Chapter Five: Prom Night
It was a picture-perfect SoCal Saturday—the time of year when most seniors were looking forward to prom or shopping for a new swimsuit for the summer. Like most of my peers, I’d already taken care of the prom dress situation. The swimsuit would have to wait because right now I was doing a very different kind of shopping with Jocelyn.
“These are cute?” I was holding up a box containing three princess plugs of different colors.
“Cute—but you definitely don’t want those!”
“No? Why?”
“Those aren’t safe. They really shouldn’t even be selling them,” Jocelyn explained. “See how the top is only as wide as the middle? You don’t want one of those getting lost up in there. And those could.”
“Oh!” I had not thought about that at all. “How embarrassing would that be?”
“Very. Also, rubber or glass is better. Look.” She picked up a set of rubber ones with t-shaped ends that had the added bonus of being far less expensive. “Also these have a nice taper, and you’ll be wearing them for a while at a time if you want to get ready. These’ll stay in even if you’re being pretty active, but they’re easy to take out too.”
So good to have expert advice. I had started out the second part of that year as a pretty normal senior and now I was in an adult store with Jocelyn shopping for anal plugs. Life comes at you fast sometimes.
We settled on the rubber ones she’d shown me, and I rummaged around in my purse trying to find the cash I’d withdrawn for this purchase. No way was I risking how this might pop up on my online bank statement. I wasn’t trying to have that conversation with my parents anytime between now and basically the end of the world. I found the cash and did my best to complete the transaction without making eye contact with the guy at the register. Jocelyn, as per usual, found my discomfort amusing and gave me ******* about it all the way back to her car.
I didn’t mind though. The truth was she was being a total lifesaver right now. I would have never been able to work up the courage to make this purchase by myself, for instance. I probably would have been in my room trying to shove vaguely phallic-shaped objects up my ass like an idiot instead if not for her. As crazy as it sounds, I needed someone to mentor me through all this, and she was doing a fantastic job. And she was kind of a pro after all.
“Ok, so I guess I don’t need to tell you to start with the small one?” Jocelyn said, laughing.
“No bitch. I figured that part out, thank you.”
“Don’t be a twat,” she told me with her trademark smirk. “So be gentle with yourself. Lots of lube obviously, and just wear it as long as you can when you’re not doing anything super athletic.”
“I can’t believe I am seriously considering wearing one of these to school.”
“It’s the best way. You can always go take it out.”
“I guess I can,” I said with a little sigh. What even was my life at this point?
~~~~~~~~~~
If you’re wondering about prom, yes I was going, and no Lincoln wasn’t taking me. I’m sure he had no interest in that and I wasn’t about to ask him. Abbey had this guy from UCLA she’d been hooking up with taking her, and I had agreed to go with a guy in our class that we’d both been friends with forever. He was really sweet but there had never been anything romantic between us, and I think he understood it was going to stay that way. And he really wanted to take me, so I agreed. So we did all the usual dinner, prom stuff, etc. I still have the pictures. Abbey and I are there with our dates, and we both look pretty great I feel like I can say, but all I can ever think about when I see those is that I was standing there with a plug in my ass the whole evening.
Because we were cool seniors, we didn’t stay at the actual prom very long. The four of us went to an after-party with some other people from our friend group. I, of course, had been told I had other plans for the rest of that night. I grabbed a ******* and talked to some people for a while, and after about half an hour, I texted Lincoln so he could come to get me. That took another thirty minutes or so, and I had a nice little buzz happening by the time he arrived. I grabbed my bag with my change of clothes and stuff in it, thanked my date and told him good night. Abbey came outside with me to say hi to Lincoln. And by hi I mean to flirt with him. They for sure still had their little unspoken thing going, and she was sarcastically telling him not to be too late getting me home.
“There’s plenty of room for you too, girl,” Lincoln told her. She rolled her eyes at him.
“Oh my god would you two just get a room,” I said, hopping in Lincoln’s SUV.
“Like I said, we got plenty of room, just ditch that white boy” he told Abbey with a cocky grin.
“Wish I could baby,” she flirted back. Lincoln and I were both shaking our heads as we drove away.
“Seriously I’m going to tell her to stop being a cock tease,” I said laughing.
“She’s fun. I can let it slide,” Lincoln replied.
“She just needs to get it out of her system. You should do her solid,” I suggested, only about half kidding. Those two really did need to get a room. Lincoln just laughed.
When we got to their place, James was on the couch watching something that looked like a Tom and Jerry cartoon of all things. Lincoln joined him, and I put my bag down, unzipped it to grab what I needed, and headed to the downstairs bath to change. I could hear them saying something about Delvin coming over and I hoped he’d bring Jocelyn with him. I wasn’t completely sure what tonight would bring, but I liked the idea of her being around for whatever it was.
As soon as I stepped out of the bathroom, now in shorts and a t-shirt, I realized I’d made a bad mistake. I still had the plug in me. It had been in so long I’d kind of forgotten about it. What the fuck was I supposed to do now? I should have turned around and walked back in of course, but I kind of froze for a second. They both looked up and kind of stared at me for a second.
“Well get over here,” Lincoln told me.
Too late now you dumb bitch. Appropriate there’s a fucking cartoon to watch because that’s about where you are right now. I walked over.
“Yeah—you can tell us about prom night,” James added. They were seated far enough apart that there was room for me between them, and it was clear that’s where I was expected to go. Lincoln eased his hand up my thigh as soon as I sat down and started kind of teasing at the edge of my panties (I had changed into loose running shorts).
“Did that white boy buy you a nice dinner?” James asked kind of nastily. I could sort of see where this was going but I was going to have to play along. I said yes, and started to tell them about it, but they both started laughing.
“I don’t want to hear all that,” Lincoln said. “Cool he paid for your dinner though. Nice how you ditched him to come over here and…” I didn’t get to hear what I’d come over here to do because he and James both erupted in excitement at a particularly sly series of antics Jerry was executing on TV. This went on for some time, and I have to say it was justified—Tom was getting wrecked. When that finally died down I was told get a fresh round of beers. I took their empties and came back with one for each of us. We watched the rest of the cartoon, Lincoln playing absently with pussy while they both continued to yell instructions at Tom, who was not taking them, as evidenced by Jerry’s continued elusiveness.
I went to get them more beers again when a commercial came on (my buzz was back by then) and when I returned and handed them over, James kind of stopped me from sitting down.
“I like a naked white bitch in my house,” he stated, kind of looking me up and down. I just stared at him like an idiot.
“You deaf? He’s talking to you,” Lincoln snapped. “Strip.” That snapped me out of my stupor. Oh *******, I thought, this is going to be bad. I pulled my shirt over my head and off.
“Hurry up—don’t be blockin’ the tv once the commercial ends. Tryn’ watch cartoons.” I heard James laugh as Lincoln said that. I slid my shorts and panties off together, tossed it all on my bag, and went to sit back down. I thought to myself, you absolute stupid slut you deserve what’s coming.
“Oh *******!” Lincoln exclaimed. “Look at this bitch!”
“Oh *******!” James echoed. I honestly don’t even remember what all they actually said after that. Hilarity ensued. I know I ended up over Lincoln’s knee like an unruly baby after a few seconds of that, an even more humiliating situation than what I’d been dreading. He spanked me hard a few times, still talking ******* about the plug with James.
“Why’d you put that up your ass girl?” Lincoln asked, clear amusement in his voice. I just kind of hung there, splayed over Lincoln’s knee, mortified and silent. James had put his hand under my chin, forsing me to look up at him. “Answer him girl,” James snapped, as Lincoln smacked my ass really hard again. So humiliating.
“I thought that…I thought that I needed it,” I stammered.
“You thought you needed it?” Lincoln was laughing again. “Why?”
“Because James…” I was still stammering like an idiot. “Because James said…” I started again.
“I did kinda hint we were gonna break that ass in when you sent her over here the other night,” James interjected. “She’s a proactive little slut,” he observed, letting go of my chin and giving my face a casual slap.
“Oh we’re gonna,” Lincoln said. “But let me get this ******* straight. You put that ******* up there when you got dressed for tonight. Let that white boy take you to dinner and prom with that shoved up your ass?”
“Yes,” I panted. He had two fingers in my very wet vagina now.
“So you sat and ate your nice dinner, then danced like that?”
“White girl dancing,” James editorialized.
“Y-yes,” I haltingly confirmed again.
“Because you knew once that white boy finished treating you like a little princess you were going to take my big cock up your ass tonight, right slut?”
“Yes, maybe,” I kind of whimpered. In the position I was in he was able to get his fingers deep inside me and as well as on my clit, and it felt amazing. The combination of that and the spanking, along with how degrading this whole situation was had most of my brain already basically shut off, as per usual. I was so wet I was probably making a mess, and I could hear James laughing still.
“Did you give that white boy even a kiss for all that?” Lincoln was just openly mocking me now.
“No. Yes.” I was basically just sort of mewling at him it this point. “On the cheek.”
“On the cheek!” Lincoln snarked. They both roared with laughter at that.
“Are you fucking serious?” James interjected rhetorically.
“So you gave that white boy a little peck on his cheek,” Now Lincoln was speaking to me like a teacher trying to get through to a particularly dense student. “And now here you are bent over my knee like a good little bitch.” He swatted my ass again pretty hard when I didn’t answer, and I finally managed to come up with another yes.
“What do you think you’re gonna kiss now bitch?” He disdainfully inquired. They both were really being kind of nasty about this and it was really turning me on.
“What—whatever you want,” I stammered. In the back of my mind, I was wondering for the thousandth time what was wrong with me, but I was too in the moment and too close to an orgasm to really care.
“That’s right bitch, whatever we want.” I could feel Lincoln slowly pulling the plug out of my ass, and sensed him tossing it in the direction of my bag. “Get off me, get on your knees,” he snapped, forsing me off the couch and onto the floor so I was basically kneeling in front of them both. I moaned as his fingers left my pussy. He took my chin in his hand like James had and slapped my face in any almost offhand way. “Nasty bitch.”
“Let’s give the little prom queen what she wants playa,” James told Lincoln, and they both laughed. Lincoln told him to go ahead, and I saw James start to unbuckle his pants. His big cock was already rock hard, and I didn’t need to be told what I was expected to be doing. I leaned forward and kind of swirled my tongue around the tip of it a few times then licked up and down some before slowly taking him into my throat. I was trying to get him as wet as I could, remembering how easily he’d gagged me before and what that had earned me. “This bitch,” I heard him mutter under his breath. I took that as encouragement and kept going.
“You don’t want some of this man?” I heard James asking Lincoln.
“Nah…go ahead. Imma break that ass in just a minute.” A little thrill of fear shot through me at that.
James reached down and grabbed me by the hair (messing up my nice prom updo I should note) and pulled me off his cock, forsing me to look up at him.
“Yeah and this dumb slut’s going to beg you for it,” he declared. “Because you want his cock in your tight little ass don’t you?” When I didn’t say anything he slapped me in the face again.
“Yes,” I whimpered. He slapped me again.
“Say it bitch.”
“Yes, I want his cock in my ass.” He slapped me again.
“Ask him nicely bitch.”
I tried to look over at Lincoln. “Please put your cock in my ass.”
“Yeah.” He ****** my head back down and I started sucking his dick again. It was soaked with my saliva now and I could see it running down onto his balls. As usual, I was desperate to please them regardless of how they were treating me. No one had ever raised a hand to me before in my life, and here I was getting wetter every time they slapped me. These guys didn’t give a single fuck about my privileged, cute, suburban-white-girl existence. They were talking about me like I was at best some dumb ******* that had wandered in and needed to be made useful. And the more degrading they were, the more turned on I got. I was pathetic.
“Good girl,” James told me. I smiled at him and went back to sucking his big cock. He let me do that for a few minutes longer, as I sensed Lincoln get up and then return.
“Ok gimme that bitch,” I heard Lincoln say. James took his cock out of my throat, and Lincoln pulled me to my feet by my hair. He herded me to the other side of the sofa and roughly ****** me over the arm in exactly the same place where James had fucked me before. I felt something cool and wet drip onto my ass and pussy. I could tell it was lube. I almost immediately felt his cock probing at my ass and took a deep breath, trying to relax. Then, I felt him ******* himself into me and I’m pretty sure I screamed.
“Please, please go slow, you’re too big,” I begged him.
“Take it bitch,” was all he said in response. Fuck it hurt so bad. Then there was this sensation I can only describe as a pop, and then he was all the way inside me. It still hurt after that but not as bad.
“Lincoln, please, please, please go slow,” I begged him again. He actually was going pretty slowly, giving me a chance to get used to what was happening. It still really hurt but there was also this strange undercurrent of pleasure. I was trying to relax my whole body as best I could, but it was hard to do. While he may have been going slow, he was far from gentle. I was crying and kind of panting, and I could fell mascara combined with tears running down my cheeks. I’m sure I was a mess.
“You asked for it bitch, now take it,” Lincoln snarled. Not strictly true, but I was hardly in a position to debate. He was going harder now that he kind of had a rhythm. I could vaguely feel him pouring more lube back there at one point, for which I was grateful. I was still crying because it hurt, but it also felt good, and the sounds from that Tom and Jerry cartoon were providing a bizarre soundtrack to everything. There was a weird combination of pleasure and pain colliding with each other, and I felt one of Lincoln’s hands playing with my pussy, adding to the former. The position I’d been ****** into also gave me a perfect view of the door, which I hazily noticed was opening.
Through my tears, I saw Jocelyn enter through it, accompanied by Delvin and some guy I’d never seen before. I could hear Lincoln and James yelling greetings at them, and somehow gathered that his name was Malcolm.
Jocelyn was, in the most literal sense of the phrase, wearing a dress. It covered just enough to not get her arrested. I observed this because Lincoln ****** my head up by my hair to look in that direction.
“Tell your friend where my dick is bitch,” he commanded. I hesitated, still kind of panting and crying, and he removed his other had from my pussy and slapped my face with it. “Tell her!”
“In-in my ass,” I stammered.
“Oh baby you’re doing so good!” Jocelyn squealed, and came and kneeled in front of me where my upper body and head were ****** onto the arm of the sofa. She was smiling at me, and gently brushed the hair escaping from now totally wrecked prom updo out of my eyes, kind of getting some of the steady stream of mascara stained tears along with it. The guy I didn’t know, Malcolm, came up behind her, lifted what little there was of her dress, and gave her ass a hard smack.
“Get that ******* off, bitch,” Malcolm demanded. She immediately obeyed, pulling her dress over her head and off, so she was just wearing her thong. Lincoln was still fucking me hard, and although it hurt less than it had, there was still a lot of pain mixed with the pleasure. To my great surprise, Jocelyn took my face in both her hands and kissed me on the cheek, then on the mouth. I was shocked at first, then gave into it. It was soft and sensual and she tasted like the wine she’d presumably been drinking. Her tongue was gentle in my mouth, different from any of the guys I’d kissed before. I heard the guys loudly and crudely expressing their approval of this development, but I didn’t care. I thought to myself that probably not many people lose their anal virginity and kiss a girl for the first time simultaneously. But like I said before, life comes at you fast sometimes. And what she was doing felt right.
Jocelyn broke the kiss and brushed my messed up hair out of my face again. The guys were still loudly carrying on—I’m sure the contrast of how sweet and sensual she was being with me and how brutally Lincoln was fucking me looked pretty erotic to them—it felt erotic to me despite the pain. I wasn’t sure how much more I could take though. He still wasn’t going very fast but it felt like he was super deep with every thrust, and the pain had not abated despite the undercurrent of pleasure. I was almost screaming with every hard thrust me ****** into me. Then, I got some relief from an unexpected source.
“Gimmie that bitch back,” James snapped. I felt Lincoln’s cock pulling out of me as James ****** me to my knees in front of the sofa. Jocelyn was beside me, and put her arm around my waist, kind of supporting me. I was grateful as I was kind of shaky after what Lincoln had just done to me, plus it felt good to be close to her.
“Yeah look at these two white bitches,” Malcolm said. He was standing in front of Jocelyn with his hard cock aimed at her face. She took it into her mouth without hesitation. James was in front of me and it was clear I was expected to follow suit. I licked slowly up and down his big cock a few times, getting him wet again, then, with a deep breath, carefully took him back into my throat. It must have felt good because I heard him groan a little. After maybe a few minutes of this, I felt Jocelyn guide me off James’ cock. She took my face with both hands again, and slowly, sexily kissed me. I didn’t hesitate at all this time—I was totally into it and eagerly returned the kiss. I could hear all for guys lewdly approving of what we were doing.
“Ok back on it you dumb whore,” Malcolm said, pulling Jocelyn away and back onto his cock. I turned back to James, licking his balls as I knew he liked. I worked my way back up to the head of his cock, and took him into my throat. Side by side on our knees, Jocelyn and I worked on pleasing our respective guys. I’m sure we must have been putting on quite the slutty display, and the guys were not shy about very explicitly expressing their approval.
“Ok my man, show’s over. Get her ass back up here,” I heard Lincoln say. I was ****** back up to my previous position on the sofa, and I felt Lincoln with the lube again, the same as the first time. I felt his cock teasing at my ass for a few seconds, then he slowly entered me again. It didn’t hurt as bad as the first time, but there was still that searing pain before he was all the way inside me. I’m pretty sure I screamed again. He fucked me for maybe a minute before I more sensed than saw James walk in front of me.
“I didn’t tell you to stop sucking bitch,” he said and pulled my head up by my hair. I was braced up against the arm of the sofa again, but my arms were free. I took his cock in my hand and kind of guided it into my mouth, mostly because I was afraid that if I didn’t he’d gag me with it again like he’d done the other night. Lincoln fucking my ass still hurt, but in that strange mix of pain and pleasure, the latter was starting to win out. I was incredibly turned on. They were using me like some kind of object, and even though I was still trying to figure out how to take them both like this, it felt amazing. It’s hard to describe how I felt in that moment. I had come to accept that being degraded and objectified was a huge turn on for me, and this felt like a next-level version of all those things.
I honestly don’t know how long them using me like this went on. I could kind of sense that Malcolm and Delvin were doing something similar to Jocelyn, and that they were being at least as rough about it judging from some of the sounds I could hear over the Tom and Jerry marathon on TV. Eventually, I felt Lincoln’s cock tense, and I knew he was about to cum.
“Take this ******* bitch,” he panted, and I felt the warm wetness of him cumming in me. He didn’t pull out right away though, and I felt his weight kind of leaning into me. James was still forsing his cock down my throat, and I was starting to have trouble taking him. I could already feel myself starting to gag a little. “Nasty bitch,” Lincoln called me again and finally pulled out with a final slap to my sore ass. I could feel cum dripping out of my ass, onto my pussy and down my leg.
Now that I only had one thing to concentrate on, I was able to get the blow job situation under control. With one hand around the base of James’ cock, I was able to guide how much of him was in my throat a little better and concentrate on really making him feel good. The slow, wet head I was giving him was clearly working because after only a few more minutes I felt his cock tense and he came hard. Most of it was in the back of my throat where I’d wanted it, and I was able to swallow as he was cumming, avoiding the embarrassing mess I’d made last time. He seemed to appreciate that I’d made progress because he told me what a good slut I was as I licked him clean.
That of course was not the last of the evening’s activities. I ended up with both of them in James’ bedroom for most of the rest of the night. James and Lincoln took turns with my ass and mouth, continuing to make ridicule me about my prom date in addition to the general name-calling they were both into the whole time they were using me. Finally, after James was satisfied, Lincoln and I went to his room. I collapsed onto his bed while he showered. He came out with his cock hard once again—dude was a machine—and finally fucked my aching pussy before we fell asleep. I felt like I’d officially been used in every way imaginable, and I’d be lying if I said I didn’t love it.
~~~~~~~~~~
So before I wind the tale of that summer down and send your beloved protagonist off to college, there’s one loose end I should tie up. I can do that by telling you about one early August night. Abbey and I had been at the beach that day and had then come back and done some shopping. Mostly looking at things, as it wasn’t like we really had money to spend. The two friends we had gone to the beach with had to be somewhere else, so we kind of stuck where the mall was. It was around nine PM on a Friday, and since we both kind of wanted to get high, I took a chance and sent Lincoln a text. He said he and James were on the way from somewhere, and they’d swing by.
I should add that I had finally told Abbey a lot more about my situation with them, even that I had been with both of them. I did leave out a lot of the rougher stuff still. Not because Abbey was a prude or anything—far from it—but I still wasn’t sure I could explain it in a way she’d understand. Anyway, she thought what I had told her was really hot, and I knew she still really wanted to fuck Lincoln, so both of them coming to get us seemed like a win-win no matter what happened.
They were in James’ car, which was a really nice convertible Lexus, the top down that night. Abbey greeted Lincoln with her usual exuberance, and his hand blatantly slipped down to her ass when she hugged him. She did not object. About time, I kind of thought. She needs to get this out of her system. Plus she was my best friend, and I liked seeing her have fun. Her eyes met mine and I gave her a kind of “it’s all good look” and a smile as I made sure to jump up front with James. She still had her arms around Lincoln’s neck, and she squealed and put her legs around his waist when he picked her up and carried her into the back seat.
We drove to a nice secluded little spot and parked with the music on low. We all chatted for a bit while we got high, enjoying the nice breezy night. Things progressed as you’d expect from there. Lincoln and Abbey had started making out, and shortly after that, I had James’ big cock in my mouth once again. I was on all fours, slowly taking him into my throat, and I could feel his hand on my ass, kind of absently squeezing as he enjoyed me taking care of him. From the sounds I could hear behind me, Abbey was doing the same—I’d heard some happy giggling at what I assumed was her first look at his super nice cock, and she hadn’t wasted much time after that. Soon I could hear some moaning from back there.
“You hear that?” James asked me. “Your friend gettin’ that ******* now.”
“Music to my ears,” I told him and went back to work on the blowjob I was still giving him. He laughed.
Before too much longer, I could hear the sound of Lincoln cumming in Abbey’s pussy and her delightedly urging him on. The sound of that must have really been hot to James too because seconds later he came really hard in my mouth. I actually struggled to swallow it all and had to lick what I’d missed off of his still hard cock. Shortly after, we pulled away, the wind feeling really nice as we drove through the summer night.
As we drove toward Abbey’s house (it was closer), I observed that she had discovered Lincoln’s remarkable resilience. She had gotten him hard again, and I could see her head happily bopping up and down on his cock as we drove. It was hot watching her with him. He had his head back with his eyes closed, clearly loving what she was doing. When we finally got to his house, she had to stop to go in. She smiled at me as she went in, and I gave her a wicked grin and a wave.
“Get back here and finish what your girl started,” Lincoln ordered me. I crawled into the backseat as we pulled away I got to work, my head replacing Abbey’s, bopping up and down on his gorgeous cock. No rest for the wicked, but that was how the summer had gone.
