He Asked...She Delivered

Story Info
When fantasy becomes reality...painfully.
1.7k words
4.37
31.3k
7
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Yabizness
Yabizness
11 Followers

He had been chatting to Sylvia for a little while having met on an on line dating site. He had always had an interest in receiving a spanking from a woman and when she had offered to make his fantasies come true it hadn't taken much before he decided to take up "the challenge" as she had called it. It had seemed ages away when the date, three weeks in advance, had been set, but tonight was the night and a strange mix of excitement and nervousness consumed him.

For her part, she had never actually been a Domme. When he had first gently raised the subject, however, she realised just how much the thought excited her of giving a man a real spanking, not just a playful slap, but really to make it count.

A big part in why they had first got on so well was that Sylvia had mentioned how much she preferred stockings and suspenders to hold ups, and that frankly she couldn't stand tights. She had been surprised by just how much stockings turned him on and permitted herself a wry smile as she straightened the seams and attached her stockings to the black suspender belt she had selected carefully knowing just what it would do to him. "Well Paul, at least you'll be pleased by what you see, even if I do ignore your pleas for mercy."

For the past few weeks Sylvia had been busy and after an intensive period of research and on line shopping now had everything she thought she needed for a truly memorable evening. "You should be careful what you wish for" she thought contemplating his request to her to spank him.

Paul walked up the drive towards Sylvia's house, drew a deep breath and rang the doorbell. This was not only the night he was to receive the requested spanking but also the first time he was to meet Sylvia. The door opened and she was wearing a tight dress, thin enough to accentuate her curves but also for him to see the outline of the suspender straps, his arousal was instant. She picked up his hand, pulled him towards and kissed him full on the lips before pulling him gently inside. "I'm so glad you came" she said smiling, noticing the bulge in his trousers, "I thought you might chicken out. Are you sure you still want to go through with it?"

"I've never been so sure of anything in my life" he replied with a confidence he didn't feel "you look simply stunning."

"Flattery will get you everything except mercy...now strip!"

Things were moving quicker than Paul had expected but such was his state of combined arousal and nervousness that he did as he was told.

"Fold your clothes neatly and put them in the cupboard there, you won't be needing them for a little while, then follow me."

Sylvia started to move upstairs, her arse swaying seductively with each step as Paul followed closely behind. She stopped at a closed door, turned to him and held him close. Smiling as she felt his hard on push against her she said gently "last chance to back out, we can go downstairs, have a drink and a chat or we go through this door. Be warned, though, through this door fantasy becomes reality...are you sure you want it?" She reached down, took his cock in her hand "I guess this is the answer, shall we go through?" Paul nodded and she opened the door

In their on line discussions their cyber sessions had always started with a hand spanking and tonight was to be no different. In the middle of the room stood a large bed with a wrought iron frame. An oak wardrobe was against one wall and a full length mirror against the wall at the foot of the bed. She sat down and pulled up her dress to reveal the stocking tops, the black suspender belt and semi transparent lacy knickers. Paul's cock twitched as if to announce impossible levels of arousal. "Glad you like it now get over my lap. I want your bum high up, move forward a little and put your hands on the floor" Paul did as he was told and she gripped his cock firmly between her thighs.

Sylvia was loving this, she'd read more than a few stories on the internet and had decided exactly how tonight was going to play out, the start would be tame but the intensity would soon increase...SLAP, SLAP one for each buttock "How was that, ok, shall I carry on?"

"That's fine, yes please"

Sylvia started again and soon got into a rhythm, Paul was now starting to feel some discomfort.

Suddenly she stopped. "On your knees" she commanded "you are getting heavy on my lap and my hands are getting sore. We haven't finished yet though. She unzipped her dress and it fell away to reveal a bra to match the seamed stockings, suspender belt and knickers. "Wow, I've seen picture of course, but nothing matches reality" said Paul

"You will recognise the significance of those words later, now on the bed and lie on your front. The pillows in the middle are to keep your bum raised. I'm going to tie you up now, it really turns me on the thought of you at my mercy. I can see it turns you on too" she smiled and squeezed his balls just a little harder than was comfortable. Paul did as he was told and Sylvia used silk scarves to spread-eagle him to the bed frame...there was no escape now. She went over to the wardrobe and opened the door - Paul looked over and gasped. Hanging on the inside was a paddle a tawse and a cane..."I thought you didn't have anything like that"

"I didn't but when you asked me to spank you I thought I had better do something about it. You are going to get thirty strokes from each but don't worry you'll get a few breaks on the way."

She lifted the paddle from its place and said "10 on the left followed by 10 on the right cheek and then 10 in the middle...once I start we go through to completion, ready?"

She didn't give him the opportunity to respond and brought the first down with a resounding slap..."Ouch, ouch"

Paul felt his arse was on fire, the pain was more than he'd expected but he recognised the futility of his position, and it wasn't unbearable

When all 30 were complete Sylvia hung up the paddle and turned back to Paul. This is really making me wet, I wish we'd got together earlier, your arse is looking very red. Poor you" she giggled.

"Now the tawse, this is really going to hurt, so we'll break it into two lots of 15. 10 seconds between strokes and three minutes in between to get your breath back. The first 15 will be at medium strength, the final 15 harder."

"I don't suppose there's any point in asking for mercy" said Paul. Sylvia snorted "Mercy? You're getting it, I could do all 30 at full strength at 5 seconds intervals. " She raised her arm.

Paul had never experienced anything like it, if he could have pushed through the bed and out the other side to escape he would happily have done so. The strange thing though was that he still had a raging hard on, something that hadn't escaped Sylvia's attention as she gently flicked the tawse at his exposed balls...."no maybe that's for another time" she thought wondering about whether CBT would thrill her in the same way. Her arm rose again "2, 3, 4 stop whinging, 5, poor baby....."

At last the 15 were over and Paul relaxed, his arse was truly on fire now. Sylvia sat on the bed next to his head and gently stroked his hair "just another minute and we'll start again, and then there's only the cane to come...."

"Ready... 1 (ouch) 2, (fuck me) 3, ouch, 4, (please stop)...5 ..." Sylvia ignored him and carried on

She put the tawse away and picked up the cane. "This is a senior cane, it will really hurt, more so even than the tawse and then you're through. This time I'm going to do all 30 in one go. The first 10 will actually be relatively gentle, the middle 10 will be harder but the final 30 will be as hard as I can do them. I want you to have a souvenir of this evening for a little while!"

Paul buried his head in the bed, he was still puzzled by the conflicting emotions running through his head, his cock told one story, a raging hard on betrayed the sexual excitement, his arse another and he doubted he would be sitting comfortably for days and his head wondered why the fuck he'd let himself get into this position.

The cane whistled through the air and the first stroke landed...true to her word it was genuinely gentle and Paul thought he'd cope...."10" said Sylvia, "now they get harder." There was more of a whoosh this time and the cane landed with a real burning sensation, the second followed then the third and on until after the tenth a small break. Sylvia reached under his body and gently caressed his still erect cock..."well you're enjoying it at least...and so am I, I am so wet. Just the last ten to go, but these are going to be as hard as I can manage...try not to scream, I don't want to disturb the neighbours" she laughed.

This time the cane seemed to sound like a jet engine about to take off and the pain was immense..."1, only 9 to go..."

By 4 Paul felt he could take no more, by 7 he thought he was going to die and by 9 he would have done anything to escape.

After the ninth she paused..."last one, I'm really going to put everything into this one."

She lifted the cane high up towards the ceiling and brought it down like a golfer trying to hit a hole in one on a par 5 laughing while doing so..."all over now, relax..."

Quickly she untied him, rolled him over onto his back and reached for his cock, "and now for your reward...but you really should be careful what you ask for in future..."

Yabizness
Yabizness
11 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
3 Comments
AnonymousAnonymousabout 2 years ago

I emailed this story to my mistress. I requested a spanking like this many times but she never delivered. To be honest, I usually found an excuse to postpone doing it. She had a close friend who she shared my fantasy with and contacted me saying together they would make it happen.

Just as Sylvia did in her story, my mistress and her friend made me strip, fold my clothes and leave them at the door. Before entering the playroom, they turned and asked if I wanted to go through with the spanking they planned. I was so nervous but my raging hard on showed I was more than ready. They began over the knee with a hand spanking of 10 on each cheek from both of them. After 40, my ass was a pinkish red. I commented and said “is that all you’ve got”. Huge mistake.

Tied face down they brought out a belt, small wooden hairbrush, a kitchen wooden thick but thin spatula and two canes. Again they said 10 on each cheek, nonstop. I was asking for mercy after the hairbrush. They just laughed. The wooden spatula brought bruises and my scream were quickly hushed with yesterday’s panties stuffed in my mouth. The canes brought tears and whimpering. In all, they gave me a total of 240. My ass is still recovering. She has emailed me a few times asking when I will be back. Will I?

AnonymousAnonymousover 5 years ago
No more?

Teasingly arousing. Too bad you never got around to telling us what happened afterward!

AnonymousAnonymousover 8 years ago
Mercy?

Paul stood up after 5 with the paddle and decked her with a right cross to her chin. She was down and out for the count. When she woke up he was gone and she never heard from him again.

Share this Story

story TAGS

Similar Stories

Her Presents She had a number of surprises for him.in Fetish
A New Dynamic A couple experiment with a new dynamic.in BDSM
Keyholder's First Week He sends her his keys not knowing it would change everything.in BDSM
David and Kaitlyn: Chastity David is locked in chastity by Kaitlyn.in BDSM
Pegged for Love Straight guy is pegged by the girl of his dreams.in Fetish
More Stories