Tomorrow's Problem

Quick heads up, this story has gone through many revisions and at one point was going to be in two chapters with a time break in the middle. I decided I wanted to publish it as a single work, so I added a transition of about a thousand words in the middle. The transition is more 'tell' than 'show', but please push through as I really like the second (or third) part of the story.

All standard caveats apply; 18, happy ending, etc., etc.... Enjoy, and please leave a comment when you finish reading.

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I'd heard horror stories about these things. Parties where cute girls bring dorks and nerds and embarrass the hell out of them, but I'd never thought I'd fall prey to such a thing. I mean, I'm in great shape. Sure, I'm majoring in technology management, but I'm getting an MBA to go with it, and I don't have problems with the ladies. At just under 5 - 8 and 135 pounds, I'm lean, but I've got a great sense of humor. Hell, I haven't had a dry spell longer than a few weeks since I was a freshman in high school.

Sure, April Weathers was a little out of my league. We saw each other at some of the same parties, and it wasn't like I was a total loser or anything. When she asked me to go to the Halloween dress up party at her sorority, I jumped at the chance. I didn't even balk when she suggested I go as her twin, wearing one of her cheer uniforms. It would be a tight fit, but I saw her point. I had long golden red hair just like she did and was only an inch or two taller than her. In a weird sort of way, it sounded like a lot of fun.

She went all out, having me get rid of all my body hair, and I mean all. The uniform had a bare midriff and was sleeveless, so any traces would give it away. She even bought me boobs the same size as hers that she glued on so I could do a couple of simple cheers she taught me without them bouncing out of my bra. Yes, she had me in a bra and panties, too. She even did my nails in school colors, just like the cheerleaders wore on game days. Like I said, she went all out. When she finished my makeup and let me look at myself in the mirror, I could have been her twin.

"OK, you look amazing. Now I need to go get ready. You know where the house is, right?" I nodded. "Just be there at nine. And don't be late." I got a quick kiss, and she bounced out the door. "It's going to be awesome." She laughed over her shoulder.

My roommate thought I was crazy until he saw me all dressed up.

The party was in full force when I got there. I figured out exactly what was going on when the girl that met me at the door escorted me into a room of guys dressed just like me. I was the only one that even came close to passing. It took about three seconds to realize I was also the only one with a clue about what was going on.

When I heard someone in another room trying to get everyone to quiet down, I knew I had two options: find another exit or go out and suffer being humiliated.

I'd like to say I did the honorable thing and warned the other guys, but I was quickly diving into survival mode. The only skin I cared about was mine. Slipping out of the room into a hallway, I made my way toward where I thought I'd find a back exit ending up in a room with three large men and a pool table.

"You lost? I think the party is that way." He pointed back the way I came.

"Not lost, just looking for an exit that doesn't get me humiliated. Once I realized what was really going on, I bailed. I'm not falling for this shit. Now if you'll excuse me." I tried to make my way past them. Two pool cues blocked my way. The third guy came up behind me.

"You dressed like this, and you don't think you're a loser like them other guys?"

"Do you guys know April? I'll bet she could talk all three of you into a dress without breaking a sweat if she gave you a hope you'd get into her panties. Am I right?"

"Nah, man. It ain't that hard. You just got to have what she wants." He grabbed his crotch and let out a raucous laugh. "And you dressed like her, you even look like her, so maybe you like the same things." The guy behind me pressed down on my shoulders. I wrenched free and turned to face him. Hell, he was almost a foot taller than me and probably bench-pressed Volkswagens for fun.

"Way I see it, you got two ways out of this room. Back the way you came, or through us. There's only one way you're getting through us." He fucking undid his pants and pulled out the biggest cock I had ever seen. "And to be honest, you ain't going back the way you came. Your only choice you get is whether you make this hard or easy." They all laughed.

"Not happening." I leered at him.

"We could make you. Like I said, hard or easy."

Each one of these guys made two of me. If they ganged up on me, there was no way I could stop them.

"Tell you what, I'll play you for it." I motioned to the pool table. "You win. We do this your way. I win, I go on my merry way."

"Deal." He grinned at me. "I'll even let you break."

It wasn't even pretty. He sank ball after ball after I broke. I was so fucked until he lined up his shot on the eight ball and scratched. I was off the hook. Putting my cue back on the rack, I headed toward the door.

"There's three of us." I closed my eyes, took a deep breath, and grabbed the stick.

The second guy wasn't as good as they first, and we both had a few tries at the eight ball before I finally made my shot. Something told me he wasn't trying as hard as his friend, but I wasn't about to complain.

Guy three looked at me like I was a prime piece of meat. I got lucky and sank a ball on the break, taking three more off the table before I missed. All I accomplished was getting them out of his way. He ran the table, looked at me, and licked his lips.

"I think you owe me something." Shit, his cock was bigger than the first guy.

"You're really going to make me do this?"

"You made the bet." He grinned at me. "We'd probably have let you go after messing with you a bit, but..." He fucking laughed at me, "you made the bet."

"All right, let's get this over with. I can't believe I'm fucking doing this." I dropped to my knees.

Having one myself, I knew all about cocks. Where the sensitive places were, what felt good, what didn't, and what I liked girls to do to me when they gave me blow jobs. The hard part was going to be getting over my revulsion of touching another guy, especially his dick, and in such an intimate manner.

It was surreal the way the pale white fingers with the blue and orange polish looked as they wrapped around the ebony shaft. They didn't even look like they were mine.

"You made the bet." He smiled at me one more time as I looked up at him pleadingly. "Just take your time. Who knows, you might even like it once you get started. Girls like you usually do."

Girls like me. What the fuck?

I closed my eyes and reached out with my tongue, just licking the tip.

"That's right. That's a good girl." He put his hand on my head and ran his fingers through my hair. "Now kiss it." I did what he asked.

"Open." He whispered. Once more, I followed his instructions as he slipped the head of his cock into my mouth. Fuck, I was sucking a cock.

I did everything I could to not think about what I was doing, instead focusing on what I knew I liked girls to do to me.

The musky odor wasn't that bad. In fact, it was slightly intoxicating, and the feeling of his soft skin on my tongue as I ran it over the bottom of his shaft was almost pleasant. Taking my time, I pushed my revulsion down inside me and focused on his responses.

"Yeah, baby, just like that." "So good." "Oh fuck..."

His moans grew louder. I tasted his sweet pre-cum as it seeped into my mouth. Something changed, and I found myself trying to make his moans louder, his comments more emphatic, more frequent.

"Yeah, baby. Just like that. You are so good at this." I took him deeper into my mouth, stroking him with my hand, squeezing as he hit my gag reflex, gurgling, and coughing as my throat protested.

"You want it all, don't you?" I couldn't answer, but knew he was right. Something inside me was changing. Maybe it was the challenge. Maybe it was something deeper. I opened my eyes and looked up at the massive mountain of masculinity standing over me. When our eyes met and he smiled, placing his hands gently on the sides of my head. I understood. The why ceased to matter. I wanted all of him. I licked, I sucked, I played with his balls, all while doing everything I could to take him deeper and deeper into my mouth.

When it finally happened, it surprised me as much as it did him. His grip on the sides of my head grew firm as he held me there until I started gagging. That was when he took over, leaving me helpless to protest. Tears streamed down my cheeks and I fought for air as he shoved his cock into my throat over and over.

"You ready, baby girl?" I don't know why he even asked. There was no way I could answer. He shoved his cock as far down my throat as he could. I felt him tense and then pulse as he unloaded his seed into my stomach, slowly pulling out and squeezing the last few drops onto my tongue. I rocked back on my heels, looking up into his deep brown eyes.

"That wasn't so bad, was it?" He offered me his hand and helped me to my feet. "In fact, I think once you got started, you liked it." I couldn't even look at him. We both knew the truth.

"You're all right. Why don't you hang with us for a while?" One of the other guys handed me a shot of something. I didn't even think about it. I just downed it and coughed. There was a fridge full of beer and a bar full of liquor. We played pool and laughed and joked, but the amount of alcohol I drank seriously impeded any chance of me remembering. The last thing I remembered was thinking I didn't even know their names. I may have given the other two guys blow jobs, too, maybe more than once,

I woke up in a strange bed with someone's arm wrapped around me, holding me close. Being the little spoon for a change was nice. I felt safe. I let out a sigh and just lay there, listening to the deep breaths behind me and enjoying the warmth of whoever's bed I was in.

"You awake?" I felt him move behind me and turned to look up into his face. It was guy two. The look in his big brown eyes made me giddy. "I'm Derrick. You passed out, so I brought you here. I'm sorry if things got out of hand last night."

Memories of what I had done slowly filled my head. After the first time, I never objected or fought back. I liked everything I did. "It's ok. I made the bet, and I always pay my debts." I blushed. "So why here?"

"Because you're the prettiest girl I've ever seen, even if you're not quite all-girl. I just wanted to make sure you were safe, and I knew I could protect you if you were here with me. Fucking Tyrel wanted to pass you around a little with some of the other guys, but I shut that shit down fast."

"Thanks. I guess I had a bit too much to drink."

"And other things." He smiled at me. "How much do you remember?"

"Not as much as I'd like. I remember playing pool and doing shots, and I think I gave a few more blow jobs."

"Yeah, you really got into it after a while. It was actually impressive."

"You let me win. When we played pool the first time, you let me win?"

"Yeah. I was hoping Tyrel would follow my lead, and then you acted like you liked it, so."

"How many?"

"Six. I think you did each of us twice. We all got kind of tight and I lost count. Like I said, you acted like you liked it."

"I guess I did. This is kind of nice, too." I nestled against him and laughed. "I am so fucking confused."

"Just relax. I'll take care of you."

"I'm not sure if that scares me or excites me."

"What about it scares you?" He leaned down and kissed me softly.

"Besides that?" I let out a soft moan as our lips parted. "I think what might come next?"

"Is that what you want?"

"Derrick, I don't have a clue what I want. Before last night, I'd never have thought I'd want to suck a cock, much less six times, and yet, here we are. If you'd asked me yesterday, I'd have told you there was no way I'd sleep with another guy, especially cuddling with him. And then letting him kiss me like you just did, no way. But, again, here we are."

We just stared at each other. His deep brown eyes wrapping me in a strange warmth I'd never felt before. Fucking asshole kissed me again. This time, I wrapped my arms around his neck and pulled his lips to mine as hard as I could, letting his tongue invade my mouth. I could feel his erection pressing into my thigh. Holy shit, what had I gotten myself in to?

We made out, kissing each other and letting our hands explore our naked bodies. I hadn't even thought about being naked. Maybe his intentions behind bringing me here weren't completely pure. I could hear myself moaning, my body tingling, as his massive hands gently caressed my skin. He even played with my fake boobs. The longer we kissed, the more we played and touched each other, the more lost I felt. I was so fucking horny; I couldn't stand it.

"What do you want?" My voice was almost a whisper.

He took his cock in his hand and pressed the tip into my ass.

There was no more discussion. My body betrayed me again. Derrick pressed his cock into my ass one more time. I bit my lip, nodded, and pushed my ass back into his invader. Tears welled in my eyes. Consciously, I didn't want this, but I couldn't say no. Somewhere deep inside me; something knew it was the next step in the progression, craved what I knew was going to happen. Every part of me understood. I couldn't, no, wouldn't stop it.

He reached over to the small table next to his bed, grabbing a bottle of lube. He showed it to me. Cringing, I nodded again. He slipped back between my legs, and I pulled my knees to my shoulders. Derrick lowered his lips to mine, kissing me softly before he covered his fingers in the slick liquid, using them; one, two, then three to prepare me for what was to come.

Trembling with a mix of fear and anticipation, I closed my eyes and tried not to cry. I was letting a guy I'd just met fuck me. Where did this even come from? Why had I made that stupid bet last night, and why had I stayed after I'd paid it? Fuck, I'd sucked all three of them twice?

It took him some time to work his cock inside me. He stopped when I protested, taking it out a time or two when I winced in pain. He'd give me a concerned look, like he was asking me if I wanted him to continue. I'd shake my head yes. Finally, he filled me completely with his massive beast. I couldn't move, I couldn't breathe. All I could do was let the tears flow down my cheeks and writhe below him as he made slow, passionate love to me.

None of the girls I had been with had made me feel the way Derrick did right then. The things I felt filled every nuance of my soul, surges of electric ecstasy coursing through me, my entire body alive with a strange, fresh energy. I shuddered and shook as he drove his cock into me over and over. My cock finally exploding all over my stomach, not just once, but twice, before I felt him pulsing deep inside me. Ruined, destroyed, he had invalidated, rewritten everything I thought I knew about myself.

Derrick tried to pull free, but I locked my ankles behind him, holding him in place. "Not yet. Please?" I half begged him to stay inside me. He just smiled, leaning down to kiss me one more time.

I think of all the things I had done since April conned me into her cheer uniform. Kissing Derrick was my favorite.

We made love twice more. Derrick would come inside me, and I would suck and play with his cock until he was ready again. We took our time exploring each other's bodies. I had never even thought of touching a man like this before, but it seemed like the most natural thing in the world.

He was the one that finally quit. "Girl, you are wearing me out. I can't do this anymore." He kissed me hard and rolled onto his back. We got up and took a shower. I looked at myself in the mirror and smiled. Even with my makeup destroyed, the boobs April had glued to my chest were enough. I could still see the girl from last night.

"Shit." I shouted when it hit me as I pulled on my panties and bra. "All I have is that stupid cheer uniform. I can't wear that back to my dorm."

"Hang on." Derrick stuck his head out the door. "Ginny, you out there? I need some help."

"Ginny?" I looked at him funny. "Who's Ginny?"

"My little sister." When the cute blonde came through the door, I twisted my confused expression even more.

"Fraternity, little sister. She lives here with me." He laughed. "Gin, you got something she can borrow. All she's got is that cheer uniform. And can you maybe help her fix her makeup?" I was positive she saw my cock in my panties, but she didn't say a word. I followed her to her room, where she helped me with all the same things April had helped me with only yesterday, except Ginny was doing it for the right reasons.

We found Derrick in the kitchen on his phone, making a protein shake or something.

"Damn, you look amazing. Better than in that cheer uniform, that's for sure." Ginny had loaned me a pair of shorts that looked painted on and a cropped football jersey with Derrick's number on it. The jersey hung off my shoulder and left just a bit of my tummy exposed. I was beyond cute.

"Thanks, and about last night, don't worry about it. I probably enjoyed it as much as you guys did." I gave Derrick a weak smile. "And this morning..." I just smiled.

"Listen, you can hang here with Ginny for a bit." He smiled back. I got the feeling he was going to want to pick up where we left off. "I've got a team meeting. A guy from the party, one they dressed as a cheerleader, is in the hospital and a couple of guys on the team were involved somehow. That April bitch did a number on those guys. I'm glad you bailed."

"Me too, and thanks, but I need to get home. Last night and this morning were too much. I need time to think; decompress." I left April's uniform in Derick's room and headed back to my apartment. When I realized Derrick didn't even know my name, I almost went back, but decided Derrick's not knowing my name might be for the best. I'd dressed up for a Halloween party, hoping to fuck the hottest girl in school. I wasn't sure I was ready to be a massive black man's girlfriend.

My roommate Ryan was still asleep, so I undressed as quietly as I could, changing into something a little more appropriate. I still had on the panties and didn't know how to get the breasts forms off, so I wore the bra, too. I guess that was part of April's joke. The panties just felt nice on my hairless crotch and if someone forced me to tell the truth, I liked the way the fake boobs tugged on my chest and moved with me. Once I met up with Derick and his friends, I'd had a good time. I smiled to myself and flexed my butt, thinking back on my morning with Derrick. Oh, boy. I couldn't believe I'd let him fuck me three times, much less that I'd wanted him to.

I tried to get the makeup off, but all I did was smear it all over my face. Ryan woke up to find me on the computer searching for makeup remover and watching tutorials.

"You and April. How was the party, bro?"

"Bitch tried to set me up as a fool. I saw a couple of other guys dressed as cheerleaders and put two and two together. It was Halloween, so I just went to a different party. Fuck her."

"Dude, you no-showed April Weathers?"

"Yeah. Good thing, too. I heard one guy they dressed up ended up in the hospital because of something she did. You know anything about getting makeup off?" We both laughed.

Ryan did me a solid and went to the drugstore for some moisturizer and makeup wipes so I could get the rest of my makeup off, and I treated him to pizza. I still had the boobs to deal with and the solvent I ordered to get them off wouldn't arrive for a few days. I'd just have to make do. We got the full story from some guys sitting at the table next to us, one of whom was at the party. April had five or six guys jack off into a cup and then forced the poor kid to drink it. She even videoed it and posted it online. She thought it was hilarious. When she told him what it was, he ran from the party and took a handful of his ADHD medicine. Lucky for him, his roommate found him.