Lucky Me

Lucky MeLucky MeBy: Londebaaz ChohanThe place even looked horrible. Everything, every step was so stressed and regimented but I could not blame anybody. Actually, it was nobody’s fault. My parents thought that if I was sent to this boarding school, it was better for me to teach me discipline. My name is Henry Hutch. When my parents found out about my certain habits and not acting as a very manly person and liked to be dressed in a girl’s clothes was just the start but once they found me dressed like a girl day after day; they were angry and ashamed and the last straw was, not the sluttiest dress what I wore; it was that they saw me in this dress, on my back and a friend of mine, Richard Sharp was on top of me fucking the shit out of me, fucking me hard and rough. This was a big shock for my mom and dad and off I went on my way to boarding school. The residential cabins in this fucked up school were set up for two students in each cabin to assure manhood and confidence in each. My roommate’s name was Alan. As early as about 3 months; I found out that Alan was the best and the perfect roommate for me. It was a long weekend and I had decided to visit home but the inquiry counter at the bus station gave me the wrong information and as I reported on the bus terminal, my bus was gone and I had to return back to the school. As I entered the cabin, I was stunned to see Alan wearing a little school girl’s outfit. A real short skirt, white hoses covering his thighs as well, a silky tiny black thong, black high heels, black belt and a molded foam breast cups, white bra and a wig of shoulder length black hair. He was looking damn sexy. I thought, if I also looked this sexy and hot when I was dressed up. His dressing up had beautifully camouflaged his big ass in this outfit. There was no doubt that he loved getting banged as much as I did. Looking at him was giving me a big hard on and I planned to have some fun. I could tell he was shocked to see me there as much as I was to see him dressed like a puss and then he quickly began to cover himself up. I shouted, “Alan” as I stood almost blocking the bedroom door, where he was planning to run and hide. He squeaked a quiet “Oh”, and his hands tried to hide his face. “Well Alan, you are so pretty”. I said loudly. “I have heard of guys like you. Average Joe by the day and a true butt slut by the night”. I had started to push him around. “No. It is not true. Please do not tell anybody”. Alan had started pleading. He was not only looking very pretty but sexy too and I surely wanted to fuck him so bad, as canlı bahis şirketleri he begged me not to tell anybody. My cock was getting harder and throbbing already. Now I knew why my friend Richard always begged me to dress up and how much he wanted to fuck me, whenever he came to see me.I started to toy with Alan; “What do you want me not to tell them, you are not a butt slut but occasionally, you do change into a girl and go out; looking for a cock to fuck you”.“No, No. Not at all”. He was stuttering.“Ok, then what girl’s school were you going to, dressed so nice”. I raised my voice as I reached to grab his skirt. He had no answer. “Maybe you were only going to do some floor cleaning, and just put on this dress to save your clothes”. I taunted him even worst and he stood there with his face contorting in pain.I reached up and slammed his face on the cushion over the sofa arm, grabbing his firm hips and stood between his wide spread legs as he struggled with me to get free and get up. Mother fucker, looked so sexy. His arms were waving like crazy, his skirt was pulled up, his ass was all open, defenseless vulnerable with no protection but just the thong, that was looped through his ass crack. God! He truly looked so sexy, my cock was going to beak, it was so hard. I just could not resist and pulled out my big hard thick cock and began stabbing his ass while he resisted to save himself. “No, Henry. Please God don’t”. He yelped as if he was already impaled on my fucking machine.“Fuck you, mother fucker. If you present yourself as a whore, you better be ready to be fucked like a whore”. I raised my voice still some more and pulled his panties down to his ankles. I could see his large sized cock was already stiff and damp too. I knew, he wanted it as much as I did but he kept fighting as I placed my cock knob on the middle of the balloon knot of his hole to breach his security system and enter into him and he suddenly relaxed. I was a bit startled to feel his ass being so warm and already lubed and welcoming. Now with my both hands at his hips, I was holding him still to take my hard thrashing strokes to fuck him real rough and brutal. “Yeah, take it like a man, bastard butt slut, mother fucking cock whore” I said; slapping his butt cheek hard.Now he was not resisting and just laid there, moaning and enjoying my cock entering, re-entering and entering his rectum again and again as I fucked him harder and harder with a rhythm of strokes. I was enjoying it especially more, knowing that Alan was as big a butt slut as I was. Rick’s canlı kaçak iddaa image was coming in my eyes, watching me in this position every so often. I was truly his cock whore for he had fucked me so much and so many times. I used to suck his cock just for fun and carried some girly clothing’s with me; if he wanted to knock off a quickie with me. Then he was an ass fucking aficionado, fucking me in various positions and different locations we could find over a million times. Suddenly Alan began throwing, pushing his ass back to meet my cock thrusting in him and it broke my thoughts about Richard and I started fucking Alan with full might and force to make him moan and quiver. I saw his neck turn over his shoulder to give me a huge smile and I exactly knew what this smile was all about. I still wanted to toy with him and said, “What is it, you cock whoring, butt slut. What is it, had enough already, cannot take anymore. You shitty bastard”. I was enjoying foul mouthing him when suddenly his asshole flexed tight around my fat cock. “Oh, you want me to fuck you harder and brutal, you true butt slut”. I said and decided to fuck him with utter force and power until my orgasm would kick in and I shall explode inside him. Alan was squealing, his body was jerking, his hips were bucking wildly and his asshole was squeezing my cock spasm after spasm as if he was climaxing and I was slapping his ass buns to make them look like rose red. “Yeah, Ride this ass! Yeah, that’s my girl, fucking girl that is!!! I was still toying with him as he continued to thrash around but I did not let up. I was fucking him more than he deserved. The feeling was so amazing and I was being aware that why Richard liked to fuck me so much. Just as Alan relaxed; I felt my balls tingle and my orgasm cascading fast. I shoved as deep as I could and emptied my balls inside him. I groaned and heaved to catch my breath.Once, I came to my senses; I pulled my cock out of his ass, wiped it and put it back in my pants. Still feeling naughty, I teased him saying that he was a great fuck. I told him to dress up, if he wanted. I chuckled as I looked and found his cum load spread all over the sofa back and my balls juice drooling out of his white ass. I watched him as he adjusted his cock, pulled his panties and went to the washroom. As I saw him walk, his ass looked such a marvel, I wished; I had my ass like that. As he returned, I gestured him to sit next to me and held his tit in my fingers. He kind of resented and I ran over him; grabbing both of his tits and tweaking canlı kaçak bahis them between my fingers. I even lifted his skirt to peek at his panties again to humiliate him more.“You are a hot piece of ass, Alan; or should I call you Elaine. I giggled out loud and watched him blush. He once again spoke very softly begging me to call him whatever pleased me but kindly do not tell anybody. “Ok, Elaine; tell you what”. I said very calmly. “I promise you, not to tell of this to anybody ever but only if you promise me to do something for me in return. I was very serious, when I said this to Alan. I watched him as he gathered all his courage to look in my eyes and a faint smile on his face as if giving me a fully consensual yes to do, whatever I asked him to do for me. “Next time, we do this I want to be your butt slut”. I said it abruptly and with a big smile. Alan was in a total shock and I watched his expressions change from of a mere hope to the disbelief and skepticism. His mouth was open and his jaw had hit the floor in a jiffy. He was looking at me in total mistrust and mystified.“Do you believe; you are saying this”. He asked me and I told him that he heard me loud and clear making us both scream with joy and we hugged each other. After that we told each other all our secrets, everything. Then I got up and went to dress up in a shrewd dress and we sat all night drinking and talking about likes and dislikes of ours, the clothes we had and the things we had done so far. Not surprising that our stories were almost identical; like the very strict parents to start with and a very dominant dad and a super sub mom. Instead of toys, we were into fucking girls but to us it was much more fun to be fucked like girls as well. How they say it, we were the jacks of the same trades. It was awesome to be together for the next 3 years almost as the best of the best lovers and the girlfriends. We mostly tossed a coin to decide what to and how to and the winner would dress up for the other to be used as he liked it to be for the whole night of fucking fun. Slowly but surely we got the few other boys as well to be involved and join us guys to fuck us both together. We talked of arranging sex parties, gangbangs and orgies and even run a brothel from our cabin for the traveling executives and high class salesmen needing a fuck. Just getting paid for taking some strangers cock in the mouth or the ass and beg him for the load was a huge turn on. I just did not forget my first fucker, Rich; and he did manage to visit couple of times. It was an unbelievable joy when he fucked us both at the same time, dressed like whores. Richard was awesome, to say the least and Alan was the Perfect roommate, I could get in this great school system.The End. Your comments are appreciated. Londebaaz Chohan September 5, 2019.