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 11
I was sleeping so soundly, dreaming of Tony making love to me. Tony is an 18 year old Senior, he is 6'3" tall and all muscle. He was getting a lot of scholarship offers from big time college football programs. What I fantasize about though is his 10 inch cock.
I was awaken from my dreams by the ringing of the telephone.
It was the man of my dreams. Tony was calling to see if I had any plans for today. Mom had left specific instructions for me to cut the grass and do some other yard work, but when Tony asked me if I wanted to have some fun I forgot all about that.
Tony asked me if I was willing to go out somewhere with him. I asked him what he had in mind, all he said was "it will be fun, trust me, and you might want to wear jeans or pants if possible."
I rummaged around in my closet and found an old pair of jeans I had not worn in awhile. The jeans were tight on me and I did not know if I could bend over while wearing them, but I hoped my butt would be sexy when I had them on.
I took a shower, making sure I was all clean. I toweled off and brushed out my hair. I decided to wear it down today. It was really getting long and Mom had said something about getting it cut or trimmed at least.
I quickly painted my fingernails and toenails. While they were drying I sprayed myself with perfume and tried to decide what to wear with the jeans.
I slide my cream colored panties up my legs, Hooked the matching lace bra and turned it around, adjusted the straps. I decided even if I was going to wear jeans I was going to wear a pair of white sheer pantyhose. My legs tingled as I pulled the hose up my legs and smoothed them out. I chose a short sleeve black silk blouse that buttoned up the front.
I was thinking about heels, but decided to wear a cute pair of open toed flats. My red toenails looked so sexy through the sheer hose.
As I heard a distance rumble I checked the clock and it read 10:05. I looked out and there was Tony pulling into my driveway, riding a beautiful black and gold motorcycle.
I went out to greet him. Throwing myself into his strong arms. We shared a quick kiss. I felt his hands messaging my ass and squeezing my cheeks through my tight jeans.
We finally pulled apart and I asked him where he got the motorcycle. He told me that he had been helping his Dad rebuild and restore it to mint condition and that they had been working on it for over a year.
It was his Dad's motorcycle and they finally finished it last week. His Dad trusted him and since he put in so much work, said that he could take it for a ride today.
Tony asked me if I wanted to go for a ride in the mountains with him. Of course I said yes. I ran back into the house to get my purse. I figured we would be back before Mom got home so i did not leave a note.
I locked the door and went to where Tony was standing beside the bike. He handed me a helmet to put on, it was an old fashion helmet that did not cover anything but my head.
I strapped it to my head and crawled onto the bike behind Tony. As he started the bike up and I could feel the vibrations go through my body I wrapped my arms around his chest and hugged him tight.
We live in the foothills of North Carolina so it was not long until we were cruising the winding back roads in the NC mountains. It was an incredible rush. The wind blowing through my long blonde hair, the smell of Tony's cologne, my arms around Tony's chest holding the man of my dreams body close to mine.
After a couple of hours riding, We were somewhere on a back road with very little traffic. We came upon a creek so Tony pull off the road and stopped, he said it was time to stretch our legs.
We walk a little piece into the woods and came upon a secluded clearing. Tony smiled and said it was perfect. He told me to wait here as he made his way back to the bike.
As he returned he had a blanket and a bottle of wine. He fixed the blanket and we set down. He laughed and told me he had forgot to bring glasses. He opened the wine bottle and took a long drink, then he offered me the bottle. I took a few sips then passed it back to Tony.
I had only had a few beers in my young lifetime and a glass or two of wine when I had visited my friend Cindy, This wine was sweet and I decided that I definitely liked the taste.
We had passed the bottle back and forth a few times and I was already feeling the effects of the wine.
As Tony laid back on his elbows I decided to have some fun so I straddled Tony's crotch and started kissing Tony deep and passionately. Even through two pairs of jeans I could feel his cock start to grow and get hard. I ground my hips into Tony' crotch as we continued to kiss.
We broke our kiss and I leaned close and whispered into tony's ear, please make love to me, please right here, right now I all but begged. I started pulling Tony's T-shirt up and over his head. Scooted down and helped him pull his boots off. I reached for the snap of his Jeans and undone them, pulling them down and off of Tony's muscle bound legs.
Now it was my turn so I stood up and kicked my flats off my feet. I seductively started unbuttoning my blouse and then I let it slide down and off my shoulders. The air was still a little cool for spring but the warm sun felt good on my skin.
Next I unbuttoned my jeans, turned my back to Tony and shimmied the jeans down my sexy legs. Bending over to give Tony a good view of my ass, I stepped out of my jeans and tossed them aside.
I got on my knees and crawl toward Tony. As I got close to him I reached out my hand and cupped the huge bulge in Tony's Boxer shorts. MMMM it felt so big in my hand.
I worked the boxers down his leg, freeing his 10 inch cock. It was already hard and throbbing as my right hand cupped his balls and the left hand started working up and down his hard shaft.
Tony had laid back and closed his eyes as I leaned down and licked just the tip of his cock. I heard him let out a sigh as I took the head into my mouth and started swirling my tongue over his knob.
I continued to suck the head and stroke his shaft for a few minutes when I pulled off and told Tony I wanted him, no I needed him to fuck me and fuck me now!!!
He asked me if I had thought to bring any lube with me and I told him no I had not. He asked me if I still wanted him to fuck me and I growl oh yes!!!!
He told me to get on all fours and he had an idea. I had removed my pantyhose and panties and I was kneeling on all fours looking back at Tony when he took the wine bottle and pour some wine onto my ass. I felt it run between my cheeks and down my thighs when he started working his fingers into my ass.
He worked one then two fingers in my butt and started working them in and out, finally he added a third finger trying to stretch my ass enough to take his huge cock.
He eventually removed his fingers and I felt so empty, but it was not long until I felt the head of Tony's cock pushing against my anal opening.
I felt his strong hands on my hips pulling my ass back to meet his cock. I felt immense pressure against my opening then the head pushed through. Oh God, no matter how many times Tony has fucked me it is still painful when he first enters me.
He slowly pushed forward until he had all 10 inches in me. He held it there letting me get use to the feeling, then he slowly started working his cock in and out of my ass.
MMMMMM the feeling was incredible, yes it hurt alot at first, but it was not long until I started feeling shivers of pleasure working through my body.
In and out, In and out, In and out, long slow strokes. It felt so naughty, Getting fucked by my lover in the woods out in the middle of nowhere.
Tony had started to pick up pace so I reached down and started playing with my clit. It was so small but it had gotten hard from having Tony fucking me. It did not take but a few moments until I moaned and shot a small load of cum into my hand.
I guess when I came my ass started squeezing Tony's cock because I heard him moan and he started fucking me faster. You could hear birds chirping, the water in the creek rushing by and the sound of flesh smacking together as Tony was fucking me hard, fast and deep.
I was licking my cum from my hand and fingers as I felt Tony start to squeeze my waist with his strong hands and began forcefully slamming his cock deep inside me.
I could feel his body start to tense up and I knew it would not be long. Tony surprised me because he was able to hold off and fucked me for several more minutes before he slammed his cock deep into my ass and held it there.
Oh God it felt like he was filling my ass with gallons of cum.
Eventually his cock started to soften and with a pop, he pulled out of me and rolled onto his back. His body glistened with sweat as he laid in the sun. He open the wine bottle and took a big swallow.
He then pulled me to him and gave me a soft tender kiss. God I was in love with this man. I knew he did not feel the same as I did, but I had no doubt that he loved me in some way.I curled up beside him and laid my head on his shoulder and we both fell asleep.
We must have napped for almost thirty minutes and I was the first to wake up.
I looked down and Tony was still semi hard. So I took his cock in my hand and started working it up and down the shaft. In no time he was hard again.
I had such a kinky idea. I worked my way out of Tony's arms. Somehow I manage to get free without waking him up. I stood over Tony's hips and bent my knees. I slowly lowered my butt down onto Tony's cock. Since I still had some of Tony's cum lubricating my ass his cock head entered me with out any trouble.
I was halfway down his cock when his eyes flew open and he figured out it was not some sort of wicked dream. I seem him smile as he realized that this was real and he moaned as my ass had taken the entire length of his cock.
He reached up pushing my bra up exposing my hard nipples to the cool spring air. He began pinching and twisting them as I was bouncing up and down on his massive cock. What he was doing to my nipples hurt but felt great all at the same time.
After several long minutes of raising up and down on his cock my knees were starting to hurt, I was starting to fear that I would not be able to keep it up long enough for Tony to cum a second time.
That's when Tony pushed me and I landed on my back with my feet up in the air. Tony worked his way out form under me to where he was on his knees. His cock did not slip from my ass once while we were changing positions.
With Tony on his knees, and me on my back. Tony lifted my legs and pushed them over his shoulders, allowing him to drive even deeper into my ass.
We were looking into each others eyes as Tony continued to pound my butt with his huge cock. He let my legs go and reached for my nipples once again. He was pinching and twisting them again, he even started pulling at them. Oh My God, The feeling of having my breasts and nipples mauled while he was slamming his cock in and out of my ass was dizzying.
All great things must end eventually, after 25 minutes of fucking my ass Tony let out a growl and shot his second load of the day into my butt.
He rolled off of me and laid there panting. I reached for my purse and took out some Kleenex and started wiping the cum from my ass. I looked over at Tony and his cock was a mess.
I leaned down and gently started licking the pubic area around his cock. Then working my way from the base to the tip I licked tony's cock clean of cum. I leaned down and cleaned his balls, tasting his cum and sweat. I couldn't resist as I took the head back into my mouth and started sucking gently.
I sucked on his cock for a long, long time, I was working a steady rhythm up and down. I loved the feel of Tony's cock head hitting the back of my mouth just barely entering my throat. I still had to fight my gag reflex at times but I had gotten pretty good at deep throating Tony's cock.
Tony had started moaning again and while I loved sucking Tony's cock, my mouth was starting to get tired. Besides I was craving a mouthful of Tony's delicious cum. I increased the speed in which I bobbed my head up and down on Tony's cock. I felt his cock swell and them my mouth was flooded with cum.
Tony said it was time to head home so I reluctantly slipped my panties up my leg then put on my jeans. I fixed my bra, my nipples were sore from where Tony had played with them and I knew that they would be sore for awhile as the bra rubbed against them
I put on my blouse and buttoned it up as I watched Tony get dressed. I slipped my shoes back on and picked up my hose and stuffed them into my purse.
I helped Tony fold the blanket up and we headed for the bike, Tony was holding my hand as we walked.
As we started back I held Tony tight on the way home, I would kiss his neck and playfully blow into his ear. I thought what a wonderful day it had been. I wish it did not have to end so soon.
It was almost 5 in the afternoon when Tony dropped me off at my house. I invited him in but he said he needed to get the bike back to his Dad, he wanted to keep him happy so he could borrow it more often.
I gave Tony a deep passionate kiss good bye.
Like I said it was close to 5 PM and if I hurried I could get undressed and still get some of the yard work done before my Mom got home at 7.
I was smiling to myself, remembering what had happened today as I made my way inside the house. I was strutting and swinging my purse as i entered the living room.
That is when everything came to a screeching halt. There on the couch sat my Mother. She had a shocked and confused look on her face as her mind tried to comprehend what she was seeing. ______________________________________________
Unable to think straight, I blurted out, MOM what are you doing home so early?
She was still staring and had not said anything yet. Finally she regained control and told me to sit down and that apparently we needed to talk.
I was turning red from embarrassment of getting caught by my mother when I mumbled something about wanting to go change first.
She said "SIT DOWN NOW!!!!"
I fell into the recliner and felt tears coming to my eyes as Mom told me she had a million questions and was not sure where to start.
OK she said lets start at the beginning, when did I start dressing like a girl and how did it start?
I told her about the pep rally for the homecoming game and how some of the freshmen football players had to dress like cheerleaders for a joke. That was the first time I ever worn girl clothes and it was how I got started.
Next she asked me if I had been wearing her clothes all this time, I told her that it was a combination of her clothes and some I was able to buy for myself. I did not mention the clothes that Shannon, a neighbor girl had given me.
She said that explained a lot about the feeling she got sometimes that someone had gone through her stuff. That I must have been real careful about replacing her things but there were little things not quite right.
She then asked me how often did I go out dressed as a girl? I told her only a couple of times less than 5. That's when she told me about Mrs. Johnson from across the street.
Mrs. Johnson is one of those nosey neighbors and she had asked Mom about that cute blonde girl she had seen coming out of our house. Mom told me she had just figured I had a girl over and she did not want to embarrass me by asking about it.
She asked me several more questions, like did I have a fem name? How many people know I like to dress like a girl? How often did I dress?
Finally the big question. Was I gay? I started crying and told my Mom that I was not sure, that I think I was Bisexual. She gave me a stern look and asked me had I had sex with boys? I just nodded.
How about the boy on the motorcycle that had just left? When I could not look her in the eyes she knew that I had. She said "We will discuss that later, I can only handle so much in one day."
She then surprised me when she took me into her arms and hugged me, she told me she did not understand everything I was going through, but that she loved me no matter what.
Then she admitted that when she was younger she had experimented with other girls. That while it was fun she was attracted to men. She seen the look on my face and smiled, and said, what? too much information? We both laughed.
She then told me to go get cleaned up, that I should take off my makeup and put on my boy clothes for now and we would discuss me dressing as a girl around the house later. She told me that I would have to be punished because I kept things from her, that I sneaked out to meet boys and that I borrowed her clothes without asking.
Since it was the next week was the last week of school, I would be grounded for that week and the first two weeks of summer vacation. If nothing else happened we would discuss what was next then. I counted myself lucky and said Yes Ma'am, and ran for my bedroom. I never did find out why she was home early that day. __________________________________________
When I told Jamie on Monday about my Mom catching Tony and Me on Saturday he freaked, but I assured him that I did not mention his name so she did not know that he liked to come over and we would both dress in something sexy and fool around.
The last week of school flew by. We had exams on Monday, Tuesday and Wednesday. Thursday and Friday all we had to do was show up.
Jamie and I had been spending every day at lunch in the library. We had spent so much time there the Librarian was treating us like part of the staff.
She asked us if we would like to help her on Thursday and Friday instead of going to class and doing nothing, we both agreed to help her.
The first day all we did was sort and file books, we spent a couple of hours in the storage room stacking books. At noon Mrs. Andrews, the librarian said she was going to lunch, we could stay in the library but she would lock the door when she left so no one would disturb anything.
We ate our lunch and talked about all sorts of things. Jamie finally admitted he was not looking forward to going 3 weeks without us getting together.
That night I decided to wear my sheer black boy shorts, I had not worn panties to school before because of gym class and I was afraid of being caught.
Friday Morning after I had dressed, I decided to stuff the matching black bra into my book bag and left the house.
After home room, Jamie and I got busy trying to finish straightening the storage room in the library. We worked hard all morning and was almost done by lunch time.
Mrs. Andrews said she was going to lunch and for us to lock the door behind her. Jamie stayed in the storage room and I went with her to lock the door.
I realized we would probably have an hour or so alone in the library together, so I got my book bag and went to the back of the library. I knew it was a big risk and if we got caught I would get Jamie and myself in a whole lot of trouble.
Personally I did not like the idea of having to go 3 weeks without fooling around with Jamie either. I kicked off my shoes, took my T-shirt off and slide my pants down and off. I found the bra in my book bag, hook the clasps and adjusted the straps.
I made my way to the door of the storage room and I hollered to Jamie and told him to close his eyes, I had a surprise for him. I asked, are you ready?
He said yes, So I stopped in the doorway and struck a sexy pose. I told him to open his eyes.
He seen me and just stood and stared. I smiled and said "so, what do you want for lunch big boy?"
He licked his lips and I went to Jamie and kissed him. We kissed for a long time and I felt Jamie's hands start to message my panty clad ass. I broke the kiss and told him we had better hurry if we wanted to do this before the Librarian came back.
Jamie looked like he was in a daze but he hurriedly got undressed. There was an old desk in the corner of the storage room and I pushed Jamie back against the desk and dropped to my knees.
Jamie was already hard so I took the entire length into my mouth, it was not as big as Tony's cock but I still loved to suck on it. I was bobbing my head up and down Jamie's cock and he was already moaning.
I was afraid we had just enough time for Jamie to cum only once and I wanted him to fuck me like the cock whore I had become.
I let his cock go and stood up, I slid down my panties and bent over the desk. I looked back at Jamie, wiggling my ass at him.
He aimed his cock toward my hole and since I had been having sex with Tony, Jamie's cock entered me with little trouble. Jamie was eager and it took very little time for him to start fucking me fast.
I was clenching my ass tight trying to make it tighter for Jamie. He was fucking me faster and faster and I knew he would not last long. All to soon I felt Jamie fill my cute butt with his cum.
I was bent over desk, sweating and Jamie still had his cock in my ass. Slowly He pulled out and looked for something to wipe his cock off with. I went to my book bag and took an old towel out and wiped the cum out of my ass. Then I gently wiped Jamie's cock off.
We both got dressed and I put the bra back into my book bag. I kissed Jamie and asked if that would keep him satisfied for a few weeks until my grounding was lifted. He smiled and said "probably not".
Mrs. Andrews return shortly after that to find us working hard. As everyone started to leave school that afternoon, I wanted to find Tony and at least give him a kiss, but he had already left.
Oh God, it would be a very long two weeks. ________________________________
More to follow, especially if I continue to get positive feedback. Thanks to all of those who have written me so far.