Jack always had been curious about bi-experiences, but never had a chance to try it out. He was 30 years old and had several girlfriends. However, what drew him to trying out a gay experience was more of a power game of giving up control and being "forced" to do something forbidden. One day he even put up a craigslist, but never went through with it.
This day, he was in Atlanta on a trip and finally decided to give it a serious try. He had the hotel room to himself in the evening and put up an add on craigslist looking for a dominant top who would help a first time cocksucker find his first cock. Jack was never very athletic, but an average built and in decent shape.
There were several answers to his add, but one caught his attention because it came with a picture of a nice cock. It asked for a picture in return and what kind of things he was into. Jack was very nervous to send his first picture, but he found an older picture of himself and attached it to the email saying that he wants to ask Tim (was the name in the email) to suck him rather than just doing it.
Next thing he knew Tim replied saying he understands that Jack wants to beg to suck cock. Jack replied yes. Tim then asked if Jack was into power games, to what Jack replied that he was but nothing too crazy. Tim then asked Jack to send him a picture of his virgin ass with something in it. When Jack got that email he about came. He did not have any lube in the hotel, but used a bar of soap to lube up a pen and put it in his ass (not that it really needed much lube). Then he sent the picture addressing Tim is "Sir."
Tim's response was quick and read that he likes when his cocksuckers call him Sir, but Jack needs to shave his ass if he wanted Tim's cock in it. The thought of being fucked in the ass wasn't what Jack was thinking of initially, he thought just about a blow job, however, he replied that he'd comply. In the next email Tim asked for directions and told Jack to be in the hotel room at 6pm. Jack excitedly replied that he'd be there, but he then realized he had no lube, which he mentioned in the email. Tim's reply was that he would bring some but Jack would have to work for it.
6 o'clock came and Jack was never that nervous in his life. Next five minutes lasted like an eternity, then the knock came. Jack opened the door and saw a middle aged nice looking guy dressed in jean pants and red shirt. Tim was taller than Jack expected.
"Hi," Jack said "Hello, Jack" - answered Tim, "Mind if I come in?"
"Sure," was the reply and Tim came in with a small handbag.
"So, you never tried it?" - was the next question.
"Nope, kinda nervous about it"
"Don't worry, it'll be fun. Just remember we can stop at any time, if you are uncomfortable," said Tim.
"Ok, thank you."
"You meant to say 'Thank you, Sir'?" - smiled Tim looking directly at Jack.
"Yes, Sir."
Next, Tim sit down and put down his bag. "I have some liquor in the bag, do you want some to help things go smoothly?"
"Yes, that'd be great, Sir. I'll go get the glasses," said Jack, but what he heard next made him stop in his tracks.
"Jack, if we do this right, you need to be comfortable around me. Go get the glasses, but come back naked and offer them to me."
"Ok" - was all that Jack could say. He went to the bedroom (the suite was two room) and took off his clothes. He was nervous and excited as hell. It took him a bit to get the courage to remove his briefs. Then he got two glasses and slowly walked back into the other room.
Tim was sitting on the couch relaxed and smiled as Jack entered. "You have nice body and nice cock, Jack. Now offer me the glasses." Jack could barely speak, but managed to say "Thank you, Sir. Here are your glasses." He motioned forward to pass them, but Tim said:
"When you offer something you need to be on your knees."
"Oh... I am sorry, Sir," said Jack as he got down on his knees and offered the glasses. At that point Tim was sitting with his legs spread and Jack was in close proximity of his crotch, which was making Jack's head spin.
"That's better," said Tim smiling "I think you would be great." With that he reached into his handbag and took a bottle of whiskey out of it. As he started pouring it, Jack was standing on his knees naked watching the glasses fill up.
"Want some?" asked Tim.
"Yes, please," was Jack's reply.
"You'll have to do earn it."
"How?" meekly asked Jack.
"Well... I liked that picture of your ass, but you never showed me how you shaved it. So turn around and present your ass to me."
Jack, still on his knees, turned around with his ass towards Tim.
"Spread it and ask me to look at it."
At that point something was happening to Jack, his dick was growing and he started to feel really excited. He turned around and used his hands to spread his ass and lifted it up in the air a bit.
"Sir, please take a look at my shaved ass. I shaved it for you and I hope you find it satisfactory."
"Yes, Jack, you did a fine job. Nice ass, fucking it will be fun."
"Thank you, Sir."
Jack turned around and said "May I have a drink now?" Tim nodded. Jack crawled a bit closer to the table to get his drink. As he sipped the first drink, Jack felt alcohol going straight into his head.
"So why did you invite me here?" Tim's question caught Jack off guard.
"Um... What do you mean?"
"Well, think about it. You are naked in your needs in front of me in your hotel room. Surely there is a reason for this."
"Well, I would like to..." here Jack was trying to say the words, but it was harder than he thought "to suck your cock."
Tim smiled asking "So you want to be my cocksucker?"
"Yes, sir"
