One Night with Becky: Chapter 5

Jenna stood in my living room, her hands fidgeting with the hem of her shirt, looking around nervously. I approached her, trying to project a confidence I didn't quite feel. Scratch that—I didn’t feel any confidence whatsoever. But there was something else: a determination… and maybe a prayer that this would all somehow turn into something else. 

I reached out, my fingers brushing against her cheek, and leaned in for a kiss.

Jenna's lips were soft, but the kiss was tentative, almost hesitant. I could feel the tension in her body, the way she held herself stiffly, as if expecting me to change my mind at any moment. I deepened the kiss, my hands moving to her waist, pulling her closer. She let out a small gasp, and I took that as a sign to continue. Though something made me pause: a slight scratchiness from her chin: the arrival of her five o’clock shadow. Becky didn’t have that. Becky was surely taking pills to stop that; maybe with a combination of hair removal procedures.

My hands moved to her shirt, fumbling with the buttons as I tried to undress her. Jenna helped me, her fingers shaking slightly. As her shirt fell to the floor, my eyes were drawn to her chest. She wasn't wearing a bra, and her small, firm breasts were visible, but the sight of them was overshadowed by the broadness of her shoulders and the slight definition of her pectoral muscles. I swallowed hard, trying to push the thoughts from my mind. Jenna was a woman… like Becky. Maybe not quite as traditionally convincing, but just the same… Right?

Jenna's hands moved to her jeans, unbuttoning them and pushing them down her hips. I helped, my eyes fixed on the movement of her body. As her pants fell to the floor, I noticed the slight bulge in her underwear, a reminder of what lay beneath. I felt curiosity… and apprehension—a strange cocktail of emotions that left me feeling off-balance.

Jenna stepped out of her jeans, standing before me in nothing but her underwear. I reached out, my hands cupping her face as I leaned in for another kiss. This time, Jenna responded with more fervour, her lips parting, her tongue meeting mine. My hands moved down her body, tracing the lines of her muscles.

I broke away from the kiss, my breath ragged. "Let's go to the bedroom," I whispered, my voice cracking slightly. Jenna nodded, following me down the hall. The bedroom was small, the bed taking up most of the space. I turned to face Jenna, my eyes exploring her body, noticing more details that I probably didn’t want to take too long examining.

I reached out, hooking my fingers into the waistband of her underwear. Jenna held her breath as I slowly pulled them down, revealing her cock. It was semi-erect, the skin smooth and pale. My eyes widened slightly, taking in the sight. I reached out, my hand wrapping around her length, feeling the weight and warmth of her in my palm. She wasn’t big—not like Becky. In fact… Jenna’s cock was really small compared to her chunkier frame. With my fingers closed around it, it was lost, out of sight—though I could feel it. 

Jenna let out a soft moan, her hips bucking slightly. I leaned in, my lips brushing against the head of her cock. I could smell her now: a musky, almost too masculine scent that made my head spin. I hesitated for a moment, then took her into my mouth, my lips stretching around her girth.

Jenna's hands found my head, her fingers tangling in my hair as I began to move, my mouth sliding up and down her length. I could taste the salt of her pre-cum, the slight bitterness of her arousal. Jenna's moans filled the room, her hips moving in time with my motions. My nose kept pushing into her pubic hair—unshaved, probably for a few months now. That pubic hair spread just a bit too far down her thighs to seem really ‘feminine’. 

I pulled back, my lips glistening. I looked up at Jenna, her eyes glazed with desire. "I want you to fuck me," I said, my voice almost choking.

Jenna blinked, a look of surprise crossing her face. "But... I thought you wanted to be in control," she stammered.

I shook my head, a determination rising up inside of me. "No, I want you to fuck me. I want to feel you inside me."

“I’d really rather you do me,” she said, doe-eyed, looking more innocent than ever.

“Please,” I said. “Fuck me.” 

Jenna hesitated for a moment, then nodded, a forced small smile playing on her lips. She reached out, her hands moving to my clothes, undressing me with a shaky confidence. As I lay back on the bed, Jenna positioned herself between my legs, her cock hard and ready.

She leaned down, her lips meeting mine in a clumsy kiss as she pushed her small but fat cock into me, her hips moving slowly at first, then picking up speed. I gasped, my body adjusting to the intrusion, the sensation of fullness and pleasure mixing with the awkwardness of the situation. But she wasn’t quite big enough... Not nearly big enough. Becky had a full ten inches on Jenna. Ten inches. How can a person go from thirteen to just three? At least Jenna was hard. Her cock did curve in a pleasurable way. Maybe I could get used to it. It’s not about the size, right? It’s about how you use it; that’s what girls are always saying…

Jenna's movements were steady, her hips thrusting against mine, her cock sliding in and out of me with a wet, slapping sound. My hands gripped the sheets, my body arching off the bed as I met each thrust, my own cock hard and leaking now. It felt good. I closed my eyes, focussing. I wanted it to feel better. I wanted it to feel how it felt with Becky.

The room was filled with the sounds of our breathing, our moans, the occasional creak of the bed. I could feel the tension building, the pleasure coiling in my belly, ready to explode. Jenna's movements became more erratic, her hips snapping against mine, her cock pulsing inside me. “Jerk me off,” I moaned.

She took my penis and began to rub it. It wasn’t the elegant stroking Becky produced; this was much more clumsy, almost painful at times as she stretched my foreskin a bit too far back. But it still felt good—and it was enough to get me to where I needed to be. 

But then, she let out a groan of pleasure that betrayed her feminine identity. It was a deep, manly sound, sending a coldness into my spine. Then, she did it again, and again, her pleasure taking over. I tried not to cringe. It wasn’t her fault… but it wasn’t sexy. Now, her grip was stronger… manly. Her muscles flexed. Her small estrogen breasts looked more like… man-boobs. I tried not to look.

Then, with a final, deep thrust, Jenna came, her body shuddering, her cock pulsing as it released its thick, creamy load inside me. I followed soon after, my own orgasm pulsing, my cock spurting streams of cum onto my stomach.

It became quiet as she caught her breath—and then she shifted her posture back to a feminine one, which I could tell was still unnatural to her. 

As we lay there, I couldn't help but feel a sense of anticlimax. The spark I had been searching for was still missing, the connection I had hoped for still elusive. I had led her on… but for what?