tagBDSMOld Friends

Old Friends


As his webcam image came to life, a wide grin spread across her face. She couldn't believe she was looking at Ryan. After 29 years, she was looking at the cutie she'd had such a crush on in junior high. Now she was glad she had decided not to put up her picture or let him see her on webcam.

"Nice", she messaged, "now take off all your clothes so I can see if you are worthy of my time."

She'd always wanted to try the Dom role but had been nervous to do so, but now as she looked at those sexy blue eyes, sandy brown hair and, as he panned down past those six pack abs to his long, hard cock, she was excited she had made this move.

She texted, "You will meet me tomorrow at the Days Inn on Bevans Road at 6 p.m. Go to the front desk and ask for the package for Ryan." She did not wait for a response and simply logged off.

The next day, Ryan walked to the desk at Days Inn and asked for his package, as he nervously looked around. The clerk handed him a small box and a room key. On the top of the box read: Go to room and open box; further instructions inside.

Ryan went quickly to the room and opened the box. Inside was a blindfold and collar with a short chain attached to it. He unfolded the paper inside: Remove all your clothes, put on the blindfold (securely so you cannot see anything-if not, you will not hear from me again) and the collar. Get down on all fours facing the door and wait quietly.

Quickly undressing and attaching the collar and securing the blindfold, being sure he could not see the smallest light around the edges. As he lowered himself to the floor, to position, his mind was a whirl of curiosity, excitement and uncertainty. "Am I sure I want to submit to some woman I don't know", he thought to himself. But as he began thinking about all they had talked about this past month online, he grew harder, thinking about it and the prospect of bedding this hot and vivacious woman.

It seemed as though the minutes were dragging by, as he waited. Was she coming? Perhaps this was just some stupid joke. Should he get up and leave...no, she had told him to wait quietly but his hard on was beginning to strain on his control to stay on his hands and knees. Then he heard the door open, someone step in and the door close. No words were spoken as he heard someone set something near him on the floor.

"Nora, is that you", he asked in a low voice.

WHACK...he felt a firm slap on his ass. Though it didn't entirely hurt, it did sting. "Did I say you could speak, my pet?" She asked sharply.

"No," he whispered. WHACK, another sharper slap as she pulled his head back, using the chain on his collar. "No, what?"

"No Mistress." He felt the chain loosen as she leaned forward. As she put her mouth to his hear, he could the material of her shirt over her breasts brushing along his back. "That's better, my pet. You will learn your place or you will be punished", she purred into his ear, her hot breath traveling along his hear and down his neck, making his spine tingle.

She walked into the bathroom and closed the door, moments later he heard the door open and felt her sit on the bed next to him.

"Now, let's see what I have to work with," she said.

First, she walked to the front of him, pulling the chain on his collar, until he was facing up toward her. Shoving her fingers in his mouth, she opened it, examining his teeth and tongue, probing with her fingers like a buyer purchasing a stallion. Next he felt her hands gliding down his back as she walked to his backside. As she stood squarely behind him she put her hands on his ass cheeks, spreading them for inspection. He could feel her fingernails trailing down until she reached his puckered, tight asshole, where she stopped to place two fingers firmly against it and rub in circular motions for a moment. He could feel himself growing harder...not even aware that his cock could feel so strained against its own skin. He let out a low moan.

WHACK, harder this time across his ass. "Did I say you could enjoy my inspection?"

"No Mistress, I'm sorry"

"Very well, then. Hmmm, seems someone has had something naughty on his mind. I see your cock is hard and moist on its tip." She observed as she gently grabbed the base and slid her hand to the tip, stopping only for a second to rub the precum gently around the taut tip. "Well, I think you'll do. Shall we begin your training, my pet?"

"Yes, please, Mistress."

"Wonderful, I see your manners are already improving. Do you remember our agreement and the rules laid out before you came here to me?" She asked.

"Yes, Mistress."

"And you agree to abide by all of them without question?"

Again, "Yes, Mistress" he said firmly as she sat on the bed next to him and began rummaging in the bag she had set next to him.

He felt something warm and wet being dripped onto his ass cheeks, its warmth felt good. Her hand came down to his bottom and began rubbing and massaging the oil on its cheeks with firm, soft circular motions. It felt so good and he desperately wanted to let out a moan but stopped himself for fear he'd be punished again.

"Does that feel good", she murmured in a soft, seductive tone.

"Yes, Mistress, it does."

With that, she squirted some cold gel on the pucker of his asshole. He almost jumped forward but held himself in place. It began to warm though as she began rubbing it around his asshole with what felt like a rounded object. As she applied more and more pressure on his virgin hole, he began to feel fear in the pit of his stomach. "Why was she pushing so hard...was she really serious about de-virginizing his asshole as she'd said online", he wondered silently. And as she gently slid the rounded tip into the entrance of his ass, his fears were confirmed. He wanted to say something, to ask how far she was going to stick it in him but knew that each smack of his ass would only get stronger and stronger if he did.

He felt kind of numb in his ass and as she slid the tip in and out, pouring a few drops of massage oil down his crevice into her intercourse with his hole. "This isn't so bad," he thought. It actually felt pretty damn good. But even as he was thinking that, she slipped it in further and he realized as it went down it got a bit larger. It still felt so good, he didn't worry as much as he was in the beginning.

As she pumped the tip of the prostate stimulator in and out of his ass, she continued to rub his cheeks with her other hand, relaxing and making him hornier all at the same time. "Are you relaxed, my pet," she queried.

"Yes and no mistress"


"I feel relaxed but am so horny, it's hard to know if I am relaxed or not."

"Very well, then, my pet" and with that she swiftly slid the prostate stimulator fully into his asshole.

Damn, his mind yelled, that only made matters worse. Though it had hurt going fully in, he also felt part of it against the area between his balls and asshole, giving him a quick rush of pure pleasure into his groin area.

"Now up on your knees, pet, and be certain you don't allow what I have placed in your ass to fall out or you will be punished." She quipped.

"Yes Mistress", he gasped as he rose slowly to his knees. Surely this had to be it. She was going to remove the mask to he could see her.

"Now turn and face the bed, where I am sitting and place your hands on either side of me on the bed ," she commanded.

He did as he was told and placed his hands on the bed. As he kneeled there, he could feel the bed shift, as she carefully lifted one leg up and placed her feet on the outside of each of his hands, scooting toward him. He could smell her musky pussy and his mind began to swim, a bit, but he caught himself as he was still making sure the item placed in his ass would not come out. It seemed as though all his senses were betraying him and refusing to work together.

"Now, you will lick and suck my pussy and my clit. But mind that you use your mouth and tongue only. You are not yet permitted to touch me," she instructed. And with that simple instruction he began bowing his head slowly to her waiting pussy, as he wasn't sure exactly how far he had to go. He felt her hand on the back of his head as she pushed his face into her wet bush and he began shoving his tongue into her soft mound, licking and sucking whatever his mouth could reach.

"Mmmm, that's a good pet," she murmured, "but don't ever make me wait once I give you an instruction again."

As Ryan shoved at her hot, wet pussy, licking and sucking greedily, she moaned and humped at his face. God, how he wanted to grab her by the ass and shove his face deeper and deeper into her, tongue fucking her. But he had his strict instructions and abided by them, in hopes that he would please her soon and be able to plunge his hardened and straining cock into that hot, wet pussy. It was that thought that kept him going with fervor until she yelled out and orgasmed all over his face.

As his face lay in her soaking muff, she petted and stroked his head, murmuring that he was such a good boy.

As he felt her move on the bed, he thought, surely now he would get his real reward. He heard the bathroom door shut then open a moment later. He heard her pick up the bag and walk toward the door. As she reached the door, she turned and said, "Do not remove the mask, collar or the stimulator in your ass yet. You will masturbate and once you cum, you can remove them, take a shower and dress. Take the items home with you in the box and be sure they are properly cleaned and stored. Decide if you are ready and worthy to be my pet. If you are, come back tomorrow, with your items and there will be another box at the desk for you."

He sat there stunned and said nothing.

"Have you nothing to say, my pet?" she asked.

"Yes, Mistress. Thank you."

"No need to thank me. As long as you are a good boy, you will earn more rewards as we go." With that, she closed the door behind her. Ryan could wait no longer and began pumping his cock with both hands, attempting to quench the fire she had lit and left.

To be continued?

Report Story

bydancingqueen369© 2 comments/ 11559 views/ 7 favorites

Share the love

Tags For This Story

Report a Bug

1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartFloFlip, soccersoccer1964 and 5 other people favorited this story! 

by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

There are no recent comments (2 older comments) - Click here to add a comment to this story or Show more comments or Read All User Comments (2)

Add a

Post a public comment on this submission.

Post comment as (click to select):

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: