Lesson Time

"How do you use a dildo?"

I choked and spat out my drink. He slapped my back a couple times and gave me a worried look.
"God, what the hell? That's not funny, I nearly choked to death!"

"But I'm serious! I want to know."

I was shocked and still choking a bit. "Why?"

He blushed and looked down in his lap."Cause I…"

I arched an eyebrow at him urging him to continue. He whispered so quietly I had to strain my ears. "What was that?" I asked.

He swallowed hard and said a bit louder "I bought one…"

Shit. I got to admit I got a little turned on hearing him say that. And now imagining him use one…fuck I'm gonna need a cold shower later.

"Why?" I managed to ask after staring at him for what felt like ages.

"I don't know." He paused, seemingly thinking over whether or not add the next piece. "I just found the store and was curious so I went in and found it."

"But why did you buy it?" I asked, not quite following his logic. He scratched his head and darted his eyes, not once looking at me. "It just looked so…I couldn't get it out of my head. I walked around the store but I always seemed to end up back at it and without thinking I just…bought it. I don't know why really."

We sat in silence. "Why do you want to use it though?" He didn't respond. I couldn't stop myself from blurting out "You afraid you're gonna hurt yourself if you try it alone?"

He blushed and stood up, angrier then I can ever recall. "If you don't wanna tell me, then fine. I'll find someone else who won't make fun of me."

Before he stormed off I grabbed his arm and apologized "I'm sorry Dahvie. I don't know why I said that. I'll show you how to use it." Wait, what happened to just telling him?

He blushed and looked up at me with a child-like gleam and smile. "Really?"

"Sure." I can't help but agree to every thing he asks. You just can't say no to anyone that cute and eager. "Go get it and meet me in my room."

He rushed off to his room to find it and I started towards mine. I sighed out loud, why did I agree to this? Do I like torturing myself? Oh wait, I already know the answer-YES!

Oh, this is gonna suck…but not literally unfortunately. I went straight to the dresser and got out all my stuff. I couldn't decide which dildo to use though. I don't want scare him off and I'll be honest, some of what I have was intimidating especially for someone with little to no experience.

I heard him knocking on my door and quickly shoved all but one dildo in my drawer and yelled for him to come in. He stepped in cautiously and closed the door. I giggled at his actions, "Relax Dahvie, we live alone, remember? No one is gonna come barging in."

He did lose some of the tension and he chuckled nervously "Yeah, I guess that's right." Silence. We just stood, not looking at each, just shifting uncomfortably on our feet. I kinda hoped he would chicken out and never bring this up again but "So umm, let's get started I guess." There goes that hope.

"Yeah lets move to the bed." We both sat down awkwardly. "So what do you want to know?" He blushed and looked down at his lap "Well…everything I guess. All I know is that it goes in your ass and that's pretty much it." Damn this is gonna be hard. For someone as obsessed with sex as he is, it's surprising that he's basically a virgin when it comes to guys going at it. But I guess he's never really questioned it before…so why now?

"Well let's see what you bought awhile." I needed some time to think of what to do. Slowly he drew the dildo out of the bag he brought it in. He has good taste, I'll give him that. I asked if it was ok to handle it, and he put it in my hands. It was long and thick, very much like a real penis except that it was all golden. On the end was a knob and two switches. I didn't even think as I turned it on. It was on a low setting but I could feel the vibrations very clearly, it even wiggled a bit to simulate real sex.

"There's a wireless remote too," Dahvie spoke in a soft voice and handed me the remote.

Why did he want to do this anyway? He's straight…right?

I turned it off and set it on the bed before I looked up at him again. "Ok…" I started out slowly, trying to keep my voice from cracking, "before you even think of putting this inside you, you gotta prep first or it'll really hurt, especially for your first time."

"Ok…how do you do that?"

"Uh, generally you use your fingers coated in lube or if you don't have any then saliva, lotion, soap, or something like that."

He blushed lightly and looked down, his voice soft and faltering when he asked "C-can you show me?"

My face went bright red at the question and I sat frozen, simply staring at him.

His eyes seemed to resemble a puppy's as he practically begged "Please?"

I stammered for a bit, trying to form a sentence or even a thought. Finally I managed to squeak out "Um…Uh…okay. Are you sure?" Please say no, please say no, please say no I chanted like a mantra in my head.

He choked out a yes. Damn! Now I don't really have much of choice. "I have to strip you know, right?"

He looked at me with an expression I couldn't quite place, "I know." I swallowed hard and stood up. I started stripping slowly and silently praying that he would just get embarrassed and tell me to stop. I stood in just my underwear before I sat back on the bed, I'll admit I was starting to get turned on by the intimateness of the situation. "Uh, when you do this to yourself," great, there's that image in my head now, "you're gonna want to be as comfortable as possible. So lay back on the bed and take your time." I moved to the middle of the bed and laid my head on the pillow as he watched with the greatest intensity. There was that strange look in his eyes again but I ignored it.

I removed my underwear but kept them close by just in case. I felt very exposed as he studied my body, mainly focusing on the lower regions. I broke the silence by asking him to hand me the lube. He continued to stare at my body once he found it and gave it to me. I don't think I've ever felt more self-conscious before.

I looked up at him, questioning if he wanted me to continue. All he did was give a quick nod. I lubed up my fingers and dropped my hand down. Well, here goes nothing.

I took a deep breath and pushed a finger in. Dahvie's eyes widened and a blush came back to both of our faces. "Use one finger at first until you get used to it. Once you feel ready you can add more but remember to take it at your own pace."

I thrust my finger in a few more times before adding a second. I was panting a bit from the pleasure but I didn't go for my prostate just yet. I kept studying Dahvie's face to see how he reacted. His eyes never strayed from my fingers fucking my asshole. He looked amazed at what I was doing. Then I looked down at his lap and found he had nice tent going. I moaned softly at the sight and added not one but two more fingers and mercilessly thrust them into me. I saw his erection growing even more.

Is this why he asked how to use a dildo? I know he's not stupid but did he really not know or did he ask me just so he could see me like this? Wait, would that mean he likes me?

Either way, I'm gonna give him a show to remember. I moaned shamelessly and moved my free hand up to my hard dick. I started pumping myself and I saw him bite his lip. It looked like he was holding back a moan or at least trying to. He breathed heavier and just when it looked like he couldn't take it any more I stopped. I removed my fingers and sat up, wiping the sweat off my forehead.

"That's how you finger yourself. After that you can put the dildo in." He looked shocked that I had stopped. "Wait," he spoke in hurried, horny tone, "Aren't you gonna show me how to do it?"

"Why? It's just like your fingers, you slip it in then take it out when you're finished. Simple."

"But.."

I pat him on the head and smiled. "Don't worry Dahvie, you're smart. You can figure it out."

He paused then spoke again with a deep blush on his cheeks. "But I want to see you do it." His eyes now focused back on the bed spread.

Inwardly I smirked but I asked in a feigned innocent voice "Why?"

He didn't say anything but I notice his blush deepen even more. He looked as red as a cherry blow pop. I wonder just how worked up I can get him before he admits anything. I leaned forward getting into his personal space and laid my hands on his hips. I slipped my fingers under his shirt and rubbed the skin over his hip bones. I know for a fact he can't resist that.

"Jayy…" he spoke softly. "Mmm? Why do you want me to use the dildo?" He closed his eyes and bit his lip, refusing to say anything. I whispered in his ear as I nibbled on his lobe "Come on Dahvie. You can tell me, I won't bite…unless you want me too." His breathing hitched when he heard that.

I removed my hands and push his shoulders down onto the mattress. I climbed on top of him and cupped his bulge. I rubbed him slowly and asked again "Why do you want to see me use the dildo?"

"Because…" he moaned out then the words died on his lips.

I slipped my hand under his pants and teased him through his underwear. "Because why?" Man, I was enjoying this. He's such a mess right now. He thrust up into my hand, desperate for release. He was getting closer and closer. His eyes were closed shut and his mouth open just a bit, letting out a low moan. "Why Dahvie?" I asked seductively.

"Because I…got it for you." I couldn't help but smile at that. "But why do you want to see me use it?" He hesitated as I slipped my hand past his underwear to grab him. "Well?" I asked as I resumed stroking. "Tell me, baby," I laid my lips just over top of his and licked lightly at them. That finally broke him.

"When I saw it in the store all I could picture was you using it. You ramming it up your ass and pulling it out over and over again. You handcuffed to the bed while I shoved it in your ass and turned it on high. Even being in public and using the remote while you had it in."

I stroked faster as he spoke those words, then he continued on, "I've heard you in the dead of night when you think I'm asleep. I've heard you moan out my name. I've even watched you do it when we're on tour. In that store all I could see when I found that dildo was you using it while you fucked me into oblivion."

"Well then. Let's make your dream come true." I kissed him as he finally hit the edge. Once he was done I moved off of him and grabbed the golden dildo and lube. I squirted some in my hand then threw the bottle to Dahvie. "Strip and get ready" I commanded him.

Pretty much with that he was getting hard again. I watched him as he shed his clothes. My dick twitched when he was finally undressed. I smiled over at him, "Now let's put that little lesson to use. Prep yourself."

He squeezed out some lube and spread it over his fingers. Without any hesitation he shoved one in then another almost instantly. "You've done this already haven't you Dahvie?"

"Yes" he confessed, his voice became breathless as he added another finger and continued to stretch himself. "You didn't need me at all to tell you what to do."

"No, but you made a damn good teacher."

"Now let me show you what you've wanted." I spread the lube over the dildo and placed it before my entrance. When I looked up Dahvie was watching me as he fingered and stroked himself. Without warning I shoved it in as far I could get it. Both of us gasped. I shut my eyes at the feeling. Like I said before, he picked a good one.

I slid it out and back in again a few times until I found my prostate. "You ready Dahvie?"

"Yes," he moaned out, sounding as needy as ever. "Please fuck me already." I chuckled a bit at his impatience. "As you wish."

I positioned myself at his entrance and once he nodded I slid in slowly. I stopped once I was fully inside him. It was barely a minute before he told me to move. "Exactly how much have you done to yourself before this?" I asked him.

"Let's just say I have my own stash of toys and goodies. I wanted our first time to be great."

"Don't worry babe it will be." I slammed into him repeatedly, increased my pace and force. Both of us were moaning loud, then I felt his hand move to my ass. "One last thing to complete the fantasy" he told me. I briefly wondered what he meant until I felt him turn it on.

God it felt amazing. It was only on low but I could feel everything. He pushed it in just a bit further and I felt it hit my prostate. I yelled out his name and stroked him as fast as could. I held on as long as I could, determined to make him cum first. "Jayy, I'm so close."

I was about to burst so I did the only thing left I could think of. I kissed him- hard and passionately. He released into my hand and screamed my name. Then he cranked the knob on the end of dildo up to high and shoved it hard against my prostate.

I exploded into him, and called out his name over and over until I came down from my high. I pulled out and rolled over beside him. "Good first time, huh?" I panted out. "Yeah" he smiled fondly at me.

"How about we try out the handcuff idea?"

"And then go out later?"

"Of course."

"You're on."

"No, actually that will be the vibrator."