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Chapter 2: Strip Games
It started as just a friend event. We were going to Myles' house, my cute, "85% straight" friend. The other people who were going were Jacob, Grayson who was also 15 but looked young for his age, more like 13. He was insanely cute but most definitely straight, and there was Myles who was 17 like me. We started the party with Myles, Jacob, and me smoking weed. Grayson wasn't allowed to smoke (his dad was a cop) so he declined.
We hung out in his garage and played pool until like 11 at night, when it got too cold we decided to go inside. Myles' room was big and had one queen bed and another small single size. Throughout the night I wondered who I would share a bed with. I had my eyes on Grayson as he was just so cute, but I was still super horny for the other two boys as well. As long as I shared the bed with one of the boys I would be ecstatic. My cock was hard just thinking about sleeping with three cute guys nearby.
The night started tame. We were just talking for like an hour until things turned slightly more sexual. We talked about previous partners and our sexuality, and I found out Myles was mostly straight but would be with a guy just to try it. Jacob, as I already knew, was bisexual, and Grayson kept insisting he was straight despite our jokes and probes, which was kind of unfortunate. Someone, I think Myles, made a joke that we should play some type of stripping game. Everyone laughed since that's only something in movies, but I secretly wanted it to happen. Apparently, others did too, since it kept getting brought up. We kept going back and forth on the best variation of the game until it just sort of happened- we kept joking about playing it until we actually were starting to play it. We decided on asking a question to another person, and if they declined to answer, they would have to remove an item of clothing.
I went first, asking Grayson a question. I had an opportunity to see that boy's underwear. Hopefully, the group would go that far- I heavily doubted anyone would go further. I didn't think I would have the courage to go to my underwear, that I would pussy out when my shirt was removed. Even that isn't something I've ever done in front of them unless we were swimming.
I asked Grayson if he kissed anyone. Disappointingly he answered the question, answering with a surprising no, not taking off any clothing. He asked Myles something to which he answered with a smile, staying fully clothed. Myles asked me which of the three of them was the cutest, and my heart fluttered a bit from nervousness. I took the opportunity to take my shirt off, the first one in the group to show some skin. I asked Jacob if he had ever done anything sexual before. Jacob seemed embarrassed, which answered my question, and to my surprise, he took his pants off to reveal red and blue loose-fitting boxers. His shirt disappointingly was still covering his bulge area, but seeing this high up his thighs definitely hardened me up quite a bit.
"We should introduce dares into this!" I suggested as Jacob seemed to struggle to come up with a question. He smirked, and Grayson and Myles seemed to agree with my idea. Jacob dared Grayson to text his crush, and Grayson got blood red in the face. "Do I have to take a piece of clothing off?" he whined. "Only if you don't text them right now," said Jacob.
To my great pleasure, Grayson took off his shirt. His smooth chest had soft lines outlining his lean muscles, not a hair on his chest to be seen. As he lifted the shirt above his head, I could see wispy armpit hairs, not as grown as the rest of the group. He was so cute!
"I guess it's my turn," Grayson said, looking at me. I snapped out of my stare at his body and saw he had a slightly puzzled look on his face for a split second. He totally noticed, oops. "Henry, what body part are you attracted to the most?" Grayson asked me. I debated answering, but at this point, my bulge would be visible if I had to take my pants off. I didn't want them to know I liked guys, worried they would want to stop the game. Although dick was my real answer, I just responded with "ass" since it was gender-neutral.
Finally, it was my turn again. Myles was fully clothed, Jacob had his pants off, and Grayson and I both had our shirts off. I was surprised we were still playing, especially since during the hot summer night, none of us were wearing any more layers, not even socks. Even though Myles hadn't shown skin yet, Grayson's skinny twink body was really turning me on. It would be too suspicious to ask him again, I decided. I looked at Jacob. "Truth this time," I told him. "You're bi, right? What's the hottest part about me," I asked him, trying to sound like I was joking around. Jacob blushed slightly.
"You're extremely ugly I can't pick anything hot," said Jacob jokingly.
"Ouch! Well, I guess you have to take a piece of clothing off then," I said to him as another joke. Surprisingly he obliged and slid off his shirt, revealing a more built chest than anyone else in the room with the thinnest hairs on his chest. He was now just in his boxers, and although his dick was 100% soft there was a bulge to be seen, for his age it looked like an impressive 4 inches. Although not as gorgeous as Grayson, he was still cute.
"Hmm my turn," said Jacob. He pointed to Grayson. "I dare you to scream as loud as you can," Jacob told Grayson. We were in Myles' parents' house and it was nearly midnight, they were definitely sleeping.
"Dude I can't do that," Grayson responded. "You guys are mean!" He said. But after some hesitation, he sighed and unbuttoned his pants, slowly sliding them down his legs. I couldn't believe this was happening! I instantly got so hard. His hand was embarrassingly covering the front of his undies to my disappointment. He was wearing quite tight boxer briefs, bright red.
"Dude we are just guys, plus you're wearing underwear," said Jacob. Grayson sighed and removed his hand. In these undies, you could see everything. His outline was small, maybe 3 inches, but he looked soft.
"Myles this isn't fair your clothes are fully on," said Grayson. He thought for a moment. "I dare you to punch Henry as hard as you can." "In the face," he added, smirking. Myles looked at me, my eyes wide.
"I'd never do that," Myles said.
"Exactly," said Grayson quietly. Myles sighed and removed his shirt. He was cute, too! Now everyone was shirtless, with Jacob and Grayson down to just their underwear. It was so hot that Grayson's underwear appeared a size too small for him, stretching over his still limp noodle.
"My turn," said Myles. His face lit up with a grin. "Jacob, I dare you to go in my closet with Henry and Grayson. You're not allowed to leave for 5 whole minutes." We all looked at each other.
"What's the point of this? It's gonna be so boring! Also, why am I looped into this?" said Grayson. Myles disregarded the first question.
"If Jacob agrees, you have to do it. It's the rules," he stated.
"Yeah I don't care," said Jacob. "Easier than the other dares you sadists have been asking.
My heart was pounding. I glanced at Myles' closet. It looked tiny, would all three of us be able to fit? Myles got up and opened it. "Well in you go," he said to us, smiling. Not only was it small, but his clothes were in it making it even fuller. Jacob went in first, crouching as far into the back corner as he could to make room for us two. I followed, sitting on the floor my back leaning against a side wall. My crossed legs took up nearly the entire closet floor thats how small it was. Grayson groaned and stepped inside, his two feet having nowhere to go but between my crossed legs. He stood hunched over, his top half submerged in Myles' hanging clothes. The three of us just barely fit inside.
"See you in five minutes!" Exclaimed Myles, shutting the door. The door closing hit Grayson who toppled over, falling legs-first onto my face. His underwear and bulge were on top of my head, and my face was on his thigh.
"Sorry!" he said, trying to get up, eventually succeeding. My forehead brushed his clothed member several times making me even harder.
"You're -uh- good" I mumbled back. It was pitch black inside, I couldn't see anything at all. The only senses were the smell of boy sweat and deodorant, the feeling of our legs nearly tangled, and Myles' clothing in the black box of the closet.
After Grayson succeeded in not falling into Jacob and me, he was crouched more than before. I couldn't see his position but I could feel his warmth right in front of me. Specifically, in front of my face. As the three of us were struggling to find a comfortable position, I gently moved my head forward and my face collided with some fabric. Specifically, Grayson's underwear. A minute had gone by. My cock was so hard being this close to 2 boys I found so cute. I moved my head forward again in the chaos and felt Grayson's underwear on my face. He seemed to not notice, at least he didn't say anything. This time though, I could swear he was slightly stiffer, at least not completely soft. I was too nervous to hold it there so I moved back into position.
I could feel Jacob's heat next to me as well, his legs brushing against me every so often when he moved to find a comfortable position. None of us said anything, all of us breathing heavily struggling not to topple over again. My cock felt as if it would explode as the reality of what was happening set in. My straight crush Grayson, and another cute boy from his grade were in a pitch-black closet with me, nearly naked, for an uninterrupted 5 minutes. I was too anxious to outwardly do anything sexual to them in fear of being exposed but I needed to do something to relieve my throbbing member.
I slowly reached down and grabbed my cock through my sweatpants. I moved forward an inch again to feel Grayson's bulge, and if I could believe it he somehow had a semi. His warm cock was on my cheek, blocked by the smallest of barriers. I had no idea how much time had gone by as I stroked myself through my pants, holding my face softly on Grayson's underwear. Every few seconds it would brush against me, sending a tingle down my body to my cock. I carefully pulled down my sweatpants over my bulge just to relieve some of the pressure, which nobody would notice with the movements going on in the dark closet from the others. I continued stroking my dick, much easier with only my underwear.
Against my face, Grayson's cock was getting harder. He wasn't saying anything, maybe he thought he was brushing it against Myles' hung-up clothes? I kept stroking myself and could feel I was almost done while Grayson was nearly full mast. It must have been nearly 5 minutes, and finally, everyone seemed to find a spot since there was less shuffling. I was comfortable on the floor, Grayson was standing right in front of me, underwear and bulge right in front of my face, and I could feel Jacob's warm skin against my leg in the corner of the closet.
"Is it time yet?" Grayson asked quietly, sounding nervous. Was he embarrassed about getting hard?
"Dunno," said Jacob. I stayed silent, pausing my stroking until I could quietly resume. I was so close to cumming this was so hot. I breathed softly on Grayson's bulge, lips inches from his hardness. I wish I could see him right now, I had no idea his size. Debating whether to cum or not, I decided it was too risky even though I wanted to shoot my load all over that closet. It felt like it had been over five minutes but I wasn't complaining. I put my ultra-hard dick back into my pants and continued brushing softly against Grayson's warm hard member, careful not to let him know my intention.
Suddenly, the door opened and light flooded the closet. Very briefly, I saw Grayson's boner outline. It was pushed to the side of his underwear and looked 4 or 5 inches and quite thin. I also noticed out of the corner of my eye that Jacob covering was the front of his underwear. He was hard too! Quickly after Myles opened the door, Grayson covered his cock with his hand.
"Finally!" he squeaked, exiting the closet and dashing to the larger bed, presumably to hide his cute hard-on from all of us. Jacob didn't seem to care as much that he was hard, although he was attempting and failing to cover it with his hand. I still had pants on and didn't bother hiding my bulge since it would be more difficult to notice. Myles was fully clothed, he had changed into a new shirt and pajama pants. His bulge seemed more pronounced than usual, maybe he wasn't wearing underwear under his pj's?
"Anything spicy happen?" Myles joked.
"We had a huge orgy," Jacob joked back. Grayson stayed quiet on his phone, already in bed.
"Yeah we had hot gay sex," I added.
"Good," responded Myles, accepting our joke and believing nothing happened. We all sat on a bed, Jacob in the corner of the room on the small bed and Myles and I sitting on Myles' larger bed. "Now what, bedtime?" Myles asked.
"I'm tired," said Grayson already lying down, pretending to fall asleep. I wondered if he noticed what I was doing to his bulge. My heart was racing.
"I need to change," said Jacob.
"Me too where's my shirt?" I asked Jacob, seeing as it was next to him. He tossed it to me, once again giving me a view of his toned build. He tossed it to me before standing up and heading to the restroom with his clothes. I tried not to stare.
"Don't you want to get clothed?" Myles asked Grayson. Apparently, he had fallen asleep, as all he could respond with was a mumble. I guess that was a no. He looked so cute even as his skin was hidden, his back facing us and a mess of brown hair was all that was visible. Jacob entered the room with a t-shirt and sweatpants, his bulge no longer visible. He went over to the small bed and got comfortable. Being so tall, he barely fit.
"Where should I sleep?" I asked Myles. As much as I wanted to curl up next to Grayson and cuddle him, it was Myles' bed.
"Uhhh..." he thought, looking around the room. "Looks like Jacob got dibs on the guest bed. I guess the couch downstairs is available?" My eyes widened and my heart sank, I hoped this wasn't true and debated just going home so I could finish myself after what transpired in the closet. "Or we could probably all squeeze in here, huh?" Myles suggested innocently, gesturing towards his bed.
My heart raced at the idea of squeezing in bed with the two boys. Myles' bed looked smaller than a queen, maybe a full. The three of us would fit, but it would be tight. I wasn't complaining. My dick started getting hard again thinking about it. Sleepovers were a definite turn-on for me, and being between two cute guys?
"Works for me," I responded, happily taking that opportunity. I had planned on taking my underwear off before going to bed since I knew I would be hard the entire night, but I wanted to be in the middle before Myles took the spot beside Grayson. Myles stealthily winked at me. Did he know I was drooling over them, especially Grayson? First the closet, now this? I decided not to think too much about it as my heart rate increased and went into his bed, underwear still on, scooting closer to Grayson.
I leaned over him. "Hey, can you scoot over a bit?" I asked him softly. He turned to face me and obliged. Our eyes met. His eyes were a very pretty green. God, he was so cute, I wanted to just meet my face with his and kiss him deeply. I controlled myself and scooted closer to him to make room for Myles. After turning the lights off and saying good night to Jacob, Myles scooted into bed next to me. The room was dark but not pitch black like the closet, just enough to make out the boys' outlines.
"Goodnight Jacob," I called to him across the room.
"Sleep well Henry," He replied softly. Even hearing Jacob say my name adoringly made me grin. I could feel the heat of the two boys under the covers nearly inches from me. This was going to be a fun night.