[FM] That time I [18F] gave a 6’7” football star [21M] my anal virginity

I don’t always make the healthiest decisions. Looking back at this one, I wish I could have freeze framed the moment of entry and done a voiceover a la *The Emperor’s New Groove*. “I bet you’re wondering how I ended up here, in a dirty frat house, with a cock slowly pushing its way into my ass for the first time.”

It’s a tale as old as time. High school girl goes to state college football game with her friends during her senior year of high school. Girl “accidentally” bumps into hot football player after the game at the nearby taco place that “just happens” to be where the team always goes after a win. Hot football player asks for girl’s number and then proceeds to booty call her every other weekend for months. Girl comes running every time.

Girl was obviously played by me in this remake, and hot football player was played by Josh. Josh was, simply put, an idiot. One of those guys who you can tell shouldn’t have passed the tenth grade, but his coach probably pulled some strings so that he could graduate and go to the nearby state school on a football scholarship. The redeeming qualities about Josh were his aforementioned hotness and his dick. While he couldn’t have told you more than three elements on the periodic table, he had fucked enough girls to get his dick game down to a science. He knew his way around a pussy like a lesbian gynecologist, and that was enough to keep 18 year old me running back to him again and again. The man was impossible to have a conversation with beyond “I’ll meet you in 10” and “oh my god don’t stop don’t stop don’t stop,” but I was absolutely addicted to his body.

Josh, in turn, was obsessed with my ass. Cupping it, smacking it, staring at it during sex. He pretty much only wanted to fuck in doggy style or reverse cowgirl. He was the first person I ever let touch my actual asshole, and that was only because he was so endearingly enthusiastic without actually pressuring me. The first time he rimmed me during sixty-nine, he came in my mouth in under a minute. The first time we incorporated anal fingering during vaginal sex, he barely lasted long enough to pull out, rip off the condom, and blow a load on my ass that covered both cheeks. The man was just obsessed. Although I was happy to go along with it to a point, and I found it incredibly flattering, I was too scared to let him anally penetrate me. It just wasn’t my thing, and I was terrified that we’d have an accident, and I’d have to shower in his dirty frat house. He also didn’t have the best track record for getting me off after he finished, so any time things ended quickly for him, I was left unsatisfied. I was not great at sticking up for myself with men in those days.

The night I finally let him deflower my anus, I was at home having a face mask, body-shaving, exfoliate-every-inch-of-my-skin type of girl’s night with my best friend and pseudo girlfriend, Jillian, while splitting a bottle of wine. I showed her the *u up?* text, and we laughed. “Well,” Jillian said slowly, “I did get an invitation to go hang out with Tom tonight.”

“Do you want to?”

She shrugged. “Tom’s cute. I heard he gives good head.”

“Are we really going to bail on girl’s night to fuck guys?” I asked, already knowing the answer.

We paused for a moment and then laughed, both of us nodding. “I’m too fucked up to drive,” I laughed, texting Josh back, “I’ll see if he can come get me.”

“Tom lives around the corner. Do you mind if I just head out?”

I shook my head and kissed her goodbye, waving her off. She knew how to sneak in and out of my house as well as she did her own by that point. To my dismay, Josh was also fucked up, and these were dark, pre-Uber days. Dressing in my sexiest non-sexy outfit so I would be covered enough to feel slightly safer traveling alone but still hot enough to turn him on the second he saw me, I hopped on the bus to campus. The things we do for dick.

After getting a little turned around and putting my keys between my fingers as I stumbled through the dark campus, I finally reached Josh’s frat house. The door was unlocked, and several of his frat brothers were hanging around playing beer pong. They waved at me. I waved back as I jogged up the stairs to Josh’s room. We were friendly enough, and they were decent guys, but their booze and companionship was not the reason I kept coming back to frat row.

I knocked on Josh’s door, and he called out for me to come in. His room was cleaner than I had ever seen it: no empty liquor bottles on display, no piles of laundry on the floor. He had even lit a candle. “Woah there,” I said softly, surprised and admittedly impressed.

The bar for impressing me was a lot lower in those days. As was the bar for treatment I was willing to accept from men. “What’s the occasion?” I asked, sitting down on his lap in his desk chair.

He kissed my neck as his hands wandered. “Just felt like it.”

“Bullshit.”

He laughed. “Ok. There’s a reason.”

“Are you trying to butter me up so I’ll let you try anal?”

He laughed into my neck and didn’t say anything. So that was a yes. I rolled my eyes and got up. “Josh, I’m not saying it’s never going to happen. I’m just nervous about it.”

“I did some research! I know to go slowly, and I got a ton of lube, and I can put down a towel. I promise I won’t be weird if anything happens.”

“You’re saying that because you haven’t had anything happen before. You’d freak out in the moment.”

“I never freak out. And I deal with gross stuff all the time. I’m always the vomit cleanup guy after parties.”

Somehow, that actually made me feel a little better about it. And I HAD just washed and shaved myself from tip to tail with Jillian’s help. If there was ever a time to try it… “Ok,” I said slowly, laughing as Josh pumped his fist in celebration, “but you have to stop the second I say to.”

He nodded vigorously and stood up, picking me up fireman style and tossing me onto the bed. I shrieked with delight and didn’t even have time to catch my breath before he eagerly pounced on me, his hands traveling across my body to frantically remove my clothing. In no time at all, I was naked and he was still fully clothed. I helped him pull his shirt over his head, but he flipped me over onto my stomach before I could touch his pants.

His tongue immediately dove into my ass, flicking against the rim and then pushing inside to fuck me enthusiastically. His hands spread my cheeks so that he could bury his face deeper, groaning against my ass. I arched my back and pushed against his tongue. Anal may not have been on the top of my to-do list, but Josh’s love of my ass flattered me to the point that I genuinely enjoyed myself whenever he played with it. After a few minutes of enthusiastic licking, Josh gently pulled me off his bed, laid down a towel, and tossed me back on. I giggled, watching as he finished undressing himself and placed a bottle of lube and a condom next to the towel.

He was breathless with anticipation, his cock harder than I had ever seen it. “Roll back over,” he demanded, smiling at me excitedly.

I got on my hands and knees, arching my back for him. He got behind me and played with my clit with one hand, his other hand pressing two fingers into my cunt and immediately locating my g-spot. Again — the man knew his way around a pussy. I moaned loudly and lowered myself to my elbows, giving him more access to my pussy and displaying my asshole for his enjoyment. He stopped fingering me, I heard the crinkle of a condom wrapper, and then his cock was pushing roughly into my cunt. He filled me to the brim, his cock pressing against my g-spot with every thrust. I moaned loudly, pushing my hips back to meet his thrusts. He dripped some lube onto my asshole and rubbed it in with his thumb, occasionally pushing in his thumb to lubricate the inside. He groaned softly as he worked, his pounding thrusts never faltering as he methodically, lovingly, fingered my ass. “Are you ready?” he asked breathlessly.

I was more than slightly disappointed to lose his incredible cock’s relentless pounding in my pussy, but I was admittedly getting excited to take this next step. Or, at least, I was excited because of how excited he was. “Yes,” I moaned, pressing my face into the bed.

He slowed his thrusts and then pulled out, dripping more lube onto the condom. I could hear him panting with excitement, and I reached my hands behind myself to spread my ass more for him. The tip of his cock kissed the rim of my ass. “Here we go,” Josh whispered, more to himself than to me.

He pushed inside me slowly, stopping when about half of his cock was docked in my ass. I groaned softly in discomfort, the unfamiliar sensation extremely unpleasant. Josh moaned loudly, and a look over my shoulder revealed that his head was tipped back in ecstasy, the look of pleasure on his face more intense than I had ever seen it. I felt my pussy gush, loving the fact that I could have this kind of effect on him. I bit my lip and turned back around to bury my face in the bed, breathing heavily in through my nose and out through my mouth, willing my body to relax. He suddenly pushed in the rest of the way, and I had to hold myself back from crying. “Stop! Stop stop,” I cried out once I was able to catch my breath.

He held steady. “Do you need me to pull out?” he asked, disappointment in every syllable.

“Just hold there,” I winced.

He kept his cock docked inside my ass, his heavy breathing and gentle rubbing of my cheeks revealing how much he loved it. After a tense few moments, or maybe minutes, the painful stretch was slowly replaced by a dull discomfort. I could probably handle this. His look of ecstasy floated to the front of my mind. I could definitely handle this if it gave him that look. “Ok,” I breathed, “you can move.”

His hands slowly trailed down my back to grip my waist, and he pulled out his cock with that same slowness. It felt weird. Not good, but not bad either. He left just the head of his cock inside me and then pushed all the way back in quickly. He groaned loudly, his hands tightening around my waist. “Fuck fuck fuuuuuck,” he whispered.

Despite the discomfort, I smiled to myself at his happiness. That’s how I was going to get through this, I told myself, I was going to focus on him and make him cum as hard and as quickly as possible. I got back on my hands and started pushing back against his thrusts. “Oh my god,” he groaned, gaining speed and intensity.

“Do you like fucking my ass, Josh?” I murmured, my ass meeting every single one of his rhythmic pumps as I pushed my hips back over and over again, jiggling my ass against him, “Do you like stretching out my tight asshole and knowing you’re the only man to ever be inside me?”

He groaned loudly and pounded me wildly, his rough thrusts becoming painful again. I powered through it, my pussy drenched from the sounds of his groans of pleasure. “Oh, god, I’m gonna cum,” he yelled, his hips slamming against my ass.

I bit down on my hand and held still, Josh’s groan-yells filling the air as he came into the condom, his thrusts not slowing down for a second as he fucked his way through his orgasm. At long last he stilled and stopped, his hands painfully gripping my ass and his groans of pleasure finally tapering off. He let out a couple whispered curses and smacked the side of my ass, slowly pulling his cock out and tossing the condom in the trash. He got off the bed and slipped on his pants before climbing back on, flopping on his side exhaustedly. I collapsed on the bed and rolled on my side to face him, my empty ass throbbing but full of pride. “How was that?” I asked, running a hand through his chest hair.

“It was fucking incredible,” he sighed happily, yawning, “thank you for coming over.”

I paused. It felt like he was kicking me out. “Are you… asking me to leave?”

He smiled at me apologetically. “I have an early training tomorrow. I don’t mean to be a dick.”

I was not someone at that age who felt comfortable demanding things from men. But at that moment, I saw red. “Are you fucking kidding me?” I hissed, grabbing his chin and forcing him to meet my eyes, “I just gave you my anal virginity out of the kindness of my heart. My ass is fucking throbbing with pain right now. The absolute least you can do is get me off or drive me home.”

He stayed silent, stunned by my sudden outburst. I continued, my anger rolling over me in waves as I thought about the number of times over the last several months I helped him finish without asking him to return the favor, and my asshole still fucking hurting. “I came over here, in the middle of the night, ON A BUS, and you want to kick me out without even TRYING to make me cum? I am a human fucking being, not a fleshlight, you absolute COCK.”

Josh blinked slowly, my words starting to sink in. “I’m sorry,” he said softly.

“You… are?” I asked, genuinely surprised that he wasn’t fighting back.

“Yeah. I thought we were using each other for sex.”

“We are! But I need you to treat me like a person at the same time.”

“So, like, going on dates and stuff?”

“Fuck no. Don’t you dare. Just giving a shit about whether I cum and offering to drive me home or helping pay for my gas once in a while.”

He nodded slowly. “I can do that.”

“Thank you.”

We sat in silence for a moment, my ass still aching with a dull throb. “So… are we cool?” he asked, his face worried.

I laughed at his expression. “Yeah, man, we’re cool.”

“Good. You’re scary when you’re mad.”

I giggled and threw an arm around him. “You tackle huge guys for a living, and you were scared of me?”

“I’m not naked when I tackle those guys.”

“Well, that’s a shame.”

He laughed. “You are one of the strangest people I’ve ever met.”

“Thank you.”

He pulled me towards him and kissed me gently, his tongue probing my mouth. He slowly ran a hand down my body and then brought it to circle my clit gently. His fingers worked me expertly, massaging my clit like only he and Jillian knew how. An orgasm immediately began to grow. I wrapped my arms around his neck and leaned into his kisses, moaning gently against his tongue. It took longer than usual because of the painful throbs from my still sore ass, but I eventually came hard against his fingers, pressing my face into his neck and moaning loudly. He peppered kisses across my face, searching for my lips. I turned and kissed him deeply, my heartbeat slowly returning to normal. After a moment, I pulled back and smiled at him, rubbing his cheek with my thumb. “Can you call me a cab?”

He nodded. “You don’t want to sleep over?”

“Fuck no,” I laughed, “I want to go home and ice my asshole. But I’ll take some cab fare too.”

He nodded and grabbed his wallet, handing me a twenty as we got dressed. I felt cheap for a fraction of a second, but then I remembered all the times I drove over in the middle of the night and paid for on-campus parking, including one $75 ticket for not moving my car in the morning, and the feeling went away. We finished dressing in silence, and he walked me to the curb, waiting with me for my cab. His friends all poured out of the house to head to a party, whooping and clapping him on the back as they left. I’m not sure what they heard, but it wasn’t like we ever tried to hide the reason I was there. I laughed to myself and waved goodbye at them facetiously, refusing to let them make me feel embarrassed. “So,” I said softly, turning to Josh as soon as they were gone.

“So. Should I, like, call you?” he asked.

I laughed and hugged him. “Please don’t. But text me the next time you want to mutually get off.”

The cab rolled up, and he kissed me chastely as he opened the door for me. “Get home safely,” he said softly.

I texted Jillian as soon as the cab pulled away from the frat house.

*anal virginity: gone*

>*omg so proud! how was it?*

*awful. I yelled at him. but he made it up to me. how was tom?*

>*fab. gonna keep fucking him til we graduate*

*lol enjoy!*

>*u need me to cum home tonight? ;)*

*if tom was so good then why do you need my attention?*

>*bc ur my main bitch*

*dont ever forget it <3 you should stay. enjoy the dick*

>*i always do <3 love ya lil*

*love you jill*

I paid the cab driver as he rolled to a stop in front of my house, and I sneaked in through the laundry room and up the stairs in the dark, holding onto the handrails to vault myself over the creaky top stair and the wooden plank with the slightly protruding nail. Slipping into my room without incident, I shut the door with a soft click. My phone buzzed repeatedly as I stripped and climbed into bed, placing a soft pillow under my throbbing ass. It was a dick pic and a series of texts from Josh.

>*hard again just thinking abt u*
>
>*ur scary as fuck but i like it*
>
>*now i actually want to go on a real date*
>
>*dinner tmrw? i can pick u up*

I laughed to myself and slapped a hand over my face, groaning. Apparently, the combination of my outburst and the tightness of my asshole suddenly elevated my status from casual hookup to relationship material. I had no interest in being a man’s girlfriend, but I wouldn’t mind bossing Josh around a bit more. I texted him back.

*one date. youre paying. and you better put out.*

>*i always do*

*and youre gonna make me cum twice before you even think abt touching my ass*

>*i can do that*

*fine. see you tmrw.*

A surge of power flowed through me. Maybe this could be fun.

Source: reddit.com/r/gonewildstories/comments/hcd9zj/fm_that_time_i_18f_gave_a_67_football_star_21m_my