Jack's First Time

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"

"Say it"

"Sir, I want to be your cocksucker." Saying that actually felt good to Jack.

"Well, Jack, you need to know that it is a privilege that you have to earn" said Tim smiling.

"I will try."

"That's good, but you forgot to say Sir, next time I'd have to punish you. Is that understood?" Jack's heart started racing.

"I am sorry, Sir, I understand."

"Good, now how will you earn the privilege?"

"I am not sure what you mean" said Jack "I'll be a good boy" as he said that he realized how stupid it sounded. Tim laughed looking at him: "That's good, but you need to show me you are deserving of being my cocksucker."

"I will try. Is there anything I can do for you?"

"I like your attitude. Have another drink" with that Tim poured some more whiskey to Jack.

"First, I want for you to be very comfortable around me and be eager to please me. There is a dildo in my bag, I want you to give me a show with it, plus it'll relax you a bit." With that he pulled out a dildo out of his bag. It looked like a medium sized dildo. He motioned it towards Jack and Jack took it. He looked it at and realized he did not have any lube.

"May I have some lube, Sir?" The answer was no.

"Sir, may I go to the bathroom to get some soap?"

"Yes, you may."

Jack stood up and ran to the bathroom. He ran the water and used the soap to lube his ass and the dildo. He brought the soap back with him and got back on his knees.

"Sir, thank you for letting me work my ass with this dildo" Jack said as he turned around and started putting the dildo into his ass. It was going pretty tight and took some effort to get it in. Alcohol started to work more and more on Jack. He started moving the dildo in and out and said: "Sir, this ass is for your pleasure tonight. I will be honored to have your balls slap against it as you fuck it hard and deep."

Tim smiled: "Wow, I am liking it, keep going." Jack kept moving the dildo in and out of his ass.

"I can not wait for your cock to enter my ass so I can show you how much I appreciate you letting me be your cocksucker. Once you fuck me, it will be my honor if you came inside me or on my face or I can swallow every drop. Would you like to have a piece of this ass, right now?"

"So you are offering me to fuck you right now, Jack?" smiled Tim.

"Yes, if you desire so, Sir."

"Wow it seems to me you are a slut, if you offer your ass to a guy you barely knew an hour ago."

Jack started to get into it as the dildo was making him feel quite good.

"I am your slut, Sir. My ass is for your pleasure."

"For a guy that never sucked cock you seem to be pretty eager. So you ever tasted your cum?"

Jack stopped fucking himself for a moment: "No."

"But you thought about it?"

"Yes, I would like to try"

"Ok, there is a butt plug in my bag, put it in your ass and crawl over to me"

Jack got the plug out of the bag and it it slid in easily.

"Thank you for letting me use your ass plug, Sir, it feels nice in my ass," said Jack with a smile. Tim replied "When I am here, you need to keep something in your ass to remind you of me. Of course, my dick will be better." Tim continued "Now I want you to unzip my pants with your mouth and listen to what I have to say."

Jack crawled to Tim's crotch and started trying to unzip his pans with his teeth by pulling the zipper. It wasn't going as smoothly as he thought it would.

"So, Jack, you are on your knees, naked with a butt plug up your ass. You are using your teeth to unzip man's pants in hopes of sucking a dick. You were just begging for me to fuck your ass and cum in your mouth. I want you to understand what just happened. Do you understand and do you want to keep going?" Tim sounded serious

Jack's reply was short "Yes, sir."

"Ok, slut, you did a fine job. Now you get your treat." With that Tim got up and unbuckled his pants.As he was undressing, Jack was on his knees looking up. A moment later Tim took off his shirt and was only in his briefs and socks.

"So you want my cock?"

"Yes, Sir. I want to show you how good of a cocksucker I am."

"I want you to make it grow in my underwear, but do not take it out."

As Jack heard that he started eagerly to kiss and lick Tim's cock through his briefs. As it began to grow, Jack intensified his efforts. He wanted to taste it and he wanted to worship it like he saw in porn movies. Tim was enjoying it and at some point he moved Jack's head away and pulled down his briefs. His cock sprang free and Jack immediately tried to lick it, but Tim stopped him.

"Did I give you permission to suck my cock, slut?"

"No, Sir, I am sorry."

"You should be," said Tim without a smile "I think it's time to show you your place and punish you."

"I am sorry I just really want to suck your cock, Sir." Jack was completely emotionally destroyed. "What can I do to make it up to you?"

"Well I can spank you, or you can lick my ass to show me how sorry you are. I'll let you choose."

"Spank me, Sir, I will be good" was Jack's reply.

"Nah... I haven't had my ass licked in a while, I am sure you wouldn't mind showing me how sorry you are." With that Tim sat on the end of the couch and raised his legs. Jack crawled close to him and Tim put his legs on Jack's shoulders.

"Sir, may I lick your ass now?" - "Yes you may."

Jack never thought of licking another man's ass, so this was very weird to him. He started at ass cheeks slowly making his way to Tim's asshole. He wanted to make sure he does a good job so he was moving his tongue slowly until he reached the anus. The taste was weird but better than he expected. Thankfully it seems Tim took a shower before he came. He kept on licking around the hole and then tried to get his tongue inside. As he kept on licking Tim's phone rang:

"Hey honey, how are you?" answered Tim.

"Yes, I am still at work, going to be working late. Don't wait for me." He was very casual talking to his wife while Jack was busy licking his ass. As he hanged up he said "Enough slut. You do need practice, but you seem to be eager enough. Time for a treat." Jack stopped and pulled back as he heard that.

"Go ahead, show me what cocksucker you are."

Hearing that Jack moved in closer to Tim's dick and started by slowly kissing its head. He loved the taste. He took it whole in his mouth and realized he has no idea what to do. He started sucking on it like a lolipop, but it was quite big. As he was sucking his first cock, Tim leaned back enjoy the sensation. "Take it slow, slut, enjoy it." And Jack did. He licked the shaft of the cock going back and forth. Couple times he tried to get more of it in his mouth, but it seemed impossible.

"Sir may I lick your balls, too?" - "Yeah."

Jack started working on Tim's balls and licked under the shaft. He was enjoying it.

it tasted different than he thought, but good. He licked precum off the top of the dick a few times and he looked at Tim as he did it. "Your cock tastes great, thank you for letting me suck it."

"You have much to learn, but for first time you are doing ok. Keep sucking slut, less talking." Jack continued to work on Tim's cock and he started feeling Tim getting tense. Jack wanted to taste Tim's cum badly now.

"I am going to cum soon and you better not swallow any of it before I give you permission. Keep it in."

Jack was getting more enthusiastic and used his hands to go up and down the shaft as he was sucking the head of the cock. Tim was getting more and more tense untill at some point he started cumming and caught Jack off guard. As the first spirt of cum hit Jack's throat he almost chocked and pulled back. Tim kept cumming over Jack's face and Jack pressed his mouth closer to the cock to catch some of the cum.

"Not bad for the first try, show me the cum in your mouth, slut." Jack opened his mouth showing TIm some cum on his tongue, he felt more of it on his face. "Swallow now" and Jack swallowed his first cum. Tim smiled at him: "You look like someone just came on your face. What do good sluts say?"

"Thank you, Sir, your cum tastes delicious. May I clean your cock?"

"Good slut, go ahead."

With that Jack went back to gently licking Tim's semi-erect cock and getting the last drops of cum off it. He paid attention to the balls as well to make sure no cum was on them. As he was doing it he realized that his cock been leaking cum itself for last few minutes and he desperately wanted to cum himself. He wanted it badly.

"Sir, may I cum, please?" Jack pleaded.

"No slut, you will only cum with my dick in your ass. But don't worry I will be hard soon enough. So how did you like your first blow job experience? Oh I mean sucking cock experience?"

"It was very intense," replied Jack, "I loved it. Thank you, Sir, for letting me suck your dick."

"You are welcome, I love when my sluts are grateful. How is that butt plug?"

"It feels great, Sir, I can wait for your cock to replace it. May I lick your ass more while you recharge?" Jack couldn't believe what he was saying. Tim laughed after he heard that.

"Are you begging to lick my ass? You really are a slut."

"Yes, Sir, I just want to thank you for making me a cocksucker."

"Ok grab a drink and get to work," replied Tim. Jack took another sip of whiskey and crawled closer to Tim. As he raised his legs again on Jack's shoulder, Jack began slowly licking around Tim's anus. This time he was taking his time by slowly circling around the asshole trying to tease it with his tongue. Jack wanted to please, he wanted that cock hard again so he can feel it up his ass. He could tell Tim was enjoying it and he kept on going for another 3 minutes or so trying to do his best. After awhile Tim said "I like you, you are learning quick. Now let's talk about that lube I brought. I assume you don't want me to fuck you dry, right?"

"No, Sir, I would like some lube on my ass" answered Jack meekly. He was so horny at the moment that he'd even try it without lube, but Tim's cock was too big for the first time.

"To earn it, you need to help me make a small video. Don't worry you can wear a mask. But I want to record you applying the lube and fucking yourself with that buttplug in your ass for my collection."

The thought of being recorded scared Jack, but between alcohol and being horny, he was close to agreeing to anything just to get off and cum with a dick in his ass. He agreed. Next, Tim took out lube out of his bag and a black mask.

"Put this on fag and make sure you do a good job, I want a nice video. Oh, almost forgot, I want you to narrate for me in real words, if you know what I mean" said Tim smiling. Jack being called a fag for the first time didn't catch his attention.

"Yes, Sir" replied Jack as he was putting a mask. Tim then turned the phone camera on and started recording: "You may start, slut."

Next, Jack turned his ass towards Tim and took out his butt plug. He put some lube on it and put some on his asshole as well. "What are you doing slut?" Tim sounded unhappy.

"I am sorry, Sir, I am a slut and I am lubing my virgin ass so you can fuck it hard. I shaved it just for you so you can put your big dick in it, just like I am doing it with this but plug." Jack kept getting the plug in and out. It started to become easier and Jack was really enjoying it. He kept on going sliding it and out. As he was doing it he kept thinking of the moment that Tim is going to fuck him soon. He looked back to see Tim slowly stroking his semi-erect cock. He wanted it badly.

"My ass is well lubed now, Sir, would you please fuck it?"

"Not yet slut. Tell the camera what you did today"

"I sucked my first cock, it was great. You came in my throat and I loved the taste of your cum."

"And?" asked Tim.

"I also licked your ass, thank you for letting me. I was honored to put my tongue in your asshole."