I'll never forget the first time I tried my mothers pantyhose and high heels on. I slid a pair of tan nylons on and became instantly erect She had these gorgeous two tone brown heels that i'll never forget. They were made with perforated leather. A thing of beauty really. My legs were thin supple and toned so I looked great in them. I remember having the most incredible orgasm that day. The first of many in heels. One day at school they had an auction to raise money for the the seniors grad trip. They had the boys and girls behind a chalkboard. And as I think about it now I am thinking it was maybe a little inappropriate. They had them roll up their pants or they had shorts on. Their legs were smooth so I'm assuming the boys shaved prior to this. Baby oil covered their legs and they were all wearing sexy heels . Based on that we were bidding on who we wanted to pay for as a servant for the day. I found I was more turned on by the boys with the sexy legs instead of the girls. This pretty much sealed how I would get off in my early teen years. One day while no one was home I decided to have a little femme time. I slid my mothers nylons and heels on. My mothers clothes were to big for me so I rummaged through my younger sisters drawer. I found some cute white panties a tank top and a black mini skirt. I also noticed some white frill socks. You know like the ones from the ZZ Top video Legs. As soon as I put them on I got erect. The sight of my legs made me wet with anticipation. I ran to my mother's room to look at myself in her full length mirror. I looked fabulous. I hadn't tried makeup up till this point. But I noticed some of my mothers on the nightstand so I thought why not. I slid the red lipstick over my lips. Mmm the taste drove me wild. Then I applied some mascara. The great thing about being a skinny fourteen year old Asian boy if you wanna look like a girl it doesn't take much make up. My hair was a typical mid length style of the eighties so I just restyled it with my fingers and voila not bad if I do say so myself. Standing in front of me was a beautiful flat chested Asian woman (breast forms would come into play later in my life). I noticed my panties were getting wet from the precum. I realized it had been close to 45 minutes since I put my mothers heels on. Usually I just put nylons and heels on and stroked myself to heaven. Never before did I spend this much time prepping I loved it. I slowly rubbed my cock through my panties and couldn't help but to let out a little moan. I slowly laid back in my mothers bed never taking my eyes off myself in the mirror. I slowly pulled my panties to the side to expose my throbbing hard 4 inch clit. As soon as I grabbed my clit I shuddered. I was in heaven. I began stroking. It didn't take long before I felt my clit pulsate I began stroking harder and turned to my side so I could cum all over my leg. I began shooting come all over my thigh and calf. After I pumped all the milk out of my cock I laid back exhausted dripping with come and sweat. That's when I heard him at the door. My older cousin had come over as he sometimes does to hang out and get a free meal. He heard me in my moms room and knew I was up to no good so he crept up to see what he could catch me doing. Never did he expect to find me dressed like this. It took him off guard to see me looking like a woman a woman he found attractive. Far too attractive for someone like him to get. So he started scheming. He had a camera in his car so he went back to get it. As soon as I came all over myself he got his camera ready and started taking pics of me with my legs splayed open exposing my erect cock glistening with cum. I closed them quickly but too late damage done. I looked at him and said what the hell are you doing. He looked at me and said what the hell are you doing I'm sure everyone will be surprised to know what it is you do when you're all alone. I panicked immediately was he planning on showing my friends and family those pictures. I felt like rolling up and dying. Don't worry he said I won't show anybody. I sighed with relief. Thanks I said I started getting up off the bed when he said whoa wait a minute I didn't say you could get up. I looked at him confused and a little angry. I won't tell anybody but there's things you have to do for me. Like what I said. First I wanna see you eat all that come on your leg. What I said instantly disgusted but feeling a tingling at the same time. You heard me he said. I started crying. Clearly I couldn't handle the stressful situation I was in. My cousin came up to me and put his arm around me. He said don't worry little cuz everything's gonna be fine. And with that he started tenderly caressing my nylon covered thigh with his finger. That tingling sensation came back I could feel his breath on my neck as he started lightly kissing it. He put his finger now covered with my come on my lip instinctively I opened my mouth and licked it clean. He continued feeding me until he had all of it cleaned from my leg except for the wet spots. We'll he said I better clean that for you and stared licking my thighs slowly moving down to my calf until he sucked all the come off my nylons. To my shame my clit had become rock hard. He noticed this and gently grabbed it I shuddered in shock and excitement I tried to pull away. This instantly angered him he got up grabbed my hair and slapped me so hard I teared up instantly. He gave me my one and only warning to do as he says or he would beat me senseless. I was so scared I wasn't worried about the blackmail anymore I was worried about getting beaten. He still had me by the hair and used it to pull me back onto the bed. With both of us lying down he began to stroke my hair then my shoulders. He pulled one side of my tank top down and started sucking my nipple. This felt amazing. I noticed he was moving closer to my face I knew he was coming in to kiss me but was to scared to avoid it. Our lips met. It was gentle at first his tongue slowly opening my red lips. Then he started to probe deeper in my mouth filling me. He began stroking my penis still wet and sticky he started rubbing my balls and slowly moved over my anus rubbing my wetness all around and finally I felt him pop it inside. I was so lubed up it didn't hurt in fact it felt like heaven. I started stroking my own cock now. He started with one finger then he had two in. This hurt a little but I was enjoying it now. Suddenly he flipped on my stomach. He started tonguing my ass. A sensation I greatly enjoyed especially when he went deep inside me. Finally he raised up and started to undo his pants once again fear gripped me. Before this encounter I had never had a sexual experience with anybody I was indeed a virgin. He started to spit on my ass and his cock which was a lot bigger than mine. About seven inches and thick. Next I felt him press up on my anus I was scared of angering him but also excited I began to push back on him until I felt the pop and the pain. I instantly stopped and screamed. This in no way slowed him down in fact it made him pump hard and fast. I cried out loud please stop it hurts so much. He didn't care. He just grabbed my neck twisted my face towards him and stuck his tongue deep in my mouth. All the while pounding harder and faster. After about a few minutes I started to relax and it started feeling good. I could feel a new sensation deep in my ass. I felt like I was going to cum. But how was this possible he wasn't stroking my cock neither was I. Nonetheless I could feel it building up with each thrust deep within me. Until finally I exploded cum oozing out of my cock. So much cum. My sphincter tightening with each load. Tightening around his throbbing cock. This was enough to put him over the edge as he exploded in my ass. He slowly pulled out his milk dripping out of my ass. He laid down beside me rubbing my legs for awhile then got up we both felt awkward at this point I quickly cleaned the mess on the sheets and on myself. He quickly did up his pants and quickly left. It's been twenty years since that first day and we still occasionally still meet up. I just tell my wife I'm Hanging with my cuz.