After their trip to the movies, Simon and Jessie went out to eat. Jessie wanted to pay - against Simons wishes. But with a quick glare, Simon let him pay. After their late lunch, they went back to Jessie's house.
'So did you have a nice time tonight?' Jessie asked.
'Yeah. Totally the most fun I've had in awhile.'
'Well, it's not over yet.' Jessie pulled Simon close to his face. (About an inch away.) 'I'm not tired and its only three 'o'clock in the afternoon let's party.'
Before Simon could reply Jessie's phone rang breaking the silence. Jessie answered,
'Hello, there's no one else that can do it? Fine I guess, but you owe me. K fine. See you then.'
Putting his phone away Simon said, 'It was work, they want me to go in for a few hours. Normally I would've said no but there paying me double. And the extra's non tax deductible. I should be back around 7 maybe 8. So chill out here, make yourself at home, and when I come back we can have some more fun.'
Simon agreed after watching TV for a few minutes decided that fun was going to be an understatement. Jessie liked being dominate in sex, but he also liked to explore sexually. So Simon quickly drove himself to the mall hoping it was still there. it was the 'it' Simon referred to was a pair if leather black pants with a matching open sleeveless vest that showed off his chest. Purchasing them he left top go back to Simon's stopping at a supermarket on they way there. When he got there, he got the house ready for his plan.
Jessie walked in the front door of his house tired after work but still energetic enough to have some 'fun.' The first thing he noticed was a piece of square lined notebook paper hanging on the ceiling fan of the living room. He noticed it was dangling on a piece of string. The note said:
Intrigued he decided to listen to the note. He walked upstairs seeing a note on the wall at the edge of the steps. It was on top of a glittery red arrow pointing to the direction of his bedroom. He read the second note:
Follow the arrow to your room.
He walked with a wondering mind. In his room he found a note with a comfy spin chair on wheels. He read the last one:
Take off all your clothes (except your socks) put the blindfold on, and sit and wait for me.
He did what the note said disrobing revealing a thick semi-erect beauty of a dick. He left his socks on as per the note - Simon's request. He was sitting in the chair for about three seconds, before he heard the door close and heavy footsteps taking a few steps closer.
'Good, you listened. Very good.' He walked behind him positioning his arms behind the chair handcuffing his wrists behind the chair with two clicks.
'Trying to be kinky huh?' Jessie said smiling.
'Who said I was just trying.' He whispered with blowing breaths behind his ear. 'close your eyes.' Jessie felt his blindfold being lifted from his face. Hearing a few footsteps then 'ok.' he opened his eyes. His expression was full of disbelief. He thought he was looking at a supernatural being. Simon was wearing the black leather outfit he purchased earlier that day, along with black cut off boots. With his think semi long black hair, and untanned skin face he almost looked like a dark angel.
Simon turned around revealing his toned ass enhanced through the pants. Jessie's dick - was long hard before he opened his eyes - now appeared to have a smear of precum out of the slit on the head of his cock. Simon walked towards Jessie smiling a sexy dark smile. He touched Jessie's shoulder with a blue-feathered tickler, which Jessie hadn't noticed before. He giggled, but Simon saw something else in his eyes. He leaned in front of his face whispering 'Shh.' His breath lightly touching his lips. 'Don't be nervous since you're a good boy I'm not gonna hit you very hard or anything.' He spoke in a soft normal voice. That seemed to calm Jessie making him relax more. Simon could see excitement in his intense lust filled eyes. he continued with the tickler then lightly tapped him on various parts of his body. He responded with some grunts and moans. Simon then got own his knees took Jessie's dick in his mouth and teased it.
'Ahh. Fuck like that.' After a few seconds, Simon got up. 'Awe. What you doin' that was perfect.' Jessie whined almost pouting.
'Just teasing you. Relax I'll go back in a minute.' He grabbed Jessie's right leg massaging it, working his way down to his foot. He massaged his sock covered foot, making Jessie groan in pleasure. Removed the sock then repeating with his left leg/foot.
By that point Jessie was so hard that his dick looked even bigger than his normal almost 10 inches. He went back to the tip of his dick noticing it was wet with his spit and more precum. He put it in his mouth sucking it some more then slowly went down deeper on it relaxing his throat. Jessie felt the most feel of his mouth and the tongue teasing the head trying to drive him wild, which it did.
He was bobbing up and down his dick like a lollipop the moist sucking slurping sounds being replaced with the shout 'I'm gonna cum!' Simon took his cum and swallowed it. 'Fuck that was perfect! K now you can take off the handcuffs.'
Simon smiled saying, 'Now who's giving the orders.'
'What the hell are you talking about? Get these fucking handcuffs off of me.' He was struggling against them to no use; they were on tighter than a dick on a virgin's ass. And they both knew how tight that was.
'Shh. Be a good boy like you've been so far.' He grabbed his head kissing him on the lips. 'The fun isn't over yet.' He spun the top of the chair around. The spin lasted around 2 and ½ turns. Then he stopped it. 'Do you want me to fuck you?'
'I want to fuck you.' Jessie emphasized the 'you.'
'Fine come on.' He undid one of the handcuffs leaving one own so he could lead him to the bed. He pushed him on cuffing him to the headboard. The click signaled it was tight. He laid down beside him slowly inching himself under Jessie.
'What the hell are you doing?'
'I'm going to fuck you.'
'I said I wanted to fuck you. '
'I know and I said fine.'
'So what the hell are you doing?'
'Oh, well I said fine. I didn't say yes.' He added, 'Don't worry you'll like it.'
'FUCK NO! I've never been fucked before'
'Aww that's cute. But you can handle it. Now you're going to feel a slight pinch.' He removed his pants which wasn't an easy thing to accomplish since they were almost skin tight. He managed taking the lube out. He lubed Jessie's tight hole shoving in 1 then 2 then 3 fingers in. Jessie moaned when the 3rd finger was inserted. He lubed his dick then before he placed it in he felt Jessie tense up.
'Shh. Now be a god boy. It'll hurt but then feel better soon. Trust me.' He shoved his 7 inch dick slowly in Jessie's ass.
'Ahh! Fuck!' he groaned as it was inching in deeper and deeper. All of the sudden he felt a hand slapping him on the chest with a loud pop. 'Ahh!'
'Relax your ass.'
After Jessie got used to it whew! Did he love riding that cock. Somehow, during the course of their anal play Simon decided to uncuff Jessie so he could sit up and bounce on his dick. He took Simon's dick very masculinely even a straight guy would've been mesmerized by the sight. They way his chest puffed in and out, as he rode up and down the way his cheeks turned red by the workout. His eyes were so inhuman as he enjoyed it tickling his anal walls.
'I'm about to cum!' Simon gasped.
'Cum in my mouth!' Jessie shouted. Jessie jumped up and sucked on his dick with moist puffs as Simon came deep down his throat. It was as if Jessie was sucking on a water hose from the backyard. Simon shouted in incoherent gasps as he lost his load in Jessie's throat. When Jessie took his mouth off Simon's dick with a loud pop Simon grabbed him forcing him to lay beside him on his back as he sucked his dick. Jessie came and Simon returned the swallowing favor. They lied beside each other catching their breaths. After a minute or two Jessie put his arm around him pulling Simon closer.
'So did you have fun?' Simon asked Jessie?
'Yeah.' Simon had the feeling Jessie was holding something back.
'What's wrong? You don't have to hold anything back.
Well I liked it but the whole anal thing.. well I enjoyed it but if I hadn't I would be mad. I'm not though, but I would appreciate it if you don't fuck me tied up again. Like if you don't fuck me in the ass while I'm restrained again. Everything else was perfect though.'
'Ok.' Simon kissed him. 'Sorry if-'
'Don't apologize. I liked it but wouldn't want to be fucked up the ass with my hands restrained. I like to be able to move around. Just don't do that part again while I'm handcuffed ok?'
'Ok.' Jessie kissed him back. 'So you really never had anything up the ass before? Simon asked.
'So I popped your cherry?'
'Yeah I guess you did.' they both laughed enjoying each other's company.