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.
Andi's Adventures - Part 10
When I arrived home from school the answering machine was blinking. I played back the messages and one was from Kevin. The cute boy who's brother made me entertain on his birthday.
Kevin is 5' 7" tall, brown hair, dark brown eyes, he is skinny but has the cutest smile.
I called Kevin back to see what he wanted. After some small talk he finally said he had called because he wanted to see me again and wanted to know if he could come over.
I told him not today. He was disappointed. Then I told him that I would meet him tomorrow.
Kevin is a skater. He goes to the skate park not far from my house. The skate park is part of a bigger park. I told him I would meet him there after school, around 4.
I had been dressing up for months now. Tomorrow I was taking a big step. I had never went out in public dressed as a girl without someone with me. I thought with all the practice I have had that I could pass with out much trouble and tomorrow would be my solo debut.
When school let out, I knew I had to rush to get ready and meet Kevin in the park. I took a quick shower, dried off. Sprayed myself lightly with perfume.
I decided to wear a white bra (which I had to stuff with some balled up stockings) and cream colored panties. A short denim skirt and a green sweater. It was close to spring and the temperature was warming up but it was still cool at times. So I decided to wear a pair of black tights.
After I dressed I did my makeup and applied my favorite cherry red lipstick. I put on a pair of black flats.
I grabbed the purse that Shannon had given me. I put my house keys, tissues, my lipstick and some money in it and was ready to leave.
I checked myself in the mirror. I thought Kevin would like the way I looked and that I should pass with no trouble. I was still nervous but I took a deep breath and left the house.
As I was walking down the sidewalk a woman was walking toward me, She glanced at me, smiled and went on her way. Since she did not start pointing and laughing I felt a little more comfortable.
As I approached the park I seen Kevin and his friends in the part of the park roped off for skateboarders. I sat down at a picnic table and watched them. As I sat there I noticed I was getting looks from some of the guys in the park, It was still a little scary but flattering.
Kevin noticed me setting on the bench and he skated over to me and set down. He said hi, then told me how great I looked. I blushed and thanked him. We sat there talking, I think he was trying to get the courage up to kiss me.
I took the initiative and leaned over and kissed Kevin lightly on the lips. He asked me if I wanted to go for a walk and I agreed. Kevin took his skateboard over to one of his friends and asked if he would watch it for him.
You could hear his friends teasing him. As we started walking, he reached over and took my hand in his. We walked in silence for a while then we turned down a deserted path and realized we were alone in a secluded area. We stopped at a tree and I leaned back against it as Kevin kissed me again.
We stared making out fast and furious, I felt his hand exploring my body, he ended up rubbing and squeezing my ass as we were kissing. As we broke our kiss we were both breathing heavy. He panted in my ear that he wish we could go somewhere and do more than kiss. I took his hand and led him further down the path we were on.
We found a bench and sat down and started kissing again. As we kissed I worked my hand under Kevin's shorts and underwear. Oh my He was already rock hard.
I took a quick look around, then whispered for Kevin to lift his hips, as he did it I worked his shorts down exposing his cock. Again I looked around.
I knew if I was going to do this we had to be quick so I leaned in and engulfed the length of his hard cock. I heard Kevin moan as I did. I started working my mouth up and down his shaft . I swirled my tongue around the cock head.
There we were, on a bench in a public park, I was bent over, my head bobbing up and down on Kevin's cock. I felt Kevin tensing up and knew it would not be long. I squeezed Kevin's balls and that sent him passed the point of no return.
Kevin rewarded me with a mouthful of cum which I swallowed down with ease. I pulled off and kissed his cock head then he pulled his shorts back up.
We walked back to where his friends were. He kissed me goodbye and I walked home.
Jamie had come home with me on Friday. We were on the bed and I was dressed in a dark blue nighty, while Jamie was wearing a black lace teddy. We were just starting to make out when we heard a car in the driveway.
I told Jamie to stay there while I went to see who it was. As I looked out my heart skipped a beat. It was Tony, the man of my fantasies.
Tony is black, 6' tall and muscular. He also has a massive 10 inch cock that I dream about at times.
Now Jamie knew about the way I felt about Tony and that I had been with him a couple of times. No one knew about me and Jamie. I got a devilish idea.
I opened the door and Tony seen what I was wearing and he took me into his big strong arms and kissed me deep. I felt his hands on my ass squeezing.
As we broke the kiss we went back inside as Tony asked me if it was ok that he had come by today. I assured him I was happy to see him any time.
I told him to set on the couch and I would be right back, that I had a surprise for him. As I entered my bedroom I seen Jamie starting to take his lingerie off. He looked sad and said he had heard Tony come in and he knew I wanted to spend time with him. He said he would just slip out the back door.
I stopped him, took him into my arms and started kissing him. I whispered "I have an idea, why don't you join us?"
"No way!!" He said.
"Jamie I know you love to play with me, but I think its time you see and taste a real cock."
Jamie still did not seem like he was going to go alone with me when we both heard Tony say "why don't you introduce me to your sexy friend?"
Before I could say anything I heard Jamie say "Hi Tony, I am Jamie."
You could see Tony realized that it was Jamie, the boy that i hang with in the library during lunch.
Tony just smiles and kiss "Jamie on the lips. I watched as Jamie gave in completely to Tony as they started really kissing and making out. I watched this a few minutes then growing impatient and maybe a little jealous, I cleared my throat hoping to get their attention.
Tony laughed as they broke the kiss, "Don't think I forgot about your sexy ass little girl. I want to see you hot girls make out for me."
Jamie and I started kissing deeply and passionately, I was cupping her butt as we were making out. I slipped the strap of her teddy down her shoulder and sucked a nipple into my mouth.
I looked over and Tony was undressing, he had already removed his shirt showing off that incredible upper body. He was sliding his jeans down as I started to nibble on her nipple while rubbing her clit through the crotch of her teddy.
Tony was down to his boxer shorts as he set on the bed. I led Jamie over and we both kneeled before him. I took hold of Tony's shorts and pulled then down his legs exposing his cock. It was hard and throbbing and looked ever bigger than I remembered.
I kissed Jamie one more time then pushed her head toward Tony's cock. She hesitated so I leaned in and whispered in jasmine's ear, you know you want to taste it.
Finally she closed her eyes and took a deep breath, leaned down and kissed the tip of his cock. She slowly took the head into her mouth and started sucking. I smiled when I heard Tony let out a moan. As Jamie was sucking on the head, I leaned down and started sucking on his balls, first one then the other.
Jamie pulled back and smiled at me. We both seemed to know what the other one was thinking as we both went to licking his cock at the same time. Our tongues met as we got to the top of his cock. We shared a deep passionate kiss then it was my turn to suck on Tony's cock.
I started by taking almost half of his ten inches deep into my mouth. Jamie seemed to be impressed as I started working my mouth up and down, taking more and more into my mouth.
As Jamie watched me deep throat Tony's cock, all she could say was WOW.
After a few minutes I pull off his cock and told Jamie it was her turn. She said there was no way she could do that. I told her it took lots of practice for me to be able to do it, just try her best.
Jamie smiled at me and took the head back into her mouth, she started bobbing her head up and down, at about 7 inches she started gagging and pulled back. She took a deep breath and went back to sucking Tony's cock.
I watched Jamie get into a steady rhythm so I kissed my way up Tony's muscular stomach and chest. Stopping to toy with Tony's nipples then kissing him deep.
Tony was moaning into my mouth as Jamie was doing a great job sucking his cock. I felt Tony's body start to stiffen up and I knew he was about to cum.
Before I could break the kiss and warm Jamie, Tony groaned and flooded her mouth with a huge load of cum.
Poor Jamie was struggling to swallow as cum started flowing out of the corners of her mouth and running down her chin. She finally let Tony's cock slip from her mouth and looked up at us. I pulled her to me and licked cum off of her face. We shared a deep kiss and that is when Jamie pushed more of Tony's cum into my mouth.
We made out and savored the taste of cum. Finally we pulled apart and noticed Tony sitting there grinning and playing with his still semi-hard cock.
Tony informed us "I have never got to watch two sexy girls making out up close. I would love to watch you eat each other."
Jamie smiled at me and climbed on the bed laying down on her back. I crawl on the bed and got on top of her. I felt her undoing the snaps on my teddy exposing my "clit" and my ass. I slid the lace edge of her nighty and started kissing her clitty. We were both small but so hard.
We had been sucking each others cock for several minutes and I knew I could not last much longer when I felt Tony crawl on the bed behind me. He had got the lube off the night stand beside my bed and began working one then two fingers into my ass. The pressure in my ass felt so good and I could not hold out any longer, I came in Jamie's pretty mouth as Tony was fingering my ass.
Jamie was still gently licking my softening cock when Tony removed his fingers from my ass. I felt him move around behind me and soon felt his large cock head against my ass. He started pushing forward.
Oh God, it always hurt at first but I knew soon it would feel so good. As Tony pushed forward, I pushed my ass back and soon felt the head pass my anal ring. Tony paused for a minute letting me get use to his huge cock. Then he started pushing forward again forcing more and more of his cock in me.
I had quit sucking Jamie while Tony entered me. As Tony started a slow rhythm in and out of my ass, I went back to kissing, licking and sucking on Jamie's cock. I started feeling a warm feeling deep inside me as Tony started fucking me faster and faster.
As I sucked Jamie's cock my hand went under her to insert a finger into her cute butt. It did not take long after I started fingering her ass that she rewarded me with a tasty load of cum.
After I had sucked her dry and licked her cock clean, I rested my head on my arms and closed my eyes. I lost myself completely to the feeling of Tony's huge 10" cock going in and out of my ass.
Since he had already cum once today, he was taking his own sweet time fucking me. In and out, in and out, in and out he worked his cock.
Finally after what seemed like hours I felt Tony increase speed and he started slamming his cock in and out of my ass hard and fast. He was driving his cock deep and rough into me.
OH God it felt so good, I was so in love with Tony. I knew he did not feel the same way but at the moment I did not care about that, all I cared about was that he kept fucking me.
I knew Tony was getting close so I was squeezing my ass trying to milk the cum from his cock.
By this time Jamie had wiggled out from under me and was sitting back watching us go at it.
Tony let out what can only be described as a fierce growl and drove his cock deep into my ass and held it there. I felt shot after shot of cum fill my ass. That in turn caused me to cum again. This time I came so hard I almost past out. I seen stars and felt light headed as Tony continued to empty his cum deep inside my body.
As Tony pulled out I felt cum running down my thighs. Tony flopped down on the bed, Jamie on one side and I was on the other. Tony started kissing Jamie as I moved down to lick and suck Tony's cock again.
I was licking Tony all clean as Jamie and Tony was kissing each other deep. I continued to lick then sucked the head back into my mouth. My Stud was getting hard once again.
I smiled up at Jamie and asked her if she was ready to lose her virginity. Her eyes got wide and said there was no way she could take a cock that big. We all three laughed.
I went back to sucking on the head of Tony's cock. Tony and Jamie were both laying back watching what I was doing. As I sucked Tony's cock I reached out and started stroking Jamie's little cock.
Then I switched and started sucking Jamie's cock as I worked my hand up and down Tony's cock.
I would suck on Jamie's cock and stroke Tony for a few minutes then switch and suck Tony and stroke Jamie's cock. Jamie and Tony had went back to making out as I worked on both cocks.
I knew Jamie would be the first to cum so I concentrated on her. Her cock was so much smaller than Tony's but it filled my mouth nicely. I was deep throating Jamie, sucking hard as I messaged her balls. It was not long until I felt her cock grow a little and she came in my mouth a second time.
I gently licked her clean, then let her soft cock slip from my mouth. Now for the main course.
I went back to licking Tony's cock from the base to the head. sucking and bathing his balls with my mouth. Tony was rock hard once again so I took the head back into my mouth.
I started working my mouth up and down. MMM I realized just how much I loved sucking Tony's cock. I was a slut in love. I would do anything Tony asked to make him happy.
I felt the head of his cock hit the back of my throat. I sucked harder and harder, Tony's cock entering my throat cutting off my air. I was getting light headed again.
Tony had cum twice already, but that's ok because I could suck Tony's cock all night. After about 20 minutes my mouth and throat were starting to hurt. I was trying all my tricks, deep throating his cock, then pulling back and swirling my tongue around the head. I was messaging Tony's balls as I sucked his cock.
I felt Tony's hand on the back of my head forcing me to take the entire length of his cock in my mouth and he held it there. I felt his cock pulse and then Tony was shooting his cum deep down my throat.
It being his third cum in less than two hours, there was not a lot of cum but I felt proud that I could swallow it all without missing a drop.
All good things must end and finally I let his magnificent cock slip form my mouth. I gave the head one last kiss and lick.
Tony thanked both of us for a great time, Gave each a kiss and left. As Jamie and I finished taking off our lingerie, she asked me if getting fucked was am good as Tony and I made it look? I said it was incredible and she should try it sometime. Jamie said she might, but maybe with a guy who wasn't as well endowed as Tony.
In the back of my mind I thought about introducing Jamie to Kevin, but that is a story for another time.
More to come, especially if I continue to get positive feed back.