Your Kinky Boifriend

A wonderful follower recently sent me copies of the original versions of my stories, which I wrote almost a decade ago. I'm posting them here, unedited, for folks to enjoy.

Chapter One

“Why don’t you sit down, Robert.” I gestured to one of the leather armchairs across from my desk, “I think we need to get a few things straight.”

“I think I’ve made myself pretty clear,” he asserted, “I know you like other men, and I know you entertain them here on occasion.” His balled his fists nervously, clearly not used to having this kind of high stakes conversation.

I leaned back comfortably in my office chair, letting silence fill the room. I am an excellent businessman, and Robert was about to find out that negotiating with me would be much more difficult than he thought.

“It’s just…” the lad spoke again, “… things haven’t been great at work, and I’m finding myself a bit short every month.”

I waited a few more moments before speaking, “Would you like a piece of candy?” I gestured to the small box of wrapped sweets at the edge of my desk. Once again, silence permeated the room.

He took one, “I’m not asking for much, and a Man like you… I mean, you’re clearly doing well for yourself and I’m only asking for enough to-“

“I’m not going to pay you.” I interrupted, “I’ve got all the cards Robert.”

“There are photos,” he dropped a small envelope onto my desk, “I took them from my porch. I-I’m no bigot, but we live in a pretty conservative neighborhood. The housing committee-“

“First of all,” I interrupted again, “What you are accusing me of is having a completely legal relationship with another adult male.”

Robert’s eyes dropped to the floor.

“Secondly,” I continued, “What you are attempting to do, rather poorly I might add, is blackmail. That’s a serious crime Robert.”

I enjoyed the mixture of shame and guilt that bloomed across the young man’s face. He was very attractive – Masculine, well built, and in his late twenties. I’d seen him working outside, his well-muscled rear flexing beautifully as he tended to his yard. I bet it smelled heavenly…

“Thirdly,” I pointed up to a vase sitting atop my bookshelf, “I find it’s useful to record all my potential business meetings. I’ve got you hook, line, and sinker.”

The color drained from his face, “Shit, Tom…” he shuffled uncomfortably in his chair. “I… How do I make this go away?”

I chuckled, “Son, a real Man can’t take back his words.” I leaned forward to punctuate my point, “So the real question is do you want to go to jail, or do you want to settle this without Johnny-law?” I already knew his answer, but I waited patiently for him to admit defeat.

He looked at me cautiously, “What do you want?”

Our kiss was sweet; laced with the sugary taste of candy. Robert had been a good boy so far – every night for a week he’d joined me in my living room at 8PM sharp for our ‘goodnight’ kiss.

I pushed him back against the wall, asserting my dominance without hurting him. A small gasp escaped his lips before I covered them again, my tongue exploring his mouth. At first he had shrunk away from me, but the past two nights he’d returned my advances almost willingly.

“Well, well,” I pulled back far enough to gaze into his confused eyes, “Seems like you’re enjoying yourself tonight, Robert.”

The boy was bright red, and ever so slightly short of breath. “I d-don’t swing that way Tom, this is just about paying you back.” He swirled the piece of hard candy I’d given him to the other side of his mouth.

“Then why are you blushing?” I snickered, “I think these nightly kisses are starting to grow on you.”

I began to kiss him again, enjoying the delicious head rush that was his scent. I only stood about an inch taller than Robert, but the power I held over him was intoxicating. I was approaching forty, and I knew the psychological effect my older body had on him. I was fit, in my prime, successful – things even a ‘straight’ boy like him couldn’t ignore.

“You’re so sexy,” I pulled back again, “How come there’s no woman in your life Robert?”

It was as if I’d slapped him in the face. It took him a moment to respond, “A-are we done for tonight?”

I gestured to the door, “For tonight,” I handed him another hard candy, “Remember to suck on this before you come over, I like the way it makes you taste.”

And just like that, he was gone. It was a fun little game I’d devised for us, and the boy had been so eager to avoid getting the law involved. I sat down back down in my study, whisky in hand, and looked at the contract we’d written out.

“If kissing your lips makes you blush,” I mused to myself, “I wonder what you’ll do when I kiss your hole.”

Chapter Two

I swirled my tongue around Robert’s open mouth, pushing him further down onto the couch.

“Mmmhh…” he groaned. I could feel an erection under his jeans. It had been several weeks since we began our bargain, and I could tell his body was reacting just how I wanted.

I pulled back, “You sure moan a lot just from being kissed,” I chuckled, “Straight boy like you starting to like it?”

His face turned bright red, “I-i…” He seemed lost in thought, “It’s a bit of a head rush, that’s all.”

My hand wandered through his hair, “Must be pretty embarrassing for you, comin’ to kiss me every night.” I laid my trap slowly, “A whole year of kisses, a whole year of kissin’ nobody but me.”

We locked lips again as I conquered his mouth. For the next 11 months it belonged to me, and there was nothing Robert could do about it.

“About that,” he pulled back, “A year is a really long time.”

“Not for me,” I grinned, “I can’t get enough of these sweet lips.”

He looked almost pained, “Is there maybe… something else I could do?” He swirled a piece of hard candy around his mouth absentmindedly, “Maybe shave off a month or two?”

I locked eyes with the lad, “There’s one or two things I might consider…” I slipped a hand under his shirt and caressed his taught abs, “A boy like you has many delights to offer.”

The next night Robert arrived on time, as always. I opened the door and let him inside.

“I’ll do it.” He shifted from side to side, uncomfortably. “I get a month off my contract, right?”

I caressed his cheek, “Sure boy, one month off your contract.”

As we walked into my ample living room I could tell how nervous Robert was. I watched a little bead of sweat race down his forehead and it took everything I had not to simply knock the boy over and ravish him. All in good time.

“Pull down your pants,” I directed, “I want to see the goods.”

Robert slowly complied. He pulled of his gym shorts and boxers, revealing his manhood to my lusty eyes.

“Nice,” I cocked my head to the side, “But those aren’t the goods I’m interested in.”

The boy blushed, slowly turning around. The cheeks of his ass were round and firm with only a very light dusting of hair. It was just how I’d imagined it.

“That’s a fine ass, boy,” I cupped his cheeks from behind, “It looks mighty delicious.”

“Y-you’re just gonna kiss it, right?” He turned around, “That was the deal.”

“That was the deal,” I assured him, “Now come over here.” I took his hand and led him around to the back of the couch. “Bend over like a good boy.”

Robert was trembling as he leaned over the back of the couch, exposing his rump. I rubbed his lower back soothingly, enjoying his moment of complete submission. That’s when I saw it, his little rosebud.

It was pink, “That’s a pretty pucker boy,” I knelt down to get a whiff of his scent. “It’s begging to be kissed.”

“Just kisses though,” Robert chimed in, “That’s what we agreed.”

I cupped the boy’s soft nuts in my hand, “I always keep my word boy, now keep quite while I have a taste.”

I engulfed his virgin pucker in a wet kiss, my tongue exploring the boy’s soft ring, ridge by ridge. He smelled of innocence and fear, a heady perfume of possibilities. I wanted to show him the pleasure of submission – the toe-curling delights only his unexplored pucker could provide.

“Wow,” The boy let out low moan, “That’s… interesting.”

With one final sloppy kiss, my mouth released his pucker. Much to my delight, I noticed the boy’s sex had begun to inflate. This ‘straight’ stud had no idea what was in store for him.

I stood up, “I think that’s enough for tonight.” I handed him another hard candy, “Here, take this for being so sweet.”

He blushed and quickly pulled his clothes back on. “I’ll see you tomorrow night Tom.”

“Yes,” I grinned, “I can’t wait.”

Chapter Three

“F-fuck,” Robert exhaled as I swirled my tongue around his delectable pucker. In the nine nights since I’d begun sampling his ass the boy had gone from grunts of disgust to sharp inhales and muffled moans of pleasure.

I came up for air, “You taste sweeter every night,” I kissed his left cheek, “And it looks like you’re starting to thoroughly enjoy yourself.”

The boy’s cock was fully engorged and I watched as tiny droplets of pre leaked from his tip. His five and a half inches were hardly a mouthful, and made his glistening pucker an even more tempting target.

“You look so small,” I ran a finger along his dainty length, “Maybe that’s why you don’t have a girlfriend.”

He tried to pull away, “Dude, that’s not on the table. You said–”

“Where are you going?” I interrupted, “I’ve still got 5 minutes on the clock.”

Robert paused before re-assuming the position, “Just… just get it over with then.”

I reached between his legs with both my arms, spreading his thighs with my biceps. My forearms wrapped around and locked his hips open by pressing on his lower back. His pucker twinged with fear as I blew cold air against it.

“I just think with a cock that small,” I toyed with the boy’s pride, “You would want to play-up your other… assets.” I chuckled as he hid his face in his hands, “Now why don’t you suck on your candy like a good boy? I’ve got some work to do.”

I shoved my tongue deep into his hole, trying to get him as wet as possible. When he walked away each night I liked to think about my saliva dripping out of him – keeping him wet all night long.

“Oh, shit,” Robert panted, “Mmmmm…” His moans and sighs were accentuated by the sounds of him suckling on the hard candy I insisted he enjoy while I had my fun.

“It won’t be long now,” I thought, “He can’t hold out much longer.”

“It’s a very simple offer, Robert,” I explained, “What do you think?”

The boy was pulling up his gym shorts after another of our nightly sessions. He was rock hard from my tonguing, his inner thighs and cheeks moist with saliva.

“Just one month?” he asked, clearly unsure about my offer.

“That’s right, instead of the seven months you still owe me.” I handed him a candy and spoke to him with complete sincerity, “It’ll be sweet. I haven’t hurt or harmed you yet, have I?” I placed a hand on the boy’s shoulder, “You may even like it.”

“But I’m not gay,” He looked up at me, “I like pussy, I think about it all the time and-”

I interrupted, “Have you even been with a woman?”

He blushed, “Well I-”

“That’s what I thought,” I continued, “And what woman would want fucked by that little thing?”

It was like I had punched him in the gut, “J-just one more month?”

“I promise,” I moved closer to the boy, pulling him in for a soft kiss, “Give me that cherry, and I’ll make it sing.”

He blushed bright red. As our lips locked I could taste the sugary sweetness of his nightly hard candy. I wanted to bend him over the couch again – show him what it felt like to give in to a real Man.

“Okay…” He admitted defeat. “I’ll do it.”

I continued to hold him, “No condoms, I want your cherry all natural.”

He cringed, but nodded yes.

“And if I make you cum, you have to stay the night.” I waited for his protests.

“Okay,” He responded, “Just… Just promise you’ll go slow?”

My eight inches leapt to life in my pants, “Of course,” I squeezed the boy, “I would never hurt something so sweet.”

We stood there for a few more moments, the heat between our two bodies palpable. “Wasn’t this the kid who tried to blackmail me?” I thought, “Isn’t this the boy I’ve been blackmailing back?”

He broke our hug, “I’ll see you tomorrow then.”

“Yeah,” I came back to reality, “Remember to use the washing video. You’ll need a deeper clean.”

He grinned awkwardly before saying goodbye, “See you soon, I guess.”

“Yeah,” I grinned back, “See you soon.”

Chapter Four

The tip of my cock kissed his pucker, eager for conquest. It would be easy to just force it in, break the boi’s defenses and claim his cunt, but making him want it would be sweeter.

Robert looked up at me, his eyes full of innocence and fear, “It won’t fit.” He leaned back on my red satin sheets, oblivious to how cliché his concerns were.

I rubbed my head against his gash, “It’ll fit, we just have to stretch you out a bit first.”

The boi cringed as I spit into my hand. I slathered his hole with homemade ‘lube,’ drawing delicate circles with my index and pointer finger.

“Oohh…” Robert quivered as I began to press down. He looked dumbfounded as one of my digits sank into his quim.

“You’ve got a sweet spot in here,” I explored his bud slowly, “Only about the size of an acorn. Is it… here?”

He shuddered as I squeezed his boi-spot, completely unprepared for the sensation. “What are you doing?” His voice shook as I applied more pressure, “Wh-what is that?”

With my free hand I gathered one of his legs up and place it on my shoulder. It was a subtle, subliminal way to prepare him for the fuck. “You’ve never played with your pussy spot?” I grinned, “But yours is so sensitive. Look at how hard you are.”

Robert’s cock was fully erect and dribbling pre against his thigh – it was underwhelming next to my engorged length, and he looked almost ashamed, “Just p-put it in,” he whimpered, “Get it over with.”

“Tsk, tsk, tsk,” I spread his toes, causing him to inhale sharply, “I have to make sure this cherry is ripe before I go harvesting it.” Another of my fingers slipped inside, “And don’t forget our terms.”

He blushed, desperately trying to choke back a pleasured groan.

“That’s right,” I leaned in for a wet kiss, “If I can make you cum, you have to stay the night.”

“T-tom…?” He looked terrified, “Please p-put it in.”

I withdrew my fingers from his snatch and grabbed his other leg, hoisting it up over my shoulder. I knew how intimidating it would make Robert feel, and that hesitance was an aphrodisiac. “All right,” I grinned, “Look up at me, and don’t close your eyes.”

I pressed into his slick hole, maintaining a firm and even stare. The boi trembled, but did as he was told – keeping his eyes locked with mine. It was a total head rush.

“It doesn’t hurt?” He seemed surprised, “B-but isn’t it supposed to hur-“

I leaned forward, interrupting him with a deep kiss. I demanded attention from both of his holes – his cunny stretching to accommodate my girth, and his lips parting to accept my tongue. He trembled under me, completely lost in this strange new world. I was dominating his body, and he wanted more.

My fuck strokes were gentle at first, reassuring him that he was safe. We were glued together, our slick sweat mingling on the sheets. I slowly built my pace, shifting angles to open him further. His cock was trapped between our bellies, throbbing and pulsing for lack of attention.

I slipped a hand up to his mouth, happy with how eagerly he slurped and sucked my fingers, “Your pussy’s so hot,” I nipped at his neck, “You gonna cum for me?”

“Oh god,” he moaned, all thoughts of our wager dispelled. He grabbed his cock, eagerly jerking and bucking. I sped up my pace, watching his body for the signs. It did not take long.

“Nnnnnh…” he mewled, bursting onto his own belly.

It wasn’t what I was expecting at all. Most bois I sleep with explode in ecstasy, they don’t whimper or cower from their own pleasure.

It was beautiful how innocent it felt, how completely taken off guard and genuine he was. I came hard, my knees buckling as I finished inside him.

We lay there silently, both of us catching our breath. I eventually pulled myself out of him, and sat at the edge of the bed.

“You don’t have to stay,” I didn’t know what was going on in my head, but I felt… bad? “You can go home if you want.”

I turned back to find him curled up in the fetal position. He was crying.

“Shit, Robert? Did I hurt you?” I opened his legs to look for any sign of damage.

“P-please,” he looked up at me with tear stained eyes, “C-can I stay?”

My heart broke. “Okay,” I wrapped myself around him protectively, “I’m right here.”

“Y-you were right,” His body was racked with sobs, “I-I’m a faggot.”

YOUR KINKY BOIFRIEND
 Fantasy, roleplay, and kink
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