Old Friends Ch. 02

Yesterday was so empowering. So many years, dating guys that didn't appreciate or come close to satisfying her, she'd grown disgusted with sex altogether. But yesterday had made her feel great and so damn horny. Oh how she had wanted to have him inside her, fucking her to her very core. But that would only undermine her plans. No, he would work for that privilege. She wasn't going to make the mistake of giving too much too soon ever again. He had looked so hot and sexy, though. Time had done little to ruin his good looks.

I wonder if he'll show up again. But she had little reason to worry as Ryan was leaving his apartment, heading for the hotel as she sat daydreaming.

As he drove along, he realized he had remembered little from work that day, as he could not get Mistress Nora off his mind. He had gone home the night before, both satisfied and frustrated. As he stood in the bathroom, cleaning and storing his items, he had wondered why she hadn't shown him her face. Not that it mattered, he was so taken by her, he didn't care. But still he felt such a strong connection that he wanted to see her in person and in his dreams.

He reached the hotel and walked quickly to the desk, not even looking around this time. He retrieved an envelope and proceeded to the room. As he entered the room, he opened the envelope and read: Take off all your clothes, put on the mask and collar. Get down on all fours, facing the opposite direction as yesterday and place the stimulator into your asshole. You may suck on and lick it to get it wet so it will enter easily. It must be placed, as yesterday, fully inside you. Then wait for arrival quietly and obediently.

Though he licked and got the anal insert as wet as he could, it still hurt going in but he didn't care. He did as he was told and anxiously waited quietly for his Mistress.

This time, it was only moments before he heard the door. Again he heard a bag drop to the floor next to the bed. He waited but said nothing. "Good evening, my pet, are you happy I am home?"

"Yes, Mistress," he said excitedly.

"Good boy," she cooed, as she petted him on the head. "Now be a good pet and say hello to Mistress Celeste."

Mistress Celeste? What was going on? He knew not to ask and hesitantly said, "Hello, Mistress Celeste."

At that he heard a stern female voice address Mistress Nora, "hmmm, Mistress Nora, he is a fine specimen. Nice body, good sized cock, not big but not small either. You chose well for your first pet. But today we will find out if he is truly worthy and obedient, won't we?"

"Yes, Mistress Celeste, we certainly will," she said.

Again a fear crept up from his belly, as he was confused as to what was about to happen.

"Today, my pet, Mistress Celeste is your Mistress. You will do as you are told and be obedient. Not only will you receive punishment at her hands for your insubordinations, after she leaves I will punish you for embarrassing me. Do you understand, pet?" Mistress Nora quipped.

"Yes, Mistress, I understand." He said hesitantly.

"Good then," barked Mistress Celeste, as she walked up behind him and dropped something on the bed next to him. "I thought you said he was naughty, why that hard on he's starting is hardly a reason for a woman to stay awake. Perhaps, he is disappointed that he won't be at your hands Mistress Nora. Is that why you aren't cock ready, pet?"

"No Mistress Celeste."

"Well then," pondered Mistress Celeste, "perhaps we need to help you with that." He heard her rummaging through the bag on the bed then she stepped behind him and removed the stimulator from his rectum. Suddenly he felt rough hands prying his cheeks apart, as cold gel was squirted liberally on his tender hole. She roughly began rubbing it but he couldn't tell with what or anything about what she was using. Just as quickly as she began rubbing she inserted, what felt like a full sized cock into his asshole. Not entirely rough but uncomfortable and painful, nonetheless. A gasp of pain erupted from his mouth before he could stop himself. SLAP—he felt the flat surface of a paddle hit his ass with great force.

"Did I give you permission to make any sounds, pet?" Mistress Celeste demanded.

"No Mistress, you did not."

"Do not make that mistake again."

"Yes Mistress", he whispered, fighting back tears as he wondered what the hell he was doing there. He could just get up and leave but he didn't want to. He desperately wanted to please Mistress Nora. He wanted the rewards that she had to offer. He wanted her approval.

He had barely caught his breath when he felt something cold and metallic on his nipples. One then the other was tightened until pain shot through his chest and yet, he could feel himself becoming more and more aroused. How could that be? This woman was torturing him and yet his member was responding to the senses of pain and pleasure coursing through his body.

"Well, well, I see we are getting somewhere," stated Mistress Celeste.

Thank God, he thought, she sounds like she approves and we can move on to better things.

"On the bed on your back, pet, but don't let that dildo fall out." Mistress Celeste quipped.

Slowly, Ryan rose up, still blind to who was there and crawled onto the bed. As he was rolling over on his back, he felt the dildo begin to slip out. Before he could do anything, out it shot onto the mattress.

Mortified, he began to apologize but it was to no avail. Mistress Celeste grabbed the chain on his collar and swiftly flipped him over her leg. As he landed on her lap, he realized though soft and cuddly feeling under him, this woman had more strength than most men he knew. As she positioned him on her lap, his hard dick slipped between her thighs lightly touching her massive bush and he could feel her wetness against him. Though part of him was freaking out, the other part was getting more and more turned on.

SLAP, SLAP, SLAP...each one harder than the last, she administered his punishment with the wooden paddle soundly.

"Pet, you got your ass juices on my bed," and as Mistress Celeste returned him to the bed, she pushed his face into the mattress, "you will lick it up before we proceed."

"Yes Mistress," he panted and began licking where she placed his face. It smelled like his ass yet that didn't seem to bother him. How odd, he thought. The whole time he was licking he couldn't help but feel extremely conscious of the stinging of his ass. He could feel the heat radiating and yet it only served to make his cock grow harder than before. Knowing he was completely nude with his ass in the air and his face in the bed, he knew it had to be obvious. But where was Mistress Nora? Was she still in the room or had she left him with this Mistress? He trusted Mistress Nora but knew nothing of Mistress Celeste. He knew he had to trust that his Mistress would not allow harm to come to him so he would proceed as Mistress Nora had instructed.

"Good boy, now roll over onto your back and bring your knees to your chest." Mistress Celeste instructed.

He quickly did as he was told. Even though he was beginning to enjoy the spankings, they were getting harder and he feared that she would splinter the paddle into his ass if he pushed her. As he laid on his back, he could feel Mistress Celeste move into position kneeling just below his feet and ass. He hoped he didn't have to hold this position long. As that thought entered his mind, he felt the full force of the dildo being shoved deep into his ass. The pain was excruciating; she hadn't put any additional lube on it so only what little, if anything, that had been left on it when it escaped his ass, as she shoved it into him. He bit his lip not wanting to cry out and risk further punishment.

"You like that, don't you, my pet?" Mistress Nora whispered in his ear, startling him. He hadn't even heard her in the room nor known she had come to the side of the bed.

"Yes, Mistress, I do."

"Tell me you want Mistress Celeste to fuck your asshole."

Taking a deep breath, he did his best not to let his voice quiver, "Yes, please"

"Yes, what?"

"Yes, Mistress, I want Mistress Celeste to fuck my ass, please."

"Of course, you do, my pet," Mistress Nora purred into his ear.

As Mistress Nora began sucking and licking his ear, Mistress Celeste began sliding the dildo in and out of Ryan's tight asshole. At first it felt uncomfortable but as she continued, he began to reach a feeling that made his head swim and his groin grow hotter. As she pumped away at his ass with the dildo, he began gyrating as if trying to hump the air. He needed to cum so bad....he felt close to the edge with the hot lips of Misstress Nora now on his nipples protruding from the nipple clamps, he knew he wouldn't make it much longer.

Then as quickly as he began to reach his peak, Mistress Nora stopped and so did Mistress Celeste. She promptly pushed the dildo back into his ass and told him to put his legs flat on the bed.

"What the fuck" his mind was screaming. He had been on the verge of a glorious orgasm and now back to square one with his cock so hard he truly thought it would bust any moment. But he did as he was told, laying on his back panting and frustrated.

Just as he was catching his breath, Mistress Celeste squatted down over his face and told him to begin licking and sucking her pussy. He felt suffocated as her girth settled onto his face and he could already taste her juices seeping out. But he began sucking and licking, trying desperately to satisfy her quickly so he could breathe easy again.

"mmmm, now there's a good boy," she said in a throaty voice as she rocked back and forth across his mouth, "now you may slide two fingers into my pussy and fuck me with your fingers but don't stop sucking and licking. You will make me cum on your face then lick my pussy clean when you are done."

He could say nothing with his mouth full of her, but did as he was told, sliding two fingers into her hot wetness, making sure to keep licking and sucking as he moved rapidly in and out of her with his digits.

With a grunt and scream, she came all over his face and patiently waited as he licked her clean. As she moved herself from his face, she instructed him to get on his knees facing the door. This time he was extremely careful to keep the dildo in his ass, lest he give her another reason to punish him.

As he got into position, he could feel Mistress Celeste lay in front of him and place her knees on either side of his hips.

"You may remove your mask, pet" she said.

Finally! He hoped Mistress Nora had not left the room. He so desperately wanted to look at her and memorize her. As he removed the mask and adjusted his eyes to the barely lit room, he could see Mistress Celeste laying on the bed in front of him. A plain faced big woman, she was not unattractive yet not attractive either. Her plain brown hair spread around her head as she looked at him blandly with her brown eyes.

As he glanced up, he could see a shapely woman sitting in a chair, looking at him from behind a black hooded mask. He could barely make out her mouth, eyes and nose poking out of the faceholes. DAMN! He thought....still he didn't get to see her. Just then, he felt the sharp pain of Mistress Celeste grabbing the nipple clips still attached to his tender male bosom.

"Did I tell you that you could look at Mistress Nora?" she demanded.

"No, Mistress. I am sorry."

"Hmmm, I must think. Now, I am not sure you are worthy to fuck my pussy. Do you want to fuck me, pet?" she questioned.

"Yes, Mistress, please."

"Tell me then...tell me what you want to do to my pussy."

"Mistress, I want to put my hard cock in your pussy and make you cum all over me."

"I will allow it but you must not cum until I tell you that you can. Do you understand?"

"Yes, Mistress", he assured her. At this point he wanted to fuck anything so he could get rid of this overwhelming struggle within his body straining at his prick.

"You may fuck me, pet."

Without a second's hesitate, he plunged deep inside of her, making her gasp in approval. Though still holding his ass tight, he was desperate to make her cum so she would let him cum and end this agony. But as trained Mistress, she had no intention of letting him off that easily. He would have to work to make her orgasm.

As he pumped away, struggling not to cum himself, as he was so close to the edge of insanity, she asked him, "is there something else you want to do, to help me cum, pet?"

"Yes, Mistress," he panted out, still focusing to maintain control.

"You may ask permission."

"May I please rub your pussy and play with your tits, while I fuck you, Mistress?"

"There's a good boy, asking so nicely. What do you think Mistress Nora? Has he behaved enough to your liking to earn that privilege?"

Mistress Nora hesitated, as if thinking it over, as Ryan continued to pump away, knowing he could not stop anything he was doing in response, nor could he plead with her to let him. He could only wait for her response.

"I believe," Mistress Nora started, "that he may do one or the other but not both. After all he has made some serious errors today. I will leave it up to you, Mistress Celeste to decide which."

"I do believe he has paid enough attention to my pussy so far so, pet, you have my permission to play with my breasts. You may even suck and lick them, too." Mistress Celeste informed him.

He wasted no time as he grabbed one large breast in his hand and began licking and sucking like a starving infant. He was desperately trying to bring her to climax and would do anything. Finally, several minutes later, Mistress Celeste allowed herself to orgasm with a loud moan, as she wrapped her legs around him and thrust her hips forward. It was more than he could take, without warning, or permission, he shot his load full into Mistress Celeste and immediately regretted his weakness.

"Mistress Celeste, I'm sorry. It will never happen again, "he burst out.

By this time, Mistress Nora was standing in front of the bed, where Mistress Celeste lay and Ryan looked down profusely apologizing.

"Enough!" exclaimed Mistress Nora. She grabbed the chain and pulled his face to hers. He could still only see her eyes, nose and mouth, but now realized that she was completely nude, with perky round breasts, a slightly staunch belly and a beautiful black bush. She stood before him like a goddess but he could see the anger in her eyes.

Mistress Celeste, slid from beneath him, got up threw on her clothes and grabbed her bag. "You have some work on your hands with this one, if you decide to keep him." And with that, she walked out the door, closing it behind her.

Mistress Nora stood for a moment, as Ryan gazed over her body, trying not to get caught. He wanted to reach out and touch her skin, lick and nibble those delicious breasts and slide between those beautiful legs...As she turned her attention away from the door back to his face, he quickly looked straight ahead as she was still holding his head up with the chain.

"My pet," she started sternly, "you have embarrassed and disappointed me. I do not think that you are suited to be submissive to me. Like most men, you simply want to lead a woman around rather than follow her guidance. I will not waste my time with you."

He started to protest but realized that would be against the rules. So he stopped himself and glanced downward as she looked at him. What was he going to do now? Part of him wanted to give up, throw her down and have his way with her, at least he'd get that. But the other part knew if he did, he would never see or hear from her again. And he didn't even know who she was or what she looked like so that would be that. His mind was darting as he tried to figure out what he should do.

She let go of the chain, walked to the chair she had been sitting in, pulled on her clothes and started for the door. He began to feel panicked as he knelt there still naked, covered in cum with the dildo held firmly in his ass....

"Please, Mistress, I can do better...I will do better. Please, please do not give up on me. I want only to please you. I will do anything...anything you ask. I swear it."

She did not turn, as she opened the door, but said, "No, we are done here."

"Then please Mistress, I must still be punished for embarrassing you. I must be punished. Please Mistress" He pleaded as he stared at the floor.

She smiled, but quickly extinguished her approval, as she closed the door and turned toward him. He was still looking at the bed.

"Get down on the floor on all fours," she instructed him.

With his eyes still cast down, he quickly climbed to the floor on all fours. She sat down on the bed and he could hear her digging through her bag. She had not made him put the blindfold back on and he could see her shapely legs so close to his face, he could smell her soft, musky perfume. Oh, what he wouldn't give to work his way up those legs, licking and kissing along the way.

"Is my naughty little pet getting horny again," she asked as she saw his member coming to life again.

"Yes, Mistress, " he quietly replied.

"Is it the penis sized dildo in your ass...perhaps you want a man instead of a woman?"

"No, Mistress," he said empatically.

"We shall see," she responded blithely.

SMACK -- the paddle came down hard on his ass cheeks. The shock and force had nearly knocked him over.

"You will receive 20 licks for your insubordination, unless you think that is unfair. Do you think that is unfair?" She asked.

"No Mistress, whatever you say is fair." He replied.

"Good boy."

SMACK, SMACK, SMACK, SMACK --each one came harder than the last. It felt as though he was on fire. He was already breathing hard and breaking out in a sweat trying to hold still and make no noise. She stood and threw her leg over his back. She placed her weight down on his back and he could feel that she had no panties on. She was warm and wet and he knew she was getting as turned on spanking him as he was being spanked.

SMACK, SMACK, SMACK --he was hardly concerned with the stings as he could not stop thinking about her soft bush and pussy lips on his back as she rocked back and forth with the effort of each swat. And still he held the dildo in its place, not wanting to disappoint her again. Yet, before he knew it, she was done. She stood up, placed he paddle back in the bag and headed for the door.

"Perhaps you will hear from me; perhaps not." And with that, she was gone.

To be continued?