[FM] A professional football player took my anal virginity and made me squirt

Charlie and I had been FWB for a few months the first time he tried to stick his dick up my ass. I let him try, and it felt like my asshole was ripping when he tried to push inside. I had not prepared at all, and the wetness from my pussy on his penis was not nearly enough for anal sex.

It ended almost as quickly as it began.

“Ahh! Fuck! Stop, it’s too painful.” I said.

And that was the end of it.

I googled how to make anal sex more comfortable shortly after that. I bought a plug (metallic, pink jewel) and started wearing it. I’d practice wearing it about 30 minutes per day, to dilate my anus, then take it out. Pretty soon, I started wearing it outside on short trips to the grocery store, or restaurants. I actually began to really enjoy the feeling of fullness it gave me. I found that an Epsom salt bath after always really helped.

Soon, I felt I was ready for a dick.

I texted Charlie.

“I’ve been thinking about something for a while.” I texted.

“What?” He responded.

“Ever since last time.”

“What about last time?”

“I’ve been practicing.”

“What are you talking about?”

I sent him a picture of myself bent over on my bed with a pink jeweled plug filling my butt.

“I think, I’m ready to give you my ass.” I typed.

We skipped dinner that night. I had cleaned myself down there (which is an experience), and didn’t want any unnecessary shit pushing through my intestines for my first time.

Charlie got us a hotel. It had been about a month since we last fucked.

I got him prepped with a killer blowjob (if I do say so myself) on my knees, then lubed the shit out of his dick and my asshole while I talked dirty to him, already completely naked.

“You’re thinking about fucking my ass, aren’t you?” I asked.

He nodded.

“You want to take this hard cock and shove it in my ass?”

He nodded.

“You want to take my anal virginity on all fours like this?” I asked, getting into position and lubing up my hole.

He moved toward me, dick pointed straight at my butt.

Looking at his cock, I was still nervous. More nervous than I let on. I had done better preparation this time of course, but his dick was much longer and thicker than my plug, so I was unsure.

When I felt his thumb against my asshole I gasped.

“Unh!”

“Oh yeah,” he moaned, rubbing it against my puckered hole, then stuck a finger inside. Slowly, my sphincter opened for it and accepted it as he began his preliminary exploration. I was squirming.

“Hold your ass still,” he commanded, inserting his finger in further and playing with it in my ass. The sensation was not unfamiliar from my own fingers. Then his knuckle slid in.

“Unh!” I moaned into the bed.

“Relax, baby,” he rubbed my back, “and pull your ass cheeks open.”

With my head buried, I reached behind me with both hands and spread my ass for him. I felt so exposed.

“Yeah, like that.” He said withdrawing his finger. 

Immediately, I felt something much larger pressing against my anus: his cock, which began to force itself past my sphincter.

“Ahh!”

“Just relax, baby.”

“Owww! Ow! Just saying ‘relax’ is not gonna make it happen.” I exclaimed. It hurt less than the first time we tried, but still really fucking hurt. But I gritted my teeth and pushed on.

“Just keep it still for a second.”

“It hurts. Oh my God.” I whined, with every millimeter of movement. “Ahh . . . Ohh . . . Oww!” 

“It’s in, baby.” Charlie tried soothing me. “It’s in, try reaching down and playing with your clit.”

I started rubbing my clit in compliance.

“Unh . . . Ahh . . . Easy . . . Ooohh,” The pain was starting to fade. “You feel really, um, *reallyyy* deep.” Deeper than the plug had ever been.

“You getting used to it?” Charlie asked, noticing my change in tone.

“Yeah.” I replied, then he pushed in deeper and it started all over again. “Ahh!” I yelped, but the pain faded quickly this time.

“Oh god. Oh yeah,” I muttered as I started to enjoy Charlie’s cock in my bum for the first time. 

Unbelievably, I soon felt his pelvis flush against my ass. He was all the way inside and moving less restrictively.

“Fuck, that’s a lot of cock, Charlie.” I whined as he started pulling out almost all the way and pushing in deep again.

“You’re no longer an anal virgin, babe,” he laughed, causing his dick to flex in my butt. “How does it feel?”

“Ooohhh! No kidding. It’s hard to explain.”

“Bad?”

“No, not bad. Just different. Oooohhh. Full”

Charlie rocked his cock back and forth into my tight ass.

“Fu-huh-huuuck,” I whined.

“You’re doing well, babe.” Charlie encouraged as he began fucking my ass a bit faster, and I used my fingers to rub my clit faster. It was starting to feel amazing.

“Oh, my Godddd,” I moaned, my eyes rolling into the back of my head.

“You like that?” Charlie inquired.

“Yesss!” I said.

His balls were slapping against my clit now as his hips repeatedly crashed into my ass.

“Take it, slut!” He ordered.

“Is that your new pet name for me?” I chided.

“Yeah,” Charlie laughed. “You’re my slut.” 

Charlie continued to sink deep into my anal canal, his balls slapping my clit.

“Oh fuck!” I cursed. He rocked his hips back and forth against my ass.

“How’s that dick feel in your tight ass, slut?”

I could tell by how he was moving and how he was speaking that he was close. So was I. I swallowed as he spread my ass cheeks apart, then answered.

“Oh shit, it feels so good, Charlie! Oh-my-god, oh-my-god-” I was feeling hot, really hot, like I was on fire. I could feel every inch of that man’s cock in my colon, my pussy was dripping, and my legs were shaking.

It hit me so suddenly.

“Oh my GODDDDDD!” I cried, convulsing. 

It was unlike any orgasm I had ever felt. My eyes rolled back as I squirted—yes, squirted—all over the hotel bedspread and screamed. It was so intense, transcendent even—a feeling of pure pleasure while my pussy fluttered and dripped in climax and my asshole stretched and clenched around Charlie’s girth. When I came to my senses, Charlie started fucking me again.

“I own you now. I own you.”

“Yes, you own me.” Still recovering from what might have been the best orgasm I have ever had.

“Your mine.”

“Mhm, I’m yours. All yours”

“Oh yeah.” Charlie groaned as I felt him push in deep.

“Unh. Fuck, you made me squirt.”

“Look at that smile. You liked it, huh?”

“Yes! I’ve never done that before.”

He was still fucking my asshole as he smacked my ass.

“Ahh!” I yelped. 

He reached around my back and started pinching and playing with my nipples, which only heightened the sensations. 

“Oh, my God!”

“Shit, babe. Your ass can really take it.” He smacked it again, making me yelp.

“Ahh!”

“I’m close.” He said.

My sphincter was starting to burn despite the copious amounts of lube as he thrust in and out of my butt.

“I’m not sure how much more I can take, Charlie. Unh! It’s so much dick.”

“You can take it,” he grunted, hands digging into my ass now as he fucked it, balls slapping my clit loudly.

“Fuck!” I cursed again.

“Take it, slut,” he said.

“Oh my god. Unh! It’s so fucking big.” I whined. It really was starting to burn, and I needed it to end.

“Fuck my ass, Charlie. Give me your cum,” I begged.

He kept thrusting, our moans growing louder. I sounded like a wounded animal.

“You really want it?”

“Yes! Pleasssseee!” I cried.

His hips stopped rocking and he groaned. I felt his cock jerk violently in my ass as it started to paint my insides with warm, thick semen. Over and over again, I felt him release more cum inside of my bum. 

“Fuck.” Charlie groaned, as I felt him withdraw. I swear my ass felt like it was trying to keep him in, but when he finally pulled out it felt like I was my butt stayed wide open, and a small amount of spunk leaked out onto the covers, though the majority stayed inside.

I was sore for a few days but in a good, sexy, secret kind of way. The ache reminded me of the stretching I took until I could get it again.

Source: reddit.com/r/gonewildstories/comments/xg8c1o/fm_a_professional_football_player_took_my_anal