I slipped on the thong and then I got into the tight cheerleader costume. I put on the wig and I even put on the pom-poms. I skipped over to the mirror and then I did a little hop. I looked cute. I didn’t even mind my flat chest in the little outfit.
I caught myself smiling as I spun around. And then I felt my panties tightening. They got tighter and tighter and then my cock broke free from its tiny satin prison, flopping out and pushing the small cheerleading skirt up into the air. My cock was twitching and throbbing, begging to be stroked. I reached down slowly and wrapped my fingers around it. My face was dark red. Why was I so excited? Why was this so arousing? Was this some sort of consequence of the emotional abuse I took back in high school?
I gently stroked my cock, watching in the mirror. I didn’t even want to blink. I didn’t want to miss a second. I suddenly felt incredibly jealous of Theo and his massive closet of lingerie, clothes, and wigs. I wanted to try it all on. I wanted to have full access to it the way he did.
And then I started fantasizing about the approaching night. A part of me wanted to lose that game, so that I could feel what Theo felt. I wanted to scream the way Theo screamed. I wanted to convulse and groan and squirm the way Theo did.
My legs trembled and then I shot cum into the air. I suddenly gasped and then used my free hand to cover my tip, so I wouldn’t make a giant mess of Theo’s guest room. I couldn’t believe how quickly I came. I hardly even touched my cock—maybe three strokes at the most. Did that cheerleading costume really make me that horny?
I cleaned up my mess and I got out of that little outfit. I poked my head out into the hallway before darting back across to the girly bedroom to put everything back where I found it.
When I got back downstairs, everyone was still sitting on the couches, looking out at the lake, still chatting openly as if the previous night had never happened. And those smiles were still on their faces.
CHAPTER VII
I took a shower around 4:00 PM. It was a long shower and my cock was rock hard the whole time, begging to be stroked. I couldn’t remember the last time I had such a strong urge to jerk myself off. But now, I didn’t want to jerk myself off—because I didn’t want to get off to the image that was in my head, of Theo on his hands and knees, which his heavy ball sack dangling between his thighs. At least in my imagination he was still dolled up, still wearing that wig and that little white dress—but it was still Theo, and that cock was still part of the package.
When I returned downstairs after my shower, the game was set up: the board was out, the little train pieces were placed before each chair, and the cards were all shuffled and placed in their proper piles. The guys were lingering around the table, topping up their drinks, getting ready to sit down. The smiles were finally gone from their faces. The reality of the deal we made the night before was finally setting in. Someone was going to lose, meaning someone was going to be getting a cock in their ass.
“Is everyone ready to play?” Jimmy asked. But the room was silent. The tension was thick and heavy. Ben was the first one to approach the table. He gently pulled out his chair and then took a seat. He looked down at the main pile of cards—the ones that essentially dictated the outcome of the game. He reached out and started shuffling them, just in case Jimmy had cheated when he set the game up.
Theo sat down next. For him, the there was a different tension. His face was a slight shade of white. Maybe he was hoping for one guy over the others, or maybe he just felt guilty that one of his friends was about to do something they didn’t want to do, for him. I took the next seat, and I also found myself watching Jimmy closely. Even when he sat down and started dealing the first round of cards, I found myself watching his sleeves, making sure he wasn’t hiding the best cards in the game from us.
“Who goes first?” Theo asked.
“According to the rules, the most experienced player always goes first,” Ben said, even though we’d gone over it the night before. And that meant Ben got to go first, which didn’t seem fair, even though there was technically no advantage to going first—at least that I could figure out.
The room wasn’t nearly as lively as the night before, and the game didn’t move nearly as quickly. Every player took the time to make sure they were making the best possible move every time it was their turn. There were many different strategies to try, but having only played the game once before, how could I know which was best? Ben could possibly know, having played the game many times before. He owned it, after all… But maybe one of the other guys looked it up on the Internet. Maybe there was some website that knew all of the best places to lay down trains to get the maximum number of points. There are always borderline autistic people figuring stuff like that out.
And I couldn’t help but wonder if Jimmy had looked it up before we started. He was playing out a peculiar strategy, laying down lots of tiny trains all over the board with seemingly no pattern. Every turn, he would lay down the smallest possible train instead of saving up his trains to make big, long ones worth more points. Did it make more sense to make lots of little trains? Did he know something that the rest of us didn’t?
He was also picking up lots of ‘destination cards’. Each destination card had two random cities on it. The players keep the cards hidden until the end of the game, and if they have their destinations linked with trains, they get extra points. But if they aren’t completed, then they lose points. We were halfway through the game, and Jimmy already had nearly ten destination cards sitting in front of him—and if even half of them were completed, then he would definitely be the winner.
Ben was playing with the opposite strategy. He was only laying down six car trains—the biggest possible in the game, worth the most points. He would spend every turn collecting trains until he had enough of a single colour to make his maximum-sized tracks. But he wasn’t picking up any destination cards. Maybe he didn’t want to risk losing points. Maybe he didn’t care about winning, as long as he didn’t lose. Maybe the best strategy was to play it safe.
I felt lucky. At the start, I was dealt three super easy destination cards, which I managed to complete within the first ten laps around the table. I didn’t try to pick up anymore, knowing the game could end at any time—especially with Jimmy throwing down all of his trains as quickly as possible. The game ended once the first player ran out of trains, so I had to play carefully. I was in second place on the board, but the score on the board didn’t include those secret destinations.
I was about to lay down my biggest train of the game when Jimmy put down his last piece and said, “That’s it—I’m out of trains.”
“I guess the game is over then,” Ben said. And that silence overtook the room again. My heart stuttered. Had I gotten that last train down, it would have put me in first place on the board—a whopping fifteen extra points on my score. But instead, I was down in second place, only about twelve points ahead of Jimmy, who still had all of his destination cards to reveal.
Ben revealed his destination cards first. He was in first place already, so the extra twenty-five points he got just solidified that victory. I only got twenty points with all three of my destination cards—apparently my destinations weren’t worth much, and maybe that explained why they were so easy to accomplish. So I was only thirty-two points ahead of Jimmy, who had nearly a dozen destination cards and trains all over the map. He flipped over his cards and started counting. We all leaned over the table, and I swear I could hear Ben’s heart pounding.
But Jimmy had almost nothing. He completed two destinations, and actually lost points for all of the cards he was hoarding. He fell back fifteen points, putting him in dead last place. A wave of relief washed over me. Jimmy was the loser. Jimmy had to get dolled up for Theo, so that Theo could lose his virginity.
I didn’t look into Jimmy’s eyes. I was afraid to see the fear on his face—the fear that could have been on my face had I attempted a risky strategy like him. He stood up. “What now?” he asked.
“First
, I’ll help you do your makeup,” Theo said.
The room became silent again for a moment. “Where do you want to do it?”
“Up in my sister’s room. Come on,” Theo said.
Ben and I stared at each other while the two went upstairs. “Good game,” Ben finally said, breaking the silence once Theo and Jimmy had disappeared.
“You too,” I said. “You played a good strategy.”
“I just got lucky with cards. There was no strategy.”
“What do we do now?” I asked.
“I guess we just hang out.”
“Do you think he’s really going to go through with it?”
Ben shrugged his shoulders. “I think so. I’m pretty sure he lost on purpose.”
The suggestion made my heart leap. Then Ben reached out and grabbed Jimmy’s destination cards. “Look,” he said. “He only got two of his destinations, but there’s more than ten cards here. So assuming he got his first two finished, which I don’t think he did, then he just kept picking them up. You can only pick up three at a time, which means he picked up another three even though he didn’t have the last three—and then he picked up three more. And surely he knows that you’re allowed putting two cards back if you don’t want them.”
“Maybe he thought that he would get them throughout the game,” I said.
Ben shrugged his shoulders again. “Maybe—but look at where he was putting his trains. Some of them are nowhere near any of his destinations.” And it was true—some of Jimmy’s trains were way on the other side of the board from his card’s intended destinations. He lost on purpose. He wanted to get dolled up and fucked in the ass.
My heart stammered down into my gut. I couldn’t wrap my head around why Jimmy would lose on purpose. Why would he want to be sissified and fucked? Had all those years of bullying left him like me—only able to get fully aroused with the help of some lacy panties? Or was the trauma worse for him? Did he need full-on sissification to get off?
It was thirty minutes later when we heard a door close upstairs. Was Theo done dolling Jimmy up? Were they getting the fucking underway?
Ben stood up and then he walked over to the back door. He turned around and looked at me. “Come on,” he said with a hushed voice.
“Come on where?” I asked. Then he shushed me.
“Just follow me.”
So I followed Ben outside. We walked away from the house. Ben was looking up at the windows, circling the house until he spotted the room where the action was happening. It was the room across the hall from mine—Theo’s sister’s bedroom. We could see the glow but from our angle, we couldn’t see the action inside. But Ben had a plan. He walked over to a tree and then he started to climb. “What are you doing?” I asked.
“I want to see,” he said. “C’mon—I’ll help you up.” He reached his hand down and I grabbed it. He helped me up onto that first thick branch. It was easy to climb up from there. I followed him up and up and up, until we were eye-level with that bedroom. Ben reached out and parted the tree’s leafy branches so we could see into that room. And there was Jimmy, all dolled up with a curly blonde wig and lots of eye makeup. He was standing in a little white floral dress and tall black high heels. His legs were smooth and his hands were clasped at his waist in a nervous way. Theo was standing by the door, getting himself undressed. We watched as his pants fell to the ground, revealing his long cock. His crotch and legs were shaved, giving him a feminine sort of appearance, but unlike Jimmy, he wasn’t dolled up.
“She looks pretty good, huh?” Ben said. “She’s super cute in that dress.”
I didn’t know how to reply. I didn’t like that he was calling Jimmy ‘her’, though it was hard to think of him as anything else in his current state. Maybe ‘her’ was more appropriate. Maybe she really did pass as a woman.
It was Jimmy who waved Theo over. He walked up to her and then she reached down and grabbed his cock. We were far away, but we could still see that her hands were trembling. That was no surprise—I would have been nervous as well. I may have even passed out if that was me in that little dress.
She massaged his cock, getting him hard. And his cock grew quickly to an impressive size, standing upright and throbbing with thick veins. Jimmy’s lips parted at the sight of the large cock. She stood in awe, until Theo pushed down on her shoulders, making her sink to her knees. It was only a few seconds before that impressive cock was in Jimmy’s mouth. “She’s just taking it,” Ben said. “I knew she lost on purpose.”
“Do you think she’s done this before?” I asked. My voice cracked in an embarrassing way. I bit down on my tongue and hoped that Ben didn’t notice.
“I don’t know. I don’t think so. I believed her when she said that she was a virgin.”
But she sucked a mean cock for a virgin. She bobbed her head quickly and elegantly while holding onto Theo’s thighs. The couple was perfectly profile to the window, making it easy for us to see all of the action.
“Fuck, she’s hot,” Ben muttered—so quietly that I almost didn’t hear. I wasn’t sure how to reply. Was Ben really attracted to Jimmy? Did he forget that Jimmy was actually a boy—and our friend? Or did he not care?
Jimmy kept sucking faster and faster. Theo’s face was starting to turn red. He let his head tilt back, and then he pushed Jimmy away, probably worried he was going to erupt in her mouth. He pointed to the bed as Jimmy carefully rose to her feet, wobbling slightly in her tall heels. That’s when I noticed her erection, pushing the skirt of her dress forward. She reached down and tucked it back into her panties, but I’m sure Theo had already noticed. He didn’t seem to mind. He followed her right to the bed, bending her over and flipping up her skirt to expose her round, soft bum. He grabbed it with both hands and squeezed. Jimmy’s lips parted and it looked like she was already moaning. Theo’s cock was dripping with Jimmy’s saliva.
“Tell me the truth,” Ben said suddenly, making me jump as he cut the night’s silence.
“What?” I said.
“Were you trying to lose as well?”
My heart skipped a beat. “What? No—of course not. I would have beat you if we had just a few more turns,” I said. My heart was racing. Why would he think I tried to lose? Why would he think I wanted what Jimmy was getting now?
Unless he tried to lose. Maybe that’s why he didn’t pick up any destination cards. Maybe he thought we would all pass him with our destination points. Maybe he really did just get lucky with the cards he was drawing, and maybe he thought that we would be better. There was now a familiar tennis ball sized lump in my throat.
We both turned our attention back to the window. Theo was now pressing the tip of his cock between Jimmy’s butt cheeks. Jimmy was clenching the bed sheets with both hands. His face was red and clenched. Theo rubbed his soft bum gently, and then he pierced his cock in. Jimmy tensed up and his gasp was almost audible from out in those woods. Theo sunk in deeper and deeper, until his pelvis was pressed hard against Jimmy’s ass. Then he started fucking the cute sissy.
I carefully looked over at Ben, who was watching with big, mesmerized eyes. And maybe there was a hint of jealousy in those eyes. Maybe he did wish that he were Jimmy, getting pumped and stuffed. Jimmy was squirming and groaning and the elation on his face appeared overwhelming. Maybe there was something to it. Maybe it would feel really good, especially with a nice thick cock like Theo’s. Jimmy looked like he was having an orgasm that was lasting minutes instead of seconds. I couldn’t even begin to imagine that kind of pleasure.
Theo’s face was red. He was thrusting quickly, holding Jimmy tight. Jimmy’s body was convulsing with pleasure. Beads of sweat were beginning to form on his forehead. There was a big grin on his face and his eyes were shut tight. “Oh God!” he screamed, and it was loud enough that we could hear outside.
Theo groaned loudly and then he pulled his long cock out. He pushed Jimmy down onto his stomach and then he started unloading long strands of cum all over Jimmy’s ass and dress-clad b
ack. He reached down and smeared the cum all over Jimmy’s soft, round cheeks. He even used a finger to push some of that cum up into Jimmy’s asshole. And Jimmy was still smiling, still high on a euphoria that I couldn’t even begin to understand. Maybe I should have lost the game. Maybe I had missed out on an amazing opportunity.
CHAPTER VIII
It was the next morning when I saw Jimmy in person for the first time following that hard fucking he received from Theo. He came down the stairs with a grin that stretched from ear to ear. He went straight for the coffee pot and poured himself a big, steaming mug. His eyes were glowing, and so was his skin. He almost looked like he’d taken a bath in tub filled with liquid diamonds. He looked at me slowly and said, “Good morning. How’d you sleep?”
“Fine. And you?” I asked.
He nodded his head slowly. “Best sleep of my life,” he said.
Ben was watching Jimmy closely from across the room. I could see that jealousy flashing in Ben’s eyes. Maybe he did try to lose the game the night before, or maybe he was now wishing that he had tried to lose.
It was our last day at the cabin—one more night night before it was time to pack our bags to go home. And that meant that it was my last day with access to that amazing bedroom filled with those amazing dresses and lacy pieces of lingerie. It was 11:00 AM when Theo and Ben went down to the lake to try to catch some fish for dinner. Jimmy went to his room to take a shower, so I figured it was my best chance to go try on some more outfits. I rushed over to that girly bedroom and I started to fill my arms with all of the dresses and skirts and pieces of lingerie that I wanted to wear. I grabbed that same brunette wig and then I took it all over to my room. And then I started thinking about makeup. After seeing how beautiful Jimmy and Theo both looked with a big of mascara and eyeliner—I wanted to see how beautiful I could look. So I snuck back across the hall and grabbed a few more things.
Womanized Page 30