Date: Wed, 26 Nov 2008 13:16:29 -0500 From: Andi Subject: Andi's Adventure Part 02 (TG-High School) 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 cute 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. HAPPY THANKSGIVING EVERYONE!!!!! Andi's Adventures - Part 02 It was the Tuesday before Thanksgiving and Jamie and I were in our spot in the Library. He was saying that he really did not want to go with his parents to visit family over the Holiday. I told him that he could stay with me and My Mom if he wanted to. He thought about it and said he doubted that they would let him. I convinced him to at least Ask. When Mom got home from work that night I asked her if it was ok for Jamie to stay with us, she said of course. Jamie called and said his Mom wanted to talk to my Mom. I listened as my Mom assured her it would not be any trouble for him to stay. They talked a little longer and after Mom hung up, She told me about how Jamie's parents had been needing to get away, just the two, and this would work out well. They could spend Thanksgiving with her parents and then go to the mountains for a romantic weekend. ______________________________ Wednesday afternoon as Jamie and I were leaving school, I saw Tony leaning against his car talking to some cute senior. I just stopped and stared as he leaned in and kissed her. Jamie asked "dude what is it with you when you see that guy? You always seem to space out when ever he is around." I gave a nervous laugh and said "I have no idea what you mean." He said "yea right" then let it go. We spent the afternoon playing video games, eating potato chips, and drinking Mountain Dew. Mom came home just after seven and I introduced her to Jamie, she told him she was pleased that I had brought a friend home for a change. Around 10 O'clock., She said to have fun as she headed up the stairs. After she left we were flipping through the channels and came across an R rated moving that had some nudity. There was a girl in the movie who looked a lot like Susan the girl Jamie had a crush on, long brunette hair, green eyes, small breasts and long legs. I asked him why didn't he invite Susan out? He laugh and asked what was the point? Even if she went out with him he wouldn't know what to do. He got a serious look on his face, "I Am a virgin, I have not even kissed a girl yet." I told him "don't feel bad I have not kissed one yet either." He laughed, "I wish I had one of those blowup dolls to practice on." I added "Yea I have heard that girls loves a guy who knows how to kiss." Where I had heard that I had no idea. As we watched the movie I got to thinking, Jamie is cute. He was 5'11", black curly hair, kind of skinny but has a nice smile and seems so gentle. By now it was after 1 AM. Another boring movie came on and we decide to go to bed. My bed was big enough for both of us. As Jamie was brushing his teeth I put on a pair of jogging shorts and laid down, When Jamie came out of the bathroom he stripped to his boxers, I could not help but take a glace. I could see the outline of his limp cock. We laid in bed and talked. He asked me if I ever had a crush on someone like he had on Susan, I just said yes but they have no clue about the way I feel (I was thinking of Tony but dare not tell Jamie who it was). _____________________________ Mom woke us up around 9 AM. She said she had volunteered to work the evening shift at the hospital. So we were going to eat Turkey around noon so if we wanted anything for Breafast to grab a bowl of cereal. We put on shorts and T-shirts and headed for the Kitchen, everything smelled great so we decided to just wait and eat lunch. We got a glass of Orange juice and headed to the living room to see what was on TV. We quickly got bored watching the parades so we headed back to my room to play a game on the computer. We ate a wonderful meal then helped Mom clean up and do the dishes. We were watching football when she left around 2:30 and said she would be home around Midnight, the number was on the fridge if we needed to call her. Jamie asked me if they were any parental controls on the computer. I told him that no , my mom had no idea how to work the PC. So we went back to my room and was looking at pictures of girls. We found a web site with videos of couples making out, a couple of were two girls kissing, one even showed two guys kissing. I noticed Jamie would occasionally rub his cock through his shorts. I was doing the same. We progressed to videos of girls sucking cock. Jamie was saying he wondered how great that would be. Then he sighed, got a sad look on his face and said I can't even find someone to kiss me, where would I find someone that would do that. Seeing that look on his face broke my heart and I decided right there that I would help him out if he would let me. So I took a deep breath and then told Jamie he was my best friend and asked if he could he keep a secret? He said sure. I told him "it would be better to show you than to tell you. but you have to promise that no matter what you think you will not tell anyone." "What is this secret?" "Just watch some more porn and I will be back soon." I left him sitting at my computer with a confused look on his face. I ran to my Moms room. I knew just what I wanted to wear. I dug in her drawer and found the light blue bra that fastened in the front, the matching lace panties and lace garter belt. Some white stockings, a simple white skirt that zipped on the side and came to just above the knee. A black blouse that buttoned up the front. I went to her bathroom and took a quick shower, sprayed myself with moms perfume, applied lipstick and some eyeliner. brushed out my hair and tied it back into a ponytail. I was getting dressed when I had to go back into the bedroom and get some pantyhose to stuff my bra, giving me some cleavage. I was not just going through the motions and hoping just to get it over with this time. I wanted to look my best for Jamie. I looked in the mirror and thought that I did not look to bad. To bad Moms feet was so small I did not have any heels to wear so I walked back to my bedroom in stocking feet. I paused outside my bedroom door, what was I doing, what if Jamie freaked? What if he was repulsed by the fact that I dressed like a girl? I know he promised not to tell, but what would it do to our friendship. I almost chickened out. Then I heard call out "is that you? What is taking so long?" I took a deep breath to steady my nerves. Opened the door and entered the room. Jamie looked up and gasped. "What the hell?" "Damn what are you doing?" I guess his reaction threw me. I felt like crying, He must have seen the tears welling up in my eyes because he took a step toward me like he wanted to comfort me but then stopped. 'This is your secret? I would have never guessed, how long have you been doing this?" I whispered "just a couple of months." He was looking me up and down. "Are you gay?" "I am not sure what I am. Maybe I am Bi I don't know" Finally he smiles "well you don't look to bad, actually you are kind of cute, am I the first person to see you like this?" I lied. "Yes you are, I felt like I could trust you, please don't tell anyone. If you feel uncomfortable, I can go change back and we will never talk about it again." He thought about it for a moment and said "No, its ok you can stay dressed, like I said you are cute. How often do you do it?" Almost every afternoon, well I do not dress all the way like this to often, usually just bra and panties." He sat back down at the computer and I went to the bed, smoothing out my skirt as I sit down and crossed my legs, flashing my stocking tops. We went back to looking at videos on the computer. I would glance at his crotch occasionally and I would catch him looking at my legs. Luckily I have very little body hair but I realized I may have to shave them soon. By now it was 6 and the sun was going down. We decided to go the kitchen to get something to drink. I lead the way and wondered if he was checking out my butt. We went back to the living room, turned on the radio and sat on the couch, I noticed that Jamie sit on one end and I sat on the other, as much distance between us as possible. He was staring at me, then suddenly asked "Does dressing up make you horny?" I thought how crude then realized that yes this time I was getting hard, my cock is only 4" hard so it was easy to hide it. So I gave him the short answer and said yes. "So what do you want to do now?" He asked. I seen an opening and decided to take it. "well you know what we were talking about last night? About having someone to practice kissing with?" You should have seen the look in his eyes as he realized what I was proposing. I told him we could stop at any time if he felt uncomfortable. He did not answer yes or no but just stared wide eyed at me, So I scooted over so I was sitting close to him, our legs were touching. He was wearing a T-shirt and shorts, His bare leg against my stockinged leg was generating heat where it touched me. Even though I had been used by 4 different guys in the last few months, I realized that it was true, I had never kissed any of them. I clumsily leaned over and kissed him on the cheek. Then I kissed him lightly on the lips. I pulled back and looked him in the eyes...this time he kissed me, lightly at first, then a little more roughly. I broke the kiss and said slow down we have lots of time. We kissed again and continued to kiss for several minutes. I felt his tongue enter my mouth. We continued to kiss as our tongues wrestled and explored each others mouth. We broke the kiss, each of us breathing heavily. I excused myself and went to the little girls room. I used this time to get my breathing under control and to touch up my lipstick. Now there was a slow romantic song playing on the radio. I remembered what it was like dancing with Tony that time. I asked Jamie if he wanted to dance, of course he said he did not know how. I told him that he had better learned before he was faced with the chance to dance with a real girl. He blushed but stood up and offered me his hand. Such a gentleman. He hesitated so I got close to him and put my arms around his neck like I did with Tony. Shyly he put his arms around my waist but did not pull me close. We swayed to the music. I looked into his eyes and he kissed me again. We danced and kissed through 3 songs until a fast song started playing. He took my hand and lead me to the couch. After he sat down he pulled me onto his lap. I looked into his eyes and said that "although I had nothing to compare it to, I thought he was a really good kisser." He smiled and kissed my lips again. I felt his hand resting on my thigh as we were making out. His lips left mine and he kissed my cheek, my neck, he even started to nibble my ear. Wow he was catching on fast. My cock was rock hard in my panties. Then he surprised me by pushing my skirt up and sliding his hand over my stocking top and started caressing my bare thigh. His other hand started to squeeze my "breasts" through my blouse. I was sucking on his tongue as he kissed me. I felt him starting to unbuttoning my blouse. He slide the blouse down my shoulders exposing my lacy blue bra. He was still caressing the bare skin above my stockings top. We were both breathing hard. He pushed one hand under my bra and started rubbing my nipples. Except for the one time that Jerome had mauled my nipples, this was the first time they had been played with. I did not know how sensitive my nipples could be as he rubbed and pinched them. I felt him reach behind me fumbling to unhook my bra. I broke the kiss for a minute and told him the hooks were in the front. He said take it off. I unhooked my bra and the balled up pantyhose fell to the floor. In his lust Jamie did not even notice. He surprised me when he leaned in and started sucking on my right nipple while rubbing and pinching the other one. OH GOD what a feeling. That is not all. His other hand had worked his way up my thigh and started rubbing my cock through my panties. I was breathing hard and if he did not stop soon I was going to cum all in my panties. I told him "Jamie if you keep that up I am going to cum soon, will you be ok with that?" To answer me he switched which nipple he was sucking on and bit down lightly, he also slipped my panties down exposing my "clit". As he was sucking and biting my nipples he started stroking my cock. I let out a loud moan and came all over his hand. He pulled my panties back up and rubbed my cum all over the crotch of the panties. Making them all wet and sticky. I broke the kiss and told Jamie I needed something else to drank. He let me up off of his lap, I slipped my blouse back on and just tied the bottom in a knot. I went to the kitchen to get us some cokes. I took them back to Jamie and handed him one. He was looking at me with those big brown eyes. Dreading his answer I asked "so do you regret anything we have done so far?" He looked at me sheepishly and said that he really liked what we did. I sit close to him and he slip an arm around my shoulder and we just set there finishing our cokes. Finally I got up and took his hand and said come with me. I lead him back to my bedroom. I pulled his T-shirt over his head and went back to kissing him hungrily. I pushed him back on the bed and stepped back. I took my blouse back off, then unzipped my skirt sliding it off and folding it putting it and my blouse on the chair. He was staring as I stood there in wet panties, a garter belt and stockings. I reached down and grabbed his shorts, pulling them and his underwear down with one motion. He was hard and I judge his cock to be 6" not big, but not bad. I was so eager to please Jamie I took his cock in my mouth in a single motion. I started working my mouth up and down his shaft. I would vary the speed. Some times I would quickly bob my head up and down his cock. Some times I would take it slow. he was moaning loud. It was his first blow job and I did not think he could hold out much longer. I increased the pace. I felt him start pushing his hips up trying to force it further in my mouth. "Oh Andi that feels so good". I felt him tense up and then he came. Without thinking I started swallowing his cum. When he was finished I pulled my mouth off his cock and gently started licking he deflating cock. As I raised up I could see he was already a sleep. Men. LOL I crawled up and laid beside him. My head resting on his chest as I drifted off to sleep. ___________________________ It was after 11 when I bolted upright in the bed waking Jamie. He looked around confused until he remembered what we had did. I told him I needed to clean up before Mom got home. That's when I remembered that I had left my bra and the pantyhose I stuffed it with in the other room. I ran to the living room and grabbed everything and came back to get the blouse and skirt. As I was hanging up the blouse and skirt, That's when I realized My panties were encrusted with dried cum and there was no way I could wash them and replace them before my Mom came home. I put everything but the panties back as best as I could. As I was putting the stockings and garter belt back in the drawer, I grabbed a pair of pink lacy panties and took them back to my room. I hid both the pink and the light blue panties under my mattress. slipped on some shorts and a sweatshirt and went to find Jamie. While I was returning my Moms clothes to there proper place, he had straightened up the living room, and took the empty drink cans back to the kitchen. We were sitting on the couch when we heard Mom pull into the driveway, that's when Jamie almost gave me a heart attach. He said "Andi, your face" aan I realized I still had make up on. I was closing the bathroom door as I heard Mom saying hi to Jamie and asking where I was. I hurriedly scrubbed my face and removed my lipstick. I hoped I washed off most of the perfume smell as well. I returned back to the living room to say hi to my mom. "So have you two been good tonight?" She asked. "Oh Mom" I said as I almost choked. "Well its late, I am tired and going to bed. do not stay up to late" After she left Jamie and I both laughed so hard that we almost cried. We watched another boring movie neither wanting to mention going to bed. We both knew that things had changed between us. I just hoped that Jamie did not regret what we had done when he had time to think about it. When the movie ended Jamie took charge and turned off the TV. Jamie used the bathroom first tonight. While he was in there I searched my closet for a T-shirt I had not worn in a long time. It was like 3 sizes to big for me and hung to my knees. I took the pink panties out from under my mattress and waited for Jamie to finish. When Jamie came out in just his boxers, I did not try to hide the fact I was looking at his cock and I caught myself licking my lips. I showered and brushed my teeth. I slipped the panties on and pulled the T-shirt over my head. When I went back to my bedroom, Jamie had turned out the lights but the moon was shining through the window. Jamie was laying on the bed watching me. I crawled in bed with Jamie, He took me into his arms and we started kissing again. I felt him starting to hump my thigh getting hard again. "Oh you naughty boy" I said as slide down the bed. He had taken his boxers off before he got in bed. This time I took it slow. I bathed his balls with my tongue. slowly licked his shaft like a lollipop. I started sucking on his cock again. I realized just how much I enjoyed doing this for someone when I wanted to, not because I was being forced. I was sucking the head as I was working my hand up and down the shaft. He seemed to like that. He lasted longer this time but he still came quickly. He did not cum as much this time so I had no trouble swallowing it all. I slipped off the bed and locked the door. I did not want Mom to accidentally walk in on us in the morning. _________________________________ I woke Jamie up the next morning by sucking his cock. I figured it would be the only time we could play since Mom would be home all day because she was off until Monday. _________________________________ I gave him one last blow job Saturday night. His parent came by around noon on Sunday to pick him up. They asked if he had been good and mom told them he was no trouble and that he was welcome any time. Jamie's mother said that maybe I could stay with them some time.