Jimmy reached up and wiped the sweat off of his forehead. I looked over at that board game on the table. My heart stuttered. Were we really going to play that game to decide who takes Theo’s cock in the ass? I walked over to the game and pulled out the rulebook, hoping to familiarize myself with the rules, to give myself a better chance of winning. I didn’t even have to win—I just had to not lose.
But I couldn’t focus on that rulebook because now I could hear more sounds coming from that room: a sharp gasp, a long exhale, and then a series of loudening moans.
Jimmy was completely frozen on the couch, staring at the fire with a sunken gaze. Was this really how he wanted to lose his virginity? Was this how I wanted to lose mine?
“Shit!” that girly voice cried out from behind that closed door. We could hear the slapping of Ben’s pelvis against Theo’s ass. They were really doing it—or were they just messing with me? Was it possible that this was all still just a set up to humiliate me? If so, why would they do it? Why would they go to such great lengths?
“Oh God! I can feel it!” Theo cried out. I was impressed that he was still making that girly voice.
Ben’s loud groan nearly shook the house. Then, there was silence. I tried to look back down at that rulebook, but my vision was blurred now. And even if my vision had been fine, my hands were shaking too much to read those words properly. I was a terrified mess. Maybe this wasn’t such a good idea. If I didn’t go in there to fuck Theo, did that disqualify me from possibly getting dolled up and fucked tomorrow?
Ben came out from the bedroom. His face was white and his eyes were glowing. He had an awkward smirk on his face as he stumbled slightly. Theo appeared in the doorway behind him a moment later. Her face was flushed as well, but she was grinning. She looked right at Jimmy and then waved him over. He stood up slowly, wiping more of that cold sweat from his forehead. He straightened his back and then he started walking forward. I watched from my distance. I couldn’t believe those grins.
Ben had only been in that room for ten minutes, and I had a feeling Jimmy wasn’t going to last quite as long as Ben, which meant I only had about ten minutes to make up my mind. Would I do it or would I pass? I watched as Ben walked over to the bar. He poured himself a tall glass of scotch and then he took a long sip. His hands weren’t shaking anymore. He looked calm and relaxed, still with that grin on his face. I bit down on my tongue and took a deep breath. “Well?” I said. “How was it?”
He looked at me. “Amazing,” he said. Then he took another long sip before reaching for a cigar. He looked at me again. “Don’t worry. Once you get going, all the fear washes away.”
I watched him closely as he lit his cigar and started puffing with that big smile on his face. I couldn’t believe what I was seeing. Was he just acting? Was this part of some ‘gotcha’ game they were playing?
Then I heard a sharp gasp coming from inside that bedroom. Then I heard moaning, but I couldn’t tell if it was Jimmy or Theo—Theo could do the girl voice perfectly, and Jimmy had a naturally girly voice to begin with. “Oh fuck, oh fuck—oh my God—that feels so good.” I was pretty sure that part was Jimmy.
“Just be gentle with her,” Ben said suddenly. “Remember that she’s a virgin too.”
I looked away from that doorway and from Ben. My heart was pounding ferociously. I was starting to worry that I would pass out before I even had a chance to get into that room with that tall blonde. What if I came too quickly? What if I couldn’t get hard at all? What if I couldn’t come and I spent an hour pumping my friend’s asshole? What if I woke up in the morning with nothing but regret?
I heard Jimmy scream, and then the house was silent again. I looked over at that door and waited for it to open. I could only hear the clock ticking on the nearby wall. Suddenly, that door opened and Jimmy came out. His face was flushed and he was smiling, just like Ben. He walked over to Ben and they gave each other a high-five. “Good, huh?” Ben said.
“Amazing,” Jimmy said.
And then I noticed that feminine figure standing in that bedroom doorway. She was looking right at me. And I couldn’t help but notice the long streaks of cum down her perfect legs. “Ready, Vinnie?” she said in a strangely alluring voice.
I stood up and then I nearly fell back down. My knees wanted to buckle, but somehow I stayed upright. I took a deep breath before looking back at Ben and Jimmy. They looked happy and relaxed. Maybe I would be happy and relaxed too if I went through with it. I took a few steps towards her. She smiled at me, making my heart skip a beat.
“You sure you want to do this?” I asked.
“What’s one more time?” she said with that big grin and that convincing voice.
And I still couldn’t get over how convincing she was as a complete package. I didn’t look back as I walked into the room. Theo closed the door and then turned to look at me. “We can go as slow as you want,” she said.
“Okay. Sure,” I said, forcing a smile.
“Get undressed,” she said.
I took another deep breath. I pulled off my shirt and then I unzipped my fly. She was suddenly standing right in front of me with her fingers around the waistband of my pants. Maybe I wasn’t moving quickly enough for her. She started shimmying my pants down, along with my boxers. I had the urge to cover up my cock, so I did. Then she grabbed my hand and moved it aside. “Don’t be shy,” she said.
Now, she was looking at my exposed cock. The last time that cock was out in the open was when those bullies were waxing my body so they could dress me up like a girl and mock me. Theo reached out and wrapped her gentle fingers around my cock. “You’re big,” she said. “And so warm.”
She smelled nice. She was definitely wearing perfume. And where did she get it? Was it her sister’s, or was it her own? And the dress—was that her sister’s or her own? And what about that big black dildo in that nightstand—maybe that wasn’t her sister’s…
“Does that feel okay?” she asked. And that’s when I realized she was rubbing my cock, massaging it and trying to get it hard.
“I guess so,” I said. My voice cracked slightly.
“Don’t be shy. We’re just going to have some fun.”
“This is just so… weird,” I said.
She smiled and then she sunk down to her knees. She held up my cock and slipped it into her warm mouth. She started to suck. My body trembled. I looked down and watched her beautiful head bobbing back and forth. It really did feel good—and it was a sight that I’d always wanted to see: a girl sucking my cock. I reached down and slipped my fingers into her soft blonde hair. She let a little muffled moan slip, and then she started to tease my tip with the tip of her tongue. “That feels good,” I said.
She kept sucking and sucking. And then she pulled her head back and said, “What’s wrong?”
“What do you mean?” I asked.
“You’re still soft,” she said, holding up my limp cock. My heart stuttered. I didn’t know why I was still soft. And now, I was terribly embarrassed.
“Let me try,” I said, grabbing it. I began to jerk it, hoping to find a sweet spot to make myself hard. But it wasn’t happening. Maybe the booze was getting to me, or maybe it was the pressure of the situation.
“Do you want to try on my panties?” she said suddenly, taking me off guard.
“What did you just say?”
“Try on my panties. Maybe that will do the trick.”
She reached under her skirt and then pulled a pair of red lacy panties down to her feet. She stepped out from them and then passed them to me. I held them for a moment as my brain tried to process what was happening. Then, I bent over and started slipping them on, feeling more embarrassed than ever before in my life. I wondered if the guys outside could hear us—if they were listening in and giggling at the fact I couldn’t get my cock up so that I could lose my virginity to one of my best friends.
The panties were tight. They felt strange on my body. Theo leaned back and looked down at me with a big smi
le. “You’ve got beautiful hips,” she said. And then I suddenly remembered high school all over again. The girls used to make fun of me because of my wide hips. They would call me girly boy, and it was the whole reason they started dolling me up in the first place.
Theo stepped around me and then she reached around and started rubbing my cock in small circles, as if she was rubbing a clit. Though I had to admit, it felt good. I stared down and watched her pretty fingers moving. And then I watched as my bulge began to grow bigger and bigger, until Theo reached her fingers into my panties and fished out my erection. “There you go,” she said. She gently pulled back my foreskin and began to stroke my throbbing shaft.
I was speechless. The panties actually worked. What did that mean? Would I need to put on a pair of panties every time I went to fuck a chick? What would girls think of that? Would they think that I was a deranged lunatic? Was I a deranged lunatic?
She got back on her knees and she continued sucking me off. I’d never been so hard in my life. My cock even hurt a tiny bit, as if it was being stretched out for the first time.
“That’s so much better,” she said with a big smile. I wondered if Theo was gay, or if he was just really good at getting into character. He sure knew how to suck a cock. If I ended up losing that board game, I certainly didn’t know how to suck a cock. I wouldn’t be able to bob my head with so much elegance.
“You’re going to make me come,” I said, biting down on the edge of my tongue.
“Then let’s get to it,” she said, standing up and then walking over to the bed. She walked with so much elegance, stepping one foot in front of the other like a supermodel. Her bum jiggled slightly with each step, making my cock throb even harder. She crawled up onto the bed, on her hands and knees. Then she stopped, with her butt facing me. I could see those long streaks of dried cum down her thighs, reminding me that I was her third date of the night.
She pressed her thighs tightly together before flipping up her skirt, to hide her cock and ball sack, which were hidden by her panties for the men before me. Now, her anus was exposed. It was slightly agape from being fucked twice already, and there was dried cum petering off in multiple directions from that hole. I walked up slowly and put my hands gently on her bum. It was soft, like a woman’s bum should be—at least how I imagined a woman’s bum should be. I squeezed and then I gave her a little spank. She jumped slightly and let a soft whimper out. Then I climbed onto the bed with her.
I took a deep breath and I tried to muster up the courage to step away. I couldn’t figure out why I was going through with this. Why wasn’t I stopping myself? Couldn’t I tell that this wasn’t right? Was this really how I wanted to lose my virginity? Would my life really be better with my virginity out of the way? I couldn’t come up with any answers to any of the questions swirling around in my head. Instead, I just pressed my tip up to that tranny hole and I started to push in.
Considering she’d been fucked twice already in the past hour, she was surprisingly tight. She clenched down on my cock, stopping me for a moment, and then she relaxed, allowing me to sink in deep. Her hole was warm and gooey—probably still filled with a bit of cum from the men who had her before me. But in that moment, I didn’t mind. It didn’t gross me out like I expected it to. I sunk in deeper and deeper, pausing only when she clenched. I could feel her tight anal walls throbbing against my member. I held on tight to her hips and even sunk my nails slightly into her skin.
“It’s so tight,” I said.
“You’re so big,” she replied.
I took one last moment to try and gather myself. But now I only had one thought in my mind: I was no longer a virgin. I felt that sly smile cross my face as I started to pump my tall blonde date. I looked down and watched as my veiny shaft pulled out and pressed in. I watched as her anus hugged my cock firmly, stretching back every time I pulled back, and then sinking in every time I pushed in. It felt good—too good. I wasn’t sure I wanted it to feel as good as it felt. I didn’t like to think that fucking my male friend could feel so amazing—but it did. It felt better than any masturbation session I’d ever had. I already felt like I was about to come—about to embarrass myself with a premature ejaculation. I had to bite down hard on my tongue to stop myself from having a five-pump orgasm. I sunk my nails deeper into her skin.
She cried out. “Fuck me! Fuck me! Fuck me!” she said. She was pushing her bum back into my pelvis. “Oh fuck! That feels so good! Shit! Don’t stop! You’re going to make me come!”
Her bum rippled every time I slammed my pelvis into it. Her legs were trembling and her fingers were clutching at the bed sheets, pulling them off of the mattress. I bit down harder on my tongue. I didn’t want to spoil her orgasm, but I wasn’t sure I could hold on much longer. I groaned and clenched and closed my eyes—but nothing could stop that amazing climax. I pushed in hard and started filling her tush with my hot cum.
She groaned and let her head fall down onto the mattress. It was over. My virginity was officially gone—and I’d officially fucked my friend from high school.
CHAPTER VI
I’m not sure how I managed to fall asleep that night. My mind was swirling with a combination of anxiety and excitement, and I had ten-year-old memories pulsing in my brain along with brand new memories that would be with me forever. I couldn’t stop thinking about Theo in that little dress and that blonde wig. I could still feel that soft bum slapping against my pelvis, and that tight anus clenching my hard rod. I fell asleep with a smirk on my face, and then I woke up late the next morning with terror pounding in my heart.
I got out of bed slowly while trying to figure out if the previous night was just a dream or if I really had lost my virginity. The events were so vivid and I had a headache from all of the scotch I drank—so it must have been real.
I was the second one awake. Jimmy was already down in the kitchen, sipping a cup of coffee. He looked up at me as I came down the stairs. He smiled. “Good morning,” he said casually. And I couldn’t see any awkward regret on his face. In fact, he seemed livelier than ever before.
“How’d you sleep?” I asked.
“Best sleep of my life. How about you?”
“Yeah—I slept well,” I said. I poured myself a coffee, still watching Jimmy closely, waiting for him to crack. Was he really happy with everything that happened the previous night? Was he not feeling any regret whatsoever? How was it possible?
I took a long sip from the coffee. I took a seat and stared out at that lake, glistening in the morning sun. I was still trying to decide if I was feeling any regrets. I expected to wake up with nothing but regret, but now, I just felt that same strange sense of relief that I felt when I finished filling Theo’s ass with cum.
Ben was awake next. He came down the stairs with a smile on his face—the same smile he had when he emerged from the bedroom with Theo. “Good morning, fellas,” he said. “Nice to see all of you today. I hope everyone slept as well as me.” He stretched out his arms. “In case you’re wondering, I’ve never felt better in my life.”
Jimmy smiled. “Ready for our big board game battle tonight?” he asked casually. Neither of them seemed worried about the fact they could end up getting dolled up for Theo. Maybe they were just confident that they wouldn’t lose. Maybe they didn’t really believe that they would be the ones bending over. They probably thought that the deal was done for them.
But I wasn’t so confident, even though I wasn’t the loser of our first game—I wasn’t the winner either. And it wasn’t necessarily a game of skill. More than anything, it was a game of luck. Sure, players could choose their own paths in the game, but ultimately, it came down to who got the better cards.
Theo came down an hour later, dressed as himself. I was expecting him to be awkward and uncomfortable around all of the men that fucked him in the ass, but he was even more calm and casual than the others. He grabbed a coffee and then migrated over to the couch, sitting down with a big, relaxed exhale. “I love this old cabin
,” he said. “I’m glad my parents never sold it.”
I kept my distance, watching everyone closely, still trying to figure out if the whole previous night was just a dream or if we really did take turns fucking Theo in that bedroom. While everyone was chatting in the living room, I slipped away. I went up the stairs and down that hallway, into Theo’s sister’s room. I slipped in quietly, leaving the door open so that I could hear people coming. I went over to the closet and quietly pulled it open. It was packed with clothes: dresses, skirts, tops, leggings, and so much more. I opened one of the drawers and my heart skipped as my gaze landed on lots of pairs of panties. I gently lifted a red pair up. It wasn’t too different from the pair I put on the night before.
Deeper in that same drawer I found a selection of thongs. There was a black lacy thong with a satin bit on the crotch that made my heart erupt into a frenzy of pounding. I held it in my hand, rubbing my fingers on that soft satin.
Then my gaze locked in on the bottom drawer. It was closed, but I could see a little bit of black lace billowing out. I sunk down and opened the drawer. It was filled with lingerie. Right on top was a black lacy teddy, and under that was a white satin nightdress, with the cutest, tiniest skirt.
And then I saw the slutty little cheerleader costume. My heart stopped beating for a moment. I suddenly remembered those cruel cheerleaders, pulling me into that drama classroom. They made me do that cheer, in a costume that wasn’t so different from the one I was looking at now.
I picked it up and felt the fabric in my hands. It was soft, and it had a tinge of perfume on it, as if it had been worn by a beautiful-smelling woman.
In another drawer I found a selection of wigs, including the blonde wig that Theo wore the night before. I suddenly found myself wondering if any of this belonged to Theo’s sister, or if it was all his. I grabbed a long brunette wig and then I ran my haul across the hallway, into my room. I locked the door and I stayed far away from the large picture windows, even though they just looked out at the trees. I didn’t want to take any chances.
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