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. It contains a lot of back ground information that will help explain the stories contained in this series.
This Chapter is dedicated to my new friend Cindy.
I hope every one has a wonderful and safe holiday. MERRY CHRISTMAS EVERYONE.
Andi's Adventures - Part 07
I usually go home straight after school. Sometimes I play with Jamie, Sometimes someone else would come by. Mostly I would dress up and play with Moms vibrator and dream of Tony.
Today I decided I was going to go shopping. I had saved up some money and I wanted to buy myself some sexy things, maybe even a new teddy or nighty.
I took the bus to the mall and to calm my nerves I decided to walk through a department store first. trying not to look to obvious as I was looking at the sexy dresses, skirts and other clothes that a young woman would wear.
I was going to go the lingerie store eventually but this store had a big lingerie department so I decided to look there first. As I was browsing through the bra and panty sets, I noticed this really cute guy looking at a blue teddy with lots of lace and spaghetti straps.
He was Asian, 5' 3" or 5' 4" tall. Really slim, gorgeous eyes and short black hair. A thought hit me, was he buying that for his girlfriend or for himself to wear?
He must have felt me looking at him because he looked up and after a moment he smiled at me. I smiled back but then the moment was broken as a sales girl asked him if her needed help.
I went back to looking around and picked out a pink bra and panty set. I really liked that the bra was padded, it would look like I had breasts.
I nervously went to the counter and paid the sales girl. She smiled and told me to have a good day. I decide to celebrate my purchase of something sexy by getting a milkshake and some fries.
As I was sitting at a table in the food court, The cute guy I had seen before approached me and asked if he could join me, I said sure and invited him to sit down.
He said "I seen what you bought, it will look real good on you."
I started to give some lame response about how it was not for me, but looking into his eyes I knew I could trust him. All I said was "thank you."
He had a really great smile, he introduced himself as Cindy, which he said was his Fem name. He was in his early 20's and had been dressing since he was a teenager.
We talked for a long time but then he said he had to go to work. Then he shocked me, He asked me if i wanted to come to his apartment tomorrow after school and we could dress up. He told me to bring the things I purchased today but that he had lots of clothes he thought would fit me.
I was not sure if I should say yes, I mean he was nice and he looked harmless, but you never know. Yet I heard myself say I would love to.
He wrote his address on a piece of paper and gave it to me, he then said he would see me tomorrow and left. _____________________________________________
At school the next day Jamie asked if I wanted to come over, I felt bad about lying to Jamie but I did not want to tell him I was going to Cindy's so I just told him I wanted to but I had to do some things for my Mom.
I was nervous all day. For one thing, I had brought my new pink bra and panty set to school with me. They were buried deep in my book bag, but still if anyone seen them the least thing that would happen is that I would get humiliated, I could just imagine a worst case scenario.
Then, of course I was nervous about meeting Cindy at her apartment.
Later that day I found myself standing in the hall trying to control my breathing and working up my courage to ring the doorbell, when the door opened and there stood Cindy.
God she was hot!!!!!!!!!!!!! She was wearing a tight brown sweater, a
short black lycra miniskirt, and her really sexy legs were encased in black hose. She was wearing 4 inch black open toed heels, showing off her cute toes.
Her face was beautiful with just a hint of makeup and light red lipstick. The short hair style looked great on her.
She invited me in and I followed her. She offered me a glass of wine and I took it, it was the first alcohol I had ever had to drink but it was sweet and tasted good as I sipped it.
We sat and chatted until I had finished my wine, then decided it was time for me to get dressed. We went to her bedroom and she sit on the bed and watched me while I undressed, my hands were shaking as I took off all of my "guy" clothes.
I slid on my pink lace panties, then hooked my new pink padded bra and twisted it around and adjusted the straps. I would now have a decent set of 34b breasts.
Cindy told me how good they looked on me as she went to a drawer and removed a pink garter belt. It would match my bra and panties perfectly.
She hooked it around my waist and worked the garters under the waistband and out the lace edge of the leg openings. As she did this she brushed her hand against my "clit" and when she did it shot electricity through my body She seen this and kissed me lightly on the lips.
She handed me some white stockings and I sit on the bed to slid then up my leg. I felt the garters pull taunt as I stood up. I put on a pair of white 2 inch heels as Cindy was pulling out the outfit she said she thought I would look great in.
She handed me a black leather skirt and I stepped into it and worked it up my hips. I zipped it up and it came to just above the knee. next was a simple white blouse that had full length sleeves.
Cindy then started to apply my makeup. When she finished applying the dark red lipstick I thought I was looking pretty good, almost as pretty as Cindy was looking.
We strutted around, posing for each other and drank another glass of wine. Cindy suggested we go out and let the guys see how hot we were.
I hesitated because I was still not comfortable with the idea of going out dressed. I had never went out dressed up by choice. Maybe it was the wine, maybe it was because even though I had just met Cindy I really trusted her. She convinced me I could pass as a freshman in college.
She said we could go to a coffee house near her apartment where college guys liked to hang out. Cindy grabbed her purse and we headed out.
I felt the air on my legs, that and my nervousness was giving me goose bumps. We talked as we walked. Cindy was telling me about a guy she was seeing, His name was Rick and he was a senior in college.
From what Cindy was telling me, Rick was a hunk who worked out a lot. He was tall and muscular. She giggled as she told me what a good lover he was.
Cindy decided I just had to meet Rick, so she took out her cell phone and called him, she invited Rick to join us at the coffee house.
We arrived first and found an empty booth, Cindy ordered us both a latte. We sat and sipped our coffee and I noticed some of the guys were checking us out, they seem to be interested and none of them seemed to realized we were actually boys dressed as females.
I seen a big smile come across Cindy's face and I turned to see what caused it, There was a guy that had to be Rick standing at the counter. Cindy was right, he was gorgeous.
Rick and another guy made there way to our booth. Cindy jumped up and gave him a big hug and a really hot kiss. I caught myself thinking how I wished it was me jumping into Tony's arms like that, wondering what it would be like to show my desire for Tony in public.
When they finally separated, Cindy introduce me to Rick, and Rick introduced the boy with him. His name was Robbie and he was Rick's room mate.
Robbie was a cute blonde haired, blue eyed guy, not quite as tall as Rick but taller than Cindy or Me.
Rick slid in beside Cindy, Robbie slide close to me, God did he smell good. Robbie and I chatted while Cindy and Rick snuggled close and share several kisses. After several minutes Rick told Cindy that we should go back to her place.
Cindy said it was a great idea and we all left the coffee shop and headed back to her place. About halfway there Robbie took my hand, pulled me to him and asked, "are you a special girl like Cindy?" Yes I replied and he just smiled and held my hand all the way back to Cindy's apartment.
As we all entered Cindy's apartment Rick pulled Cindy to him and began kissing her passionately. I looked at Robbie who just smiled and pulled me tight and started kissing me. Lightly at first but then I started to relax and we before long we were going at it hot and heavy. That is when I felt Robbie's hand go to my breast and squeeze.
I looked over at Rick and Cindy and he already had Cindy's sweater off and her skirt up around her ass. Cindy really did have a great ass and sexy legs. I figured they would excuse themselves and go to the bedroom but it did not look like they were going anywhere.
Robbie had stuck his tongue in my mouth and I was sucking on it as I felt Robbie's hand cupping and squeezing my ass. I started unbuttoning his shirt as Robbie was undoing my skirt. The skirt slide to the floor as Rick raised his arms and I pulled the shirt over his head.
Rick was already down to his underwear and Cindy was between his knees trying to get them off, Rick had stripped Cindy of everything but her black lace bra and panties, garter belt and stockings.
Robbie was breathing hard as we watched Cindy pull Rick's boxers down his legs. Rick's huge cock came into view, it had to be 11 inches long. I smiled as Cindy engulfed it with her mouth.
I pushed Robbie down beside Rick and took my top off revealing my pink bra. I feel to my knees beside Cindy and started to unzip Robbie's Jeans. he was not wearing underwear, the naughty boy. His cock was nice but nowhere as big as Ricks.
Cindy was already deep throating Ricks cock as I started licking the shaft of Robbie's tool I heard both guys moaning as Cindy and I were working our magic. From the way Rick was moaning I knew I probably could learn a few things from her.
I felt Robbie's hand on the back of my head forcing his rock hard cock deep into my mouth. I tried to slow down and draw it out but Robbie had other ideas, he started forcing his cock in and out at an increasingly fast pace.
Out of the corner of my eye I seen Cindy's head moving up and down Rick's cock getting him closer and closer to coming.
I heard Robbie give a loud moan and start shooting strand after strand of cum into my mouth. Not long after Robbie came, Rick said "I am gonna cum sweetheart" and his body went rigid as he starting cumming in Cindy's mouth.
Cindy and I both pulled off of the hard cocks in our mouth at the same time, I had swallowed most of Robbie's cum but still had a little in my mouth. Cindy and my eyes met and it was like we were drawn to each other. We kissed deeply and our tongues pushed Robbie and Rick's cum from mouth to mouth sharing it.
Finally we broke our kiss and looked up at the guys who were watching us and smiling from ear to ear. We both got up and sat on the couch. Cindy snuggling next to Rick and I cuddled with Robbie.
Cindy was kissing Rick and playing with his nipples. It did not take him long to get hard again. I heard Cindy giggle as Rick whispered something into her ear.
She excused herself and headed to the bedroom, she came back carrying a small tube of gel. She handed it to Rick as they started kissing each other again.
I was kissing Robbie and slowly stroking his cock. we watched as Cindy got off the couch and slid her panties down and off. Then she got onto all fours as Rick positioned himself behind her.
Rick gently worked his fingers in and out of Cindy's sexy butt, then he worked some of the gel onto his cock head.
Robbie and I were lightly kissing and I was working my hand up and down the shaft of Robbie's cock. Rick tossed the lube to Robbie and told him to help himself. Robbie said he would pass which disappointed me a little but I continued to jack him off.
We watched Rick slowly ease his hard cock into Cindy's ass. He took his time and was so gentle, you could see it was so much more than just sex, Rick was in love with Cindy.
As we watched Rick and Cindy I leaned down and kissed the tip of Robbie's cock. Then I started sucking his Balls. I could hear Cindy squeal as Rick had managed to get all 11 inches into Cindy.
The look of lust and desire on Cindy's face was unbelievable, I wondered if my face looked like that when I was getting fucked. Then it hit me, the difference was that while I had been fucked repeatedly, Cindy was being made love to.
I went back to sucking the head of Robbie's cock as Rick started a slow pace working his cock in and out of Cindy. It was not long until he started picking up the pace. Pushing his cock in her hard and fast.
The room was filled with the sounds of Robbie moaning, Cindy letting out small delirious squeals every time Rick rammed into her, and the slapping of Ricks balls when they hit Cindy's ass.
I pulled off of Robbie's cock and was jacking him off as I watched Rick and Cindy make love. I wanted that with Tony. I wanted something special with the God of my dreams.
Rick was starting to work his cock in and out faster, he was breathing hard and sweating and he was fucking Cindy hard and deep. It would not be long until He filled Cindy's ass with his second load of cum.
After about 30 minutes Rick gave a growl and rammed his cock deep into Cindy's ass filling her up with his love juice. I heard Robbie moan and bent my head down just in time to catch his cum in my mouth.
I was licking Robbie's deflating cock as Rick and Cindy untangled and Rick pull his glistening cock from her ass. After Robbie was all clean He made some excuse to leave and dressed quickly. He did not even kiss me good bye.
I went to Cindy's bathroom and cleaned up and changed back to my boys clothes.
When I went back to the living room, the love birds were all cuddled up together sleeping peacefully. I scribbled Cindy a note telling her how much fun I had and added my Phone number.
I took the bus home and just barely got their before my Mom came home from work.
More to come, especially if I keep getting positive feed back. Thanks to everyone who has written to me so far.