Prom Night Anal [MF]

So, back on track, chronologically, everyone in the story is still over 18. Apologies for the delay in the story itself, but along with some crap at work, I was called in for jury duty, which is oddly enough worthy of another story entirely ;)

After the thrill of that after-concert romp, we realized it was a bit much to risk things like that in public, especially in school, so we cooled things off in public, but in the safety of our houses, when we were alone, we continued to fuck eachother’s brains out. Eventually, as time rolled on, prom was approaching. In the past I wouldn’t have really thought about it, wouldn’t have likely even gone, but things had changed a lot this year, and more importantly I actually had someone to go with. So one day after class, when we were at her place and both her parents were gone, I asked her.

“So, Prom is coming up, got any plans?”

“Not at the moment, why?” She asked back somewhat frustrated

“You wanna go together?” I asked

“If I say yes, will you go back to fucking me?” She replied, still a bit frustrated (In hindsight I think when I stopped to ask she was about to cum)

“One way to find out.” I said with a devilish grin

“Fine, asshole, I’ll go with you, now fuck me.”

I didn’t need to be told twice. I flipped her onto her back and started fucking her again missionary on the bed while sucking on her breasts. As I felt her close to cumming, I got close too, and when she started to she set me off as well. When I did start to cum I moved up and muffled her moans with my mouth, making out with her while we both came. While we were both backing in the afterglow of our mutual orgasms, she hit me hard in the shoulder.

“That’s for asking me that when you did.”

“Does that mean you changed your mind?’

“No” she said as she hit me again “and that’s for not asking me sooner.”

“Wait, what would have happened if I didn’t ask you?”

“I would have asked you, stupid. Besides, I’ve been saving something for that night.” She said as she got up and shook her ass in my face, and while I had certainly matured a lot over the year, I was still an idiot, and didn’t have a clue what she was talking about. She literally had to lean down to me, still on her bed, and whisper in my ear

“I’m gonna let you fuck me in the ass. That is, if you want to.” She said with that sexy little smirk on her face.

Over the last few months while fucking I had occasionally tried to slip a finger back there, always met with frustration on her end, and her hitting me. So her offering up her delicious ass like that was a very welcome surprise.

Fast forward a few weeks to prom itself. It wasn’t being held at the school, but in the city, so some friends and I all chipped in for a limo to get us and our dates there. I also got a nice room at a nearby hotel, and drove in myself earlier that day to check-in early and stock the room with some drinks so when we got there we could just head up. We decided to all initially go over to the date’s houses and have the limo pick us up there (small town, didn’t take long). When I got over to Emily’s house, her mom was teasing me about what we’d “really be up to” while Emily was still getting dressed, to the point where her husband was actually getting a bit annoyed too. He then gave me the stereotypical “dad speech” about how Emily was his little girl, and how he’d kill me if I ever hurt her, and it took considerable self control to not laugh because 1st, if he knew what we’d already done he’d try and kill me anyway, and 2nd, while definitely not the strongest person, I’m still 6’3’’, and he was only 5’8’’. Her mom was busy calming him down while Emily came out all dolled up. She was simply stunning in a navy blue dress that was just as beautiful as the girl wearing it. She came down, we took some pictures together, they sent them to my parents, and we hopped in the Limo when it got there. We were the first to get picked up, so while we were alone back there we were tempted to try something, but it wouldn’t be long before we got to the next house. Emily did have enough time to tell me to reach back to her ass and take a feel, only to find that she had a plug in, to “warm her up for the festivities after the festivities”. It was incredibly awkward hiding my boner when we got to my friend’s house next, but it had subsided by the time the last pair was picked up.

The dance itself was good, nice place, fun stuff to do, typical prom stuff. At one moment though that night, I thought I was gonna die, because I ran into Jack. He still hated me with a passion despite managing to get over Emily fairly quickly, and was here himself with one of the popular cheerleaders. I tried playing nice, but apparently asking him how his hand was was still a sore spot, but luckily Emily came up behind me and stopped him from doing anything stupid. She then went up to his date and told her she pitied her because she knew what the night had in store for her. “3 minutes of fun followed by a night of disappointment and anger because he couldn’t get his tiny dick hard again.” Before we walked away she whispered something in the date’s ear that caused her to look at me in disbelief. I asked her what she said and she told me “That you were more than 2x bigger than Jack, and can last 10x as long.” The rest of the night consisted of her teasing me and me trying not to step on anyone’s feet because I can’t dance for shit.

It was around midnight when it started to die down and our group decided to leave. My friends had other plans back in town to waste the hours away until morning, but Emily and I were the only ones staying in the city. When we got to the hotel they all wished us luck and one of them threw a box of condoms at us as they drove away.

“Should have told them to get bigger ones if they wanted us to use them” she said while trying not to laugh. I simply dropped them off at the front desk on our way to the room, earning a confused glance from the guy who was there. She couldn’t keep her hands off of me on the elevator ride up, grabbing my cock through my pants, telling me all the things we’re gonna do that night. We finally get to the room and reaches into my pocket under the guise of getting the room key, but really she’s just jacking me off in the hallway. I finally unlock the door and pull her inside, and she pins me up against it while pushing it shut. While pinned to the door, she gets down on her knees and undoes the zipper on my pants, finally letting my cock spring free from its confinement. Not even waiting to get my pants off she dives in like it’s her last meal. After all of the teasing throughout the night, I didn’t last that long up against the door. A few minutes into the best blowjob I’ve had (and still my top 5) I start to get the feeling that i’m about to cum, so I tell her, only to have her get even sloppier. When I came, she just kept on sucking until there was nothing left.

“Mmmmm, tasty.” Emily said while looking up at me. She then got up and strutted over to the bed, “Now, help me get out of this dress.” Wasting no time, I jumped over behind her and helped her out of her dress, revealing the beautiful lace lingerie underneath. I turned her around to admire it for a few seconds before bending her back over the bed and taking off her soaked panties, revealing the glistening lips underneath along with the jeweled bottom of her butt plug. I got down on my knees behind her and started eating her out from behind, holding her ass in place because she was already starting to squirm. What put her over the edge was when I started to twist and pull ever so slightly at her plug, causing her to bury her head into a pillow as she came all over my face. I didn’t give her long before I stood up and placed my cock at the opening of her pussy. Before plunging in, I asked her if she wanted the plug to stay in, she said “For now, ya, but before the sun comes up, your cock will be balls deep in there.” I bent over to kiss her on the lips before going as deep in her pussy as I could. She moaned into my mouth until I bottomed out in her, eliciting an excited yelp from her. I don’t know what came over me in that moment, but for some reason I wanted to be rough with her, and didn’t let up in my pummeling of her from behind. I even slapped her ass now and then, each time resulting in a loud moan from her, and her pussy clamping down on me like a vice. We switched from doggy to missionary to her on top, me never letting up on the intensity. I had lost track of how many orgasms I fucked her through, but eventually with her breasts in my face, I was finally approaching my 2nd of the night. I looked up at her, and brought her face down right in front of mine holding it there with one hand while the other was slamming her down on me, holding here there as I unloaded deep inside her, leading her to one final orgasm.

She rolled off of me exhausted and asked me “Where the hell did that come from?”

“I, I honestly have no idea.” I said back “Maybe I was thinking that if I was too big for your ass, I’d at least give you a night to remember”

“Well, Mission fucking accomplished.” She said, “Now get me something to drink, I need to rehydrate after that, and I’m pretty sure my legs won’t work if I try and stand up.”

It wasn’t until I hobbled over to the mini-fridge (my legs were a bit weak themselves, which Emily cracked up at) that I noticed just how soaked the sheets were. I almost felt sorry for the cleaning crew who’d have to clean the room the next day, but Emily quickly reminded me that not only would this not be the first time for them, but likely not the first time that day. I asked her how she knew that, and apparently some other couples from the dance were here too.

“Even so, I don’t think any of them are quite as “messy” as we can be” I told her.

“And you haven’t even gotten to the grand finale yet” she added.

We took a bit of a break to both rehydrate and recuperate a bit, until I could tell she was getting antsy. While I was ready, I still needed a bit of help getting hard again, so she crawled down in about 60 seconds of sucking I was ready to go. She then told me to get her purse for her, and got some lube out to use. She told me not to hold back and use a lot on her ass. After I slowly removed the plug, her ass was already starting to gape slightly as I poured the lube on, working some of it in with my fingers.

“Now, as much as I enjoyed you getting rough and dominant before, I’m gonna be in control for this, so get on the bed.” She ordered, and I complied.

She got up and hovered over my rock hard cock, pouring some more lube on it before moving any lower. Once she felt it was sufficiently lubricated she lowered down until the head of my cock was resting on her asshole, desperately trying to get in. It took a few tries to get it in, but once she relaxed enough to let it in, that sensation of finally slipping in was enough to cause her pussy to start leaking. She stayed there for a bit, getting used to the feeling, before she slowly started to go deeper. Each agonizingly slow movement deeper was almost unbearable in the pleasure it brought. I couldn’t tell you how long it took, it felt like an eternity, but it was a very long time before she finally looked down and realized that she was out of cock to sit on. She sat there with a devilish smile on her face while she relished in the feeling of being so full. When she started rocking back and forth, the sensation was enough that not only was she cumming, but I almost did too. She leaned down and we started making out while she brought her ass up and down on my cock. After a bit of this, I asked her if I could try something, and grabbed her ass and lifted her up almost completely off of my cock before simply letting go and dropping her back down on it. The sensation on that move along was enough that when she bottomed out again I could feel her squirt and get my stomach wet. She started doing this herself and each time she bottomed out I could feel myself get wetter and wetter. Eventually she slammed down and held it there as she came again, her ass tightening to the point I thought it had ripped my dick off.

She opened her eyes and looked at me, “That was probably the best orgasm I’ve ever had”

“Best orgasm you’ve ever had so far…” I replied, and grabbed ahold of her and flipped her over and moved her to the edge of the bed. I put her on her back with her legs up in the air and lined my cock back up with her ass. This time it didn’t take nearly as much effort for it to slip in and I not so slowly proceeded to bottom out, getting deeper than before with the change in position. I didn’t set the same pace as before while in her pussy, but I didn’t take it nearly as slow as she had while on top. I wish I could say I lasted as long as I had before, but even after cumming twice before, the sight of her crying out in pleasure underneath me combined with her tight, tight ass was just too much for me. It didn’t take long for me to tell her I was about to cum, and she just told me not to stop…so I didn’t. I kept fucking her ass and with one hand reached down and played with her clit, which brought her over the edge in a big way. She came all over me and herself, and I held myself deep in her ass as I came too. After all we had done, along with the long day beforehand, had finally caught up with us, as neither of us had the energy to carry on any further. I collapsed on the bed next to her, and she got up to clean herself up as best she could. The last thing I remember that night is her hobbling over to the bathroom before passing out.

I surprisingly woke up a few hours later as the sun was starting to come up, and found her snuggled against me, still naked. I didn’t have the heart to wake her up, so I just closed my eyes and went back to sleep remembering I had asked for a late checkout. When I came to the second time the sun was fully up and i could hear the shower running, so I surprised Emily by jumping in with her. We washed each other off for a bit, but when I tried to move things further, she said she was too sore from last night, which was fair enough. She did say that she wanted some breakfast, so I asked her what she wanted, offering to get out and order room service. She just hit me in the shoulder and told me “Not that kind of breakfast you idiot” and got down on her knees in the shower. The sight of her on her knees, with her blonde hair wetted back and her piercing blue eyes looking up at me was too much, and she didn’t have to work too long to get her breakfast. She swallowed and got out to let me finish up in there. By the time I got out she had put her dress on again, and it took every ounce of self control to not rip it off of her and spend the day in that room, but we also had to get going, our parents had called us multiple times apparently, and our late checkout time was approaching. We made it down just in time, and Emily ordered an Uber for us while I settled up with the front desk. On the ride back she leaned on my shoulder and fell asleep again, I couldn’t help but think that I didn’t want this to end.

Unfortunately, life never quite works out how we want it to.

Source: reddit.com/r/gonewildstories/comments/dixwm7/prom_night_anal_mf