Day 1 (Meeting her for the first time)
Tim exited the plane, excited he was finally going to meet Sass, his Queen. Walking through the terminal he didn't know what the next week had in store for him. He chuckled thinking back to just a few hours ago, The TSA agent going through his bag finding all his plugs and toys, ordered by his Queen to bring them, she knew that they would see them. But, Tim didn't care. He walked through the airport with a plug firmly in his boyhole.
He had spent the last 10 hours setting with it in. Layovers and delays. But it was worth it when he walked out and saw her.
His Queen was waiting for him by the baggage claim. He greedily took her in. He wanted to stand there as long as it took to burn everything about her into his mind. Wearing a tank top and the pink skirt he had gotten her. She was a beautiful site to see.
She had other plans though. She ran up to him and screamed.
"Daddy!"
She planted a kiss on him that buckled his knees, He was not expecting this. Instead of his Queen showing up, he got his Princess.
"Princess?" Tim asked, confused.
"Yes!" replied Sass. She had decided to make his welcome a calming time, knowing what was in store for him over the next week. She had not told him everything that was going to happen, except that the first night they both were going to get ass fucked. What she had in mind though was going to change Tim's life forever.
They left the airport arm in arm. Having small talk about his flight and her day so far.
She had a cab waiting. As soon as they got in it though, her personality changed.
"Boy, do you have your plug in?" The cabbie's eyes went wide when she heard this. She and her fare talked a little but on the ride over, like her she seemed to be into some kink, but never thought she would hear this.
"Yes, my Queen, per your orders." Tim said, embarrassed in front of the female cabbie. He didn't know why he felt embarrassed. His Queen noticed this and smirked.
"Boy, are you being shy around the nice cabbie?"
"No, my Queen. I just wasn't expecting it that is all."
"Well you are going to have to get used to the unexpected this week boy. I have plans for you every day."
"Yes my Queen." Tim replied, knowing he was in for something special. He trusted his Queen fully. He knew he was under her protection while he was here.
The ride back to her apartment didn't take long. All the while Tim sat quietly as his Queen chatted with the cabbie.
"Yes, boy here is going to have a lot of new experiences over the next 7 days."
"Talking before I thought you had some dom in you girl." Said the cabbie.
"You a dom also," Looking at the name badge hanging on the mirror "Mary?"
"Yea, But I haven't pegged a boy in a while though." Mary said sadly
"Well maybe we can change that. I have a special night planned for the boy here." And I do need another lady. One of my friends got sick and had to back out."
Outside her apartment, Sass got Mary's number and her online info so she could check her out.
"The ride is on me, just make sure you text me." Mary said excitedly
Walking up to her apartment Sass had Tim walk ahead of her on the stairs. After a floor or so she flipped the bottom of the plug that was in Tim's hole. And asked
"Boy, would you like for Mary to join your surprise later this week?"
"If my Queen wants her there, I would not be upset."
"Did you think she was cute, boy?"
She was, my Queen."
"Yes she was, I might even see if she wants to play just the two of us. Maybe I will let you watch."
"Thank you my Queen."
Outside of her apartment, His Queen laid out the rules.
"When we are in this apartment you must be naked at all times. No matter if I am being your Queen, your Princess or just Sass. You will have a plug in at all times. Except for the bathroom and when we play. Do you understand boy?"
"Yes, My Queen."
"Good boy."
"Now go put your stuff in my room and take a shower." I want to cook for our first night together. Oh you did clean yourself out with an enema right boy?"
"Yes, my Queen. Twice, as ordered."
"Good boy," She said.
Tim loved it when she called him good boy. Stepping into the shower felt amazing to Tim. The hot water washes the day away. He wasn't jetlagged thankfully because there was no time zone difference. It had just been a long day. Either it was screaming kids in the airport, drunk assholes sitting in the seats in front of him or the fact that he had not cum in three days. (Orders from his Queen) The shower refreshed him though and woke him up. Thinking about what his Queen had in store for him this week he didn't hear the knock at first.
"Boy, you better not be touching yourself in there!" His Queen said firmly.
"No my Queen. Just enjoying the warmth." Quickly he washed away the soap and shampoo. Knowing he must not keep her waiting , he dried off and threw the towel over the rail to dry. Remembering the rules he stepped out into the room naked and realized he wasn't alone in being that way.
Standing about 10 feet away going through her drawers was his Queen. Naked and amazingly breathtaking. She was bent at the waist. And while he knew she didn't like her ass but he thought it was perfect. It took everything in him not to walk over, sink to his knees and start licking her. Just seeing her got him hard as a rock.
Realizing he was there she turned around and smiled.
"Look at you boy." she said with a laugh "You are hard and not able to do anything about it. Don't you dare touch it. Let it go down and eat supper."
Sitting at the table naked, enjoying a nice dinner of baked chicken and sides, Sass and Tim chatted about life and just enjoyed each other's company. Once they were done Sass decided to get the night started and asked Tim a simple question.
"Would you rather have Princess or Queen tonight?"
Tim thought for a moment and replied "Queen."
Sass laughed and said "Thought that would be your answer, such a good boy. Now clear the dishes and then come back into the living room when you are done."
5 minutes later Tim walks into the living room to see his Queen sitting on the couch wearing a harness with a 8 inch strapon sticking out proudly. She pats the seat next to her and Tim walks over and sits down. She can see the excitement on his face and if she is being honest with herself, she was excited also.
She has spent the last 6 months helping him, coaching him, and teaching him to stretch his boyhole for this night. She took his hand and placed it around her cock. It was so thick his hand couldn't even fit around it. She looked at him and asked
"Boy, are you ready to have this in you? I want you to use your mouth on it. Get it nice and wet and if you do a good job with that, I will allow you to be my little buttboy tonight."
"Yes my Queen." Tim got infront of her and took the dildo in his mouth. He then did something he has never done before and gagged on a cock. Looking down at her boy, Sass smiled and took her hand and placed it on the back of his head, she pushed it down and held it there causing tears to come to his eyes.
She allowed him to back off and catch his breath,
"Get on the couch. Head hanging off the front, boy."
She straddled his head and slapped him across the face with her cock. When TIm opened his mouth in surprise she shoved her cock in his mouth and pushed. She pushed past the resistance in his throat and kept going. In no time she had all 8 inches down his throat and was face fucking him.
Knowing he had to be good, Tim relaxed and began to enjoy the feeling. Without realizing it he became hard again. His Queen saw this and grabbed it and squeezed it.
"Boy, what do you think you are doing getting hard? You are such a bitchboy that you get hard getting face fucked?"
She pulled her cock out of his throat and told him to sit. She was upset with him. She decided he needed to be taught a lesson. She opened a box on the table next to the couch and pulled out something small.
"Boy I was saving this for later this week but you have forced me to use it now." She showed him a cock cage. "We will stop until you get soft boy, then you will be locked into this and won't come out of it again unless you do well."
A few minutes later he had his cock in the cage and the key was placed in a safe in the wall. His Queen pointed at the couch and he knew she wanted him on his knees, his ass in the air. She stepped away for a minute and when she came back she had a smaller copy of her strapon. Same length but not as thick. Along with a bottle of lube. She put on a pair of rubber gloves and pulled the plug out of his ass with one pull. She applied lube to his boyhole and worked her fingers in , first one for a few times then two getting all the way up to 4 fingers before switching to the smaller dildo.
Tim knew he had upset his Queen. He was worried that the night would end before it even really began. He just couldn't help it. He enjoyed the power she had over him. She had him do so many things before today that he knew he would do almost anything to please her. He needed her to fuck him in the ass. No, he didn't just need it, he wanted it more than anything. So when she told him to wear the cage he hoped it wouldn't end there. He did as he was ordered and got on his knees on the couch. She left him for a minute and when she came back he saw the smaller dildo and lube. He didn't react at all but was happy she still wanted to do this.
When she pulled his plug out it made a popping sound. He had never pulled one out that forceful before. It didn't hurt but he could feel himself still open. When he felt her hand circle his hole, he knew that she was going to finger him first. He was excited. His cock pushing against the cage, keeping him from getting hard. When she pushed the first finger in and moved it around he hoped she would try for more. One finger just couldn't fill him.
She then quickly put two, three then four fingers in him. All the way past her knuckles. Her thumb sticking upward toward his back.
After a few seconds she pulled out and he felt empty. But, it didn't last long. His Queen lubed up the smaller dildo and shoved it balls deep into him. He yelped and moaned at the same time.
"Boy , did you just moan?" his Queen asked "I thought you might yell a little but I wasn't expecting the moan. You really are a buttboy aren't you."
"Yes my Queen." Tim said through gritted teeth. He had never been this full. His Queen's toy was in places no other toy had been before. He came close to cumming with just it being forced into him.
"I need a break and a glass of water. I want you to turn around and sit on that plug until I come back."
Walking out of the kitchen his Queen asked "How does that feel boy?"
"Love it my Queen." Tim answered truthfully.
"Good boy." His Queen said with a smile. "Now, just sit there and relax, I have to check my work email."
Tim sat there for what felt like 30 minutes, his ass adjusting to the dildo in him. When she came back in, his Queen had her gloves back on and was lubing the strapon she had on. She threw a small pillow on the rug
"Boy, I believe it is time for me to wreck your ass, get on your knees on the rug. Face down on the pillow and hands spreading your cheeks."
Tim did as he was ordered. He would always do as his Queen ordered.
She walked up behind him and started pulling and pushing the dildo out of his ass. Moving it up and down, left and right, loosening up his hole for what was next.
She bent down and asked "Boy are you ready for me to fuck you?"
"Yes please! My Queen." Tim said needly
She pulled the cock out of his ass and didn't even give him a chance to take a breath. Shoved her strapon into him. Balls deep and then held it there. Tim didn't know if he could take it. His ass was being stretched to the limit. He almost pulled away, but knew that would upset his Queen. All he could do was bite down on the pillow and wait until he adjusted to the feeling.
She looked down at her boy and saw that he was struggling to take her strapon. She thought of backing off, but decided to make him earn his fucking. He did say please after all.
She started pulling out her cock, all the way to the tip and then pushed it back in quickly. She grabbed his hips and started thrusting into him hard and rough. Tim was grunting with each bottom out and was moaning everytime she thrusted into him. She was enjoying the power she had over him. She was planning to make this last all night. She knew he was game. As long as his ass could take the beating that is.
She continued to work her cock into him, his ass loosening up with every second that passed. Tim had got passed the pain stage and had moved to the pleasure stage of the ass fucking. He started moaning more and more with each forward movement his Queen made. This went on for about 20 minutes. Only near the end did his Queen speak to him.
"Beginning to love it boy? His Queen asked him.
"Yes, my Queen."
"Good boy, I plan on using this hole all night. But, I do have an idea." she said. "Sit open and turn around."
She started to pull her cock out of his ass, but before she did she grabbed her phone, and when she took it out completely she took a picture of his gaping hole. She showed him the picture of his ass. It was opened like never before. All the while she had her cock next to his face.
"Boy, be glad I had you clean yourself out before. Because you are about to have your first ATM."
Tim did as he was ordered. He opened his mouth and started sucking his Queens cock. He could taste the lube and his ass juice on it. He could feel how loose his ass was. He knew his Queen was going to use it more. And that made him happy. But right now it was what made his Queen happy that mattered. She pushed her cock down his throat. He had gotten used to this earlier. Before he knew it she had him deep throating her balls deep.
Chuckling she said "That skill will come in handy later in the week."
After a couple minutes of face fucking she backed up and sat on the couch.
"Crawl over here boy, stand up and turn around. I want to see you ride this cock from behind."
TIm crawled to her, his ass sore, but he wanted more. Standing and turning around, his Queen applied a fresh coating of lube to her cock. He lowered himself down onto her cock and slowly let it penetrate him. About halfway down she pushed up quickly and slammed into his ass. When she came down she pulled him with her and held him there.
"I said ride, boy. Rough and hard if you don't do it to my liking I will do it for you.".
He started slamming himself down onto her cock. The angle that he was doing it at caused the cock to bend forward and push upward into him, making it feel like his guts were being rearranged.
All the while his Queen talked dirty to him. After about 5 minutes of this she could tell that his knees were getting weak.
"That's enough boy, your knees look like they are about to give out. Sit on the couch."
Tim lifted himself off the cock and could feel that his asshole was gaped. He got on the couch. She went behind the couch and threw over a couple straps he didn't see before.
"Raise your legs boy." she said. She wrapped the loops at the end of the straps to his ankles and pulled them back and out. She then attached his wrists to another loop at the end of the strap. He was completely at her mercy. She walked over to her safe and got the key for his cage.
Unlocking the cage she said "You have been a good boy, so you may cum. And for a special treat I am going to help."
What she next surprised him. She leaned over and took him in her mouth. She started sucking on him and in no time he was the biggest he had ever been. When she was happy with him, she sat up and drove into him with her cock. She preceded to fuck him harder then anytime tonight. While fucking him she lubed her hand up and started jacking him off. She plowed into him with reckless abandonment. Savoring the look on his face. Within 5 minutes she could see he was about to cum. She kept jerking him off but aimed his cock at his face. He exploded and shot ropes of cum at his own face. It got all over him, landing on his chin and in his mouth, it got into his hair and when it finally slacked off it landed on his chest.
After he was spent his Queen continued to jack him off. Milking the last bit of cum out of him. All the while she keep fucking him hard. She wasn't done with him yet. After another 10 minutes of hard fucking, she pulled out of him and left his ass gaped open. She looked at it and smiled, she decided to try something that Tim brought up a few weeks ago.
Unlocking the straps, She said, "Get on your knees again boy." she then applied some more lube to her hand and started sliding it into him.
Tim had just cummed more than ever before. He had also just enjoyed the best sexual experience of his life. Giving himself to his Queen had been the best decision he had ever made. Allowing her to own his ass and use it how she saw fit. It had been 6 months since he found her on snapchat, Soon after that he told her about he fantasy of having a woman using a strapon on him and fucking his ass. Within days she became his Queen and started having him use plugs on his ass and coaching him to be able to stretch his ass. Days before he came up to meet her, he finally got his biggest plug in. It made his Queen very proud. It also made him very proud.
The feeling of his Queen's hand sliding into him brought him back. He had brought up fisting with her once and didn't think it was something she was into, (she had a bad experience with it) but he must have been wrong,
"Boy, I am about to give you a treat." She said. "You know I normally wouldn't do this, but your boyhole being open like that is just too inviting."
His ass didn't resist her hand at all. With the lube and the fact that it was well fucked, she slid into it in one quick fluid move. She moved it around a bit and made a fist. Then she opened it back up and started moving her fingers in a come here movement. Tim looked like he was in heaven . She couldn't blame him for enjoying it. She wasn't going to get upset with him. He had earned it tonight.
When he felt her hand slip into him easily, he knew his ass would never be the same after this week. He could feel her moving her hand around and when she closed it into a fist and then opened it and started moving her fingers, it was a sensation he wasn't expecting. She was stimulating his prostate. He couldn't help but smile. He also almost came real close to cumming again. But, he didn't want to give his Queen a reason to stop. But, what she said next told him that he made the right choice to have her be his Queen.
"Boy, I believe you have earned a little reward. I am going to make you cum just by milking your prostate."
She kept working on him and within a few minutes he was spewing cum again. Once he came down she closed her fist and again and started pushing and pulling out of his ass hard and quick. She continued doing this for about 5 minutes until she knew he couldn't take it anymore. She then pulled her fist completely out and then aggressively punch fucked him 3 or 4 times before pulling out roughly.
"You didn't think there wouldn't be a little punishment for that enjoyment did you boy? I wouldn't be a good Queen if I just gave you rewards, now would I?"
"No my Queen. You are the best Queen."
"Now stay where you are, I'll be right back."
When she came back, she had a plug that was shorter but wider then even her biggest dildo. She pushed it into him and felt just a slight pause when the ridge went in. She then handed him a pair of panties. He put them on knowing they would keep the plug in better. She then walked over to the dining room table and sat down.
"Boy, that is to stay in the rest of the night. It will get you ready for what's coming the rest of the week. Now crawl over here and kiss my feet. I believe I have earned your worshipping tonight."
Tim got off the couch and crawled over to her, his ass up in the air and his face inches from the ground. When he got to his Queens feet, he took them in his hand and kissed them with passion. This was something he had wanted to do for months. He would have done it the moment he saw her at the airport if she had ordered him to, right in front of everyone, with no shame. He took his time and kissed every inch of them.
She allowed this to go on for about 10 minutes before pulling her feet away.. She reached down and softly lifted his chin and pulled him up to her. She then passionately kissed him.
"You have been such a good boy tonight. But, you are still a buttboy and will be treated as such."
She pulled a collar and leash off the table and attached it around his neck. She then got up and pulled. He crawled behind her to a walk-in closet, She had a cage in there ready for him, she opened the door and led him in by his leash. There was a large dog bed in the cage and nothing else. She took off the leash and hung it on a hook beside the cage. She closed the door to the cage.
"Good night boy. Sleep well."
"Good night, my Queen."
She turned off the light and shut the closet door. Tim laid there and recalled his day and knowing that his week was going to be amazing. He was so tired that he drifted off to sleep in no time at all.
In what seemed like no time at all, the closet door busted open and the light was turned on.
"Wake up buttboy, ready for day 2 of your training." His Queen yelled, startling him awake.
To be continued...
Tim exited the plane, excited he was finally going to meet Sass, his Queen. Walking through the terminal he didn't know what the next week had in store for him. He chuckled thinking back to just a few hours ago, The TSA agent going through his bag finding all his plugs and toys, ordered by his Queen to bring them, she knew that they would see them. But, Tim didn't care. He walked through the airport with a plug firmly in his boyhole.
He had spent the last 10 hours setting with it in. Layovers and delays. But it was worth it when he walked out and saw her.
His Queen was waiting for him by the baggage claim. He greedily took her in. He wanted to stand there as long as it took to burn everything about her into his mind. Wearing a tank top and the pink skirt he had gotten her. She was a beautiful site to see.
She had other plans though. She ran up to him and screamed.
"Daddy!"
She planted a kiss on him that buckled his knees, He was not expecting this. Instead of his Queen showing up, he got his Princess.
"Princess?" Tim asked, confused.
"Yes!" replied Sass. She had decided to make his welcome a calming time, knowing what was in store for him over the next week. She had not told him everything that was going to happen, except that the first night they both were going to get ass fucked. What she had in mind though was going to change Tim's life forever.
They left the airport arm in arm. Having small talk about his flight and her day so far.
She had a cab waiting. As soon as they got in it though, her personality changed.
"Boy, do you have your plug in?" The cabbie's eyes went wide when she heard this. She and her fare talked a little but on the ride over, like her she seemed to be into some kink, but never thought she would hear this.
"Yes, my Queen, per your orders." Tim said, embarrassed in front of the female cabbie. He didn't know why he felt embarrassed. His Queen noticed this and smirked.
"Boy, are you being shy around the nice cabbie?"
"No, my Queen. I just wasn't expecting it that is all."
"Well you are going to have to get used to the unexpected this week boy. I have plans for you every day."
"Yes my Queen." Tim replied, knowing he was in for something special. He trusted his Queen fully. He knew he was under her protection while he was here.
The ride back to her apartment didn't take long. All the while Tim sat quietly as his Queen chatted with the cabbie.
"Yes, boy here is going to have a lot of new experiences over the next 7 days."
"Talking before I thought you had some dom in you girl." Said the cabbie.
"You a dom also," Looking at the name badge hanging on the mirror "Mary?"
"Yea, But I haven't pegged a boy in a while though." Mary said sadly
"Well maybe we can change that. I have a special night planned for the boy here." And I do need another lady. One of my friends got sick and had to back out."
Outside her apartment, Sass got Mary's number and her online info so she could check her out.
"The ride is on me, just make sure you text me." Mary said excitedly
Walking up to her apartment Sass had Tim walk ahead of her on the stairs. After a floor or so she flipped the bottom of the plug that was in Tim's hole. And asked
"Boy, would you like for Mary to join your surprise later this week?"
"If my Queen wants her there, I would not be upset."
"Did you think she was cute, boy?"
She was, my Queen."
"Yes she was, I might even see if she wants to play just the two of us. Maybe I will let you watch."
"Thank you my Queen."
Outside of her apartment, His Queen laid out the rules.
"When we are in this apartment you must be naked at all times. No matter if I am being your Queen, your Princess or just Sass. You will have a plug in at all times. Except for the bathroom and when we play. Do you understand boy?"
"Yes, My Queen."
"Good boy."
"Now go put your stuff in my room and take a shower." I want to cook for our first night together. Oh you did clean yourself out with an enema right boy?"
"Yes, my Queen. Twice, as ordered."
"Good boy," She said.
Tim loved it when she called him good boy. Stepping into the shower felt amazing to Tim. The hot water washes the day away. He wasn't jetlagged thankfully because there was no time zone difference. It had just been a long day. Either it was screaming kids in the airport, drunk assholes sitting in the seats in front of him or the fact that he had not cum in three days. (Orders from his Queen) The shower refreshed him though and woke him up. Thinking about what his Queen had in store for him this week he didn't hear the knock at first.
"Boy, you better not be touching yourself in there!" His Queen said firmly.
"No my Queen. Just enjoying the warmth." Quickly he washed away the soap and shampoo. Knowing he must not keep her waiting , he dried off and threw the towel over the rail to dry. Remembering the rules he stepped out into the room naked and realized he wasn't alone in being that way.
Standing about 10 feet away going through her drawers was his Queen. Naked and amazingly breathtaking. She was bent at the waist. And while he knew she didn't like her ass but he thought it was perfect. It took everything in him not to walk over, sink to his knees and start licking her. Just seeing her got him hard as a rock.
Realizing he was there she turned around and smiled.
"Look at you boy." she said with a laugh "You are hard and not able to do anything about it. Don't you dare touch it. Let it go down and eat supper."
Sitting at the table naked, enjoying a nice dinner of baked chicken and sides, Sass and Tim chatted about life and just enjoyed each other's company. Once they were done Sass decided to get the night started and asked Tim a simple question.
"Would you rather have Princess or Queen tonight?"
Tim thought for a moment and replied "Queen."
Sass laughed and said "Thought that would be your answer, such a good boy. Now clear the dishes and then come back into the living room when you are done."
5 minutes later Tim walks into the living room to see his Queen sitting on the couch wearing a harness with a 8 inch strapon sticking out proudly. She pats the seat next to her and Tim walks over and sits down. She can see the excitement on his face and if she is being honest with herself, she was excited also.
She has spent the last 6 months helping him, coaching him, and teaching him to stretch his boyhole for this night. She took his hand and placed it around her cock. It was so thick his hand couldn't even fit around it. She looked at him and asked
"Boy, are you ready to have this in you? I want you to use your mouth on it. Get it nice and wet and if you do a good job with that, I will allow you to be my little buttboy tonight."
"Yes my Queen." Tim got infront of her and took the dildo in his mouth. He then did something he has never done before and gagged on a cock. Looking down at her boy, Sass smiled and took her hand and placed it on the back of his head, she pushed it down and held it there causing tears to come to his eyes.
She allowed him to back off and catch his breath,
"Get on the couch. Head hanging off the front, boy."
She straddled his head and slapped him across the face with her cock. When TIm opened his mouth in surprise she shoved her cock in his mouth and pushed. She pushed past the resistance in his throat and kept going. In no time she had all 8 inches down his throat and was face fucking him.
Knowing he had to be good, Tim relaxed and began to enjoy the feeling. Without realizing it he became hard again. His Queen saw this and grabbed it and squeezed it.
"Boy, what do you think you are doing getting hard? You are such a bitchboy that you get hard getting face fucked?"
She pulled her cock out of his throat and told him to sit. She was upset with him. She decided he needed to be taught a lesson. She opened a box on the table next to the couch and pulled out something small.
"Boy I was saving this for later this week but you have forced me to use it now." She showed him a cock cage. "We will stop until you get soft boy, then you will be locked into this and won't come out of it again unless you do well."
A few minutes later he had his cock in the cage and the key was placed in a safe in the wall. His Queen pointed at the couch and he knew she wanted him on his knees, his ass in the air. She stepped away for a minute and when she came back she had a smaller copy of her strapon. Same length but not as thick. Along with a bottle of lube. She put on a pair of rubber gloves and pulled the plug out of his ass with one pull. She applied lube to his boyhole and worked her fingers in , first one for a few times then two getting all the way up to 4 fingers before switching to the smaller dildo.
Tim knew he had upset his Queen. He was worried that the night would end before it even really began. He just couldn't help it. He enjoyed the power she had over him. She had him do so many things before today that he knew he would do almost anything to please her. He needed her to fuck him in the ass. No, he didn't just need it, he wanted it more than anything. So when she told him to wear the cage he hoped it wouldn't end there. He did as he was ordered and got on his knees on the couch. She left him for a minute and when she came back he saw the smaller dildo and lube. He didn't react at all but was happy she still wanted to do this.
When she pulled his plug out it made a popping sound. He had never pulled one out that forceful before. It didn't hurt but he could feel himself still open. When he felt her hand circle his hole, he knew that she was going to finger him first. He was excited. His cock pushing against the cage, keeping him from getting hard. When she pushed the first finger in and moved it around he hoped she would try for more. One finger just couldn't fill him.
She then quickly put two, three then four fingers in him. All the way past her knuckles. Her thumb sticking upward toward his back.
After a few seconds she pulled out and he felt empty. But, it didn't last long. His Queen lubed up the smaller dildo and shoved it balls deep into him. He yelped and moaned at the same time.
"Boy , did you just moan?" his Queen asked "I thought you might yell a little but I wasn't expecting the moan. You really are a buttboy aren't you."
"Yes my Queen." Tim said through gritted teeth. He had never been this full. His Queen's toy was in places no other toy had been before. He came close to cumming with just it being forced into him.
"I need a break and a glass of water. I want you to turn around and sit on that plug until I come back."
Walking out of the kitchen his Queen asked "How does that feel boy?"
"Love it my Queen." Tim answered truthfully.
"Good boy." His Queen said with a smile. "Now, just sit there and relax, I have to check my work email."
Tim sat there for what felt like 30 minutes, his ass adjusting to the dildo in him. When she came back in, his Queen had her gloves back on and was lubing the strapon she had on. She threw a small pillow on the rug
"Boy, I believe it is time for me to wreck your ass, get on your knees on the rug. Face down on the pillow and hands spreading your cheeks."
Tim did as he was ordered. He would always do as his Queen ordered.
She walked up behind him and started pulling and pushing the dildo out of his ass. Moving it up and down, left and right, loosening up his hole for what was next.
She bent down and asked "Boy are you ready for me to fuck you?"
"Yes please! My Queen." Tim said needly
She pulled the cock out of his ass and didn't even give him a chance to take a breath. Shoved her strapon into him. Balls deep and then held it there. Tim didn't know if he could take it. His ass was being stretched to the limit. He almost pulled away, but knew that would upset his Queen. All he could do was bite down on the pillow and wait until he adjusted to the feeling.
She looked down at her boy and saw that he was struggling to take her strapon. She thought of backing off, but decided to make him earn his fucking. He did say please after all.
She started pulling out her cock, all the way to the tip and then pushed it back in quickly. She grabbed his hips and started thrusting into him hard and rough. Tim was grunting with each bottom out and was moaning everytime she thrusted into him. She was enjoying the power she had over him. She was planning to make this last all night. She knew he was game. As long as his ass could take the beating that is.
She continued to work her cock into him, his ass loosening up with every second that passed. Tim had got passed the pain stage and had moved to the pleasure stage of the ass fucking. He started moaning more and more with each forward movement his Queen made. This went on for about 20 minutes. Only near the end did his Queen speak to him.
"Beginning to love it boy? His Queen asked him.
"Yes, my Queen."
"Good boy, I plan on using this hole all night. But, I do have an idea." she said. "Sit open and turn around."
She started to pull her cock out of his ass, but before she did she grabbed her phone, and when she took it out completely she took a picture of his gaping hole. She showed him the picture of his ass. It was opened like never before. All the while she had her cock next to his face.
"Boy, be glad I had you clean yourself out before. Because you are about to have your first ATM."
Tim did as he was ordered. He opened his mouth and started sucking his Queens cock. He could taste the lube and his ass juice on it. He could feel how loose his ass was. He knew his Queen was going to use it more. And that made him happy. But right now it was what made his Queen happy that mattered. She pushed her cock down his throat. He had gotten used to this earlier. Before he knew it she had him deep throating her balls deep.
Chuckling she said "That skill will come in handy later in the week."
After a couple minutes of face fucking she backed up and sat on the couch.
"Crawl over here boy, stand up and turn around. I want to see you ride this cock from behind."
TIm crawled to her, his ass sore, but he wanted more. Standing and turning around, his Queen applied a fresh coating of lube to her cock. He lowered himself down onto her cock and slowly let it penetrate him. About halfway down she pushed up quickly and slammed into his ass. When she came down she pulled him with her and held him there.
"I said ride, boy. Rough and hard if you don't do it to my liking I will do it for you.".
He started slamming himself down onto her cock. The angle that he was doing it at caused the cock to bend forward and push upward into him, making it feel like his guts were being rearranged.
All the while his Queen talked dirty to him. After about 5 minutes of this she could tell that his knees were getting weak.
"That's enough boy, your knees look like they are about to give out. Sit on the couch."
Tim lifted himself off the cock and could feel that his asshole was gaped. He got on the couch. She went behind the couch and threw over a couple straps he didn't see before.
"Raise your legs boy." she said. She wrapped the loops at the end of the straps to his ankles and pulled them back and out. She then attached his wrists to another loop at the end of the strap. He was completely at her mercy. She walked over to her safe and got the key for his cage.
Unlocking the cage she said "You have been a good boy, so you may cum. And for a special treat I am going to help."
What she next surprised him. She leaned over and took him in her mouth. She started sucking on him and in no time he was the biggest he had ever been. When she was happy with him, she sat up and drove into him with her cock. She preceded to fuck him harder then anytime tonight. While fucking him she lubed her hand up and started jacking him off. She plowed into him with reckless abandonment. Savoring the look on his face. Within 5 minutes she could see he was about to cum. She kept jerking him off but aimed his cock at his face. He exploded and shot ropes of cum at his own face. It got all over him, landing on his chin and in his mouth, it got into his hair and when it finally slacked off it landed on his chest.
After he was spent his Queen continued to jack him off. Milking the last bit of cum out of him. All the while she keep fucking him hard. She wasn't done with him yet. After another 10 minutes of hard fucking, she pulled out of him and left his ass gaped open. She looked at it and smiled, she decided to try something that Tim brought up a few weeks ago.
Unlocking the straps, She said, "Get on your knees again boy." she then applied some more lube to her hand and started sliding it into him.
Tim had just cummed more than ever before. He had also just enjoyed the best sexual experience of his life. Giving himself to his Queen had been the best decision he had ever made. Allowing her to own his ass and use it how she saw fit. It had been 6 months since he found her on snapchat, Soon after that he told her about he fantasy of having a woman using a strapon on him and fucking his ass. Within days she became his Queen and started having him use plugs on his ass and coaching him to be able to stretch his ass. Days before he came up to meet her, he finally got his biggest plug in. It made his Queen very proud. It also made him very proud.
The feeling of his Queen's hand sliding into him brought him back. He had brought up fisting with her once and didn't think it was something she was into, (she had a bad experience with it) but he must have been wrong,
"Boy, I am about to give you a treat." She said. "You know I normally wouldn't do this, but your boyhole being open like that is just too inviting."
His ass didn't resist her hand at all. With the lube and the fact that it was well fucked, she slid into it in one quick fluid move. She moved it around a bit and made a fist. Then she opened it back up and started moving her fingers in a come here movement. Tim looked like he was in heaven . She couldn't blame him for enjoying it. She wasn't going to get upset with him. He had earned it tonight.
When he felt her hand slip into him easily, he knew his ass would never be the same after this week. He could feel her moving her hand around and when she closed it into a fist and then opened it and started moving her fingers, it was a sensation he wasn't expecting. She was stimulating his prostate. He couldn't help but smile. He also almost came real close to cumming again. But, he didn't want to give his Queen a reason to stop. But, what she said next told him that he made the right choice to have her be his Queen.
"Boy, I believe you have earned a little reward. I am going to make you cum just by milking your prostate."
She kept working on him and within a few minutes he was spewing cum again. Once he came down she closed her fist and again and started pushing and pulling out of his ass hard and quick. She continued doing this for about 5 minutes until she knew he couldn't take it anymore. She then pulled her fist completely out and then aggressively punch fucked him 3 or 4 times before pulling out roughly.
"You didn't think there wouldn't be a little punishment for that enjoyment did you boy? I wouldn't be a good Queen if I just gave you rewards, now would I?"
"No my Queen. You are the best Queen."
"Now stay where you are, I'll be right back."
When she came back, she had a plug that was shorter but wider then even her biggest dildo. She pushed it into him and felt just a slight pause when the ridge went in. She then handed him a pair of panties. He put them on knowing they would keep the plug in better. She then walked over to the dining room table and sat down.
"Boy, that is to stay in the rest of the night. It will get you ready for what's coming the rest of the week. Now crawl over here and kiss my feet. I believe I have earned your worshipping tonight."
Tim got off the couch and crawled over to her, his ass up in the air and his face inches from the ground. When he got to his Queens feet, he took them in his hand and kissed them with passion. This was something he had wanted to do for months. He would have done it the moment he saw her at the airport if she had ordered him to, right in front of everyone, with no shame. He took his time and kissed every inch of them.
She allowed this to go on for about 10 minutes before pulling her feet away.. She reached down and softly lifted his chin and pulled him up to her. She then passionately kissed him.
"You have been such a good boy tonight. But, you are still a buttboy and will be treated as such."
She pulled a collar and leash off the table and attached it around his neck. She then got up and pulled. He crawled behind her to a walk-in closet, She had a cage in there ready for him, she opened the door and led him in by his leash. There was a large dog bed in the cage and nothing else. She took off the leash and hung it on a hook beside the cage. She closed the door to the cage.
"Good night boy. Sleep well."
"Good night, my Queen."
She turned off the light and shut the closet door. Tim laid there and recalled his day and knowing that his week was going to be amazing. He was so tired that he drifted off to sleep in no time at all.
In what seemed like no time at all, the closet door busted open and the light was turned on.
"Wake up buttboy, ready for day 2 of your training." His Queen yelled, startling him awake.
To be continued...