In Over My Head

By RE

Published on Apr 28, 2009

Highschool

In Over My Head Part 14 transgender/high school

I felt embarassed as I wiped my mouth and butt off with the towel that Justin bought me, while the guys looked on. I was wet with sweat, and when I stood, I was wobbly on my feet. Jacob took my shoulder and helped me up, and then down the ladder. I realized how sore my butt was!

They offered for me to stay and eat dinner, but I felt awkward and remembered that I was meeting up with Joel later in the evening. I would need a good shower when I got home. As I got in the truck, Jacob slipped me his cell number on a piece of paper and whispered,

"Remember, you owe me. Call me and we'll get together."

I felt like I needed a pillow to sit on in the truck, and several times Justin reached over and squeezed my knee.

"You were really good- thanks," he smiled. "A little kinky, but good. I don't know how you did it."

I felt a load sloshing inside me all the way home, and a need to get to a bathroom as soon as possible.

After a long hot shower, I checked my text message, and Joel had sent me a reminder that he was coming over after work. I had to make up my mind how much I wanted to tell him, or not. I was still undecided, so I thought I would wait and see what happened. I fixed a sandwich to add to Justin's spooge that was already in my stomach. I didn't have much time before I heard the doorbell, and went to let him in.

"Hey," I said, turning around for him to follow me. "You ate yet?"

"Yeah, I'm good. I could stand for something to drink, though."

"With or without alcohol?" I asked.

"You mean I get a choice? I don't usually ever drink alcohol. I've only had it once or twice," he answered.

"Well, a little won't hurt," I said, pulling out a wine bottle. "But since you're driving, you only get one glass. After that, it's a Pepsi."

I poured his glass, and we went to the family room and sat down.

"So, did work go ok?" I asked, making small talk. He was nervous.

"Yeah, same as usual. It's a job......you know that kid, Danny?" He was jumping right in.

"Yeah, I know who he is," I answered. "And you said Drew is his brother. I didn't know that before."

"You went out with Drew a couple of times, didn't you?"

"Yeah, a few times," I answered, cautiously.

"How was he?"

"What do you mean? He was ok, I guess. After a few times, it looked like it was going to go anywhere, though. He has senioritis," I answered.

"Anyway, he isn't everything he seems to be. That's one of the reasons I wanted to talk to you. Plus, I don't know if he said anything about me."

I was silent.

"His family was neighbors to our family, before we moved last year. I was around them all my life. Danny was a little younger, and Drew was a little older. We played, built a treehouse, rode bikes- that kind of thing that boys do."

"That's pretty normal stuff," I coaxed him along.

"Yeah.. But when we got in junior high school- Drew was starting high school about then, something happened. I was spending the weekend....I did that a lot.....no big deal. And I was with Danny and we started making stupid dares to each other. If you did the dare, then you could up the anty and make the other guy do something even worse. Like prank calls and things. Anyway, Danny, had really done a big dare- I dared him to get some whiskey out of his dad's cabinet and drink it, and he did. And he couldn't decide what my dare was to be, so Drew whispered in his ear and....." he went silent.

"You have me curious, now?" I said, smiling. "What could be so bad? Did you have to shoot someone, or put the cat in a microwave oven?"

He smiled, and lowered his head. "No, it was a sex thing. He dare me to put his....his dick in my mouth and suck it."

"That's no big deal," I said, trying to make him relax. "So you did it, didn't you?"

He looked surprised at my answer. "Yeah. I did. I sucked it, and then...."

"What?" I asked.

"Drew snapped a picture of it on his cell phone.....then, then he told me to finish Danny and do him, or he would send it around to everyone."

"What a jerk!" I said, meaning it. "So then what happened?"

"I went on with Danny and he...kind of got finished...with Drew watching and acting like a coach or something....then Drew put his in my mouth and I sucked it, too."

"And that was alll?" I asked. "Not the easiest thing, but then it was over, wasn't it?"

He paused, shifted in his seat, and hesitated before saying. "With Danny it was. It was only once. But Drew kept reminding me of the picture when Danny wasn't around, and making me do it over and over again."

"How many times did it happen?" I asked.

"Every couple of days. There were places that we met outside, or at his house. Sometimes at my house. It wasn't unusual for us to be in our bedroom's together, and my parents didn't notice. It happened until we moved."

"But that was for at least two years, wasn't it?" I asked, adding up the dates.

"Yeah.....but that isn' what's the worst......what's worst is....I didn't ever tell anybody this...ever. I acted like Drew was forcing me, but really, I liked it and put myself in places where I knew that he would be by himself. I played him more than he played me. A few times he even spent the night, and slept up against me and humped me during the night. He would whisper, 'pretend your my girlfriend,' and he would do that until he had a climax- right onto my bed."

I didn't know how to respond to any of this, and we both sat in silence for a while.

"Do you think I'm gross?" he asked.

"No...NO!" I answered. "Not at all. Has there been other guys?"

"Huh uh, just Drew. But I have looked at guys in the showers and all.. I haven't really looked at girls...you know, in a romatic way....just as friends...until now."

"What do you mean now?" I asked. "Who are you looking at now?"

He blushed. "You."

"Me?" I answered, but suspecting it anyway.

"Yeah, but it's weird. Sometimes I have even looked at you....you might get mad about this....and imagined what you would look like as a boy...."

My moment of truth was getting really close. But if I revealed myself, there would be no going back. This could change everything.

"Have you wanted to kiss me?" I asked.

"Yeah.... I guess so."

"If I was a boy, would you kiss me?"

"Drew did kiss me a few times, but I think he was pretending that I was a girl he was fantasizing about when he did. Yes, I would kiss you whether you were a boy or a girl, I guess."

I was in over my head.


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