Jackie and Carl's first meeting

They were to meet in the hotel bar. He would wear a silk hankerchief in his jacket pocket, to be recognizable.

Jackie found the hotel and as she entered the lobby she felt all flushed, was she really crazy to meet an almost total stranger. Did she dare start thinking about where the evening may go? She took a deep breath, knowing that the thought of the adventure was just too powerful to ignore. An interesting mix of apprehension and desire. She thought that he seemed like a civilized soul who had some deeper desires like her own. Maybe he would unleash the abandonment she had wanted for so long. A past lover had trifled in the spanking area, but she wasn't sure if this too was his deep desire or if he was just trying to please her, feeling a bit awkward by the experiences. Carl had a website that clearly showed not only his interest but his ability to follow through. She saw the hotel bar. Her knees felt weak and her legs felt shaky. She quickly put on some lipstick and realized that her stockings, garters and silk panties made her feel very sexy and there was wetness between her legs. Would he see the desire and nervousness in her face, would her lips tremble when she said hello. Feeling like a schoolgirl on her first date, she laughed and said to herself relax and have fun. Regaining her composure, she confidently walked into the bar.

There were a few people seated at the bar and at the tables. She saw him and he smiled back at her. He stood and watched her advance. He thought as she advanced that she was in good shape and wore nice clothes that showed off her legs. Sexy, yes she was sexy.

Her thoughts darted to a girlish self-consciousness (this was not her usual mind-set) Was she going to babble like a fool or be quiet and just take him in. Images of the shoehorn and hairbrush danced through her mind. He had a natural charm and greeted her with a warm handshake and a gentle peck on the cheek. He smelt wonderful. She relaxed and they exchanged pleasantries about their respective travels and Toronto. The waiter approached and she ordered a glass of white wine.

Carl ordered a gin and tonic and sat down at the table opposite Jackie. He'd appreciated what he'd seen of her so far. Nicely dressed, nicely shaped, pleasant voice, exhilarating perfume - and that delightful roundish bottom - just perfect for spanking he thought. He gradually turned the conversation around to what both knew to be the object of this assignation. He could sense that she liked him and was pretty sure that at least he would get to give her a long and very sensual spanking - indeed he could feel himself stirring below the waist at the thought.

He looked deep into her eyes and held her hand over the table.

"Well Jackie, are you going to let me spank you tonight?"

Jackie was a little taken back by the directness of the question, but she too was feeling aroused and she also knew deep down that she had come to the meeting hoping it was going to progress that far at least unless she felt uncomfortable with Carl, or if he was downright repulsive and she didn't, and he was not.

" You don't hang around do you?" she said.

"Well its not often I get to be with such an attractive and intelligent lady" he replied "and I hate to waste good spanking time - and I have got a bottle of wine in my room so we can continue our discussion in more private surroundings"

"Flattery will get you everywhere" replied Jackie - "Even up to your room" She smiled and looked him in the eyes. He smiled back.

"Can I borrow your key - I'd like to freshen up a little before we perhaps take the next step"

"Even better - I have a spare" He passed her a room key - or rather a credit card shaped piece of plastic which would open the door. "It's room 17-124. How much time do you need?"

Jackie was pleased he'd just let her go to his room without him and appreciated that she might have a few minutes alone. "10-15 minutes" she said.

"I probably should tell you to wait for me with your panties and hose off, your skirt up exposing your bare bottom, and standing in the corner" he said with a wicked smile on his face, but instead, open a bottle of wine and have a sip while you're waiting for me. I'll be up in about a quarter of an hour - excuse me if I don't stand up when you go - I need to recover my composure" He said this with a downward glance to his lap and with a wry smile on his face.

Jackie grinned, stood up and left the bar heading for the elevators. Found the ones which went to the 17th floor and walked down the long corridor to his room. She opened the door to a fairly small, but nicely equipped room. Well it was one of Toronto's grand old hotels. She noticed that there were two bottles of wine on top of an in-room refrigerator/minibar. One red and a bottle of white sitting in an ice-filled ice bucket.

First things first she thought, and headed to the bathroom with her make-up purse. A quick clean-up here, a dab of perfume there, a touch-up of her make-up and a tidy of her hair, although she thought that was going to be a real waste of time. She smiled to herself. She checked herself out in the mirror. 'Not bad' she thought.

She took about ten minutes in the bathroom and then decided to open the wine - but which? was this a test? He looks like a red wine drinker she thought so decided to leave the white. She looked at the bottle of red. It was a Spanish wine - a Rioja - and not one she was familiar with. She fond the corkscrew lying next to the bottle and expertly removed the foil and then the cork and poured a little into a glass. She sniffed and approved the vanilla, oaky nose and swilled the wine around in the glass. It was quite viscous. She took a sip. Really pleasant and quite heady. She settled into an armchair to await Carl's arrival.

By the time she heard his keycard in the door she had just about finished the glass and was ready for another. Carl came in and saw she had opened the red. "I'm glad you chose the red" he said. "Actually I like both white and red - but I sort of felt like red this evening. Maybe I can get your bottom to match it" he said grinning widely.

Jackie looked at the wine remaining in her glass noticing how deep a colour the wine was - she wasn't sure she'd want her bottom to match that!

He walked across the room, picked up the bottle and refilled her glass and poured one for himself. Clinked glasses with her "Here's to an enjoyable evening" he said.

"Amen to that" said Jackie, feeling a little nervous again despite the two glasses of wine she'd had and the third one beginning to go down very easily.

Carl went across the room and opened his suitcase which was on a stand inside a walk-in wardrobe and re-appeared holding a canvas shoe, a wooden hairbrush and a longer wooden object which turned out to be a long handled bamboo shoehorn. Jackie's bottom twitched involuntarily when she saw these. If he spanked her really hard with any of these she'd be in for a very uncomfortable taxi ride back to her hotel - and she only had his word for the fact that he didn't spank too hard. Could she trust him? She was now in a situation where she didn't really think she could turn back - indeed she didn't want to turn back, but the doubts persisted.

Carl sat on the bed. "OK Jackie. Over here. The moment of truth is about to arrive." He said this with a broad grin. Jackie put down her drink, stood up and walked over nervously to his side.

Carl knew how nervous she was. "Don't worry" he said, "I'll start off gently and build it up. If you think its getting too much, tell me. I won't promise to stop right there and then, but it'll give me an indicator of what you can take. Now, over my knee."

Jackie lowered herself over Carl's knee. She immediately felt his arousal and smiled to herself. "Well, here goes" she thought wondering what was now going to befall her.

Carl started spanking her with his hand over her dress - not particularly hard, but enough to feel it. After about ten spanks, he paused and pulled her skirt up. Jackie was wearin lacy panties, stockings and a garter belt. He looked at her bottom appreciatively and continued spanking - now a little harder. He pulled her panties up so her cheeks were exposed and rubbed the already pinkening bottom, slowly moving his fingers down to her pussy, stroking it gently, and then moving his fingers inside her panties until they found her exceedingly wet pussy again, massaging her clitoris until she almost came.

"I think we're going to have to remove these completely" he said, undoing the garter clips to the top of the stockings and then pulling down her panties and taking them right off. He then pushed her legs wide apart and returned to massaging her clitoris until Jackie came with a hugely responsive orgasm.

"I think the lady likes this type of treatment?" said Carl. Jackie blurted out an agreement as his fingers continued their massage. He stopped.

"Which implement would you like to try first?" he said. "It doesn't matter really as I'm going to use them all on you, but at least you can't say I didn't give you a choice".

Although Jackie wasn't exactly in a position to see it she could sense the smile on his face as he said that.

"I have a hairbrush, a karate shoe, a bamboo shoehorn and a belt. All of them give a different sensation, but all can hurt a lot" he warned.

"I'll try the shoe, sir" said Jackie as this perhaps sounded the most innocuous of the implements offered, with the 'sir' added just in case it gained her any brownie points.

"I'm afraid the shoe isn't as tame as it looks" said Carl and then proceeded to give Jackie ten spanks with it on her bare bottom allowing several seconds between each spank and covering a different area of her nice round bottom with each spank. The shoe did hurt. By the end of the ten, Jackie was squirming around over Carl's knee, but didn't want to give in so early. "Wow, that shoe really hurts" she said through gritted teeth. Carl started to rub her very warm to the touch bottom to give it some relief. "Only another ten with it to come" he said. "I'm going to give you twenty with each of these toys, in groups of ten. The idea is you get ten painful spanks - and then lots of massage until you come - or at least get close to coming soyou get pain followed by pleasure right through." So saying he brought his fingers down between her legs again, finding their mark quickly. Despite the continuing soreness in her bottom, Jacke found herself exceptionally aroused and came again quickly. The thought of the pain/pleasure mix stimulating her.

Carl eased off the massage and rubbed her bottom some more, before continuing the spanking. The shoe on the already sore bottom was almost more than Jackie could take, but she also realised that he wasn't spanking her quite so hard at the end. After the ten spanks, she parted her legs in hope that Carl would quickly find her pleasure zones, but instead he told her to stand up.

"For the rest of this spanking you are going to be totally naked" he said and he started to undress her, slipping her dress of her, unclasping her bra and letting her breasts fall free. He admired them, playing with and then kissing and biting gently her nipples which sent more fire coursing through her loins. He knelt down in front of her and rolled down her stackings tenderly and butied his face in her pussy giving it a kiss. He stood up again in front of her and reached down and started massaging her pussy, pressing his body against her and giving her a passionate kiss at the same time. He guided her hand down to play with his cock through his trousers. It was very hard.

She started to try and undo his belt, but he stopped her. "After the next spanking" he said. He pushed her onto the bed, now playing with her breasts as well as her pussy until she arched her back as she came again - in fact she seemed to be coming for an age. She slumped back on the bed looking up into his twinkling blue eyes.

"There's only so much pleasure a girl can take" she said smiling.

"And you're nowhere near that yet" he replied.

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Jackie relaxed lying flat on her ack on the bed. Carl massaged her all over, and then pushed her legs wide apart. "You're now about to enjoy the most sensual type of spanking of all" he said, rubbing her pussy until it swelled and moistened again. He picked up the shoehorn. "This implement could have been designed specially for spanking pussies" he said with a wuicked grin.

Jackie involuntarily moved her legs together.

"I advise you to keep your legs well apart" said Carl. "Pussy spankings should be reasonably gentle as they can be painful, even though very arousing. They are given to those who play with their own pussy a lot - as you admitted to doing. However if you bring your legs together before I've finished, I not only start again, but spank much harder - so be warned."

Carl pushed Jackie's legs wide apart again, and brought the convex end of the shoehorn down on her pussy - not very hard, but even so an exquisite pain rushed right through her. She'd never felt a sensation quite like it. He spanked her again - a little harder, and again the pain shot through her from her knees to her nipples. He then gently rubbed her pussy better bringing her close to orgasm. lightly spanking the inside of her thighs as he did this. "The really nice thing about pussy spankings is that it gets kissed better afterwards" The very thought almost made Jackie come again.

This time he carefully parted her pussy lips with his fingers so the clitoris was exposed and gave her two light spanks directly on the clitoris - that most tender part of the female anatomy. Jackie almost clamped her legs together as a natural reaction to this, but luckily remembered his warning in time and pushed them apart again. Although this pussy spanking was painful, it was one of the most sexually exciting experiences she'd ever had and she wanted him to continue. Indeed she thought maybe that a couple more spanks there would alone push her over the edge to orgasm. Well almost - two spanks later plus a very light touching with his fingers on what was now an excessively sensitive area made her climax again - and she took a long time to come down from this one. He squeezed her erect nipples which sent another fire down to her pussy. She spread her legs even wider begging for the spanking to continue.. He obliged with four more fairly gentle spanks, and then the ritual rubbing better - and then put his head down between her legs, kissing her pussy and tonguing it until she came again over and over. Even her labia felt as sensitive as her clitoris after the pussy spanking.

As she lay gasping on the bed after what must have been her sixth orgasm - although it felt like ten, Carl at last removed his shirt, trousers and underpants, his cock standing up firmly. He took Jackie's right hand and cupped it round his balls and sighed deeply as she fondled them and then his penis. She sat up and moved to the edge of the bed pulling him gently towards her, taking his penis in her mouth, licking it and caressing his balls and sliding her mouth up and down. He tasted so good. He held her head against him and she felt him shuddering a little, but then he gently pulled her head away. "I don't want to come quite yet" he said - and then with a grin "You don't think you're going to use sex to get away with the rest of your spanking I hope".

Jackie shook her head.

"Well next you're going to feel the effect of the shoehorn on your bottom" he said.

" I think I might prefer more on the pussy" said Jackie greedily.

"Maybe later. Now kneel on the bed with your legs apart - just in case I need to give the puss a gentle reminder. But you've got ten coming on your bottom"

He then gave her ten sharp spanks with the shoehorn on her bottom, lots of time between each spank and wow, it stung like crazy, but somehow was easier to take than the shoe before it. When he finished he rubbed the shoehorn up and down her exposed pussy before giving her another two spanks on it from behind. Jackie nearly hit the roof, but came down fast rolling over on to her back with her legs apart. God, she wanted him to fuck her there and then she was so aroused. He obliged by massaging her puss again until she was dying to come. She saw him ease on a condom, and then he was between her legs thrusting in deeply. She came again immediately, but he carried on, building her up to yet another climax and this time she saw him grimace like he was in agony as he came with her.

He collapsed in a heap beside her, hugging and kissing her, massaging her all over her body, kissing her nipples, biting them gently. Then after several minutes he sat up.

"The evening is young - and I take longer to recuperate than you" he smiled as he said that. "How about showering, making ourselves a little more respectable and going down and having some dinner. I think I need sustenance.

Well suffice it say that showering together Carl made Jackie come once again - wow the girl was insatiable and they slipped on clothes ready to go down to the restauraunt. "No panties" carl insisted as Jackie started to pull them on. I might want a quick feel during the meal. Then I can get you to play Sally from 'When Harry met Sally' for real. He grinned wickedly.