Dress Rehearsal

It had been a tight month and that's what had decided him. His rent was due – and he'd make it – but he wouldn't be eating for the rest of the week. Male escort work beckoned...

He knew enough about the industry though to know that if he wanted to do well, he'd need to be available to male clients or he just wouldn't make it in his city. So, here he was sitting in his car, in front of the house of someone he'd met on a dating website...

Single Guy 50s...horny...looking for men 25 to 45 for casual but safe sex only...drop me a line and lets see what happens from there. Beginners extremely welcome...

They had chatted for weeks, discussed what fantasies he was considering – and to be honest, he was curious about having a man – and there was a fair idea of what could...would...happen when the meeting finally took place. His mouth was dry from the nerves...

Minutes passed...and before he knew it, he was standing at the door. The house was a villa, probably early 1900s, surrounded by hedges and very discreet. The door opened.

First impressions count they say...he was tall, slim, greying and in his 50s as he'd said in the ad. Nice smile, friendly voice..."Come on in," he said "My name's Jason."

He followed Jason through the house and into the bedroom. A heater blazed out warming the room which was stylishly decorated. Tasteful pictures of naked men with muscled physiques adorned the walls...the floor was polished wood and the bed was covered with a rich purple spread. The walls were cream in shade and the curtains – which Jason began to close – matched the bed linen.

Jason moved towards him and began to undress him – no further conversation seemed necessary. He lifted up his arms to allow his t-shirt to be removed, still surprised in his own mind that he was trying this. "Nothing ventured, nothing gained." he thought to himself.

The older man reached for his trousers, and he stopped him for a moment...eyes met...he spoke. "Allow me..."

He stepped back and undid his belt, slipping it out of the loops and letting it drop to the floor. Button, zipper, both were undone, and he began to ease his jeans down. His cock was bulging against his briefs – whatever nerves he had were being overtaken by excitement. Jason began to remove his own clothing

In moments they both stood there, briefs only, and then they stepped together. Jason slipped fingers into the waistline and removed his briefs...his cock sprang forward, hands slipped around to allow fingers to caress the hard shaft...he gasped suddenly at the shot of pleasure that went through him. Jason pushed his own briefs to the floor and they were naked.

Jason waited no longer...he knelt in front of the younger man and moved his head forward. Tongue started licking the hard shaft as hands explored what they could reach...chest, butt, legs...he just stood there, lost in the sensation of it – Jason really knew what he was doing...

Just when he thought he couldn't take it any longer, Jason slowly slipped his lips off his shaft and stood - "Lets get into bed, lover". He followed on...

Covers were pulled back, and the two men eased into bed. For a few moments they lay apart, looking at each other's bodies, then he moved closer to his mentor and began to kiss....

Passion and desire heated him - he was surprised that he could feel this with another man. He began to move his kisses down Jason's body...rolling the older man onto his back he kissed his way down his chest, playing with Jason's nipples with his tongue...

Chest, ribs, tummy, he continued down, knowing what would be coming soon and nervous about it, but determined to give it a try. He felt Jason's hard cock pressing into him and as he got closer, he glanced up at the older man's face. Eyes were closed and he looked as though he was lost in the pleasure of what was happening.

He felt the hard shaft against his face, then ran his tongue from its base to the tip...Jason gasped in pleasure...then he took it into his mouth and began to slide his lips back and forth along it. Jason began to mutter..."Ohhhhh, that's good...you sure...you've never done this...before...?"

He was enjoying this...much to his surprise. It felt great to be able to make another man feel like this.

He kept sucking, running his lips as far down the shaft as he could cope with right back to where he was only just holding the head. He kept at it, his tongue caressing the shaft underneath as he sucked. Jason moved his hands to hold them in his hair..."Mmmmmmmmmmmmmm" he moaned...then he said "Stop...I want to cum inside you..."

This was where the nerves really hit...he knew he had to try this...and now wanted to try this...but it still freaked him out a bit. "Don't be nervous," said Jason as he got up to change positions, "I've helped men try this the first time before...I'll be gentle on you."

He lay down on his back and watched as Jason got out lube and condoms (Safe sex only as the ad had said). Jason was as hard as a rock and he smoothed the condom onto his shaft...then some lube, then he put some lube on the tip of his cock and moved over to the bed. Taking the younger mans legs, he lifted them up as he lay close and helped him to move to the edge of the bed – Jason stood at the end, hard cock and bottle of lube ready.

He was surprised how far his legs were able to stretch back, and felt a little odd, but went with it. Then he felt Jason's shaft touch his hole...it moved back and forth to spread some lube around, with a bit more being applied...Jason put the bottle aside and looked down at him as he gently moved forward, opening the young man's arse with his cock. He let out the breath he realised he'd been holding and tried to relax as he felt the tightness of his arse being widened...

Jason slowly moved into him, and as he moved in further he leaned forward and kissed him...then he began to thrust...gently, slowly...it was sore, but not unbearable, but outweighing that was the pleasure he was feeling as the cock moved in and out...he grabbed Jason by the hips to pull him closer...ohhhh it felt good...he was surprised, but pleasantly so. Jason leaned forward and perched his knees on the bed as he thrust, leaning his chest into the younger man's – with each thrust he eased in as far as it felt comfortable, held then slipped slowly out. Thrust in, hold then out...

He was feeling the movement, and loving it, tight though he was..."Fuck me more..." he said...and Jason obliged...he pumped forward and back, more quickly, more raggedly now as his orgasm got closer...he pushed in once more and held, and cried out as his hot cum spurted...

Jason let his orgasm subside and then slowly eased out of the younger man's tight hole. They lay down side by side and kissed again.

"Well," Jason began, "did you enjoy that?"

"More than I thought I would" he replied Open for business, he thought