Jenna's Erotic World Ch. 10

We spent the day shopping. When we returned to our rooms, we both had an armful of bags. We went to my room and emptied the bags on the floor. All the items on the floor were from various sex shops we had gone to. Some of the items included a large twelve inch dildo, a pair of wrist and ankle restraints, a riding crop and a big paddle, a variety of vibrators, a selection of anal plugs and toys and some specialised leather panties.

It was these panties I wanted Ana to use. She looked excited and nervous at the same time. My mind raced with the possibilities.

"Ana remove your clothes now." I ordered her.

"Yes Tony." Ana said submissively.

She undid the buttons of her blouse and removed it. She then slipped out of her jeans and stood before me in her lacy underwear. She looked at me and smiled coyly. She bent over to undo the straps to her high heeled shoes giving me a clear view of her fantastically shaped ass. She then stood up straight and kicked her shoes off.

Next Ana raised her arms over her head as if she were stretching which had the effect of lift her breasts up high and separate them slightly so that her sexy cleavage was right in my line of site. She reached back and undid the bra and slipped out of it. Her tits now free swayed in front of me as she bent over again this time to slip out of her panties. She now stood in front of me naked.

I reached over and grabbed the leather panties. They had a couple of special straps on the inside at the crutch. It was designed to have different attachments added. I looked at the variety of toys that we bought and finally decided on two. One was a short vibrator which came with a wireless remote control. The other was a good sized anal plug.

I locked them into place and called Ana over. She stepped into the panties and lifted them up to her knees. I then squeezed a glob of lubricant on the tip of both the vibrator and the anal plug. I then put some on my index finger and smeared it around Ana's tight asshole.

I massaged it around and into her bum hole enjoying the sensation of fingering her ass. I then lifted the panties slowly up her thighs until the vibrator was at the opening of her pussy. I pushed it in a little bit until the tip of the anal plug pushed up against Ana's dark love passage. I pushed it in gently fascinated as her sphincter stretched to take the pair shaped plug.

Ana sucked in her breath as the widest part of the plug slipped through and her ass tightened immediately around the narrow base as if trying to swallow it. Both her holes were now tightly filled. The wire to the remote receiver fitted on the outside of the panties and could easily be concealed under clothes.

I got Ana to sit down.

"How does that feel?" I asked.

"A little uncomfortable, but doable." Ana said.

"Good. Come over here" I said.

Ana walked over to me. I had to give her credit, even with both of her holes filled she could still walk elegantly. I picked up the wide leather wrist cuffs and buckled them tightly. I then turned her around and brought her arms behind her. The wrist cuffs were designed to be locked together which I is what I did.

I then took a thin leather collar with small studs all the way around. I put this around Ana's throat and tightened it, so it was snug. I grabbed a black leather leash that came with the collar. I attached the clip on one end to the silver loop at the base of her throat. I looked her over. I liked what I saw.

"You need to go get ready for dinner tonight" I said.

"My hands are tied. You will need to get my things." Ana said smiling.

"No, we are going to go back to your room."

She looked at me quizzically and then understanding dawned on her. The smile left her face.

"I can' go out like this!" She exclaimed.

"You will do as I say." I ordered and to make my point I pinched one of her nipples between my fingers. Ana gasped and cast her eyes down as she nodded her acceptance.

Her room was two doors down, not far but far enough when you area essentially naked and bound in bondage gear. I opened the door and walked out tugging on the leash forcing her to come out like a reluctant dog. The corridor was empty except for a house cleaner coming out of one of the rooms.

She looked up at us as we walked past. Her eyes wide and her mouth hung open in disbelief as I led Ana, head down, eyes cast down, and blushing bright red, past her. We got to her room, and I opened the door and walked in. Once inside I closed the door and pushed Ana up against it. I kissed her hard while I fondled her breast. I was hard and needed release.

I moved away from Ana and began to remove her bindings. Time for that latter. She passed my test. I took out a small remote from my pocket.

"Let's evaluate that thing inside you." I said turning the switch to low. Ana sighed and I saw a shudder run through her.

"Well? How does that feel?" I asked.

"Oh god that feels nice." She said.

I smiled and decided to switch the setting to high. Ana nearly fell to the floor as her knees just about gave way as the sudden vibration electrified her clit.

"Now sit down." I said.

Ana sat on one of the chairs. Almost immediately her body started to shake as her orgasm raked her.

"That puts the pressure right on my clit" she said and smiled at her release.

"Get those panties off and shower. We need to get ready." I said turning the silent vibrator off.

Ana removed the panties and together we went to the shower. While we both showered together, I forced her against the wall and lifted one of her legs up so that I could get access to her pussy with my now throbbing cock. We fucked each other passionately in the warm shower.

When we had dried off, I lubed up her ass again and helped her put the panties back on. Again, her ass seemed to swallow the anal plug as the little pear was pushed in. Once she had her panties on, she reached for her bra.

"No. Not tonight. You are going bra less." I ordered.

She looked at me for a second then complied. She then began to put on her evening dress. It was beautiful black dress with no back. The front came over her breasts and was tied at the back of her neck. It had a very deep plunge at the front giving a spectacular view of Ana's generous cleavage.

From the side you could see the swell of her breast making this even more alluring. She put on her dark high heel shoes on and went to apply makeup. I dressed in my good evening suite and in a brief time we were heading to one of the expensive restaurants.

We hailed a cab and got into it. Once inside I decided it was time to play. I reached into my breast pocket where I had placed the remote to the vibrator buried deep in Ana's slick cunny. I switched it to low. Ana barely stirred though I could see in her face that it was stimulating her. I left it running on low for the short cab ride to the restaurant.

When we arrived, we were seated at a table in the middle of the room with many people around. There were a lot of couples sitting in intimate dinners, but more than one male partner (and a few women as well) turned to watch as Ana walked by. She was amazingly graceful in her walk and the dress which showed the soft swell of her breast and the cleavage that beckoned the eye to explore had the affect I wanted.

I planned to make her perform in public tonight. As we sat down a waiter came over to take our order for drinks. I had the remote in my hand under the table. As Ana was about to order some wine for herself, I switched the vibrator to max. Ana's eyes widened suddenly and she hissed an intake of breath. The waiter looked at her in concern.

"Are you alright Ma'am?" he asked.

"I am fine. You have the wine I like that is all." Ana tried to cover up. I'll give her credit she was doing a good job at pretending everything was normal, but her breathing had quickened slightly and she was having a hard time concentrating with that vibrating cock deep in her pussy. I turned it back down to low allowing her a chance to compose herself again. She picked the wine she liked, and I ordered a bottle.

"That was not fair!" she said to me when the waiter had left.

"I will decide what is fair and what isn't, my beautiful vixen." I said with a smile.

"I am so embarrassed. I feel like everyone is looking at me." She said.

"Some are. You are a beautiful sight. I noted many men here watching and thinking their wet dream had walked in." I told her. "How are those things in your holes? Nice and snug?"

"The vibrator is keeping me on the edge when you have it low. When you push it up, I have to struggle to keep control and not have an orgasm in front of everyone. The anal plug has me filled up. I keep feeling like I have to push it out of me. I really have to concentrate to keep my ass muscles clenched." She said shifting uncomfortably in her seat.

"It will not pop out. It will have stretched your asshole nicely for latter tonight when I fuck it." I told her just before the waiter returned with our wine. Ana was flushing and looking very embarrassed again. The waiter looked at her oddly but said nothing and continued on with his job.

Several more times to waiter came and each time he did I would increase the speed of the vibrator buried deep out of sight. The slight moans and gasps that escaped Ana when I did this was starting to attract attention. At one point when I turned the speed back down, she reached over the table and grabbed my hand.

"Please! Can I come? I am on the edge. One more burst like that and I will lose control." She begged me.

"Remember the agreement. You are not allowed to come in public. You are to act as if nothing is a miss. If you, don't you will be punished." I reminded her.

"I don't know if I can control it." Ana whimpered. I was hoping to hear that.

"Alright then, let us change the rules a little bit. For every time you come, you will get five strokes." I said with a grin on my face. This was going to be good.

"Five strokes?" She asked. "Five strokes of what?"

"Your choice of the new toys. The paddle, the riding crop, or the flogger." I said graciously.

She gulped and a nervous crease furrowed her brow. I turned the speed up on her vibrator again. Ana looked at me and I could see the plea in her eyes, but I just watched as I ate my meal. She tried several times to eat her own, but suddenly with a loud intake of breadth I could see her begin to shake as her body overrode her control and she orgasmed.

Under the table I could feel her legs thrash as they twitched in ecstasy. I looked directly at her and said, "That's one" and turned the speed up another notch. Her forehead had a trace as she tried valiantly to fight the next wave of pleasure threatening to overtake her. People were beginning to look at us. She was unable to keep some of the gasps and moan suppressed as she did earlier in the evening.

Her knuckles were white as she gripped the table while another orgasm went through her. I knew now that her strength was at its end. I turned the speed to full and sat back and watched as over the next 10 minutes she was racked with orgasm after orgasm. I counted six more on top of the first two before I turned the vibrator off. She was flushed and breathing heavily. She also looked exhausted.

"How are you feeling?" I asked her.

"My pussy is super sensitive. I think it will be hard to walk. My legs and panties are soaked with come. Good thing my dress is black because otherwise there would be a damp spot around my bottom." Ana admitted.

We left the restaurant, Ana walking a little less gracefully than when she came in. We caught a cab back to the hotel. Once in Ana's room I got her to undress. I watched as she pulled her panties down. They were soaked. I could see her wince as her asshole stretched as she pulled the anal plug from her butt hole. I got her to bend over so I could inspect her holes.

Ana's labia were swollen and red. Her asshole was also red and a little swollen. I pushed a finger into the tight puckered hole which opened easily to allow my finger in. I pushed two then three fingers, without too much resistance. Before I could enjoy this sexy sight, I had work to do.

"I counted eight times. That makes forty strokes. How do you want it?" I asked her.

"Not the riding crop. Any of the other two." She said. I smiled.

Ana looked a bit frighted but I could see the excitement. I placed the wrist and ankle straps on her and made sure they were nice and tight. I then linked the wrist straps together so that her hands were bound in front of her. I led her to the table and positioned her so that she was laying across it arms stretched in front of her, breasts pressed against the cool top. I then grabbed several more leather straps and bound each of her legs to the table legs so that they were spread far apart.

I went around the front, took her bound hands, and used the long straps to bind her the other side of the table. I stood back and looked at my handy work. Ana's ass was perfectly positioned, her legs spread wide giving a beautiful view to her stunning pussy. She was stretched across the table, so she had very little movement in her arms.

I decided she needed one more thing. I went to bag of stuff we had bought and pulled out a ball gag. I walked in front of her and placed the ball in her mouth and tied it around her head.

"You will want to scream once I get started. This will muffle it." I said.

I then walked behind her and picked up the paddle. I lined it up and gave a swing. WHOMP. It connected hard and her ass cheeks rippled with the impact. She let out a yelp. I raised the paddle again spanked her ass with it five more times in quick succession. Her backside was starting to get nice and red. I swung four more times aiming this time at her upper thighs just where the flesh of the buttocks meets the upper legs.

Ana had begun to cry slightly. She was trying to move away from the blows, but she was bound tight and couldn't go anywhere. I decided that the next 10 would be with the flogger. I put down the paddle and picked up the short, handled whip like object and inspected the many wide leather strips that made up the whipping end. I gave it a test swing.

Satisfied with the weight and feel I began to swing it in a full circle. Each time the circle arc completed it contacted Ana's ass making her squeal through the ball gag in her mouth. I had worked up a sweat as had Ana. There were ten more strokes. I placed the flogger down and picked up the riding crop. Ana could see me with it in the corner of her eye.

They opened wide in terror. She shook her head as if to say no. I walked behind her and swung hard. THWACK. She screamed under her gag. THWACK THWACK THWACK.

Ana was now crying hard with the pain and bucking desperately to get loose. I saw then also a pearly drop shining at her pussy lips. Despite the pain she was getting wet with excitement. All thought of finishing her punishment went out of my mind. I pulled down my pants and let my rock hard cock spring free. I positioned myself behind her and pushed my rod into her wet, slick cunt. The warm folds wrapping around my dick.

I began to thrust hard into her. I could hear Ana begin to moan in pleasure. I continued to push deep into the dark hairy snatch. After a while I pulled all the way out, repositioned and thrust myself all the way down to my balls in her asshole. It slipped in easily having already been lubed and stretched by the butt plug. Ana's ass was still tight, and she gripped her muscles tightly so that it felt like a warm slick hand gripped my cock hard.

I thrust several more times and then suddenly came with great force, deep in her anal passage. I pulled out and watched as my creamy white come dripped out of Ana's asshole.

I untied Ana who stayed slumped on the table. I removed the ball gag and she looked up and smiled at me.

"That was intense. I came so hard." She said to me.

I kissed her as she stood up. We walked together to the bathroom to shower.

The next few days was filled with this type of activity. On some mornings I would wake to find my cock being massaged with Ana's mouth. It was a sexually charged few days. On the day we were to head back, Ana said to me:

"You know that we have to go back to the way things were before we came here" she said.

"Only in public. In private however you are my personal plaything. Agreed?" I asked smiling. She smiled back.

"Agreed." Ana answered.

The flight back was uneventful. We got back to the airport around 6PM. We collected our bags, and I was excited to see that Jenna had come to pick me up. I was surprised to see Jas was here as well. I gave Jen a big hug and kiss and together we walked towards the car. As we walked past the Cab stand, I saw that Ana was about to get into a cab. I walked past to say a farewell.

"See you in the office on Monday. Have a good weekend." I said innocently. As I said that I reached into my pocket and activated the remote to the vibrator deep in her cunt. I set it to max knowing the only way to turn it off was to remove the panties and pull the batteries. She would not be able to do that in the cab and her ride was about an hour to her apartment. She sucked in her breath and looked at me and smiled.

"I'm enjoying it already." Ana said.