Chapter Twelve

Charlie

I took Trent’s hand and led him to my bedroom. “I’ll remove the cage, but you can’t come until I tell you, deal?”

He pursed his lips, then widened his stance. “Yeah, that’s so hot, the cage got even more uncomfortable.”

I stepped away from him, biting back a smile. He was so perfect and didn’t even know it. I’ll have to make sure to tell him. But first things first. “Strip.”

His shorts and jersey flew off in a split second and it made me appreciate the practicality of sportswear. I would never take off my tight jeans or studded belt so quickly. His big, sculpted body was a magnificent sight, but it was the blush on his cheeks and his locked cock that made him absolutely irresistible.

“Bring me that chest.” I pointed to an old box that looked straight out of a movie about pirates. I’d found it at a flea market once, refurbished and lined with soft linen. It’s been my treasure chest since then.

Trent took it off the dresser and brought it to the floor. I guided him to sit on the bed in front of it and lifted the lid.

“Oh, you have a box of cocks.”

I snorted a laugh. “Yeah, you can call it that. I was thinking of going with something smaller than a water bottle.”

“I knew I’d regret telling you that,” he said without lifting his gaze from the contents inside.

“Don’t.” I stroked his thigh, watching goosebumps break under my touch. “It tells me you’re ready and eager to experiment, not only interested in theory.”

“Yup. I’m a hands-on kinda guy.” He spread his arms, presenting himself.

I flicked his nipple, and he sucked in a breath but didn’t cover himself.

“I’ll take a few cocks out and you can tell me if you like any of them.”

Trent reached into the box. “Why does the red one look like it has scales?”

I took it away from him and set it aside. “That’s a dragon cock, and you’re not ready for that one. It’s way too wide.”

“It looks nice. And the tentacle one too. It starts really thin at the tip so we can use that soon, right?”

“Yes. For today, how about this one?” I pulled out a realistic-looking dick on the smaller and slimmer side. “I can fuck you with it.”

“Yes. But—” He frowned and I could tell his mind was going a mile a minute.

Every person I’ve been with who hadn’t been trans or had been with a trans man before, had asked invasive questions using words that sent my dysphoria reeling. Trent had never made me feel less of a man, and he’d never know how huge that was. Now, however, he was struggling with finding words.

“With the help of this.” I stood up and undressed, leaving only my baggy black cargo pants. Then I pulled them down, scattering several guitar picks from my pocket, and revealed my strap on that held a cock similar to the one in Trent’s hand.

“Oh, ouch.” He cupped his trapped dick. “Yes, please. Just let me get hard. You’re so hot, I need this thing off.”

“Praise will get you far.” I kissed him briefly and pushed him onto the bed.

He scrambled to lay in the middle, his eyes never leaving me and my cock.

“Do you use the toys on yourself?” Trent asked, his arms splayed wide as if he was ready for me to tie him up.

“The ones I showed you are new, but I rode some of the others. Sometimes, I like my ass played with. I’ll show you soon.” I knew he had questions, so I’d rather tell him straight away, less he’d be too nice to ask. “My front hole used to hurt during intercourse. It’s too tight. I use my finger only when I want to feel super stuffed when something is already in my ass. But if I’m having so much fun with you like this, I’m not even thinking of being penetrated. I’d prefer to fuck you.”

He nodded. “I want to make you feel good, but I’ll follow your instructions.”

“That’s my good Cupcake.” I danced my fingers up his thigh to his trapped cock. “When I take the cage off, do you promise you won’t touch yourself?”

He gripped the sheets and thrust up toward me. “I can’t. I haven’t jerked off for two days.”

“Try.” I climbed between his parted legs and took the chain off my neck. The key slid in easily into the padlock, and I took off the neon pink plastic, freeing Trent’s dick. I wiggled it and it thickened in my hand.

“That feels so good.” Trent rolled his hips, and hummed low from deep within his chest. Holy hell, he was purring at my touch.

“No coming until I say so, remember?” I scooped pre-cum from the tip of his cock with a finger and spread it around the head.

“But why?” His whiny tone told me he’d be a brat if not for his proper manners.

“Your orgasm will be more intense if you hold off. Trust me.”

He made a cranky noise and looked at me with a hooded gaze. “You may have to tie me up then.”

“My cheeky Cupcake.” I patted his thigh, going over the restraints I could use on him in my head. “Sit up and open your mouth wide.”

He did and watched me pull on a condom on my cock, then toss the red packet on the sheets for him to see. “I bought strawberry flavored ones hoping you’d like the taste.”

Trent licked his lips. “That’s so cool. Thanks.” The excitement painted on his face was infectious.

I stood on the bed with my feet on both sides of his hips. “Breathe through your nose and make my cock wet before I fuck you.”

He released a whimper and wrapped his full lips around my dick. A kaleidoscope of reactions passed over his face as he explored with his tongue, tasting, opening his mouth wider. Then he looked up at me with eyes filled with wonder.

I fucked into his mouth slowly, holding him by the hair.

“You look beautiful with a dick in your mouth, my Cupcake.”

He moaned, fluttering his lashes. The boy needed praise like his next breath, and I wouldn’t shy away from giving it to him.

I pulled out completely, leaving deep-throating for another day. His saliva linked his chin with my dick and I broke it with a finger, then traced his lips with it. He nuzzled my palm, then kissed the inside of it. His affection warmed my heart while the hook of pure lust sent it hammering in my chest.

“I want your ass in the air and face on the pillow.” He was so on board with what I had to give, I needed to pace myself not to push him too far at once. “Can you do that for me?” I stepped back and kneeled on the bed.

“Yes, Charlie.” He flipped effortlessly and his big, round cheeks ended up right in my face.

I kneaded them, but the muscles didn’t leave much to squeeze.

Trent swayed, and a familiar squelch stopped my movements. “Are you touching yourself?”

“No,” came a weak reply.

“Trent?” My voice was as stern as I could muster when my nose was inches from his buttcrack.

“Yes, but just a little bit.” His tone of voice told me that his newfound bratty behavior was waiting for his punishment as if it was a reward.

It was mad and brought a grin to my face. “Hands behind your back.”

He obliged, so I reached into the treasure chest and took out the set of padded handcuffs I’d purchased with him in mind. The thick leather and solid straps would keep him bound while not marking his wrists if he pulled on them.

I put his hands through the leather and he wiggled his fingers as if unable to contain his excitement. Those tiny reactions were why doing anything with Trent was so rewarding and fun. It was time he wiggled more than his fingers.

His butt was a sculpted thing of beauty—a result of Trent’s workout and the care he put to keep his body in shape. I traced the curve of his ass with my fingertips, barely grasping that it was my Cupcake offering himself to me.

“You’re so beautiful.” He’d probably heard how jacked he was often, but I remembered when he’d been unhappy with the way he looked. “So brave, and so fucking sexy.” He’d expressed his will to experiment, but following his need to explore in such an unabashed way was a testament to his embracing his newfound sexuality with open arms.

I parted his ass cheeks and buried my face between them. With a groan of satisfaction, I dragged my stubbled chin against the delicate skin around his hole. His needy whimper was the sound of the gender affirmation I craved and he gave so freely.

Trent remained still until I flicked my tongue over his rim. He rocked his hips back a fraction as he released a loud moan. I echoed his sentiment, feasting on his pucker until saliva dripped from my chin. With every lick and kiss, Trent’s whimpers grew high in note, as his thighs trembled. I ventured a tentative touch between his legs and found his cockhead wet with pre-cum.

I have to taste it.

Not yet.

“So good, Charlie…” Trent mumbled the rest into a pillow, letting me know he was ready for me to proceed.

I rested my face on his ass, lazily circling his pucker with the pad of my thumb.

“You’re doing so well, my Cupcake.” I kissed his ass cheek. “And this hole needs a thorough fucking, don’t you think?”

“Yes, please fuck me, Charlie.”

I dipped the tip of my finger into his ass and swirled, spreading my saliva. It was not enough though.

Excitement flowing through me, I jumped off the bed to show Trent my new purchase.

I dug in the bag from the sex shop and presented a bottle with a nozzle to Trent. “Especially for you, my Cupcake.”

“Strawberry flavored lube?” Trent grinned, his cheek squished to the pillow.

“Yup.” Thankfully, he liked the silly idea. Good, cause I stocked up on the stuff like I was expecting a worldwide lube shortage.

“Can I taste it?”

“One sec.” I squirted some over Trent’s crack and let it ooze down. His pucker contracted when I touched it and dipped my lubed finger past the first ring of muscle. Then I pulled it out and hovered it in front of Trent. “Now you can lick it.”

He latched onto my finger, sucking, making such lascivious sounds that heat pooled between my legs. “Fucking hell, Cupcake. You’re so hot when you’re needy like that.”

His cheeks were already flushed when he licked his lips and looked at me with fuck-me eyes. “Thank you.”

Realization struck me and I uncuffed his wrists. “Turn on your back and spread your legs.”

He flipped over and sat up. “Did I do something wrong?”

“No, my sweet Cupcake. I just want to see your gorgeous face as I fuck you until you come all over yourself.” Smirking, I pushed on his chest.

“Oh.” He grinned and laid back, lifting his legs up and to the sides. He held his thighs parted, his hands digging into the flesh covered by a dusting of hair.

Fuck, he was precious, watching with rapt attention as I slathered my cock in the strawberry lube, then slid two lubricated fingers into him.

He gasped but didn’t clench, letting me prepare him. I took out two more items I’d prepared in advance, glad I’d predicted my horny boy’s eagerness and acted accordingly.

Lifting the lube applicator, I showed it to Trent. It looked like a slim syringe but ended in a round head that slid into Trent’s hole with ease. I released the contents into my boy-toy lover and paused.

Boy-toy lover. I know what the title of my next song should be.

I looked at the muscled body of the man who submitted with eagerness and grace, not even knowing how he was ticking all my boxes and beyond.

Tossing the syringe away, I replaced it with my silicone cock covered in a strawberry-flavored condom and lube. Hopefully, the familiar scent and silliness gave Trent a semblance of comfort during exploring bedroom activities which were new to him.

My cock slid past Trent’s first ring of muscle and I paused, checking for any sign of discomfort on his face, but I found only pleasure and a soundless please on his parted lips.

“Remember to use the traffic lights system or explain if something feels off.” I glided further in, holding my silicone dick in one hand and caressing his thigh with the other.

“How about you?”

“I’ll let you know too.”

“Good, but that’s not what I meant. When you’ll be fucking me, you won’t feel…” He hesitated. “You won’t come.”

Oh, my sweet darling. “Don’t worry, Cupcake.” I lifted the slim wand vibrator I’d prepared in advance. “This slides into the pouch in front,” I said, demonstrating it. “And when I turn it on, it will stimulate my t-dick as I thrust into you.

“That’s so hot.” Trent caressed his pre-cum smeared abs, inching close to his hard-on.

“Your cock is mine, so hands off.” I gripped it at the base to drive my point across. “But flick your nipples. They’re so hard now I want to lick them. I love how sensitive they are.”

With one hand still gripping his thigh, Trent pinched his nipple with fingers of the other. “Fuck me like I’m yours, Charlie.”

Damn right I will.

Rocking my hips, I slid deeper into Trent, massaging the spot between his hole and his balls with my thumb. The view before me spiked my arousal so high, my liquid heat was staining my harness. I feasted my eyes on Trent's hole stretched for me, his thick thighs parted, his abdomen muscles tensed as his breathing grew ragged.

He was close, and I was about to catch up. I pressed the button on the wand in my harness and sent vibrations to my t-dick and the area around it.

Whoa.

I slid all the way in and gripped Trent’s hips, wanting him to feel the wand’s vibrations against his perineum. My thighs trembled as the heat in my core grew molten.

Meeting Trent’s gaze, I stroked his cock.

He threw his head back and released a low groan so sexy, it propelled me close to the edge. I pulled away and slammed into him.

“You’re gorgeous, my Cupcake. Now come on my cock.” Every thrust I made pushed the wand against my t-dick, but I remained focused on jerking Trent with my movements until the wave of arousal swept over me.

“Ah, Trent. Come with me!” I yelled as my body shook with the intensity of my orgasm.

Trent’s animalistic grunts grew high in note, and he shot a load of cum into the air. It landed on my hand, his chest, all the way to his chin.

I kept coming when I pulled out of him and braced myself on his abs.

He watched me with a thoroughly fucked expression and helped me climb him. I straddled him, licked the cum off his chin and kissed him, just as the second orgasm hit me. I mewled into the kiss, grinding on the vibe between me and his abdomen.

Trent’s arms around me let me ride the wave in the comfort of his touch. I turned the toy off and rolled off and onto my back.

“I have to say that it’s so cool you can come twice in a row.” Trent grinned and kissed my shoulder.

“I could come many times more if given a chance.”

“New challenge unlocked.” He punched the air but remained laying down.

I guess I figured out how to drain the enormous amounts of energy out of my sweet Cupcake.

“We can work towards that.”

Trent danced his fingers over my strap-on. “And a bigger cock.”

“Really? Penetration newbie and already a size queen?”

“What can I say? You rocked my world.” He flashed me his dimpled smile, so I poked him in the ribs, making him giggle. “You shouldn’t have shown me the pretty dicks in your treasure chest and then rail me so good, I forgot my name.”

I pretended to think hard about his words, but couldn’t stop smiling. “You’d look gorgeous if I railed you with the dragon cock.”

Releasing a purr, Trent glued himself to my side, his leg over mine, his heavy arm over my belly. We were sticky in lube and cum, but the warmth radiating from Trent and sheer exhaustion kept me in place. We could shower soon. Preferably when Trent’s refractory period would end.

Trent splayed his big palm over one of the scars on my chest. “Those are a testament to your bravery and fight for your happiness.” He kissed my nipple, which was not perfect in shape and not sensitive enough, but under Trent’s loving gaze seemed perfect. Then he placed kisses along the thin raised lines, hardly visible anymore. “I admire you more than you can imagine, Charlie.”

My throat closed with emotion. Unable to reply, I stroked his hair, letting a tear escape from the corner of my eye.