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Lucky Me

By: Londebaaz Chohan



The 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 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 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 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.

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Hi ISS readers, I am Sagarika from Bangalore – my age is 29 and got married at an age of 28 which is quite late for a south Indian girl. Let me just tell you my social surroundings – Married to a software engineer – Project manager to be precise, who is 5 years older than me. He was 33 when we got married. We moved to Bangalore after we got married because I husband was working here and his native was a village in the south of Tamil Nadu. We currently live in 3 bedroom apartment and I have...

Incest
3 years ago
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Eden RescueChapter 29

The two landers descended simultaneously at daybreak on the planet. Gagugakhing had said two days, but she hadn't specified a time in the second day, and MacPherson didn't want to waste an instant. But as they touched down there was nothing awaiting them except for the newlyweds. It remained thus throughout the morning, as the four humans—Igwanda, Heisinger and the two pilots—paced restlessly back and forth. Occasionally one or another of them would initiate a conversation, but it quickly...

1 year ago
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Looking for Gentry part 2

The Gentry case, oddly, remained alive. Usually, big city police don't chase too hard to find the owners of abandoned cars: impound lot fees can mount up to a nice piece of change. The Norfolk cops didn't care about Gentry's Audi. Mrs. Gentry didn't seem to much, herself. She still didn't really want to talk to me, and she had no intention whatsoever to have a word with the local Sheriff. How anyone was supposed to help was more than I could say. But in a way, I thought I understood;...

4 years ago
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2 It Is Not Cheating if You WatchChapter 7

My son didn’t answer my question right away. I felt so guilty about asking Justin to be my Master. I had practically insisted that he do it today, but that was just for a few hours with the other girls present while I worked out some kinks. Who else could have done it? “I don’t think Dad would appreciate that,” Justin answered somberly, and he looked in the rearview mirror at me. I felt as nervous as a schoolgirl who just passed a note to the front of the class to ask if a boy would check...

2 years ago
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The Education of Jasmine Ch 10

All day long as Jasmine and George did chores, her mind wandered to her bath and Jim. It really excited her to recall him outside of her window the night before. The glimpse of him reflected in the mirror masturbating while she did the same thing made her lust for him! Should she call him? She wanted to, but could she really do it? The sexual tension was building inside of her all day, and in a way she liked the way it made her feel. When George and Jasmine finished, they sat out on the deck...

2 years ago
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Aunty Ke Saath Jannat Ki Sair

Hello readers main Sameer Sharma hoon aur 22 saal ka hoon aur navi Mumbai mey rehta hoon. Peshey se mey engineer hoon aur ek vikhyat MNC mey kaam karta hoon. Mey ek achchi family se belong karta hoon. Mera kad 5 ft 9 inch hai aur rang gora hai. Mai gujrat ka rehne vala hoon. Vaise mey dikhne mey achacha hoon par meri dikkat yeh hai ki mere aage se baal thode kam hai. Iske karan mujhe ladkiyon ko approach karne mey dikkat hoti hai is liye hi shayad mey porn stories padne ka aadi hoon. Yeh kahani...

1 year ago
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BackroomCastingCouch Shaye 11232020

We have 22 year old Shaye on the couch this week. She’s a server who’s sick of serving people their food, so she’s gonna see if the adult industry is any better for her. Shaye’s thicker than a snickers, a natural slut and really goes the extra mile to prove to us she’s the one. We really had a good time with this enthusiastic girl. She jumped at the chance to suck some dick as that’s her favorite. Next, Cam put her to work nailing her on the desk and the...

xmoviesforyou
1 year ago
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PornWorld Christie Stevens CockCraving Cheating Wife Christie Stevens DPd by Fuckbuddies

Its the middle of the workweek, her husband is out of town, and Christie Stevens is craving hard dick. To satisfy her burning desire, she starts texting various men shes had affairs with in the past, asking them to come over and stick their cocks in her. In this case, it turns out that the second guy she messages is keen. Before he comes over though, Christie warms her pink pussy up with her fingers as she lies back in her office chair. When John shows up some minutes later, Christies legs are...

xmoviesforyou
1 year ago
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Seduction of Roshni

Hi I am Ravi 42 years old and engineer by profession.. I am married with two kids.. We have neighbor who are middle class family and they have daughter of 19 years who is going to college. Her name is Roshni. We have very good family relationship and we used to eat and stay at each others place especially during vacation time when one of our spouse needs to go to her parents house. Roshni is 5.6feet tall and slim and had physic of 34-28-34 and fair complexion. She used to discuss all her...

3 years ago
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Runway 9

Chapter 9 Brenda on the other hand rode the subway to and from work everyday. She didn't mind except when some pervert would pinch her ass. She was learning that being a girl could be an adventure and it wasn't always a pleasant one. She pushed her key into the entrance door and entered the hallway of her apartment building. The door slammed shut behind her. "Brenda, how was your day?" asked Annie as she heard her favorite tenant enter the building. Annie had made a habit of...

4 years ago
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The Far Plane

Once more, we thank you all for the years we’ve had, and hope this final week is the send-off The Far Plane and you players deserve. Here’s to future adventures! - Natasha Kane, Project Lead on ‘Amissa Mundo’ I stared at the headline in a paralyzing mix of nostalgia, sadness and shock. It had of course been years since I played The Far Plane, and almost as long since I’d heard news about it. But on top of the shock I felt toward this happening was the shock of who delivered this news. Abby...

Fantasy
3 years ago
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Mr Darcy and Miss Bennett

“Mr D’arcy how delightful!” Mrs Bennet simpered as her new neighbour arrived on horseback quite unannounced . “Indeed Madam the pleasure is all mine!” Mr D’arcy replied airily, “Tis a pleasant enough little place you have here, quite like my lodging at Manderly but somewhat smaller I fear.” “Oh Mr D’arcy you are too kind,” Mrs Bennet smiled through gritted teeth, “Come you must meet my girls,” she added, seeing an opportunity to marry one off, and called upon them to come through. “This is...

1 year ago
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Tivatswingers

[/image]Sea storyWe were in a long problemunaš marriage no longer looked like about anything, I found myself with more on the sea with the k**s from school and koleginicom.Deca were gone and I was left das wait for her husband and c***d, this time he takes to the sea. The first year of the divorce, resolve to be alone at sea, I found their pensions, which was bračpni and extra bed, bathroom with .. jasam crossed the colleague who had a sister married in Budva with no more appeared, but došloi...

2 years ago
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Mary A New Friend

I went to bed, dreaming about what my girlfriend had in store for me. The next morning, after we had a quick morning fuck, we got dressed and headed to campus for our only class together, Acting 101. While walking to class, anytime a girl who was even half way attractive would pass by, Mary would point and ask “How about her?” Each time, I’d just say no. After saying no to about the 50th girl, I finally said “Look Mary, I know what you’re trying to do, and I’m flattered, but I just feel weird...

1 year ago
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A night that just happened

A friend I’ll call R used to come by and he and I would watch races, football games etc, drink and bullshit. My wife who I’ll call S would sit with us, make snacks and watch also but really wasn’t into the late night games. Occasionally she’d fall asleep and R would comment on the way she’d curl up or stretch out on the couch, the way her legs looked, her breasts moving up and down as she breathed and of course I’d mention private things like her nipples, how wet she’d get during sex, how good...

4 years ago
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He Didnt Complain

This event took place in a large Jewish hospital in California. My girlfriend at the time told me about her event and it just recently occurred to me that some might appreciate her story. Older readers here can tell that this took place some decades ago because she was an LPN who wore a small nurse cap which is no longer required in hospitals.The other detail that dates the story is that my girlfriend learned later in her work at the hospital that she had passed the “elbow test” which the...

Masturbation
1 year ago
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Old Lady goes to heavan

An old lady dies and goes to heaven. She's chatting it up with St.Peter at the Pearly Gates when all of a sudden she hears the mostawful bloodcurdling screams.Don't worry about that', says St. Peter,'it's only someonehaving the holes put into her shoulder blades forwings.'The old lady looks a little uncomfortable but carries on with theconversation.Ten minutes later, there are more blood curdlingscreams.'Oh my God', says the old lady, 'now what is happening?'Not to worry', says St. Peter,...

2 years ago
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Massage Extraordinaire

She met me at her front door. The tall long-legged blonde with a well-shaped figure in the shortest mini that allowed her pink panties to peek out of her nicely rounded bum escorted me into her massage room.All this left me speechless! I could barely greet her so took a deep swallow instead. Once I’d regained composure I timidly smiled as I certainly did not want to be part of a sleazy massage parlour. However, an air of professionalism was evident: a proper massage table, a variety of oils,...

Masturbation
3 years ago
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Babysitting4

When I was fourteen, I started getting interested in my older sister, Kimmy, who was sixteen. She used to do a hula dance for me, and pull her top up and show me her tits. Kimmy was a true nymphomaniac. As I found out later, it didn't matter how young or how old the guy was, if he had a functioning penis, Kimmy was interested. And she was built too! Round, firm tits like little peaches and long slender legs that always seemed to be exposed to the crotch, no matter what she wore. One...

1 year ago
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Betting On My FamilyChapter 13 Double Dates

Nine hundred dollars... If you ever wondered how much it costs to fix a patio door with a body-sized hole in it, there’s your number, excluding tax and installation. I’d been a rich man only two days ago, but after paying for that goddamn door, and the much more reasonably-priced bump & grind from Lexi, I only had a few hundred bucks left, and I’d hoped to help Syl out with her books. I ended up giving her the rest, keeping enough to serenade Katie and the adorable Asians down the street...

3 years ago
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Haunted house chapter 1

‘So this is it,’ I thought. I stood in the moonless night, pensively staring up at the so-called haunted house. Evenafter all these years, it was still an impressive structure. Built in the late Eighteen Nineties, thefour-story house still had all the hallmarks of a great home. Detailed woodwork adorned thelarge covered entrance and marched its way across the brick façade, while large multi-panedwindows offered views of the outside. They were strategically placed and stood ready to coaxsunlight...

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