Wyatt Teaches Owen to Bottom

*********This is complete fantasy. All characters are 18+. This is different from my usual stories. I wrote this a few years back and is about a committed couple, Owen and Wyatt, in an established relationship. They are having a steamy session where Owen, the top in the relationship, is on the receiving end of some anal fun for the first time. Please leave comments.***********

Wyatt adjusted his position on the bed as he lowered his hand down the back of Owen's thigh and across his hair covered right ass cheek. Owen was on his back with his ankles raised level with his waist. His ankles were tied to the headboard of the bed. His most vulnerable area was exposed. His pink hair rimmed hole was exposed for Wyatt to see. He was super nervous about his hole being exposed. He wondered if Wyatt felt this exposed when he would pry Wyatt's ass cheeks open before fucking him.

Wyatt let his finger circle Owen's ring. He felt Owen's hole clench at the touch. Wyatt rubbed his hand over the black hair on Owen's chest and said "Baby, it's okay. I think someone's nervous about their bussy getting used."

Owen gave a small grin and nodded.

Wyatt picked up the lube from the nightstand which was sitting next to two different size dildos. After thoroughly lubing his hand and pouring some over Owen's hole he asked, "Are you ready for my finger?"

Owen said "I guess. Go slow, okay"

Wyatt smirked "I see. Now that your holes the one getting stretched open you start worrying about going slow." He held up his middle finger "It's just a finger, babe. Those will stretch you out a lot more." He jerked his head over at the dildos.

Owen swallowed hard. He enjoyed sitting back in bed, jacking his dick, while watching Wyatt ride the dildos. He never thought about it when he made Wyatt fuck himself with the silicon dicks, but they were big. And the dildos were still smaller then his own eight-inch penis.

He took a deep inhale as he felt Wyatt's finger enter him. He started clenching.

Wyatt continued rubbing Owens chest in a calming manner and whispered "baby, you can't clench. It'll make it hurt more. Unless you say no, I'm still fucking your hole no matter how much you clench."

Owen continued taking labored breaths until Wyatt's finger was all the way in. He twirled his finger around until he hit Owen's prostate which caused Owen to let out a whine and his dick begin to chub.

Wyatt reached down and ran his fingertip over Owen's shaft and up over his frenulum.

Without warning he pulled his finger out of Owen's butthole with a popping sound and put his lube covered finger deep into Owen's mouth instructing "taste your hole"

Owen choked and coughed trying force the finger out, but it didn't work. He tried to say "disgusting" but all that came out was "diglursping"

Wyatt said "Oh baby, this is gross? But every time I don't wanna taste mine you say I'm being a whiner and that it's just your finger."

Wyatt pulled his finger out of Owen's mouth and Owen looked at him sheepishly. Wyatt reared back and picked up the smaller of the two dildos.

Owen looked scared. Wyatt rubbed his chest and said "Baby, are you okay to keep going?"

Owen nodded "Mmhmm. Umm.... I'm sorry that I give you crap about stuff in bed. Have I ever been too rough?"

Wyatt leaned over and kissed Owen "No. Its just that you're bigger than both of these dildos and sometimes you wanna go fast right from the start and if you don't go slow it hurts."

Owen looked down. He felt bad. "Wyatt, I'm so sorry. I don't deserve to ask, but please be gentle."

Wyatt nodded "of course sweetie, but after you get used to the bigger one, I'm making you use the fucking machine for thirty minutes."

Owen swallowed again as Wyatt rubbed the tip of the smaller four-inch dildo over his entrance.

Wyatt began pressing the tip in. Owen started breathing quickly and contorting his face

"Breath, breath." Wyatt said, comfortingly. "You're okay. It's just the tip. This is as wide as it gets. the hardest part is mostly the girth not the length."

Owen's hole burned and felt like it was ripping open.

Wyatt began pushing the dildo in farther and felt Owen's legs start shaking. Owen's face was in his hands, but Wyatt didn't stop pushing until Owen had taken the dildo all the way to the base.

Wyatt instructed "Okay, when I take my hand off, you're gonna hold the dildo in until I take it out. If you push it out, you're gonna get your balls smacked, do you understand?" Owen moved his hands from his face. His face was bright red with embarrassment. He nodded and said, "yes..... yes sir."

Wyatt felt a rush of pleasure in his balls as his boyfriend called him sir. For some reason. He really liked it.

Wyatt let go and he saw Owen clench his hole trying to hold it in. Wyatt watched the clock for five minutes. Sweat was running off his partner as he fought to keep the dildo inserted. Every so often when Owen adjusted his muscles, he felt the tip run against his prostate which felt different than anything he'd ever felt before. Wyatt noted the bead of precum that dribbled off Owen's dick and onto his belly.

Without warning Wyatt reached down and roughly tugged the small dildo out.

Owen let out a whimper at the shock of the dildo moving. Wyatt held it up for him and said "See. This is just a 4 inch trainer. Now let's use the 7 inch one." Owen gulped wishing he hadn't been so rough with his boyfriend. Bottoming was harder than it looked.

Wyatt lined up the 7 inch dildo with Owen's ass. He began pushing it in and Owen's legs immediately began shaking again. Halfway in Owen blurted "stop! Stop! I can't take anymore."

Wyatt stopped pushing and held the dildo in place. Owen looked into Wyatt's eyes. Owen's face was beat red and dripping with sweat. He would never tell Wyatt, but he was having to hold back tears from the pain in his rectum.

Wyatt cooed "I know sweetie. The other one was smaller, but this one is the size of a real man. Like how big your penis is." As he said this, he ran his hand over Owen's cock which he now realized was hardening and leaking.

Wyatt chuckled "Look you're precumming." This just solicited a groan from Owen. Wyatt said "baby, we can be done now. I know how hard it is to bottom when it's your first time."

Owen replied "No, keep going. I didn't realize what it's like. Wyatt I...I am so sorry."

Wyatt started stroking Owen's dick and started pushing the dildo the rest of the way. The whole time he pushed Owen's dick swelled in his hand to its full 8 inches.

Once it was all the way in Wyatt and Owen looked into each other's eyes. Owen tried to smile but Wyatt could tell it was pained. Wyatt leaned over and ordered "hold the dildo in until I set the fucking machine up."

Owen clenched and stared at the ceiling while Wyatt moved around at the end of the bed. He felt more pressure as Wyatt pushed the piston into the hole in the bottom of the dildo.

He heard the click of a camera and looked down "what are you doing?" Wyatt crawled up and put his phone in Owen's face. On the screen was a picture of Owen's hairy ass with the dildo and piston sticking out. His ring was stretched wide and was straining pink.

Owen begged "Baby, delete that. It is so humiliating." Wyatt laughed and deleted the picture.

"Alright, we are gonna let the piston fuck your pretty little ass and while you're getting fucked, I think my dick needs some attention." Wyatt glanced down at his hard dick and Owen cracked a smile. At least sucking dick would take some of his mind off the pounding in his asshole.

Wyatt looked at the machine and said, "I think a good medium speed will be good."

With a flick of the switch Wyatt watched the piston come to life, pushing the dildo in and out. Owen came to life like an animatronic figure and writhed and groaned "oh fuck. Holy motherfucker. It.....it feels fucking weird. Why....."

Wyatt laughed "I think the dildos hitting your prostate. Ever had a prostate orgasm?"

Owen shook his head.

Wyatt tapped Owen's slit and pulled off a string of clear precum. Wyatt laughed "I think you're gonna shoot a big load soon. Does my boyfriend wanna shoot a big load?"

Owen nodded furiously. Wyatt gave Owen's shaft a shake and then thwopped it down onto Owen's belly "Don't worry, baby. The fucker will give a fat orgasm. One rule. Hands off your dick. You only come from the dildo. But right now, I need some BJ."

Wyatt straddled Owen's chest and began fucking Owen's mouth. Owen wasn't used to Wyatt taking such charge. Wyatt was skull fucking him. He couldn't maintain focus between the piston and dildo in his ass and Wyatt's hard member going down into his throat.

Owen gagged which prompted Wyatt to pull his dick out for just a second before Wyatt slapped his face and shoving his cock back in saying "back in. No one told you to stop." Wyatt was forcing it in all the way until Owen's beard covered chin hit his nuts.

He felt a weird feeling in his nuts. He was close. It was the dildo hitting his prostate. He tensed up. He wanted to prolong the feeling. He wouldn't lose control and slut-out like a little whore.

Wyatt ordered "look up. Show me those pretty eyes."

Owen looked up. He was so close. Wyatt felt him squirming and knew what was coming.

Owen had never felt this. If he had been jerking off and edging, he would've stopped so that he wouldn't cum. The dildo hitting his prostate was about make him cum hands-free for the first time.

He felt it. Suddenly he was shooting a load with the force of a fire hose. He tried to say he was cumming, but it was impossible with Wyatt's boner in his mouth.

Wyatt felt the cum explosion on his back and joined Owen in orgasm soon after.

Owen tried pull his mouth off as the globs of cum shot down his throat, but Wyatt held his head and said, "No, no no. Swallow my load baby. I went to the trouble of giving you this load. Don't you waste a drop."

Once Owen had swallowed twice, Wyatt pulled his slobbery dick out and turned off the fucking machine. Owen sat silently panting for a minute while two more globs of cum dribbled from his dick.

Wyatt untied Owen's legs and pulled the dildo out. Wyatt noted Owen's hole didn't clench near as tight as it used to.

As they cuddled Owen said "I never knew that it hurt that much. Please forgive me. I was such a douche bag when you asked me to go slow."

Wyatt replied "of course I forgive you. And don't worry, I think we're gonna start doing this once a month to make sure you don't forget what it's like to be the bottom."

Owen gulped hoping Wyatt was kidding. Wyatt most certainly was not.......