Crosstraining Ch. 01

I don't really know where to start. It all happened a couple of weeks after Claire and I broke up, and I was still feeling pretty jagged from that. But it also started a few months before that when Claire and I were running down through the park close to my apartment and she said "Wow, those black guys playing basketball look tasty!" Okay, maybe the breakup and her talking about other guys like that were connected too, but I mean when things with me crossdressing started. And with, you know, being the girl.

I can't say clearly what made me do it. I was sitting there in my apartment staring at something stupid on the TV and feeling hopeless. Somehow the idea crossed my mind of those guys playing basketball, and that made me think of Claire, and the look on her face when she watched them. All of that definitely didn't make me feel any better. That word "tasty" that she had used stuck with me, seeming so strange, such a weird word to use. And then somehow I wandered into my bedroom and opened the drawer of my dresser with Claire's stuff. I just stared for a few minutes. It was kind of a screwy assortment of stuff, from different times she had left things. Most of it was running stuff, her sports bras and shorts and tops. We'd run around my place, and afterwards a lot of the time we'd just throw her stuff in the wash. So that made me think about the sex that came next, at least until near the end, and that made me feel even worse. She'd been amazing in a lot of ways, but I really hadn't measured up, and now I was regretting not doing everything I could to keep her happy.

So I found myself thinking all that, and staring at the stuff she'd left behind, that she never even bothered to pick up. For the first few days I thought it would be an excuse to get back together, that it would give me a chance to talk to her, but time went by without her responding to my texts or voicemail. And her stuff just sat there in the drawer.

I reached out without even thinking about it and touched one of the bras. It was silky, lacy, bright pink, such an amazing feeling brushing my hand across it. I picked it up and touched it to my face, and it felt so good, but then I realized what I'd just done and dropped it back into the drawer like it was on fire. What kind of weird freak was I? How could I be so creepy? But then again, it didn't seem like she wanted the stuff back ever, so did it even matter?

And I didn't close the drawer. I stood there staring at the things in it. It felt wrong to pick up that bright pink bra again, so somehow my brain reasoned that I should pick up another one instead. And then I had a black sports bra in my hands, and I don't know why, but suddenly I was holding it up in front of me to my chest. It happened with no planning it. But somehow it felt comforting. I'd honestly never thought about wearing women's clothes before, not even a little. But in that moment I needed to try, to see what it felt like.

I pulled my t-shirt off and tried to pull the bra on. I almost wrenched my arm out of its socket. It took a few tries before I got things lined up and more slid it straight down over my head and arms all together instead of trying one arm at a time. Somehow the physical puzzle of how to get it on occupied my brain enough that I didn't stop doing something I would have said was crazy just a few minutes before. And then I was wearing it, and staring at myself in the mirror, and shocked that it looked HOT on me. It had a little bit of some kind of padding built into the cups, so even though I had nothing at all there, it gave the impression of some nice little breasts. I mean, definitely emphasis on the little part, but still. I looked like a flat girl, not a boy. And even if I was on the short side for a guy, I was a little tall for a girl, so the lean kinda flat look worked, sort of like a fashion model or something.

And I couldn't stop there. I found myself in the bathroom pulling one of her lipsticks out of the medicine cabinet and trying it on. I didn't pay attention to which one I grabbed, it was like I was in a dream, but when I stared into the mirror and tried putting it on I realized it was the bright red one, the special one Claire called "cocksucker red," which took my thoughts down a whole other track for a few seconds, but then my attention snapped back to the mirror and damn, it's not easy to make it look right, so I grabbed kleenex and wiped off some stray parts and tried again. This was another part where the challenge of it occupied my brain so much that I didn't really think about what I was doing. Or at least it seemed that way, or I told myself that, or something.

The hair was the easiest part. My haircut was another choice made by Claire, what she described as the boy version of a girl with a boy cut. I know that's confusing, but the point is that she'd tried some of her hair products in it the day after I got it cut, something about maximum volume, and it made it look exactly like a girl with short hair instead of a guy. That bottle was still right there in the medicine cabinet, so in maybe sixty seconds my hair looked like that again.

I had a moment of thinking about mascara, because that was right there too, but girls had always told me they were jealous of my eyelashes, that it wasn't fair a boy should have them so long, so I decided it wasn't needed.

So I stared at the mirror, taking the whole picture in instead of just the one piece at a time that I'd been focusing on. Holy shit. It was a girl looking back at me. I smiled, sort of the instinctive bashful smile when you realize a really cute girl is looking at you, but it was me, and the smile with those luscious red lips was totally fixating. Suddenly looking at the cocksucker red lips, I thought about them wrapping around a cock. But they were my lips, instead of it being my cock, and it was really unsettling. For a minute I almost pulled the bra off, I was going to wipe the lipstick off and pretend it never happened. But then I realized how I knew it wasn't my cock, apart from the impossible part where it was my lips, and that's because the cock was black. I realized I had somehow imagined my lips, painted their slutty red color, wrapping around a big black cock. I don't know where the idea came from. I'd honestly never thought anything like that before. But hey, cocksucker red somehow always did something to me, always riveted me, and the difference was this time the lips were mine.

So trying to shake off the image of my red lips wrapped around a big stiff black cock, which suddenly was taking extra developments like kissing up and down the shaft and flicking my tongue across the tip, I spun out of the bathroom and back into the bedroom. Somehow I was thinking if I got away from the mirror I'd get away from the thoughts it had put in my head. And then I was back in front of the dresser, and staring down into the drawer, and there were the running shorts and the cute pink top that went with them, the shorts pink trim but black because it was "slimming" and I was pulling the top on because it might distract me from the image of that hard black cock with my tongue flicking across it, and I did get the distraction I was looking for, but it was from the shorts. I picked them up, but it seemed wrong to put girl shorts on over guy underwear. Which then had me thinking that if that was what seemed wrong to me about all this then I'd really lost perspective, but then I was grabbing pink underwear from her drawer and pulling mine off. Hers slid on easily, but felt so different, tight and loose in totally different places than what I was used to. I pulled the shorts on and looked at the full-length mirror in the bedroom. I was careful to avoid looking at the lips, having finally shaken those thoughts off, but the rest was amazing. I've never had much hair on my legs, and the cut of the shorts gave me bigger hips -- so much for "slimming" -- so the whole picture really worked. It didn't look like me, so it was like looking at a picture of another person. And that person was really cute, and I found myself smiling at her again, and then realizing I was thinking of her as a her, which was dizzying again.

So instead of looking at myself more, I felt like I needed to do something else, and completing the outfit seemed natural in some weird way. The last piece, the shoes, was also easy. One of my pairs of running shoes had... well... pink laces. It was all from a bet with Claire that I lost, although now thinking about it that doesn't even a little bit explain why I'd left them that way, but I didn't want to think about that. I grabbed them and slid them on, and somehow tying those pink laces felt entirely different than anytime before. This wasn't an embarrassing thing associated with losing a bet; now it was a natural thing, the obvious last element in my cute outfit. The thought came into my head that obviously guys would be staring at my ass instead of the laces in my shoes, but I shook that off and stood up to run back into the bedroom to look at myself in the mirror again. Except "run" wasn't quite it, maybe more pranced or bounced, and that was confusing too, but then I was staring at her in the mirror again, and she was smiling at me again, and I'd forgotten not to look at her lips. Then the image of the lips wrapping around that glistening back cock was back, and this time the cock was thrusting, drawing back and then thrusting forward again, over and over, with me just the passive recipient. I realized my mouth was watering, my tongue moving all of its own accord, and I shook myself away from both the mirror and the image.

So what the hell to do? I didn't want to take it all off, it was too exhilarating now. Staring at the mirror was definitely out of control, so somehow it made sense to me that I had to get away from the mirror and that cute girl smiling at me with those cocksucker red lips. So obviously I could literally run away from that, right?

So then I was out the door of the apartment before I could hesitate. I couldn't believe what I was doing. In the hallway I started actually thinking, not totally rationally but at least thinking about what if one of the other people from the building saw me there. So I rushed straight for the back door, the closest one, away from the parking lot most people come in from.

And of course the back door was on the side toward the park, so without really deciding to I was running along the sidewalk toward the park. The autumn evening air was cool and running felt great -- I'd been moping for a few days and hadn't run, so the movement felt really overdue. The crisp air on my cheeks sort of brought me to my senses, and part of my brain was screaming that I had to go back RIGHT NOW, but then I realized that the cold air had made my nipples stiffen, because I could feel them rubbing against the spandex of the running bra. It was amazing, I'd never thought about nipples being stiff and sensitive, well at least not my nipples, and the sensation was incredibly intense. I was immersed in the feeling, and the rational part of my brain was working on how my same body could feel so different just from putting a different batch of clothing on. That's when I processed that I was running differently too, with my steps just a little shorter and my stride slightly different. It was the guy walking his dog who made it click for me, with his scatter of gray in his businesslike haircut, seeing the way his eyes moved as I ran past, and I realized my ass was moving differently. I glanced back over my shoulder at him and the thrill of seeing him staring right at my butt was electric. I paused and smiled back over my shoulder at his reaction, his sudden guilty jerk of eyes back up, then instant of confusion at my smile, then him smiling back as if something were too good to be true.

And now instead of the rational part screaming to GO BACK, it was GET OUT OF HIS SIGHT, and I upped my pace toward the park. It's a big park, several blocks, with thick trees lining the running path that winds through the upper part. I was running through the woods, marveling at the guy's reaction to me. He thought I was hot too, obviously, just like the reaction I had seeing myself in the mirror. As a guy I'd always thought of myself as very average, but evidently as a girl I could get some real attention. There was a flutter in my stomach at that thought, and then the tickle of nipples against spandex, the novel feeling of panties, and all the sensations were overwhelming me, flooding out thought.

The colors of autumn leaves just starting to change, the crisp air, have always been my favorite season for running. I was relishing it, sort of pushing down the thought of what I was wearing, the word "crossdresser" flitting through my mind but me refusing to notice it. Then I was reaching the point where the trail opens out to a big open space, with a playground and parking lot and... oh yes, and basketball court. My drifting thoughts were instantly jerked back to the immediate situation. To the fact that I was wearing a bra, and running shoes with pink laces, and cute hair, and cocksucker red lipstick, and I was already past the branch in the sidewalk that would take me the other way, so I was going to run right past the basketball court. Past the basketball players.

I'd run past them a hundred times, more than that, and they never reacted. There was usually a full five-on-five game going at this point in the afternoon. When I used to run by with Claire they noticed her, you could tell, but the reaction was subtle. Now it wasn't. Me running by, dressed in her clothes, suddenly one guy snapped his head around, another looked to see what he was looking at, and the guy with the ball tripped and nearly flipped over someone who had been moving a second before but had frozen staring at me. They were all staring at me. Ten guys, big guys, athletic guys, masculine guys, lusting-for-me guys. Their expressions didn't try to hide it at all.

I smiled at them, the shy smile I had shocked myself with in the mirror. One started to whistle at me, but another even taller guy punched at his shoulder with a look that stopped him almost before he had started. I turned my smile fully on my gallant protector and tried to make it smolder a little. The voice in my head was screaming GO but at this point I was loving that I could flout it, and was loving this attention. So instead of GO, I stopped, pausing since right there was the water fountain. Slowly, taking my time, I bent down for a drink. It wasn't until the water hit my lips that I realized I had bent from the waist, my butt out for them to stare at, and they were. I was sideways to them, so I could see the looks on their faces and they could stare at all of me.

I was reveling in it, honestly almost drunk on it, and it was only broken when the tall one stepped forward. Suddenly he was right there in front of me, close enough to touch me, and his physical presence shook me. He towered over me, wearing only shorts, his dark skin shining with sweat and etched with muscle. I shuddered, suddenly again aware of my nipples, of the panties, of my cocksucker red lips. I didn't realize until I looked back up, but I'd just stared at his crotch for a moment, and from his expression it was obvious he'd seen that. Maybe it was longer than a moment. I don't know, time was running funny.

His deep voice startled me when it finally came. It was warm and strong, it made me think about what it would be like to have him hold me in his arms. "Hey beautiful girl, what's your name?" The question seemed to hang in space there between us for an eternity as my head spun. All my new confidence in how guys were seeing me now melted in an instant, struck by fear that if he knew what was between my legs he'd be angry, might hurt me.

"Uh-" finally came out. I couldn't manage more. He raised an eyebrow and reached out a hand, a big black hand that made mine look tiny in comparison. He took mine and held it, and the feeling was overwhelming, like being wrapped up, securely, comfortingly.

"So if you can't say your name, how about we walk for a minute for you to pull it together?" I nodded, even though it seemed like everything had just twisted off the tracks. This huge masculine guy, and I was just going off with him? But I had nodded, and somehow I felt like that was all the choice I had.

After a moment he started walking, continuing along the sidewalk in the direction I had been running, and still holding my hand so it felt totally natural to walk with him. He seemed to understand that I was perfectly compliant, that his strength was totally mastering me. Part of me realized his friends were laughing behind us now as we walked away, joking about me, assuming I was some kind of completed conquest already, but it didn't seem as important as his hand holding mine. He was talking, but my head was spinning so I couldn't really make sense of anything he said. I realized he had just asked "Have you ever been with a black man before?"

What? How could he be saying that? I just met him, I don't know him, there's no way I should be going anywhere with him! But he repeated it, "Have you ever been with a black man before?" and after a moment, watching my face, he said "you can just answer 'yes sir' or 'no sir'."

And somehow that was what it took, and I could talk, finding myself saying "No sir" in a voice that sounded timid in my own ears.

Then, as the sidewalk turned back into the woods along that side, "Have you ever thought about black cock before?"

There was roaring in my ears. I could feel my cheeks blush, the coincidence of this after all my earlier thoughts too much, no way this could be happening, no way I should be going anywhere with him, but I heard myself saying "Yes sir" in the same timid voice.

I realized that somehow instead of holding my hand he now had his arm around my waist. I didn't know when that had happened, how that had happened, but it felt right, and his strength made me tingle. The awareness of my panties was suddenly there again, just as his big hand shifted from my hip to my butt, cupping it gently, firmly. Then I realized he was steering me, turning me toward a patio, and we'd somehow already reached the edge of the park and the expensive apartments along that border. He guided me across the patio, through a sliding glass door, and inside. This couldn't be happening, I didn't know this guy, this strong and confident guy who had his hands on my ass as he pulled me toward him.

"Does the thought of wrapping those beautiful red lips around my big black cock turn you on?" and again my head spinning, this with my earlier thoughts too much. "Yes sir" I heard myself saying, and then he was leaning down and kissing me, his hands holding me to him, and the jolt of realizing his hard cock was pressing against me, another jolt as he broke the kiss and I looked down to see the head of that hard cock sticking up out of the top of his shorts.

Confusion, the voice of what was left of rationality screaming about what happens when he finds you're not a girl, but then he's saying "Are you going to suck my big cock now" and "Yes sir" is what I hear myself answer. He kisses me again, long and slow, his tongue taking control of me completely, his hands holding my ass tight. The rational voice realizes only the fact that he's so much taller than me has kept him from feeling my own cock, which I have suddenly realized is rock hard too, weeks since Claire, but pushing sideways in my panties. He ends the kiss as he lets me drop down to my knees, having promised to suck his cock now.

I have his shorts down and the sight of his beautiful, huge, black cock is magical. If I hadn't already promised, the sight alone would be enough to put me into this trance. But I have not just the sight of this amazing black cock, but also the feel of his strong hands holding the back of my head, and the taste of his mouth in mine. His hands aren't forcing yet, just holding, so it's my promise that leans me forward, that runs my tongue up along the underside of this amazing, beautiful back shaft. I hold this beautiful cock with both hands, bringing the tip down to my lips. I kiss the tip, then somehow slip, and his straining cock springs back up and slaps his belly as he stands over me. It's so hard, it's so erect, and then I'm pulling the tip down into my mouth again, between my cocksucker red lips. His gasp is so rewarding, so satisfying to me, and I push forward, taking him deeper into my mouth.