Straight Predicament

How had I landed myself in this predicament? I was horny, that's how.

I was horny and young and good looking and just happened to cross the wrong, kinky girl at the wrong time.

Don't get me wrong, the sex was amazing. I had met Sarah on a hookup app and we quickly hit it off and jumped into bed. She was the first woman I'd ever met who had a slightly dominant streak. She loved to break out the handcuffs, the ropes, the ball gags. She was absolutely wild.

Often times, it was too much for me to even handle! I was a pretty normal, vanilla guy, after all. But it had been several months since I moved to the city and was having a difficult time finding a steady, nice girlfriend...oh well, at least I was still having fun with Sarah once a week.

"I have to go out of town for a week for business," she had said. "And I had this fun little kinky idea in mind, would you be up for it?"

I shrugged. "Sure, what did you have in mind?" We had been hanging out in my apartment the entire weekend, drinking, fucking and having a good time.

"I want you to wear this for me." She handed me this metal and silicon looking device about the size of my thumb.

"What the hell is it?" I said, turning the thing over in my hand.

"It's a cock cage. A chastity device." She winked, grabbing my boxer briefs and tugging them down to my ankles. Her hands were so quick, I barely had time to put up a fight before she had grabbed me by the balls and started stuffing my limp cock into this thing.

"Whoa, whoa, hey! Ack! Watch it, that pinches!" I shouted, trying to get away but she had me literally by the balls. A few clicks and twists and next thing I knew, my dick was locked in the little silicon trap.

"Seriously," I asked. "What the hell is this thing?"

She smiled. "I told you, it's a chastity device. Trust me, you'll like it. You won't get to cum while I'm away, but when I get back you're going to be so horny you'll shoot a load through the ceiling!" She chuckled, hopping off the bed.

I turned my caged dick in my hand, frowning as I tugged at it slightly. "How the hell do I get it off?" I asked.

"You don't! I have the key. I'm going to take it with me." She smirked, dangling a small key in her hand as she grabbed her purse. "Don't worry, you can still pee and everything, you're just not going to be able to get very hard."

The realization of what she was suggesting suddenly hit me and I jumped up from bed, feeling the weight of the cage locked around my junk.

"Are you kidding me? No way! C'mon, give me that key, this is a little too much Sar..." She crossed the room and put her soft lips to mine, dropping a hand to my silicon encased cock and stroking my balls.

"Don't worry, baby. Just trust me."

Yep, I was young, horny and absolutely stupid.

--

It had only been 3 days and I was already going crazy. I couldn't sleep. I couldn't focus at work. I couldn't believe how incredibly difficult it was not being able to jerk off and cum just after a few days! I jiggled the lock on the chastity cage, twisting and turning the thing like some sort of depraved rubix cube, desperate to get it off.

I even tried to wrench the thing off with a pair of pliers to no avail. What was I going to do? Sarah refused to return my calls or texts. Should I call a locksmith? Yeah, right!

"She actually locked you up and took the key with her?" Tim laughed as I explained the situation to him one night after work. Tim worked in my same department and had become a pretty good friend since I had started my new job and moved into the city.

He continued to laugh as I squirmed on my stool across from him.

"Hah, tough break, buddy," He said again, his round face turning red from laughter, pounding his fist on the table. "That has to be the most hilarious thing I've ever heard."

"Dude, it's not fucking funny." I shouted, hopping off the stool and adjusting myself. "I gotta piss. Be right back." I snapped, sulking off towards the bar's bathroom, Tim still howling with laughter as I walked away.

"Asshole." I muttered to myself at the urinal as I worked to fish the cock cage out of my fly. I had hardly noticed the larger presence at the urinal next to me.

"*Ahem,*" A man coughed, my eyes quickly darting right to see a slightly older, bald man at the adjoining urinal. "Sorry, I couldn't help but overhear your conversation with your friend out there." He chuckled.

My face immediately went red and my eyes locked on the wall in front of me. "Uh, oh. Y-yeah. It's a, uh, crazy situation."

"Yeah, really sounds like it." The guy smirked. He was a much bigger guy than I was but had a slightly higher, softer voice.

"Look, don't be offended or anything," He continued, his eyes focused on the wall ahead of him as well. "But I've got some experience with these kinds of things. If you're really stuck, I could help you out. Doesn't have to be weird. Strictly professional...like a doctor, almost." He said.

Stunned, I shook my head, embarrassed. "Ah, no man, no. I don't need any help, I'll figure it out." I managed as I tugged and pawed at the cock cage.

Zipping his pants, the man nodded as he headed towards the bathroom door. "Yeah, sure. But, hey, if you get desperate, I can help you out. No pressure." He washed his hands then set a business card down on the counter and left without another word.

Goddamn, I thought. I gotta get this thing off. I zipped up and wash my hands as well, my eyes falling to the card the man had left me.

Gary Alvarez

Handyman, 24 Hours

His phone number was printed at the bottom. I sighed and scooped up the card. Well, worse comes to worse, I thought...

--

I woke up the next night from a wet dream, my hard cock straining to be freed from the cage.

"Damnit!" I groaned. "Why the hell did I ever agree to this?!" I snatched my phone from my nightstand to check the time and saw that I had missed a text from Sarah.

Oh, finally! I thought. Maybe she'll be back soon and can get me the fuck out of this thing.

SARAH: Heya, work trip got extended. I won't be back for another week. So sorry! If I get the chance, I'll mail you the key. XOXO.

WHAT. THE. HELL. Another week?! Mail me the key?! Oh my god, I could be trapped in this fucking thing forever! Forget this, I've gotta get this damn thing off my cock. I was just about to grab a pair of bolt cutters when I remembered about the card the man at bar had given me.

Fuck it, if this guy's got experience with this kind of thing, what have I got to lose?

I grabbed the card from my wallet and dialed Gary's number.

"Hello?" The soft voice answered on the other end.

"Uh, yeah, hi. My name is James. We actually met, uh, last night. In the bathroom at that bar down on 3rd street? I was the guy with the, uhm..." I stammered, beat red as I blabbed into my phone.

"Oh yeah, the skinny guy with the 'unusual situation', right?" He chuckled. I could tell he was fairly amused with my predicament.

"...yeah, that's me. Look, I know it's late but do you think you could...you know...help me out?"

There was a long pause and I began to worry I might never get this thing off my dick.

"Yeah, sure thing, bud. Come on over to my apartment and I can help you out. I'll text you the address." Gary said.

"Oh man, thanks so much. You're really helping me out of a bind here. Literally."

"Happy to help. Come on over now." Gary chuckled, hanging up. I quickly threw on a pair of pants, shirt and flip flops and bolted out the door, quickly driving across town.

--

I got to Gary's house a little after 1am, the street was completely quiet and devoid of life as I quietly navigated the footpaths to the address he sent me. I found his door and took a deep breath as I knocked, fingers absentmindedly fidgeting with my locked cock in my pants.

The door opened, a tall shadow looming just behind the doorframe, two bright eyes staring at me through the darkness.

"Hey." Gary said smoothly. "Come on in." He opened the door and I slipped inside the lowly lit apartment, hands in my pockets as I finally got a good look at the man.

He was definitely larger than me and at least 50 years old. He was at least six feet tall, I guessed, and very husky with a big belly stretching a LA Lakers t-shirt. His bald head was tan and smooth, and he had big cheeks and a large neck. A dark goatee framed his mouth, flecks of gray in the beard.

"Uh, y-yeah." I stammered, a bit intimidated by his larger size. "Sorry to get you out of bed this late but I really appreciate you helping me out."

Gary flashed a white, warm smile and put a hand on my shoulder, pulling me further into his house. "Oh hey, no problem, no problem at all." He mused as his eyes trailed down my frame, nodding to my pants.

"Well," he said. "Let's see what we're dealing with here, huh? Wanna take your pants off for me?"

My cheeks flushed as I stirred nervously in his living room, nodding as I hooked up thumbs on my waist band and slipped off my pants and underwear in one quick motion, exposing my caged cock to the much larger man.

Gary eyed my crotch carefully, placing a gentle, warm hand on my hip as he appraised my 'situation'.

"Heh. Yeah, you're really in a bind here, aren't you?" He reached out and put his hand right above my cock, running his fingers over my thin pubes before gently gripping the cock cage and turning it side to side in his hand.

I jumped, instinctively, but tried to remind myself that Gary was a professional. Like a doctor, he recalled.

"No worries, I think I can help you out. Tsk. Poor baby." He muttered, jiggling my balls slightly within the cock cage. Okay, that was a little strange, I thought. I pushed the thought aside while he continued to exam the chastity device, finally stretching upright to look me in the eye.

"Come on, let's go in the bedroom. I think you'll be more comfortable there while I do my work." He put his big hand on the back of my neck and led me to the bedroom.

"Climb up on the bed there. Get on your hands and knees, okay?" Gary told me.

Damnit, how had I landed myself in this ridiculous situation? I thought, tentatively crawling onto the large bed, ass and balls exposed to this larger man.

"Spread your legs a little more for me?" Gary asked, putting his hand on the inside of my thigh and spread my knees apart before I could even respond. He kept a hand on my thigh as he gently held the cock cage in his hand again, slowly tugging it from side to side, his warm fingers tracing over my balls, legs and taint as he looked at the appliance.

I shut my eyes and took a sharp breath. Okay, I know it had been several days since I had cum but why was my cock trying to get hard in the cage? Did this guy really need to touch my balls this much while he figured this thing out? His fingers sure were warm and he was certainly handling me with a soft, gentle touch.

I shifted my weight on the bed and Gary slid me a pillow. "Here, put your head down on this and stick your butt up, okay? That might be a little more comfortable for you..."

I nodded and turned my face, pressing my cheek against the pillow and raising my hips slightly for him to get a better look. My god, this was embarrassing.

Gary stood up and walked to his dresser, grabbing something from a drawer and returning to the side of the bed quickly. I heard what sounded like a shampoo bottle clicking open followed by a loud squirt of what I could only assume was some kind of thick liquid. I turned and looked behind me to see Gary slowly rubbing his hands together, his fingers slick with some sort of lube.

I felt a cold, slimy finger wiggle it's way between my ass cheeks and twirl around my exposed and waiting asshole. I yelped and jumped, quickly retracting my ass as I looked back at Gary with a frown.

"Hey, what the hell, man?!" I shouted, my cock suddenly shrinking back in the cage. "I thought you were going to get this thing off me?!" I cried.

Gary looked down at me, quizzically as he squired more lube into his hand, rubbing his fingers together as he shook his head.

"I never said I could get this off you, hon," He said. "Nah, you're gonna need to the key for that. Or maybe some bolt cutters or a locksmith. It's on there good and tight, baby."

I squirmed away as he pushed a finger on my taint, sliding his lubed digit back up towards my asshole before I could object.

"What?!" I cried. "If you can't get it off then what the hell are you doing?"

Gary shrugged with a grin. "What do you mean, baby? I'm going to make you cum, honey." I tried to push myself up off the bed but Gary's large hand fell to my shoulder, pushing me back into the thick comforter.

"WHAT?!" I said again. "That's not what the fuck I wanted, how is that going to help me at all?!"

Pinning me down, he slid his free hand over my ass, again worming his cool, wet finger against my hole.

"I'm gonna help you cum, honey. How long have you been stuck in this thing? Five or six days now? That's too long, baby, you gotta cum." Gently, he twirled a finger over my now puckered asshole, spreading the lube messily over it before he slid down to my balls, softly massaging my sack and my slightly exposed cock base.

"Don't worry, I'm a professional, sweetheart. I'm just gonna tickle your prostate a little and you'll cum no problem. It will feel good! Here, doesn't this feel good?" He asked, his hands expertly kneading my scrotum as I twisted on the bed.

"N-no." I lied as the big hands stroked up and down my balls. My cock throbbed painfully inside the cage as I wiggled my ass into Gary's hands slightly. He chuckled, running a hand over my ass and spreading my cheeks.

"Shh, shh, baby boy. I'm just gonna rub you just inside here," He said, tapping his thick fingertip on my twitching butthole. "And you're gonna cum. You're probably gonna cum a lot too. What do you say? Want me to keep going?" His finger dipped slightly, pressing against my ass, an involuntary moan slipping past my lips, Gary laughing.

"I'll take that as a yes. You ever had anything up your boy hole before, baby?" Gary asked as he teased my hole, playfully. I shook my head, my face still pressed into the pillow.

"No." I said, blushing.

"Okay. Might be a little tight then, I'll be gentle." He stood up, suddenly, his hands falling to his hips as he quickly pulled down his shorts to reveal a fat, semi-hard cock.

"W-what? Why are you taking your shorts off?" I managed as one hand went back to stroking my thighs and balls, his other hand stroking his own hardening dick.

"Hmm?" Gary hummed, looking down at me. "What's wrong now?" His hand now stroking his hardening dick.

"Can't...can't you just use your finger or something?" I begged, my ass waving slightly in front of him.

"Oh, no. I'm much more accurate with THIS. You won't even notice the difference, just close your eyes."

Eyes wide in terror, I went to push myself up, Gary gently pressing me back down, his big dick brushing against my ball sack as he coaxed me back down.

"Hey, hey. Relax. Don't worry baby, daddy knows what you need. I won't tell anyone. Our little secret, okay?"

Oh my god! This is really happening. Did he just call himself 'daddy'? I felt my balls tighten as my cock swelled in the chastity device. I was so fucking horny. I hadn't cum in days. I hadn't even been able to touch my own cock for almost a week.

Gary was right. I did need this.

My shoulders relaxed and my hips slumped slightly in acceptance, nodding to the large man behind me as he smiled, rubbing my back.

"There you go. I'll make you feel real good, promise." He reached down and gripped the base of his big cock, dragging the fat meat stick up past my balls and over my taint. I felt his fat cock head spread my ass cheeks as he gently slid his shaft between them, back and forth.

Another squirt from the bottle and I saw Gary's large frame lined up behind me, lubing up the tip of his dick as he winked me. Fuck me, how did I end up here?

My cock swelled as I took a sharp breath as Gary rubbed his dick on my asshole in little, slow circles. He pushed the tip in.

I jumped and my asshole clamped down, Gary holding my shoulders down as I bucked against his knob, my eyes shut tight and my chest heaving.

"It's in. It's in." Stirring his cock inside of me. "Feel it, baby? Now we just gotta find your little love spot." He said, sweetly. "Mmm, damn, I love you straight boys. Your assholes are always so tight."

I sucked in a breath as I felt Gary press his cock further into me. Holy shit, how many guys has he done this too? I should have made him wear a condom! I can't believe I was letting this big, gay man put his bare dick inside of me. Fuck! How big was that thing? It felt huge in my ass but Gary was so slow and gentle it didn't hurt nearly as much as I thought it would.

"Gonna go a little deeper now, okay?" His big hands reached down and he gripped my hips, holding me tight in place as he forcefully dug his cock deeper into my rectum.

"UGH!" I grunted, jerking under him as he slowly speared me.

"Relax, honey, just relax. We're almost there. You can take it." Gary comforted me, reaching up to rub my back as he stretched me open. I wasn't sure just how deep Gary's cock had slid into my hole, my face twisting as he shifted his weight and changed the angle of his dick in my ass.

Now Gary was rocking, gently inside my asshole, the head of his dick rubbing against...something inside of me. My cheeks flushed and my body felt warm as his gentle thrusts made me feel hotter and hotter.

"Oh fuck!" I managed, my hand reaching back to brace myself against his chubby thigh. Gary reached down and grabbed my wrist, twisting my arm to rest against my lower back and holding it there as he gently bumped against my prostate over and over again.

"Mmm yeah, there it is." Gary announced, confidently.

My breaths came quicker now, my mouth slack as my body felt so hot, warm and tingly. I was so fucking horny now. I heard someone moaning: fast, little, high-pitched squeals that sounded like a bitch in heat. Oh my god! I realized. It was me. I was the bitch in heat.

"Mmm hmm. Mmm hmm..." Gary whispered as he picked up his pace, his thrusts shallow but unrelenting.

NUDGE. NUDGE. NUDGE. NUDGE. NUDGE. His cock head massaging my prostate.

"Uh! Uh! Uh! Uh! Uh!" I moaned, bucking my hips back against his thick and persistent cock.

"How's that feel baby? You gonna cum for daddy soon? You want me to go faster? Harder?" Gary asked, his gently fucking increasing in speed slightly.

"Uh! Harder!" I begged. I sounded like a fucking whore.

"Harder. Okay, honey. Mph! Mph! Mph!" He let me arms go and gripped my ankles again thrusting his hips harder into me.

"You like that, baby? You like getting fucked by a man? Hmm? C'mon, cum for me." He urged, his big thighs now slapping against mine as I felt my balls tighten.

Fuck! I'm getting fucked by a man! I'm actually getting fucked by another man...oh FUCK! I groaned, loud and hard as my cock pulsed and released inside the cock cage, hot cum suddenly dripping out of my strained dick as Gary's dick milked my prostate.

"Yeah! Yeah, there you go baby! Mmm! You liked that, did you?" He asked, his thrusts slowing slightly as he shifted his weight behind me.

"Phew! Okay, daddy's turn to cum, okay? I'm gonna fuck you a little harder now, alright?" He warned, my balls, cock and hole all convulsed as I tried to protest.

"Wait, no..." I squeaked. "I...I didn't think you were going to cum too...?"

"Oh, yeah baby. It's only fair I get to dump a load in your ass after I helped you out, right?" Before I could say anything, Gary laid his entire body down on top of me, crushing me into the soft mattress as his smooth, fat belly pressed into my ass and back.

He looped an arm around my neck, gripping one of my shoulders in a tight headlock.