Just as a warning, this chapter doesn't have a lot of sex. It's just this experience I had with these two guys which didn't lead to anything but was interesting nonetheless.
P.S. I was 16 at the time.
The four days babysitting were uneventful. The kid’s parents had gone on a business trip for four days and needed someone to look after him and my parents, being really good friends with them, promptly signed me up for the job. The kid was actually 13 and kinda cute, named James. He was of average height for a 13 year old, with ever so slightly pale skin, rust-coloured hair and blue eyes. He was skinny as well, with the first mild bumps of a six pack. And his cock, when flaccid, was not that big. I didn’t get to know his actual boner size, but I’m guessing it was between 4 and 5 inches. That was also pretty average at that age. He was a cool guy, and I did feel sort of attracted to him. In fact, I wanted his cock in me. So the second day of my stay I went down only wearing my speedo and he did grab my ass, which raised my hopes up a bit.
So, we discarded everything we were wearing and began a nudist lifestyle. His friend, Kean, who came every day, welcomed this new development with open arms and I nice naked body. Kean was Indian and so had the same brown complexion as me. It was a matter of shame that, even at being 13, he was a few inches taller than me (I was slightly shorter than average, as I previously said and Kean was taller than average). He had small stringy muscles in his arms and a better-built six pack than James. His cock, I’m guessing, while erect was probably 6 inches which is a good length for a 13 year old, but looked small on his tall, lanky figure. Somehow, the combination of these two made my metaphorical ovaries explode. I know it’s ever so slightly creepy, but I guess the newness of it all and the new fantasy I was having (of these two being my students and I being their teacher in a ‘Sex Ed’ class) just increased their appeal in my eyes.
The closest James’ cock got to my ass was when we slept. The first night, I kept the guest room door unlocked in case he needed me. The next morning, I woke up to find him hugging me from the back, the bulge in his pyjamas pressing against my buttocks. He was asleep, so I guess it wasn’t on purpose. Unfortunately, I was also wearing pyjamas. This is why I decided to go nude. The second night, his actual erect cock was buried between my butt cheeks and I felt content. Even then, I couldn’t change the fact that the guy was straight.
The first day, I told him I needed to use his computer to chat with someone on skype. I hadn’t been allowed to bring my own computer, therefore I depended on him. I also told him that these were exceedingly private conversations so he couldn’t come into the room while I was having them. He was alright with that, although he told me that there was no key for the computer room because his mum had taken it away.
“Why?” I asked.
“My parents were gone to a party once,” he began, smirking slightly. He wasn’t shy to talk about sex, because that was one of our main topics besides food, drugs, alcohol and James’ immature girlfriend. “And I was playing games. It was getting late into the night and I went up to bed, but you know when you haven’t wanked all day and you can’t sleep just because of that? Yeah? Yeah, so I went down, locked the computer, but the porn on that small TV there and put it on full volume. Unfortunately, my parents came, although I didn’t hear them. I did hear them knocking on the door but somehow that just made my final orgasm stronger. It’s so intense when you can get caught. But when I wiped myself and wore my clothes and opened the door, it was really embarrassing.”
I chuckled, “I’ve never had that. I’m too paranoid. But I swear parents are really immature about the porn thing. They know that all teens will watch it at some point, so why not just let them?”
“Yeah, I’d never do that to my child,” James sniggered, “He can have a wank in the same room as me and I’d be okay.”
“That would actually be very awkward.”
“I just kid. But I was a teenager when this happened. I was 11.”
“So you were a tweenager. Close enough.”
Well, these exceedingly private conversations were with Dave, who was still in SA. And they were exceedingly private because we had cybersex/camsex whatever you call it. Honestly, I did hear the door creaking a bit three times during my stay but I guessed that was just the door. It wasn’t a particularly new door and it didn’t properly close so I guess it was swaying slightly all the time. The third time this happened was the worst time because I was cumming all over the webcam and the sudden creak just took all the enjoyment out of the orgasm and turned it into terror. It did make me shoot more load, though.
Anyway, the last morning I woke up, I realised this was probably going to be the last morning I was going to be feeling James cock lodged between my butt cheeks so I didn’t get up immediately as I usually did. I stayed there for what seemed like a long while, savouring the feeling of that innocent, virgin, uncut dick showing its love for my ass.
“Good morning,” James yawned suddenly.
I had a split second of terror which vanished when I realised that James should be the one who’s scared.
“Morning James,” I replied, “I don’t mind it being there James, but can you please tell me where your penis is at the moment?”
“Erm… oh, sorry!” he said frantically as he pulled his dick away.
I turned around, looking into his eyes, chuckling a bit. He mirrored my expression. “It’s okay James,” I said, “You’ve been doing it every morning.”
“What, really?” His expression had gone back to the guilty one.
“But because I’m gay, I don’t really mind. I like it when cocks like me, and yours does a lot.”
James laughed. Me being gay wasn’t news to him because that was the first thing I told him over breakfast. “Can’t help it, my cock is gay but I’m not. We have an interesting relationship.”
“Well, I’m guessing it likes both your hands because both of them are male,” I chuckled.
“I never thought of it that way,” James wondered, “But that only means my right hand. My right hand is the gay one. Wow, I’m gayer than I thought.”
“James, I’ve always wondered why you’re so okay to live with a nudist gay guy who is bigger and stronger than you and so can get you whenever he wants.”
“Because I knew this big, strong, nudist gay guy is my friend and would not harm a mouse. And because if anything does happen to me, I wonder what my parents will say to yours…”
“Clever boy.” It was a sudden impulse, but I couldn’t resist the urge to hug him tight. I did control my cock however, which was a surprise. “I’m going to miss your cock, James. Every morning I woke up to find it lodged in between my butt and every morning it raised my hope that you might be bi at least, but I guess I can’t have everything I want.”
“And I’m going to miss your butt, Ali, even though I realised only today that my cock was renting it every night.” James paused and we parted. He looked into my eyes and said, “But I feel very flattered. I didn’t know you liked me so much that you wanted me to be gay.”
“Why are you surprised,” I said through a sad smile, “You’re very cute.”
“You think so? I always think I’m too skinny to be hot or anything.”
“I never said you were hot, only cute.”
“There’s a difference?”
“But I want to be hot!”
“You’ll get there eventually, but right now just revel in your cuteness.”
“Okay.” James put his hands on my shoulders. “I feel bad, though. I’m straight so you can never do anything with me.”
“Oh, I can. It’s just I’m too nice.”
“Yeah, I guess that’s why I haven’t called the police yet.”
“Hmm…” I said, pulling James closer. “Just stay near me. I really like it.”
“Wow, this is getting really creepy really fast,” James chuckled.
“And you think putting your morning wood on my ass wasn’t creepy.”
“It was, but the difference is I’m awake.”
“I really can’t resist the urge,” I confessed.
“The urge to what?” James said, puzzled, fear showing the first time on his face.
“Well, what urge could I be talking about, of all urges?”
“Please don’t…” James shook his head fearfully. I just realised my grip on him had tightened to a large degree. I loosened myself up a bit, but he stayed.
“Don’t what?” I asked in a comforting tone.
I looked at him, furrowing a brow. And then I realised what was wrong. “Gosh, I don’t want to rape you. It’s the other way round.”
“What?” James was the confused one this time.
“I want your cock in my ass, not the other way around.”
“Oh…” James laughed in a relieved way, “I don’t know what to make of that. I’m sure it’ll feel good, but…”
“Oh never mind, I know this is never going to happen.”
James looked at me with what seemed almost like pity. I didn’t like it. “I’m so sorry,” he said.
“Don’t say that.”
I pulled him much closer so that our chests were flattened against each other and we could feel our breaths. He was trying to keep his cock away, but I’d waited too long. I put a hand on his ass and pulled him towards me. Our cocks touched and his eyes widened. “I’m so sorry, James,” I said. I started nibbling his neck, writhing so that my cock slid all over his cock. I kept his legs imprisoned by twining them with mine. As I kissed his neck, he moaned, “Ali… this feels nice but…”
“If it feels nice,” I replied, “Then don’t be ashamed to do it.” My index finger started exploring his asshole, and when I pushed it up his hole, he gasped, “Fuck!” At this point, I didn’t care whether it was a positive gasp or not. I had already gone too far.
“Please, Ali, let me go!” he said softly. Somehow, that voice pierced through the horny parts of my mind and met reason. I let him go.
“I’m so sorry, James,” I repeated.
“I didn’t know that anyone could like me this much,” James said, astonished, “It felt so good. I’ve never done anything like this with Mathilda.” Mathilda was his girlfriend. The most they’d ever done was kiss on two occasions.
“If it felt good, why did you stop it?”
“Because I don’t want to be gay. Everyone will make fun of me.”
“Whatever we do doesn’t leave this room.”
“But it’s wrong!”
“No, if it feels good and it’s not killing you or anyone else, it’s right.”
“But I don’t think I’m gay.”
“You don’t have to be gay to enjoy this. People who call themselves straight still do stuff with guys because it’s fun with no strings attached.”
“But I have a girlfriend!”
“She doesn’t sound like a real girlfriend anyway.”
“Yeah, I guess.”
I was tired of this. “Do you want to do this, or no?”
“Then at least let me wank off to you.”
“Maybe at a different time.”
“What do you mean?”
“Maybe if we have another sleepover, I will…”
I didn’t care. Immediately, I pushed the blanket off the bed so the sunlight fell on our boners. I pulled him in and started wanking myself. He tried to push himself away but I was, in the end, bigger and stronger. “What are you doing?” he asked in a horrified manner.
“Just having a wank.” I stroked my cock at the perfect pace – not too fast, not too tight.
I pushed my bellend against his torso and he said in a sick tone, “I’m feeling something wet.”
“Fuuuuck… James,” I moaned as my hand went up and down my shaft, as drop after drop of precum I rubbed on James. I pushed my cock against James’ and rubbed it with precum. I revelled in every bump and vein, adding more spit as it ran dry. And then I blew my load all over his cock and abs.
James didn’t do anything. He went to the bathroom and washed himself before coming outside. His boner was gone already. “Happy, now?” he asked, not waiting for me to reply. “I’m happy. I used your cum to wank myself off. Am I gay? No. Do I have any interest in you? No. Now don’t tell anyone what happened. I don’t want anything to do with you.”
That evening, as I was packing my things, feeling very guilty about the whole matter, James came into my room and hugged me tight. His boner pressed against my butt, so I was surprised. I turned around and hugged him tighter, pushing my hard cock against his. “Listen,” he said, “I’m sorry, I guess I was a bit harsh. But you were as well.”
“It’s alright, I shouldn’t have done that,” I agreed.
“But I liked it, surprisingly,” James sniggered, “Listen, the next time you come over, things will be different. I’ll bring Kean over as well. I’ll not let you regret this.”
“What do you mean?” I asked, thinking of a threesome.
I kissed him, and although he didn’t exactly reciprocate, he didn’t pull away either. When I stopped, he just stared at me, saying, “I really like you, I’m just sorry I don’t like you that way.”
“You’ll see,” I said this time.
Kean was standing in the doorway. “What, don’t I get any hug or kiss?” he chuckled.
“Well, I didn’t exactly blow my load over your cock,” I reasoned.
“Still, every relationship has to have a beginning somewhere.” He ran towards me and jumped. I caught him, but fell onto the bed. I kissed him as well, and he did reciprocate, although he was horrible. I didn’t get what was going on, but I went along with it. Kean held my cock and gave it a few tentative strokes, but nothing really happened. I clothed myself and after giving James a hug and Kean a make-out sesh, I left.