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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.