Olivia Caught Red Handed Finale
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Olivia Caught Red Handed , Part One free porn video
It was in the middle of the afternoon when Olivia decided to play with herself. She knew she would be in big trouble when Jack came home from work, but she wanted to give herself a much-needed orgasm. She had been two months without an orgasm and she was about to bust. So she went to grab her favorite 9inch dildo and her most trusted glass ribbed dildo as well. She laid down on the couch with her legs spread open, and without much fanfare plunged her glass dildo into wet milky pussy. As she was playing with herself, she didn’t realize that Jack was watching from his big leather chair. Watching her in the amidst of her much needed orgasm.
"What do you think you are doing?" he said startling Olivia.
When Olivia looked up, she was surprised that Jack was watching her toy with her pussy. She instantly sat up on her bed.
"I-I was just..." she started to say.
"You were just playing with yourself without my permission, weren't you young lady?" he finished her statement.
"Y-yes Sir," she said, looking down.
"Haven't I told you before that you are not to play with your pussy unless I tell you to? Haven't I said that your orgasms were my gift to you and you are not to cum without my permission?" he said.
"Yes Sir, I'm sorry I just... needed to," she said, apologetically.
"Then you should have come to me and said something. Now go to your room and stand in your corner and think about what you've done while I decide how I am to punish you. Do not come out until I call you. Now move," he commanded.
Olivia slunk down the hall into her room and stood in the corner as he commanded wondering what was to become of her.
Jack, meanwhile went into his office to think of what punishment, he would use on his Olivia. He didn’t want to be too harsh on her first punishment. He sat in his office for a few minutes. Ten minutes later he came out of his office with his punishment for his naughty Olivia. He called her back into the living room and as she came in he told her to come stand in front of him.
"Olivia I have decided what needs to be done. Since this is your first punishment, I will be a little easier on you, but if this happens again, I will give you the full punishment. Do you understand?"
"Yes Sir," she said anxiously.
"Good. Now hike up your skirt and drop your panties and lay over my knees. I am going to spank your bare ass,” he demanded.
Olivia dropped her skirt and panties and she laid over Jack’s knees. He rubbed her ass with some baby oil.
He gave the first swat on one ass cheek and Olivia squealed, "One, Sir." squirming on his lap. He let the burn sink in a bit before he gave her another swat on the other cheek. Olivia squealed again, "Two, Sir. He gave her four more swats alternating ass cheeks. Then he rubbed her ass before giving her the remaining four. Olivia counted each one as she was told.
After her spanking Jack told Olivia, Get on your knees and sit in between my knees. Jack grabbed her chin and locked eyes with her.
“Olivia, you know what you did was wrong don’t you?” he said.
“Yes, Sir. I had orgasm that wasn’t given by you. I broke the rules and I deserved that punishment. I’m sorry for disobeying you.” she said, contritely
“I know you’re sorry little one but I’m still mad at you. I still love you, though, that’s not going to change Olivia. Now get on the bed on all fours,”
Olivia got on the bed on all fours waiting for him. He got on the bed and just shoved his cock deep inside her pussy, owning it and claiming it for his own pleasurable needs. Since Olivia already had her orgasm, Jack fucked her like a fuck doll that she was. He didn’t waste any time to get down to business using her to his advantage. She moaned out from being used for his personal use.
Then he flipped her over as he pinned her arms above her head as he pounded her creamy milky pussy raw and bare. Olivia moaned out in pleasure, screaming out in pure ecstasy and causing her to cum. But not for her pleasure, though, it was for his pleasure and his pleasure only. He came in her as he continued to fuck her like a savage. Teaching her that her orgasm is a very special gift only to be given by him.
“Olivia, darling you came twice you little greedy slut,” he said
“Yes, Sir. I learned my lesson, no more giving myself an orgasm that’s not from you,” she said
“Good girl.”
. . . . .
The next morning at breakfast, Olivia seemed troubled. Jack noticed but didn't say anything, figuring she would when she felt like it. But breakfast was served and ate it without her saying anything. After breakfast was over, Jack went into the living room as was his custom to read the newspaper while Olivia cleared the table and put the dishes in the dishwasher. Then she came into the living room and sat down on the sofa to watch TV.
Still having said nothing all morning, Jack folded his newspaper and set it aside. "Olivia come here," he said. Olivia looked at him then quietly came over and knelt in front of him as she had been taught.
"Olivia, you haven't said two words all morning. Now I know something is bothering you and until now I have kept quiet about it. But no more. Now I want to know what has your mind so troubled," he said.
"It's about what happened yesterday, Sir," she said.
"What happened yesterday?" he asked, not understanding the problem yet.
"Yes, Sir. When you caught me masturbating, and spanked me for it," she said.
"Yes I did. But then after the spanking I said the matter was over. What's the problem?" he asked.
"Well Sir, I was just wondering... why you were so easy on me with my punishment," Olivia said, looking up at him.
"Olivia this was the first time you disobeyed me like that. I couldn't very well spank you like you had done it repeatedly. Had this been a recurring thing, your punishment would have been considerably harder. But for a first offense I felt it was adequate," he said.
"Yes Sir," she said, "Only..."
"What is it, Olivia?"
"Sir may I ask you for another spanking?" she said.
"You want another spanking?" he said.
Yes, Sir. And this time don't be so easy on me," Olivia said.
"Why would you want another spanking?" he asked.
"Sir, I knew that you told me I wasn't to masturbate without your permission. But I did it anyway. I told you I couldn't help it - that I needed to, and it's true, after being denied an orgasm for so long, I was about to bust. But I am a submissive and you are my Master - I should have come to you and explained my needs. There is no excuse for my behavior. And because you went easy on me for it, makes it all the worse. It's almost like you ignored my disobedience or rewarded me for it. I need to be punished for disobeying you, Sir. And I need to feel like I was punished if I am to learn to control myself for you. Do you understand, Sir?" Olivia explained.
"I think I do, Olivia. Very well, you shall have your proper spanking this evening then. I want you to feel that your punishment was appropriate as well," he said.
"Thank you Sir," Olivia said.
But before that happens we have things to do. So go upstairs and get dressed. Wear that white off the shoulder crop top you have and your short black mini-skirt - the one that fits so tight I can tell if you're wearing panties under it! Oh and don't be!" he said. Olivia smiled; usually when he specified what she was to wear, he had a reason for it!
Olivia went to the bedroom and got dressed as he requested. She didn't wear a bra or panties as he had directed and she put on her clothes then went in to apply her makeup and finish getting ready. She didn't know what he had planned but she knew it was going to be sexy and exciting!
She came out of the bathroom to find him already dressed and ready to go. "I'm already Sir, do you like the way I look?" she chirped happily.
"Yes, you look very nice, my dear. Now let's go," he said. They went to the car and after seating her, he took his place in the driver's seat and they were off.
"Where are we going today, Sir?" she asked as they left the driveway and started down the street.
"You will find out. But I can tell you that you will enjoy it," he said, being very secretive.
"I'm sure I will Sir," she said, "You always show me such wonderful things!" Olivia could feel herself already getting damp with anticipation. Olivia's imagination started running wild and she conjured up all sorts of delicious scenarios that he could put her into. She didn't know what he had planned but she knew it had something to do with sex or D/s!
She was right on both counts. As he drove, he made his way to the subway station downtown. He pulled into the parking lot there and the attendant came out. Jack gave the guy the parking fee plus a good tip to take special care of his car. Then they walked across the lot and downstairs to the subway platform.
"Sir, can I ask why we need to take the subway? Why we can't just drive to wherever we are going?" she asked.
"The subway is part of the experience," was all he said. Olivia was puzzled. She had been on subways before and found them actually quite boring. There was nothing to look at except the other passengers and some of them were kinda scary sometimes! At least on the city's overhead rail you can look out the windows at the city below. What kind of "experience" could he be referring to?
They found a seat on one of the benches on the platform and sat down. Jack placed his hand on Olivia's thigh and he could feel her nervousness. He sensed her apprehension and he leaned over to her. "Just relax, my dear, I am here and you are safe," he whispered in her ear. She smiled inside knowing that she was with her Master and that he would protect and care for her. She felt the tension drain from her body and was able to relax after that.
Within and few minutes the train pulled into the station and they boarded. He took her to one end of the train car they were in as it filled to about three quarters full. This was a weekday so there were a lot of commuters, businessmen and women, and shoppers on board. Jack surveyed the crowd as they boarded and as the doors closed and they began to move, he was thankful that at least for now there were no children on this car.
It was time to make his move. He stood up and offered his hand to Olivia "Stand up dear," he said. She looked up curiously but she stood as he said. He pulled her in front of himself in the aisle between the rows of seats. Two grab poles stood beside her, one on each side and he made her grab onto them to steady herself on the rocking subway car. Then he leaned forward and whispered in a soft low growl in her ear, "It's show time!"
Jack yanked down the top of her off the shoulder top to her waist, and her breasts sprang free, her nipples instantly hardening in the cool air. Olivia gasped loudly as she was suddenly rendered topless in front of the whole car of people. He reached around her and began kneading her tits with his hands roughly. At first Olivia was mortified at his actions, but as he continued her horror turned to enjoyment and then to lust as his hands worked her soft creamy tits. Her gasps turned to soft moans then louder ones as she began to forget about the crowd and only concentrate on what he was doing to her.
Olivia felt her pussy getting wetter as he pinched and pulled her nipples, mauled her soft tit flesh and whispered lustful and erotic words in her ear.
"You are so fucking sexy, baby. I want to fuck you hard right here in front of everyone. I want to make the all these men want you and all these women want to be you. I want you to moan and scream and let everyone know how good your Master is at fucking your slutty pussy? Would you do that for me? Would you scream out my name as I fuck you here in front of these people?" he asked.
"Yes! Oh yes, Sir!" she moaned.
"Then ask me. Ask me to fuck you in front of these people so they can hear my pretty slut beg!" he said.
"Oh God Sir, please fuck me! Please fuck me right here and now! Oh pleease!" she begged loudly so everyone could hear.
He smiled at her obedience and hiking up her tight skirt over her hips he slid a finger, then two, into her now dripping slit.
"Ohhh Gawwwd!" she moaned as his fingered entered her and began churning inside her. She humped back against her hand, raising up on her toes to allow him in further. He plunged his digits into her over and over again, raising her lust even higher. She moaned and closed her eyes, shutting out everything but what was happening in her boiling cunt.
He fingered her pussy with one hand and played with her tit with the other as Olivia felt her passion fire quickly get out of control. She was a raging inferno in very short order, the anticipation having built up all morning. When he felt the time was right, he stopped fingering her pussy.
Olivia whimpered her disappointment - she had been close to cumming. But her disappointment was soon relieved when she felt the head of his cock sliding between her soft folds. "Ohhh God Sir! Please shove it into me! Fuck me Sir, please fuck meee!" she whined.
He rammed himself into her to the hilt in one powerful stroke that made her scream with pleasure. He no sooner hit bottom in her warm wet hole when he began fucking her hard and fast. By now they were well on their way to where they were headed and he couldn't waste any more time. He fucked her hard and fast and deep, making her grunt every time he slammed into her. She howled and squealed and cried out as he pounded her pussy like never before. She let go of one pole and began fingering her clit, trying desperately to reach orgasm before they arrived and had to stop. She needed to cum so bad...
"Please Master! Please make me cum! Oh God, I need to cum so badly! Please, Please make me cum!" she cried out as her hand flew over her clit. He pounded into her determined to do that very thing and within a few more moments she had reached the edge of her abyss. He reached around her once more and taking a pebble-hard nipple between his fingers he pinched her hard. making her scream out. But her scream also brought her the release she begged for.
"I'M CUUUUMMMINNGGG!!! OH, FUCKK MEEE!" she screeched as she erupted, her juices pouring out of her and running down her legs as her body convulsed and spasmed like she was going into seizures. She thrashed around, her head rolling and her legs shaking so violently, he had to hold her up with one arm and hold onto the pole with the other. Finally she went limp and he eased her down onto the seat, adjusting her clothes and holding her lovingly in his lap as she came back.
As the train pulled into the station, she was just coming to. She smiled weakly as people left the train car. Some of the older men smiled and winked at her, a few of the women left chattering to each other about the "outlandish display", and one woman in particular bent over and took her hand.
"Thank you, dear. I haven't cum like that in ages!" she said, giggling.
Jack and Olivia were the last ones off the train and he took her over to a bench on the subway platform for a few more minutes rest before they headed for the stairs up to street level. Once up on the street, he hailed a cab and gave the driver the address where he wanted to go. Olivia didn't recognize the address, but she was with Master and he had just given her an amazing orgasm so she was up for whatever would come along.
A few minutes later they pull up in front of the building that was his intended destination. Olivia looked out the window at the building. She was shocked again.
"Sir this... this is a sex toy store!" she whispered in his ear, as if afraid to tell the cab driver.
He chuckled, "Yes it is, Olivia dear. Now come on let's go," he said, getting out of the cab and paying the fare. The cab drove off and Jack and Olivia went inside. Jack took Olivia's hand once they went inside and he led her past shelves and display cases full of the widest assortment of dildos, vibrators and other sex toys she had ever seen. Her eyes got wider and wider as she surveyed aisle after aisle of products designed to heighten a person's sexual performance and enjoyment.
Jack led her through the store - his objective was in the back of the store. He led Olivia to a small room with a small padded stool next to what appeared to be an old bedside nightstand. "Have a seat Olivia," he said. Olivia did as he said still not certain to what end.
"Olivia this is what is known as a gloryhole. you see the walls in this room have holes in them at various heights and configurations. The hole are for men who come to visit this place to put their cocks through. Your job today is to make sure when they do they enjoy the experience," he said.
"Sir?" she asked not quite sure if she heard him right.
"That's right Olivia. When a cock comes through one of these holes, you are to suck it or if pops up in one of the lower holes, you will fuck it. And some holes may have a hand come through in which case you will let them play with your tits or finger your pussy. I am going out of the room for a minute to set up some eager cocks, but then I will be back I want to see how you do in this gloryhole," he said.
Olivia sat on the stool as she waited for something to happen. On the nightstand was a laminated sheet with what looked like instructions:
"Ring the bell for service. Lube and condoms can be found in the drawer below. Enjoy yourself!"
She picked up the little bell and gave it a timid shake. After a couple minutes, she saw what looked like an eye peering out through one of the holes.
"Take off your clothes - I want to make sure you are a woman!" the man's voice said. Olivia did what the voice told her, taking off the top and skirt she had worn. In response a very admirable cock popped through the hole. It was beautiful, and so hard. His cock was pink and the head was a reddish-purple. Olivia could feel the heat from it as she moved closer.
She gently reached out her hand and ran it softly from tip to base. The cock jumped at her touch and again she marveled at this wonderful piece of manhood. She softly squeezed it in her hand, and then applied pressure. A drop of precum oozed from the tip and she worked her hand across it, spreading the natural lubricant across the head. The man's cock jumped in her grasp as her palm rubbed the sensitive tip.
Olivia leaned forward and began licking the large cock. First she pushed her lips against the head in a kiss, then swirled her tongue all around it. Then she ran her tongue down the sensitive underside of his cock. She worked her hands and tongue around the shaft, milking and pumping it and then she slipped as much of it as she could into her hot, wet mouth.
She could hear the man behind the wall moaning his pleasure. His sounds, and the sexiness of the situation turned her on and spurred her to work harder. She continued sucking him in her mouth and sliding her hand along the shaft. Soon he was thrusting himself against the wall and she could tell he wouldn't be long.
She had just taken her mouth from his cock to take a deep breath when he slammed himself against the wall and a hot spurt of his semen hit her square in the chest, the cum sliding down her chest and down the valley between her lovely tits.
Olivia quickly took him in her mouth again, pumping his cock to get the next jet of cum. He reared back in her hand and she felt the stream hit the back of her throat. It was so hot in her mouth. She pulled back, and took the next spurt on her tits watching as the sticky white cum splashed over her hard nipple. She pumped another jet onto her tits and then took him in her mouth again, sucking the last of his cum out and cleaning his cock as she slowly drew back.
"Shit baby!" he muttered, out of breath. "That was the best I've ever had."
Olivia smiled and as he looked through the hole his cock previously occupied, she blew him a cum-covered kiss. Then she used her fingers to wipe off some of the cum dripping from her tits.
About that time Jack came back in the room. "I see you already had a customer," he said, seeing her sitting on her stool covered in cum and smiling broadly.
"Yes Sir, I took good care of him too!" she said proudly.
Then another cock popped through a different hole "Looks like you have another customer. Don't keep him waiting!" Jack said. Olivia turned to see a cock thrusting through the hole. This cock was a bit longer and more slender. It wasn't as pink but the head of his cock was as red as a rose. Olivia went right over to it and began sucking and playing with it for about five minutes before the owner moaned out that he was cumming.
This time she was ready and she pointed his cock at her open mouth. This man must not have cum in a good while because he really unloaded on her. She took as much as she could in her mouth, and then just let it shoot onto her cheeks and chin until it dripped down onto her naked breasts.
While she waited on the next guy, Olivia smeared some of the cum across her chest. She brought her cum-covered fingers up to her nose and breathed in the musky scent. She loved it all.
She had just taken her cum-slickened fingers down to rub her pussy lips when another cock popped out through the hole.
This man's cock was of average length, but really thick, and there wasn't a lot of space left in the hole as his cock extended through. Olivia couldn't open her mouth wide enough to take it all in for long, so she really worked him over good with her lips, tongue and hands.
When he finally came, Olivia thought he was going to push the wall down on her. He really slammed into that hole hard. Everyone comes different, especially with age, but she was surprised by his huge ribbons of cum that sprayed out onto her face. It was a slick liquid and it was hard to control the direction. He really covered her face! It was so wild. She quickly ran a free hand down to her clit and almost came before he pulled back through the hole.
Olivia was pretty well covered with cum by now. She had cum on her face, in her hair, and all over her chest and tits. She had swallowed some of each man's load and she was smiling through it all.
"Okay, Olivia this next guy will be your last customer for today. We can come back another time if you want to play some more," he said.
"Yes! I would love that, Sir!" Olivia said excitedly.
They waited a few minutes and were just about to leave when her last customer finally arrived.
After her latest customer put his cock through the wall, Olivia played with it for a few minutes with her hands. She caressed and massaged it. She squeezed it, milking it until the drops of precum oozed from the light purple head. She combined the liquid precum with her tongue and soon had the hard cock slipping through her tight hand. Olivia was really getting into this. Suddenly she had an idea.
She let go of his cock and quickly stood up and bent over with her ass to the hole. She backed up until she felt the heat of his cock at her wet pussy. She worked his cock slowly up and down her pussy lips, parting them and just letting him slip in about a half inch and then pulling back out again.
"Ohhhhh, fuck baby..." she heard him mumble. She took a deep breath and pushed back until his cock was buried deep inside her. She adjusted to the feel of it, and let her inner muscles squeeze him once and then she pulled away. She hadn't planned on going that far, but she saw her Master sitting there watching her with a smile on his face. She so wanted to please him - especially after her recent disobedience. She knew he would keep her safe and so she needn't be afraid. And to be honest, she was so turned on - she just had to know what this cock felt like inside of her. She pushed back hard against the wall hoping to get him deeper in her eager pussy. He felt wonderful and both of them were moaning as he pumped into her through the wonderful gloryhole. She worked his cock with her pussy muscles until she felt him ready to cum.
"C'mon... come in me. Come in my pussy baby," she whispered. She pumped his cock until he came hard, shooting jet after jet of creamy white semen deep into her.
When his cock pulled out, she stuck her finger through the hole, beckoning him to come closer. When his finger hooked around hers, she pulled it through the hole. She stood up and awkwardly pushed her body against the wall, spreading her legs wide. She directed his finger to her pussy.
He knew right away what he felt and he began fingering her clit. She was so wet that his finger was quickly covered with her slick juices. In seconds, she was cumming hard and she slammed her body up against the wall just like the men had earlier.
The man pulled his finger back through the hole, but Olivia wasn't finished with him just yet.
"Cock!" Olivia moaned. "Please give me your cock! Stick it back in!"
The man obeyed. Already hard again, he stuck his cock back through the hole and Olivia clamped down onto it with her pussy. She adjusted herself until the head of his cock was just inside her pussy lips and resting against her clit.
"Mmmmmm" she moaned in appreciation. She stood there for a minute, just enjoying the pressure from his hot cock against her clit. The man stuck a hand out through another hole and she moved a bit so that he could fondle her tit. Olivia rubbed up against the wall, letting his cock massage her pussy. Finally, the tremors from her orgasm slowing, she stepped away. She knelt down and sucked her juices off his cock before the man stumbled back, stuffed his erection back into his pants, and left.
Oliva sat back on her stool, smiling happily. Jack came up to her standing in front of her looking down into her smiling, cum-covered face. "Did you have fun, my dear?" he asked.
"Oh yes, Sir! I had so much fun! Thank you for bringing me here. I hope we can come back here - I want to do this again!" she said.
"Well I'm glad you had a good time. And we will definitely come back here again - I like seeing my sweet slut covered in sticky hot cum! It makes you look even prettier and sexier," he said.
"Thank you Sir," she said, blushing a bit. She picked up her clothes and got dressed. He wanted her to leave the cum on her tits, but let her go into the bathroom to clean her face. Olivia scooped off a little of the cum on her face just to taste her men-friends again, and then finished up so they could leave. On the way out, they stopped at the checkout counter and he paid for the use of the gloryhole room.
"What do you think you are doing?" he said startling Olivia.
When Olivia looked up, she was surprised that Jack was watching her toy with her pussy. She instantly sat up on her bed.
"I-I was just..." she started to say.
"You were just playing with yourself without my permission, weren't you young lady?" he finished her statement.
"Y-yes Sir," she said, looking down.
"Haven't I told you before that you are not to play with your pussy unless I tell you to? Haven't I said that your orgasms were my gift to you and you are not to cum without my permission?" he said.
"Yes Sir, I'm sorry I just... needed to," she said, apologetically.
"Then you should have come to me and said something. Now go to your room and stand in your corner and think about what you've done while I decide how I am to punish you. Do not come out until I call you. Now move," he commanded.
Olivia slunk down the hall into her room and stood in the corner as he commanded wondering what was to become of her.
Jack, meanwhile went into his office to think of what punishment, he would use on his Olivia. He didn’t want to be too harsh on her first punishment. He sat in his office for a few minutes. Ten minutes later he came out of his office with his punishment for his naughty Olivia. He called her back into the living room and as she came in he told her to come stand in front of him.
"Olivia I have decided what needs to be done. Since this is your first punishment, I will be a little easier on you, but if this happens again, I will give you the full punishment. Do you understand?"
"Yes Sir," she said anxiously.
"Good. Now hike up your skirt and drop your panties and lay over my knees. I am going to spank your bare ass,” he demanded.
Olivia dropped her skirt and panties and she laid over Jack’s knees. He rubbed her ass with some baby oil.
He gave the first swat on one ass cheek and Olivia squealed, "One, Sir." squirming on his lap. He let the burn sink in a bit before he gave her another swat on the other cheek. Olivia squealed again, "Two, Sir. He gave her four more swats alternating ass cheeks. Then he rubbed her ass before giving her the remaining four. Olivia counted each one as she was told.
After her spanking Jack told Olivia, Get on your knees and sit in between my knees. Jack grabbed her chin and locked eyes with her.
“Olivia, you know what you did was wrong don’t you?” he said.
“Yes, Sir. I had orgasm that wasn’t given by you. I broke the rules and I deserved that punishment. I’m sorry for disobeying you.” she said, contritely
“I know you’re sorry little one but I’m still mad at you. I still love you, though, that’s not going to change Olivia. Now get on the bed on all fours,”
Olivia got on the bed on all fours waiting for him. He got on the bed and just shoved his cock deep inside her pussy, owning it and claiming it for his own pleasurable needs. Since Olivia already had her orgasm, Jack fucked her like a fuck doll that she was. He didn’t waste any time to get down to business using her to his advantage. She moaned out from being used for his personal use.
Then he flipped her over as he pinned her arms above her head as he pounded her creamy milky pussy raw and bare. Olivia moaned out in pleasure, screaming out in pure ecstasy and causing her to cum. But not for her pleasure, though, it was for his pleasure and his pleasure only. He came in her as he continued to fuck her like a savage. Teaching her that her orgasm is a very special gift only to be given by him.
“Olivia, darling you came twice you little greedy slut,” he said
“Yes, Sir. I learned my lesson, no more giving myself an orgasm that’s not from you,” she said
“Good girl.”
. . . . .
The next morning at breakfast, Olivia seemed troubled. Jack noticed but didn't say anything, figuring she would when she felt like it. But breakfast was served and ate it without her saying anything. After breakfast was over, Jack went into the living room as was his custom to read the newspaper while Olivia cleared the table and put the dishes in the dishwasher. Then she came into the living room and sat down on the sofa to watch TV.
Still having said nothing all morning, Jack folded his newspaper and set it aside. "Olivia come here," he said. Olivia looked at him then quietly came over and knelt in front of him as she had been taught.
"Olivia, you haven't said two words all morning. Now I know something is bothering you and until now I have kept quiet about it. But no more. Now I want to know what has your mind so troubled," he said.
"It's about what happened yesterday, Sir," she said.
"What happened yesterday?" he asked, not understanding the problem yet.
"Yes, Sir. When you caught me masturbating, and spanked me for it," she said.
"Yes I did. But then after the spanking I said the matter was over. What's the problem?" he asked.
"Well Sir, I was just wondering... why you were so easy on me with my punishment," Olivia said, looking up at him.
"Olivia this was the first time you disobeyed me like that. I couldn't very well spank you like you had done it repeatedly. Had this been a recurring thing, your punishment would have been considerably harder. But for a first offense I felt it was adequate," he said.
"Yes Sir," she said, "Only..."
"What is it, Olivia?"
"Sir may I ask you for another spanking?" she said.
"You want another spanking?" he said.
Yes, Sir. And this time don't be so easy on me," Olivia said.
"Why would you want another spanking?" he asked.
"Sir, I knew that you told me I wasn't to masturbate without your permission. But I did it anyway. I told you I couldn't help it - that I needed to, and it's true, after being denied an orgasm for so long, I was about to bust. But I am a submissive and you are my Master - I should have come to you and explained my needs. There is no excuse for my behavior. And because you went easy on me for it, makes it all the worse. It's almost like you ignored my disobedience or rewarded me for it. I need to be punished for disobeying you, Sir. And I need to feel like I was punished if I am to learn to control myself for you. Do you understand, Sir?" Olivia explained.
"I think I do, Olivia. Very well, you shall have your proper spanking this evening then. I want you to feel that your punishment was appropriate as well," he said.
"Thank you Sir," Olivia said.
But before that happens we have things to do. So go upstairs and get dressed. Wear that white off the shoulder crop top you have and your short black mini-skirt - the one that fits so tight I can tell if you're wearing panties under it! Oh and don't be!" he said. Olivia smiled; usually when he specified what she was to wear, he had a reason for it!
Olivia went to the bedroom and got dressed as he requested. She didn't wear a bra or panties as he had directed and she put on her clothes then went in to apply her makeup and finish getting ready. She didn't know what he had planned but she knew it was going to be sexy and exciting!
She came out of the bathroom to find him already dressed and ready to go. "I'm already Sir, do you like the way I look?" she chirped happily.
"Yes, you look very nice, my dear. Now let's go," he said. They went to the car and after seating her, he took his place in the driver's seat and they were off.
"Where are we going today, Sir?" she asked as they left the driveway and started down the street.
"You will find out. But I can tell you that you will enjoy it," he said, being very secretive.
"I'm sure I will Sir," she said, "You always show me such wonderful things!" Olivia could feel herself already getting damp with anticipation. Olivia's imagination started running wild and she conjured up all sorts of delicious scenarios that he could put her into. She didn't know what he had planned but she knew it had something to do with sex or D/s!
She was right on both counts. As he drove, he made his way to the subway station downtown. He pulled into the parking lot there and the attendant came out. Jack gave the guy the parking fee plus a good tip to take special care of his car. Then they walked across the lot and downstairs to the subway platform.
"Sir, can I ask why we need to take the subway? Why we can't just drive to wherever we are going?" she asked.
"The subway is part of the experience," was all he said. Olivia was puzzled. She had been on subways before and found them actually quite boring. There was nothing to look at except the other passengers and some of them were kinda scary sometimes! At least on the city's overhead rail you can look out the windows at the city below. What kind of "experience" could he be referring to?
They found a seat on one of the benches on the platform and sat down. Jack placed his hand on Olivia's thigh and he could feel her nervousness. He sensed her apprehension and he leaned over to her. "Just relax, my dear, I am here and you are safe," he whispered in her ear. She smiled inside knowing that she was with her Master and that he would protect and care for her. She felt the tension drain from her body and was able to relax after that.
Within and few minutes the train pulled into the station and they boarded. He took her to one end of the train car they were in as it filled to about three quarters full. This was a weekday so there were a lot of commuters, businessmen and women, and shoppers on board. Jack surveyed the crowd as they boarded and as the doors closed and they began to move, he was thankful that at least for now there were no children on this car.
It was time to make his move. He stood up and offered his hand to Olivia "Stand up dear," he said. She looked up curiously but she stood as he said. He pulled her in front of himself in the aisle between the rows of seats. Two grab poles stood beside her, one on each side and he made her grab onto them to steady herself on the rocking subway car. Then he leaned forward and whispered in a soft low growl in her ear, "It's show time!"
Jack yanked down the top of her off the shoulder top to her waist, and her breasts sprang free, her nipples instantly hardening in the cool air. Olivia gasped loudly as she was suddenly rendered topless in front of the whole car of people. He reached around her and began kneading her tits with his hands roughly. At first Olivia was mortified at his actions, but as he continued her horror turned to enjoyment and then to lust as his hands worked her soft creamy tits. Her gasps turned to soft moans then louder ones as she began to forget about the crowd and only concentrate on what he was doing to her.
Olivia felt her pussy getting wetter as he pinched and pulled her nipples, mauled her soft tit flesh and whispered lustful and erotic words in her ear.
"You are so fucking sexy, baby. I want to fuck you hard right here in front of everyone. I want to make the all these men want you and all these women want to be you. I want you to moan and scream and let everyone know how good your Master is at fucking your slutty pussy? Would you do that for me? Would you scream out my name as I fuck you here in front of these people?" he asked.
"Yes! Oh yes, Sir!" she moaned.
"Then ask me. Ask me to fuck you in front of these people so they can hear my pretty slut beg!" he said.
"Oh God Sir, please fuck me! Please fuck me right here and now! Oh pleease!" she begged loudly so everyone could hear.
He smiled at her obedience and hiking up her tight skirt over her hips he slid a finger, then two, into her now dripping slit.
"Ohhh Gawwwd!" she moaned as his fingered entered her and began churning inside her. She humped back against her hand, raising up on her toes to allow him in further. He plunged his digits into her over and over again, raising her lust even higher. She moaned and closed her eyes, shutting out everything but what was happening in her boiling cunt.
He fingered her pussy with one hand and played with her tit with the other as Olivia felt her passion fire quickly get out of control. She was a raging inferno in very short order, the anticipation having built up all morning. When he felt the time was right, he stopped fingering her pussy.
Olivia whimpered her disappointment - she had been close to cumming. But her disappointment was soon relieved when she felt the head of his cock sliding between her soft folds. "Ohhh God Sir! Please shove it into me! Fuck me Sir, please fuck meee!" she whined.
He rammed himself into her to the hilt in one powerful stroke that made her scream with pleasure. He no sooner hit bottom in her warm wet hole when he began fucking her hard and fast. By now they were well on their way to where they were headed and he couldn't waste any more time. He fucked her hard and fast and deep, making her grunt every time he slammed into her. She howled and squealed and cried out as he pounded her pussy like never before. She let go of one pole and began fingering her clit, trying desperately to reach orgasm before they arrived and had to stop. She needed to cum so bad...
"Please Master! Please make me cum! Oh God, I need to cum so badly! Please, Please make me cum!" she cried out as her hand flew over her clit. He pounded into her determined to do that very thing and within a few more moments she had reached the edge of her abyss. He reached around her once more and taking a pebble-hard nipple between his fingers he pinched her hard. making her scream out. But her scream also brought her the release she begged for.
"I'M CUUUUMMMINNGGG!!! OH, FUCKK MEEE!" she screeched as she erupted, her juices pouring out of her and running down her legs as her body convulsed and spasmed like she was going into seizures. She thrashed around, her head rolling and her legs shaking so violently, he had to hold her up with one arm and hold onto the pole with the other. Finally she went limp and he eased her down onto the seat, adjusting her clothes and holding her lovingly in his lap as she came back.
As the train pulled into the station, she was just coming to. She smiled weakly as people left the train car. Some of the older men smiled and winked at her, a few of the women left chattering to each other about the "outlandish display", and one woman in particular bent over and took her hand.
"Thank you, dear. I haven't cum like that in ages!" she said, giggling.
Jack and Olivia were the last ones off the train and he took her over to a bench on the subway platform for a few more minutes rest before they headed for the stairs up to street level. Once up on the street, he hailed a cab and gave the driver the address where he wanted to go. Olivia didn't recognize the address, but she was with Master and he had just given her an amazing orgasm so she was up for whatever would come along.
A few minutes later they pull up in front of the building that was his intended destination. Olivia looked out the window at the building. She was shocked again.
"Sir this... this is a sex toy store!" she whispered in his ear, as if afraid to tell the cab driver.
He chuckled, "Yes it is, Olivia dear. Now come on let's go," he said, getting out of the cab and paying the fare. The cab drove off and Jack and Olivia went inside. Jack took Olivia's hand once they went inside and he led her past shelves and display cases full of the widest assortment of dildos, vibrators and other sex toys she had ever seen. Her eyes got wider and wider as she surveyed aisle after aisle of products designed to heighten a person's sexual performance and enjoyment.
Jack led her through the store - his objective was in the back of the store. He led Olivia to a small room with a small padded stool next to what appeared to be an old bedside nightstand. "Have a seat Olivia," he said. Olivia did as he said still not certain to what end.
"Olivia this is what is known as a gloryhole. you see the walls in this room have holes in them at various heights and configurations. The hole are for men who come to visit this place to put their cocks through. Your job today is to make sure when they do they enjoy the experience," he said.
"Sir?" she asked not quite sure if she heard him right.
"That's right Olivia. When a cock comes through one of these holes, you are to suck it or if pops up in one of the lower holes, you will fuck it. And some holes may have a hand come through in which case you will let them play with your tits or finger your pussy. I am going out of the room for a minute to set up some eager cocks, but then I will be back I want to see how you do in this gloryhole," he said.
Olivia sat on the stool as she waited for something to happen. On the nightstand was a laminated sheet with what looked like instructions:
"Ring the bell for service. Lube and condoms can be found in the drawer below. Enjoy yourself!"
She picked up the little bell and gave it a timid shake. After a couple minutes, she saw what looked like an eye peering out through one of the holes.
"Take off your clothes - I want to make sure you are a woman!" the man's voice said. Olivia did what the voice told her, taking off the top and skirt she had worn. In response a very admirable cock popped through the hole. It was beautiful, and so hard. His cock was pink and the head was a reddish-purple. Olivia could feel the heat from it as she moved closer.
She gently reached out her hand and ran it softly from tip to base. The cock jumped at her touch and again she marveled at this wonderful piece of manhood. She softly squeezed it in her hand, and then applied pressure. A drop of precum oozed from the tip and she worked her hand across it, spreading the natural lubricant across the head. The man's cock jumped in her grasp as her palm rubbed the sensitive tip.
Olivia leaned forward and began licking the large cock. First she pushed her lips against the head in a kiss, then swirled her tongue all around it. Then she ran her tongue down the sensitive underside of his cock. She worked her hands and tongue around the shaft, milking and pumping it and then she slipped as much of it as she could into her hot, wet mouth.
She could hear the man behind the wall moaning his pleasure. His sounds, and the sexiness of the situation turned her on and spurred her to work harder. She continued sucking him in her mouth and sliding her hand along the shaft. Soon he was thrusting himself against the wall and she could tell he wouldn't be long.
She had just taken her mouth from his cock to take a deep breath when he slammed himself against the wall and a hot spurt of his semen hit her square in the chest, the cum sliding down her chest and down the valley between her lovely tits.
Olivia quickly took him in her mouth again, pumping his cock to get the next jet of cum. He reared back in her hand and she felt the stream hit the back of her throat. It was so hot in her mouth. She pulled back, and took the next spurt on her tits watching as the sticky white cum splashed over her hard nipple. She pumped another jet onto her tits and then took him in her mouth again, sucking the last of his cum out and cleaning his cock as she slowly drew back.
"Shit baby!" he muttered, out of breath. "That was the best I've ever had."
Olivia smiled and as he looked through the hole his cock previously occupied, she blew him a cum-covered kiss. Then she used her fingers to wipe off some of the cum dripping from her tits.
About that time Jack came back in the room. "I see you already had a customer," he said, seeing her sitting on her stool covered in cum and smiling broadly.
"Yes Sir, I took good care of him too!" she said proudly.
Then another cock popped through a different hole "Looks like you have another customer. Don't keep him waiting!" Jack said. Olivia turned to see a cock thrusting through the hole. This cock was a bit longer and more slender. It wasn't as pink but the head of his cock was as red as a rose. Olivia went right over to it and began sucking and playing with it for about five minutes before the owner moaned out that he was cumming.
This time she was ready and she pointed his cock at her open mouth. This man must not have cum in a good while because he really unloaded on her. She took as much as she could in her mouth, and then just let it shoot onto her cheeks and chin until it dripped down onto her naked breasts.
While she waited on the next guy, Olivia smeared some of the cum across her chest. She brought her cum-covered fingers up to her nose and breathed in the musky scent. She loved it all.
She had just taken her cum-slickened fingers down to rub her pussy lips when another cock popped out through the hole.
This man's cock was of average length, but really thick, and there wasn't a lot of space left in the hole as his cock extended through. Olivia couldn't open her mouth wide enough to take it all in for long, so she really worked him over good with her lips, tongue and hands.
When he finally came, Olivia thought he was going to push the wall down on her. He really slammed into that hole hard. Everyone comes different, especially with age, but she was surprised by his huge ribbons of cum that sprayed out onto her face. It was a slick liquid and it was hard to control the direction. He really covered her face! It was so wild. She quickly ran a free hand down to her clit and almost came before he pulled back through the hole.
Olivia was pretty well covered with cum by now. She had cum on her face, in her hair, and all over her chest and tits. She had swallowed some of each man's load and she was smiling through it all.
"Okay, Olivia this next guy will be your last customer for today. We can come back another time if you want to play some more," he said.
"Yes! I would love that, Sir!" Olivia said excitedly.
They waited a few minutes and were just about to leave when her last customer finally arrived.
After her latest customer put his cock through the wall, Olivia played with it for a few minutes with her hands. She caressed and massaged it. She squeezed it, milking it until the drops of precum oozed from the light purple head. She combined the liquid precum with her tongue and soon had the hard cock slipping through her tight hand. Olivia was really getting into this. Suddenly she had an idea.
She let go of his cock and quickly stood up and bent over with her ass to the hole. She backed up until she felt the heat of his cock at her wet pussy. She worked his cock slowly up and down her pussy lips, parting them and just letting him slip in about a half inch and then pulling back out again.
"Ohhhhh, fuck baby..." she heard him mumble. She took a deep breath and pushed back until his cock was buried deep inside her. She adjusted to the feel of it, and let her inner muscles squeeze him once and then she pulled away. She hadn't planned on going that far, but she saw her Master sitting there watching her with a smile on his face. She so wanted to please him - especially after her recent disobedience. She knew he would keep her safe and so she needn't be afraid. And to be honest, she was so turned on - she just had to know what this cock felt like inside of her. She pushed back hard against the wall hoping to get him deeper in her eager pussy. He felt wonderful and both of them were moaning as he pumped into her through the wonderful gloryhole. She worked his cock with her pussy muscles until she felt him ready to cum.
"C'mon... come in me. Come in my pussy baby," she whispered. She pumped his cock until he came hard, shooting jet after jet of creamy white semen deep into her.
When his cock pulled out, she stuck her finger through the hole, beckoning him to come closer. When his finger hooked around hers, she pulled it through the hole. She stood up and awkwardly pushed her body against the wall, spreading her legs wide. She directed his finger to her pussy.
He knew right away what he felt and he began fingering her clit. She was so wet that his finger was quickly covered with her slick juices. In seconds, she was cumming hard and she slammed her body up against the wall just like the men had earlier.
The man pulled his finger back through the hole, but Olivia wasn't finished with him just yet.
"Cock!" Olivia moaned. "Please give me your cock! Stick it back in!"
The man obeyed. Already hard again, he stuck his cock back through the hole and Olivia clamped down onto it with her pussy. She adjusted herself until the head of his cock was just inside her pussy lips and resting against her clit.
"Mmmmmm" she moaned in appreciation. She stood there for a minute, just enjoying the pressure from his hot cock against her clit. The man stuck a hand out through another hole and she moved a bit so that he could fondle her tit. Olivia rubbed up against the wall, letting his cock massage her pussy. Finally, the tremors from her orgasm slowing, she stepped away. She knelt down and sucked her juices off his cock before the man stumbled back, stuffed his erection back into his pants, and left.
Oliva sat back on her stool, smiling happily. Jack came up to her standing in front of her looking down into her smiling, cum-covered face. "Did you have fun, my dear?" he asked.
"Oh yes, Sir! I had so much fun! Thank you for bringing me here. I hope we can come back here - I want to do this again!" she said.
"Well I'm glad you had a good time. And we will definitely come back here again - I like seeing my sweet slut covered in sticky hot cum! It makes you look even prettier and sexier," he said.
"Thank you Sir," she said, blushing a bit. She picked up her clothes and got dressed. He wanted her to leave the cum on her tits, but let her go into the bathroom to clean her face. Olivia scooped off a little of the cum on her face just to taste her men-friends again, and then finished up so they could leave. On the way out, they stopped at the checkout counter and he paid for the use of the gloryhole room.
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