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 yr. old cross dresser. 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 Adventure Part 04
Brian, Jason, and Jerome was leaving me alone, I guess everyone was busy with Christmas approaching.
Jamie had finally mentioned what had happen at Thanksgiving. He admitted that he really enjoyed it and would not mine doing it again.
We had a history project that we were working on. So I decided to take initiative. I asked him if he wanted to come over and work on it together. He called his mom and she said ti was fine and that she would pick him up on her way home from work. Jamie said she got off at 5.
We settled on the kitchen table to do our work. One of us would have to go to my room and check something on the computer ever so often.
We had been working for over an hour and it was my time to look something up. After I found what we needed. I started printing it out. While I was waiting I got a naughty idea.
I quickly undressed and slipped on my green nightie and matching panties. Decided to leave my hair down for a change. Applied a liberal coat of lip stick, grabbed the printout and headed for the kitchen. I struck a sexy pose in the doorway and waited for Jamie to look up.
When he seen me he broke out into a huge grin. I told him I thought we had worked hard enough and needed a break. He stood to meet me and kissed me on the lips. He said I looked really good in green.
We were kissing and making our way back to my bedroom. As soon as we entered the bedroom I removed his t-shirt. then went back to kissing Jamie and playing with his chest. We made it to the bed. As I was unsnapping his jeans. He took them off and he underwear followed.
He told me to lay on my back. I watched as he climbed on the bed and got on top of me. He leaned down and started kissing me again. I felt his cock slip between my legs. he started making a fucking motion jabbing his cock between my legs enjoying the friction we were creating.
He moved up the bed and straddled my head. He started rubbing his cock over my face smearing it with pre-cum. I opened my mouth and he slid it in.
He started fucking my mouth faster and faster. I was griping his ass as he fucked my face. I started running my hand between his butt cheeks. I inserted a finger in his ass and worked it in and out. That sent Jamie over the edge and he shot his cum into my mouth.
I swallowed most of it but kept some in my mouth. He got off of me and laid down beside me. I kissed him and forced Jamie's cum into his own mouth. he jerked away and I thought maybe I had crossed the line but saw him licking his lips tasting his own cum.
We kissed some more, our hands roaming over each others body. I wanted more but he said his mom would be by soon to pick him up. I put on a sweat suit to cover my lingerie and we went to wait on his Mom.
I waved to Jamie Mom as he was getting in the car. I watched them drive away.
Oh Wednesday we were in the Library talking about what video games we were going to play when he stayed over, when Tony came in to return the book he used for his report. He was smiling when he came over to us.
"Hey Kido, I got an A on my report about Robert Frost, thanks for helping me find that book."
God Tony was so handsome, I caught myself staring at his crotch, I quickly looked up hoping that neither Tony nor Jamie seen where I was looking.
"Your welcome Tony but you did the work that earned you that A."
"Well still I wanted to thank you" as he flashed that dazzling smile.
I heard myself saying "If there is ever ANYTHING you think I could help you with , just let me know" Oh God I was openly flirting with him. In front of Jamie.
After Tony left, Jamie looked at me and mouthed "SLUT", then laughed showing he was joking.
The first day of Christmas break I slept late. Mom had to work so I ate breakfast and watch TV.
Jamie had said to call him and we would try to work something out. He asked if I had any plans for tomorrow and in my sexiest voice I asked "What do you have in mind?"
He laughed and said "I was thinking about seeing if you wanted to go tot he mall, but if had other ideas I am all ears."
"Baby I have seen ALL of you, You are most definitely more than just ears." I playfully answered.
That night I asked my Mom if I could go and she said sure. She also told me that she had a date this weekend wit a guy she had met at the hospital.
Jamie's Mom dropped us off at the entrance to the mall. Being less than a week before Christmas it was full of people. I had saved up some money from my allowance. Mom also gave me $100 to do some shopping, Since my Mom was the only one I would be buying a present for I thought that was very generous but she told me to buys something for myself.
Naturally the first place we went was the video game store. Then the comic book store. As we made the rounds. Jamie bought some things for his family.
I told Jamie I was going to look for a dress for my mom. He told me he had some thing he wanted to look for and we agreed to meet back at the food court.
I found this small dress shop, I was looking around when a sales woman approached from behind. "May I help you Miss?"
I looked around realizing she was talking to me. When she seen my face she stammered out "Oh I am sorry sir." It dawned on me that with a little work I might be able to pass as a girl in public.
I did not find anything in that store, but in Belk's I found her a really nice, conservative dress I thought she would like. I also wondered just what i would look like in it.
Jamie ask why it took me so long. I just told him I had lost track of time. We at some no name restaurant. Jamie ordered a burger, I ate a salad. I had decided to lose a few pounds, I needed to slim down.
While we were sitting on a bench waiting for Jamie's Mom to pick us up, I spotted a shoe store. I told Jamie to watch my stuff I would be back in a second. I went in and pretended to look at some sneakers. Then I went to the discount rack. I spotted some black open toed sandals, they were the same size as the black heels of Shannon's that I had worn a couple of times. OMG the heels were 4 1/2 inches.
I checked the price, they were discounted by 60 %, I decided I had to have them. I also decided to buy some simple white flats. I worked up my courage and took them to the cash register. The girl that rang them up looked at me funny but just rang them up and said Happy Holidays.
I asked Mom if Jamie could come over. She agreed. So two days before Christmas Jamie rode his bike over to my house. He arrived around 10 AM.
We talked for a bit, finally Jamie asked me if I wanted to fool around. I stood up and striped revealing my black bra and panties. We quickly started making out.
We eventually ended up in my bedroom. When Jamie was naked I gave him my best smile as asked him would he do something for me. "Sure" he replied.
I reached under the mattress and took out the pink lace panties. "Put these on for me, please!!"
He hesitated then said ok.
Oh wow he looked hot in those panties.
We were laying on our sides making out, our bodies rubbing against each others. My hand caressing his lace covered cock.
He unhooked my bra and started sucking on my nipples. he was sucking and biting my nipples his hands groping my ass.
I felt him humping my leg as he was basically trying to chew on my nipples. Jamie surprised me when he kissed his way down my body.
I figured he would stop when he got to my waist, but again I was surprised as I felt him kiss my small cock through the panties.
I was already hard but I felt my cock lurch as Jamie started licking me through the satin material. He engulf the head in his soft warm mouth. While I hade given blow jobs to several guys in the passed, this was the first time anyone had done it to me.
No wonder guys loved to have their cocks sucked, this felt incredible. In just minutes of Jamie sucking and licking my cock I was filling my panties full of cum. As my cum soaked through my panties, Jamie continued to lick and suck.
Finally he scooted up and laid beside me, "Did I do a good job?"
I kissed him deep and told him "it was incredible but I was surprised you did it."
He smiled and said "I just wanted to make you feel good for a change."
I pulled him on top of me and stated kissing him and sucking on his tongue. I felt him start humping my crotch. He was making me hard again.
I pushed him off of me and he looked at me with confusion and hurt in his eyes.
I reach downed and slipped his cock head free. I leaned down and licked the head with long slurps.
I looked at him and said "Since you made me feel so good, I want to make you feel even better" Breathing hard, I huskily asked said "Please Jamie fuck me, I want to feel you inside me."
He asked "Are you sure?"
I smile and nodded.
I slipped off the bed and got some Vaseline from the bathroom.
I removed my panties and scooped some onto my fingers and started working them in and out of my ass. Jamie looked like he was in a daze as he watched me. I rubbed some onto the head of his cock, then asked "Are you ready?" He just nodded.
I got on all fours and he got behind me. I guided his cock to my ass. His cock head pop into me without any problem. I heard him say "OH That feels so good."
It was his first time so he was anxious. He was pushing in and out quickly. I told him "slow down Jamie, relax, take your time and enjoy it."
"Oh enjoying it does not begin to describe it." He moaned but he did slow down the pace. I was starting to enjoy it myself, his cock was not as big as Brian's or Jerome's. It did not hurt at all. In fact it was feeling real good. I started rolling my hips and Jamie could not help it he started fucking me faster and faster.
It was not long until his cock throbbed and he came. As he was shooting into my ass, I felt my balls tighten and I came a second time in less than a 45 minutes. We collapsed on the bed and tried to catch our breath.
We had a long kiss goodbye. He was going to be busy with family stuff until after Christmas but I was sure we would get together again as soon as we could.
Mom had started dating a man named Mike. He seemed nice enough and I was glad Mom was going out and having fun.
On new year's eve Mom was going out with Mike and Jamie's parents had plans so we talked them into letting Jamie stay at my house.
At 8 PM, Mom and Mike were leaving the house as Jamie's parents were dropping him off. All three of our parents jokingly told us not to get to wild tonight. If they only knew.
We spent a nervous hour watching TV, making sure our parents did not come back for something. Then we headed for my bedroom. I asked if he enjoyed wearing panties last time and he said "OH YEA."
I handed him the green nighty that I wore last time and asked him to wear it. He agreed.
I said I will be back and went to my Moms room to get ready. I put on a cream colored slip and white satin panties. I grabbed a tube of lipstick and headed back to my room.
Jamie was sitting on the bed. Jamie looked hot in the green nightie with spaghetti straps and matching panties. I stood there applying my lipstick watching him. I told hit to stand up, I Applied lipstick to Jamie's soft lips.
Then we kissed. A deep passionate kiss. My hands found my way to his ass. I was groping his ass as we kissed. Our hard cocks were grinding together as we were making out.
Jamie is the first and only person to ever kiss me during sex. Right now his kisses were driving me wild.
As we continued to kiss we fell across the bed. I eventually slipped one of the straps of his nighty over his shoulder exposing a breast.
I kissed my way down and starting sucking on his nipple. I repeated the process with the other nipple making them hard. His breathing was increasing and I could feel his hard cock against my tummy.
I continues working my way down Jamie's body. Skipping down I kissed his left leg behind the knee. I lick a ticklish spot because he giggled.
Then I was planting sloppy wet kisses on his creamy thighs. I started licking his balls. Sucking one into my mouth and washing it off with my tongue. I was licking up the shaft and I heard Jamie moaning and panting for breath.
I put a hand on each thigh and spread his legs as I started deepthroating him. The room was filled with sucking sounds. moaning and heavy breathing.
It was not long before I was rewarded with a nice load of cum from my lover. My Lover? Did I just think that? I heard Jamie sigh as he started to relax.
I raised back up to where I could start kissing Jamie. I was kissing him and stroking his hair. I knew he could taste his own cum as we kissed.
After a few minutes Jamie fixed the straps of his nighty and Said "My turn."
He started moving around on the bed, the next thing I knew I was feeling him lick my cock head through my panties. He was licking the head, cupping my balls and squeezing them through the panties. God that felt good. I am usually the one doing this to someone else. I really liked it the last time Jamie did it.
Jamie surprised when I felt him slip my panties down and suck my cock into his mouth. OOOOOOHHHHHHHHH YESSSSSSSSS. He started working his mouth up and down my 4 1/2 " cock.
Since this was the first time I received a true blow job. I tried to hold back, honest I really did try, but Jamie was doing a great job and I came in his mouth. This time he raised up and kissed me, letting me taste my own cum and our lipstick.
While he was sucking on my cock, he had time to rest and recharge, I felt his cock getting hard against my thigh. We were kissing and his hands were cupping and squeezing my ass.
By now he was nibbling on my ear. Andi he whispered, "Can I uh...you know, do what we did last time?"
"Jamie you can do anything you want to do, I want to please you."
He said "let me get the Vaseline."
When he climbed back on the bed I slipped my panties off and laid on my side. I felt him start to work his fingers in and out of my ass. The head of his cock slip in me easily.
He laid their for a few seconds enjoying the tightness of my ass. Then I felt him start to push in and out. He work his cock in and out of me at a slow steady pace. Oh my it was starting to feel good.
Jamie started picking up the pace and soon I felt his cock start throbbing and then he came in my ass.
We lay there catching our breath. He was kissing my ear and the back of my neck. Reaching around he was rubbing and cupping my breasts through the slip I was wearing.
We were both dehydrated and decided to get something to drink and watch the count down from Time Square. As Jamie was getting the drinks I went to the bathroom to clean up.
We sat on the couch and watched TV. When they started the count down, Jamie pulled me to my feet and as they got to Midnight He kissed me deep and passionately. Breaking the kiss He said "HAPPY NEW YEARS."
After the show went off we knew we still had over an hour before Mom was suppose to get home. I slide off the couch and started kissing my way up his legs again. Eventually kissing his cock head through the panties.
I slid them down to his knees and lovingly took his cock back into my mouth. After he got hard again, I was still on my knees, I turn around pointing my ass toward Jamie. Seductively looking over my shoulder I asked"Fuck me Jamie." I licked my lips and said playfully "I have not been fucked this year."
Jamie was happy to oblige, He came up behind me and slide his cock as deep into my ass as he could. I was still lose from earlier so he had no trouble entering me.
Even though he had cum twice already tonight, it was not long until he was panting and slamming his cock into me. When he thrust forward, I would push my ass back to meet him. I could not believe it, I was going to cum from being fucked.
My body started shaking as I shot cum all over the floor. After that, it only took seconds for Jamie to cum deep into my ass.
After he pulled out I turned around and lovingly started cleaning his cock. He must have been spent because after spending 15 minutes licking and sucking his cock it was still not completely hard.
I cleaned up the mess I had made on the floor where I had cum.
We straightened up and changed back into shorts and T-shirts and were sitting on the couch watching CNN where they were showing recaps of all the New Years eve celebrations.
Mom must have had a good time with Mike because she was drunk and giggling when she came in the door.
She finally went to bed. Jamie and I soon followed.
we were both tired so after I put a t-shirt and panties on we snuggled on the bed and fell asleep quickly as Jamie nuzzled his cock against my ass.
The New Year had started with a bang.
More to come, especially if I keep getting positive feed back. Thanks to everyone who has written to me so far.