She closed her eyes and let her head fall backwards. She let out a cute moan. “Oh God, just like that,” she said. She pulled his head in closer. I was suddenly wishing there was another bottle of vodka. That anxious edge was starting to come back and I hadn’t even realized that it was gone. I looked over at the clock and saw that it was almost 1:00 AM. We’d been playing the game for hours. Surely it was almost over—right?
Natalie came, screaming loudly. Jimmy suddenly winced back and spat out a mouthful of fluid. “Ew!” he said. “You squirted in my mouth!”
“Most guys like it,” Natalie said, narrowing her eyes and suddenly looking offended.
“No one likes that,” Jimmy said, wiping his lips. “You know squirt is just pee, right? You just pissed in my mouth!”
“Squirt is not pee!” Natalie snapped back.
“Okay, okay—calm down you two,” Anne said. “Are we going to keep playing or are we done now?” My heart leapt up in my chest. Finally, the game was coming to an end! I survived all of the humiliation. And I knew that no one in that room would tell anyone in the school about what happened, because everyone suffered equal embarrassment—everyone in that room now had secrets that they wanted to keep.
“No, we’re not stopping now,” Jimmy said. “Not after my turn. That’s not fair.”
“Well we’re going to have to stop eventually, or we’ll be at it all weekend,” Anne replied.
“Fine. How’s about one more round.”
“Well isn’t that convenient for you?” Rex said.
“Fine—two more rounds. That way it can still end on me,” Jimmy said.
“Sounds good to me,” Natalie said. Everyone nodded, and I nodded along. Though it was a bit sad to think that my time as a pretty sissy was coming to an end. Once the game was over, I would be expected to get washed up and changed as soon as possible, otherwise they would all know that I was enjoying my time in lingerie and heels.
Jimmy grabbed the bottle. He took a deep breath and then he gave it a hard spin. It spun and spun and spun while everyone watched closely. It seemed to spin forever, distressing all of us. We all knew that the final couple of dares would be especially tormenting. The game had to end with a bang.
The bottle landed on me. I looked up and saw Jimmy staring at me. He wasn’t smiling. His face was a strange pale shade as he looked into my eyes. He picked up the die and rolled it—and of course he rolled a dare, not that any of the other rolls would have been better.
“Well?” Natalie said. “What do you want her to do?” I tried not to grin when I heard Natalie refer to me as ‘her’.
“Hold on. I’m thinking,” Jimmy said with a snap. He kept staring into my eyes, as if he was trying to come up with something especially horrible. My stomach groaned. It was so close to the end of the game, and now I could tell that Jimmy was coming up with something so horrible, I would want to fuck that sex doll on camera. I bit down on my tongue and silently prayed for mercy.
“C’mon, Jimmy, I’m getting tired,” Chad said.
“Okay, okay—fine,” Jimmy said, waving Chad off. “Suck my dick.”
The room became silent. My heart stuttered as my brain desperately tried to process Jimmy’s request. Surely I couldn’t have heard him right. Surely he didn’t want me to suck him off—did he? “What?” Rex asked for me.
“I just dared her to suck my dick—for one minute.”
The room was silent again. “But… you know she’s actually a dude, right?” Chad said.
“Is that what you were thinking about when she made you come with her lap dance?” Jimmy asked with a roar. Chad became silent. Jimmy looked back at me. “Well? Are you going to do it, or do you lose?”
I took a deep breath and then I crawled over to him. I had to do it. How bad could it be? I mean—the thought of sucking a cock before I even lost my virginity was horrible, but it wasn’t as bad as fucking a sex doll on camera, so that I could be tormented by the school’s cool kids for the rest of my academic career.
Jimmy’s cock was already half-erect. I only had to do it for a minute. At least I didn’t have to do it until he got off. I stared at his curved, thick cock as it dangled before me. I hated how silent that room was. And I hated how excited I was as I thought about the fact Jimmy—the most popular guy in school—thought I was hot enough to blow him.
“You going to do it or what, beautiful?” I heard Natalie ask.
I reached out and grabbed the warm shaft. I held it up, towards my lips, and then I sunk my head down while closing my eyes. I heard the soft beep of Rex’s watch as he started the timer. So I started sucking. At least there wasn’t a gross taste—though the feeling of Jimmy’s foreskin being pulled back in my mouth was a bit off-putting. I tried not to think about it. I just pressed my lips firmly around that cock and I bobbed my head. I kept the shaft cradled on my tongue, so it wouldn’t go rogue inside of my mouth and bash around in my throat.
I could feel him getting harder and bigger. After about twenty seconds, it wasn’t so easy to get all of him inside of my mouth—but I knew I was almost half done, so I just kept my eyes closed and I kept bobbing my head. I let him into my throat, making me gag slightly. I didn’t want to give him any excuse to call me a loser. I still didn’t really know the rules of their secret sex game—maybe if the blowjob were deemed lousy, I would end up straddling that sex doll regardless. So I bobbed my head quickly. I felt his cock twitch in my mouth, and then I could taste something bitter—like warm pancake batter. Was it pre-cum? I could feel Jimmy’s veins throbbing. It was a weird feeling, having another man’s appendage in my mouth. And it was even weirder to think that he was liking it. I mean—he must have been liking it, right? He asked for it, and now he was rock hard.
His cock was throbbing quickly. I wondered if he was close to coming. Could I get him to come before the time was up? I bobbed my head quicker, arching my back downwards, so that my bum would look perkier and sexier. I pointed my toes in my heels and I lifted one foot into the air. If I was going to get him off before that timer went off, I needed to get him to a state of maximum arousal. I heard him moan. I used my tongue to tickle the underside of his tip while I stroked his shaft with my tightly pressed lips. His fingers were in my hair, grabbing tight, nearly pulling off my wig.
“Oh God,” he groaned. I heard the beeping of that stopwatch, but I didn’t want to stop. I wanted to see my blowjob through to the end. I could pretend like I didn’t hear it so that I could taste his sweet cum.
Then he pushed me back. “Time’s up, slut,” he said. “Don’t you hear the beeping?” His face was dark red. He wiped the beads of sweat off of his forehead and then he covered his massive, drool-covered erection with the palm of his hand. “Okay, it’s your turn, and it’s the last turn. Get it over with.”
I sat up slowly. I could feel the gazes of everyone staring at me. I was too embarrassed to look at their faces. I crawled back slowly, keeping my eyes down. Then I grabbed that bottle and gave it its last spin.
CHAPTER VIII
It spun and spun and spun. While it was spinning, I looked up at Jimmy. He looked away from me suddenly, as if he didn’t want me to know that he was looking at me. My mind was racing with thoughts that I’d never had before. In the back of my mind, I was still trying to come up with a way to steal a few outfits from Jimmy’s sister, without my classmates noticing.
I looked down and saw that the bottle was pointing at me. Once again, I spun the bottle on myself. I remembered the rule: the whole group decided the dare for me—but that was only if I rolled a dare. What if I rolled a kiss? Would the whole group have to kiss me? And if I rolled the ‘sexy rub’—would I have to go and rub everyone in that room?
“Roll the die,” said Natalie. I picked up the die and I gave it a good shake before letting it go. It danced and bounced on the ground, and then it revealed that rare 6. “Roll again.” I picked it up again and tossed it once more. This time, it seemed to bounce and dance forever before settling in p
lace.
“Six—that means Seven Minutes in Heaven,” Rex said.
My heart stammered. “With who?” I asked.
The room was quiet for a moment. “Well, according to the rules: with everyone,” said Jimmy.
I looked up and saw everyone staring at me. “W—What?” I said. My heart was pounding. What exactly did that mean? Were they saying that I had to get it on with all of them? One at a time, or in a big orgy? Was this that final humiliation that I’d been waiting for all night? How could they have planned this? The chance of rolling two sixes in a row was low—but not as low as the chance of me spinning the bottle onto myself in the final round before rolling those two sixes.
Natalie was the first to come up to me. She sat down in front of me with a big warm smile and then she leaned forward, kissing me on the lips. I could taste that bitter tinge of cum still on her lips, from when she licked it off of my lingerie. But that didn’t stop me from kissing back.
Then I felt a pair of soft, feminine hands on my shoulders. I looked back and saw Anne sitting behind me, leaning in to kiss my neck. My heart fluttered, and then I noticed Jeannie heading for the door. Where was she going? Was she just leaving? Was it considered a loss if she bowed out now? I didn’t say anything. I let her go, because I wished that I could go.
The two girls helped me up to my feet. “Should we take her to the bedroom?” Anne asked.
“Yeah,” said Chad. And then they started pulling me towards the bedroom. I wanted to fight back but I was too afraid. I’d come so far. I couldn’t just wimp out now. I was minutes away from being finished with the game and with the whole party. I could finally say that I was part of one of Jimmy’s epic parties—though I could never tell anyone what happened within those sacred walls.
Rex was already on the bed, on his back, with his erect cock in his hand. He had it aimed up, ready to penetrate me ass. The girls helped me up onto the bed. They each grabbed a leg, spreading them before guiding me downwards. “W—What are you guys doing?” I asked.
“Don’t worry,” Natalie said. “It will all be over in seven minutes.”
I felt Rex’s warm tip pressing between my butt cheeks. One of the girls pulled my lingerie to the side, so that my asshole was exposed and vulnerable. Then, I felt pressure on my shoulders as they tried to push me down onto the cock. “I’m a virgin,” I said.
“We know—you told us a couple of hours ago,” said Anne.
“In seven minutes, you won’t be a virgin anymore. Aren’t you excited?” Natalie asked with a big smile. She leaned forward and kissed me again, giving me another taste of that bitter cum that refused to leave her lips.
I felt that tip press into my hole. I gasped and clenched and bit down on my tongue. “It hurts,” I said.
“It won’t. Just relax,” Natalie said. I tried to take a deep breath. One of the girls was rubbing my shoulders. And I wondered: was this better than fucking that sex doll on camera? Was it too late to take that embarrassing option—before that cock ended up any deeper in my anus?
Jimmy was standing ten feet away from me now, stroking his cock slowly as he watched me getting stuffed by Rex’s long appendage. I looked into his eyes, hoping he would be the one to have mercy on me, but I could tell that he was just waiting for his turn. Chad was next to him, standing slightly behind as if there was a line-up.
I looked away. My heart was pounding ferociously fast. I was worried I was about to pass out, and I was wishing I would have been more boozed up, so that this memory wouldn’t exist in the morning. But now, I was completely sober—not even a little bit buzzed.
“Fuck—she’s so tight,” Rex groaned. His cock was almost entirely inside of me now. I could feel it pressing up towards my sternum, stretching my tight hole impossibly wide. I clenched again, but that didn’t stop the girls from pushing me down further. Rex groaned even louder. “Bounce like the slut you are,” Rex said, once his whole cock was inside of my body.
So I started bouncing. The girls held me upright. It was Natalie who reached into my lingerie and fished out my cock. “She’s hard,” she said, wrapping her fingers around my cock. She started to jerk me off.
“Does it still hurt, darling?” Anne asked with a warm, gentle voice.
I shook my head. The pain was gone, but I couldn’t speak. There was a lump in my throat and my whole world was spinning in fast circles.
I was bouncing up and down on a cock. I was no longer a virgin. And I would always remember the way I lost my virginity: dressed like a chick with an audience of my classmates.
It was Natalie who decided she wanted in on the action. She climbed up onto the bed, turned around, and lowered her pelvis down until it was in line with my cock. She asked Rex and me to stop for a moment while she lowered herself in for landing. She squished her wet pussy against my cock and wiggled until I penetrated her. Then she told us to carry on while she hovered in place, getting her pussy fucked. I couldn’t believe how wet she was—literally dripping onto the bed. Her pussy made a squishing down every time my cock pressed into it. I grabbed her hips firmly—to hold her in place and to hold myself in place. She kept pushing her bum back, until it was pressed firmly into my lap.
The euphoria was overwhelming. I tried not to scream but I knew screaming was inevitable. I bit down on my tongue, almost making myself bleed. And then I heard Rex groaning loudly. His fingers dug into my sides and then I felt a series of hot bursts deep inside of me.
He suddenly pushed me off of me, rolling Natalie and me over, so Natalie was flat on her stomach and I was on top of her, still with my cock in her snatch. I felt Rex’s hot load rushing towards my stretched anus. I tried to clench it back, but I couldn’t stop it.
“Get in there—quick!” Rex shouted. And then I looked back to see Jimmy mounting me. He pressed the tip of his cock into my ass, plugging me as if he was corking an upside-down wine bottle full of shampoo. Then he started pushing his cock in. No amount of clenching would hold him back. He was determined to get inside of me entirely. And it was only ten seconds before he had his whole cock in me. He started to thrust, squishing his friend’s load around inside of my butt. It was a weird feeling—and an amazing feeling. The euphoria was intense now. I started screaming as that pleasure started to centralize between my legs. I clenched and then I tried to warn Natalie that I was about to cum inside of her. “It’s coming!” was all I managed to say.
“Fucking come in me, you sexy slut!” Natalie said. So I stopped holding back. I filled her little pussy with my warm load. She groaned and grabbed two handfuls of bed sheets.
Jimmy only took a few dozen seconds to come. Apparently he was still on the verge after my blowjob. Chad took his place quickly, making sure none of that sweet jizz poured out of me. Now I could really feel it sloshing around inside of me as it coated the entire length of Chad’s rod. Chad pumped me quickly, coming quickly—but the act wasn’t over.
Jeannie was next in line, with a strap-on dildo synched tightly around her hips. She walked forward and pressed all three creampies deep into my body with the big plastic toy. She only fucked me for a couple of minutes before climbing up on the bed to make me suck all the different flavours of cum off of her fake cock.
I wasn’t able to stand once it was all over. Natalie managed to crawl out from under me. Everyone went to get cleaned up—but even once they were all dressed, I was still limp on that bed. My ass was sore but that euphoria was still pulsing through my veins. It was Anne who asked, “Are you okay, Devon?”
I nodded my head. “Just fine,” I said with a groan. I could feel all of that cum down my ball sack and pooled around my cock, as if someone poured a whole pint glass of piña colada down my crotch. Anne reached her hand out and helped me to my heeled feel. I wobbled and then she caught me. “You did good,” she said.
I looked into her pretty blue eyes. “Are you guys going to tell everyone at school about this?” I asked.
“What? Why would we do that?” she asked.
&n
bsp; “Is that why you invited me—to make fun of me?”
She shook her head and laughed. “No. We just invited you because we thought you would be fun to hang out with—and we were right.”
It was a minute later when Jimmy walked up and gave me a firm pat on the back. “That was fun, Devon. You should come out next weekend. We’re having a big house party.”
“I’d like that,” I said.
“And, I don’t know—maybe you could come dressed like a chick. You make a fun chick.”
Rex was nodding his head in the corner. “Agreed,” he said without looking over. And maybe it was just my gullible nature, but I actually believed them. Maybe they were right—maybe I did make a better girl than I did a guy. Maybe these jocks and cheerleaders weren’t as bad as I thought they were. Maybe they didn’t have some mean agenda, just because they were popular.
“I’m going shopping tomorrow. You should come with me,” Jeannie said. And it was a moment before I realized she was talking to me.
“Really?” I asked.
“Yeah. I know a cute little dress shop that has so much stuff that would look so cute on you.” My heart throbbed. I tried telling myself that it was just the liquor, but I knew that I was completely sober. I really was just excited to play sissy dress-up—and maybe there was nothing wrong with that. It’s not like I was hurting anyone by wearing cute clothes and a bit of makeup. It’s not like people would look at me and think that I was some mentally deranged lunatic. I really looked like a chick with a wig and a bit of makeup.
Womanized Page 40
