My Transgender Neighbor

"You have a nice cock," she said with a nervous giggled.

"So do you," I pointed out.

"Nicer than yours," she stuck out her tongue.

"You weren't saying that all those times I fucked your sweet little ass!" I taunted.

"I was just being polite," she said primly. "I didn't want to scare you away by trying to take your anal virginity."

"Is that right?" I gulped. I had no idea she had even thought of that. "Is that something you, uh, want?"

"Not so eager now are you?" she joked, but I could tell there was a bit of bitterness behind it.

"Your cock is thicker than your wrist. Wouldn't you be nervous?"

"Now that you mention it," she giggled. "I haven't actually fucked anyone in years. Not before I transitioned. It didn't seem like what I was 'supposed' to do."

"What, are there rules to being transgender?" I asked. I was genuinely curious.

"Some act like there are. If a guy seeks out trans women to date, we're supposed to avoid him for being a 'chaser' with a fetish. If a girl like me wants to be on top, it means shes' less of a woman," she lamented.

"Is that how you feel?" I asked her.

"Kind of. I mean, I'm conflicted. I really enjoyed being on top before I transitioned. And yeah I miss it. But I kind of hate myself for want it too. As for dating chasers, it avoids a lot of problems dating men who are into trans. They know what to expect. No surprises. Well, not as many anyway," she chuckled.

"Yeah, like that meat head guy."

"Yeah like him. But dating guys like that does kind of make me feel like a sex object though. I mean does he like me because of ME or because I was born a genetic male?"

"I can see that. But what about men who like blondes? Or women with big breasts? Or women who are tall or short? Or white men who wouldn't date a black woman? They are singling out one physical attribute about a woman that they like or dislike. Are they just as bad as these 'chasers'?"

"Hm, probably, I guess. I never thought of that."

"It seems like just another physical preference. Sure maybe it isn't exactly laudable. I know we're all supposed to judge people only by what's on the inside and all that. But I'm not going to date a four-foot tall hunchback with buck teeth and warty skin, I'll tell you that much!"

"Why not? She sounds hot!" Caroline giggled.

"Then you date her!" I laughed. "But it turns out I was dating a girl like that. Only she was ugly on the inside."

"True."

"I just didn't realize it at the time," I said.

"And what about transgender women?" she asked.

"I never thought of dating one before meeting you. Would I seek them out, if I can't convince you to forgive me? Maybe, actually." I admitted.

"Are you turning into a chaser?" she giggled.

"I don't know, I guess I am. I do enjoy sucking you," I felt my face getting hot.

"Well I have some friends I could introduce you to," she offered.

"So there's no chance you'll forgive me and let me take you out on a proper date tomorrow night?" It was a long shot but one I had to take.

"The chances are slim," she said. I felt crushed, and turned away. She went on, "But I know this cute trans girl you might like. She's really slender, like Julie. With brown hair like her too. Just your type. I think you and she would get along. She hates chasers though, so you'll have to act surprised when she tells you she's trans."

"I don't want to date just any trans woman!" I growled.

"No?" she cocked her head, a smile twitching on her lips.

"I like you, Caroline. And yes, I think it's hot that you're a trans with a big cock and that you secretly want to fuck my virgin ass. But that's only part of things. You're beautiful. You're clever. You're a good friend and I want to find out if we can be more."

"You're such a sweet-talker, Mike," she cooed. "Do you really mean all that?"

"Yes," I stood up and leaned over her, meeting her gaze. "I want to try having a real relationship with you. I was freaked out before but now I don't care. I'll call up everyone I know and tell them I'm dating a transgender girl and that I'm falling in love with her, I don't care what they think."

"Falling in love?" she gasped.

"Is that really so crazy? You're an amazing woman, Caroline. But I won't know for sure until we give it a shot. What do you think?"

"Mike, Mike, Mike," she smiled. Her eyes twinkled, a little wet with what looked like tears. That was all it took. I was back in her good books. The best part is, I didn't have to lie to her once. I pulled her off the couch and into my arms. Kissing her was like a dream, even with the taste of beer and pizza on her sweet pink lips.

"That's my name," I confirmed after our kiss. It made her laugh again. I know I'm not Adonis, but I'm in pretty good shape. I bent down and scooped her up into my arms with a grunt. Caroline was no petite little princess. More like an amazon. Five-ten and curves in all the right places. She laughed and squirmed and I barely held on as I carried her to her bedroom.

"Put me down," she panted, and I heaved a sigh of relief as I set her on her bare feet. She didn't fuck around. She pulled off my shirt and undid my pants before I could even muster a response.

"Wow, you really think I'm hot," I chuckled.

"You know it, big boy," she said when she jerked my pants down to my ankles. My hard on popped right up into her face, and she looked down at it. "Well, not that big," she giggled.

"Oh you bitch!" I snorted and kicked off my shoes and socks. I was pretty good sized. Above average, but I really couldn't get mad at her for her tease. Not when she was stripping down to nothing right before my eyes. Her tits were like a dream. Surely mostly silicone, but high and round and perfect nonetheless. I wanted to dive into them as soon as those naked orbs came into view, but she stepped back and bent over to pull off her shorts and panties. When she stood back up, the reason she could be so harsh about my size came right into view. She was hung better than most porn starts. Better than most black porn stars. It's funny how even after sleeping with a woman a dozen times you can still be surprised by her body. Her tits were beyond compare, but that cock took my breath away every time.

"Come and get it, if you want it," she purred in that husky voice. She sat on the edge of the bed and spread her long, luscious legs. Her cock stuck straight out, more than eleven thick, hairless pink inches throbbing with need. Her shaft seemed to point to a spot on the carpet between her large, yet somehow still delicate feet.

"I want you," I clarified. Then I showed her. I lifted her heavy cock out of the way, pressing that pulsing log of a shaft up against her tanned, toned belly. Her balls hung under it, pink and hairless and absolutely massive. They tasted good too. I slathered those lemon-sized orbs with my tongue. I nibbled at them with my lips. I did my best to suck them into my mouth one at a time. Caroline moaned and leaned back on the bed, watching me work.

I glanced up at her and winked, then got to work making her scream. I munched upward, at first nestling my tongue in the little hollow where the underside of her heavy shaft met her body. I opened my mouth wide, pressing my lips to her flesh. My tongue swished side to side as I ever so slowly pushed up from my knees.

"Yes, get it nice and wet Mike," she cooed. Her fingertips teased my thick dark hair and I kept on moving. Moving, but not fast. I wanted to make her beg me to let her cum. Spit dribbled over my lips and down my chin. It ran down her shaft and dripped onto her balls and I wasn't even halfway up yet. I could see her toes curling in the carpet as I moved my way up. Long and suckable, with the nails painted bright pink. I almost paused so I could suck them too, but at the moment, her cock was the center of my attention.

Caroline started to squirm as my mouth neared the top of that monumental erection. I somehow managed to open my mouth wider, so wide my jaw ached. I pulled her cock down at the same time, making it stick out straight and level with the floor. I hunched down, never letting my lips lose contact with the pink, spongy head. I gulped her inside my mouth, moaning in slutty satisfaction as her giant cock head completely filled my mouth.

"God yes, suck me," she moaned. Her voice got even deeper when she was turned on. Not quite manly, but definitely more than feminine. It made me hot. I squeezed her firm tits as she leaned back and took the ferocious sucking I was giving her. I'd sucked her dick many times, and it always made me feel like a girlish little whore. I fucking loved it. More each time I did it. I started to bob as I slurped, pinching and twisting her long pink nipples as I did.

By her almost manly moans and the way her perfect thighs quivered at my sides, I knew she was loving it even more than I was. Well, maybe almost as much as I was. But for all my time sucking her off in the past, there was one thing I'd never even had the courage to try. I slurped down her cock, feeling the stiff tip poke the back of my throat. She grunted in appreciation. I almost gagged a little, but I sucked air in deeply through my nose. It was now or never.

I pushed again, trying my best to swallow as her cock began to wedge down my throat. I'm not gonna lie. It hurt like a mother-fucker. As soft and silky as the skin of her cock was, it felt like I was trying to swallow jagged ball of broken glass. I gagged then, and it only got tighter, hotter and more painful. I pulled back, sucking at the tip of her cock for comfort like a little kid sucking his thumb.

"I'm too big for that, Mike! You don't have to do that!" she said, and from the look on her face, I knew she was truly concerned. Thing is, I was a man. And not a little man. And I'd seen dozens of girls half my size deep throat cocks nearly as big as hers in porn. If they could do it, so could I.

I tried again. I could feel the tears streaming down my cheeks. But even with my vision blurry, I stared up at her pretty face and heaving tits and kept pushing. It was like trying to swallow a baseball bat, but swallow her I did. Inch by painful, gagging inch. Bit by bit her veiny shaft disappeared into my mouth. I could feel my throat stretching out, first in my neck, but then even further into my chest. Both of those things turned me on to no end, and by the time I finally ate her entire, massive cock, the pain seemed like a distant fucking memory.

"You're amazing," she moaned. I blinked away my tears to see her smiling down at me in absolute wonder and joy. It made me feel strangely proud. Not only was a slutty little bitch, but I was GOOD at it! I nodded and pulled back, but not too far. About a third of her cock appeared before my eyes, coated with my spit. I rocked forward and ate it all up once again. Then again, and again. And before long I was bobbing and moaning around her. My cock throbbed achingly hard between my legs but instead of reaching down to jerk it, I kept my hands busy on her marvelous tits, kneading them like there was no tomorrow.

"Gonna cum!" she announced some time later. And just as well, with her stamina I was lucky to finish her off before my throat really gave out. I was on fire! I pulled her out of my mouth, nearly gagging once again as her knob cleared my abused gullet. Her cock jumped on my tongue, and I wrestled with it, sucking so hard my chest ached. She squealed. She bucked. She let out a long, ever so low moan. And I got my reward.

Her cum was sticky and hot and salty as always. It filled my cheeks to overflowing. I swallowed as fast as I could, and the hot goo soothed my aching throat. I gulped at it like a cheap slut, eager to not miss a drop. Caroline twitched on the bed, moaning and gripping my shoulders as she unloaded her spunk down my throat. As greedy as I was for it, some of it escaped my hungry mouth and dripped all over her throbbing shaft. I sucked her cock head clean before lifting her steely shaft upward and lapping up every stray drop of pearly cum.

"You do that so much better than anyone else," she panted, then pulled me up to plant a hot, grateful kiss on me. I loved the way my cum-stained lips didn't bother her one bit, and rammed my tongue down her throat, probably a bit harder than I needed to. She sucked it like a champ.

"Do you still want to, er, fuck me?" I asked. Let me tell you, those were some seriously difficult words to get out of my mouth. I was shaking, but my boner had never been harder.

"I'd love to, but, are you ready for that? I'm really big and I've pretty much gotten used to not doing that anymore." she said.

"Does that bother you?"

"Not that much, really. I feel more like a woman when the man is doing it to me," she said softly.

"Hmm. I kind of want you to. But will you think I'm less of a man?" It seemed logical, right? If she was more of a woman for being on the bottom, then wouldn't I be less of a man for doing the same? The thought was painful and humiliating. What was wrong with me? Was I secretly gay after all without even realizing it myself?

"Oh honey!" she cried and kissed me again. "You're just curious, I shouldn't burden you with my baggage about my self image!"

"I don't want to make you feel bad about yourself!" I assured her.

"I don't want to hurt your feelings, either, Mike. Gurls just have issues with our genitals sometimes," she shrugged.

"Why is this all so fucking complicated?" I wondered aloud.

"Let's just keep it simple then," she said after a moment. "I'm going to get the lube and you're going to put it on whichever cock you want. And neither of us will judge each other...or ourselves, for it, no matter what. Okay?"

"Why do I have to be the one choosing?" I chuckled. Her plan sounded good so far, except the burdens seemed to be all mine.

"I'll choose next time. We can take turns!" she said brightly. "As long as we remember the rule. No judging!"

"You're fucking brilliant. Brilliant and beautiful!" I laughed and kissed each of her perfect, light brown nipples in turn. It occurred to me as I pulled away and she reached over the bed to get the lube from the night stand that she'd said something quite remarkable. There was going to be a next time. And a lot of times after that. When she dropped the clear plastic bottle into my hands I was grinning like an idiot.

"Made your choice already?" she laughed deep in her throat, her blue eyes darting from my cock, to hers, and back again.

"No, actually." I thought about it. Sure I could chicken out and coat my own cock with lube. Let her make the choice whether to fuck me or not. Or I could man up and confront my own desire. I flipped open the top of the bottle and squirted a big dollop onto my palm. It was cold, but I let it warm up before I lowered my hand toward my throbbing, needy organ. At the last minute I reached out and wrapped that fist around her, right at the middle of her thick, spit-covered shaft.

"Oh! Someone wants and adventure today!" she smiled. Her breasts were heaving up and down; she was breathing hard. Her light golden skin seemed pink around her neck and cheeks. She was as nervous as I was. Probably for the best. I squirted more lube on her cock and used both hands to rub in all in, sliding slowly up and down and coating every glorious inch.

"It will be something different. For both of us," I reminded her, and she nodded.

"You'd better get on your hands and knees. It will make it easier for your first time," she advised. Considering how well she took my cock, I knew she had the expertise. I didn't realize just how much I was trembling until I crawled onto her bed and stared out the window facing the parking lot. The bed shifted behind me. The mattress squeaked. I froze, unable to move a muscle.

"Relax," she soothed. Her voice was like warm velvet. She stroked my lower back, then my taut, upturned ass cheeks. "You're like a rock! Just take a deep breath! I swear I'll be gentle!"

"Right," I nodded. I could hear her squirt the lube bottle again, and swiveled my head to get a look at her coating her fingers with the clear, viscous liquid. She noticed me looking and smiled.

I nodded and looked back toward the window. All I could see at this hour was the streetlamp, but I stared at it and waited. When I felt her sticky fingers slide gently between my cheeks I almost jumped off the bed and out the window.

"Easy!" she laughed. "You're so tense! Relax!"

"Sorry," I had to laugh myself a bit too. What was I so nervous for? I trusted her, didn't I? I felt her fingers again and tried my best to just accept it. It took her about two seconds to find my back door and I barely twitched.

"That's better! Doesn't this feel good?" she asked as she rubbed the pad of her fingertip in tiny little circles around my ass. It was tingly, but strange. Almost like going to the bathroom, but undeniably pleasurable too.

"Yeah, it does." I nodded. She kept rubbing. Those little circles started driving me crazy. I wanted to enhance the feeling by reaching under myself and grabbing my dick, but I didn't dare move. I could feel my sphincter relaxing, almost like magic. The pleasure just kept increasing, and I'm not ashamed to admit that I moaned like a girl at that point.

"I told you," she said, and then slipped her finger in me to the knuckle. I should have been more ready for it than I was, but instead it took me off guard. I yelped and my muscles locked once more.

"Did I hurt you," she asked.

"Uh," I had to think of a reply, not because I couldn't tell if it was painful, but because it felt so surprisingly good. "No, not at all," I said at last. I sighed deep and my ass loosened right up again.

"Good! You're doing great, Mike!" she said, and pushed it in deeper. She was a big woman, and her finger wasn't small. It felt like a tree trunk in me, but in no way did it hurt. She stroked my back with one hand as she started slowly fucking me with that one finger. The strange feelings were there again, but the more she did it, the better and less weird they felt.

"I don't think I've ever felt this way before," I said at last.

"No?" she asked as she pushed a second finger in beside the first.

"Fuck!" I hissed. There was a twinge of pain, but that was all. Just a brief flash that hurt no worse than a pinch and faded as quick as it had come. And two fingers felt even better than one. I started pushing my ass back to meet her, and a thought occurred to me. How would three feel?

"Good?" she asked, though by the giggly tone of her voice she already knew the answer.

"More," I begged. And she obliged. The third finger wasn't quite as easy as the second, but the pain of that was just as fleeting. She spread her fingers in my rectum, stretching me as she plunged down to her knuckles. The feeling was so intense, I could have died a happy man in that moment. Before too long I was begging for a fourth.

"No, I think it's time for the main event," she said and slipped her fingers out of my ass.

"Yes!" I cried. How much better would that monstrously thick cock feel? I arched my back and tilted my ass up toward her like a wanton little slut.

"So eager!" she exclaimed. I just nodded and waited. The slippery, lube-covered head of her cock pushed between my slick ass cheeks. I thought three fingers was a lot, but her cock was BIG. The feeling of it sent a shiver down my spine, but then the spongy head bumped against my wet ass.

"Oh!" I gasped, and my grip tightened on the edge of the bed. She rubbed her cock around using those same tiny circles. I could feel my little hole opening, gasping and gaping in its hunger for her mammoth tool. "For the love of God put it in me!" I begged.

"Okay okay!" she relented, and pushed against me. For one horrifying moment I thought I'd gone too far. The searing pain was simply too much. Was she going to rip my ass apart? It dragged on for several seconds, seconds that seemed, at the time, like hours. Then with a flick of her hips, her cock head popped past the stubborn ring of sphincter and into my slippery rectum.