My Transgender Neighbor

"Oh fuck," I groaned. I shook my head violently and swore as loudly as I could. It helped, a little. Then she pushed another inch inside me, and just like that, the pain evaporated. I stared at the window before me in shock. I couldn't see it, but I could feel my jaw hanging slack.

"Does it still hurt?" she asked sweetly. Such a sweet one she was. I had to put her mind at ease, if only I could gather my wits enough to speak.

"No. Good. More," I somehow managed to form the words. I was quivering, shaking on that bed like a drunk three days into rehab. But Caroline understood, thank God. She said something, but I was so filled with sensations I couldn't make it out. She pushed more of herself into me. With each inch I felt the muscular tube of my ass open up deeper and deeper into my belly. With each inch the weirdly intense pleasure only magnified. There was a strange twinge of pain, deep in my guts, near the end, but once it passed, the pleasure doubled yet again. The bed shook.

"Yes!" Caroline cried in joy, and as she did I felt it. I felt her skin pressing firmly against my ass. I felt her heavy balls swing forward and bump mine between my legs. She was all the way in!

"Fuck me, Caroline. Make a man out of me," I slurred. I don't where the hell that came from, probably because my ass was virgin territory. She seemed to find it funny though.

"Oh you'd better believe it, Mike!" she said. Her hands landed on my cheeks, and she roughly pushed me forward several inches. I wasn't having any of that. I braced myself on the mattress and pushed my ass right back, impaling myself on her huge dick. She liked that even better, I guess, because she did it again, and just as before I pushed right back.

Again and again she pushed me away and let me rock right back onto her dick. I did it harder each time, making louder and louder slapping noises as our bodies crashed together. The hard thrusts kind of hurt a little, deep inside, but it was nothing compared to the orgasmic pleasure I experienced. Well, orgasmic in terms of how good it felt. But I'd never had an orgasm that just kept going and going, for minutes on end!

"Fuck me, Caroline, come on!" I urged her. I looked back again. She had this wonderful expression on her face. Part sheepish, part lusty, and partly like a fat kid watching candy being made. She nodded at me, and grabbed my hips. I'd worked out with her before, and knew just how fit and athletics she could be. She used every bit of that on my ass.

"You're ass is so hot!" she exclaimed as she beat her body violently into my backside at incredible speed. I could no longer distinguish her thrusts inside of me. The friction and stretching all combined into a glorious sensation far beyond any mere orgasm.

"God Caroline! Do me!" I pleaded with her. Why I don't know, she was already fucking me like a god-damned maniac! We screamed and moaned together as we frantically pushed our hot, sweaty bodies together over and over. I looked back at her again, and the sight of her enormous breasts wobbling to and fro on her chest was simply too much.

I screamed. I didn't yell. I didn't shout. I screamed. I screamed high and shrill like a chick faking her cum on a two-bit porno. Only it wasn't fake. Caroline fucked me so hard my cock was wagging under me, slapping against my stomach in a rapid beat as my body jerked back and forth on the bed. I could feel myself cumming, feel the hot liquid gush from my cock and spatter all over my belly and chest, though most no doubt coated the sheets beneath me. But that wasn't what felt good. My ass clamped down around her cock, squeezing her so tight she could barely move in and out of me. I could feel every muscle in my intestinal tract ripple and caress her shaft in one wave of contractions after another. Each one felt like a dozen hard cums rolled into a ball, and to this day I'm truly shocked that I didn't pass out or die of a heart attack.

"Too fucking tight!" Caroline's cum followed mine by seconds. No surprise, considering how tight my butt was choking her giant dick! Her cum shot straight up into my belly. It was so hot it almost burned, and I swear I could feel it sloshing around inside me. She took a few dozen more slow, but energetic thrust before she pulled out and flopped back onto her back. She was panting so hard she almost started to wheeze.

I sort of let myself fall to the side. I could feel the cum pouring out of my stretched butt. I was shivering and tingling with little aftershocks of pleasure.

"Caroline," I said a couple minutes later when I'd finally caught my breath.

"Yeah?" she replied. With a groan I flopped around and lay next to her, resting my arm across her wonderful bosom.

"That was, well I won't lie. That was the best sex I've ever had. I hope you enjoyed it too."

"Enjoyed it?" she scoffed. "Christ I forgot how much I loved doing that," she said it like it was a revelation. And I suppose it was for me too. I kissed her. Then I kissed her harder. And then I kissed down her body to suck her glorious nipples.

"You're getting me hard again," she warned me.

"What? A third boner?" I gasped and looked down. Sure enough, she stood right up at attention, her cock still wet and sticky with lube.

"I know right?" she laughed. "But so are you, handsome," she glanced down toward my own erection where it poked against her thigh.

"Want to go again?" I suggest.

"Sure!"

"It's your turn to choose," I fished around for the plastic lube bottle.

"Are you still willing to do that, take turns?" she asked carefully. "No judgment?"

"Of course!" I said and handed her the bottle.

"Then I won't need this," she took it from my hand and threw the lube on the floor. "I'm still pretty slick," she grinned.

"Hot damn!" I smiled. I'd been hoping that's what she would choose. The next few hours could only be described as a marathon of anal sex. We fucked for the second time with me on my back while she drilled me like a woman. Once she came deep inside me we pulled ourselves out to the living room and ate up the rest of the cold pizza. With that break over it was my time to choose again. I had to suck her for a while to get her hard for the fourth time, but hard she got and she fucked me right there on the coffee table with my legs up in the air and her plowing my loose, sloppy ass.

By the time we'd had a nap and woken up to have some really steamy shower sex, it was pretty clear that the whole game of passing the lube back and forth was pretty much over. She clearly preferred to fuck and I was addicted to being her willing slutty little bottom. But that was just the beginning of our fun. For a few weeks we'd go back to doing it "the old fashioned way" as we'd taken to calling it when I topped her, once in a while. As the weeks turned into months, though, I'm not ashamed to say that both of us pretty much lust interest in sex with me on top, even with oral sex. Even blowing her was more satisfying to me than the reverse, as strange as that may sound, and she certianly wasn't complaining!

But as unconventional as our sex life was, our romantic life was pretty by-the-book. We dated for months. We moved in together for a couple of years. Then, when we could go ahead and do it legally, we got married. It's been five years now since I first kissed that gorgeous blonde woman, and we're even thinking of adopting some kids. I've never been happier.

As for Julie. I wouldn't worry about her. It was awkward as hell working at the same office with her, but she got over it. All the dirty looks and snide comments she threw at me couldn't dampen my happiness with Caroline. She eventually quit. I have no idea where she went or what happened to her, but I can't really say that I care, either. All I can say is, you've got to keep an open mind and be ready to take a chance when one arises. I almost missed my chance, but thank God every day that I didn't completely fuck it up. And if you happen to meet a good-looking trans woman out there, go ahead and give her a try. Just don't use her for sex, remember that she's a woman, and a human being. You just might be surprised!

THE END