Note: This story series includes depictions of gay and straight sex between teenagers. If that's not your thing or if it is illegal for you to read this story, then stop. This story is completely made up and does not depict anything true.
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Characters: Me: Jesse - 14 Freshman
My Sisters: Stephanie - 16, Sophomore Melissa - 18, Senior
My Sisters' Boyfriends: Lukas - 15, Stephanie's boyfriend, Sophomore (the twink) Shawn - 18, Melissa's boyfriend, Senior (the stud)
My Sisters' Boyfriends - Part 2 Saturday 8:00 p.m.
After ice cream, no one said a word. This was usually when they would put on a DVD and make out, so I went up to my room to go on Facebook, play games, and try not to jack off. That'd have to wait until they went into their own rooms. I didn't want mom calling while I was mid-stroke.
There was a soft knock on the door. My sisters entered. The boys were behind them, but hung to the entryway.
Melissa pulled me to the bed. They sat on either side of me. "Jesse," Melissa began, "so we have a little surprise for you. You have been great tonight and we know you'll keep our secrets about the rest of tonight from mom and dad." I nodded reflexively. I had never told our parents about anything my sisters did.
"'Liss and I won the game," Stephanie continue, "and therefore we are making the boys do something we think you'll like. We know you haven't had much..."
"...any..." Melissa interrupted.
"Any experience with...girls or with..." Stephanie hesitated. She was about to raise the issue we had never discussed.
Melissa was always much blunter. "Jess, we know you are gay. And we don't care. And we love you. In fact, we kind of think it makes you much cooler."
I began to protest - not so much the fact that I was gay, buy how direct she was about stating it. Maybe it was a phase. Maybe I was bisexual. Maybe...
Stephanie refused to let my mind go that way. "Jess, we could name a million things that have made it clear, but mostly you are our brother and we know you better than anyone. We also know you think our boyfriends are hot."
"Cause they are!" Melissa laughed.
"And we thought as a reward for you, we'd make them try something new. So each of them are going to give you a fantastic blowjob. One now. And one later. That's what our reward is for winning - seeing them do something new, and seeing you enjoy yourself." Stephanie gave me a hug.
"You're going to watch?" was my first response. I was still absorbing this much new information in such a short period, but that's what stood out.
"That's part of our prize. And let's be honest, J, you've watched both of us a few times. Okay, I leave the door open sometimes, but you've stood there for a long while, don't think I haven't noticed." I blushed as Melissa looked at me. She had no displeasure - she liked the exhibitionary nature of some of her lovemaking. In 5 minutes, so much was now suddenly out in the open.
At a wave, the boys entered. Their faces were blank. Shawn was such a studly fantasy. His big muscles with a tight t-shirt pressing against it. He had dark black jeans and boots on. An Illinois State sweatshirt had been on when he arrived, but he had lost it during the evening. Lukas had on a colored yellow polo with a blue cashmere sweater. His ear was pierced and the gold stud reflected my bedroom light particularly. He always looked adorable, but right now he had a bit of fear behind his eyes.
"Nervous?" I found the backbone to call out.
It took a moment for Lukas to realize I was talking to him. "No, I mean yes, I mean not about this. Shawn is going first. I'm actually nervous because..." he got embarrassed and stopped.
Stephanie, who was also uncomfortable, found the words to continue. "We decided to honor the boys' prize too, so I think Lukas is nervous to be with Melissa. He has only been with one girl before."
"Steph!" Lukas was horrified his girlfriend would admit he was a virgin before they had started dating.
"Let's get this going," Shawn grumbled.
"Attitude!" Melissa barked. "This is a special prize for my brother - and a first for him. And a first for you, too, I assume? Unless the rumors about the football team are true."
"Yes, this is a first for me, too!" Shawn blurted, but then realized it made him seem hostile. "I think know what to do though, so you all can back up."
Surprisingly, my sisters let him be in charge as he beckoned me towards him by the side of my bed. I kicked off my sandals and stood with a white "Westview Middle School" t-shirt and cargo shorts that I wore inside our warm house. It never occurred to me to not let this happen. Shawn stood in front of me and as our eyes met, I sensed his ambivalence and apprehension. He had been on the receiving end many times, but suddenly was on the giving. Further, he had to get past his own gay hang-ups, the age difference, that I was his girlfriend's brother, and that he had an audience. I wasn't sure any of those except the gay thing was really an issue.
Shawn was about 9" taller than me, so when he dropped to his knees, it felt exciting and powerful. His strong, thick fingers moved to my fly and pulled open the snap then lowered the zipper. I wished I had known this was coming as I would have word sexier underwear than simple tighty-whities. My shorts were around my ankles, but I kicked them away so they would encumber my stance.
My dick was mostly hard in excitement and anticipation. Only sheer terror kept it from its typically perpetual state of bonerdom. This was a fantasy I had - although without the audience - many times. Being a complete virgin, I had never had the touch and breath of another on me in a sexual way. This was awesome. I kept looking down at Shawn, unsure of how I would respond to my sisters' simultaneous gaze.
He rubbed the front of my crotch over the white cotton fabric making me shudder. I figured he'd make this a quickie with a handjob taking me most of the way. But Shawn seemed to take his role as my first seriously and was stroking me gently. I knew he'd never kiss me like those pseudo-straight guys online, but I could live with this.
"Someone seems to know what he..." Melissa began some snide remark that was silenced by a sharp glare from both Shawn and me.
"You watch. You do not say a word. You only watch. Got it?" Shawn stared down my sister. She meekly nodded in agreement. It was a rare moment of a guy having the upper hand on her.
Shawn turned back to me and rubbed me a few more times before grabbing my underwear elastic and pulling it forward and down. My erect cock stood at attention in front of my handful of pubes. Shawn helped me remove my underwear completely. My t-shirt now fell on top of my dick, so Shawn stood up and pulled off my shirt leaving me completely naked.
Back on knees, Shawn seemed to be examining my circumcised member. I wasn't very big, I thought, although I mostly had online videos and photos of older teens and adults as reference. He began to blow warm air on my head and one of his hands cupped my balls, gently massaging them.
Without a warning, he mouth opened and engulfed my dick. Whether a result of size, natural skill by Shawn, previous experience he omitted, or simple beginner's luck, he took in my member instantly and soon was working it in and out of his mouth letting his tongue massage and tickle the underside. His lips formed a perfect circle and I found myself fucking his face.
"This is so fucking hot," Melissa loudly whispered. At the sound of her voice, I involuntarily looked up. There were my two wonderful sisters staring eagerly at watching me get blown. Somehow I found it exciting, not twisted. Then I saw Lukas' face. He was transfixed, probably seeing his first blowjob as an observer, and his sweet features made me harder. I looked down at Shawn and was transported as I saw this incredible stud holding my cock with his mouth and hand. I began to moan quietly.
"Shit!" Melissa mumbled as she raced across the room, past Shawn and me, to grab the phone.
"Hello? Hi Mom. Yes, it is fine here. You don't have to keep calling. We're not going anywhere....How's Aunt Susan...fine." She beckoned Stephanie closer and handed her the phone. Now I was being blown with my two sisters both a couple feet away.
"God, Mom. We just spoke an hour ago! Let it go. If you didn't trust us, why did you leave us home? Jesse is fine. Yes, we're taking good care of him. The best care. No, he can't talk now. No. Okay. Okay. Okay!!" Stephanie pulled the phone cord to its limit and handed me the phone. She had to be insane.
"Mhuhh?" was all I could manage. Shawn hadn't stopped for a second. "Fine. Fine," I squeaked out. As my Mom started asking specific questions, I pushed Shawn off me for a moment and blurted out, "I gotta go to the bathroom, Love you, Bye." I tossed the phone back to Stephanie who simply said goodbye and hung up. Just like Mom to interrupt my first blowjob.
Shawn renewed his work. I grabbed his head and began to push myself deeply in his mouth asking him to go "harder." I felt instantly my rising ejaculation was on its way. I wasn't going to say anything, but simply kept plowing the waiting mouth of my sister's hot jock boyfriend's mouth.
"Unnnngh," I grunted as I was about to blow. That was enough of a signal for Shawn who grabbed my t-shirt with one hand and stroked be with the other. As I exhaled deeply, I began to shoot into my shirt. My load came out quickly and then my cock became sensitive. I grabbed Shawn's hand to stop him from stroking so hard before pushing it off entirely.
By the time I was completely spent, Shawn was already standing and straightening himself out. He gave me a happy nod and walked out of my room. Lukas followed. The girls, with giant smiles, thankfully didn't ask me how it was or anything, but each kissed me on the cheek, despite my naked form, and went their merry way.
"Leave us alone sweetie?" Stephanie reminded me as she headed down the hall closing my bedroom door behind her.
To be continued...