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 14 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 12
My freshman year finally came to an end and I was out for the summer. Too bad I had to spend my first two weeks of summer vacation being grounded.
Mom finally caught me dressed up and some of my past activities were exposed. She knows I have been dressing in her clothes since last October. When she caught me I was coming in from a day of fun with the boy of my dreams. So Mom knew I had been sexually active with other boys but she had no idea to the extent I had been active or I would have been grounded for life.
During my grounding I would dress up in the morning as soon as Mom left for work, Do all the house work and prepare dinner for me and my mom. I would change back to my drab boy clothes before mom got home from work.
During dinner each night Mom and I would talk, we would discuss different aspects of my "lifestyle". I think she was coming around to accepting me as Andi instead of Andy.
One day during the second week, Mom called home. She informed me that she had been wrestling with it, but she thought she was ready to meet Andi. If I was ready she wanted me to dress as Andi for dinner that night. Before she hung up she said, "Andi I want you to be as pretty as you can be, so feel free to use my makeup and my clothes if you need to." __________________________________________________
My heart was beating fast with excitement as I finished dinner and knew it was time to get dressed for my Mom.
I went to her closet and started looking through it to see what would be appropriate. I had kept my word and had not gone through my Moms things since she had caught me.
I decided since it was for my Mom and I wanted to make a good impression that I would dress conservatively for tonight. I chose a black pleated skirt that came to just above the knee. I found a simple white blouse with ruffles and buttons down the front.
I went to my room and found my white bra and panties and laid them on the bed with my skirt and blouse.
I started to fill the bathtub up and pour some sweet smelling bubble bath into the water. When the tub was ready I ease myself into the tub and let my body soak for a minute. A nice long bubble bath is infinitely better that a quick shower, but I knew I had to hurry if I wanted to be ready for Mom.
I washed my hair, then started shaving my legs. Luckily I had very little hair on my arms and legs. I got out of the tub and toweled myself off. My whole body tingled.
Since I was out of school I had started keeping my fingernails and toenails painted. Mom had noticed but had not said anything. I slide on my panties and fixed my bra in place. Stuffing the cups with old pantyhose.
I dried my hair and brushed it out. I debated leaving it down or putting it in a ponytail. I decided on the ponytail. Next I did my makeup, I decided to keep it simple, a light touch of blush and some cherry red lipstick. I did not even use eyeliner this time. I wanted to look innocent for my Mom, not the slut I like to be at times.
After I finished with my makeup, I opened a new pair of black mist pantyhose and put them on. MMM my legs felt so smooth and sexy.
Oh lord I was starting to get hard. I definitely had to do something about that. I looked at the clock, it would have to be a quickie. I sat on the bed and slide my pantyhose and panties down to my knees.
I started daydreaming about being with Tony, who I had started thinking of as my tall hunky black love god, and stroking my "clitty". As the pleasure spread through my body it did not take long before I started to cum.
I started to reach for some tissues but decided to lick my fingers clean, savoring the taste of my own cum. I was truly becoming a cum slut.
After a few minutes I started dressing again. I fixed my panties and hose back into place. Shimmied into my skirt and zipped it up. I finished buttoning my blouse and tucked it in. I checked myself in the mirror and decided I looked like an innocent 14 year old angel. Mom would approve.
I had just finished setting the table as Mom came through the door. I hollered to her to take a seat on the couch and I would bring her a glass of wine.
I grabbed a glass and poured some wine, I took a quick gulp or two to calm my nerves, refilled the glass, then headed for the living room to see how my mom would react.
As I entered the room Mom was sitting back on the couch messaging her feet. As a nurse she spends all day on her them. Mom looked up and for what seemed like an eternity we just looked at each other.
Without a word Mom smiled and stood up, taking me into her arms and hugging me.
"Andi you look beautiful." then she started crying and said "I always wanted a daughter, but your Dad said we could not afford another child."
She took the glass and started sipping her wine and said she was starving, lets eat. All through dinner she was looking at me and smiling.
As we talked Mom kept complimenting me. telling me how pretty I was, what great taste I had in clothes, how they complimented my figure and made me look older. She was trying hard to make me feel good about myself, but I think she actually meant most of what she sad.
After I finished washing the dishes and putting everything away I went to join Mom on the couch. She again told me what a pretty girl I was.
Then she said she wanted to try something and told me to turn around. I turn to where my back was to Mom and I felt her take the rubber band out of my long hair and let it fall free. I was not sure at first what she was doing. When she was done she told me to go look in the mirror and tell her what I thought.
Oh My God, she had fixed my hair in a french braid and It looked really, really good on me. I ran to her and hugged her tight. Thanking her for doing such a great job.
She said she would teach me to do it myself if I wanted to know how, I said yes of course I wanted to learn.
She told me that she thought she would be comfortable with me being a girl around the house. She was still not comfortable with me going out all dressed up, but if I decided to leave the house to please be very careful and stay safe.
I promised her I would be extra cautious in and out of the house and we hugged again and said good night.
The next night when Mom came home, I was dressed in a simple black dress with a creme colored bra and panty set. I also had on black hose and heels.
Again I brought her a glass of wine as she got comfortable on the couch. Things were more relaxed tonight since we were both adjusting to me openly dressing around her.
She continued to ask me questions about every aspect of my cross dressing. Most questions I answered honestly. On some questions, while I tried not to lie I did not answer them in full. Again she told me if this was what I wanted, all she asked is that I be extra careful and stay safe.
That night when it was time for bed she called me into her bedroom. She told me that every girl deserved something special to sleep in and that she had went shopping during lunch and she had a surprise for me. Mom then handed me a gift box. As I opened it I seen it contained a modest red and black knee length nightie with spaghetti straps and matching panties.
I was crying as I hugged Mom and thanked her for everything.
That night when I slipped under the covers in my new nighty, I felt better about things then I had in a long time. I sleep well that night and dreamed about being the girl of my dreams and being with Tony. ____________________________________________________
I had called Tony a couple of times since school had ended, but he never answered and I was getting tired of leaving messages on his answering machine. I knew I could not see him for a few weeks but I wanted to at least hear his voice.
On the next to the last day of my grounding, Tony finally answered the phone. I started out trying to flirt with him and was asking him how he was and what had he been up to.
I got the feeling something was wrong. Eventually he told me that he did not want to hurt me, but he had some bad news. He was leaving the next day to spend the summer with his Mom in Ohio and from there he was going straight to college, he was reporting early to the University of Tennessee to began football practice.
He said he had really enjoyed the past few months and he was sorry for it to end this way. He then told me to take care of myself and maybe he would see me around some time. Then he was gone and I was devastated.
I cried all weekend. Mom asked me what was wrong, I broke down and told her how I felt about Tony and that he was going away. I know she did not approve of Tony and I thought I could detect a look of relief on her face.
Being Mom, she did not voice her relief but held me in her arms as I cried and told me that it would all be alright.
Even though my grounding was over I stayed at home for days. I moped around the house and did not even dress up on some days.
I called my friend Cindy and poured my heart out to her. She listened and let me ramble on about how unfair everything was and how bad I felt. Finally she told me it would get better and she had an idea as to how to cheer me up.
She said that she was free on Friday and we needed to have a girls day. We would leave early, go shopping, maybe eat lunch, then shop some more. I said I was not sure if I was ready but she kept on until I agreed.
Jamie called me and asked if I had any plans for Friday. I had told him about Cindy and I wanted him to met her and her to met Jamie, so I invited him to go shopping with us. He was still not confident enough to go out dressed so he declined. ______________________________________
Friday morning I dressed in all black. Black lace bra, lace panties, a black garter belt and black hose with a seem up the back. 3 inch open toed black heels. A black skirt that came to my knee. I completed my outfit with a black silk blouse that I borrowed from my Mom.
I put on my makeup and applied a deep red shade of lipstick. I braided my hair like Mom had taught me and I thought I had did a good job.
I threw my money, some tissues, and some lipstick into my purse and headed out. I caught the bus and was at Cindy's front door by 10 A.M. _____________________________
Cindy is a beautiful Asian cross dresser. 19 years old, 5' 3" or 5' 4" tall. Really slim, gorgeous eyes and short black hair. I met her in a department store and we became quick friends.
When she opened the door she was dressed so very sexy. She had on a green dress, it had a plunging neckline, showing off modest cleavage. her legs looked incredible in black hose and 4 inch pumps. We kissed like old girlfriends and my spirits were already lifting.
We headed for the mall first. Cindy and I was going from store to store, trying on dresses and cute skirts. Still neither of us had purchased anything yet. We were terrible, we flirted with every guy that looked our way.
After the mall we went to a nice Italian restaurant for a scrumptious meal. I could feel Cindy's foot rubbing my calf and thigh as we ate.
I think it was a combination of Cindy's foot, flirting with guys all morning, and the fact that I had not had sex in over two weeks, but my little "clitty" was getting so hard.
After lunch Cindy took me to a store called, "Naughty Nancy's Lingerie". God I was in heaven, I had never seen so much Satin, silk and lace before in my life. I wanted one of everything and one in each color.
I pick a sexy white corset and tried it on. Cindy told me it looked like something I would wear on my wedding night. then she added "if you were a virgin" and we both started giggling.
We looked around some more and I found what I wanted. It was a pink teddy, with lots of lace and a crotch with snaps. It included frilly garters and lace top stockings. Cindy told me she had some pink heels that would go good with that outfit. I had to have it.
Cindy purchased a black body stocking and a red hot see through nightie. the nightie included black panties with red hearts on them. It also came with a sexy short black robe.
I decide to buy Jamie something special, so I got her a teddy like mine but in blue.
As we were leaving the store, I called Jamie to see what he was doing. I invited him to meet us at Cindy's apartment. I knew he wanted to so I kept at him and he finally agreed. I gave him the address and said we would be there in 20 minutes.
Cindy and I arrived back at her apartment and she said it was a special day and she broke out the liquor. She fixed us booth a coke and rum. She said she had made mine weak but it still took my breath when I took my first sip.
By the time I finished my first drink I could feel the warmth throughout my body. Cindy and I decided to surprise Jamie so she went into the bedroom and I went into the bathroom to change into the lingerie we had purchased.
When I seen Cindy in red I just stood and stared. She was beautiful. I had to kiss her. I pulled her into my arms and we started kissing each other. MMMM her lips tasted so good. I had to squeeze that cute butt at least once.
We were kissing and caressing each other when we heard the door bell ring. Cindy looked out and said it must be Jamie. Jamie is 5'11", has black curly hair, he is kind of skinny but has a nice smile and when hard. his cock is 6" long.
We opened the door and pulled him inside. Cindy grabbed Jamie and forced her tongue into his mouth. Jamie melted into her arms. Finally they broke the kiss and I guess I was kind of jealous because I pulled Jamie into my arms and tried to kiss him more passionately then Cindy did.
When we broke the kiss all Jamie could do was look from me to Cindy and say Wow that was hot. I introduced Cindy to Jamie and Jamie to Cindy.
While Cindy went to get Jamie a drink I told him about how much fun shopping with Cindy had been and that he should have went with us. I then told him I had gotten him a present.
Cindy gave Jamie his drink and then she made a toast to friend and fun times. After a few minutes of chatting and sipping our drinks I took Jamie's hand and we led him to Cindy's bedroom.
I gave Jamie his present, he opened it, hugged me and told me how beautiful it was. Then he went into the bathroom to put it on.
When Jamie came back into the room, Cindy and I were kissing and caressing each other again. Jamie came up to us and kissed me gently on the lips and told me thank you again.
He then pulled Cindy to him and started kissing her lips, her cheek, her chin. I came up behind Cindy and started nibbling on her ear.
As Jamie slide the straps of Cindy's red nightie off of her shoulders and down her arms, he was kissing Cindy's neck and kissing her way down to Cindy's breasts and nipples. I started kissing Cindy's bare shoulders, licking the soft skin between her shoulder blades.
I heard Cindy moaning as Jamie went from one to the other nipple, kissing them, sucking them, and biting them. I continued to kiss my way down Cindy's back as I seen Jamie get on her knees and started licking Cindy's clit through her lingerie.
Jamie slide Cindy's panties down and started kissing and licking Cindy's clit. Jamie took it into her mouth and was sucking it for all she was worth.
I decided to do something I had wanted to try for a long time. I finished sliding Cindy's panties down and had her step out of them as Jamie continued to suck her.
I kneeled behind Cindy and started placing wet sloppy kisses all over her cute ass. Jamie was trying her best to get Cindy to cum, I spread her cheeks and licked deep. I started swirling my tongue round and round rimming Cindy's delicious ass.
I began tongue fucking Cindy's cute butt as Jamie was working her mouth up and down Cindy's throbbing clit. I could feel Cindy's whole body shiver as Jamie and I both worked on her. I knew she could not hold out much longer. Pretty soon I felt her ass clench and she stiffened then let out a loud moan as she started cumming in Jamie's mouth.
As Cindy started to relax Jamie lead her to the bed. As we watched Cindy climb on to the bed, Jamie kissed me and we shares the taste of Cindy's ass and cum with each other.
Jamie and I joined Cindy on the bed. I positioned myself where Cindy could lick and suck my clit, while Jamie got behind Cindy and slowly started to ease her cock into Cindy's ass. All my licking and rimming had lubed Cindy's ass nicely and Jamie had very little trouble working her 6 inch sissy cock into Cindy.
Cindy was doing a really good job sucking my little clitty as it grew hard and felt so good in her mouth. Cindy was moaning around my Clit as Jamie was working her cock in and out of Cindy's ass.
I felt Cindy reach under me and start working a finger then two fingers in and out of my ass. OH GOD I was so close to cumming. Jamie was still fucking Cindy's tight butt as I let out a scream and started shooting into Cindy's mouth.
I laid there and watched as Cindy cleaned my cock then closed her eyes and concentrated on the feeling of having Jamie fuck her. It was not long until Jamie started working in and out of Cindy's ass faster and faster. Jamie was grunting each time he thrust into Cindy. Small squeals of pleasure was coming from Cindy as she was being fucked.
Jamie growled and started shooting his cum inside Cindy. He came in her ass and just lay there for a few minutes resting on top of Cindy and panting hard.
As he was pulling his cock from Cindy, his cum started running down her thigh. I had to taste it. I leaned down and started licking Cindy's legs, then licking my way back to her cute ass. I buried my tongue deep once again, but this time I was licking Jamie's cum from Cindy's ass.
As I was bent over doing that, I felt something and looked back to see Jamie entering my ass with her cock. I don't think the girl even went soft, her cock was as hard and throbbing as it was when she was fucking Cindy.
I was licking Cindy's ass and eating the cum that was leaking out as Jamie started pushing her cock in and out of me at a slow pace. It had been over two weeks since I had been fucked and while Jamie was not as big as Tony, it felt good to have a cock in my ass.
Cindy was pushing her ass back to meet my tongue while I was pushing back to meet Jamie's thrusts. I reached under Cindy and started rubbing her clitty. She was getting hard again.
I quit eating Cindy's ass and told her to turn over. As she turned around I took her entire clit into my mouth. I was working my mouth up and down Cindy's clit as Jamie was working hers in and out of my ass at a faster pace.
I licked and sucked Cindy's clit as Jamie started pounding my ass hard and fast. I felt Jamie grab my hips and bury his hard clit deep and started cumming in my ass. I felt Cindy's clit start to throb and she came in my mouth seconds later.
We all laid there trying to regain out strength.
Later Jamie had changed back into his male clothes and I had put my black outfit back on, Cindy had changed into a sexy robe and we were sitting around talking and sipping our drinks. We came to the conclusion that we had to have this get together on a regular basis.
As I was riding the bus home, I thought to myself, that while I was still heart broken because of Tony leaving town, I still had Cindy, I still had Jamie. That's when I notice a very handsome older guy checking out my legs. Maybe life will not be so bad after all. _______________________________________________
More to come, especially if I continue to get positive feedback.