I had just turned 16 and I was really into moms clothes and makeup. I was a very petite 4'11 and slim, very feminine features and passable when dressed up and makeup applied, I had shoulder length blond hair. Mom noticed I was identifying as a girl more than a boy and felt it was time to teach me about the birds and the bees. She decided to send me to my uncle Joe for the summer for training. I always liked uncle Joe, he was a very big man 6'4 and fat but very friendly and kind. Mom drove me to uncle Joe's place and he was there to greet me with a big grin, as mom drove off uncle Joe took me by the hand and led me inside his house, I noticed his hands were huge. I went with uncle Joe inside his house and he sat me on his couch and told me he would be right back. He walked into another room and came back with a suitcase and sat next to me. Now I know your name is Charles but now your name is Cindy. these are your new clothes, he opened the suitcase and it was full of panties , bras, and frilly dresses. Then uncle Joe said, your mom told me all about you wearing her clothes and makeup and it was time for you to be a woman sexually too, this summer I will teach you. Then uncle Joe took me upstairs to a bedroom with a four post bed with pink sheets and blankets and a fully stocked makeup table in the corner. He said ok Cindy this is your room now change from those boy clothes into some girl clothes and put on some pretty makeup and come down to the couch. I peeled off my jeans and shirt and put on pink panties and a very short pink nightie. I felt just like a girl. Next I sat at the makeup table. There were lots of different colored lipstick but I liked the pink lip gloss. I applied it on my lips, then I put on some blue eyeshadow and black mascara. I headed back downstairs but I noticed this time uncle Joe was watching TV and when I got closer it was porn playing, then when I turned to uncle Joe he had no pants on and was sitting there on the couch stroking his very hard cock. I was staring in shock with my mouth open when uncle Joe said come here Cindy and sit next to me. I glanced at the TV screen and saw a woman sucking a man's dick. I sat next to my uncle as he said just watch the movie honey as he continued to jerk off. His cock was very long and fat, much bigger than the one in the movie. suddenly uncle Joe grabbed my small hand and made me grip his big shaft, it was so fat I couldn't get my hand around it. It was so warm and hard. Uncle Joe groaned as I grabbed his cock and said spit on your palm honey and then grab me again. I spit on my palm and once again grabbed his cock shaft. Now honey pump your hand up and down for uncle Joe. I began sliding my hand up and down his cock, with his free hand he pulled me closer. I somehow enjoyed it. then after a while I felt uncle Joe's hand on the back of my head, he pushed my face closer to his cock, Honey get a closer look. By now my face was inches from his cock, I noticed a glob of precum appear from his pee hole and stared at it Uncle Joe said go ahead honey taste it if you want. Just out of curiosity I stuck my tongue out and licked it, surprisingly I liked it, it was sweet. Do you like it honey? Yes uncle Joe it tastes sweet. Then you will love my cum, it's even sweeter. With that I felt uncle Joe's hand on the back of my head push real hard leaving me no choice but to part my pink lip glossed lips and let his oozing cock head in. Uncle Joe groaned as his cock entered my mouth. Now Cindy this is something your boyfriends will want, it's called a blowjob. Now lick your pretty lips and slide them up and down. I did as my uncle instructed, I was learning a lot. After a while uncle Joe announced I'M CUMMING, and held my head there. suddenly gush after gush of warm thick sperm filled my mouth, uncle Joe was right it was very sweet. Uncle Joe bellowed swallow it honey, it was hard to keep up with but I managed to swallow it all. I loved the whole experience. The next day uncle Joe summoned me to the couch and sat me down. Now Cindy there are a few ways a T girl like you can pleasure her lover, This is another way. Uncle Joe then opened a box with different sized dildo's Now honey you have to learn anal sex and we have to get you stretched out for your first lover. Each night this week slide a bigger dildo up your ass and keep it there all night, then he handed me a tube of lube. I did as uncle Joe instructed and the end of the week came soon and I had a 10 inch dildo up my cute little bubble butt by then. Ok now honey kepp the dildo in until this afternoon until your lover comes over. About 2 pm the doorbell rang and uncle Joe opened it to reveal an old man with a huge saint bernard on the end of a leash. Hi clem come in , Duke looks horny , good cause Cindy needs to learn anal and I figured Duke is the perfect lover to break her in. Clem slyly snickered as he led big Duke to the center of the living room. Cindy honey why don't you get off the couch and come over here and look under Duke's belly at his cock, you might have to jerk him a little bit to make sure he's hard for you. I got off the couch and went to Duke's side on all 4 peeking under his belly, I gasped when I saw a 10 inch really fat ugly veiny dog cock. Uncle Joe said now kiss his cock honey he will be your first anal lover. I did as uncle Joe said and I kissed Duke's ugly big dog dick, it twitched when I kissed it. I stared at it intently wondering how this huge cock would fit up my tiny ass. Uncle Joe handed me a tube of lube and told me to lube up Duke's cock real good. As I was under there lubing up Duke's cock my uncle and Clem removed the big dildo from my asshole which was still gaping. Uncle Joe got a popsicle from the freezer, lubed it up and slid it up my ass to numb it. Then uncle Joe told me to get out from under the dog but stay on all 4, he put a collar on me and a leash. Then he put a ball gag in my mouth telling me the first time hurts a lot and he was afraid of loud screaming. Uncle Joe led me by the leash until I was on all 4 directly in front of Duke. Clem led Duke by his leash to mount me. Duke immediately jumped on my back almost causing me to collapse under his heavy weight and started jabbing his cock at my ass cheeks but missing the hole every time until Clem grabbed his big lubed dog cock and aimed it at my lubed gaped ass hole. Duke was brutal, he shoved his entire huge dog cock up my ass in one motion. I screamed around the ball gag and my eyes opened wide. Duke must have been real horny because he started humping like a jackhammer all the way in and most of the way out. It hurt for the first 5 minutes or so then I started to get pleasure from his big cock rubbing my prostate, it felt real good. Uncle Joe noticed a look of pleasure on my face and asked me if I liked i. I nodded yes as Duke continued his anal assault .. Uncle Joe removed the ball gag to me, sighing yes. C'mon Duke honey fuck me good. Suddenly I felt Duke's knot start to grow inside my ass hole, it hurt as it swelled but once he started shooting his huge load of warm dog sperm it soothed the pain a bit, over all it was a great experience.