One Tiny Problem Pt. 04

Amelia was the one who invited me to the party; the party that pivoted the way I looked at my life. I mean, from then on I've pretty much segmented the history of me in my own head into things that happened in my life before that party and things that happened after, because it changed my perspective so much about people and sexuality. A loss of innocence, I suppose. Which wasn't entirely a bad thing.

The party was on a Saturday night in Baton Rouge at the house of a high schooler named Mary Sue Bradford--the house of her out-of-town parents, I should clarify. I didn't even want to go, having just broken up with Renice that week--my first girlfriend ever--but Amelia insisted. That breakup sucked for me because it came out of the blue. With guys in high school there was some warning--either that, or I was the one to initiate the break up--so I knew what was coming. I was a perceptive girl, at least I thought, and it surprised me and saddened me that I had read the situation so wrong with Renice.

Why did it hit me so hard? Being a first year student at LSU it was my chance to try something new, which in my case was to do something I'd wanted to try for a while: explore a relationship with a girl. And a black southern girl at that, which I'll admit had an exotic appeal I suppose for a suburban white girl from the country's heartland. So I threw myself into it and actually fell in love with this girl. At least I thought. Everything seemed so cool--I loved spending time together and we were starting to fool around, even, which was new for me, to do that with a girl, I mean.

Then she ghosted me for the whole weekend and it wasn't until I showed up at her dorm room mid-week and ambushed her face-to-face that I got any kind of resolution. Not that what she said was very satisfying. I still wonder if it was something with her friends, if I didn't fit in and embarrassed her, or if it was simply physical--that I didn't have the kind of classic curvy figure that she wanted--but I'll probably never know. She didn't have the guts to tell me honestly, and that sucked.

Anyway, the only reason Renice matters to this story is that it put me in a funk that whole week. I was really down about myself, about going to college, my prospects, my classes, everything. At Mary Sue's party with Amelia's always-optimistic urging I gave it a half-assed effort to try to mix in and have some fun, and there was a brief spark with a guy named Arjun who was pretty cute.

I thought he and I were going to flirt--and maybe even fool around that night at the party or perhaps that he would take me away somewhere after. They were playing the game where the guy and girl go into the pantry by themselves and close the door and I let myself imagine what that was going to be like, how to get a kiss and sneak a feel under his shirt. It looked like he worked out a lot and I love the muscles on shoulders and pecs in particular. So things were looking up.

But then this girl with big tits sits down in between us at the table and starts gushing and giggling like a stupid slut--laying her hands all over him and laughing way too hard at his jokes--and of course the fucker goes absolutely apeshit gaga over her and he asks her to the pantry when his turn comes up.

Okay, I shouldn't call him a fucker. That's unfair. He's a guy and allowed to do what he wants and fuck whoever he wants. Guys have needs too and if this guy wanted a silly, big-titted girl to be an imbecile for him then he had that right, without me putting him down as a human being. But I was so tired of being the girl left out--the one the guys would talk to but not want to have a relationship with or even get down and dirty with. I don't have the ass and sure as hell don't have the tits but I do have sexual needs and it sucked not being able to make a connection.

There were some other cute guys I'd seen at the party but I wasn't having luck making progress with them, either. The guy playing the bartender in the kitchen was a handsome jock type of guy, from one of LSU frats, Amelia said, and then there was a younger guy named Jake who caught my attention. Beautiful sweet face and he had the pecs I wanted and a body that killed it; also he looked like a nice guy. I didn't even know who he was until a girl told me he was Mary Sue's boyfriend, which was another suckage for me.

That was it, and I was going to leave because I had enough with this striking out with the boys. And Renice had killed my interest in girls for the moment. But for some reason I lingered to watch this game that was starting in the main room. An energetic girl lined up all the guys and I took a long look at all of them. That cute guy was there at the end of the line! And looking nervous, too. Mary Sue walked away from him and it didn't seem that their last interaction had been friendly, so I was drawn to him right then in a long-shot chance. Something in me knew it might be wrong, but I figured getting to know him couldn't hurt. So I stepped up.

"Are you going to play the game?" I asked him.

He seemed surprised at my interest, looking like a lost puppy after Mary Sue left him. He stared at me, silent, thinking.

"The game," I said again, pointing up to the whole line of guys who were bending over to disrobe. I raised my eyebrows in an attempt to flirt. "Are you gonna take off your pants?"

"Oh," he said, confused. "I don't want to play. But I'm supposed to."

"Mary Sue's your girlfriend, right? The girl whose house this is?"

"Yes."

"Why'd she leave you here?"

"I don't know. She told me I had to play the game."

I was puzzled at the way he phrased this. Like she was the boss of him.

"Well, look, I don't know what that means, but I'd like it if you played." I smiled encouragement and leaned in to add, "I think you're good looking--I would enjoy watching. Do you think she'd mind?"

We both looked up at the rest of the guys. Jake was the only one of the whole bunch of them who hadn't stripped down to his undies. Nobody except me seemed to have noticed, though, especially since he was at the end of the line and trying to disappear into the hallway with his tail between his legs.

"No, she won't mind. She'll get mad if I don't play."

"Really?"

"Yeah."

"But look. She's up there."

"I know. But we, uh... it's complicated." I didn't know what to make of that. "We had a fight." That was easier to understand.

"You're Jack, right?"

"Jake."

"Jake. Got it--sorry."

"It's okay. What's your name?"

"Sorry, I should have said already. I'm kind of a klutz sometimes." My face reddened. This guy was really cute and it was throwing me off. And the way he was talking, it made me like him even more--he seemed like a genuinely nice guy. It also made me not like Mary Sue. What kind of girlfriend leaves her guy and insists that he play some embarrassing game by himself? Even if they had a fight. "I'm Shannon."

The girl running the game stopped by and after eyeballing Jake too long gave me a towel that I was supposed to tie around his waist and then pull his pants off underneath. He looked like he was going to die when he saw that's what he had to do. He wanted out of there so bad.

"Is this too weird, or do you want to do it?" I asked, honestly not knowing what he would decide. His face showed the strain.

"No, I gotta do it or I'll be in trouble." He seemed in distress. He must be shy even though he was so good looking, but I didn't understand why that would be. Shouldn't good looking people love to play these strip games so they can show off? At least that's what I always imagined. But he looked vulnerable. "Look, can I ask you to be my friend here?"

I was confused. "Sure, of course. Anything."

"Don't be surprised, okay? What I'm wearing isn't... isn't normal. Can you keep it a secret?"

"Sure." I had no idea what he meant by that but I tied the towel like I was supposed to and unbuttoned his jeans under it. That was kinda hot and I looked up at him, smiling. I was happy because I finally got to flirt with a guy tonight, even if it was part of a game and not really due to my own attractiveness. In consideration of his modesty I avoided looking directly at him as I pulled the jeans down over his ass and down to his ankles. Then I went to pull down his underwear and that was the "aha" moment, when it all started to make sense--

He was wearing panties. Women's panties. I couldn't see because it was all under the towel still, but the outline of the cut was clear and I could feel the lace and everything. Oh shit. This guy is a cross-dresser. I get to flirt with a hot guy at the party finally and he's not even into girls; of all the luck. Maybe this is why he and Mary Sue had the fight--he indulged himself and then his secret was unveiled to her and she was pissed. But I tried not to form any judgment until I got all the facts. It didn't add up yet.

He had asked me to keep a tight lid on it so I looked around to see who was watching us. The coast was clear. "Okay," I said softly, not pulling them out in the open yet, my hands still on his waist under the towel. "Should I take them off?"

He nodded. I quickly pulled them down and off his legs, trying to hide them with the jeans in a wad of fabric. My eyes went wide as I saw they were bright pink.

"Jake!" I mock-scolded and cracked a smile, shaking my head. I thought I might get a lighthearted smile back from him now that I was in on his secret--being his co-conspirator and all--but he wasn't having fun. None at all. Beads of sweat were forming on his brow. "What? It's okay. Nobody saw," I added in a whisper to his ear.

We both listened while the rest of the game was explained. I was supposed to get under the towel and start feeling up his dick. Holy shit. I had never played a game like this before. I asked him again if this was okay and he nodded vaguely, but the worried expression hadn't left him.

When I felt under there the other shoe dropped, because then I realized he was wearing something else, some device that strapped around his waist real tight and pinned down his dick. It was part of his cross-dressing I guess? To make him feel like a woman? I didn't get it but I was struggling to reconcile this hot guy and what seemed like him flirting with me with this weird thing he was wearing.

So I just patted my hands around his thighs and faked that I was playing the game. Up the line I saw the whole bunch of girls fooling around with their guys, getting their dicks to rise up under the towel--giggling and making hoots and calls about it--and even Mary Sue was up there too working under the towel of a huge guy that had already gotten a large erection. Had she left Jake because he was dressing like a woman? Did Jake drive her away? Was he the asshole in this? But he seemed so sweet, so I still didn't understand.

Jake's towel hadn't budged one iota upwards, of course, even with me under there sort of touching him, because this device was trapping his dick in there super tight. I assumed he had a dick in there, if he wasn't trans. But that wouldn't make sense either because he was built so firmly like a solid man. Could hormone therapy do all that? I didn't think so. And that wouldn't explain his balls, anyway. The dude had seriously big balls. They felt real and authentic and I'm sure hormone therapy wouldn't do that!

I faked it for a while longer--trying to cover his towel from the view of surrounding people so that he wouldn't be found out--and the lights went out saving us. Then the towels came off and dicks started going into girls' mouths up the line. Wow--this game kept getting into more than I expected. I stood up from kneeling at his waist and tried to talk to him in the noise.

"Hey, you did it," I said happily to him, looking at the people in our immediate area. "Nobody saw anything."

"We did it. Thank you." His relief was noticeable. He was still almost naked in a crowd of people with only a small towel covering him, though, so I don't think he was entirely relaxed yet. But a peace had come over him for the moment and his eyes had moistened up. "Really, Shannon. This means a lot to me."

"Sure," I said again for like, what, the fifth time? Couldn't I say anything more original? I wanted the chance to learn more about him, even with these unexplained things, and for him to learn about me.

"Can I ask--" I started, eager to have a real talk with him, but Mary Sue interrupted us. She had her new big man in tow, led by the hand, and he was entirely naked except for the towel held loosely over his groin with one of his big paws. He didn't seem overly worried about covering up. It was an impressive sight, so much muscle and flesh right there in front of us, and this head of flowing curly black hair. Jake had his shirt on still and was a ripped athlete, yet this new guy was bigger than him. Dominated him, even.

"Jake! You played," she said. "Good. This is Kaipo--"

"Just call me Kai," he said in a deep voice, enthusiastically, reaching a hand out to the high schooler, who was impressed and maybe even intimidated by the big man.

Jake shook his hand in appreciation at Kai's girth and asked, "You a Tiger?"

"Starting outside linebacker, baby! You play?"

"Yeah. Quarterback. For the high school, I mean," he added, looking down at the floor after he said it. I didn't know the pecking order for football jocks but I guess Jake didn't think he stacked up much compared to the college guy, at least based on his reaction. Jake seemed very eager to defer to the more mature and larger man. It was like those things you read about the alpha and beta males. Jake just slipped right into beta male mode, which was strange for me because before Kai stepped up he was playing the role of the strong guy.

"Good, brah," Kai said. Was that a patronizing edge to his voice? Talking down to my Jake? "If you work hard maybe you get to play some college ball, somewhere." Jake didn't seem to notice Kai's tone; if anything he seemed oblivious and honored to have the attention of the college athlete. Maybe he really was a beta male and didn't even notice the way Kai treated him.

Mary Sue interrupted the two guys, "Kai was my partner for this game. And--wait, who is your new friend here, Jake? Introduce us."

Jake seemed back on full alert, pins and needles. Whatever relaxation he started to show with me was now long gone with the arrival of his girlfriend. When he spoke it was halting. "Mary Sue... this is Shannon."

"Hi," I said, unsure where this was going. She eyed me. I had talked to her briefly earlier in the evening and she seemed nice enough but there was more steel showing now. I felt there were things going on between these three that I didn't understand.

"So you played the game with Jake?" Mary Sue continued. "That must have been interesting."

"Well, yes," I said, not wanting to give too much away in case the women's clothes thing was Jake's secret even from his girlfriend. But Mary Sue must have known what he was wearing to her party, though?

"I'm sorry to interrupt you guys, and it was nice to meet you... Shannon, but I need to take Jake. He did something wrong earlier and he has--well, some consequences coming to him." She turned to her boyfriend. "Say goodbye to your new friend, Jake. Come with Kai and me."

"Wait," I said naively, stopping them, not wanting my time with Jake to be over. I didn't think about what I might be getting myself into. "Can I stay with Jake?"

"He has to come with us," Mary Sue said. "Jake. Now, Jake!"

"Yes, ma'am."

Kai started laughing at him. "You her bitch, huh?" He said it too loudly. "She says you go there, you just go there. Tail between your fucking legs. Ha ha. Fuck..." Some people standing near us heard the big football linebacker and started listening.

"I want to go," I pleaded my case one last time to Mary Sue. She leaned towards me.

"Jake obeys me," she said. It wasn't mean or angry or anything, it was just matter of fact. "If you come with us, you'll have to obey me too."

"Okay..." I said, unsure what this really meant but wanting to stay with Jake. Looking at the group of them, the hulking and horny Kai and Mary Sue with her controlling attitude, I had sudden second thoughts as I turned to follow them anyway. Did I really want to do this?

Jake caught my eye as the other two turned away from us. He mouthed quietly, "Are you sure you want to do this?"

"Do you want me to?" I mouthed back.

He hesitated, then nodded. "Yeah," he whispered, with conviction. "Yeah, I do."

"Okay then." I smiled. "I'm with you."

Mary Sue led us down the hallway to the last big bedroom, pulling out a key to open the door. It must have been the parents' master that she kept locked up during the party. I don't blame her for that; there were probably stains and spilled beer and all kinds of shit anywhere in the house that the partiers could roam and fuck around.

It was quiet in the big bedroom and she shut the door behind us. The music of the party faded and it seemed like we all took a deep breath to relax. At least I did. But now what was going to happen, I wondered. My heart was racing a hundred times a minute.

"Jake. Shannon. Stand here by the bed," Mary Sue barked out and we obeyed. My bonding with Jake was growing now--not only did we have a shared secret of his unusual undergarments but we were also now brothers in arms in our submission to Mary Sue.

"Off with the towel, Jake. Let's see it." Jake was not happy but peeled off the towel and stood bottomless before us.

"Brah! The fuck!" exclaimed Kai. The enormous man started laughing uproariously and jumping around the room, pointing at Jake's crotch. "The fuck is that? Oh my fucking God! Your cock is locked up under that thing? You got a chastity on you!"

Somewhere on the trip from the living room to the bedroom Kai had lost his towel exposing a half-erect, enormous horse dick, which was jumping around along with him flopping this way and that, but he didn't notice. He was very comfortable being naked, it seemed. As he settled down, still laughing, I could see that the big cock was thick and dark and listed to one side along his inner thigh. Kai was still staring at Jake's ridiculous binding with amazement.

I saw now what it was Jake was wearing. One of those chastity belt things with the black straps and a cover over his penis area. It was funny how his testicles stuck out below. The whole thing didn't fit him well at all and I remained confused what was going on.

"Shannon," said Mary Sue, pointing to Jake's crotch. "I can explain now. This is part of Jake's punishment. I put the chastity on him tonight for something he did."

"You put it on him?"

"Yes, and you will call me ma'am, please."

"Yes, ma'am." It was easy for me to assume a deferential attitude with her. Something about Mary Sue fit the role of a dominatrix well--I wondered if that was the right name. I was starting to get an idea of what Jake had gotten himself into. I hoped it was his choice for his own sexual pleasure and not for some blackmail or money or something. It didn't seem like it would be. Mary Sue seemed like an ordinary girl for the most part and talking to her at the party before this she seemed a nice enough person--this thing going on here was just a roleplay. I hoped. But maybe it wasn't?

I considered bailing out after seeing this much of the story but part of me wanted to stay for Jake's sake and another part just out of curiosity to see what was going to happen next. I could always leave later, was my thought process. My spidey senses weren't telling me that I was in any danger here, even though Kai looked like he could rip any of us apart, including Jake, anytime he wanted to.

"Shannon," Mary Sue continued, saying directly, "I'm in the mood to get fucked tonight, and as you can see for yourself Jake isn't able to do it. That's why I brought Kai back here."