Fuck Around and Find Out - Pt. 02

You would think that finding out that I had won a scholarship to Cornell would be the highlight of my month, the most memorable moment of my senior year. But at the time, it was only the second most life-altering event within 24 hours.

Number one was losing my virginity.

By getting fucked in the ass.

Because, yeah, I'm a guy.

It all happened within a week. I didn't think of myself as gay; I still didn't, afterwards. But I had allowed myself to get into a cycle of teasing with Luke Wallace, the all-state defensive tackle who liked to make outrageous boasts about how many virgins he had deflowered, including his male rivals who he "sissified" with his big cock.

.

After he had done it to me on a futon in a darkened theater prop storage room, we never spoke of it again. The only acknowledgment was that he was now calling me "Marty," in public, a play on my last name. Or, in the private joke in my head, "Marti," with a little heart above the "i." Because he had boasted that his cock was going to turn my ass into a pussy, and me into a girl. It was bullshit, of course, but erotic bullshit.

And now everyone was calling me Marty.

I didn't expect it to ever happen again. That wasn't Luke's style, I knew now. Luke was all about the conquest, and now that I was in his trophy case, he had lost interest. And, oddly enough, that was okay with me.

The thing was, the experience was mind-blowing. After the initial pain of being stretched open, I had found the sensation of being filled up to have been overwhelming and exhilarating. I hadn't had an orgasm, but Luke's hard appendage inside me had rhythmically massaged some part of me that I didn't know existed, and made me feel like I was on the verge of one for several straight minutes.

So, yeah, I had liked it.

But the other thing was that the whole time, I felt shame and regret and humiliation. I felt used, like this object to be wrapped around a cock and thrust into and cum into, and then thrown away, like a tube sock or a pair of sister's panties. I was horrified by my visions of other people seeing me and finding out, thinking less of me, seeing me as pathetic. And all of those feelings were all jumbled up with the memory of a five-minute near-orgasm.

I wanted to do it again.

So, I started spending my last few weeks of high school imagining, contemplating how, and with whom, I might repeat the experience.

Oh, I didn't lose interest in girls. I hadn't completely changed teams. But I had already come to the conclusion that I wasn't going to get into a romantic relationship with anyone around here in the last three or four months before I left for college. And of course, for me and for the only girls I was interested in, romance or relationship was a prerequisite for sex.

But that just left more mental space for me to think about those people for whom sex had nothing to do with romance. Guys.

I took my yearbook to bed and tried to imagine which other boys might be candidates for the kind of illicit, forbidden, one-off encounter that I had had with Luke. Of course, I started with the other jocks. They would be the most likely to have that primal, hyper-masculine ethic of dominance and submission that got me on Luke Wallace's radar screen.

I recognized what traits made guys physically attractive to women, and used that as a starting point. I considered the obvious candidates. Jim, the quarterback; not tall, but with ice blue eyes and a sparkling smile. Or Monte, his lithe, sleek wide receiver. I considered other sports. I looked through the pictures of the wrestling team... short, stocky guys with menacing stares; two thirds of them, of course, carrying even less than my own 145 pounds. The idea of being dominated by a 5'4" sophomore gave me a strange quiver; but other than that, I realized that... I wasn't getting *aroused* by the notion of seeing any of these guys naked, or being naked in front of them.

I thought about what had aroused me in the days leading up to my submission to Luke.

And, shit.

I remembered how Luke had teased me about not having a prom date, and had jokingly offered to "set me up" with one of the Plug Uglies, the big lumbering dudes of the football team's offensive line. How that night, I had mentally run down the list, and with a strange, compelling pit growing in my stomach, locked in on the right tackle, Truck. Mack McGivens, but known to everyone as Mack Truck.

Truck was in a couple more of my overlapping social circles. Like Luke, he was a decent student, another one of the dozen or so of us in the few college prep classes at our high school. Like me, he played sports to be a part of the in crowd, not because he was any good. Although I'm not sure he realized it.

And because he was 6'4" and big, I think he modeled himself after Luke. But whereas Luke had kind of a good-natured self-awareness of his "act," Truck seemed deadly serious. He was loud and overbearing in groups, and insisted on trying to make jokes that didn't land, that just made me wince and look the other way.

In smaller groups we actually got along okay. Truck and my non-athlete friend Brian and I liked the same rock music, and we had gone to some concerts together. He still tried to act as if he was the leader, the alpha of our little group, and he still insisted on trying to make every line a joke, but he was okay.

The other thing we had in common was that we didn't date. I didn't date because I was too shy, afraid of being rejected even though in retrospect I shouldn't have been. Truck didn't date because he had learned about rejection the hard way.

Because Truck was the poster boy for the Plug Uglies. His 240 pounds had already started to settle around his middle. He had deep-set eyes, one of them wandering, under a vaguely Cro-Magnon brow and an unruly mop of straw-colored hair. He had the bulbous nose of a sixty-year-old drunk, and crooked lips. And he was cursed with far more than his share of acne.

And as I looked at his picture in the yearbook in my bed that night, I realized that my penis had grown almost painfully stiff. Thinking about getting fucked by Truck.

Damn it, it was all Luke's fault. He had planted this idea in my head, just as deeply and irrevocably as he had planted his cock in my rectum.

Luke had conquered me, and enslaved me. And now that he owned me, it was his right to sell or give me to someone else. And whether the guy knew it yet or not, that someone was Truck. And as a conquered, enslaved spoil of Luke's "war" on his perceived rivals, it was my obligation to submit, to Luke and to my new master. The Bible said so! Right there in Ephesians: "Slaves, obey your masters..."

I realized that Luke had not only taught me to crave the feeling of a hard cock moving in and out of body again. He had conditioned me to associate that desire with being submissive, overpowered, and humiliated. And I couldn't think of anything more humiliating than offering my ass up to Truck McGivens.

Now I just had to figure out how to make it happen.

****

It took a while. Prom came and went, and so did graduation. I went to prom with Karen Coleman, a nice girl to whom I was not particularly attracted, because she asked me, and I was terrible at saying no thank you. Truck didn't go the prom, of course. Unlike me, no one asked him.

I felt badly for him. I was afraid of rejection because I had been told I was "cute" instead of "ruggedly handsome." Truck was downright unattractive.

I overheard one of the cheerleaders calling him "pizza face," which I found cruel, and also a little repulsive. Especially since I had been fantasizing about being cheek-to-cheek with him, doing a horizontal dance in his back seat.

He was smart enough, and he could be funny if he would just stop constantly trying so hard. Eh, but who was I kidding? He was a blowhard. We shared some friends and some tastes in music, or I wouldn't spend any time around him at all. I felt like I was trying to rationalize my irrational obsession with being dominated and humiliated sexually.

After graduation, my daily opportunities to be distracted by multiple pretty girls evaporated. I knew the restaurants where some of them worked, but you can only eat so much pie. That was okay. I was heading into my last summer in this small town, perhaps ever. I was content to save some money at my part-time job, play frisbee, and hang out with my buddies. Including listening to music with Brian and Truck. Which I found myself choosing to do more and more often.

***

That's how I ended up in my family room one late afternoon with the two of them. And, when Brian got up and explained that he had plans that evening, alone with Truck.

We were listening to ZZ Top. He was oblivious to what was going through my mind.

Then the song "Pearl Necklace" came on. The band's naughty homage to blow jobs and titty-fucking. Truck sang along. Badly, and loudly.

I just grinned and tried not to look annoyed.

"So," he leered at me, "Did you give Karen Coleman one of those after the prom?"

"Truck," I chided him. I wasn't going to answer that, even though the answer was "no." Or maybe because the answer was "no." Actually, I wasn't opposed in principle to the idea of Karen stroking me until I spurted strings of personalized organic jewelry over her not-insubstantial cleavage. But I had avoided doing anything that she might interpret as intimacy. I was leaving town in a few weeks.

But Truck didn't need to know any of that. And he appeared to be chastened by my silence.

"Did you have a good time, though?" he asked, suddenly seeming serious. "At the prom, in general, I mean."

"Eh," I said. "It was okay. Over-rated."

"Still," he mused. "One of those things everyone talks about."

"You didn't miss much."

"Hrmn," he said, looking away. Being more honest and vulnerable than I had ever seen him. "No one was going to go to the prom with me anyway."

I looked at him and for the first time felt something other than, or in addition to, my twisted forbidden desire to submit to him sexually. I still hadn't figured out how I was ever going to approach this, and this scenario hadn't been on my radar screen. But before I could weigh the wisdom of it, I heard myself saying, "I would."

He looked at me in confusion.

"I mean, if I was a girl."

He furrowed his brow, and stared at me. Into my eyes. Then looked away.

"Mack," I continued, free-lancing. "Just wait till you get to college. You'll meet girls who are more interested in... intelligence and character."

Mack looked off to his right. He was reasonably intelligent. But not enough to realize he was being played.

"Too bad you're not a girl."

I swallowed hard. I hadn't planned this. Fuck, what was I doing?

"I could be."

He cleared his throat and looked back at me. "Huh. You'd make a ... good girl."

It was my turn to blush. And, helplessly, go fishing for a compliment.

"What... do you mean?"

He lowered his eyes. "I mean..."

"You mean I'm smart and funny and not shallow?" I offered, my head spinning with what I was doing.

"Huh. Yeah." He was looking at my legs, extending down from my running shorts, crossed at the knees instead of the ankles. He couldn't have missed my erection.

"We could pretend," I found myself saying in a hoarse whisper.

He looked at me with apparent suspicion. But it didn't feel like the suspicion of a guy who was freaked out by being approached for a same-sex encounter. It felt like the suspicion of someone who thought I was pulling his leg. In spite of the obvious hard-on in my pants.

"We could, huh?" he finally muttered.

I just shrugged. Being coy was the only card I knew how to play.

He cleared his throat and looked at me with his eyes narrowed under his prominent brow. "You need to be careful, Marty," he finally said. "Someone might take you seriously."

Yeah, I know, I thought to myself. Someone already has. But I just said, "Hmmm."

He read my non-denial accurately. As I said, Truck was awkward, but he wasn't dumb. I could almost hear the wheels spinning in his head. Despite the pounding in my own chest.

He looked around the room, and then put his hands on his knees and stood up. "I need to get going, too," he announced. Oh, shit. I had outed myself and got rejected.

"But, um, Marty?" he ventured. "Uh... you want to hang out at my house on Friday night? I got the new Molly Hatchet album."

Molly Hatchet? I hated Molly Hatchet. But I nodded in agreement. "Yeah, that sounds... good."

"And, uh... my parents are going to be out of town."

Uh huh. Okay. So this was going to happen. I figured neither one of us were going to invite Brian to join us to listen to albums.

"So, you know. If you want to... have a little prom night..."

***

I had two days. The clock was ticking. I needed to get out and do some of the shopping that I had been thinking about but afraid to do. I called in sick at work, and told my mom it was a day off, and I was going to drive into the city to do some back-to-school shopping. She thought that was a good idea. So much for a mother's intuition.

Rockford was about an hour away, no big deal; and I wasn't worried about running into anyone I knew there.

I started out at a large Goodwill store, gradually working up the nerve to start browsing through the women's section, certain that people were watching me with curiosity or disdain. Hoping no one was going to say anything. Or call the cops.

Once I realized that no one was paying any attention to me, I allowed myself to linger between the rows. I found a rack of what passed for prom dresses. Of course, I couldn't try anything on. But I had a rough idea that if I was a medium in men's clothes, then I would need either a large or an extra-large in young women's.

I picked out a couple of dresses that didn't have too much of a plunging neckline, that wouldn't highlight my lack of cleavage. They were both mid-length, probably cut above the knee, which I figured might only come down mid-thigh for me. Which I didn't mind at all.

Draping them over one arm, I moved over to the shoes. I had no experience in walking in heels, but I didn't figure I would be doing much dancing. At least not vertically, I thought with a nauseating thrill. After a couple of minutes, I found a pair of cream-colored pumps with low heels in a women's size eleven. Probably something that someone's grandma wore to church. They would have to do.

I finally worked up the nerve to go check out. There was a middle-aged woman behind the cash register. She made no comment as she rang me up.

Then I went and found a Beauty Supply store. I picked out some of the cheapest cosmetics I could find. Lipstick, blush, eye liner and shadow. I didn't know what "foundation" was. It took me a while longer to get comfortable looking at the cheap wigs; even longer to work up the nerve to quickly put a couple on for the three seconds I let myself look in the mirror. They looked stupid.

I hadn't cut my hair since Christmas, and I had spent enough time in the past few weeks looking in the mirror after a shower, before styling it with a blow-dryer (hoping to look like Jimmy Page), that I had decided that it could pass for a sassy little shag if I just let it air-dry. So I left the wigs and checked out.

I was on a roll now, so I went to the mall and sought out a higher-end department store, and walked right into the lingerie section, telling myself that I was obviously a stud who was shopping for a sexy gift for his hot girlfriend.

It took a while, but I finally found an A-cup bra with a 38-inch chest measurement. Then I got the matching panties. And a garter belt, and a pair of nylon stockings. All in ivory, just like in my fantasy.

That night, after everyone else had gone to bed, I slipped into the bathroom and began experimenting with make-up. I had no idea what I was doing, and everything I tried looked terrible. I didn't want to look like a clown. Eventually, just like with my hair, I decided to just go with lipstick and let my clear complexion and my slightly androgynous features speak for themselves.

Tomorrow I would find out if it worked.

***

I knocked on Truck's front door, dressed in my normal shorts and t-shirt, a backpack slung over my back. When he opened the door, the very first thing that registered with me was the overwhelming scent of Brut, or some other overpowering men's cologne. He must have bathed in it.

Before dressing himself in a leopard-print rayon shirt, and the black slacks of what was probably a leisure suit. I couldn't help grinning a bit. Okay, he was getting into this, too.

"Hey, Rob," he said, quietly, holding the door open for me. I stepped inside.

"Call me Marti," I replied, mentally replacing the assumed "y" with a lower-case "i." With a heart over it.

"Give me a minute?" I asked, beginning the familiar path toward his bathroom. I didn't trust myself to not fuck this up with "So, we're really doing this?"

I got into the bathroom, stripped out of my clothes, and ran some water in the sink to get my hair wet and scrunch it up into what I hoped was a brunette version of a Goldie Hawn shag.

Then I dressed myself in the outfit I had assembled, and finally, applied some pink lipstick. Then I stepped into the low heels, and began to walk, unsteadily, but consciously with a provocative heel-toe, heel-toe strut, back down the hallway.

Mack was fidgeting on the sofa. When he saw me, he stood up, looking both uncertain and... huge.

"Jesus, Rob," he said.

"Marti," I reminded him.

"Marty," he replied. "Damn, you look..."

I probably blushed, and did an awkward 360, letting him see the plunging back of my gold lame' prom dress.

"So, you're all dressed up for prom," he ventured. "You... want to dance?"

I wasn't sure what he had in mind, or what music he could possibly put on. I definitely didn't want to fast dance in these heels; not that I felt like I could move like a girl anyway. But I nodded, and he went over to the stereo, and pulled out the Bad Company Straight Shooter album, and dropped the needle at the start of "Feel Like Makin' Love."

Oh. Well. Huh. I had to admit I was impressed. At least for the first couple of minutes, this ballad wouldn't be a bad song for me to bury my face in his shoulder, and let him pretend he was at the actual prom.

I waded into his cloud of cologne and his waiting arms, which he closed around me once I got close enough. Good song choice or not, I was feeling awkward, and I was sure he was, too. So the easiest thing to do was to break off eye contact, rest my forehead on his chin, drape my wrists over his shoulders, and let his hands wander over my sides and my bare back as we swayed in a slow circle.

For two minutes. Then the song got to the chorus, and the guitar's power chords burst out of the speakers. And Truck began to reflexively thrust his hips into my stomach in time with the music. And I could feel his arousal.

I had no experience with judging cock size by feel with my belly. But I could tell he was hard.

Fortunately, the bridge returned to the more languorous pace, and we could continue our clumsy approximation of a slow dance. Only during the rave-up at the end did I begin to feel silly. When the song ended, he pulled away from me.

"You want something to drink?" he asked.

"Sure," I replied. Again, I didn't know what he had in mind. I wasn't much of a drinker, but I figured I could nurse whatever he came up with. It turned out that he had an ice bucket and a couple of diet cokes on the shelf of the china cabinet. He handed me my glass, and then he sat down on the sofa. One of those crushed velour numbers with an autumnal floral pattern of oranges, yellows, and browns.

I wasn't sure what he expected next. Jesus, I didn't want to make out with him. Then I noticed the towel on the seat beside him. Huh. He really had been thinking ahead, and we were on the same page.