When me and my buddy Nate had a sleepover at his house with 2 older brothers, most my friends were way older than me. We used to watch porn together and jerk off so we were going to stay at his house because his mom and dad were out of town and his older sister Jenny was the only one there who I had the biggest crush on so we planed on watching porn most the night in his room. When we got there Jenny seen me she know I liked her because I told her all the time I seen her how cute she was and I really liked her she was 19 she just loved how I would follow her around like a puppy sometimes she would kiss my cheek just to watch me turn red. She loved picking on me cause I did what ever she asked she aways made me wear her makeup when I’d spend the night. She told me and Nate she was going out with her friend while she put makeup on us after she was done she went to get ready when I was walking by she heard me and Nate walking by she asked if 1 of us could grab her bra from the bathroom when I knocked on her door she told me to come in so and shut her door so I did she she walked out of her closet with no shirt on her tits were just hanging out I turned really red she thanked me then kicked me out I told Nate I seen his sisters tits he told me he seen her naked after she got out of the shower before. 5Mins later she told us she was leaving so lock the door behind her and to let her in when she gets back. So after she left we went to Nate’s room it was like 5pm he said he would be right back just a few mins later he came back with one of her bras and panties just joking I dared him to try them on so he got naked and put them on he said how do I look I said like a guy in girls underwear he told me to follow him so I did he started putting her lipstick on and her blond wig and dress I said what are you doing he said I’m Jenny now I was a little confused what was going on he told me he does this every time when no one home he said his sister’s bra and panties were bigger then his moms. He kinda did look like his sister he than asked if I wanted to try some thing new then just jerking off I was a little scared but I agreed any way because he was my best friend. He asked me to kiss him so I did then he asked if I liked it I said yes softly we kissed some more now we’re both getting more turned on he asked me if id treat him as if he was a girl. I pushed him on his sisters bed he told me no blowjobs tho I said ok what should I use as lube he pulled his sisters from under her bed next to her dildos he told me he aways wanted to try this. I got up and took of all my cloth and got back on Jenny’s bed with Nate he opened the sex lube and started rubbing my cock he then pulled the dress up to his chest and but his ass in the air and his face in her bed so I grabbed my cock and slowly push it in he made some noise of pain I ask if I should stop he said no just keep going. So I did now I was cock deep in him I started off slow then found my flow all I heard was moaning after ever push after 6 mins I had him get on his back so we could kiss and get the dress off it was getting my way but to keep the thong and bra on when he got back on the bed I put my cock back in while kissing I was ever rubbing his nipples 5mins later felt like I came but there was no cum. So we were laying there he asked if I wanted to try what it felt like to be a girl I said ok but I don’t wanna wear the bar or panties he said ok. He pined me to the bed I was at his control he was twice my size. He started slow and hard I was moaning really loud he told me to not so loud the window is open I grabbed him and started making out with him to stop moaning so loud 15 mins later he pulled his cock out and shoot his cum on his sisters bed we lid there 4 almost 20mins. We look at each other and he asked what I liked best I smiled all of it he said me too we started putting her stuff away the way we found it went down to the living room and watched tv a couple hours later. Jenny walked throw the door drunk it was 9:30 she told us to start getting ready 4 bed so we did as soon as we got to Nate’s room and shut the door we started kissing and striping we fucked each other then went to bed cuddling naked.
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