Dress Up With Randy

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Dress Up With RandyUnlike most boys growing up together my older bruther Randy and me played more differently than most siblinngs do. Sometimes he liked to make me play dress up and he usually wanted me to dress up as a girl. Randy typically would grab our sissters old dresses from their closets and bring them to me so I could try them on. My siss wore these dresses when she was elevin or twellve. I was in my early teeins at the time and I guess he figured they would fit. Truth was I didn’t have the curves, but then again neither does a girl my age, so they really were just my size. One day we were hanging out in my sissters old room as we usually did whenever Randy wanted to play dress up with me. Randy was picking out a dress for me to wear while I undressed in plain sight, complaining to him like I almost always did saying, “Maaan… Why do I always have to wear a stupid dress when we play this game?…” Without turning his head, he continued to dig through our sissters old closet in search for a nice dress for me to try on, and soon he replied, “I told you already, you don’t want your friends to find out that you still wet your bed at the age of thirrtein right?… I thought you didn’t… That’s why your wearing a dress again for me…” I brought down my underwear to my feet, kicking them to the side bowing my head out of shame and I stood naked in the middle of the room waiting for him to pick the dress already. Randy handed me a pair of light pink panties along with the dress he picked for me to put on and at least he had the decency to leave the room while I put them on. He stared at my fully exposed nude body for a little while before leaving the room and shutting the door behind him. Once I finished putting on the dress, I sort of flaunted myself in the mirror admiring the way my long light caramel brown hair reached just barely passed my shoulder straps on the dress. Suddenly I jumped, hearing the door swing open only to see Randy come in and close the door behind him. I swear, if anyone other than Randy would have walked in at that moment, they would’ve easily believed I was a pretein girl in a pretty dress. Randy handed me my sissters old dolls which bolu escort he snagged from a chest in our attic and told me to play with them on our sissters old bed. I did as I was told heading for the bed to play with those girly looking dolls and Randy just stood there watching me the whole time. Naturally, I wasn’t used to wearing a dress and I sat on my bed with my legs carelessly spread wide open. I had on a pair of light pink cartoon printed girly panties which also used to belong to my siss and he made me wear underneath the dress in place of my underwear. Those panties I was wearing at the time were now in plain sight for Randy to see. He stared straight at the area between my spread legs where he stared at the small yet noticeable bulge of my dick and balls. I looked up for a second only to see my older bruther staring at me and he was giving me that look he usually gave me before asking for a certain request. Randy grew a devilish smirk on his gritty face and he said, “Hey Danny… I wanna play mommiy and daady again… Come on, just like last time… You’re the mommiy and I’m the daaddy…” Randy climbed on the bed and he spread my legs wide lifting up the front of the pretty white dress folding it up over my chest as I felt him tugging down on those pink panties like he usually did to my underwear when he wanted to touch my dick and stuff. Somehow I knew he wanted to try that thing again with my butt and for some reason I didn’t complain this time, remaining calm. I bit my bottom lip as he raised my legs up using both his hands and he crawled forward getting closer to my exposed lower end. Randy grabbed the package with both hands, tearing it open with his teeth and he pulled it out, carefully slipping it on over his fully erect cock. He focused all of his attention down there at that moment as he aimed his condom covered blunt cock head towards my tightly puckered pink bum hole. The dress was a bit fluffy and it covered most of the action so I couldn’t see exactly what was going, but I could feel it. Randy pushed the tip of his hard cock into the extra small opening of my anus and I felt the pressure being applied directly in the center of bolu escort bayan my anus while his cock pried into it. I moaned softly with a slight complaining whine, as if I was having a tooth extracted or something, “Mmm… Ahh… Mmmm!… Oohhh…” I gasped for air when suddenly I felt it slip inside of me, stretching my bum hole in ways I only felt when he was doing this with me. Randy tried to keep me calm while he continued to thrust forward and I felt his cock slide deeper into my bum as he started saying, “There we go… Ohhh yeah… That’s it. Here we go… Uhhh!… Atta boy Danny… You’re doing really great…” We stared at each other’s faces for a brief moment in time and I looked into his eyes as he bottomed out, feeling him completely inside me then. That seemingly magical moment faded quickly when his focus was taken once again down below. Randy pulled out his cock just far enough so that only the very tip was still buried in my bum hole and then without wasting another second he thrusted forward with a little more speed this time. I prepared for another rather harsh fucking from my older bruther who was nearly twice my size at age siixtein and my hands clamped down firmly upon the frilly pink bed sheets as he bottomed out a second time. Randy moaned louder as he said, “Uhhh!… Atta boy Danny. You’re being a reeally good mommiy… Ohhh!… Uhhh!…”Randy pulled out his cock just as much as before and he pushed it back all the way in. He began thrusting steadily into my bum without pausing as I moaned feeling his cock diving into me again and again. “Uhh… Uhhhh… Oohhh!… Uhhh!… Uhhh!…” Since I couldn’t always see what was going on down below, I tried to study his facial expressions each time so I would know when he was close to finishing and I knew it usually took another minute or so before he was done. He was moaning off and on, loudly with little regard about making noises that were loud enough for momm to hear from down the hallway. I held my firm grip on the bedsheets as the whole bed started to shake with every pounding thrust Randy gave into me. It felt like half an hour or so had gone by but really it was about five minutes escort bolu after my older bruther started thrusting in hard upon my bare ass. The only noise I heard the most was that of his hips slapping against the soft tender flesh of my blushing bum cheeks, which felt rather sore afterwards. Randy moaned louder as he continued fucking me mercilessly, “Ohhh fuck!… Uhhh!… Uuhhh!… Ohh yeah!… I think I’m just gonna cum inside you, I got a condom on anyway… Ohhh!…” I waited patiently for the inevitable ending of the long lasting fucking I was taking then and I held on tight to the bedsheets as the bed kept rocking to the rhythm of his hips pounding upon my bum’s tender flesh. Randy moaned loudly as he said in hurried words, “I’m cumming… Ohh shit!… Uuuhhh!!! Uuhhhh!!! Uuhhhh! Uuhhhh! Oohhhh!… Uuhhh!… Uhhh!… Ohhh yeeaahhh…” I relaxed myself better now knowing that it was finally over and I let go of the bedsheets while Randy kept his erupting cock buried inside of me as he promised. I let out a sigh and so did he as he started pulling his cock out from being lodged all the way inside my bum hole. “Ohh… Oohhh!… Ohh… Ohhh shit!… The condom!…” I looked down at the wet piece of rubber that had broken halfway through my harsh fucking and I said, “Umm, is that bad?… I mean I can’t get pregnant right?…” Randy nearly broke out laughing and he said, “No man!… I was just thinking, what a piece of junk that condom was bruh. Don’t worry your not getting pregnant, wearing a condom for butt fucking just keeps my dick cleaner and helps me last longer is all. I sighed from relief as he backed away, hopping off the bed and just like that he started putting his clothes back on. I lay on the bed for a while longer feeling a bit sore after what we just did together and I reached down feeling the area between my bum cheeks which was now slick with his creamy white cum. Once Randy was dressed he left me alone so I could change back to my boy clothes and I was still laying on the bed with my fluffy dress still folded up to my chest. I folded down the dress as I sat up on the bed before I hopped off of it and stood up on my feet again. For a reason I couldn’t explain at the time my dick got a bit stiff when I thought back to what just occurred on the bed only minutes ago. despite how much I wanted the harsh fucking to end, it seemed my body wanted it to continue instead…

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