“No, this is the best. Hands down. This is what I dreamed of.”
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.