Date: Wed, 13 Aug 2008 09:49:31 GMT From: Check It Out Subject: Letting My Hair Down-1 I'm Jimmy James. This story is about my friend asking me to let my hair down while I suck his cock. He tells me it's because I look like my sister.. So, I surprise him by answering the door dressed as my sister. (cd, m/m, oral, anal) ============================ I had started sucking my friend Bob's cock just after we got out of the sixth grade. We both considered ourselves straight. It had started innocently enough. I had boosted him up so he could look through my sister Roseanne's window while she got dressed. He was really hot for her and when I told him that she looked as good as the Playboy girls, he had to see for himself. We were 11 and she was 15 at the time. For him she was his dream girl. She had bright green eyes with long curly red hair that hung down nearly to her nipples. Big pert firm breasts with pointy nipples. A small patch of wispy red pubic hair that left her pussy fully exposed and a nice round ass that jiggled when she walked. Every boy in the neighborhood was hot for her and Bob was no exception. Anyway.... I had boosted him up to her window to peep at her and his crotch was right in my face. He had on loose shorts and no underwear. His fly was open and I was staring right at his cock. As he watched, his cock got hard and poked out his fly until it was nearly touching my nose. I stared at it mesmerized. I watched his cock get hard only inches from my face. It looked so hot sitting that close that I began sucking it while he watched Roseanne. He was so taken with seeing her naked, that he didn't even seem to notice that I had sucked his cock. We spent the whole afternoon together and all he talked about was seeing Roseanne naked. I sucked his cock twice that day and he didn't say anything until the next day. We showed our friend Billy what we were doing, and when he found out Bob had seen Roseanne naked. He totally ignored the fact that he had just watched me suck Bob's cock. I got kind of mad because my sister got all the attention, so I sucked both their dicks again while they talked about her. They didn't even seem to notice. I've been sucking Bob's cock as often as possible for about three years now. We both look forward to it too. To us it's a given that if we're alone, I'm going to suck his cock. Being 14, my parents don't mind leaving me and Bob alone. Nothing gets messed up, nothing gets broken. There's never a crowd of kids over. They say they think we're two of the best kids around. I wonder what they would think if they knew that the reason everything goes so well is because I spend most of the time sucking Bob's cock. We almost never get off the couch. Today, Mom and Dad were getting ready for work, I had just gotten out of bed and Bob had come over early. We all sat at the table and talked until they had to go. As soon as they were out of the driveway, Bob had his cock out. I shook my head and told him he would have to wait until I was out of the shower. I was in a rebellious stage and had been growing my hair long but was shaving everything else. I kept my legs, pubes, underarms, everything shaved and I kept my hair in a braid almost always. When I got out of the shower, I brushed my hair, put on a towel and walked out the door. Bob was still sitting at the table with his pants down. When I walked out, his eyes lit up. I watched him get rock hard as I walked across the room. It was standing tall and throbbing by the time I got there. I smiled, got on my knees and started to lick and kiss the fat purple head. Then I gently sucked the head into my mouth, rolling my tongue around it as I sucked more and more of his cock into my mouth. I love the way his cock feels in my mouth. He had the perfect cock. It was a little over 7" long and not so fat that I couldn't deep throat it, but fat enough that it was worth the trouble. I felt the shaft slide through my lips until the head of it squished against my tonsils. I opened my mouth, pushed hard and I felt his cock slide smoothly down my throat. When I felt his balls against my chin, I looked up. Bob, was staring at me wide eyed, like it was the first time we had ever done this. I looked back down and kept sucking his cock. His cock was throbbing hard the whole time. So when he grunted, it was like cum just started to pour out with no warning. It was wild, I started swallowing as fast as I could. When he was done feeding me breakfast, I sat at the table and started to braid my hair. "No! leave it down!" Bob said quickly. "Sure" I said shrugging. We talked for a while, until I saw that his cock was hard again. I giggled, "Again?" and got to my knees. Bob stood up "I gotta fuck you!" he insisted. I lubricated my ass and bent over the table. We had been doing this for about a year now and I liked it every bit as much as sucking it. Getting fucked was very raw and carnal. Not nearly as personal as sucking him. Bob got behind me and pulled up my towel like a skirt. He started to caress my smooth ass. Gently running his finger tips around every curve. He had never done that before, usually he just sticks it in and goes to town. It didn't matter to me, it was really turning me on. All I could do was moan at the pleasure coursing up from my ass. I couldn't wait for him to fuck me. Bob stood behind me trembling as he eased his rock hard cock into me. Once I was completely impaled, he pulled it out and eased it back in slowly several times. Then he started to hammer it into me as hard and fast as he possibly could. He was wild eyed and groaning while he fucked me. I could feel his hard shaft sliding through my tight asshole until his belly slapped against my ass, then pulling out leaving me empty inside. He stabbed it in and began jumping around. I could feel him throbbing inside me and knew he was filling me up with cum. When he was done he pulled out, slapped my ass hard "Fuck That Was Good Rose.... uh Jim!" I looked at him funny "Why so horny today?" "Fuck, Jim you'll be mad if I tell you." he said shaking his head. "What?" I asked sternly. "With your hair down, you look just like your sister." he confessed. I rolled my eyes "Whatever!" Bob apologized, I got dressed and we went out to play some hoops. I still hadn't put my hair up and Bob was missing some easy plays. Bob's mom called and said he had to go home and wouldn't be back for a couple of hours. He talked to her and she said he could come back after lunch. "Well, I guess I'll see you at one." he said as he headed out. "Cool" I responded and headed inside. I went to the bathroom to braid my hair. When I looked in the mirror, I had to admit, I really did look like Roseanne. I had the same bright green eyes. The same long curly red hair. I pulled my hair back into several of the styles I had seen her in. I nodded, I could see where Bob was coming from. I did look alot like her. I thought for a second, Why not dress like her too? If Bob wants to fuck her so bad, why not let him? I could get dressed up for when he comes back and he can fuck her. I was already sucking his dick and letting him fuck me anyway. Why not do it dressed like Roseanne? I stripped down and went into Roseanne's room. I began picking through her boxes of old clothes and the first thing I found was a pink thong with ruffles around the legs. I found a white cotton tank top and a short black miniskirt. I found some high heeled black boots. After some digging I found a pink bra to match the panties. I smiled and got dressed in her room. I hid my cock between my legs and pulled up the panties. They were pretty tight so they held my cock in place nicely. She had outgrown this stuff years ago and they were pretty well broken in. The panties and bra were so well broken in that they felt like they were about to fall apart. The top and skirt felt like part of my skin and the boots were so comfortable it was like wearing sneakers. It felt fantastic! I checked myself out in the mirror. I walked around, bent over checked out my ass, pulled up my skirt to see the panties. With my cock tucked back it kind of looked like a pussy. You could pretty much see through the panties, so it was hard to hide anything. I really did look like her and I was pretty hot. I was going to take it off and forget about it if I didn't like it, but it looked and felt so natural that I sat at her makeup table. I plucked my eyebrows, put on base, lipstick, blush, eyeliner, mascara, everything! When I was finished I was really happy, I could've been Roseanne's clone. I grabbed a ribbon and put my hair up like hers. I walked around the house for an hour checking myself out and anxiously awaiting Bobs arrival. As I walked around, I couldn't help but to notice how good everything felt. I mean It really felt good. These must have been the worlds softest panties. They gently caressed my smooth skin like a lover. The breeze blowing up my skirt, felt so sexy I could hardly stand it. I was using two water balloons to stuff the bra and they were jiggling like crazy. It was the most awesome feeling ever. It almost felt like they were my real tits, jiggling around. The skirt and top were so soft that they wrapped around me like they were part of me. The boots were the best part tho. They were so comfortable that walking in really high heels was the easiest thing in the world. They were the greatest. While I was standing, I could feel my ass pushing out. When I was walking, I could feel it swaying back and forth. They gave me an instant appreciation for the way women walk. It was a total turn on to dress like a girl. I had never thought of it before today, but I never thought of sucking cock until it was in my face. This was the same thing, now that it was in my face and I had done it, I loved it. My tits were jiggling like crazy and I could feel my cock getting hard between my thighs. I reached under my skirt and into my panties as I went to sit on the couch to jerk off. I pulled my half hard cock out and sat down. When I looked down, I had my cock in my hand and was treated to the strangest sight I had ever seen. I was looking over the top of a rather large set of tits, my cock was sticking out under my skirt, my panties were pulled about half way down my smooth thighs and I had on high heels. I was looking at a girl with a cock. That's when it really sunk in. It was such a turn on, that no sooner did I start to stroke my cock than I blew my load. I licked up the cum, put my cock back and sat and admired myself some more. I spread my legs and admired the way everything looked and felt. I got up and walked around some more. I practiced swaying my hips when I walked. I watched myself in the mirror. I pulled up the back of my skirt again and smiled at my bubble butt. Heels were the greatest. I heard the doorbell, so I quickly rearranged my skirt and went to answer it. When I opened the door, Bob was stunned. "Hi, Roseanne" he said sheepishly. I smiled "Come on in" and walked to the kitchen. I knew Bob was staring at my ass as he followed. He had told me he always watched Roseanne's ass. So I paid extra attention to the way my ass swayed while I walked. When we got to the kitchen, I told Bob to have a seat. I went to the refrigerator and opened the door. I bent over to get two sodas, giving Bob the perfect view of my ass. I spent extra time picking around while bent over. That way he had plenty of time to study the way the cheeks of my ass swayed back and forth. The way the thong looked pulled between them. The way the ruffles framed out my 'pussy' between my ass and thighs. I had been keeping my back to him for the most part and he still hadn't had a good look at me. I turned toward him, jiggled my tits a bit and gave him his soda. "Jim says you want to Fuck me!" I said angrily. Bob just about panicked. He looked like he was about to jump out of his skin. "Uh, uh, uh." was all he could say. I giggled, pulled up the front of my skirt and jiggled around some more. Then in my most seductive voice. I said "Fuck Me Bob!" Bob shook his head in disbelief and I busted out laughing. Bob didn't know what to do at first. Then he realized I wasn't Roseanne and started laughing too. "Fuck Jim you really had me going! Holy Shit I thought you were Roseanne!" he said excitedly "What the fuck are you doing in her clothes?" I laughed, sat at the table and opened my soda. "Well, you were so turned on by fucking me when you said I looked like her. I decided to give you a treat and dress like her too." I told him. "Very Cool, You really do look like her you know?" he said smiling. "Yep" I said smiling back and spreading my legs. Bob stared at my 'pussy' and couldn't look away. I could see, he was just about drooling over it and closed my legs again with a giggle. Bob looked up at me with a big grin. "That's fucking awesome!" he said nodding at me. I stood up again "You ain't seen nothin' yet." I shook my tits at him and straddled his legs. I began rubbing my 'pussy' against his hardening cock. Bob pulled up my skirt and began to play with my ass while he watched my big jiggling tits. I reached between us and undid his pants. We began to kiss as he caressed my ass and thighs. I was breathing hard and my cock was also pretty hard.. Making out with him as a girl was such a turn on I wanted him bad. We kissed and caressed each other as I eased his pants down to his knees. I straddled his lap again and could feel his hard cock pressed against my 'pussy'. I was so turned on and it felt so good, I was about to scream. Bob gave me a big hug, stood up and laid me on the table. He kissed me some more while he fumbled with my panties and lubricated his cock. He was bent over kissing me while he eased his cock into me. I took in a quick breath and sighed. I wrapped my arms and legs around him and pushed hard against his invading cock. He eased it in and out slowly several times. Then he grabbed behind my knees and pinned them to the table on either side of me. I was pinned down and could hardly move. He began driving his cock into me hard and fast. It was such a turn on to be dressed like Rosanne and get fucked, I began to squeal and jump involuntarily. Then I had a huge orgasm. I bucked and screamed "F.U.C.K!" When I came to my senses, Bob was still pounding his cock into me mercilessly. I could feel my tits bouncing every time he drove into me. Bob couldn't take his eyes off them they were bouncing around so much. Bob drove into me and began to groan and shake. I squeezed my ass tight around his throbbing cock. We stayed frozen like that for several minutes while Bob emptied his balls. Then he loosened his grip and began to slowly pump his half hard cock into my now cum soaked ass. Bob was looking at me with a big satisfied smile. "Man, that was so fucking awesome!" "No Shit Hey!" I said smiling back at him. "This is such a turn on to do this dressed as Roseanne." "Man, I'm telling you, it was like I was really fucking your sister! It was fucking awesome!" he said while he continued to slowly pump his cock into me. I beamed with pride "I tell you what... I'll stay dressed like her for the rest of the day and any time you want sex, just whip it out and tell me what you want. It'll be just like having Rosanne as your personal sex slave." "Hell Yes!" he nodded "Hold still then, because I'm going to fuck you again." He began to drive his cock into me hard and fast again. He called me Roseanne and told me what a slut I was. He told me how he was going to make me suck his cock all day and if I was lucky he might fuck me again. I laid on the table and squealed my delight. He fucked me hard, for a good long time before cumming again. We cleaned up and got dressed again, then sat at the table. We talked for a while and Bob ogled me non stop. It turned me on and I took it as a compliment, so I gave him all kinds of sneak peeks at my panties and ass. Bob suggested we shoot some hoops, so we went into the back yard. We shot a few games of horse, which Bob lost. I cheated though. I would pull up my top, or my skirt or bend over while he was shooting. He then decided that we were going to play one on one, and he was the ref.. I said that would be fine and we began to play. While guarding me, he would grab my ass or tits. When I called foul, he said he was the ref and there was no foul. When I grabbed his ass, he called foul and made me suck his cock on the free throw line. When I made a basket, he called foul and made me take off my skirt. I had to laugh, I was playing basket ball in the back yard in high heels, a thong and skin tight tank top. My tits and ass were flopping in the breeze every time I moved, I must have been quite a sight. Plus, Bob was coming up with the most outrageous fouls and penalties. The fouls were things like, My tits were bouncing too much. My thong distracted him. My ass was making his dick hard. My 'pussy' was too hot. The penalties were things like, Do a handstand from the basket to the free throw line. Spread my legs and tell him how much I wanted his cock. Touch my toes. And of course, suck his cock. We had the best day that we had, had in a long time. We had so much fun, playing hoops in the back yard. Me dressed as Roseanne and him calling fouls. It was exhilarating to do it in the back yard too. It was a rush knowing that anybody who got a peek over the fence would have seen it. Not only that, it was exciting to think that if they did see us, they would have thought my sister and my friend were getting it on in the back yard.