My New Trans Neighbor Took My Virginity That Afternoon

I was twenty-three when I moved out on my own for the first time. I rented a small apartment on the outskirts, with the idea of getting myself organized between college and my part-time job, and during the first few months my life was a succession of almost identical days. Getting up early, studying, going to the shop where I stocked shelves, coming back, having dinner with whatever I could find, and sleeping. The monotony had something comforting about it, but also something that was slowly extinguishing me inside.

That changed one March morning, when a moving truck parked right in front of the entrance to the building across the way.

I watched her get out of the car and my mouth went dry. She was tall, must have been close to five foot nine, blonde, with long hair falling over her shoulders and green eyes that seemed to light up the landing. She had long, firm legs, generous breasts, and a body that would make anyone turn their head. She was carrying a huge box and climbing the stairs with difficulty.

—Wait, let me help you —I said, almost without thinking.

—Oh, thank you so much, really —she replied with a huge smile.

—It’s nothing. You’ve got a ton of stuff and only two arms.

I picked up three boxes and followed her to her apartment, on the second floor. She pushed the door open with her hip and pointed to the empty living room.

—Just leave everything there, I’ll put it all away slowly later.

—As you wish —I joked.

—Oh, don’t call me you, you make me feel old. Especially not when you’re such a handsome boy —she said, and winked at me.

I felt my ears getting hot. With a boldness I didn’t know I had, I invited her over for a drink at my place, just across the hall, when she was done.

—That sounds perfect. I’ve finished the heavy lifting and I’ve got nothing else to do. Besides, that way I get to meet my new little neighbor.

***

Half an hour later she was knocking on my door. I made two decaf coffees and we sat on the sofa, the only decent piece of furniture I had then. We talked about a little of everything. I told her I was studying, working, that I’d only recently moved into the neighborhood and still didn’t know anyone. She listened with her chin resting on her hand, never taking her eyes off me.

—My name’s Daniela —she said when it was her turn—. I’m twenty-six, I work for a design company, and I’m single. And there’s something I’d rather tell you now, because I don’t like beating around the bush: I’m transsexual.

She said it with complete naturalness, without lowering her gaze, like someone commenting on the weather. I froze for a second. Not from rejection, but from the exact opposite: I felt a surge of arousal that surprised even me. But something in my head refused to believe it.

—I don’t believe you —I blurted out—. You’re a beautiful woman.

—And why don’t you check for yourself? —she replied, tilting her head.

She set her cup on the floor and stood up. Slowly, never taking her eyes off me, she unbuttoned her jeans and slid them down her legs. Underneath she was wearing black panties, and beneath the fabric a bulge could be seen that left no room for doubt. Then she took the panties off too, and I realized I had been completely wrong.

—Wow —I murmured, unable to look away—. It’s bigger than mine.

Daniela laughed, delighted by my reaction.

—Nine inches —she said, taking it in her hand—. And all yours, if you want it.

I had never been with a man. I had never even thought about doing it. And yet, at that moment I wanted nothing else.

I stood up and kissed her. It was a long, deep kiss, with our hands searching everywhere. I grabbed her firm ass and she did the same to me, while I felt her member harden against my stomach. Without breaking our mouths apart, we stumbled our way to my bedroom.

***

There we finished undressing. First her, letting her shirt fall to the floor; then me, with clumsy fingers from nerves and desire. The arousal was overwhelming me. I dropped to my knees in front of her almost by instinct.

—I’m so horny —Daniela said, her voice rough—. I want you to suck me.

I took it into my mouth without thinking twice. I started slowly, moving up and down, trying to take her deeper each time. The taste, the weight, everything was new, and much more exciting than I had ever imagined.

—Fuck, you’re so good at this —she panted.

I pulled back for a moment to catch my breath.

—It’s the first time I’ve done this —I confessed.

—Well, it doesn’t look like it, I swear. You suck like you’ve been doing it for years.

I went back to work, picking up the pace. She wanted me to take all of her, and I tried, though sometimes I gagged and had to stop. I didn’t care. The more I heard her moan, the harder I tried.

—Do you like my cock? —she teased me.

—I love it —I answered between licks.

—Then wait until you feel it somewhere else.

Her blunt, almost filthy words had me on fire. After a good while, she gently stopped me, placing a hand on my forehead.

—Now it’s my turn —she said.

I lay down and she leaned over my crotch. What came next was brutal. Daniela swallowed my whole member, jerked me off with one hand while she did it, and managed to take me all the way down her throat without effort. She was an expert, a beast.

—No one’s ever sucked me like that —I said, clutching the sheets.

She kept up that frenzy for a long while, until she sat up with glossy lips and a naughty smile.

—You’ve got a cock and an ass that drive me crazy —she said—. Turn around.

***

I lay face down and felt her hands parting my ass cheeks.

—If you’ve never been with a man, I guess no one’s fucked you, right?

—No, no one —I admitted, my heart pounding.

—Want to try?

—Yes —I said, swallowing—. But be careful.

—Don’t worry. I’ll go slow.

She started eating my ass in that same position, and the sensation shot down my back like a jolt. I hadn’t imagined something like that could feel so good. From her moans, she was enjoying it too. After a while, she got up.

—I’m going to get the lube, it’s in my bag. We need to prepare you properly.

She came back right away with a bottle. She let a little cold liquid fall between my ass cheeks and coated her fingers with it.

—If it hurts, tell me and I’ll stop. We’re in no hurry.

I nodded, my face buried in the pillow. First she gave me a gentle massage to spread the lubricant, then she slipped in one finger, slowly, tracing circles inside me.

—You okay?

—Yes —I answered—. I’m really liking it.

—I’m going in with the second.

With the second finger I felt discomfort, a different kind of pressure, and I felt myself slowly opening up.

—Okay?

—It hurts a little, but keep going.

—The more I do it, the more you’ll get used to it —she said softly.

She stayed like that a few more minutes, until the discomfort turned into something else, into a pleasure that made me push my hips against her hand.

—Now I’m really enjoying it —I admitted.

—I’m going in with the third, and then my cock.

With three fingers I felt my body completely open, but there wasn’t the slightest trace of pain. Daniela handled the situation like a true professional.

—I think you’re ready now —she said—. Now comes the hardest part. Get on all fours.

***

I obeyed. I felt the tip of her member pressing against me, and she started to enter slowly. At first it really hurt, so much that a cry escaped me and I asked her to stop.

—Hold on a little —she whispered, stroking my back—. The pain’s going to turn into pleasure, you’ll see.

She began moving carefully, pushing in and pulling out just a few inches, and little by little the pain vanished. In its place remained an intense, full sensation, while I felt every inch of her inside me.

—Now I’m really going to fuck you —she said, her voice thick with desire—. Your ass is ready for me now.

She picked up the pace and I couldn’t hold back a long moan.

—Fuck, you fuck me so well —I panted.

—Do you like my cock inside there?

—I love it —I answered, almost out of breath—. Don’t stop.

—It drives me crazy how filthy you are.

She fucked me hard, without mercy, and I loved feeling her like that, wild, on all fours over the bed. Just when I thought I couldn’t take any more, she stopped abruptly.

—I want you to ride me —she said.

She pulled out and, for a moment, I felt a strange emptiness, almost like a loss. Daniela lay back and I rose over her, reaching for her member with my hand, and began to lower myself slowly until I felt her inside me again. I started moving, setting the pace this time, while she dug her fingers into my thighs.

—I’m going to come —she warned after a few minutes—. Where do you want it, inside or in your mouth?

—In my mouth —I said without hesitation.

I pulled away, she grabbed herself, and I opened my mouth just in time. She came with a deep groan, and I cleaned her off completely, licking up every last drop while she watched me with half-lidded eyes.

—I loved taking your virginity —she said, catching her breath—. You’re a gorgeous filthy boy, and you and I are going to have a very good time. Next time I want to feel yours inside me.

I collapsed beside her, exhausted and happy, knowing my nights in that building would never be monotonous again.