A Pleasant Surprise

Story Real-Life M/F C Hand
Cane
Riding Crop
A fourty-something female office manager is taken to task over taking time off to book a holiday and neglecting to inform a colleague that their scheduled meeting was cancelled. He, jokingly, suggests that she was behaving like a naughty child and needed a good spanking for messing up his day which she dared him to do. He called at her home that evening and...

One of my joke stock phrases is “you need a good whipping for that” when I comment on mistakes made by fellow female workers and this day started out as usual as any other.

It was Tuesday lunch time when I went to see Mrs Jones to discuss the usual weekly topics on production schedules, staff attendance and other mundane business items. Mrs. Jacqueline Jones, to give her full name, is a quite attractive lady in her mid forties (I give her about 44 – 47), divorced, with no children at home. She keeps her figure well being 5’ 5” tall and a genuine 36C-28-36 body shape. At work she wears a two piece suit, usually in dark blue or black, and socially dresses and skirts as the mood takes her – I have only seen her in trousers or jeans twice but then that’s not unusual as we generally meet at work.

Jackie was late for our meeting and when she arrived she was very agitated. I asked her what was wrong and she said “No time now – I’ll tell you later. Can we meet after work and we’ll run over things – won’t keep you long.”

“No problem Jackie – see you at four-thirty is that Ok?”

“Yes that’s Ok Steve – see you then.”

I went back to Jackie’s office but she wasn’t there instead there was a note addressed to me on her desk propped up on the telephone. It read --- “Sorry I couldn’t make it had to rush. I know this is going to make it difficult for you to write the report but you can call me if you like.”

I was feeling a bit pissed of by now having to find other things to do when I would have been writing the weekly report but as it’s usually almost identical each week with only a few minor alterations and I knew what was going in it anyway one could say that the report was done anyway – but she didn’t know that!

Driving home I thought I’d give her a call and used the phone in my car to call her. When she answered she apologised profusely for rushing off and asked if I wanted to call round so she could say sorry personally and have a coffee or something. Not knowing where she lived I asked her and to my surprise I was only about ten minutes away.

I came off the by-pass and turned into a tree lined road – County Gate – she said I would find a small cul-de-sac on the right called Gate Close and her house was at the far end on the left. It took me about fifteen minutes to find number seven and I drove into the semi circular driveway and parked by the garage entrance.

I walked back to the front door and started to look for a bell push but as I was about to press it the door opened and Jackie invited me in. She was still in her office gear, so to say, (Dark Blue straight skirt, cream blouse, cream bra (and matching pants I presumed), tights and high heeled shoes.

“So sorry Steve but I had so much to do I just had to get away and sort out my holiday booking!”

“Eh!” I replied, “Your holiday booking couldn’t wait until four o’clock?”

“Yes! I know now it sounds so pathetic but they wanted to change the flight times but I didn’t want to land in the middle of the night – you know what it’s like, no taxis, dark, usually the hotel desk is shut or the people are half asleep!”

“Good God! Jackie you need a good spanking for messing me up like that over something so trivial!”

“Ha Ha and you would like to do it Eh?”

“Maybe, maybe? Come here and bend over.”

To my surprise she came over to me, turned around and lent forward mockingly sticking her backside out as if bending over. Automatically and without thinking I slapped her right buttock cheek – SLAPPPP!

“Ouch!” She jumped up, “That stung Steve – you know I wasn’t expecting that I was bluffing but you spanked me!”

“You mean you really didn’t expect me to spank you?”

“No – well not really, maybe a playful tap.” Rubbing her right cheek she continued, “I can still feel your hand – I bet I’ve got a red mark there now – I’ll have to look in a minute—I’ll just get the coffee.”

Gently rubbing her bottom she went to the kitchen and looked back at me as she went through the door still rubbing her bottom. I thought I didn’t hit her that hard but she definitely felt it and seemed intrigued by my slap.

When she returned with the coffee I asked her how she felt and did it hurt as much as much as she made out. She told me that her dad used to put her over his knee when she was younger but that stopped when she went to college. Once her ex-husband threatened to spank her but never did although she did admit that one of her friends playfully whacked her across the backside with a garden cane and it hurt but gave her a “tingly” feeling about half an hour afterwards.

Jackie put the TV on and set it to SKY NEWS. It was on in the background when an item was shown about disruptive kids in schools. Jackie turned to me and asked what my school was like. I told her that we were too scared to be as bad as the kids are today because the teachers could use the cane on us. I told her of one incident where 3 of us were caned across our backsides my friend and myself got 4 strokes and Brian got 6 strokes – I can’t remember what it was for now but it must have been something naughty at the time.

She told me at her school it was only the head mistress or her deputy that could cane the girls and she only ever saw three girls get the cane across the bottoms. She described the incident as being one morning at assembly when three girls were marched onto the stage in the hall and the whole school was told that they were to be punished for throwing tomatoes at passers by from the school bus. Each girl was told to face the side of the stage and to bend over and place their hands on their knees. Each in turn received six strokes of the cane across their skirt and all three ended up crying – probably from the embarrassment and pain together.

“So then Jackie,” I asked, “you have never been spanked or caned in your life except from your dad then?”

“No!”

“Would you like to try it then?”

“I don’t know about that – it might hurt.”

“Well Jackie, if it doesn’t hurt it isn’t done right – is it?”

“Suppose not Steve.”

“Well, care to try a spanking then?”

“You mean NOW!”

“Why not?”

“Don’t hurt me too much. How do you want me?”

“Go and get that chair from the table and bring it here.”

Jackie went over to the dining table and picked up a chair and brought it to where I was standing.

“Thank you”

I put the chair down and sat on it then I held Jackie’s left hand and gently pulled her over my knees.

“Comfy?” I asked.

“Don’t know about being comfortable, it’s a bit embarrassing like this.”

I put my arm across her back to steady her and gently passed my right hand over her skirt and bottom. As I did I felt a distinct ridge of a suspender button and realised she must be wearing stockings and not tights. I glanced down at the hem of her skirt and saw there was a cream slip or petticoat under the skirt. “Nice” I thought. I patted her bottom lightly and asked if she was ready for her spanking.

“Too late now isn’t it?”

Slap! “Ow! Yes!” she cried.

Slap slap slap slap slap slap slap slap slap slap slap slap slap slap slap -----

I kept the whacks coming as she squirmed about on my knees. Her legs were kicking up and eventually her skirt rode up revealing her stocking tops. She was good about it because I kept on slapping her cheeks and occasionally the backs of her legs as she kicked.

After about five minutes I stopped and helped her slide off my knees onto the carpet from where she looked up at me and said, “Gosh! That was embarrassing and sore…!” As she rubbed her bottom.

I pulled her up and she cuddled me. I could feel her shaking slightly, not crying but a nervous tremble so to say.

“What’s up Jackie?”

“I was just wondering what a real caning must be like because that stings.”

“It stings a lot more I’m afraid Jackie.”

“I bet it does too. Have you ever caned anybody Steve?”

“Well… Funny you ask that because the answer is yes, often in the past when I lived in London.”

“Who did you cane? Girlfriends, your wife?”

“Both – but not at the same time.”

“I once caned my neighbour because she asked me to – we had a similar conversation as we have had now and two weeks later one afternoon she invited me in for coffee and asked me to give her a real school caning – six of the best as she put it.”

“Really? I bet that hurt.”

“Yes it did and she cried real tears and had the marks for about a week.”

“Didn’t her husband find out or wasn’t she married?”

“No he didn’t. He was ten years older than she was and so engrossed in his work that they never went to bed at the same time so he never got to see the stripes.”

“How did you cane her? I mean was she touching her toes or bent over a chair, how did you go about it?”

“I asked her how she felt she should be caned and told her to choose a position and dress mode. She bent over a low armchair at first and I laid a couple across her skirt. As this wasn’t having any effect I lifted her skirt and gave her four more which she began to feel. I then told her to remove her skirt and tights and touch her toes. She began to argue that she had already had six strokes and it was stinging. I told her that I will decide when she had enough and to bend over – which she did and I gave her another six stinging whacks across her bottom and legs.”

“So it really hurts then?”

“You bet it does my girl. Jane couldn’t stop jumping about for fifteen minutes and she asked me to fuck her as Bob never satisfied her. That was a good fuck I can tell you and she gave me a blow job too!”

“If I gave you a blow job would you cane and fuck me Steve?”

“What?”

“If I gave you a blow job would you cane and fuck me?”

“I think you deserve a good caning for suggesting that – don’t you?”

“I suppose I do Steve – would you give me a caning, I’ve been very naughty today haven’t I?”

“I haven’t got a cane with me right now. Tell you what… I’ll go home and get a couple of canes and you get yourself ready…. I’ll be back in about an hour.”

I drove home thinking about what was going to happen later. Shall I really sting her? Will she allow me to remove her clothes? Will she strip willingly? All these and more were rushing through my head. I arrived home and promptly rushed upstairs to my ‘office’ and took a ‘dressage’ riding crop from my cupboard. Running the platted shaft through my fingers and feeling the leather pad at the end I thought how her bottom might feel if I hit her with this. Its fibreglass shaft covered neatly in platted nylon about 36” long looked a formidable weapon to chastise Ms Jones with. I then took out my favourite school type cane and it’s slightly thinner cousin. I have always felt proud of these two instruments as I made them myself from cane bought at a local craft shop. One is about 34” long by 9mm thick and the other is about 30” long by 7mm thick. Their real length is about 8” longer but I soaked the ends in boiling water and curved them as a real old-fashioned school cane would be. I sanded the whole length of each and varnished them with cellulose lacquer, sanding between each of the ten coats. Once a year I sand the varnish off the tip and stand them in a two foot high flower vase full of water to keep them supple sealing the ends again with several coats of lacquer.

Placing these on the desk I quickly stripped and had a shower. I then dressed casually but smart and put the canes and crop in my old guitar case as it is the only thing I have that is long enough and innocent enough not to arouse suspicion as to what is in it as even I realize that to carry a couple of school canes and a riding crop about is enough to embarrass even someone like me!

I arrived back at Jackie’s place some three-quarters of an hour later. When she opened the door I noticed that she had changed into a smart dress and had high heel shoes on. Her legs were encased in sheer nylon stockings or tights in a nice complementary dark tan – I was hoping they were stockings!

She welcomed me in and I noticed a slight wavering in her voice. The conversation began about work and other non essential stuff switching between holidays, pets, traffic, the news and whatever came next into her mind to take the discussion off her impending beating.

I asked her to pour me a whisky as a gentle test to see if she would take and obey an instruction because usually someone about to be caned is slightly frightened and really wants someone to take control of the situation. Jackie brought me my whisky and placed it on a small table by the settee. I sat down with my guitar case and flicked the catches open. Jackie stared at me doing this and I half expected her to ask if I was going to play a tune but she didn’t. I removed all three implements and placed then on the cushion next to me and I saw Jackie watching me.

“I don’t like the look of that riding crop Steve; you’re not going to use that on me are you?”

“Jackie, I am going to stripe your backside tonight which ever way I feel like doing it – do you understand?”

“Yes. Er should I say YES SIR?”

“Probably, now stand over there Jackie.” I told her as I pointed to a spot about six feet away. She turned and took three paces, stopped, turned back to face me.

“Is this Ok – sir?”

“Yes Ms Jones. Now I want you to gently lift the hem of your dress to your waist so I can see exactly what you have underneath as protection.”

Without batting an eyelid Jackie lifted the dress to her waist to expose a thin cream underskirt or petticoat through which I could clearly see she had suspenders and stockings and a thin pair of matching panties.

“Thank you Ms Jones, you can drop your dress back now. Go and get a dining chair and put it where you are standing and sit on it facing me.”

Again she did exactly what I had told her to do. She placed the chair where she had previously uncovered her lower body and sat on it with her hands resting on her knees.

“In view of the fact that you claim you have never been caned before I think I should gently introduce your bottom to the several instruments I have here…”

Jackie interrupted, “You’re not going to beat me with all three. I only was expecting six of the best as they call it.”

“Excuse me. I call the shots here Ms Jones. That is one stroke extra for the interruption and one extra stroke for trying to tell me how your punishment should be administered.”

“Sorry sir. Please don’t hurt me too much.”

“I am going to use this crop to start with over your dress. You will get four strokes and the extra one for trying to tell me how to do it. Now I want you to stand behind the chair and lean over the back with your hands either on the seat or holding the sides of the seat.”

Jackie got up and walked round the back of the chair and bent forward towards me placing her hands on each side of the chair seat. Her hair fell forward and I could see the straight line of the zip at the back of her dress finishing as her bottom cheeks filled the seat of her skirt. She looked straight at me and closed her eyes then opened them again and continued to look at me sitting there sipping my whisky. I placed my glass back on the table and stood up taking the long black riding crop with me as I approached the chair Jackie said, “Please don’t hit me hard, I’ve never been hit with a stick before, Please be kind… Please!”

I stroked her bottom through the dress and smoothed the material out. I patted her cheeks and she flinched as I patted. I gently pushed her feet apart with my shoe so her legs were about 6” apart. I gently ran my hand down the skirt over the backs of her legs feeling the stocking suspender clips. I could also feel the trepidation in her as her legs trembled slightly.

Taking up position almost in line with her waist I tapped her bottom with the tip of the crop to get distance and aim. I tapped her bottom several times and when I was happy (and who wouldn’t be) I told her to count each stroke and not to move or stand up until I told her she could do so.

I raised my arm to shoulder height and brought it swiftly down across both cheeks! THWACK! – Jackie let out a gasp and stifled a yell by closing her eyes and gritting her teeth “ONE!” she gasped “Oh god Oh Oh god that stings” she said.

“Ready Ms Jones?”

“Yes sir”

I raised the crop again and whacked her backside another three times. “TWO! THREE! FOUR! SIR! Can I rub my bottom please?”

“Ok! Ms Jones you may stand and rub whatever you want to rub.”

Jackie slowly stood up and gently rubbed her bottom with both hands then lifted her skirt and slip and rubbed it through her pants. Eventually, after about a minute or two she smoothed out her slip and rearranged her skirt and bent over the chair again, “I am ready for the extra one now sir!” she said.

I placed the crop across her cheeks again and tapped a couple of times and then quickly raised it above my head and brought it down hard across her bottom; much harder than the first four. She gasped and shook then jumped up clutching both bottom cheeks… “FIVE FIVE FIVE. No more please Steve that really hurt. Shit Shit Shit that really fucking hurt Steve!”

“Ms Jones, be quiet and sit down please.”

Jackie was now whimpering and crying at the same time and still rubbing her bottom as she gently sat on the dining chair as before. I took my clean hankie from my left trouser pocket and handed it to her to wipe her face and eyes.

“That really hurts Steve. My backside is stinging and feels so hot; I bet I have got lines all over it.”

Standing directly in front of her now I looked down at her weeping face and gently lifted her chin to look at me. I could feel my penis getting rather stiff at this point and decided not to hide the fact. I gave her the crop to hold and then placed my hand on my crotch to move my dick so it would not strain at the zip front and tried to angle it down the left side of my trouser leg.

Jackie saw what I was doing and placed her hand on top of mine. She then pushed my hand to the side and searched for my fly zip which she found and then unzipped me. My dick was pressing hard at the front of my shorts and she then put her hands inside my trousers and eased my hard penis out from it’s captivity into the cool air of the room. She gently stroked it and caressed it from the tip to the base and then pulled the foreskin back to reveal the head which was getting bigger by the second – or so it felt! She leant forward and placed a kiss on the tip and then kissed the shaft and far as she could reach. This started to really excite me as I hadn’t expected anything like this so soon – if at all. She then opened her mouth and placed her lips around the shaft of my penis and began sucking and nibbling gently rocking back and forth to simulate a wank.

“Whoa! Ms Jones. Not all at once please.”

She looked disappointed as I slid my erect penis out of her mouth.

“Will you take your shirt and trousers off to cane me Steve?”

“Why?”

“I want to caned by a man with nothing to restrict his movements, a man that will take me to task and accept no excuses; I need to be punished like a naughty lady should be because I am not a child.”

“You only want to see my dick in my pants, don’t you?”

“I want to feel your dick in me Steve but not before you punish me like you said you were going to.”

I unbuttoned my shirt and pulled it from my trousers that were still open at the fly. Unbuckling my belt I dropped them to the floor and stepped out of them and bent forward to pick them up only to be met by Jackie’s hands as she grabbed them and began to fold them neatly.

“Take your shoes and socks off too please.”

“Are you telling me what to do Ms Jones?” I asked.

“No sir just being helpful.”

Now I was the one in a state of undress being stood there in just my underpants with a hard on still.

Jackie came back and stood in front of me and held my dick again placing her hands inside my pants and stroking my balls. “Am I being naughty sir?” she said.

“Remove your dress and petticoat Ms Jones”

Jackie reached behind her neck and unzipped the dress and slipped it from her shoulders, pulling it from her breasts that were supported by a cream bra she gently eased it over her hips and stepped out of it. She folded it neatly and put it next to my trousers on the coffee table. Then she pushed the waist slip from her hips and stepped out of that and placed it next to the dress and trousers. As she walked back to the chair I couldn’t help thinking how wonderful she looked in the bra, pants, suspender belt and stocking with the high heels setting the image.

“Bring me the thinner of the two canes please Ms Jones.”

Jackie picked the 7mm shorter cane and ran it through her fingers before hand it to me. “Here you are sir.” She said holding it out in front of herself as if presenting it to me.

“Thank you Ms Jones. Now I want you to stand with your feet apart about the width of your shoulders.”

Jackie complied willingly and stood with her feet about 18” apart. “Bend down and touch your toes or as far down as you can comfortably get”

Jackie bent forward and just touched her toes but I could see that this was not quite right as she was slightly unstable so I pushed her foot stool across and asked her to rest her hands on that. In this position her bottom was predominantly uppermost and her pants were tight across both cheeks. They were quite thin too so did not offer much protection from the sting of this thin whippy cane and her high heels kept her legs straight and also pushed her bottom cheeks upward making it easier to aim for.

Again I stepped back and swished the cane through the air and I saw her bottom twitch as is ‘swished’ the air. Placing the cane across both cheeks as before I tapped it a few times and then swiped it down across the centre of her now tight pants and skin. It landed with a sharp ‘CRACK!’ and she jerked and twisted her legs slightly but maintained position. I waited for about twenty seconds and followed the first with another two in quick succession – Crack Crack!

“Oww Oww Three sir!”

Her legs were trembling now and she lifted her left leg a couple of times and looked round at me waiting for the next stroke. I took aim again by tapping her bottom and then Swish – Crack the fourth stroke landed – “Four” she mumbled through muffled tears. I followed through with another two strokes – quite hard than I normally would have done seeing as she was taking it so well.

“You may stand up now Ms Jones.”

“I thought you were going to give me the extra one for being rude sir?”

“Ok then back down”

I laid the last one across her wobbling backside and Jackie eased herself up from the foot stool and placed both hands on her backside then slid them inside her pants. Rubbing her bottom lightly she said, “I can really feel welts and railway lines across my bum Steve but it doesn’t hurt as much as I thought it would – Yes! It does hurt and it stings like mad but not hurt hurt – strange ache really. You know, I didn’t want you to stop but I’m glad you did – look what you’ve done to my nice bottom.”

Jackie pushed her pants down further to reveal a very red bottom with eight bright red stripes across it and two fainter lines across the tops of her legs; they did look sore but she didn’t seem too disturbed by them. She then dropped her gaze to my bulging underpants and said “Your dick seems a bit tight in there Steve.” walking over to me. “Let me help him out of there.”

I put the cane down on the settee and picked up the thicker, longer one. When she got close to me her hands slipped inside the waist band of my underpants and she pushed them down over my buttocks then gently eased my penis from it prison and flipped it out into the open. She knelt on the floor and continued to slide my pants down. She lifted my left foot and removed the pants from it and then she lifted my right foot and totally removed my underpants. Throwing them across the room she said, “They are out of the way now so let’s see what I can do with this!” as she held my dick and gently caressed it back ad forth giving me the most sensual hand job I’ve ever known to that time. She licked it all over and put it in her mouth and moved her head forward almost swallowing me whole and then gently sucking me and she moved her head back. She took it out of her mouth and again licked it all over whilst caressing my balls.

“Steve,” she said “Steve, my clit feels very wet and my arse is sore but I want you to give me six of the best with that cane in your hand now then I want you to fuck me… Please!”

She stood up and turned around and said, “Unclip my bra please – sir!” I gave her the cane and undid the hooks holding her bra in place. Sliding it off her shoulders I felt my dick rubbing her bottom and it felt warm… I slid the bra from her breasts and threw it across to where my pants were and then gently stroked her nipples as they were sticking out like little cherries.

“Over the chair again Ms Jones and take those pants off too.”

Jackie complied willingly by pushing the pants off her shoes and bending over the chair again. This time I didn’t need to prompt her as she stood there with her hands on the chair seat and her bottom high in the air waiting for the cane to punish her glowing red bottom cheeks.

Without further ado I grabbed the heavy cane and warned her that this would really hurt but try to stay still as I wouldn’t want to cane her legs.

I raised the cane and brought it down twice in quick succession as before. She gasped at the first and sucked in a deep breath on the second. I waited for a reaction before commencing but apart from the kicking of her right leg there was very little so I decided to lay it on a little harder. I raised the cane again and aimed it about 2” into her bottom so to say that the contact point was if she was some 2” further forward. It landed with a heavy “CRACK” and brought a ripple from the contact that went up to her waist and down to her thighs.

“Fucking Hell that fucking hurt,” she yelled as she danced about the room holding her backside. “Fuck fuck fuck – shit that fucking hurts…”

Eventually she calmed down and looked at me with tears in her eyes and, still clutching her cheeks, walked back to the chair and bent over it again for the final three strokes which I delivered slightly, and only slightly, softer aiming about 1” inside the skin covering her bottom cheeks and I can tell you honestly that she did jump on every one of those last three strokes.

I placed the cane on the seat of the chair and took hold of her hands and gently raised her up from the bent over position to standing upright. She was totally naked as I was and she rubbed her backside for a few moments and then kissed me. I felt my penis press hard against her tummy and she stepped back a little then stroked it gently. Without a word being spoken she tugged my hand to follow her back to the chair where she bent over it again and parted her legs quite wide revealing her bottom crack and her pussy that was wet and inviting. I ran my hands over her very red and striped bottom and she wiggled as I did so.

“Fuck me Steve…. Please!”

I didn’t waste much time as I caressed her bottom feeling the ridges I had just put there and the heat was as much as a two kilowatt fire. I stroked her pussy gently feeling the wet excitement and gently slipped into her.

Not wanting to end the evening quickly there and then I withdrew after a short while and we kissed and cuddled and ended up in her double bed for the night.

Next morning I got up and made her tea and toast and brought it back to the bedroom where we spent most of Saturday morning.

Come Monday morning back at the office Jackie just smiled at me and said, “Good morning Steve – can I see you in my office in half an hour I want to show you something that happened at the weekend that I think you might be interested in!”…..

Copyright (c) Steven Walsh 2005

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