tagTranssexuals & CrossdressersMy Transgender Neighbor

My Transgender Neighbor

byLara_Longstaff©

** Disclaimer! Like a lot of my stories this one features a girl with really a large endowment, and through the course of the story, she learns that she likes being "on top" best, perhaps even exclusively. Not everyone likes that kind of arrangement so I thought I'd give everyone a 'heads up'! Also, there's some discussion of politics surrounding transgender folks that some might take issue with as well. Anyway, Thanks for reading! **

*****

There was a bounce in my step when I came home from work that fateful Friday evening. As usual I'd worked my fingers to the bone trying to impress my boss. William Danforth Carter hadn't given me much more than a grunt when I handed in my reports at half past six. He'd barely acknowledged me at all, in fact. That wasn't unusual for him; he was a colossal prick, after all. No, it wasn't my boss that had me whistling and nearly skipping down the sidewalk to the door of my little apartment. And it wasn't the smell of hot spicy barbeque in the take out bag I was holding. It was Julie. Sweet, wonderful, adorable little Julie whom I'd worked with for two and a half years. She was sweet, petite, gorgeous and nice as can be. I'd finally decided that thirty months was long enough a time to carry a torch. I'd asked her out for Saturday night and she'd said yes.

I was still so full of my own excitement that I barely dodged the boot in time. I jumped to the side as the heavy black work boot flew by my face. I moved so fast I nearly dropped my dinner on the stairs leading up to my door. A big, burly guy was running down the stairs right at me. I have to admit, I yelped a little as I jumped once again, this time to get of his way. While I'm not the biggest guy in the world, heck, I'm one of those tall, skinny guys, I'm pretty fit and generally don't make a habit of squealing. Another boot flew down from the landing at the top of the steps that connected my unit to my next-door neighbor's. It hit the big guy square between the shoulder blades as he passed me.

"And don't ever let me see your pig face again, Gary!" my neighbor yelled. The guy, who looked about thirty and covered with more muscles than a gorilla, just kept running. He left his boots and a faint whiff of too much aftershave lingering in the air behind him.

"Jesus, are you all right, Caroline?" I called up to my neighbor. She'd moved in a few months ago, but I never really saw that much of her. Every once in a while I'd meet her coming or going, or peeking through the window by her door when I came up the steps. She had a lot of visitors, and while a lot of them were women, more than a few men would come up to her door. I could understand why. She was gorgeous. Tall and blonde and stacked and always dressed for a night on the town, no matter what time of day.

"Nothing I couldn't handle," she snorted.

"Who was that guy?" I wondered.

"Just an asshole I met online. I haven't had one of those in a long time," she growled. She had a husky voice just a little too rough to be called silky. And she sounded pissed. I reached the top of the steps and did a double take. Her customary style was professional dresses and skirt suits. She always seemed to wear high heels and that night was no exception. Only she was wearing very little else. Just a lacy black bra and a g-string. Now I'm a pretty good looking guy. I've got dark hair and eyes and I'm pretty confident about my looks around most women. Next to her dressed like that, though, and I suddenly had the urge to hit the gym and work on my abs.

"Oh! Sorry, Caroline!" I said. I have to admit, I stared. Not for very long, but probably for too long, if you know what I mean. I couldn't help it. Her body was pretty much exposed right in front of me, lit perfectly by the bright halogen lamp above us. I may have been in love with Julie, but I had a hot, nearly-naked blonde standing right before my eyes!

"No worries, Mike," she shrugged, then smiled at me. She had one hell of a smile. "Anyway, I should apologize to you! I didn't mean to make a scene. He just... Well, he freaked and got nasty."

"It's okay," I shuffled my feet and tried really hard not to stare down at her cleavage. I felt like I could sink my face right in there and not come up 'til February.

"I guess that's what I get for dating guys off the internet," she sighed and shook her head.

"He was a date, not one of your, err..." I didn't know what to say. I'd seen plenty of men and women coming to her place, usually after normal work hours.

"My clients? Nope. Do you think a guy like that needs help writing a resume or practicing for job interviews? He said he was a mechanic." she frowned.

"Oh, so that's what you do!" I laughed and slapped my forehead. She looked down at me, and I squirmed. At six-two I wasn't used to many people being able to look down their noses at me. In her sky-high heels, though, she had at least an inch on me.

"What did you think I was a call girl or something?" she frowned at me so hard I worried laser beams were going to shoot out of those deep blue eyes.

"I honestly had no idea!" I corrected myself as fast as I could.

"All right. I believe you," she nodded decisively and her frown disappeared just like that. "A lot of people assume things about girls like me."

"Girls like you?" I scratched my head. I'd been so caught up with chasing Julie and working my ass off at the office I suppose I never really bothered to think things through. The evidence was starting to add up though. Her height. Her voice. The equality sticker on the back of her car. That time a couple of months ago when she went on a rant about the transgender bathroom laws in another state while I stood in front of my door with my keys in my hand nodding and agreeing with her. I couldn't help but let me gaze drop. Sure enough, her black panties seemed to be stretched very tightly around a bulge a good deal bigger than one would expect to find between a genetic woman's legs. Hell, it was a good deal bigger than what you'd expect to find between a full-grown man's legs. She was a transwoman, and she was hung! I guess the surprise on my face wasn't that hard to read.

"Oh my God, you're just NOW figuring that out?" she laughed at me and slapped her knee. I blushed and stammered and tried to make myself sound sophisticated. I could tell I wasn't doing very well because she just kept laughing harder.

"I guess I'm a little slow on the uptake, okay?" I had to laugh at myself a bit too. My best defense against that was to try to be charming. "Besides, whenever I look at you all I can see is a very beautiful woman!"

"You're damn right you do!" she said when her hysterical fit finally ran its course. "You're all right, Mike. Most of the guys I meet know what I am before hand. Makes it easier."

"Not always, though, I guess, huh?" I jerked my head toward the stairs where her date had run away.

"Sometimes guys only THINK they can handle me, until they see me up close!" she winked.

"Why would that make any difference? I mean, you could be a swimsuit model or something, Jesus!"

"This," she patted the big bulge in her panties. "I've got her tucked away pretty good, but when I let her loose, she can scare some guys."

"Oh please!" I rolled my eyes. "I think you've been dating the wrong kind of guy! Only juveniles worry about measuring contests!"

"Hmm, maybe your'e right. Maybe I should find a nice straight guy like you who isn't intimidated by me, or hung up on how big his dick is. How come a nice girl hasn't come along and snatched you up? It makes me wonder what secrets you're hiding," she stepped closer, and I suddenly remembered my date the next night with my sweet little Julie.

"I know. I've been in a dry patch lately. I got a date for tomorrow night, though."

"Oh," she frowned a little. "Well, let me know if it doesn't work out for you!" She bent down and gave me a quick little kiss on the cheek. Her perfume smelled exotic, just like her. I tried to think of something to say, but by the time I did, she'd already closed the door of her apartment behind her, leaving me alone on the stoop.

* * * *

The next day I was so stoked about my upcoming date with Julie that I forgot all about Caroline and her bulging panties. I wasn't supposed to pick Julie up until seven that night, and after showering and having breakfast, I was a bit at a loss as to how to fill my day. I tried playing video games for a while, but decided that I needed to do something more active. I put on a tank top, shorts, and a pair of running shoes and headed out to take a jog. As soon as I stepped out onto the landing between our apartments, my neighbor's door opened up.

"There you are, handsome!" Caroline said cheerfully. She leaned against the door frame, wearing a bikini top and shorts of her own.

"Hey there, Caroline," I smiled at her. She sure was pretty. "Were you watching out for me through your little window?" I joked.

"Of course I was!" she admitted. She stepped out of the doorway. She was barefoot, but still only a little shorter than I.

"Well, if you're going to stalk me at least you're good enough to be honest about it!" I laughed. Things could be worse, even if she wasn't born a girl.

"Maybe I am, maybe I'm not!" she shrugged as if it were nothing, but I could see something in her eyes. A hungry look.

"Uh, yeah. Well, I'm just going for a run," I gulped. I'd never considered dating a woman like her before, and the way she was looking at me made me more than a little nervous.

"Now that you mention it I haven't had my morning work out. Do you mind if I join you?" she asked.

"I don't know..."

"What, are you afraid I'm going to run circles around you?" she teased. "Just give me a second to get my shoes and socks on." She turned and headed back into her apartment before I could protest. She looked over her shoulder at me from just inside her apartment. "And my sports bra. I don't want to be jiggling out all over the place!"

"Fuck," I muttered as she faded from view. It seemed to take her forever to come back. All I could think about while she was gone was her perfect bosom and that bulge in her panties. One image was hot, and the other... Repulsive? Confusing? Sexy? All three?

"Miss me?" Caroline quipped as she returned. Her sports bra wasn't much less revealing than her bikini top had been. There was cleavage to spare. More than that, her lycra shorts revealed just as much, stretching tight around her huge bulge. She was letting it all hang out today!

"Uh, wow. Sure," I didn't know what else to say. It was a pretty nice day, but it suddenly seemed quite a bit too warm.

"Race you to the park!" Caroline squealed like a young girl and pushed past me to run down the wooden steps. I could either stand there like an idiot, or join in her fun and run after her. I took the second option. She was fit as hell, and not holding back. She led me down the stairs and across the parking lot to the edge of the trail the wound through the woods before meeting up with a circular jogging path around a local park. I gained on her steadily, but slowly. It wasn't until we burst from the woods that I pulled shoulder to shoulder with her, and that took every bit of speed I had in me.

"You're fast!" I panted.

"Took you long enough!" she taunted. I glanced at her. Her sports bra wasn't having an easy time of it. Her tits were bouncing all over the place.

"I was having too much fun watching your butt!" I said. It was true enough, but that wasn't normally the kind of thing I blurted out.

"You perv! Let me give you another look!" She took off again, quickly outpacing me. I followed a few steps behind, watching her round, toned rump flex and jiggle in her stretchy gray shorts. I'd never run so fast for so long in all my life, but with that ripe bottom before my eyes, I somehow managed to keep up. The kids and families playing on the swing sets and what not in the park ignored us as we circled them over and over on that smoothly paved quarter-mile track.

"Oh thank God!" I panted as she slowed to a walk and veered back down the path through the woods leading to our apartment complex. I caught up to her and blessedly was able to stop running.

"Don't have a heart attack on me!" she giggled. She was breathing hard, though not as hard as me. Her pretty face glowed with a thin sheen of sweat. At least running circles around me hand't been too easy for her either.

"You really go all out don't you?" I managed to say between gasps to catch my breath.

"Always," she nodded. We strolled slowly through the woods. It was cool in the shade of the trees, and we enjoyed the air in a comfortable silence. As we emerged from the trees and headed back to our building, I wondered where all this was going.

"I see how you stay in such great shape," I said. I had to say something.

"That's not the only way," she teased. "I could take you up to my place and show you some of my other work out methods."

"Caroline!" I gasped. Fuck she was forward!

"I'm just teasing you, big guy," she punched me lightly in the arm as we climbed the stairs, side by side.

"Well," I cleared my throat. She was awfully sexy, if in a totally frightening way. Best to be diplomatic. "I'm very flattered. You're a beautiful woman. Out of my league, really."

"I don't think so. But does that mean you're thinking about it?" she wondered as we reached the landing. We could turn our seperate ways and the whole uncomfortable encounter would be over, just like that.

"Sure, but I generally don't just hop into the sack with people without getting to know them first," I said.

"But I do, huh?" she put her hands on her womanly hips.

"I don't know!" Shit, that wasn't the right thing to say. I had to pull myself together. "I'm not judging you-"

"No, you're right," she sighed. "I'd like to find a nice guy to date, have a real relationship and all that stuff. It's not that easy sometimes, for girls like me. Sure, a lot of guys are willing to have sex with us, but to be in a relationship?"

"That must suck."

"It's not great," she said sadly. "And well, I've got needs too. You're a guy, you know what I mean, right?"

"Yeah," I blushed. It had been a long time since I'd had a girl in my bed. It was driving me crazy more than a little.

"So forget what I said earlier," she offered. "We could hang out, get to know each other." She seemed a bit nervous asking me.

"Caroline, I've got a date tonight, remember?" Fair enough that she forgot. But to my shame, I hadn't thought about my date with Julie since my neighbor had come out of her apartment that morning. I was in love with her, wasn't I?

"That's right. I forgot," she looked sad. Really sad. "And that's the only reason?"

"I promise you it is," I said. I took her hand and gave it a squeeze, looking down into her big blue eyes. As scary as that bulge was, I wasn't lying.

"I believe you," she nodded. "Okay, go shower and get ready for your date. I'm going to do the same and then binge watch some TV shows."

"Hell of a Saturday night."

"Don't rub it in, Mike," she said. She pulled away and opened her apartment door. "Have fun tonight!" she said a bit too cheerfully. I waved goodbye and went to my own place. Why couldn't life ever be simple?

* * * *

"Oh, Michael, you're such a goofball!" Julie giggled. It wasn't the response I'd been hoping for. I'd wined her, I'd dined her and I'd done more than my share of pining for her. Julie was pleasant enough company, laughing at my jokes and letting me play the chivalrous gentleman, paying for our date and opening doors for her and all that. At the door of her house, though, I couldn't help myself any more. She was a perfect little petite brunette with the cutest dimples and the sweetest face. I'd swooped in for a kiss. And she'd turned her head and laughed.

"I'm a goofball for wanting to kiss you?" I asked.

"It's our first date, silly!" she admonished teasingly. She pushed herself away from me with both her little hands on my chest.

"All right, that's fair!" I agreed. God she was cute. I would have agreed to anything.

"Maybe on the second or third date," she added primly. I knew she was pretty conservative, but that seemed like a long wait, just for a kiss. My blood was boiling for her.

"Okay. How about tomorrow for lunch?" I offered. I'd rather make it breakfast, but she wanted to move slow and I had to contain myself.

"You know I go to church all day," she frowned deep, her eyes narrowing to little slits.

"Oh, right," I agreed.

"I'll talk to you on Monday, Michael," she said quickly before turning on her heel and marching to her door. She was wearing one the same conservative skit suits she often wore to work, with her hair in a bun and flats on her tiny feet. I'd been hoping to see her with her hair down and showing off a bit more of her delightful figure. Instead she was shutting me down.

"Good night," I forced myself to sound cheerful. I don't think I quite succeeded in keeping the frustration from my voice. She just waved over her shoulder at me then shut her door tight behind her. As I started my car I resolved to turn on the charm. She was a nice girl. Sure she was a little uptight, but once she got to know me outside of work, I was sure I could get her to warm up even more. Hell, maybe she'd even stop calling me Michael!

The rest of the week was torture. Julie was as nice as ever, but it seemed superficial, distant even, after we'd been on a date. She agreed to a second date that Friday, though, and had been rather enthusiastic about heading down to the old boardwalk amusement park that she used to go to as a girl. A little nostalgia always made for a good date. Still, I wanted to kiss her pretty little mouth every time I saw her, and each day I'd come home from the office positively shaking with pent-up lust.

That's when things would get even harder. Caroline seemed determined to be my friend. She'd knocked on my door with a pizza and six pack Monday night, offering to watch the game. I loved football, pizza, and beer, but had been tempted to send her away. What did it for me was the way she'd dressed. Gone was the make up and heels. She'd had her hair pulled into a ponytail and had worn blue jeans and a baggy tee shirt.

"I don't have a lot of friends, Mike, and I can tell you're a nice guy. No bullshit, you know?" she'd said, and I'd taken her at her word. She was good on it too. The sexual innuendo was gone. Trouble was, she hardly needed it. Transgendered or not, she was sexy as hell. We ended up hanging out several more times that week, and each time we did, I had to spend a few furious minutes stroking myself off alone in my bed before sleep. I tried my best to think of Julie's face when I did, but more often than not, it was Caroline filling my brain by the time I lost it.

Friday night finally came, and that's when everything came to head, so to speak. Julie really seemed to loosen up at the boardwalk. She held my hand and leaned into my shoulder. She laughed and cheered me on when I threw balls into cups and won her a little Teddy Bear. We even kissed on the Ferris Wheel. Granted, it wasn't a full-on passionate kiss, but a quick little peck on the lips. But it was progress nonetheless. With both of us in a great mood, I thought I'd test my like and ask her back to my place.

"Michael, I don't think that's a good idea," she said softly. The neon lights of the shops and rides of the boardwalk park illuminated her sweet face in eerie shifting colors. She looked ethereal, almost magical. She leaned against the side of my car and gave me a thoughtful look.

"Why not, Julie?"

"I have to know this is serious."

"I should confess something. I've been in love with you since the day we met. I know it sounds corny, Julie. I guess I thought you were too good for me, or I was afraid of rejection, but I've felt this way for a long time. I hope that doesn't sound creepy."

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byLara_Longstaff© 28 comments/ 75572 views/ 187 favorites

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