I had always been obsessed with Lucy, she had long been a family friend and for as long as I could remember I have been somewhat friend-zoned by her. We are now 19 I have seen her progress into an amazing woman, long blonde hair, slender body and amazing features. Me & Lucy have always gone on family holidays with me and my brother and Lucy and hers. Me & Lucy are the oldest of the two and enjoyed bossing around the two younger lads but they are now 16 and don't stand for it much anymore, but they please themselves.
When we aren't on family holidays I would often go round to their house and chill but my brother would never come with me as he and her brother were never as close as us two. I would often chill with Lucy but when she was busy I just hang around with Jack her brother. Jack was himself very skinny and effeminate in a way and him and his sister would often be mistake for twins.
Not so long ago I was chilling round Lucy's and she told me that she was going out to an awards evening with her parents and that she had to get changes, so would I go play Xbox with Jack. I went downstairs to jack and we booted up a game of Fifa. Jack had always looked up to me and asked if I was going to stick about for a bit and I said yeah as I had nothing to do, and Jack was 16 and there isn't much for him to do on a Friday night anyway. Time past as Lucy emerged from upstairs and my breath was taken away, she was fully made up and wearing a tight white dress with black heels, it left nothing to the imagination and I was truly mesmerised! It wasn't long before Lucy and her parents made off for the awards evening. Once they had left I joked to jack that I would love to fuck his sister, he took it on the chin and smiled. A couple minutes passed and I teased him after he scored "Damn, I can't believe I’m getting beat by someone who looks like a girl" he replied "what! I don't" I then proceeded to say "Mate, you look like your sister" his eyes widened at this comment, "Do I really?" He asked, "Yeah you do!" he giggled at this and went back to playing the game.
We were quiet while we played and after we'd finished our 5th game he said "I'm just going up to get a shower and stuff, stick around and we'll watch a movie or something in 20 minutes" I had nothing else to do so I agreed and switched over to the TV. Time passed, and after about 45 minutes I shouted up "What are you doing man, come down I’m bored" he shouted back down "hang on two minutes." I heard him come down the stairs and he stopped behind me at the bottom of the stairs, I didn't look round and he said "how about now, do I look like my sister?" I was confused and I turned around and said "Wha......" I was shocked I looked at him standing there his long smooth shiny hairless legs in a big set of heels, wearing a tight lacy black dress that I’d fantasies about his sister in numerous times. His blonde hair straightened past his shoulders and his face fully made up with red lipstick and long eyelashes.
I couldn't believe my eyes and finally managed to utter the words "what are you doing" he slowly shifted his body weight onto his other leg and said "you said I looked like a girl, so I thought I’d be one" I muttered "you look like your sister" he smiled and grabbed my hand and lead me upstairs into his room and sat me on a chair. I was still shocked as I sat in the chair and he said "how do I look" and I repeated "like your sister" and he then said "enjoy this then!" and he put the music on and approached me and started to give me a slow lap dance. He swayed with the music slowly brushing past me as he did. He let me see all around him and I was hard in my trousers and he could feel that as he started to grind against me. He dropped to his knees and pulled out my 8 inch cock and started to kiss and put his mouth over the end. He started to suck licking around the end of my cock occasionally stopping to say how he's always wanted this. I was so aroused and I couldn't believe it I loved him rosy red lips sliding on my cock and especially loved it when he glided his tongue over the end sensually licking up my precum.
I picked him up and kissed him with him straddling my cock! I picked him up and peeled off his sexy dress and threw him on his all fours on the bed. He was there in his sister’s silky lingerie which scantily covered his body. I dove down and pulled aside the thong and glided my tongue around his ass, licking across as he moaned, I could see his cock was hard and had precum dripping off the end so I in the heat of the moment, sucked it off. His asshole was wet dripping with my saliva so I put my cock in his ass and started to slowly fuck him. I was soft at first but with every pump I was getting faster. We were both moaning with pleasure as I was sliding in and out of his body.
I flipped him on his back and started maintained my now quick pace as he was playing with his nipples under his sister’s bra. He then panted "play with my clit" so as I was fucking him I was stroking his cock and he was writing in pleasure as his cum wet panties cradled his balls as I fucked him. He sprayed his cum over his chest and bra and I continued to fuck him fast. He wiped up his cum as I fucked him and licked it off his fingers and this sent me over the edge. He sensed this is in ass and jumped off and sucked my cock and I blew a massive load into his mouth and we both collapsed on the bed.
Lying there I caressed his smooth all over body and said "you look just like your sister" as we kissed passionately. He said "I’ve wanted to be you're naughty girl for a long time now" and I replied "well you're it now!” we lay there for what seemed a while kissing and caressing his body. He then said "It's only 9 and my parents aren't due back until 1, are you staying a while" I smiled and replied "of course"
I hope you enjoyed this true story, more to come in several parts.