Henry's life at the academy of Domination & Submission

Chapter 18: Summer Break Madness

It was the end of the summer and the new school year was three weeks away from beginning. I had a blast and made so many memories. The best part of the summer was that Ryan came to visit and stayed for two weeks. His poor little butt was so sore the entire time. If he wasn't getting wedgies, he was being spanked. I had ruined all of his cute undies within a couple days, but that just opened the door for us to go underwear shopping, which meant even more wedgies. After he left, things were chill and easy until this morning.

I woke up to my phone ringing around 8 o'clock this morning. I rolled over in my bed and looked at my phone and was surprised to see that it was Dan. He was supposed to be off doing some training for football for the next few days and wasn't allowed to have his phone.

Henry: Hello?

Dan: THIS IS TERRIBLE!

Henry: What? What's wrong? Are you okay?

Dan: NO AND NEITHER ARE YOU?

I was confused by his statement. I had to sit up and pay extra attention to what he was saying.

Henry: Dan, please calm down and slowly explain in detail what is wrong.

Dan: Ugh! Fine, so apparently the dean and a couple of his staff took off with a huge chunk of the school's money and stopped paying for a lot of the bills. The school is in danger of closing down, which means we won't have a degree and have to start over and miss SENIOR YEAR!

Henry: Oh... umm that's bad. I'll call Ryan and let's meet at that cafe in Hungvile.

Dan: Okay!

I quickly got out of bed and called Ryan. He said he would meet us there. I threw off my clothes and raced for the shower. I didn't have time to do my normal routine, which consisted of me jerking off before getting out of bed and once while in the shower. After a quick scrub, I pulled on a pair of yellow briefs, a pair of short shorts and a t-shirt before getting in the car and heading to the cafe.

When I arrived, I was the first one there. I grabbed a booth in the back and ordered a tea while I waited. Dan was the first to arrive and he was wearing his ratty practice shorts, that were so worn out that they were see-through black mesh now. Underneath you could clearly see he was wearing a classic jockstrap that was trying hard to contain his beast of a cock. When he turned to ask the waitress a question I was happy to see that the back was just as worn out as the front. His ample big booty could clearly be seen being pushed up by his tight jockstrap.

Dan: Sorry it took me so long, I had to run out of practice. I know the coach is going to be made, but it had to be done.

Henry: It's okay, I just got here not too long ago. I'm just waiting on Ryan now.

Dan: Ooooo the boyfriend...

Henry: Shut up, he just so happens to be a boy that's a friend.

Ryan: Oh really?

Dan and I both jumped when we heard Ryan's voice behind us. We looked up and saw a slightly annoyed Ryan, with a cheeky evil grin on his face.

Henry: RYAN! Heyyyyyy, how are you?

Ryan: Don't hey, how are you now.

Dan: Ooo you're in trouble...

Ryan/Henry: Shut up DAN!

Ryan: We will discuss this later.

Ryan sat down next to Dan and across from me, I could easily tell he was mad, but I'd worry about that later. We all ordered some breakfast and reminisced over our time at the academy, but the conversation quickly changed to how do we save the academy. That's when we came up with the idea of doing some events to raise money to save the school. We knew we would need some help and I had just the right people for the job. While we ate, I called up Brodie, Phill, Landon and Troy. All of them agreed to meet up at the cafe within the next hour. After I finished speaking to them I got on the phone with Jordan. I knew if anyone cared, he would.

Jordan: Hello?

Henry: Hey Jordan, it's Henry.

Jordan: Oh Henry! How are you?

Before I could respond to Jordan, I felt something in my lap. I looked down to find Ryan's sock covered foot in my lap. He was massaging my bulge and it was turning me on.

Jordan: Hello are you there? Can you hear me?

Henry: Oh yeah, ummm hi! I'm doing great.

Jordan: That's good to hear, so what's up?

Before I could answer again, Ryan's foot had found its way up my shorts and fully on my growing hard on. He was stroking the outside like he was giving me a hand job. I never knew he was this good with his feet. I could feel him put more pressure on my cock and really stroke me. I embarrassingly let out a couple moans and caught the attention of Dan and Jordan.

Jordan: Is this a bad time? Do you need to call me back?

Henry: Ohhhhh no, t...this is a perfect time... oh yeah.

Jordan: If you say so...

As I tried to talk to Jordan, Ryan kept giving me a footjob. It got to the point where I had to rearrange my cock so it was pointing straight up. Dan watched as all of this went down and didn't say anything. He knew Ryan was getting payback from earlier and he was enjoying it. I was able to stutter out the information to Jordan and he agreed to help. The conversation wasn't too long because Ryan had me on the brink of cumming for a while. He kept edging me, but wouldn't take me all the way. Honestly I didn't want to have an orgasm in such a public place.

Henry: Oooooh fuck, yessssss.

Jordan: Umm okay Henry, I'm totally in for whatever you have planned. Just get back in touch with me on how I can help. Talk to you later.

*End of phone call*

As soon as the call ended Ryan went into overdrive and I no longer could contain myself and let out all my moans. The cafe fell silent as my grunts and moans echoed throughout the space. I could feel my impending orgasm ready to burst through when...

Brodie: Well I see you guys haven't changed.

Landon: Horny as ever little Henry.

Phill: Ryan, I taught you well.

Troy: Can we start this meeting? I have a date and I will not miss it.

With the guys arriving and pushing us over in the booth, I didn't get my orgasm and I was fully blue balled. The entire time we were there, I was rock hard and wanted to release. That's when another hand found its way into my lap. I looked under the table and Landon's hand grasped my cock and started to stroke me through my underwear. I was already close and before I knew it, I shot my load in my underwear. My eyes closed as my mouth opened and I moaned. Everyone stopped what they were doing to look at me and Landon. I could see the cheeky grins on everyone's face, except Ryan who looked annoyed. I couldn't handle him at the moment. I was in my post orgasmic bliss.

Brodie: Can we get back to business you two?

Henry/ Landon: Our bad.

Ryan: Hmph!

We got back to the discussion and the guys all agreed that something had to be done to save the school, so we took it upon ourselves to come up with a few events that would raise enough money. We came up with a community car wash and a pop up bar. We each took an event to oversee and plan. We had less than three weeks to plan, put together and have the events, so we couldn't waste any time.

~To be continued~