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 09
Jamie and I had been spending at least one afternoon a week together. Sometimes we would have sex with him as a guy and me as his girl. Sometimes we were both dressed up and we considered ourselves lesbians.
One day I confessed to Jamie about sucking Tony's cock. At first he seemed kind of jealous, but curiosity got the best of him and he started asking for details. He ended up fucking me harder than ever before that day.
Now Jamie knew why I acted the way I did around Tony. He thought my crush on Tony was cute. _______________________________
February 14 was approaching, and what girl does not dream of romance on Valentines Day. Valentines Day was on a Thursday. On Monday, I seen Tony coming down the hall and I asked him if we could talk. He said he had to get to class but we could talk after school. For me to meet him at his locker.
After the last period ended I was hanging around the water fountain watching Tony's locker waiting for him to show up.
When he started getting his stuff out of his locker I walked up to him. Tony smiled at me and lowered his voice. "Hi, so what do you want?"
"I heard you tried to get back together with Tracy, how did it go?" I asked.
He looked mad "She told me there was no way we would ever date again."
"I am sorry Tony, I really am. Especially this close to Valentines Day." I was trying not to look happy about it.
"Tell me about it, I have already asked for the night off so we could go out. I guess I can go ahead and work now."
"Well.....oh never mind."
"What is it Kido?"
"You could come to my house on Thursday" I blurted out.
"I don't know, it was fun the last time but I am not sure.....I want a real girlfriend."
"Tony...I like you a lot, I will do anything a real "girl" will do and more. I will do anything you want me to. Tell you what, if you can't find a date by then, let me know if you want to come by." I all but begged.
"we'll see" was all he said. ______________________________________
That afternoon I was lying on my bed wearing a white bra and panties.
I had my Moms 12 inch vibrator deepthroating it imagining I was sucking Tony's monster cock. Then it dawned on me, in my lust I had promised Tony I would do anything he wanted if and when he came over.
What if he wanted to fuck me? His cock was 10 inches long and at least 3 inches around. I have been fuck several times but never by anything that big. He would rip me apart and hurt me bad if I was not somewhat prepared.
I slid my panties down and flipped over onto my stomach, pushing my butt into the air. I had been sucking on the vibrator so it was wet. I slowly started to ease the vibrator into my ass. It was not to uncomfortable so I started moving it in and out working more and more of it into me.
After a few minutes I had fallen into a steady rhythm fucking myself. I realized I really, really wanted Tony to do this to me. I was getting so hard just thinking about it. It was not long until I shot a load of cum onto my bed.
I removed the vibrator and took it to the bathroom to clean it and then I replaced it in the drawer of my Mom's night stand. I stripped the sheets off of my bed and put them into the washing machine.
My butt was a little uncomfortable but not sore. Maybe with a little work I could take Tony's nice cock and please my man the way a woman should.
I spent the next two afternoons fucking myself with the vibrator trying to get stretched out so I would be ready for Tony, Now if he will actually come by on Thursday. _________________________________
It was finally Thursday and Tony had not said anything to me since I made him the offer. I guess I could invite Jamie over but I doubt if my heart would be in it and that would not be fair to him.
As I was getting my books for the last class of the day A note fell out of my locker. I quickly picked it up and read it.
It read, Meet me at my car after school, Tony
My heart skipped a beat, maybe my fantasies were going to come true after all. I have no idea what I did in class that afternoon, I was so anxious to talk to Tony.
The bell finally rung and everyone piled out into the hallway getting ready to leave.
I got my stuff and went to meet Tony. When he walked up he asked if my offer was still good. I smiled and said of course.
"Get in and I will give you a ride home." He offered.
"Tony, My Mom's boyfriend is taking her out straight from work, we will have until 9 tonight at least." I explained. "Give me a little time to get ready. I want to make it special. For both of us."
We decided he would come over at 5, and we went our separate ways. I all but ran home. I was so excited and very nervous. ________________________________________
I took a long hot shower making sure I was clean head to toe. I has only done it once or twice, but I even shaved my legs. I dried and powdered my body.
I looked through the small amount of clothes I had been able to stash in my room. I wanted something sexy but I did not want to look trashy.
I finally decided on the sleeveless floral dress that Shannon had given me. It came to just below my knees. I went to my Moms bedroom and borrowed her white garter belt and some white stockings. I added some simple white satin panties. I put on the garter belt , stockings and panties.
All I had to choose from in shoes were two sets of heels, one was 2" Black heels, the other was 3 " heels in Pink. I decided pink would go better with the floral print of my dress so I slipped them on. Then went to apply my makeup. I wanted to look as good as possible for Tony, I applied a base, some blush, did my eyes, and put on some dark red lipstick.
I lightly sprayed myself with perfume, I wanted to be able to wash the scent off of me before Mom got home from her date.
I checked myself in the mirror. I looked hot!!! Ok so I was becoming a conceded bitch, but I really did look good.
I put on my dress and went to the kitchen to get a drank of water and calm my nerves. It was erotic to hear the click of my heels on the hardwood floor of the kitchen.
It was fifteen minutes after five and I was worried that Tony had changed his mind, I went to check my makeup and hair. I wanted to look as good as I possible. I heard the doorbell. This was it he was here.
I took slow small steps trying to get my nerves under control. I opened the door. Oh My God, Tony was so handsome standing there in a polo shirt and black jeans.
He must have been surprised at how good I looked because he just stared at me for a moment, then he broke into a grin as he handed me a single rose. What a romantic.
I let him in and we sat on the couch. We were both nervous and sat there trying to make small talk, but it was not long until he took me into his strong arms and was kissing me.
He pushed his tongue into my mouth, I let him explore for awhile then I began sucking on his tongue. His hands were exploring my body. I felt him caressing my back, then one hand on my thigh.
I eventually broke the kiss and kneeled before Tony. I untie his right tennis shoe and remove it, then repeated the process with the left shoe.
I removed his socks. Smiling sheepishly I reach for the button of his jeans. My hands were shaking as I undone the button, then unzipped his jeans. I could feel how hard his cock was already.
I cupped his balls through his boxers. I rubbed and kissed the outline of his cock, then hooked my fingers into his boxers and pulled them down exposing Tony's very hard cock.
I then kissed his thighs, his balls. I licked his shaft. took his cock head into my mouth and sucked lovingly. Tony must have liked what I was doing, because he was moaning.
I pulled off of his cock and stood up. I reached behind me and unzipped my dress and let it fall to the floor. I think Tony liked what he saw because his cock jerked when I did it.
I kissed him lightly on the lips and whispered in his ear. "I want you to make love to me Tony." He looked into my yes and asked if I was sure.
I smiled, nodded, and said "Please."
I went and got the lube from my bedroom. I was shaking from nerves and anticipation. As I returned he held his hand out "Give it to me."
I handed him the lube. He then told me to take of my panties. I slide them down my legs and stepped out of them. That left me standing there in nothing but a bra, garter belt, stockings and heels.
As he opened the tube he "ordered" me to lay across his lap. I laid across knees face down. He had to feel my hard clitty pressing into his thigh.
He scooped some lube onto his fingers. Inserting one finger, working the lube into my ass. OH MY that felt good. Then he worked a second finger into me. I was moaning and grinding my cock against Tony's leg.
Tony then worked a third finger into my ass, trying to stretch it so I could eventually take his huge cock. All that stimulation was getting to me and without warning I came all over Tony's thigh.
I was worried that Tony would freak or at least get mad. He slapped my ass and then pushed me off his lap. He told me to clean his thigh. I was licking my cum from his leg, then went back to licking and sucking his cock for a few minutes.
Then he took some lube and worked it all over his cock. He told me to get onto all fours. I obeyed and got on my hands and knees right there on the living room floor.
Tony got behind me. He asked once more if I was sure. I took several deep breaths and told him I was ready. I felt him position his cock at my opening. The head started pushing against my ass.
I was pushing out hoping it would ease the pain. Even though I knew there would be pain, I wanted this so bad. I wanted to be Tony's woman in every way.
OH GOD IT HURT! Tony was going slow, trying to be gentle. It still was more pain than I had ever felt. Finally with one big thrust his cock head passed my anal ring. I was seeing starts from the pain.
Tony stopped to let me get use to having his cock in my ass. After a few moments He pushed and a little more went into me. I was breathing hard trying to block out the pain.
He pushed again and now I had almost half of his 10 inches inside me. I already felt stuffed, I could not take any more and I told him to stop. He pulled back and then pushed forward again.
He would grunt as he pushed forward, and I would groan as he pulled back. Tony started working more and more into me, at 8 inches he had to stop. I could not take any more.
He asked me if I wanted him to stop. Such a nice guy. "No Tony, I have thought about you making love to me so often. PLEASE, don't stop now."
He started to moan as he set into a steady rhythm. In and out, In and out, in and out. After awhile the pain started to subside. I was actually starting to feel pleasure. I was enjoying pleasing my man.
I closed my eyes and concentrated. His strong hands on my hips. His extraordinary cock working in and out of my ass. He was picking up the pace, mumbling about how tight I was. About how good it felt to fuck such a pretty girl. I found myself pushing my ass back to meet his thrusts.
Tony was sweating and breathing hard. He had been fucking me for about 20 minutes. I felt him tense up and Then he let out a combination groan and growl. I felt his cock throb in my ass then he let go and came hard in my ass.
When I felt him cum inside me, it sent me over the edge and I came too. He stayed in me until I felt him start to soften. There was a pop when he pulled his cock free. WOW I had done it. I had taken Tony's cock in my ass. I would be sore tomorrow but it was so worth it.
I kissed him and excused myself. I went to the bathroom to clean up. I could not believe the amount of cum Tony had deposited into my ass.
When I was done, I reapplied my lipstick, wet a washcloth and returned to the living room.
I sit down beside him. I kissed him again the went about washing off his messy cock.
He started passionately kissing me again and I felt him hands playing with my nipples. Soft gentle caresses at first. then he was rubbing hard. pinching them. While he was mauling my nipples, my hand went back to his cock.
My little hand could barely reach around his cock. I started working it up and down his shaft. He was already getting hard again.
When I broke the kiss Tony had his hand behind my head. He guided it down to his cock. I kissed his cock. Licked the opening. Swirled my tongue around the head. After having it in my ass, it did not seem quite as big as I engulfed the head and started sucking.
My head was bobbing up down on Tony's cock. My hand working up and down the shaft. Tony's hand was stroking my hair as I was sucking his cock. He was not forcing anything, just caressing my hair and letting me work at my own pace.
In this position I could not deep throat his cock but I was sucking for all I was worth. It was not long until I was reward with a mouthful of cum.
After I swallowed it all I licked the cock head clean. Then I snuggled against Tony with his arm around me. I asked him if he was glad he came over.
He replied "I had a wonderful time, you were great." Then he kissed me again. We made out for a little while longer then he said he really needed to go. As I watched him dress, I slipped my dress back on.
"Tony, Am I your girl?" I asked.
He smiled. "Angel you were incredible but I want a real girlfriend."
He seen that I was crushed. He took me in my arms and said "I am sure we will see each other from time to time." Then he kissed me good bye and left.
While I was kind of sad and felt rejected, I smiled to myself. I had just had a night of romance and sex, that most girls just dream about. _________________________________________________________
More to come, especially if I continue to get positive feed back.