I was annoyed. I had arranged to meet Leonie, my wife. Slim build. Long black hair. We were going to have a drink here at the hotel bar, then go to the theatre. Leonie bought the tickets. .
She was late. I called her mobile but it went to voicemail. I was about to leave.
I watched the tall woman as she entered the hotel bar. Long blonde hair. She looked about twenty five. She was wearing a sleeveless shimmery dress with the hem just inches below her bottom. Her legs were bare. She wore black high heeled shoes. She carried a smallish handbag with a shoulder strap. I knew my mouth fell open.
She came over to me and looked down at me. She looked stern, yet friendly. Maybe in a dominant way.
She spoke to me. “Anyone sitting here?” she asked.
“No, Miss,” I stuttered.
I felt so foolish. Fancy calling her ‘Miss.’ She was about my age, but just like any girl. Mind you, a very attractive girl nevertheless.
She smirked at my response but the smirk turned in to a friendly smile. “May I join you then?”
I licked my lips. “Please do,” I replied, making sure I did not utter the ‘Miss,’ word again.
She sat on the two- seater with me. Right next to me. I could smell her perfume. It was intoxicating. This beautiful vision held out her hand for me to shake. I raised my hand and took hers. Her hand was warm. Loving.
“I’m Cindy,” she said in a beautiful American accent.
I stuttered. “Jack. I’m Jack.” I was overcome with the sight of her. “Would you like a drink, Cindy,” I asked.
“Thank you, Jack. I’ll have a Sex on the Beach.”
My mouth dropped open. I stuttered, “Of course, Cindy.”
I held up my hand and called over a waiter. I looked at him, blushing. “A Sex on the Beach, please.”
The waiter smiled at me. He glanced at the girl and then back at me. He gave me a, ‘Dream on,’ look. I blushed. He was right. This lady was well above my level.
While we waited for the drink Cindy asked, “Are you married?”
I blushed. Of course I was. Should I lie? I decided not. “Yes,” I said with a false smile.
“I’m not,” Cindy replied.
What a gorgeous smile she gave me. Surely a come on? That smile. The drink. How many signs would I need?
“Been here before, Cindy?” I asked.
“Sure, Jack. I’m a regular.”
I couldn’t take my eyes off the vision. She was beautiful, single, liked a drink with a sexy name, looked sexy, and oozed sex.
Cindy added, “I am staying at the hotel, actually.”
“Really?” I ask thinking madly. “I’ve just come for a drink.”
The beautiful vision eyed me from the top of my head down my chest and stomach. She rested her eyes on my penis? Surely not? She must have spotted something on my trousers. She was staring.
I followed her gaze and it hit me. I couldn’t stop myself growing. My penis was stiffening as she looked. Crazy. Crazy. Yet it was happening.
Her eyes moved downwards to my legs and she studied my shoes. My very expensive black leather shoes. I wondered if she knew the make. She will certainly have heard of them.
My erection stiffened as I studied her more closely. Her hair fell down her shoulders. Her bare arms showed signs of the gym. Her breasts pressed against her low cut dress. Her cleavage was evidence of her full breasts. She sat up straight and her dress clung to her. No tummy to talk of. Her hem was high and showed off her long slim legs. Her bare legs.
She looked up and I know caught me looking at her legs. I looked back in to her eyes. She smiled. I was transfixed.
Her drink came and she took the glass. She gave a lovely smile to the waiter. Perhaps they knew each other given the smile he gave her?
She tilted her glass towards me. “Thank you,” she said with that smile again. That intoxicating smile.
We chatted. She was so easy to talk to. She told me of her family. Her parents in Los Angeles. Her brother in New York. Her sister here in London.
“Where in London?” I asked.
“Not far from here, actually. I will be meeting up with her tomorrow.”
I wanted to ask if her sister looked like her. I couldn’t get the words out.
One drink followed another. Hers was the sexy sounding Sex on the Beach. Mine was malt whiskey.
The time passed. So quickly. Where did it go?
I even forgot Leonie hadn’t turned up. I didn’t even think to get worried either. The drink did that. Drinks.
I wondered how come Cindy managed to have so many drinks but her speech didn’t slur.
Cindy said, “I guess it’s getting late.”
I looked at her. I wanted her.
She stood up and smiled at me. “You have been so nice to me, plying me with drinks. Let me return the favour.”
My mouth dropped open. I looked at the bar. It was closing.
Cindy saw the bar was closing as well.
“There is a mini bar in my room. Can I trust you?”
“Of course,” I said. Too quickly perhaps? “Yes, of course,” I repeated trying a sincere tone of voice which I think I pulled off.
It worked. “OK. I’m on the third floor.”
Cindy waited for me to stand up. I was still looking up at her in her high heels. I don’t usually go with women taller than me but Cindy made me feel tall. I got envious looks from men, and women, as we walked towards the lifts.
Cindy pressed the button for the third floor. She looked at me. Her eyes burnt in to mine. Eyes full of desire? Maybe of too many drinks? I didn’t know. I didn’t care. We were on our way to her bedroom.
Cindy asked again, “You’re sure your wife won’t mind you coming to a lady’s bedroom?”
I hadn’t thought about that. Of course Leonie would be mad with me. Yet Cindy was here. Now. “Honest, Cindy. She’ll be cool with it.”
Cindy smiled at me. A delicious smile.
The lift stopped. The doors opened. We got out and I followed Cindy towards her bedroom. I was transfixed by her bottom. Her gorgeous wiggling bottom as she walked. She got out the card as we walked. She flicked it in the lock and the door opened. I followed her in and closed the door.
I looked around the room. It was large. It had a king sized bed with side cabinets on both sides. A table with a huge TV on it. French doors to a balcony. All luxurious. Like Cindy.
“Drink?” she purred.
“Whiskey, please,” I replied.
Cindy poured me the drink and one for herself. Not whiskey but clear. It looked like water but I doubted it was. Not with the amount of alcohol she had consumed in the bar. She must be as tipsy as me, I reckoned.
Cindy sat on the bed next to me. We clinked glasses and we drank. We chatted again. Just like in the bar. I felt comfortable. Relaxed. Albeit the drink was getting to me. However, it will be getting to Cindy as well.
“Another?” she asked.
“Please,” I replied, slurring my speech slightly. I hoped she didn’t notice.
She handed me the drink. Our fingers touched. Hers were sensual. Our eyes caught each other.
“I feel warm,” Cindy said.
“Me, too,” I agreed. It was warm to be fair.
“Mind if I take my dress off, Jack?”
My mouth dropped open. I know it did. “Sure, Cindy. Your call.”
She turned and beckoned me to unzip her dress. I did with fumbling fingers. The zip ran down to the top of her bottom.
Cindy turned, smiling. She slipped the straps down her arms and pushed the dress to the floor. She stepped out of the dress and scooped it up. She folded it and put it on to a chair.
The vision turned to me. In her bra and knickers.
“You are sure your wife won’t mind, Jack?”
“Sure,” I stammered.
We chatted whilst we sipped our drinks.
“Another one?” Cindy asked with what I thought was a wicked smile. Was it a come on, I wondered?”
Cindy handed me the drink and again sat down on the bed next to me. Closer than before. Her bare thighs touching my legs.
Cindy put her hand on my thigh and asked with that same wicked smile, “So, Jack, when you called me, ’Miss,’ in the bar did you want me to dominate you?”
I nearly spilt my drink as I spluttered, “I’m sorry?”
Cindy’s gaze hardened. “Just what I asked you, Jack. Are you a naughty boy who needs to be disciplined?”
I held the glass in front of my lips. I didn’t dare take a sip. I looked in to Cindy’s blazing eyes and succumbed. “Yes, Miss,” I replied. I then took another huge gulp of whiskey.
Cindy said forcefully, “Good. So get undressed.”
My mouth dropped open. My breathing was laboured. I knew I was tipsy from the whiskey and that probably stopped me objecting. Still, I was in the company of a beautiful woman who told me to get undressed. What the heck?” I thought.
Cindy took my glass and went to fill it up again.
I stood up and quickly undid the buttons of my shirt. I slipped the shirt down my arms and threw it over a chair. I undid my trousers and pushed them down, catching my pants on the way. I stepped out of both and threw them on the chair as well. Using the table to balance my socks followed.
I stood naked.
Cindy was staring at me with a grin. She wasn’t looking at my face but lower down. My eyes followed her gaze and I saw what she saw. My erection. No secret I was really turned on, then.
“Sit,” Cindy ordered.
Cindy handed me my drink and sat down. Our naked thighs were touching. I was still spellbound.
“So, Jack,” Cindy asked smiling. She put her hand on my naked thigh. “How naughty have you been?”
The smile was intoxicating but I knew she was playing with me. I loved the game. “Very naughty, Miss.” I didn’t tell her how my fantasy was to be caned. I never was at school but often masturbated thinking about bending over in the Head’s Study.
“Naughty enough to require the cane?” Cindy asked sternly.
How could she know that, I wondered? I swallowed hard. “Yes, Miss,” I replied quietly.
“Then the cane it shall be.”
Cindy stood up and ordered, “Lie on your tummy with your arms stretched up towards the top of the bed.”
Almost in a trance I obeyed. As my arms stretched upwards Cindy was at the top of the bed and was securing my wrist in a leather clasp. Oh my goodness, I thought. Is this real?
Slowly Cindy walked around the other side of the bed and secured my other wrist. She went to the bottom of the bed and secured my legs, one after the other. She sat on the bed and ran her hand over my bottom. Large slow circles.
“Have you ever been caned, Jack?” she asked.
“No, Miss,” I replied.
“I like it when I am the first, Jack,” she purred.
Cindy removed her hand from my bottom and stood up. I tried to follow her as best I could as she went to a cupboard. Moments later she re-appeared in my line of vision holding something. I gasped when I saw that it was a cane with a hooked end. Just like my fantasy.
She stood by the bed and tapped the cane on my bottom. “Ready, Jack?” she asked firmly.
I turned away and closed my eyes. “Yes, Miss,” I replied.
There was a gap. I was sure I heard a swishing noise followed immediately by a thwacking sound. Both merged in to pain I had not felt ever before.
I screamed out.
“Oh dear, Jack. Too much noise,” Cindy said in a business like tone. “Open,” she ordered.
I felt the silk knickers as I opened my mouth.
A few moments later I heard the swishing sound again and the pain once more spread right across my bottom. A few moments later and the third stroke of the cane thwacked down on my bottom. I groaned each time but the knickers stopped me screaming out. That was good, I thought.
“Are you OK, Jack?” Cindy asked. I felt her hand rubbing my bottom. Round and round. It felt so good. Her hand slipped down my inner thigh and brushed against my balls.
I focussed on my erection and knew it had stayed stiff. Even so my erection stiffened further with Cindy’s touch. . It was the soft touch after the pain that so aroused me.
Her hand left my bottom. A few moments later and the cane bit in to my bottom again. The cane again bit into me after a few moments more and again a few moments later.
I savoured the cane strokes. I didn’t need to speak. The pain engulfed me as my erection stiffened. Pain and pleasure. Just as I had hoped.
I reckoned Cindy knew to leave me to enjoy the pain. Moments later and without a word another stroke bit in to me. I know I threw my head back but still the knickers stuffed in to my mouth prevented anything more than a grunt.
I wanted more. I couldn’t speak and so lifted my bottom in to the air. I was beckoning more strokes.
As though reading my mind the next stroke bit in to my bottom and a few moments later the next. I had lost count but didn’t care. I lifted my bottom again and was rewarded with another stroke and a few moments later another.
The pain covered my whole bottom. Could I take any more, I wondered.
The next moment the cane bit in to my bottom again. I raised my head gasped out loud. My head hit the bed and the next stroke bit in to my bottom. Again my head rose. Again when my head lowered to the bed the next stroke bit in to me.
I was exhausted now. Overcome with pain. Still, I focussed on my penis and jiggled my hips. It was still there. Erect.
I felt a hand rub my bottom and again slide down my inner thigh. This time instead of just brushing my balls the hand continued. I raised my bottom and the hand slid around my ball sac and squeezed. It was mind blowing.
After several squeezes that were firmer and firmer the hand moved upwards and around my erection. I had already leaked and the fingers slid more easily, up and down.
I gasped as I could feel myself coming. I gyrated and the fingers helped me along. Firm fingers holding my erection. My breathing shortened until I exploded. I came. It was wonderful. So different to anything I had ever experienced before.
My head hit the bed again. I was exhausted. I lay there as the hand rubbed my bottom.
I felt something had changed. The hand was different. I opened my eyes and looked around. It wasn’t Cindy sitting rubbing my bottom. It was Leonie.
“What the?” I stammered but couldn’t move as I was still tied to the bed and as the knickers filled my mouth I know all I did was gabble.
Leonie smiled. “Hey, sweetie. Did you enjoy my Valentines present?”
I stared open eyed. Valentine’s present? What does she mean? And where is Cindy?
I immediately realised Cindy was part of this. I gabbled again and Leonie lent forward and took the silk knickers out of my mouth.
“Cindy is a friend from work. Well actually she works in one of our overseas offices but we got to talking. You once told me how you fantasised about being caned but scoffed when I suggested I try it. I asked Cindy what she thought and she came up with this?”
I was still speechless. So many thoughts went through my mind. Not least how do I explain that I went to a girl’s bedroom?
Leonie knew me so well. “I was sure the drink would take hold. Cindy’s didn’t have any alcohol in them. That was arranged with the waiters beforehand.” Leonie added after a moment, “It’s OK, Jack. I know your weaknesses. Anyway, you won’t have to go elsewhere any more. I’ll be caning you from now on.”
I looked shocked but when I saw Leonie’s grin I knew she meant it.
“Ready to be untied and give me a present?”
I looked at her quizzically but before I could answer she went to the four leather clasps and untied me.
“Get up,” she ordered.
I looked around as I got up.
“Cindy went to her room. She left after the first three strokes.”
I smiled at my wife. “Really?” I asked in wonderment.
Leonie stepped over to me and cool as anything put her hand around my balls and squeezed. I gasped.
“Don’t even try to remove my hand, buster,” she snapped.
I felt the push and she forced me back towards the balcony door. The cold glass squashed my bottom. I gasped out loud. It was cold and hot against my welted bottom. My erection stiffened.
Leonie lifted her dress. “No knickers, Jack. They have been in your mouth.”
She guided me inside her. She was already wet.
“I reckoned caning you would turn me on, Jack. I just needed some help.”
She gasped as my erection slid inside her. We gyrated. My bottom still stinging from the cold glass. Leonie gasping as she went closer to orgasm.
I held back. I had to let her cum first. I could hear from her gasps she was nearly there.
Leonie let out a long gasp. Like she does when she reaches orgasm.
“Stop right there, Mister,” she ordered. “You are mine and will obey me. OK?”
“Yes, Miss,” I replied to my new and dominant Leonie.
Leonie eased herself off my erection and again clasped it in her hand. She squeezed.
I gasped but enjoyed being under her control.
“Say thank you,” Leonie demanded.
“Thank you, Miss,” I gasped.
Leonie smiled at me, her face so close to mine.
I smiled back at my wife. “Thank you, Leonie. I wouldn’t have had the courage to do that by myself.”
“What, allow yourself to be seduced?”
I blushed. “Well, I meant more getting caned.”
“I know, sweetie. That’s what love is. Being trusting at all the right times. ” Leonie squeezed my balls again.
I gasped. “Yes, Miss,” I said with a smile.
“Well, we have the room for the night. How about some tie and tease?”
“What’s that involve?” I asked.
“I tie you up again, give you another whole load of cane strokes, and then we make love.”
“I guess that is another form of seduction,” I said smiling.
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