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My Brothers Troublesome friends…
Note: everyone is of a legal age, and names have been changed for the sake of this story Enjoy
My first time was more than a little bit terrifying, but enriching to my life beyond my wildest dreams.
It began on a family holiday, just after my older brothers 21st birthday, him being 2 years older than I was at 19. Because of this, we took two of his best friends with him. We were staying in a small house just a few blocks from the beach and the moment we got there, my sister – the eldest child of the three – got into her pretty red bikini, and set off to meet some of her pretty friends who were already there. The rest of us set to work unpacking, and moving into our rooms.
I found out i would be sharing a bed with my brothers friend Jason, after my brother and Samir had sprinted inside and claimed the bunk beds. I didn’t mind, but he seemed to. Constantly groaning on about sharing a bed with his friends faggot brother. His harsh words would influence my young virgin mind more than i cared to admit.
That evening, we watched some crappy Adam Sandler movie while my parents were around, but then once them and my elder sister retired to bed, we stopped the movie and voted on something else. I wanted to watch Lord of the Rings, while my brother and his friends all chose ‘Spring Breakers’. Nonetheless, i resigned, content enough to watch Selena Gomez and Vanessa Hudgens run around in bikinis for 90 minutes or so.
As the film came to a head, with parties, drugs and bikini babes all over the screen, my brother retired to the room with a ‘headache’ leaving Samir, Jason and I alone in the living room. Shortly after the film ended (poorly i might add) Samir wandered outside for some cool evening air, then came running inside and whispered something in Jasons ear.
Jason smiled and they walked outside together. Curious as to what was going on, i followed. There they stood, holding my sisters red tie side bikini bottoms – that had been left outside to dry – as if holding the holy grail.
It was no secret that they thought my sister was really hot, and ill admit, she looked great in her bikini, dressing and acting with all the confidence a very fit 23 year old woman should. She knew full well that she elicited stares and glances from men and women, young and old as we walked to and from the beach.
I saw the pronounced bulges in their sweatpants, knowing they had such dirty thoughts about my sister turned me on a little, but seeing the outlines of their cocks turned me on more. As they walked inside holding the delicate bikini, they were whispering more and more to each other and looking back at me as i followed them inside.
“God i wish some sexy slut were here to put this on and show us a good time” Samir said to no-one in particular.
I really hoped that they didn’t know that i have on occasion Amsterdam Shemale stolen my sister’s panties and bras to wear, but his implication was pretty clear as he turned to me.
“I can see the little boner in your shorts fagboy, how about you go tie up that long hair in a ponytail and put it on and show us? I bet that bikini will look great on your little twink ass.”
Despite my brain screaming at me that this was perverted and weird, or what my sister would think if she found out, I just nodded submissively and walked into the bathroom to put it on. As i stripped down, i realised that with my hair up in a high ponytail, my thin, hairless swimmer body and perky little swimmer butt would look exactly like a young girls body, save for the slight bulge in the front of the bottoms.
The red bikini fit my slight frame like a glove and i felt so incredibly sexy in it. As i strutted out to the boys in the living room, their Jaws dropped a little, but the bulges in their pants remained large.
Jason and Samir said nothing as i turned around and did a little spin for them, shaking my bubbly ass a little, then as i walked over to them, i dropped my shirt behind me, so i turned around and bent at the hip to pick it up. I turned around again to feel Samirs bulge suddenly up against my ass, and his large hands firmly grasping my hips. Though i was a little afraid, him being an aggressive boy that often pushed me and my friends around, but i was so incredibly turned on by the attention i was getting and i couldnt stop myself from moving my small form against the growing bulge in his sweatpants.
Just as Jason was standing up to join the action, we heard:
“ITS 1AM BOYS, GET TO BED!”
My mother yelled down the stairs. Still wearing the bikini, i ran into our room, noting that my brother was fast asleep in his top bunk. Just then Jason grabbed my hips hard from behind. “Stay in the bikini faggot.” He whispered in my ear. As mean as it sounded, my cock flinched at being treated like a little whore. I got into bed as the boys took off their shirts and pants, making their bulges look awesome, and they turned out the lights and got into bed shortly afterwards.
In my horny state, i couldn’t sleep, but i couldn’t just walk to the bathroom and get myself off for fear of someone seeing me in my sisters bikini. While i lay wide awake, i heard some movement from Samirs bed. I looked over to see a very large bulge under his sheets, as he maintained a steady rhythm of movement under the covers with his eyes closed. Instantly my cock stood at attention, and in the silky bikini bottoms, my frustration multiplied at the wonderful sensation of them rubbing against my little hole.
As i watched his large hand slide slowly up and down his huge cock, i felt Jason doing much the same behind me, only his cock was quite close to rubbing against my bikini covered Rotterdam Shemale ass…
I tensed up, not really knowing what to do as he moved slowly closer. I was horny as hell but i was scared to move because i thought he guessed i was asleep while he grinded his cock against the soft fabric of the bikini bottom.
Slowly and carefully, Jason pulled at one of the tiny little spaghetti straps on the side of the bikini bottoms, removing my last line of defence between Jason’s precum-covered cock and my feminine virgin ass…
He spat in his hand and i felt him lube up his thick cock between my cheeks. Was he actually going to fuck me? I was terrified but oh so horny, and although id never admit it, this is exactly what i had wanted from the moment i put on my sisters skimpy little bikini.
Jason moaned as he rubbed his hard cock between my cheeks and kissed my neck, making me want to moan out loud so badly, but i didn’t know if he’d still fuck me knowing i was awake.
His cockhead was brushing against my tight little asshole more and more aggressively as his breathing got louder.
Suddenly, everything stopped. His cock was slowly stretching my entrance, and i almost screamed, but instead i held my breath and I opened my eyes wide. As i looked up, Samirs eyes met mine, but he maintained his steady rhythm, up and down his now completely bare 8″ cock.
Jason’s breath was suddenly hot on my ear.
“I know you’re awake you little sissy faggot. If you yell out or tell anyone, your whole family will know you’re a little crossdressing perv who gets hard wearing his sisters bikini.”
I just nodded. I was scared to move, as his cock very slowly stretched the entrance to my ass, and it hurt like hell. At the same time though, i was so damn horny, and i just wanted him to make me his girly little slut.
All of a sudden he pushed the length if his cock deep into my ass. I nearly passed out from the excruciating pain but i stayed quiet, breathing hard through the pain, as i felt his thick cock violating my virgin ass.
“Thats a good little slut”
It felt so incredibly weird to have my brothers friend’s cock buried in my no-longer-virgin butt, but the pain began to slowly fade as he slid his cock out of me, and i began to feel the beautiful sensations of anal sex begin to kick in.
He pushed it in again, making me moan louder than i meant to, and he dug his nails into my hips to stifle my noises as he pulled out once more.
I was so confused, yet so aroused and the only thing i could think of was the large cock inside me, twitching and beginning to massage something deep inside of me.
I knew i was addicted to the feeling, and i badly wanted more. I pushed back onto him with his next thrust, this time stealing a moan from him.
“Oh you love this dont you you little sissy bitch”
I just moaned softly again Netherlands Shemale and thrust him further inside of me in reply, and he picked up the pace.
A fiery heat was building inside of me and with every new thrust I enjoyed the sensations more and more. My cock was straining against the front of my sisters bikini bottoms as Jason fucked my tight little ass faster and faster.
I looked over to my brother who was somehow still fast asleep, and then to Samir, who was most definitely not fast asleep, and watching me as he got out of bed, his hard cock waving in front of him obscenely.
The moment i saw it, i knew where he wanted it. Samir moved to the edge of Jason and I’s bed, and touched a precum covered finger to my lips. I instinctively opened my mouth to suckle that sweet cockjuice from his finger, but he quickly removed it, placing his cock between my lips instead. I sucked it deep into my mouth, tasting his sweat, precum and just a little bit of piss from the day on his fat cockhead. He then pushed it close to the back of my throat. I got the hint, and grabbed it with both hands.
As i lovingly rocked my girly ass into it’s very first defiler, I worshipped the chocolatey cock that invaded my mouth, and i loved it. I could tell my brothers mates loved it too, and as i got spitroasted, i couldnt help but wonder if this would happen again tomorrow night.
Just as my thoughts began to wander, i felt Samir’s cock hit the back of my throat and stiffen. He stood dead still as he watched my eyelashes flutter at him helplessly while Jason broke me in. He had a sadistic look in his eye and scoffed as he shook his head, but in return I locked my lips tight around him and slowly sucked from base to tip. He laughed loudly as he burst, and he proceeded to empty his balls into my mouth, then onto my lips and cheek.
Samir backed away, leaving the last squirt of his cock to land on my chin, and he quickly retired to his bed. Jason on the other hand was still preoccupied with my voluptuous ass, and as he buried his teeth into my neck, i relished every moment, knowing he was close to cumming, just from a little sexy teasing and my feminine ass.
“Im gonna make you my little slut you got that?” He said harshly between his groans.
“Cum in me Jason. Im your little slut and badly need your cum baby” i moaned over my shoulder. I knew he wanted this, and i could think of nothing more than being his little sissyslut for the rest of the holiday.
He stiffened, and so did I despite barely touching my member, his cock touching my sweet spot just right. We both came incredibly hard as i rocked my ass back onto his cock, milking his cum from him. His hot spurts of cum fired deep inside me as mine fired into my sisters bikini bottoms. Jason bit my neck again and moaned loudly as he released his final drops of cum inside of me.
I was in heaven, and clearly so was Jason, and we both fell asleep quickly, with his cock deep in my ass and Samir’s cum slowly drying on my cheek.
Thanks so much guys and gays! Give me feedback pleeease and id love some tips on where to go with a potential sequel.
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