Vacation with Shari

It has been quite a while since I last told my story. I left writing for Literotica because of the emails I received. Many men wanted me to meet their wives, hoping it would lead to a threesome and a few women wanted to explore their curious side. But, it was the hateful, violent emails that made me go away. Since then, there have been occasional inquiries asking what is new in my life and adventures so for them, I'll update on all that is happening... There are several stories about my introduction to enjoying women and the past women in my life. If you want to see how Shari and I developed to this relationship, you can read those stories. Otherwise, I hope you enjoy this story as much as I enjoyed living it.

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When I last told stories of my life, Shari and I were about to leave on vacation. It was a vacation thought that led has never changed. When we talked about going on that vacation together, Shari was reluctant to let me pay for everything on the vacation even though she knew I had been taking care of her at home for our entire relationship. In her mind, letting me pay to a vacation was something additional, something that she should contribute toward enjoying. So, when she said she didn't have the money for the vacation, my first thought was to give her a way to earn her vacation money. My second thought, which I had quickly expressed, was to tell her that I was taking her on the vacation, not as my partner (which she clearly had been for quite some time), but as my vacation slave. Not only would I get to enjoy her in any way that I could imagine, but she would also service me in any way that I could imagine.

When I offered her the opportunity to be my vacation slave, she looked at me with a puzzled expression. Then she spoke, "I'm your partner, but for this vacation, you want me to be your slave?" I nodded my head, confirming the answer. "What does that mean?" she continued.

I looked her in the eyes, "You'll do whatever I tell you to do...You'll please me in any way that I tell you to please me...You will obey me once we arrive at our vacation...Do you agree to that?" Now it was Shari's turn to nod her head in agreement. I leaned forward and took her into my arms, kissing her deeply. That short conversation had turned us both on as we imagined what the vacation would be like.

I took Shari by the hand and led her to our bedroom. As we stood by our bed, our kisses intensified. I pulled her shirt over her head and unhooked her bra. I pulled off my shirt and dropped by bra to the floor. As we hugged again, our bare chests pressed against each other. Our passion continued as we both removed our shorts. My hand quickly slipped into her panties and I began to rub her aroused pussy. As our kisses continued her hand entered my panties. I pushed her onto the bed and hooked my fingers over the waistband of her panties, pulling them down to expose her lusciousness to me. As I stood over her, I pulled off my panties and climbed on top of her. I positioned my pussy directly over hers, interlocking our legs and began to scissor her. My pussy rubbed against her with unbridled passion. I pressed against her, our combined moans filling the air. My clit was furiously pressing into her giving us both an intense massage. Shari bounced off the bed as the gyrations of her hips met mine, giving each other pussy-to-pussy massages. I felt her passion growing as my body was filled with orgasmic delight, the sensations radiating from my pussy to fill my body. Sometime in the midst of my repeated orgasms, Shari joined me in body filling pleasure as the waves of her climax filled her body.

After that encounter, all discussions of the pending vacation focused solely on the logistics of the trip. Airline reservations, rental car, packing as if all would be a normal time together. What Shari didn't know, but I'm sure she suspected, was that I was making other preparations for our time together. Planning, purchasing and preparing were all completed without Shari's input.

At last, we reached the time for our vacation. As the Uber took us to the airport, Shari was filled with nervous anticipation of what would happen. How would she be treated as my slave. As we sat in the back seat of the hired car, Shari leaned to me and asked what she should do, when would the new relationship begin. I assured her that she would be told everything at the right time. Her time as my slave would begin when we landed in Florida and that I would give her instructions at that time. Her eyes lite up with thoughts of what I would require. She was nervous but also intrigued as to what would happen once we landed.

We arrived at the airport, checked our luggage, clearing the check-in process with its normal long lines and frustration. Our flight was on time and we boarded with the other passengers, nothing seeming different from our normal life. Landing in Atlanta, we easily transferred to the second plane for the final leg of our journey to the Florida condo. Shari commented that she recalled the dread of her first trip when I rescued her from the mess she had encountered when trying to go as a "working girl" to pay off her debts. She thanked me yet again for all that I had done for her. We boarded our plane for the short trip to our final destination. As we were in the air, I handed Shari a sheet for her to read. She looked at the heading, "Shari's Vacation Instructions".

It read: "You are now my slave and will do whatever I tell you to do without question. If you do not want to continue this plan now or at any time while we are in Florida, you should use the word "serious" in asking me to stop. We will then decide how to continue. Whenever you address me (unless someone can hear us), you will address me as Mistress. I will tell you what to wear and what to do. You will pleasure me upon my request. A good and obedient slave will be rewarded with receiving pleasure. A disobedient slave will be punished. Do you understand and agree?"

Shari leaned over and whispered into my ear, "Yes Mistress, I am your slave and will do whatever you tell."

Our flight landed and we walked to the terminal, grabbing our carry-ons as we exited the jetway. As we reached the terminal, I told my slave to watch our bags while I went to the restroom. Upon returning to her, I opened my small suitcase and pulled out a bag, handing it to Shari. I gave her the first instruction of the trip, "Go put this dress on. It is a halter top so no bra will be necessary. Also, you will not wear panties for this trip unless I give you permission. " She looked at me with a smile and took the bag, walking in the bathroom with a cautious smile on her face.

She returned moments later wearing the short halter dress, pulling it down as she realized the shortness of the dress. "Mistress, do you like the dress?" I looked at her with a lustful smile, "Yes my slave, you look good enough to eat in that dress."

As I went to the rental car counter, I sent my scantily clad slave to grab our other luggage. Our main suitcase came off the conveyor belt and she struggled with all of our luggage. I looked at her, "It is so good to have a slave to handle the luggage." Shari dragged our bags to the rental car as I easily walked with only my backpack and a smile.

When we reached the car, we loaded the suitcases and she moved to the passenger side. As she opened the door, I stood beside her, slipping my hand up her dress to rub her cute ass. I found that she was still wearing panties. I admonished her, "I told you that you should not wear panties. Why did you not obey?"

Shari quickly replied, "Mistress, we're in public...going to the store...this dress is so short." I looked at her and reminded her that she would now be disciplined. With a stern glance, I told her to remove the panties and get in the car or her punishment would be increased. She glanced around, saw that noone except me could see her and reached under her dress, sliding her panties to her feet and stepping out of them before she sat in the car.

As I sat next to her in the drivers seat she spoke, "Please Mistress, no punishment. I'll obey." I looked at her, "Show me you pussy as we drive to the grocery store. I want to see you all the way across town." Her fingers slipped to the hem of her dress and she exposed herself to me. As we drove across town, my hand slide over to Shari's pussy several times. She became more and more aroused as I played with her growing clit at each stop light. As I teased her, each touch increased her arousal but I always stopped before making her reach a boiling point. Whenever she would reach to me I would stop her and remind her that she was my plaything and I would make her pleasure me later.

As we entered the grocery store, I reminded her that she was to follow instructions. She nodded her head as we grabbed our cart to get our supplies for the week. First, in the produce aisles, I found several potential purchases to make sure Shari continued to think of sex. Looking at carrots, I said that we should find her the largest. Then I rubbed my hands up and down a cucumber as she looked at me with wide eyes, questioning who may be looking as I suggested how a smooth, large vegetable could be used. As we continued to shop, I could see her nipples poking against her dress, the lining of the halter wasn't nearly thick enough to contain the sign of her growing arousal. At the same time, I could feel my own arousal growing as I thought of the ways I would order Shari to pleasure me once we reached the condo.

Finally, our shopping done, we returned to the car and finished our drive. In those final few miles, I felt Shari's swollen clit a few more times and reminded her that as my slave, she would be pleasuring me once we reached the condo. After pulling into the parking garage, I ordered her to get our luggage and groceries up to the condo. I walked empty handed to the door, telling Shari how great it was to have my own slave to take care of things. After a few trips between the car and the condo, Shari had everything inside. Groceries in the kitchen, suitcases in the bedroom.

I called to her, "Slave, get in here now." She hurried from the bedroom, "Yes Mistress, what do you need?"

I looked at her and ordered her to lean against the back of a chair. "First, it is time for your punishment because you disobeyed me and left on your panties." She began to beg for forgiveness rather than punishment. "No, you must learn your lesson. It will not be harsh since it was your first disobedience...but I will show you that you show obey." She dipped her head and leaned over the back of the chair. I lifted her dress, revealing her bare ass. She was breathing deeply as I brought my hand downward to slap her ass. Not hard but enough to fill the room with the sound of the slap and her aroused moan. As I spanked her a second time, her moan was louder. The third and final spank brought a yet louder moan. She was enjoying our game much more than I anticipated. I wondered if there would be later disobedience just so that she could enjoy a second spanking.

"Stand up and get naked," I ordered her. As she pulled off her dress and it dropped to the floor, I also began to strip off my clothes. When I was naked, I moved to the chair and sat down, draping my legs over the arms of the chair. My pussy was spread wide as she looked at me. "On your knees slave" I ordered. "it is time to service your Mistress." With that command, Shari dove to my pussy with and began to lick and suck with all her might. Her tongue moved over my clit and pussy lips intensely as she showed me the arousal I had created while playing with her as I drove and spanking her after arriving. Shari alternated between stroking my clit with her tongue and penetrating my pussy as I pulled and squeezed my nipples. My obedient slave pleasured me intensely with her mouth and hand. As she licked and sucked on me, I noticed that she was beginning to moan from the feelings she was giving herself with her hand between her thighs.

I grabbed her hair and pulled her face up to look at me. "Are you rubbing your own pussy when you're supposed to be pleasuring me?" I sternly asked her.

With wide eyes she replied, "Yes Mistress, I can't help it. You've made me so horny that I can't resist my own pussy."

I ordered her, "No, use both hands and your mouth on me. Your pleasure must wait. I will tell you when you can cum."

With that, I pushed her face back to my pussy and felt her hands pull me open wide so that her mouth could wrap around my aroused. As her tongue and lips massaged my cum button, I felt her fingers penetrate me and begin to rub the inside of my aroused pussy. I moaned to her, "Yes my slave, yes... that is what I want...please me...please me." She continued to run her tongue up and down me. She continued to fill my horny pussy with her fingers, swirling them to my total enjoyment. Her lips squeezed my aroused clit as she sucked it into her mouth. I could feel the waves of satisfaction building in my body as her mouth massage continued. Soon, my moans filled the room and then turned to screams of "I'm cumming...I'm cumming...I'm cumming." as Shari caused total orgasmic delight to fill me.

I lifted her face from my pussy as her fingers slipped out of me. I gasped to catch my breath as the last waves of pleasure flowed through my body. I closed my eyes and let my head rest back against the chair, fully satisfied by my friend and slave.

As I sat there, I recalled that Shari had been pleasuring herself before giving me those totally wonderful orgasms. I realized that provided me with another opportunity to punish her sweet bottom before I returned the favor and tasted her sweetness.

I looked her, "You were pleasuring yourself without permission, weren't you?"

She looked down, "Yes, Mistress. I touched myself." She stood before me, "Look Mistress, look how my pussy is so aroused. I know I should have waited for permission. Please don't punish me." As I looked at her pussy, I was filled with desire to suck her, lick her...make her cum hard. But instead, I first ordered her to return to the back of the chair and lean over it. Her bare ass displayed to me. I told her that she was not to touch herself without permission, that she should ask for pleasure and know that she could not have it until I allowed it. She nodded her head in understanding as my hand swung downward, giving her an unexpected slap on her sweet ass cheeks. Her gasp showed both surprise and a hint of pleasure. So I gave her another spank...and another...and a final slap against her ass.

Then I ordered her to return to the front of chair and pushed her into it. I lifted her legs over the arms of the chair, spreading her aroused pussy before me. "Those spanks are the punishment for a slave who forgets to ask for what she wants. Do you understand?"

"Yes...yes...yes," I understand she stammered.

I looked at her, "And this is what a slave who pleases her Mistress gets as a reward." I leaned forward, taking her swollen clit into my mouth and beginning to suck her luciousness, tasting her arousal as my fingers penetrated her dripping pussy. In our years together, Shari had never reached total orgasm so quickly. My mouth had barely squeezed her, my fingers had barely entered her as she began bounce on the chair in a screaming climax. She experienced the strongest, most intense orgasm that I had ever seen her feel. She held my head to her pussy as I sucked her orgasmic clit deep and hard. I continued to pleasure her until she begged me to stop, falling backward with her chest heaving in an effort to fill her body with the air she needed to recover from the intense feelings.

As she recovered, I took her by the hand and led her to our bedroom. I pulled down the bedspread as we slipped under the sheets. I pulled her close to me and held her tightly, "Thank you for coming on this vacation, my friend and lover. You seemed to enjoy the first hours of our time here. Thank you for that exciting encounter."

She cuddled against me and responded, "Yes Mistress, I'm here to please you this vacation. I'm enjoying this. Perhaps we should nap before I continue my duties as your slave." And with that, with both fell asleep.