MaidSally Episode 02

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A shopping trip to Hollywood turns into back room sex.
6.8k words
4.55
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5

Part 2 of the 2 part series

Updated 09/21/2022
Created 11/24/2010
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As I explained in my first episode, I am a kept Cross dressing Maid-servant for my Master who I also refer to Mr. G. (or G). My Master provides for me and makes my life comfortable. For this, I provide him with a willing and compliant servant. Master keeps me quite busy with daily chores and things and he uses me as he wishes. Sometimes he lets others use me. Sometimes he is included, other times he simply sets up the circumstances and instructs me to perform. At some point, I will explain how my unique servitude came about, but that will be in a later episode. Right now, I want to tell you about one of our unique outings to Hollywood.

Mr. G. decided one Tuesday morning that I could use a few more exciting and fun outfits. He said we would go shopping in Hollywood which was a favorite place for us to get the things he liked me to wear. He preferred weekday mornings, as the stores were quiet and we could be much more decadent in our behavior. He told me to dress for a shopping trip. This included dark thigh-hi stockings, with a black garter belt, and very shear panties that would not hide my nice surprise. Also Master picked out a very shear black bra that would provide a very reveling look of my expensive but fake breast enhancements. Master would not allow me to have surgery to get implants, as he said he wanted me to be able to be a man on occasion also. In fact sometimes he would use me in boy mode to join him with a female or a couple. He also forbid me from any kind of hormones as he wanted my perfect cock to keep working and remain the nice size it was and he was afraid the hormones would affect it.

I covered my undergarments with a short black wrap-around dress. The dress was the type that tied after wrapping one strap through the other side, and overlapping the two sides. The ties went in the back and were done in a simple bow. The dress was quite short as I had modified it per masters instructions after we purchased it. One thing master insisted I had learned to do right away was to sew, as he could have me modify or make things more decadent that what we could sometimes purchase. I had shortened the dress by several inches and had cut back the inside vertical seem at a more severe angle so that now the way the dress wrapped , it had a tendency to leave a reveling gap up my left leg that would usually cause the lace of that stocking to show when I walked or moved about. I then put on calf high black boots, and my daytime wig which was a black/brown mix of hair that was shoulder length.

I got ready, and after Master looked me over and gave me his approval we got into the car for the short drive down the hill into Hollywood. Master told me to drive. He liked to watch my legs work the pedals of his Camaro convertible. The car was a stick shift, and it was impossible for me to work both pedals without my dress parting considerably and showing my stockings and garter straps. Anyone observant person who came up along the right side would get quite a show. Of course Master would instruct me to slow down or speed up if someone interesting was along side. This is what happened on this outing.

As we drove along Santa Monica blvd an SUV slid along side. The driver who appeared to be in his late 40s glanced over and did a double take when he saw my short dress parted up one leg clear to my panties. Mr. G. smiled at him, and me, and then placed his hand on my right leg. We stopped at a signal and the SUV pulled up short to keep his line of site into our car. As we waited for the signal, Master caressed my right leg delicately and moved the cloth of the dress further and further apart. Of course, I would have been scolded and punished if I did anything to cover up or stop Master. His spankings can be quite painful depending upon the crime I commit. He even kept a paddle in the trunk of each car just in case I needed some discipline while we were out. More than once we had found a secluded place to park so Master could dish out some swats for some minor infraction. On an earlier drive one day I had got us lost, and Master told me to pull over in an alley that was off a street where many of the day labors hung out near the home improvement store. We parked, he told me to get out and go to the trunk for the paddle which I did without hesitating. I was wearing a see through summer dress that did nothing to hide my panties, bra and stockings. That day it was very hot out, and my dress was sheer and small.

As I moved from the car, a dozen or so of the laborers took notice and turned to watch. I opened the trunk and leaned way in lifting my short dress above my panties in order to retrieve the paddle from inside the trunk. Master came around, closed the trunk and took the paddle. He then told me to lay over the right side of the rear of the car. We were about 20 yards down the alley and other than the laborers at the entrance of the alley, we were secluded completely. I did as instructed. The crowd at the end of the alley was entranced now. I had my hands out on the trunk. Master reached under my dress and pulled my panties down off my bottom. He rubbed my bottom nicely for a few seconds and then he slammed the paddle down hard on my ass. I jumped with pain. The laborers all squealed out a bunch of things in Spanish. Master slammed down again and again. The observers where really yelling and even clapping now. More of them came to watch.

Some started moving in our direction, but Master simply put up his hand in a stop gesture, and they all froze and moved no further. Master did have a very commanding appearance. After about 15 hard swats, Master told me that should be sufficient to learn my lesson. My cock had become rock hard during the spanking. Master pulled me up from the trunk and turned me facing our audience. My cock was hard and un-restrained as my panties were down around my knees. Master told me to take off my panties slowly, which I did. I lowered them and stepped out one leg at time clearly flashing my manhood to the observant men and handed them to my Master.

"Ok Sally, that was exciting, we better go before someone gets too excited. You drive."

I slowly strode around to the left side of the car with my dress open and my hard penis sticking out. I turned facing the men, and then seductively got in the car. Master got in the right. I fired up the convertible and as instructed, I made a 3 point U-turn and we headed back to the entrance where the growing crowd of observers remained watching us. There were about 20 young men now. Many were rubbing their crotch, obviously excited from the show. A couple of them even had their own cocks out and were exposing them to us, probably hoping we would stop. But we drove slowly past. They all looked into the car. My dress was up and my cock was sticking straight up almost rubbing on the steering wheel. The comments whistles and hooting and hollering were mostly in Spanish, but it all sounded fine. Master held out the panties and one of the men took them. We moved past the laborers and down the street.

"Master, were you worried back there. What if they attacked us?" I asked.

"They would not do that. Cops are the last thing they want to attract. Were you worried?"

"A little" I replied

"Well Sally, You were sure hard and excited to have been worried too much." Master laughed. "I think I will return here with you on another day and see how far we can take this little game.

We headed down the street, and my cock was still hard. Master told me to take care of it. While he watched, I grasped myself and stroked my cock until I exploded. It only took about 20 strokes.

But back to today's shopping trip. We continued to drive down Santa Monica towards our destination. The man in the SUV worked to keep his vehicle alongside of us. Mr. G. Kept playing with my leg and even slid his hand up over my thin panties and played with my now very erect cock. The tip of my cock started to protrude out of the small panties which were exposed completely as my dress had fallen open completely. At the next stop, Mr. G. had his hand in my panties and wrapped around my shaft when the SUV slid up again. The man was staring into the car as Mr. G. worked my cock slowly up and down.

"Well the man cannot be confused as to me being a cross dresser" I thought to myself. If he liked what he saw, he would keep looking. If he did not like it, he would speed off or turn. He moved along with us for a couple more blocks.

It was still early (11am), but Mr. G. Suggested we stop a little dive bar for a bloody Mary or Screwdriver. He told me to speed up and pull in front of the SUV. I did so, and we turned into a small lot at the bar. I looked in the mirror and saw the SUV continue on. "Oh darn", I thought to myself

I pulled my dress together and tried to relax myself so my hard cock would not be so obvious. We got out of the car and started to the back door of the bar. Just as we reached the door, the SUV reappeared and turned into the parking lot. Mr. G. had his hand behind me and as we got to the door and the SUV driver looked over, G. slid his hand down over my ass and under my dress, lifting it and exposing my ass nicely. We moved into the bar and took a seat on the bar. Besides the bartender, there was only one other older guy sitting at the other end of the bar on the other side of Mr. G. sipping on a Budweiser. The entire scene reminded me of the C. Crow song "Santa Monica Boulevard, and the man could have been William, or Bill, or Buddy,.... I sat on the bar stool and intentionally allowed my dress to slid open exposing legs and stockings again. I knew from experience this is what my master would want me to do.

The SUV driver came in right behind us. He looked around and then moved toward us. He smiled and looked at the stool next to mine.

"You two look like you are having too much fun. Can I join you? My name is Jay."

"Please, sit down. This is Sally, I am G. Can we buy you a drink? We were going shopping, but decided we needed a little refreshment before braving the stores"

We all ordered drinks from the bartender who now seemed to show more interest in this unusual trio of patrons he now had. Mr. G ordered Bloody Mary's for both of us, and Jay ordered a Screwdriver.

G and I turned slightly to face towards Jay as the bartender made the drinks. My left Knee moved until it pushed lightly against Jay's right leg. He did not pull away. I now saw over my shoulder that there was a mirror on the opposite wall that must have allowed the bartender to see what was happening under the bar top. This made things even more exciting. The Bartender was not a bad looking guy either and he introduced himself as Mike.

We got our drinks and G said "cheers" and we all took a sip. G explained that we had some fun stores we liked to frequent that had very sexy and decadent things. He went on to explain that "Sally" was pretty much his girl to do with as he wished.

"Right sally" G asked.

"Of course Mr. G." I replied without any hesitation.

We drank and our discussion turned to my relationship with Mr. G. and how he treated me very well, but expected me to "perform" anytime and anyplace. Jay was quite intrigued. As we talked, Mr. G. forced my chair more towards jay, causing me to cross my right leg over my left. My right foot went under Jays legs and I immediately started to rub my foot along the inside of his calve. Jay reached down and placed his hand on my left thigh. The skirt fell open exposing more leg and stockings. The bartender stood on the other side of the bar and stared at us and the image in the mirror.

We had one more drink, and I became friskier. I leaned closer to Jay and reached over and put my hand on his right thigh and started to caress his leg seductively. My cock was starting to get hard and so was Jay's. I worked my hand to his now throbbing cock and started to rub it through his jeans. Mr. G. asked Jay if he wanted to shop with us. He readily agreed, saying he was not really that busy today and whatever it was could wait until tomorrow.

Then Mike the bartender offered us all a shot on the house.

"Only if you join us" Mr. G. said.

Mike agreed and he made up some concoction and poured it into 4 glasses. He placed them all on the bar, but he then came around to our side. He moved up between Jay and me and reached between us for his drink.

Mike lifted his glass and proclaimed "Here is to my favorite kind of girls. The ones that never get bitchy and always have a nice surprise for you"

I guess Mike had no doubt about my true identity either. He smiled at all of us, but especially at me.

"Thank you Mike" I replied, and I lifted my hand from the large mound on Jay's lap and stroked Mike's chest very smoothly and seductively. Mike placed his hand on my neck and rubbed lightly.

We finished those shots and one more round. We were all buzzed. I needed to use the restroom, so I turned my stool and stood. My skirt caught on the chair back and it pulled open as I stood. My panties and rigid cock were exposed. Mike commented on my condition.

"Wow that looks wonderful" Mike said. "I wish I was not working, I would love to go shopping with you."

Mr. G. answered "It is a little rude Sally that you are such a tease, and then you me and Jay are going to leave poor Mike here while we go pick out some really nasty things for you to try on."

"Yeah, that is not fair at all" Mike said with kind of a whimper while still looking at my panties and semi hard cock that was protruding out one side. While Mike stared at me, Jay had reached over and had his hand on my ass and was rubbing it smoothly. He was squeezing my bottom as Mike whined about being left alone. I still wanted to use the restroom, so asked Mr. G. If I may.

"Of course Sally. Maybe Mike can show you to the restroom so you don't get lost." G chuckled as the bar was so small and there appeared to only be one restroom.

"I will take you sweetheart. If anyone else comes in tell them I will be right back." Mike said with a huge grin on his face. I also noticed that he had developed a huge bulge in his pants also. Not a normal bulge, but a huge bulge that protruded down one pant leg at least 8 inches. It was also throbbing in a very hot and seductive manner.

I moved between Mike and Jay and Mike turned and took my hand and led me to the hallway where the restroom was located. When we got to the restroom, Mike pushed the door open and let go of my hand so I could enter.

"You are going to stay and guard the door right?" I asked seeing there was no lock on the door.

"I will be right here." He replied and he leaned over and gave me a long and seductive kiss on the lips pushing his tongue into my mouth. His deep kiss felt great on top of having and early morning alcohol buzz.

I broke away and moved into the bathroom. It took me a minute or so to allow my erect cock to subside enough to be able to pee. I finished my business and turned to see Mike inside the door. He must have watched me as I stood to relieve myself. His pants were undone and he had his massive cock in his hand holding it out.

"That was rather a site to see someone dressed like you doing that" Mike said as he stroked his rigid cock as I moved towards him. He continued to stroke as I washed my hands. He was leaning against the wall next to the hand blow dryer.

Mike looked at my wet hands and the blow dryer and said "Do you need a blow job now?"

"Yes, but I think you need one more" I laughed.

I put my hands under the low set dryer and moved them around until they were dry and then I moved them to his cock. It was so large it took both of my hands to really cover it. I started stroking him while he kissed me. His cock pulsed with my touch. I slid down and moved my face towards his cock. I kissed the tip a few times and then engulfed what I could into my mouth.

I knelt down and moved my head back and forth taking Mike's 8 inch cock deeper and deeper with each stroke. I kept at it, occasionally stopping to lick the tip or side of his cock, or his balls. He was leaning against the wall with his head back moaning. I noticed the door move open slightly and saw Mr. G. looking in. I kept up with my sucking and kissing. I finally worked the large cock deeper into my mouth and nearly had engulfed all of it when Mike started to shudder. Knowing my Master was watching, I sucked hard as the first streams of cum blasted into my mouth and deep into my throat. I let two large pulses go into my mouth, and then I pulled back off Mike's cock and aimed it into my open mouth so Mr. G. could see the remaining streams of cum stream between my lips. I know how much Mr. G. likes that, so I did the best I could to give him a show.

As the streams died down, I used my tongue to dab up the smaller surges of cum as Mike kept throbbing. I licked and sucked until Mike was done. I left some cum on my lips as I stood up. I moved to Mr. G. and kissed him deeply. He eagerly licked and tasted Mike's cum and he plunged his tongue deep into my mouth gathering as much as he could. My Master was indeed a bi-sexual cum slut himself. Perhaps that is part of the reason he has me around is to help satisfy his desires for cum and cocks. Oh well I don't mind.

Mike and Mr. G returned to the bar while I cleaned up and fixed my makeup. I came out and all three guys were smiling brightly.

"I went straight up to Jay and kissed him deeply and then said "I will make sure you are satisfied, don't worry". Master smiled at my comment to Jay.

Just about then numerous people came into the bar and we said our goodbyes and headed out. Mr. G. told Jay to follow us. He did gladly. We parked at a lot of Hollywood Boulevard and joined up and walked to the first store. I made sure to stroll and sway very seductively as I moved along the boulevard or when moving around in the stores. My dress flowed seductively and allowed my leg, stocking and garter to show most of the time. Many people noticed us and the men all smiled as they walked by. In the first store we went to, we looked around, but nothing (or no one) caught my Masters eye. We move down the street to a much larger store. This store had a big selection of clothing for women and men, and several dressing rooms near the back of the store on the right side. There was some very fun clothing that Mr. G. liked, so he picked out a few things. Jay also picked up a flimsy little dress that he liked, and we added that to the pile. The clerk took us over to one of the dressing rooms and hung the clothing inside. He seemed less than interested, but a male customer that was shopping was watching us closely.

I went into the dressing room and pulled the curtain partially closed. Jay and Mr. G. milled around outside while I removed my wrap-around dress and tried on the first dress. It was a slinky little black dress and I slid it up my body and pulled it over my breasts. I stepped out of the dressing room to show Mr. G. and Jay. It did little to cover my stockings. The male shopper brought some things to the adjoining dressing room and as he passed by he looked intently at me and my two escorts.

Mr. G. commented that the dress was a keeper, so I went back in the dressing stall to try on the next item. This time I intentionally left the curtain open about ½ way. I had just slid down the first dress and was standing there in my panties, garter and bra when the male shopper came out of his stall to use the large mirror. He could not help but see me standing in the room getting the other dress off the hanger. I made no attempt to cover myself or close the curtain. I knew any kind of modesty would surely invoke a spanking later from my master. The man half heartedly looked at his pants in the mirror, and moved back inside his room staring at me intently as long as he could.

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