u/Dangerous_Rule_

I was walking towards the railway station at night, feeling so frustrated from a long, shitty day at work. My mind was racing with stress, and I just wanted to get home. As I passed the usual spot near the tracks, I saw the line of trans women standing there under the dim streetlights. I saw them every day on my way back, but I always avoided them, keeping my head down and walking fast. Tonight, though, something caught my eye. There was this beautiful trans woman at the end of the line. She had long dark hair, full lips, and eyes that sparkled even in the low light. My heart skipped a beat. I felt a pull, like I couldn't just walk by. This was my first time ever thinking about approaching one.

I stopped in front of her, my hands sweaty and my voice shaky. 'Hey, uh, what's your rate for a quickie?' I asked, trying to sound casual but feeling nervous. We agreed quickly, and she led me away from the road, towards a cluster of thick bushes nearby. The area was pitch dark, no lights except the pale moonlight filtering through the trees. It made everything feel secret and intense. Only her beautiful face was visible, glowing softly like she was from a dream.

We stopped behind the bushes, hidden from the street. My nerves were buzzing with excitement and a bit of fear—this was all new to me. 'Take off your top,' I whispered, my voice thick. She nodded and pulled her tight shirt over her head, letting it drop. Her boobs spilled out, full and round, shining in the moonlight. They looked perfect, nipples hard from the cool night air. I stared, my cock twitching hard in my pants until it was fully erect, straining against the fabric. I couldn't hold back. I leaned in and started sucking her boobs right away, my mouth latching onto one nipple, tongue swirling around it. She moaned softly, her hand on my head, pulling me closer. The taste of her skin was salty and sweet, making me even harder.

I pulled back, breathing heavily, and yanked my pants down. My erect dick sprang free, throbbing in the air. 'Suck it,' I said, my voice rough with need. She knelt down without hesitation, pulling a condom from her pocket. She tore it open and rolled it onto my hard cock, her fingers warm and steady. Then she leaned in and started sucking, her lips wrapping tight around the base. She was so good—her tongue sliding along the underside, bobbing her head slowed at first, then faster. Wet slurps filled the air as she took me deep, her cheeks hollowing. I groaned, gripping her hair, but I wanted more. I needed to fuck her.

'I want to fuck you,' I panted, pulling her up. She stood and slid her pants down, turning her back to me. Her ass was smooth and round, curving just right in the moonlight. I grabbed my condom-covered dick and pressed the tip against her asshole, trying to push in. But she stopped me quickly, twisting around with a shout. 'Wait! Why are you going in the wrong hole?' Her voice was sharp but not angry, more surprised.

I froze, confused and embarrassed. 'If not your asshole, then where? You don't have a pussy,' I said, my heart pounding. To my shock, she turned fully, her eyes meeting mine. 'Yes, I do have a pussy.' I reached down, my fingers trembling, and touched between her legs. There it was—soft, wet folds, her pussy already slick. I slid a finger along her slit, feeling the warmth and moisture. 'I thought you were a trans without one,' I muttered, my mind blown. She smiled shyly. 'It's my first day out here. You're my first customer ever.' That hit me hard.

I was so happy, my cock twitching again. She bent over in doggy style, holding onto a nearby tree for support, her ass and pussy exposed in the dark. I started fingering her pussy slowly, one finger slipping in easily because she was so wet. Her juices coated my hand as I curled my finger inside, rubbing her walls. She gasped, pushing back against me, 'Ahhhhh,' she moaned. Her pussy clenched around my finger, hot and ready. I couldn't wait anymore. I positioned my hard dick at her entrance and thrust in, the condom sliding smooth into her wet pussy. She was tight, gripping me like a vice.

Out of nowhere, I was fucking her hard, my hips slamming against her ass. I reached around and grabbed her boobs, squeezing them vigorously, pinching her nipples as I pounded. The moonlight danced on her skin, and her moans mixed with the rustle of leaves. It was intense, my first time inside a pussy like this, and the surprise of it all made me thrust deeper. But after a few minutes, I got tired, my legs shaking from the nerves and the effort. My dick slipped out, softening a bit from the overwhelming excitement. She turned her head, thinking I'd cum. 'You okay?' she asked softly.

I nodded, embarrassed. 'Yeah, just nervous. It fell out.' She reached back, her hand gentle on my cock, stroking it lightly through the condom. 'Don't worry. I won't go or stop until you're satisfied. We can lie down if that makes you more comfortable, or even go to a hotel room nearby if you want.' Her sweet voice, full of kindness, washed over me. No one had ever been this understanding, not even my exes. It made my heart swell, and blood rushed back to my dick, getting me erect again.

I pulled her close, kissing her neck softly, my lips trailing down to her boobs. I sucked on them again, feeling her nipples harden under my tongue. She sighed, her body relaxing into me. Then she knelt once more, peeling off the used condom and sliding on a fresh one. She started sucking my dick, her mouth warm and eager, tongue working the head. This time, she didn't stop or pull back—she kept going, deeper and faster, her hand pumping the base. The sensation built quickly, her kindness and skill pushed me over. I couldn't hold it; I came hard, groaning as I shot into her mouth, the condom catching most but her swallowing what she could. She looked up at me with a smile, wiping her lips.

We caught our breath, and I took her number, already planning a full night out at a hotel. God, she was so sweet and nice with me. Even my exes weren't this caring. I walked away feeling lighter, excited for what came next.

I was walking towards the railway station at night, feeling so frustrated from a long, shitty day at work. My mind was racing with stress, and I just wanted to get home. As I passed the usual spot near the tracks, I saw the line of trans women standing there under the dim streetlights. I saw them every day on my way back, but I always avoided them, keeping my head down and walking fast. Tonight, though, something caught my eye. There was this beautiful trans woman at the end of the line. She had long dark hair, full lips, and eyes that sparkled even in the low light. My heart skipped a beat. I felt a pull, like I couldn't just walk by. This was my first time ever thinking about approaching one.

I stopped in front of her, my hands sweaty and my voice shaky. 'Hey, uh, what's your rate for a quickie?' I asked, trying to sound casual but feeling nervous. We agreed quickly, and she led me away from the road, towards a cluster of thick bushes nearby. The area was pitch dark, no lights except the pale moonlight filtering through the trees. It made everything feel secret and intense. Only her beautiful face was visible, glowing softly like she was from a dream.

We stopped behind the bushes, hidden from the street. My nerves were buzzing with excitement and a bit of fear—this was all new to me. 'Take off your top,' I whispered, my voice thick. She nodded and pulled her tight shirt over her head, letting it drop. Her boobs spilled out, full and round, shining in the moonlight. They looked perfect, nipples hard from the cool night air. I stared, my cock twitching hard in my pants until it was fully erect, straining against the fabric. I couldn't hold back. I leaned in and started sucking her boobs right away, my mouth latching onto one nipple, tongue swirling around it. She moaned softly, her hand on my head, pulling me closer. The taste of her skin was salty and sweet, making me even harder.

I pulled back, breathing heavily, and yanked my pants down. My erect dick sprang free, throbbing in the air. 'Suck it,' I said, my voice rough with need. She knelt down without hesitation, pulling a condom from her pocket. She tore it open and rolled it onto my hard cock, her fingers warm and steady. Then she leaned in and started sucking, her lips wrapping tight around the base. She was so good—her tongue sliding along the underside, bobbing her head slowed at first, then faster. Wet slurps filled the air as she took me deep, her cheeks hollowing. I groaned, gripping her hair, but I wanted more. I needed to fuck her.

'I want to fuck you,' I panted, pulling her up. She stood and slid her pants down, turning her back to me. Her ass was smooth and round, curving just right in the moonlight. I grabbed my condom-covered dick and pressed the tip against her asshole, trying to push in. But she stopped me quickly, twisting around with a shout. 'Wait! Why are you going in the wrong hole?' Her voice was sharp but not angry, more surprised.

I froze, confused and embarrassed. 'If not your asshole, then where? You don't have a pussy,' I said, my heart pounding. To my shock, she turned fully, her eyes meeting mine. 'Yes, I do have a pussy.' I reached down, my fingers trembling, and touched between her legs. There it was—soft, wet folds, her pussy already slick. I slid a finger along her slit, feeling the warmth and moisture. 'I thought you were a trans without one,' I muttered, my mind blown. She smiled shyly. 'It's my first day out here. You're my first customer ever.' That hit me hard.

I was so happy, my cock twitching again. She bent over in doggy style, holding onto a nearby tree for support, her ass and pussy exposed in the dark. I started fingering her pussy slowly, one finger slipping in easily because she was so wet. Her juices coated my hand as I curled my finger inside, rubbing her walls. She gasped, pushing back against me, 'Ahhhhh,' she moaned. Her pussy clenched around my finger, hot and ready. I couldn't wait anymore. I positioned my hard dick at her entrance and thrust in, the condom sliding smooth into her wet pussy. She was tight, gripping me like a vice.

Out of nowhere, I was fucking her hard, my hips slamming against her ass. I reached around and grabbed her boobs, squeezing them vigorously, pinching her nipples as I pounded. The moonlight danced on her skin, and her moans mixed with the rustle of leaves. It was intense, my first time inside a pussy like this, and the surprise of it all made me thrust deeper. But after a few minutes, I got tired, my legs shaking from the nerves and the effort. My dick slipped out, softening a bit from the overwhelming excitement. She turned her head, thinking I'd cum. 'You okay?' she asked softly.

I nodded, embarrassed. 'Yeah, just nervous. It fell out.' She reached back, her hand gentle on my cock, stroking it lightly through the condom. 'Don't worry. I won't go or stop until you're satisfied. We can lie down if that makes you more comfortable, or even go to a hotel room nearby if you want.' Her sweet voice, full of kindness, washed over me. No one had ever been this understanding, not even my exes. It made my heart swell, and blood rushed back to my dick, getting me erect again.

I pulled her close, kissing her neck softly, my lips trailing down to her boobs. I sucked on them again, feeling her nipples harden under my tongue. She sighed, her body relaxing into me. Then she knelt once more, peeling off the used condom and sliding on a fresh one. She started sucking my dick, her mouth warm and eager, tongue working the head. This time, she didn't stop or pull back—she kept going, deeper and faster, her hand pumping the base. The sensation built quickly, her kindness and skill pushed me over. I couldn't hold it; I came hard, groaning as I shot into her mouth, the condom catching most but her swallowing what she could. She looked up at me with a smile, wiping her lips.

We caught our breath, and I took her number, already planning a full night out at a hotel. God, she was so sweet and nice with me. Even my exes weren't this caring. I walked away feeling lighter, excited for what came next.