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Click hereDisclaimer this story is purely fictional and all characters are over 18.
Jack woke up in a daze, somewhat disoriented by the nap he just took. When he checked the time on his phone it was 8:03 pm. He had a long day at school which included a few tests that he had been up late studying for the night before; additionally he was very tired after fucking my tight-little throat and spraying it with his cum. Naturally, when he arrived home he fell asleep as soon as his head hit the pillow. After waking up, he decided to deal with his hunger first. His parents were gone for the week which meant that he would have to fend for himself in the dinner department. He took out a frozen lasagna, for one, from the deep freeze and threw it in the microwave.
Then he began to think about the events from earlier that day. My words still flashed hot in his mind: "Cum for me you sexy twink"; "Good boy". He was pissed at how I played him like a fiddle but also a little turned on. With great reluctance he admitted to himself that he enjoyed how I tricked him and used him for my own pleasure before humiliating and teasing him. He also remembered how cute I looked with my long legs and round hips, not to mention my little ponytail and the cute knot in my shirt. Then of course there was my ass which felt and looked so good when he humped it. He stiffened a little in his shorts thinking about it. He stiffened a lot actually and elected to take off his shorts as going nude would be much more comfortable that trying to suppress his boner.
He got a pillow from his room and placed it on a chair in the kitchen. Still thinking about my ass, he began humping the pillow. At first he went slowly, gently grinding, enjoying the feeling of his cock against the pillow. His cock felt heavenly while gliding across the soft pillow case. He placed his hands on the far end of the pillow to hold it in place as he began moving a little faster. He savored the friction he felt in the sensitive spot below the head of his cock. He gave the pillow a firm smack pretending it was my ass and that he was punishing me for earlier. His cock appreciated the thought.
He pressed his hands down hard onto the pillow gripping it for dear life as he humped the pillow at full speed. He almost felt a hand on his balls as they stayed still, nestled tight against the warm pillow. His shaft flew fast, forwards and backwards over the pillow, pulsing as he neared his orgasm. Jack slammed his balls into the pillow and pumped his shaft vigorously with his hand. His body shuddered as sweet cum flew from his head. His cock pulsed and twitched as he came. He took a vape to steady his breath as he cooled down from his orgasm.
After cleaning up Jack took off his shirt and threw on a large sweatshirt-it was about two sizes too big for him-instead. The house was chilly as spring hadn't quite begun yet; still, he refused to wear pants and underwear while he was alone in the house. He sat quietly with his thoughts as he ate his dinner. 'Could I be gay,' he thought to himself. He had liked girls his entire life, but his attraction to me was undeniable; I had just made him cum twice. The thought perturbed him greatly. He didn't have any problem with queer people, but he felt odd when confronted with the reality that he might be one of them. It just didn't feel right. He carried that unease to bed with him that night as he struggled to fall asleep.
For me it was a mostly normal thursday. I hadn't been with many guys and I'd never messed with a 'straight' one before, but exhibitionism and cock sucking weren't exactly groundbreaking activities for me at this point. Still, I got greedy and wanted him inside of me. I painted my nails a fiery red and resolved to make a move on him the next day.
When I woke up I put a black skirt over my underwear. I wore a plain red shirt and had my hair up in a high bun. I put on some lipstick-it was red but not too saturated as to look trashy-and 'forgot' my glasses at home. I put on some shiny magnetic earrings that were silver in color. I took a small strand of hair from my bun and laid it over my face. I put a black sweatshirt over my shirt as it wasn't a cold day but it was still pretty cool.
I was planning on jumping him in the bathroom after school but I got lucky and didn't have to wait that long. It didn't happen often but occasionally the weights and PE classes would both be out on the field together. Being outside in either gym class usually just meant that they would throw you outside with some footballs, a kickball, and volleyball, and let you do whatever. I usually played some football or ran some routes, but that day I had some different balls I wanted to play with. I found the boy from the day before standing alone near the edge of the field. I got close enough that he could see me but stayed far enough that he would have to shout to talk to me. We made eye contact, and a little-mischievous smile spread across my face. He looked somewhat uneasy; I'd definitely wiped that smirk off his face. I took out my phone and pretended to text someone to show off my nails. Eventually when I thought nobody was looking I winked at him. I knew from the look on his face that did something for him.
I nodded my head towards the bleachers and he understood what I meant. Students often met underneath the bleachers to fuck. I'd never done anyone under there but I masterbaited there frequently. The staff knew what went on down there but they weren't receiving any complaints from parents so they didn't do anything about it. I could tell he was nervous when he arrived. I leaned in slowly for a kiss. After some hesitation he accepted it and we began a slow sensual kiss. I didn't like being the one in control when it came to the bedroom; I hoped he would be a little more forward after we fucked a few times. I dropped my underwear to my ankles and placed his left hand under my skirt and onto my ass. I loved it when guys would grip my ass. I moaned into his mouth a little while we kissed.
I leaned in closer and started feeling up his chest under his shirt. We stayed like that for a few sweet moments until I felt his cock poke my thigh. I leaned in even closer and began tugging his cock through his shorts. He took my hand and put it onto his cock, under his shorts. I was getting hornier and hornier as he played with my asscheek and I played with his cock. I desperately wanted him to turn me around and defile my hole with his cock right then and there; I knew he wouldn't be bold enough to do it on his own, and I did my best to stop myself; 'his first time with a guy should be done properly' I told myself.
I began jerking him off faster and faster as I moaned harder into his mouth. He gave my ass a good hard slap and then returned to groping me. I could feel the precum dripping out of my cock. He slapped my ass again and I moaned loud. His breathing was fast; his cock twitched; his hips rocked back and forth; his precum leaked all over my hand; and his shorts had a wet spot. Then right before his orgasm I stopped jerking him. I took both my arms around him, trapping him in a tight hug. He struggled against it, desperate to cum. After a few moments he had the sense to hump my leg but by then it was too late. I pulled down his shorts because I liked the feeling of his cock against my thigh but I still didn't let him get off.
I took my lips off of his. "What the fuck dude," he started before I put a finger on his lips and shushed him. I began whispering into his ear. "Here's what's going to happen. You're going to put your contact info into my phone, including your address. I'll come over between 4:00 and 4:30 and we're going to fuck. And be a good boy and don't cum between now and then; I want your balls nice and full for tonight."
My boner had faded to a semi and I was about to give him my phone when he began smirking. He loosened his grip on my butt and his fingers began drifting towards my hole. I gasped as he began rubbing his fingers against my hole. As he slipped a finger in my hole, I let out a soft moan. He started slowly wiggling his finger inside my bussy. I was growing harder by the minute. I took his free hand and forcefully guided it under my skirt, and to my cock.
He began to speed up a lot. I leaned into him; my arms wrapped tightly around his sides; my face nestled into his neck; my thigh rubbing against his cock. I would have fallen without his support. The sweet scent of my hair made his cock twitch a little. I began moaning wildly into his scrag which mostly muffled the sound. "Cum for me babe," he whispered to me. My cock swelled and bursted as he began pumping my cock and hole faster than ever before. Cum flew out of my cock all over the grass.
After a few moments I slipped my underwear back on. I slowly stroked his cock as he put his contact info into my phone. When he finished-with the contact info-I gave his cock a few fast tugs; I whispered into his ear, "Jack try to eat some pineapple before I come over"; I gave him a peck on the cheek and left.