Disclaimer: SissyAndi stories contain sexually explicit descriptions of consensual and Non-Consensual sexual activity and are not suitable for reading by anyone under the age of 18, or anyone offended by reading such material. These acts include bisexual activity, cross-dressing and other fetishes and perversions. The characters in these stories are fictional. All Stories are the property of the Author. Any feedback would be greatly appreciated. Thanks.
Authors Note: The following story is part of the ongoing saga of Andi, a 15 year old, cross dresser who is 5'9" 130 pounds, long blonde hair and blues eyes.
While it is my hope that each chapter will be entertaining as a stand alone story, I suggest that all new readers go back and read the "Andy And The Team" series, as well as previous entries in the Andi's Adventures Series. They contains a lot of back ground information that will help explain each story.
Andi's Adventures - Part 20
I was sitting by the window of the plane looking down on New York City. I was still very nervous because it was my first time flying. We were on a private jet chartered by Ms. Rhodes.
Ms. Jillian Rhodes was flying her mother to New York to see a heart specialist and to have a series of tests done. Since my mother had been hired by Jillian as a private nurse to take care of the elder Ms. Rhodes, My mother came with her and that allowed me to come along.
It was my first time in a plane, my first time in New York and when we got off the plane we were met by a limousine. Another first for me.
It was Mid-October and it had started to turn cold in New York. I was dressed in a green wool sweater, and black skirt that came to mid thigh. I had on a pair of thick white tights and a new pair of black boots.
The limo took us to a very fancy hotel that was not to far from the clinic where they were going to perform the tests on Jillian's mother. It was around 1:00 P.M. when we checked in.
They took our luggage up to the penthouse suite. It had two bedrooms, one for Jillian and one for me and my mom. I knew I was out of my comfort zone but I think I really liked being around people who had money.
Mom said that they were going to take Jillian's mom to the clinic and get her checked in so she could rest up before they started running tests the next morning.
Mom said I did not have to go along. She also said I could look around the hotel but I had to promise to stay out of trouble, and under no circumstances was I to leave the hotel.
Of course I promised Mom I would be a good girl. ____________________________________________________________
After everyone left and I was alone in the hotel room, the first thing I did was call Marcus and let him know that we made it to the hotel safely and to let him know I missed him.
I was telling him how fancy the hotel was and then I mentioned how much fun we could have in a hotel room. Marcus said he would love to spend a weekend in a hotel room making love but that he was not so sure what she would have to say about it.
Mom was cool about my relationship with Marcus but I was not sure she would let us do that any time soon.
I told Marcus I loved him and he told he loved me and I hung up the phone. There were a few pamphlets laying on the coffee table in the common room of our suite. I thumbed through them for a few minutes.
I decide to venture out of the hotel room and look around. There was a cute older man in the elevator with me as we rode down to the lobby. His cologne smell so good and he looked to be in good shape, 4 or 5 inches taller than me with graying hair and he wore glasses. He looked great dressed in a khaki pants and blue Izod shirt.
I smiled at him and he said Hi, we chatted until we reached the lobby. he said he was here on vacation with his family and I told him I was with my mom and it was our first time in New York. As we exited the elevator He told me I was a Cutie and for me to have a great time in New York.
I loved the attention I was getting lately, especially as my breasts started grow because of the hormone treatments, I had developed a firm set of 32 B breasts. My nipples had also become so sensitive. Even my hips were also starting to develop into the hips of a young woman.
I headed for the shops on the ground floor to do some window shopping. There was this very nice dress shop and there was a beautiful black velvet dress on display.
I had to go in and check it out. Oh my god that dress was almost $450. I loved it and wanted it bad but there was no way my mom was going to let me buy it, no matter how much money she was making working for Jillian.
I looked around the store spotting several dresses I liked but my eyes always went back to the dress in the window. Finally I decided to check out some of the other shops.
I worked my way down the line of shops and was heading back when I passed the dress shop again. I stopped to admire the velvet dress one last time.
I heard someone say,"that dress would look great on you." I looked up and it was the man from the elevator. I told him thank you but I was just looking. He asked me where my Mom was and for some reason I told him the entire story about her being a private nurse and that they were at the clinic right now.
The man introduced himself as Duncan, and told me that his wife and daughter were off on a shopping trip and he decided to hang around the hotel today.
I told him my name was Andi and it was nice to meet him. He asked me if I wanted to get a cup of coffee or a milkshake with him. I started to say no but Duncan had the friendliest smile so I agreed.
We went to the coffee shop in the corner of the hotel, we sat and sipped our drinks. I felt so sophisticated sitting in a coffee shop in New York talking with a handsome older man.
Duncan talked about his wife and daughter, she was just a year younger than I was and she was a cute blonde like me, her name was Karen. As we finished our coffee we took a walk through the hotel and ended up back at the dress shop.
He took my hand and said come on and led me into the dress shop. I asked him what he was doing and he said he decided to buy that dress for his daughter.
He asked me what size I wore and I told him. He told the sales lady that he wanted to buy two dresses like the one in the window.
I asked him "two?" he told me of course silly I am going to buy one for Karen and one for you. I told him that was nice of him but I could not let him do that.
The sales girl had already boxed the two dresses and was running his credit card through the reader. She thanked him for his business and we left the shop.
He asked me what floor we were staying on and I told him the top floor, that we were in the penthouse. He told me that they were staying on the 14th floor. As we got on the elevator there was an older woman with us.
She got off on the fourth floor and as soon as the doors closed Duncan pushed me against the back wall of the elevator and started kissing me. I tried to fight him, well at first, but Duncan was a great kisser.
When we reached the 14th floor and the doors opened Duncan finally let me go. He took my hand and was pulling me in the direction of his room. I told him I had to get back to my room before Mom got back from the clinic.
Duncan would not take no for an answer. He told me he wanted to see me in the dress and I was going to model it for him. I reluctantly agreed to put it on for him for but only for a few minute then I had to leave.
They had a simple room with two beds. I went into the bathroom to change. The dress was a little tight, it showed off ever curve of my body. I thought I looked hot but I was not sure that Duncan would think so.
I smoothed the dress down one more time and went back into the room where Duncan was waiting. He had a very expensive camera in his hands and he asked if it was ok to take a few pictures.
I told him Ok and he started snapping pictures and telling me to walk back and forth. To turn around and look over my shoulder. I figured he would try to talk me into taking off the dress but instead he put his camera down and started kissing me again.
As we were kissing he took my hand and put it on his crotch, I could feel his hard cock through his pants. I squeeze it and felt it jump. Duncan had his hands on my ass squeezing it as we continued to kiss.
Duncan broke the kiss and asked me if I would do something for him, it was not what I was thinking as he went to a bag beside the bed and asked me to put on a pink shade of lipstick and then he asked me to put my long blonde hair up in a ponytail.
I went to the bathroom and removed the cherry red lipstick I had on and applied the pink lipstick. I took a rubber band and put my hair up.
Duncan was ready with the camera and started taking more pictures. He said that he wanted just one more thing. He asked if he could pretend I was his daughter and call me Karen.
I was having sex with my mother on occasion so what was so weird if he fantasize about sex with his daughter.
Duncan put down the camera and sat on one of the beds. He watched my reaction as he unbuttoned his pants and pulled down the zipper. He had a nice cock, about 8 inches long and he was uncircumsized, that was the first one I had ever seen.
He patted the bed beside him and said "come here Karen."
I went and set beside him and he told me "no need to be nervous sweetheart, Mom will not be back for hours."
He took my hand and put it on his cock. I wrapped my hand around his cock and slowly started to work my hand up and down.
Duncan was already moaning, he kept telling me what a good job I was doing. I decided to get into character. "Can I kiss it Daddy? Please?"
"Oh God yes Karen, I want you to kiss it for me." I leaned down and kissed the tip. I stuck out my tongue and licked the shaft.
"Oh Karen you do that so good, have you been doing this to your boyfriend?"
"No Daddy, this is my first time, I have always wanted you to be the first one I suck." With that I took the head of his cock into my mouth. I started working my mouth up and down the shaft and felt Duncan playing with my ponytail.
I heard him saying "Oh Karen, yes baby girl that feels so good. Suck Daddy's cock."
I looked up to see a flash, he had taken a picture of me with his cock in my mouth. Oh well it was not the first time. I continued to bob my head up and down his hard cock.
I squeeze his balls as I sucked just the head. He was thrusting his hips up and trying to force his cock deeper into my mouth.
"Oh baby that feels so good, you suck cock better than your mommy."
His cock was throbbing by now and I knew it would not be long before he would cum. I tried to pull back but he had his hand on the back of my head forcing me to keep his cock in my mouth.
"Oh god Karen here it cums, swallow daddy's baby juice."
And did he ever cum. I swallowed and swallowed. I was proud of myself, I did not lose a drop. When I let his cock slip from my lips he pulled me to him and kissed me. As we continued to kiss, my cell phone rang. I struggled to break the kiss and Duncan reluctantly let me go.
It was my Mom calling to tell me that they were heading back to the hotel and for me to meet them back at the room because we were going out to eat.
I told Duncan I had to leave and he asked me how long we were going to be in New York. I told him that we would be here for the next three days.
He asked if maybe we could get together again and I told him I did not know if that would be a good idea, but I gave him my cell phone number.
He kissed me again and walked me to the door. I almost forgot that my skirt and sweater was still in the bathroom and I was wearing the dress Duncan had bought me.
I quickly grabbed my clothes and left the hotel room. ____________________________________________________________
Back in our penthouse suite I was admiring how I looked in my new dress and decided to wear it to dinner with Mom and Jillian.
I redid my makeup and was brushing out my long blonde hair when Mom came in to change. She told me I looked great and asked me where I got the dress, that she had never seen it before.
I thought quickly and said that it belonged to my friend Cindy and she let me borrow it for our trip to New York. I was glad she let the subject drop after that. ____________________________________________________________
Jillian took us to a wonderful french restaurant. Since she had rented a limo and neither her or my mom had to drive so they drank a lot of wine over dinner. They also flirted openly.
Mom is 5'2" tall, 120 pounds, short red hair and dark green eyes, her 34 B breasts were on display in the little black dress she was wearing. Her sexy legs looked great in black hose.
Jillian is very tall brunette, she has long shapely legs, and a bust that had to be 36 D at least. She was in great shape for a woman in her early 50's. She also has very sexy brown eyes lurking behind designer glasses.
I was use to only seeing Jillian in tailored business suits. Tonight she was wearing a dark blue dress that was so short that if she was not careful you could see her stocking tops when she moved.
I knew they had been lovers for a while now but I was still surprised to see Jillian lean over and kissed mom. Mom hesitated but then kissed her back. Jillian looked at me and winked.
They both were a little tipsy as we got back into the limo. Mom was on the right, I was on the left, and Jillian was sitting between us. I thanked Ms. Rhodes for letting me come to New York with them.
She said I was welcome and that I was turning into a very beautiful young woman and that I was almost as sexy as my Mom. With that she started kissing Mom again.
I did not really know what to do, I mean it would be rude for me to just sit there and stare as they made out. I jumped as I felt Jillian's hand on my thigh.
She broke the kiss with Mom and told me it was time that she let me in on a little secret.
Jillian explained "Your Mom does not just work for me, she and I are lovers. Not just lovers but your Mom is my sex slave. She does whatever she is told to do."
She looked at Mom and said "isn't that right my little whore?"
Mom looked down and replied in a whisper, "Yes Mistress."
"I love your Mom but I also own her." Jillian then told Mom to get on the floor of the limo and start kissing her feet and calves.
Mom did it without hesitation. While mom was doing what she was told, Jillian started stroking my thigh and then kissed me.
Jillian was exploring my mouth with her tongue as she groped and squeezed my sensitive breasts.
Mom had worked her way up to kissing and licking Jillian's thighs when we pulled into the parking deck of the hotel. We all had to rearrange our clothing before we got out of the Limo.
The elevator was crowded as we rode it up toward the penthouse. The further up we went the fewer people were in the elevator. Four floors from the top the three of us were finally alone.
Jillian reached out and pressed the button stopping the elevator. She turn to us and told Mom to strip to her underwear. I watched as mom immediately started to undress.
Mom slide the straps of her black dress off of her shoulders and let it fall to the floor. As Mom bent over to pick up her dress Jillian reached out and slapped her ass hard. Mom jumped and let out what is best be described as a yelp.
Jillian then told Mom to take off her bra and give it to her. Moms bra hooked in front and i watched as she undid it and let her breasts become exposed.
I could not believe we were in an elevator in New York and Mom was standing there in nothing but black panties, pantyhose and heels. Jillian took something out of her purse and handed it to Mom.
"Put it on!" Jillian Ordered.
Mom lowered her head and said "Yes Mistress." It turned out to be a collar with the word SLUT written on it.
Jillian started the elevator again and when we reached our floor she pushed Mom out into the hall ahead of us. I followed Jillian out of the elevator and just before the doors closed Jillian threw Moms bra on the elevator floor.
Jillian went first and led us to the door of our suite. It was unreal following my Mom down the hall of a exclusive hotel while she was topless.
Jillian opened the door, took my hand and pulled me into the room. She told mom she could only come in if she crawled through the door. Mom quickly fell to her knees and crawl across the thresh hold.
I figured it was time for me to excuse myself but Jillian stopped me, kissed me lightly on the lips, then asked my Mom if she had any objections to having me join them tonight.
I heard Mom say No Mistress. We went to Jillian's bedroom with Mom crawling behind us. When we got to the bedroom Jillian gave Mom permission to stand.
Jillian then ordered Mom to help her undress. Mom went to Jillian and started unbuttoning her dress. Mom then slide the dress over Jillian's shoulders and pushed it down to the floor. Mom got on her knees as Jillian stepped out of her dress.
Jillian ordered Mom to kiss and lick her high heels while she was down there. I was watching in astonishment as mom did everything she was told. After Mom had cleaned Jillian's high heels Mom had to undo the strap and remove each shoe.
Mom then was made to remove Jillian's panties. After kissing and licking her cunt for a few minutes Jillian pushed mom away and told her to stand up.
Mom then had to remove Jillian's bra exposing her very big and incredibly sexy breasts. Mom leaned in and kissed each nipple.
Jillian pulled a chair beside the bed and sat down. She then instructed mom to help me remove my dress. I held my hands overhead as Mom took the hem of my dress and lifted it up.
I noticed Jillian was rubbing her pussy as she watched us. Mom had to get on her knees again to remove my boots, then she hooked her fingers into my tights and pulled them down my leg.
As Mom was doing that I had reached back and undone my bra, freeing my small breasts. Jillian told me to lay down on the bed. There was no doubt who was in charge and she was directing everything that we were doing.
I laid down and Mom was told to join me, Jillian told Mom to pull my panties down and to lick my little cock. Mom looked at her for a second then did as she was told. I felt her tongue start to lick my soft cock.
Since I have been on hormones my cock did not get hard as often as it did before. Mom took my limp cock into her mouth and started sucking me. After several minute it had grown hard.
Jillian told mom to continue to suck me, she wanted Mom to make me cum in her mouth. I was cupping my breasts and pinching my nipples as Mom was working her mouth up and down the shaft of my cock.
Mom must have sucked me for over 20 minutes but I eventual shot a small load of cum into her mouth. She had to open her mouth and show Jillian before she was allowed to swallow.
Jillian stood up and got a bag from inside her suit case. She told mom to keep her ass in the air. She took out a paddle and started spanking Mom hard. Mom would moan with each whack to her ass.
Jillian then took out a medium size butt plug and she was generous enough to put lube on it before forcing it into Moms ass. She had not given me any instructions so I just laid there and watched.
Jillian ordered Mom to get off the bed and sit in the chair. Jillian went back into her bag and brought out four pieces of rope. She proceeded to tie Moms legs to the legs of the chair.
She then tied her wrists to the arms of the chair. She took what looked like an eight inch vibrator and pushed it into Moms pussy. It buzzed loudly as Jillian set it on high.
Mom was tied to the chair and she was moaning loudly. She was squirming as the vibrator was working its magic.
Then Jillian turned to me and told me it was my turn. Honestly I was kind of scared of what she might do to me. She told me to get onto all fours on the bed.
I did as I was told and soon felt the sting of the paddle. She landed more than 10 blows to my ass and it was stinging badly. Finally she set the paddle down and went back to her bag.
I was looking back over my shoulder as Jillian worked the harness of a strap on up her legs. Attached to the harness was a huge fake cock. It was almost as long as Marcus's 10 inch monster and it looked bigger around.
Jillian stood in front of Mom. She pulled Moms head down and pushed the "cock" into her mouth. she was forcing more and more into Moms mouth. When she had the cock nice and wet Jillian took her used panties and shoved them into Moms mouth.
Jillian climbed back onto the bed and lined it up with my ass hole. She pushed the tip into my ass. Mom was struggling as she watched Jillian do this to me, I had my head down preparing for the pain I knew was going to come.
Jillian continued to apply steady pressure as she forced more and more into my butt. I felt stretched wider that I had ever been before. Finally I felt Jillian's thighs against my butt and knew that she had the entire length in me.
Jillian started slapping my ass with an open hand. She would slowly pulled the cock back until just the tip was in me and then she slammed it back into me hard and deep.
Mom was moaning from the pleasure that she was getting from the vibrator but her eyes were glued on what Jillian was doing to me. While she was driving the cock in and out of me, Jillian started raking her long fingernails up and down my back.
Every time Jillian drove her cock into me the other end would rub against her clit. She was fucking me hard and faster now. My ass was stretched and my ass cheeks were stinging from the spanking. My back was burning from all of the scratches.
Jillian was breathing hard and I knew she was close to cumming, that is why I was surprised when she pulled the "cock" out of my ass. She told me to lay on my back as she was unsnapping the strap on and taking it off.
I had no idea what Jillian had in mind until she climbed on the bed and straddled my face.
"Eat me bitch!!!!" Jillian screamed at me as she lowered her wet dripping pussy to my mouth. She was grinding her cunt all over my face as I licked her pussy. I locked onto her clit and licked it repeatedly. I swirled my tongue around it and then started sucking on it.
"That's it slut, suck my clit, make me cum you nasty little whore."
She had no sooner got the words out of her mouth when she started cumming hard and flooding my mouth with her juices. I licked as fast as I could but she was cumming so much it was running down my face.
Jillian finally climbed off of me. I was gasping for air. Jillian reached down and caressed my face.
"With a little work and practice you will be able to eat pussy as well as your mom does."
For some reason my face burned from embarrassment.
Jillian told me that I was dismissed and I could leave but first I had to kiss Mom goodnight. I removed the panties from Mom's mouth and gave her a quick kiss on the cheek. Jillian told me to give her a real kiss.
Mom was still tied to the chair so I took her face into my hands and kissed her deep and passionately letting her taste Jillian's juices on my tongue and lips.
I picked up my dress and lingerie and headed to my room. Mom never told me what else happened that night but I could hear her moans and cries of passion late into the night. ___________________________________________________________
Mom decided to take me shopping the next day and as we were riding the elevator down to the lobby when it stopped on the 14th floor. Duncan and what had to be his daughter got into the elevator with us.
Duncan moved to where he was standing off to the side and kind of behind me. His daughter was standing in front of him and Mom was on the other side of me busy looking at a map.
I almost jumped out of my skin as I felt Duncan start to grope and squeeze my butt. He kept feeling my ass until more people got on the elevator a few floors down.
In the lobby they went right and we went left, that was the last time I seen Duncan. Sometimes I wonder just how many times he has looked at the pictures he took and remembered the day I pretended to be his daughter and sucked him off. I bet he has cum many, many times reliving that day and masturbating.
More to come, especially if I continue to get positive feedback.