In Over My Head Part 13 transgender/high school
I looked up in humiliation to see Jacob standing at the top of the ladder. I was so embarrassed, on all fours with my skirt up and Justin plugging me in the butt. I was sweating, and out of breath. Jacob was a little smaller than Justin, but was all muscle- probably from his army service. He was darkly tanned, and had very short, cropped blonde hair and hazel eyes. His hands were dirty from working on the tractor, and he had a smirk on his face.
"Mind if I watch, guys? This looks interesting..."
"This was, uh, kind of private here...." Justin stammed, freezing in his place. "If you don't mind..."
"Oh, c'mon," Jacob said smiling. "Don't mind me....I haven't seen any action in months. I won't get in the way....I just want to watch. Man, bro, you are really big! How does that thing fit inside her little hole!? C'mon, too late now to stop. Plus, if you don't, I might feel obligated to mention this to mom...." He smiled again, and his teeth looked beautiful.
"Sorry, Kylie," Justin whispered. "Is this ok?"
"Yeah," I choked. Just go really slow. I felt embarrased, but Jacob was so hot, that it was turning me on. He jumped up on a pile of hay and said,
"Let's get the show on the road, here."
I pushed back into Justin, and felt a twinge of pain as he pushed back. 'slow, remember, slow' I thought.
He buried his pole all the way, then started to pull out. It slid easier, now. Just as he reached the end, he pushed again and I let out another gasp.
I looked up and saw Jacob with his camo's pulled down, stroking and beautiful cock. It was a little smaller than Justin, but looked delicious. He noticed me looking, and smiled.
"Like it?" He said, playing with it so I could see, and spreading his legs.
I didn't answer, since Justin had just taken another plunge and almost knocked me down.
"Do you mind if I fuck in the front, while little brother digs into the back door?" Jacob said, while flipping his dick back and forth? "Double penetration?"
"No, she don't do that," Justin replied.
"Can I have some when you get done?" He asked, as though I wasn't even listening.
"That's up to her," Justin answered, pulling and shoving in rythem. I wandered if my hole would ever return to normal from this pounding. "She might suck it, if you act really nice."
Jacob jumped down, and stood a few feet in front of me, still playing with his tool. "So, do you want some?" He teased. "I need some relief, here....can you help me?"
I opened my mouth and licked my lips in response, and he stepped forward and placed his cockhead on my lips. It was dripping and slimy with pre-cum. I could smell a mixture of grease, dirt and male sweat, as I swallowed the head. It tasted good. He pushed, until I was taking it down into my throat. I could even feel the edge of his ball sack.
As I took more cock in my mouth, Justin increased his intensity. "I'm getting close," he moaned, gripping my butt.
"Here, switch places with me," Jacob said, pulling his rod out of my mouth. I felt Justin pull out, and a momentary feeling of emptiness as they traded places, and Jacob placed his dick in the entrance to my hole. He was smaller, so he slid in much easier than Justin had came out. I looked up to see Justin's cock in front of my face. I opened my mouth and he put it in. There was a musky smell from the fucking, but it wasn't bad. It was so big, I had to open my mouth wide. I knew he was getting close to a climax. In the meantime, Jacob was screwing me faster and harder than I thought that I could take, but it was feeling good.
Justin let out a loud grunt, and the first volley of spooge squirted into my mouth, followed by a rapid succession of huge spurts. I couldn't swallow it all, so it began to drool down my cheeks. He placed his hands on my shoulders and squeezed tightly as he continued to spasm. I licked the remaining cum off of his cock head as he started to soften.
"Be a good boy and go get the girl a towel from the house," Jacob ordered. "She'll need to clean up."
Justin nodded his head and said, "I'll be right back," as he went down the ladder. Now it was just me and Jacob, alone. His cock was still jammed inside of me, but he had eased up his thrusts.
"I think I know something that Justin hasn't figured out, yet," he taunted. "Girls don't have a prostate up their butthole, but I felt one inside of you. I don't think you are really a girl, are you?"
I froze, terrified. This army dude had his rod inside of me, and in a few minutes Justin- then the whole school- would know my secret. I stiffened.
"Hold on, I ain't gonna tell anyone," he chuckled. "You're not the first guy I fucked. In the army our choices can be pretty limited. I won't tell Justin or nobody. But you're gonna owe me, ya know!"
"O...ok," I stammered, relieved, but a little bit afraid, too. "Thank you."
"I tell you what, before Justin comes back, let your dick loose, and I'll stroke it until I cum. Deal?" He reached around and felt for my cock, and pulled it free. It was rock hard.
"Not a very big one, but it'll grow," he said, as he stroked and fucked me at the same time. This was the first time a guy had messed with my cock, and it felt really, really good. "Hurry, lil' brother'll be back in a minute, so we gotta finish this."
He increased his pace and the stroking as well, the shoved hard into me, "I'm gonna shoot, get ready, I'm about to plant some seed in you...."
I felt a jerking inside my rectum, and knew he was releasing a load as his body went tense. It felt so hot, that I began spraying my own load onto his hand as he jerked me. After a few minutes we both relaxed, and he pulled his cock out of my well stretched hole, and slapped my butt.
"Good job," he said, coming in front of me and holding out his cum covered hand in front of me. "Wanna share this?" he asked, then licked his hand and reached down to my face and planted a wet cum kiss on my lips. We heard Justin back on the ladder and he said,
"Remember, you owe me."
I was in over my head.