to the truck stop over by the bypass to take a quick shower before I get home to my husband. Sometimes when I forget to wash both spare pair of pants, I have to stick around and wash them there or at the laundromat nearby and go back to take a shower, so I don’t have any trace of Jack left anywhere on me.”

Steve shifted his cock down his leg.

“The way I pay special attention to my ass in the showers, all the truckers and their whores know I’ve just come from thoroughly being fucked. And when they shoot their shot, to get their chance, to do so, too, I ignore them. Not because I don’t hunger for more cock or worry about my husband. No. I went fifteen years un-fucked before I became Jack’s whore, and I want to remind myself that I am his whore.”

His cock shot through his pants, causing me to get pretty horned myself. Slut mode kicking in, as I smiled and pointed at his crotch. “You seem to be enjoying the details.”

Steve chuckled. “Yeah, I got that way after picturing you in some panties.”

Without any hesitation, I stood up and dropped my shorts to reveal that I was wearing panties. They weren’t much, just something I daringly bought at the dollar store in D’Iberville on my way in. I figured if I couldn’t wear them at home for Jack, I might surprise his cousin with them.

His eyes damn near popped out of his sockets like I was a twenty-year-old model with a pleasing bubble butt sporting some Victoria’s Secrets.

“Man, I know some brothas that would love to get some of that, including me.”

I looked at him. “Oh really, including you, huh? And who are these other guys you’re trying to whore me off to?”

“Just some of my homies. Men who’ve been married to bats so long that their wives confused old for dead, and others not caring about how their rooster crows as long as it ain’t in their face. You game?”

“Yeah,” I smiled apprehensively. With both hands, I could still count the number of cocks that had been invited into both my chambers and none of them were more than one at a time.

Steve beamed, stood up, and dropped his pants. Lo and behold, popped out the biggest, most beautiful cock I’d ever laid eyes on, on and off screen. He took it in his right hand and said, “Then practice on this, you slut.”

I couldn’t take my eyes off the sheathed thing as he barreled towards me. He spun me around and started to feel on my ass. “I want to take you now, slut.”

I immediately spun around and sat on the second queen-sized bed to take as much as his monster as I could as I sucked furiously, stopping on occasion to give it a good lick and jack. I was in love with huge black cock and loved having another one in my mouth.

Ten minutes or so later, Steve shot a huge load down my throat. When he was done, he looked down at me and said, “So, how did it taste, slut?”

I beamed. “Delicious! I loved every second of it.”

Pleased, he asked, “What would you say if I asked you to be my little whore from now on?”

I thought for a minute, and asked naively, as if I hadn’t already signed on the dotted line. “What would that mean exactly? What would I have to do, Steve?”

Steve told me it would mean blowjobs for him and his buddies and doing whatever else they wanted. “You’ll have an important job, Jackie. Roughly, you’ll just be a receptacle for any of our ejaculates,” he said professionally.

I loved the idea of being a dirty little whore for a bunch of black guys, so I agreed. I got so excited I started to do a little happy dance, forgetting that below the belt I was in nothing more than my panties.

I saw his cock hardened again, so I told him. “I want you to take me like a little slut right now, please.”

As I got on all fours on the bed, Steve ripped my panties, and then rammed the hell out of my ass with the lube I left on the nightstand for thirty minutes. After he was done filling me to the brim, he got dressed and left, telling me I would be having some black visitors very soon. He told me to be a good little slut and do whatever they wanted. He told me to make him proud.  

I fell asleep.

I spent the next day frustrated that I hadn’t heard from anybody. I was this close to calling Steve and Jack, but then I decided I was going to pour me a drink for the evening, take me a nap, and get in on some of the casino action over into the night.

I’d gotten quite comfortable with my drink in hand a couple of hours after dusk when there was a knock at my hotel door. I answered it, expecting to send whoever on their way when I was met by an older, tall black man in a suit coat. He said Steve told him to come get me. He said his buddy was getting married tomorrow and they wanted to party before he did.

I threw on some clothes and walked out to the car with him. The guy explained along the way to play it cool and play it by ear. I was a little intimidated. I was horny, but I was realistic, too. It wasn’t like I was some ultra-fit, twenty-something throwing myself to the wolves. I was shy of fifty and overweight for Christ sakes! They’d rented a stretched limo and there were at least ten big black guys inside, ranging from chalk white to midnight black and everything north and south of a brown paper bag shade. The three things I caught right away was that all of them were older than me, bigger than me, and not a one was sober.

Even their limo driver, another black guy, was huge. As I gave them a good look, I casually mentioned that whatever girl those lucky studs ended up with tonight would probably not be able to walk straight for a few days after they were finished with her.

The limo burst in loud agreement, with a few of them relaying the “hurtin’” they put on their girl back in the day. One of the guys laughed, and said he was so horny he’d be willing to put a hurtin’ on a queer.

“Well, if you’re serious, pal. There’s a cheap motel right down the road if you want to take me there. As my kid’s favorite rapper says, $39.99 for that dirty ass ho.”

This got their attention. Next thing I knew, the door popped open, and they told me to get in. I jumped in, gave the driver directions to the motel, and wondered what I had gotten myself into as I counted the number of dicks I’d just signed up to take.

When we got there, the guy that got me paid for the room and came back to get us. Even the limo driver decided to come in for the party. They barely sat down before they all pulled out their cocks and smiled at me. Seeing all those big, towering men (not a one under 6’3) with their big black cocks (not a one under eight inches) all in one room made my slutty cock-sucking mouth water. I had to figure out some way to handle them without passing out.

One of them ordered me to kneel in front of him. When I did, he pulled my head onto his lap. I barely could get my mouth around his thick cock. He jerked his head back as I took as much of his cock as I could. I wasn’t going to let this opportunity elude me, I kept reminding myself. I wanted them all happy and coming back for more.

The two other guys came over and stood around me, stroking themselves. I reached up with one hand and grabbed another one of those huge black cocks and started stroking it for him. The rest of the guys stripped off their pants and helped me out mine, delighted that I was in my second pair of cheap panties as they started rubbing my ass. Mentioning how smooth my ass was and that it was just ripe for fucking. I looked up and said not without grease, and someone nearly trip to get some out of the bag they brought in.

Within seconds, 90s gangster rap music was blaring, and my panties were ripped with several hands pawing at my ass, rubbing my hole, caking it with an abundance of grease. One guy slowly slid his finger in my ass. It felt as big as my dick. I took a deep breath, downed another cock in my mouth and concentrated on relaxing my hole as I felt his finger go deeper into my cavity.

I felt more hands spread my ass cheeks open while the finger was still buried inside of me. Then suddenly another finger was added to the fold. I jumped, forcing the cock to slide out of my mouth. I felt my ass being stretched as they prepared it for a good fucking. He started finger fucking me harder as I moaned and took another cock in my mouth. I tried taking deep breaths as I eagerly awaited the first dick to penetrate my ass for the night.

It was agreed the groom was going to fuck me first. I had no complaints. The dude was 54, 6’7, and very easy on the eyes with his dulling black hair. Two guys lifted me up and bent me over the back of the flimsy futon. It was perfect. I could bend over with no problem and keep my feet on the floor. Some of the guys walked around to sit on the pad both to keep it steady and to grab my arms. Another guy with a pharaoh’s goatee slapped his cock in front of me and stuffed his dark meat in my mouth. I felt some of the other guys grab my legs. I felt the tip of the guy’s dick being rubbed against my ass. I held the cock in my mouth and took a deep breath around it. I wasn’t sure if I could handle this.

I felt the tip poke at the opening of my ass. I could feel my hole being stretched by the massive head. There was a popping noise associated with it, unsure if it was him penetrating me or the amount of grease we used to get me ready. At any rate, he kept going deeper and deeper as I tried to relax to take his whole cock in my ass. He was not going all the way in yet, and he kept pulling his dick slowly back out. I could feel the grease swooshing inside me as he worked on opening me up. He slowly started to fuck me with just the head. Finally, I relaxed and concentrated on sucking the cocks poking in my face.

With encouragement from his buddies, the groom finally shoved his dick all the way in. I yanked off the cock in my mouth and yelled, “Fuck!” The groom kept it buried in me as his friends called out to fuck my ass hard. He pulled all the way out and shoved it all the way in again. “Fuck!” It felt like his cock was going to shoot out of the top of my head. He filled me with that monster cock of his.

Another guy grabbed the back of my head and shoved my mouth onto his cock. I felt my ass loosen a little more as the groom started fucking me faster. His slick hands gripped my hips as he drove his master monster inside me. My mouth was full of cock and the other guys held onto my ankles, legs, and shoulders. His fucking kept getting faster and harder, and for a moment I wondered if my ass was built to take a dozen loads.

I tried to keep my concentration on the big black cock in my mouth while trying to relax my hole as it was being pounded into oblivion. Porn makes this look so damn easy, I sighed in my head. I could tell the groom was about to cum as his dick started to swell inside me. With one last thrust, he shoved his cock all the way in. I felt his balls resting against mine, and then I felt them pumping followed by his hot cum shooting inside of me, thickening the lube, making me feel weirdly full.

The groom bent over my back with this dick still in me. He grabbed my shoulders. I felt his cock pulsating more as more cum shot inside of me. My ass was overwhelmed and kicking cum back out. I head another popping noise as he pulled his cock out of my ass. I felt his cum leaking out, running down my legs. I never felt so much oozing cum in my life.

I heard one of the guys yell the Best Man was next. Before I had time to relax, push some of the cum and lube out of me, his cock was already buried inside of me. The cock wasn’t as thick as the first one but felt a lot longer. I thought the second hole was a myth. I was wrong. If there was a third, I’m quite sure the Best Man snatched that cherry, too. As I tried to stay relaxed while getting snaked, another guy came over and shoved his cock in my mouth as the Best Man began to pound my ass. Once again, I was riding a big black cock on both ends. I loved it so far. I was getting the hang of deep-throating these huge cocks and my ass began to feel right at home with all the pounding it was getting. I was getting pretty good at being on the receiving end of this group thing.

I soon felt another warm load gush inside of me and it was soon plugged with another cock. My throat was coated with cum and a lot was running down my chin. One guy couldn’t even wait for a blowjob and blasted me in the face with his load as he was cheered on by the crowd. I was the cock-loving cum-slut I never knew I could be. I knew when this got back to Steve, he would be pleased with me.

My legs began to shake. I could feel my ass full of cum. As soon as the Best Man yanked his dick out, another one was shoved right back in. It didn’t take long for this guy to shoot his wad and add his cum to the other two loads already deep inside me. One by one, they all took their turns fucking my mouth and ass, and I was full of cum from both ends.

The groom walked in front of me and started stroking his cock in my face and then leaned over to shoot another hose-fire of cum all over my face. Just as he was blasting off, the guy fucking me got too excited and shot his inside me. A few other guys who’d already taken their turns were now jacking off and shooting their loads primarily in my face, leaving a glob fest, as my ass and back wasn’t off limits either. I felt coated in all those warm loads of cum. I was covered with cum, blinded almost, dripping from everywhere.

One guy shoved his cock in front of my face. There was no way I was going to be able to get this guy’s cock in my mouth. I couldn’t even get my hands around it much less unhinge my jaw for it. My legs, ankles, and shoulders were still being held steady, but I managed to get both my hands wrapped around this guy’s cock. Even so, it stuck out at least another six inches. I’d seen big cock in the videos, but nothing like this one in front of me. This guy had to be thirteen inches and something fierce around. I glanced up through my cum-stained eyes and saw that he had a cap on. This fucking thing belonged to the limo driver.

He grinned and told me to get it nice and wet. I was hoping I could get him to shoot his load in my mouth—because I knew there was no way he was going to fit, even after getting my ass stretched out with all these other huge black dicks fucking me.

I felt my ass take another load and more cum dripping down my thighs around my ankles. A couple of more guys were now jacking off, getting ready to shoot onto my back. The limo driver took my hands off his dick and circled behind me. The guys bragged they saved the best for last. Even though I was well lubed, he lubed up some more and threatened to go balls deep in me.

I felt the other guys get a firm grip of my ankles and legs. A couple of guys grabbed my shoulders, and one grabbed the back of my head. I felt the head of the limo driver’s cock rub against my well-fucked hole. I knew my ass was wide open from being stretched out by these huge black cocks. I tried to relax to accommodate this horse cock. One of the guys told the limo driver that on the count of “three” to shove his cock in my ass and hold it there as they wanted to see his balls against mine.

The guys started counting very slowly “One…Two…Three!” And with one glorious malicious thrust, I felt I was split in two. All the feeling in my legs left and my head began to swirl. I tried to scream, to moan. I didn’t seem to have any breath to do either. I felt his hips against my ass, and I felt all those loads of cum before go deeper inside me. Two of the guys shot their loads over my back as the limo driver kept his dick inside me. Suddenly, he hauled it all the way out, and more cum started shooting out of my ass.

“Holy fuck!” I stammered, half yelling and half choking on my breath and spit.

He chuckled. Then, slowly he began sliding his cock in and out, ever taking it more than halfway out. His thrusts became deeper and harder. His balls slapped against mine with each thrust with his hairs tickling mine.

My ass throbbed from being stretched so much, but I could feel him getting ready to cum. I was ready to have his load shot inside me. He shoved his cock all the way in, but he still kept fucking me as he shot his warm creamy shot inside my ass. I felt the length of his cock pulsate with every shot, like a river of cum filling my bowels, taking my breath away.

The guy let go of my ankles and my legs almost gave way. The limo driver held me up by my hips as he kept his cock inside me. I was impaled on his cock. He finally took his cock out of my ass. I could feel his cum gush out of my ass. I knew without a doubt my hole was wider now, and one of the guys spreading my ass cheeks opened and played in all the cum.

Most of the guys got dressed and thanked me for a good time tossing bills on their way back to the limo, totaling about fifteen hundred dollars once I counted. I was too exhausted to move. I stayed there, bent over the back of the futon with my asshole blown out by the biggest creampie outside of porn, with so much drooling out and dripping down my legs. My hole slowly closed pushing more and more of the grease and cum mix out of me.

Apparently, three more black guys, who wasn’t a part of the party walked by and watched from a corner of the room, told me how hot they’d gotten watching me get fucked. Each of the remaining guys fucked my mouth and jacked off, adding their loads of cum to my face and back. I stayed in the same positioned, trying to relax enjoying the feeling of cum all over me, inside me.

I finally hobbled over to the bathroom and collapsed in the tub. I thought to fight standing up, seeing that I went in there to take a shower. Instead, in a dingy tub, I ran the bathwater and jacked off twice with my insatiable hole throbbing for more.

While this wasn’t the pivot that morphed me from a black cock slut into a spade, it certainly was my start on that sweet yellow brick road.