Chapter 17

CHAPTER SEVENTEEN

I came in his hand! Cass milked my dick absolutely dry.

How do you go home and live a normal life after that? I felt like a whole new person, with a whole new identity. My new purpose in life? To get Cass’s hands on me every chance I got.

If only I hadn’t blurted out that I was in love with him! I mean, I do love him, I always have, but now… I didn’t know how to separate those feelings. Sex and love were a mixed bag for me, I guessed. Total rookie mistake. I probably scared the piss out of him, but I couldn’t help it after the way he made me feel. Cocooned in darkness, wrapped up in his embrace, and high on pleasure—I’d never felt closer to anyone in my life.

I didn’t think he was just doing me a favor. I think Cass genuinely enjoyed himself. He came all over my bottom. When it was all warm and slippery, he pushed softly against my opening; not enough to penetrate me, but just a tease, testing my resistance. I’d almost begged him to slip it in! I was dying to know what it felt like. I was scared that it would hurt. How could it not? He was so big and thick, and I was just… unused.

Oh, God, what if I cried and humiliated myself and had to beg him to stop?

What if I came all over the bed the second he pushed inside of me? That would be just as embarrassing!

What if I freaked out and went soft?

I couldn’t risk any of those things happening! If I wanted to try to land a sophisticated older man like Cass, I had got to get my shit together. I had to know what I was doing.

Just like with anything I wanted to learn about, I had to do my research. Once a book nerd, always a book nerd. I was going to have to research butt sex.

I started with an outline for my research.

Nicky’s Guide To Gay Sex

Google keywords

Check Wikipedia for definitions and facts

Watch gay porn

Learn names for positions

Research toys and uses

Check Reddit for testimonials and personal stories

Troubleshoot pain and worst-case scenarios

Educate myself about lube

Find out how to make an older man want you

Key points on giving fellatio

Glancing over my list, I sighed and smiled. It was a good start. As I delved further into my research, I was sure the list would grow. By noon, my eyes were crossing, and I took a break to make myself a sandwich. I’ve learned a couple of important things so far, like the difference between water-based and silicone lubricants, the invention of PrEP, and that the key to giving a good blow job was using lots of spit and incorporating your hand. It seemed really complicated with way too many steps that you needed to incorporate all at once, but practice made perfect!

Maybe I could practice on a banana! If I only had one shot at this, one night with Cass, to impress him and win him over, to convince him we deserved more than one night together, I had to be good at this going into it. There was no time to learn on the job.

As I ate, I took a breather from my research and began browsing different toy sites. There were so many options! I still didn’t know what they were all used for, but it was fun to look. There were fake dicks in every size, shape, and color. Some vibrated, some moved in and out like natural motion, and some even glowed in the dark! I wasn't sure what I was planning to do with these; practice maybe? They were more lifelike than bananas. More than anything, I wanted to know what it would feel like to have a cock in my ass, stretching me and filling me, but again, I was so afraid it was going to hurt.

Cass was used to these exotic tropical men who were skilled in loving another man. At least, that's how I pictured it in my head. Cass was a sex god. He sure looked like one, anyhow, with his tall, toned body, tanned and well-maintained, his sandy hair, and hazel eyes. Ugh, total sex god.

Would he pity me? Would he look kindly on my twinky body just because he loved me and we had history? I didn’t want his pity. I wanted him to desire me. I wanted him to get hard for me. I wanted to blow his fucking mind. If only I had a clue how to do it. Ugh, back to my research.

By dinner time, I had come three times while watching research porn, and I’d purchased the cutest little neon pink vibrating dildo. It was much smaller than Cass’s monster, but I had to start somewhere. Pinky—that’s what I’d named it—didn’t feel overwhelming. I’d also bought both types of lube, a pink thong bikini bottom—wait till Cass saw me in it!—and a pair of purple board shorts that were so short and tight, they might as well be a Speedo .

I still couldn't believe I’d slept with my… what was he to me? What was I supposed to call him? I’d only ever thought of him as mine. My Cass. He'd been a father figure to me for years when I needed one. But I was grown now, and I didn't need that from him anymore.

Two dads was one too many.

What did I need from him? I still needed his love. I still needed his friendship. I craved his admiration and respect. No matter how old I got, I never wanted to stop being his little Nicky.

Just as I was about to log off, the website asked me if there was anything else I wanted to add to my cart at the last minute. I was pretty sure I had everything I needed, but then I saw a pink shirt that said ‘ Daddy’s Boy .’ Holy fuck. My light bulb went off and my dick kicked.

Daddy's Boy . It was so wicked and nasty, so taboo.

I wanted to be his boy. I already was, but I wanted him to say it to me when he was touching my cock. I wanted him to let me call him Daddy. I wanted him to spoil me and make me his most precious boy. I mean, he already did, but I wanted him to say it. I wanted him to say Nicky Boy or Nicky, my boy . Sam called me Little One or Little Nicky and it made my dick half hard, but to hear it from Cass? I'd probably combust in my pants. I'd probably never have the balls to tell them that.

How did you tell someone you've known most of your life ‘ I want to stop calling you my dad's ex and start calling you Daddy .’ It took big balls, and mine were very small, as Sam liked to remind me.

I joined my dad at the kitchen island, hopping onto the barstool beside him. Excitement thrummed in my veins, and I was practically bursting at the seams to tell him about my research, and the new things I’d bought, but I could hardly do that. My dad had dated Cass for years and had probably loved him, which made our situation awkward as fuck. And although I didn’t see anything wrong with dating an older man, I was afraid to tell my dad, as if I were doing something wrong. I hadn’t even told him I was gay!

I guessed I needed to start there.

My stomach felt swirly and sick from the nerves. What was I supposed to say? Was there a right and wrong way to do it? Did everyone who came out to their parents feel like they were about to have a heart attack? Could it be classified as a lie of omission if I intended to tell him before I died? I wiped my hands on my jeans and then balled them tight until my blunt nails dug into my palm.

“D-dad?”

He shoved a forkful of chicken into his mouth. “What’s up?” he asked as he chewed.

“I’m—there’s someone I like.” Fuck, now, he was going to ask me who. I should have left potential partners out of the equation.

“That’s great, bud. What’s her name?”

Pushing a lump of mac & cheese around my plate with my fork, I tried to stall. The longer I drew it out, the more awkward it would feel. Just do it, Nicky!

Staring down at my lap, I blurted, “I like boys.”

He stopped chewing. He set his fork down on his plate. He folded his arms on the counter. He stared at me.

“That’s—wow, okay. That’s goo—fine—um, that’s great. That, you know, you figured that out.” He grabbed desperately for his glass, chugging water as if he were choking.

Swallowing hard, I tried to fill the awkward silence with an explanation. “I didn't know when I would be ready to tell you. I’d probably never be ready,” I huffed. “But I felt this overwhelming pressure to just get it out there, done and over with. And it made me feel sick to my stomach to lie to you.”

“Nick, I'm not mad at you for being who you are or for being honest about it. I'm mad at myself for not seeing it sooner. Maybe I saw what I wanted to see,” he sighed. “What I'd hoped to see, instead of what was right in front of me all along.”

When he slid his arm around my shoulders, I lost the battle against my tears and broke down, bawling like a baby. My dad opened his brawny arms and crushed me against his chest, just like when I was little. Why was I even crying? Nobody died. Heck, it went better than I’d expected. I just felt emotional and full of adrenaline, and it was all coalescing into a tidal wave of feelings that threatened to drown me.

“I love you, dad.”

“Love you, too, bud.”

Two days later, my toys arrived! I ran straight to my room, locked my bedroom door just to be safe, and spread everything out on my bed. The neon pink prostate massager screamed at me to pick it up. I still wasn't sure exactly where my prostate was located, even after researching several diagrams. Today, I was going to find it—me and Pinky.

Tearing open a packet of the water-soluble lube, I coated the toy and then kicked off my shorts and undies and laid down on the bed with my knees bent and spread. Starting with my dick, I smeared the leftover lube around my shaft, giving it a few satisfying tugs. It began filling with blood, and I reached lower, cupping my balls. That familiar tingling warmth spread through my lower half as my dick got harder. A drop of clear fluid formed at the tip of my crown, and I smeared it around the head, making tiny electric fingers crawl up my shaft.

Closing my eyes, I leaned my head back against the pillow and just let myself feel as I explored all the ways I could make myself feel good with touch. When I was rock hard and ready, I squeezed the last bit of lube from the foil packet on my fingers and smeared it over my hole, clenching tight at the contact.

Relax, Nicky. Pretend it's Cass.

The tip of my index finger slipped inside with ease, and the feeling was indescribable. I was immediately hooked. The heat in my groin intensified, and my dick throbbed like it had a pulse. I continued to tease myself, sliding in and out, but I couldn't reach deep enough to try to find that special place inside of me.

Picking up the little pink toy, I pressed the rounded end against my rim, gradually increasing the pressure until it popped through the ring of tight muscles. The sensation was startling, and I didn't know if it hurt or felt good, but it burned in the most delicious way. I was able to slide almost half of it inside my channel before pulling it back out again.

Then I turned it on.

Holy fuck, that really shook things up !

It was like my hole loosened for it, almost like it was saying, come to Jesus.

I felt like the Energizer Bunny , like all I needed to do was charge my batteries and I just kept going and going and going. Like a horny little rabbit.

Sliding it from my body, I rubbed the bulbous tip over my balls and down my taint, drawing out my pleasure before going in for the kill.

A drop of precum released from my slit, dripping down my head, and I collected it with my finger and sucked it into my mouth. Salty, but good. Would Cass’s taste the same? My hand didn't feel as good as his had. Maybe his cum would taste even better than mine.

Sliding the toy back inside, I moved it in and out, building up the fire again, and then…

Fucking Christ! What in the blazing fireworks-inside-my-ass was that?! I brushed over the spot again, and again a holy light shone from my ass. I’d done it! I’d found the Holy Grail of butt-play pleasure. I’d found my prostate!

There was no way in hell I wouldn't come spontaneously the moment Cass knocked against my gland. There would be no stopping it and it would erupt like Old Faithful.

On my next pass, I dragged the toy slowly over my p-spot, creating the most delicious electric friction, and fireworks exploded behind my eyelids. A hot flush moved through my body like a heatwave, and milky seed pulsed from my cock.

My hand stilled, but I left Pinky inside of me, still vibrating softly, and watched in fascination as more cum dribbled from my slit. Jesus, this thing was the answer to the meaning of life, the world's most sought-after mystery. If I wasn't so late to the game, I could have made a fortune with this discovery!