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 Adventure - Part 14
For the past several days Mom had been acting depressed and I was getting worried about her. So after I finished washing and putting away the dishes, I took Mom a glass of wine and asked her if everything was ok.
She said it was a combination of things. She was burnt out at work.
She is a nurse and you get tired of seeing all that sickness and death. She did not say it but I knew there was problems between her and her boy friend Mike. I had heard them arguing the other night and he stomped out and slammed the door.
I got Mom a second glass of wine and after handing it to her I sat at her feet and started messaging them. She told me how nice that felt and I guess the wine was loosening her up because she started talking about Mike.
She said he was nice enough but he liked to be really kinky in bed. She then realized what she had said and blushed a deep red. As I listened I had worked my hands up Moms legs. She was 38 and in great shape.
She is 5'2" tall, 120 pounds, short red hair and dark green eyes, Mom was beautiful. She could fine a new boyfriend with no problem if she wanted to, but Mike has been the only boyfriend she has had since her and Dad separated and then divorced.
Mom had gotten quiet and was deep in thought as I continued to message her feet and lower legs, I noticed I could see up the leg of her shorts and noticed the sexy purple panties she had on.
Oh God, I realized my little clit had become hard in my panties. Thank God it is so small and I had on a lose fitting skirt or Mom may have noticed and that would have been truly embarrassing.
I decided that it was time I excused myself and told Mom I was going to turn in. As I kissed her on the cheek her arm accidentally brushed across my crotch making me even harder if at all possible.
Mom could not miss me blushing a deep red as I left the room. As soon as I got to my room I removed my skirt and top, my white lace ball and flung myself onto the bed. I laid there and caressed my nipples and started rubbing myself through my panties.
I could not help but think about my hands on Moms legs and the sight of her sexy panties. It was not long before I let out a loud moan and shot a huge load of cum into my hand.
As I licked the cum from my fingers I realized that this was a first for me. The first time I had jacked off thinking about a woman, even if it was my Mom, she is a very sexy woman. ________________________________________________
It was a hot afternoon in late July as I was walking to the local convenience store. I was wearing a white tank top with spaghetti straps, my short denim skirt, light blue panties, and sandals showing off my dark red toenails.
No I was not wearing a bra, I did not have breasts but my hard little nipples made the sexiest little bumps under my tube top.
I had my long blonde hair up in a french braid, I had on just a touch of makeup and some bright cherry flavored red lipstick.
At the store I looked through the magazines but could not find any I wanted so I just grabbed a coke and headed to the counter. As I was paying this gorgeous older black guy entered the store, he was over 6 feet tall, muscular chest and a shaven head. He was wearing a pair of tight jeans that looked so hot on him.
The clerk had to clear his throat to get my attention so he could give me my change. I guess I was lusting after the guy pretty good.
I left the store and in the parking lot I stopped dead in my tracks. There in front of me was the motorcycle Tony had taken me for a ride on.
I was filled with emotion as it made me think of the day Tony and I had ridden into the mountains and found a secluded spot beside a creek and made love. Well it was making love to me, I guess Tony just considered it another fuck.
"Hi there little lady" I heard a deep voice say. I looked up to see the black man who had caught my attention earlier.
"Oh Hi there" I replied and gave a shy smile.
"Do you like motorcycles?" He asked. "Maybe you would like a ride on mine?"
I hesitated, "Actually I think I have already had a ride on this bike."
"oh really? I think I would remember giving a pretty little thing like you a ride."
"It was not you Sir, it was Tony, Tony Phillips, we rode up into the mountains."
I seen a big smile cross his face "So you know my son?" Then he introduce himself as Marcus.
"Yes, I thought we were close at one time, but I guess he lost interest and then he went to visit his Mom in Ohio. How is he doing?"
"He is fine, he is getting ready to report to college for football practice."
He must have seen the pain in my eyes remembering Tony, because he put his arm around my shoulder. "Are you ok?" he asked.
"Yes" I whispered, "Thinking of Tony just brought back some fond memories, and I guess I miss him more than I thought I did."
"I hate to see someone as pretty as you so sad, What is your name little lady?"
Giving him another smile, "Oh I am sorry, my name is Andi"
"Well Andi, it is a pleasure to meet you." He took my hand in his and kissed it.
I noticed his eyes kept going up and down my body checking me out. He was standing there with his arm around me and I felt so small and weak next to him. He leaned in and kissed me lightly.
"Come with me" he said as he picked me up and sat me on his bike, it was not an invitation but a command. My skirt rode up exposing my panties and I blushed a deep red. He straddled the bike and started it up. Slowly pulling out into traffic.
It was scary riding a bike without a helmet so I held on tighter that usual. I noticed that Marcus had a musky smell. Not unpleasant but one of a mad who had put in an honest days work.
I was nervous, scared and I have to admit a little bit excited because I had no idea where we were going or what we were going to do when we got there.
We rode west for 15-20 minutes and then turned onto a dirt road. It wound through the woods for 1/2 a mile and came to a brick house with a small garage attached.
Marcus pulled into the garage and shut off the bike. He got off the bike and then helped me off. He pushed me up against the garage wall and kissed me deep.
I hesitated at first but quickly gave in and started kissing him back. His tongue was exploring my mouth with his tongue while his hands were squeezing my ass.
We finally broke our kiss and he took his key and unlocked the door.
Scooping me up in his arms he carried me through the front door like a man would do on his wedding night.
He carried me through the house kissing me occasionally as he headed for the master bedroom. He left no doubt about what he wanted or what was about to happen.
He lightly set me down on the bed and stepped back. He hurriedly started to strip. I was watching in anticipation.
He smiled at me and told me "don't just sit there Angel, get undressed."
I decided I had better tell him about my little secret. I was afraid he would lose interest in me when he found out, or worse, beat the crap out of me.
"Uh Marcus, we need to talk first, I need to tell you something."
He laughed "What is it? Don't tell me you are a virgin."
"No Marcus, please do not be mad, but I am not what you think." I was on the verge of tears but took a deep breath and continued "I was born a boy. I started trying to be the girl that was inside of me about a year ago."
He looked amused and I believe he thought I was joking. I decided to show him. I pulled my skirt up then I eased my panties down showing him my little 4 inch penis.
He did laugh then. "It's ok Honey, its so small You would never be mistaken as a guy. Now get undressed!"
I watched him take off his jeans showing a pair of boxer shorts that contained a huge bulge. I swallowed hard and unzipped my skirt and shimmied out of it.
I did not realize just how much I had missed Tony's big cock until now. I pulled my tank top off exposing my flat chest and hard nipples. I slide off the bed and got onto my knees in front of Marcus.
I reached out and cupped his cock inside his boxer shorts.
He was smiling down at me,"I know Tony is big, but he is still a growing boy, a sweet thing like you needs a Man's cock." He hooked his fingers into the waistband of his shorts and pulled then down his legs.
OH MY GOD, Tony was big, almost 10 inches long, but Marcus was just semi-hard and he was at least that big or bigger. My mouth was watering. I reached out and took it into my hand and started to stroke it slowly.
I kissed the tip, licked the head gently. Marcus's cock was a sexy mocha brown, with a deep purple vein running the length of it. I let my tongue trace the vein from tip to bas and back again.
Marcus was now rock hard. It had to be 10 and 1/2 inches or more and 3 inches around. My hand could not go completely around it as I continued to jack it up and down slowly as I tried to take the head into my mouth.
My lips were stretched to their limit. I got the head into my mouth and was slowly trying to get more of his monster cock. While it was hard it felt silky against my tongue.
With one hand I reached down and started cupping and squeezing his large balls. Marcus was moaning as I took his cock out of my mouth and started licking and sucking his balls. Then I went back to sucking on the tip. It was oozing with pre cum.
Suddenly Marcus pushed me away and told me to lie face down on the bed.
"No Sir please, its to big it will split me apart." I begged as I realized what he was planning on doing.
"I said get on the bed Angel. I know you have wanted me to fuck you from the start. Now I am going to give you what you deserve, what you want."
He went into the bathroom and came back with some kind of lube.
When he returned I had removed my panties and crawled onto the bed.
My heart was pounding with fear and excitement. Tony filled my ass to the limit but Marcus was going to do even more.
I felt a lube covered finger work into my ass. He was being gentle and it felt good. I let out a moan as he worked a second finger into me.
"You are tight, but I will stretch you out, you will thank me later."
I realized I was pushing my butt back to meet his fingers as he worked a third finger into my ass.
By the time he had worked the fourth finger into me I was all but begging him to fuck me.
When he pulled his fingers from my ass I felt so empty. I was still pushing my ass back to him when I felt him slap my right ass cheek playfullyand laugh.
"I see you are eager for my cock, well its time you get what you want."
I was shivering as I felt his cock head against my anal opening. He steadily increased the pressure and my ass was being painfully stretched. It hurt like hell.
"Please Marcus, NO. It hurts to much. Please stop."
"Sorry Angel, I don't think I could stop now even if I wanted to. And
believe me I DON'T WANT TO."
With that he pushed harder and the head popped in. OH GOD the pain, I was seeing stars and having trouble breathing. He let it rest there for a few moments letting me get used to the feeling .
He slowly pushed forward. Working inch by inch into me. Then he would pull back. It hurt worse when he pulled back then it did when he pushed forward. It was incredibly painful either way.
I loved when Tony fucked me, but with Marcus the feelings was even more intense. I felt I was on the verge of passing out and I felt my ass was on fire.
The heat started to spread throughout my body and before long I was feeling pleasure in every fiber of my body. Marcus increased the speed in which he was working his cock in and out of me. I felt my body tense and knew I was about to cum.
My head was buried in the pillows, My ass was in the air with Marcus fucking it hard, rough and deep.
I screamed into my pillow as I came. I heard Marcus say "OH FUCK YEA, You love my cock little girl." He was grunting as he was pounding into my ass.
He was breathing heavy and we were both covered in sweat. Our sweat, my perfume and his cologne mixed to fill the room with an intoxicating aroma.
Marcus was holding me by my hips, working his cock into me hard and fast. I heard him let out what can only be described as a combination groan and deep growl as he started cumming into my ass.
His hot cum filling my ass sent me over the edge and I came a second time and blacked out.
When I came to Marcus had already cleaned up and dressed, he was sitting in a chair watching me. I started to move and found that my whole body ached.
"I wondered how long you would sleep. Get up and get dressed so I can take you home."
I crawled out of bed, grabbed my skirt and top and stumbled to the bathroom. I took a quick shower and got dressed.
Nothing was said on the ride back except when he asked me where I lived. I told him , then said it might be a good idea to drop my off a block away from the house.
As I got off the bike, Marcus pulled me to him and kissed me deep. Then he thanked me for an incredible fuck.
He smiled, "SO what are you doing on Friday?"
"I have no plans why?"
"Meet me at the store around one O'clock." It was not an invitation but another command.
I just smiled and nodded.
One last quick kiss and then he drove away. I walked the one block to my house wondering what have I gotten myself into now.
More to come, especially if I continue to get positive feedback.