wrestling-with-my-thoughts
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Wrestling with My Thoughts

Wrestling with My Thoughts

by Hentyty66
10 min read
4.5 (12700 views)
first time gayfemboyreluctanceassfriends
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"Hey, Riley!" my jock friend Nick shouted behind me. I turned to face him and brushed my long strawberry blonde hair out of the way of my eyes. "We need to practice a couple new moves for college season! Can I come over tonight?" I smiled and shook my head at his first statement.

"Sure man." He started walking with me to my house from school. We were both 18 and Nick even had a part time job saving up to work on a car that his dad wanted him to have. He was a handsome white tall dude that a certain type of girls went for. Jawline with stubble, short messy brown hair, hazel eyes that glowed like honey. I will never understand how he didn't drown in the pussy. Unlike him, I was demure, skinny but toned with a fat ass and thighs from my time as a wrestler and soccer player. My fair skin with freckled face and pale green eyes rendered me feminine.

"I can't believe wrestling ended like that. I lost state due to a technicality." Nick said saddened. His shoulders still confident with his stride, I really did admire my friend. We met when he joined a wrestling for tikes program and I beat him for the first time. He vowed he wouldn't let me win so easily next time. And throughout the years he's gotten better than me but only due to his weight gain and height on me. I still had some skill over him though. My legs were deadly if they got around you.

"I know you'll be able to do something in college. you're too good in your class." I tried perking him up. He flashed a grin and kept his head high. "If only I could do good in the female department."

"You're such a good friend, Riley. One day a girl will love to be loved by you." He stated smiling. I blushed for a second but couldn't take the hope.

"Sure i am dude. So what do you wanna do tonight?" I dismissed.

"Well i'm not hungry per say. I'm gonna fuck you up at a match real quick though." He promised. I chuckled. "You'll see. I got a strat that is bound to work on you."

We got to my house and my mom texted me seeing us on the doorbell cam that she wasn't gonna be home til late tonight. Between Realty, two secretary jobs, and her many side hobbies she barely had time for me let alone herself. Yet, she had many suitors that were in and out of our life. "Just us tonight, dude."

"Well I need to warm up so we can wrestle. I need to get one out of me." He dropped his backpack and started undressing in my living room. Down to his boxer briefs that clung to his body showing off his package that caught my attention. "Bro you good?" Startling me.

"Yeah, um, just zoned out for a minute." I shook out of myself. I told him I had to change too but as I went to take my basketball type shorts off I realized, I forgot I was crossdressing today. I put on a pair of my moms black cotton lacy hipster panties.

Now I've been crossdressing subtly for about 5 years now. Just little things like my moms nighties, bras, panties, stockings. It made me feel sexy. Especially with my fat ass. I had a whole secret account on snapchat dedicated to the pics I would take of myself. And today of all days I was in crossdressing femboy mode. I started to walk to my room nonchalantly until he stopped me by grabbing my arm.

"Where do you think you're going punk?" Nick joked like clint eastwood.

"I gotta go change into something more comfy." I said but he didn't care as he swept for my legs and tried getting me on the ground. I giggled fearfully as i dodged.

"Oh no ya dont. You are mine now boy." He proclaimed in a southern accent. He kept trying to go for my legs which made it easy to dodge his advances but I knew i could only do this for so long. So I jumped up and hooked my leg around his neck before flipping over and arm barring him. He was caught off guard to say the least. He struggled as I squeezed, his free hand clawing at the bottom of my shorts. Thankfully he tapped before my secret was revealed.

"Jesus dude where the hell did that come from?" Nick said exasperated.

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"I still got some tricks up my sleeve." I chortled as I got up realizing my shorts were low I quickly pulled them up before he noticed.

"Alright round two." He said diving for my legs again and this time I was caught off guard and he had me on my back. I squirmed upwards while pushing down with my legs causing my shorts to slide off my waist. I couldn't seem to get out of this position but my shorts were down to my knees already. Fear in my heart arose to my throat as Nick grabbed at them and pulled them off me smoothly. He didn't seem to care or notice that I was in panties but thats all I could focus on. "HA! I got you right where I want you, dude!" He claimed as he pushed my legs up to my head (thank god i am flexible). With that he pressed his now hard groin against my ass. HE was HARD. I wiggled my ass back and forth a bit til I was in a position that his tip was pushing against my hole. Certainly not on purpose. I'm not gay. I was trying desperately to get out of the position. But I couldn't escape.

"aaahhh" I moaned as his fat mushroom tipped dick was trying to enter me. I was drooling a bit too i guess. I stared up into Nicks eyes in shock and excitement. Ain't no way this dude was starstruck on me. But i swear i saw a glint of pleasure in Nick's eyes. He pushed with his crotch as his dick tried spearing me. I couldn't help but moan again. "aahhh oohhh dude ugh what are you uh doing?" He blinked himself out of the trance he was in and I saw my opportunity. I threw his hands off my inner thighs and rolled my body to get on my knees and crawl away from him. Which looking back was not the best idea. I got maybe a foot away before Nick's left hand gripped my love handle and his right forced my face downward. "oooff" I was once again in a predicament.

"Why are you wearing these type of underwear?" Nick asked shocking me out of my body. I instinctively pouted and turned around to look at him just as I heard a snap from an elastic band. "Oh fuck dude. You gotta do me a favor."

"What?" I questioned my breathing quickened. His hands were off of me and on my underwear fumbling a bit before Ripping the back of the panties open. "What are you doing Nick?" I started faux moving again acting like i was going anywhere. His strong hands gripped my hips as he lined up his cock with my asshole. "Ay man i'm not gay! what are you-" He pressed his dick hard against me but the head slipped. I was panting like a bitch in heat now. I reached behind me and grabbed his dick to line it up to my hole for him and kept it steady there til he shoved his meat in. "AAAAHHH FUCK!" I gasped as his head popped inside my entrance. Searing pain resonated thru my body. Which must've been the opposite for him.

"Riley, your ass is so tight. It's better than any girl's pussy." He groaned. Which did something to me. Something inside me snapped, I suddenly liked that i was giving Nick pleasure. I wanted to do more. He slowly slid his huge cock inside me til his hips kissed my cheeks. "Dude I can't believe i'm finally doing this."

"UGHHHH Uh Doing this?" I asked between grunts. "You wanted to do this?"

"Are you kidding me? Half the school wants to fuck this ass, Riley. But you're my best friend and now i'm getting it all to myself." He claimed. "Thank you so much."

"AHH holy fuck WAIT OH GOD Your DIck." I couldn't seem to function with my wording. "Your cock is so fuckin big. I'm not gay"

"I'm not gay either bro. But here we are. Me inside YOUR ass." He clarified.

"I'm gonna fuck you so good. You'll fall in love with me." He promised as he started to pull out til his tip was the only thing inside. Then he slammed his whole 8" cock back inside my awaiting guts.

"AAAHHHHHHHHHH FFFFFFFFFFUUUUUUCCKKKK yesssssssss"

"YEah TaKe this DICK BITCH!" Nick shouted as he spanked me. I liked that.

"YES DADDY"

"MMM YEAAHH you're my bitch now. Nobody elses. YOU. GOT. THAT. BITCH?" He said as he pounded my fat ass. I grinded against him and that made him groan in the deepest voice i've ever heard. I was making my friend a real man. And he was making me his real woman.

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"I'm gonna cum!"

This made him come alive again as he pressed against my left hip and rolled me back over on my back. He started pile driving my asshole as my legs wrapped around him. This was by far the best feeling ever. What made it even better was Nick leaning down and staring me in my eyes with full desire. I couldn't take it anymore and I kissed him as I came from my dick. "Im cumming inside Riley!"

"YESssSsssssss!! fuck me get me pregnant!" I shouted. As Nick's hot cum pumped inside me I panted and reveled in ecstasy. After several minutes of catching our breath. Nick leaned down to kiss me again.

"Thank you for being my friend, Riley. I uh I dont know what to do from here. Are we still friends?" Nick's post nut clarity was kicking in. I smiled at his nervousness.

"Your dick is inside of me. Just like your seed. I think we're a bit more than friends. I think we're-" I started.

"Please, wait. I dont know." Nick interrupted. His cock twitched inside me.

"I think we're gay." I finished as I adjusted and tried to pull away from him. But his hands reconnected to my skin below my ribs holding me in place. I looked into his eyes. "Nick, what are you doing?"

"Riley. Please don't tell anybody about this. I can't be gay. I'm going to college and I dont want guys to get the wrong idea." He explained.

"Oh, you think I want people to know i just got fucked by your big dick?" I said irritated.

"No, wait. I mean I wanted to fuck you. I have since we were young but I don't want to be fucked. Like I only want to fuck you, if you wanted, if that makes sense." Nicks explanation finally did somewhat make sense to me.

"So, you want to like friends with benefits with me?" I asked for clarification.

"Kinda. I promise not to fuck anybody else other than you though." He added.

"Okay, same. But uh...Are you going to do that again here soon?" I asked as his big dick once again became hard as a rock. I rotated my hips against his pelvis.

"If you're down, baby." Nick smiled before coming in close for another kiss.

"AH fuck your cock is so big. Yeah. I'll be your girlfriend by the way." I added with a smirk.

"YEsssssss Fuck you're the best." Nick groaned. We fucked two more times before we ended up sleeping together. Tomorrow is gonna be crazy.

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