Sissy Becky Chapter Two

Standing in front of the motel mirror, I told myself inwardly that I had done my best. I couldn't see what more I could do with the skills, knowledge, and experience I had at my disposal. Checking over my personal transformation from Ben the nineteen-year-old student to SissyBecky, I could only hope and pray that Richard would like me.

After years of secretly cross dressing in my mothers clothes and lingerie, progressing to buying my own feminine wear and accessories, turning myself into a sissy, I had finally taken the plunge and agreed to meet a man I'd met online. It was an exciting yet terrifying prospect, but the lust and desire, the need inside of me, had me hooked, giving me the courage to secretly meet.

Richard was charming, friendly, and very understanding. The fact he was in his late-forties didn't bother me. He was fairly handsome with a clean shaven face, brown eyes, and a brown faux hawk hairstyle. He knew it was my first time meeting anyone as Becky. He promised I didn't have to do anything I didn't feel comfortable doing, and that we would go at my pace if we did stuff.

However, as per his polite request, I was dressed in full sissy mode, leaving little to the imagination. My outfit was new and wild, trying to be the kind of sissy I longed to be. I wore a tight, pink PVC, corset dress that pushed my DD breast forms together, creating a cleavage that I was very proud of.

The corset part of the outfit hugged my body and waist, emphasising my slender frame, while the short flared skirt showed off my smooth legs. I was stood in a pair of pink, sky-high stiletto heels, the kind that made my calves burn, but they were obviously essential, adding to the overall sexiness of the outfit and sissy look.

I thought my makeup was the best I'd done to date. Heavy foundation smoothed out my skin, contouring accentuated my cheekbones, and a bold red lipstick drew attention to my mouth. My eyes were the focal point, though, with long fluttery lashes and smoky eyeshadow that made my blue eyes pop. I had a set of long, red, almond-shaped false nails, matching my sissy lips.

The final touches, a pink plastic chastity vagina cage that was locked around my cock, a constant reminder of my submission, and the fact that I was not in control. And last but not least, I wore my favourite long, wavy, platinum blonde wig. I loved smoothing it into place and twirling a few strands with a finger, dreaming like a sissy.

I looked like a living doll, a sissy slut ready to be played with, but I felt anxious, sexy and anxious. I couldn't shake the thought of Richard not liking me, and I didn't know what I was going to do if he did. Both scenarios sent shivers down my spine. I took a few deep breaths, trying to calm my racing heart and mind. It's all I could do as I waited.

When the knock finally came, it made me jump and start panicking. I took one last look in the mirror before hurrying to answer it. My hands were shaking as I unlocked the door and pulled it open, revealing the man I'd met online, the man I dared to meet. His handsome smile spread across his face as his eyes gleamed, taking in my appearance.

"Wow," he breathed, stepping inside the room. I quickly closed the door and turned around to face him. "You look incredible, Becky. Better than the photos you sent me."

His words sent a thrill through my body. I felt my cheeks blushing under all the makeup too. "Thanks, Richard," I murmured, my voice soft and submissive, weak and sissy.

I wanted to compliment his good looks and nice clothes, but I was too shy and nervous. He stood taller than me, even in my heels, and he was broad, giving off an air of confidence that made my knees weak. He stepped towards me and cupped my face gently, smiling into my pretty blue eyes.

"Can I kiss you, Becky?" he whispered.

"Yes," I sighed, ready to kiss my first man.

Without another word, Richard took me into his arms and kissed me as if I were a girl. I melted into his masculinity, my lips parting as his tongue entered my mouth. His hands held my waist, pulling me closer, my fake tits pressing against his chest. I moaned into his mouth, my hands reaching to grip his shoulders, my false nails digging in as I returned his kiss with equal passion.

When we eventually broke apart, I was breathless and dazed. Richard grinned knowingly at my reaction, his eyes sparkling with desire and appreciation. I exhaled a deep sigh and fanned my face with my hand, causing us to break out laughing together.

"What do you feel like doing, Becky?" he asked curiously. "Would you like to sit on the bed and kiss again?" Absently, my eyes gravitated towards his crotch. "Or do you have something else in mind," he smirked.

"I have something else in mind," I blushed, getting down on my knees in front of him, eager to see, feel, and suck his cock.

"Good girl," he chuckled.

I didn't hesitate. The situation aroused me like crazy. I reached for his belt and undid it, then I unzipped his jeans, letting them fall to the floor. Richard's magnificent cock sprang free, thick and hard, above average, the head begging to be sucked. I licked my lips and wrapped a hand around his pulsating shaft, my eyes wide with desire.

"It's big," I giggled.

Richard chuckled once more, gazing down at me. "It's not as big as you think, but thanks. He's all yours, Becky."

"Mmm, I like the sound of that," I replied.

I leaned forward and kissed the tip, then licked it, tasting cock for the first time in my life. It was intoxicating. I swirled my tongue around the head, submitting to the salty taste of his pre-cum before taking him into my mouth. Everything felt perfect.

"Oh, that's it, Becky, suck it good, baby," Richard sighed as I moaned around his shaft, the sound vibrating against his hard cock.

I began to bob my head, taking him deeper. He squeezed my fake tits, groaning, then ran his fingers through my platinum blonde waves, gently holding my head as he moved his hips in rhythm with my mouth, slowly fucking my face. It was sublime. I felt like a real girl, a little slut sucking a strangers cock in a motel room, eager for his validation.

"Oh, you have such an amazing mouth, Becky. It feels fucking awesome. Suck it."

I moaned in response, gripping his thighs as he stretched my mouth, my nose pressing against his trimmed, dark pubic hair. It wasn't brutal, but it was controlled and dominant. I used my tongue to lick and suck, hollowing my cheeks to create a tighter suction that had him cursing and fucking my mouth, taking him to the brink of climax.

"Stop," he gasped, pulling me off his cock.

"What's wrong?" I asked, hoping I hadn't done something that had displeased him.

Richard hauled me to my feet. "Nothing is wrong. You're amazing," he said, shoving his tongue down my throat, his hands going under my skirt and grabbing my buttocks.

"What do you want to do?" I asked, my heart pounding. The answer was in his eyes.

"I want to be your first everything. Would you do me that honour, Becky?" he asked, his voice deadly serious. "I promise to be gentle with you, and treat you right.

"Oh fuck," I sighed.

I was so nervous, but I really did want to get fucked. I didn't see the point in just sucking him off. He was here now. I trusted him, felt safe with him. I was going to lose my cherry.

"Ok," I nodded. "I want you to be my first."

"Thank you," he beamed, plundering my mouth with his tongue. "Bend over the bed," he then instructed. "I want to eat your tight pussy and get you ready for me."

I climbed onto the bed, positioning myself on all fours like a bitch in heat. Richard flipped the hemline of my flared skirt up, exposing my most private parts. He ran his hands over my smooth buttocks, spreading my cheeks to inspect my puckered virgin hole and chastity.

"You're perfect, Becky," he said in a husky voice. "I'm going to enjoy rimming you."

Before I could respond, Richard dropped to his knees, keeping my cheeks spread, and ran the flat of his tongue along my crack. I jolted forward, moaning, my hands gripping the bedcovers. He did it again and again, before getting his tongue right into me. I closed my eyes and pushed back, enjoying the new sensations that I hadn't felt before.

After rimming me for a few minutes, he then slipped a finger inside my body, thrusting gently, slowly, gradually increasing the pace. I could feel my locked dicklet weeping with delirious excitement. I wanted to climax, but Richard was only preparing me, preparing me to lose my sissy virginity with his cock.

"No pressure, Becky, but I'd love to take you bare for your first time," he confessed. "I wouldn't usually, but I know I'm clean and I trust you've never been fucked before."

"Um..." I hesitated. I had lube and condoms in the drawer, just in case. "I don't know."

"Maybe you could do it just this once?" he smiled, running his engorged tip across my hole, teasing me dangerously, exciting me. "Don't you want to feel me filling you up?"

"Yes," I sighed, closing my eyes, focussing on the wonderful feeling at my entrance. "But..." I hesitated, not sure why anymore.

"It's up to you, princess?" he whispered, taunting me with his cock. "Come on, Becky, I'll show you what it feels like to be a girl."

Oh God, I quivered on the bed, my ultimate fantasy. "Do it," I groaned. "Do me bare."

"There's a good sissy," he grinned in triumph, pushing his cock against my hole.

"Lube?" I gasped.

"I lubed you good and proper with my tongue," he replied, squeezing his cock into my body, stretching my hole like my dildo, only it was real, raw, and so much better.

"Oh fuck! Richard! Oh fuck!" I cried out.

"Mmm, so tight around my cock, Becky. Put your head down and your ass up," he instructed, pushing down on my back. "That's it, now enjoy me fucking you like a girl."

"Oh yes! Fuck me! Oh my God I'm getting fucked," I whimpered into the bed.

"Damn right you are," he groaned, holding my hips as he fucked me with slow, deep strokes. "Oh, that's one tight pussy, Becky."

Making all kinds of noises on the bed as I adjusted to the stretch, I fell in love with the sensation of getting fucked, with the fantasy that I really was a girl. Richard was amazing. After a while, he started pulling out slowly and then slamming back into me, fucking me hard and deep. Filthy sounds filled the room, mixed with my girly, sissy groans.

I became a mess, my body trembling as I eventually took everything he had to give. My breast forms bounced with each thrust, and my fingers tangled in the sheets, trying to anchor myself. Richard simply kept hold of my hips and pounded me deeper.

"You like that, don't you, Becky?" he growled. "Taking my hard cock like a girl."

"Yes," I moaned. "I love it. Cum inside me."

He chuckled, a dark, dirty sound before slamming into me harder, his hips pounding against my ass. "I'm going to fill you up."

The image his promise painted in my head made me cry out louder. I pushed back to meet his thrusts, urging him to fill me with his warm cum. I wasn't sure how much more I could take. But I wasn't quitting. The burning had long given way to pure bliss. I was determined to be a good sissy for him.

"I can't wait to feel it," I moaned. "God, I wanna feel it shooting deep inside me."

My internal walls suddenly tightened around him, triggering a primal need to stroke my clit, but I couldn't. I was locked up and at Richard's mercy. Then I realised I was on the brink of something special. I buzzed with excitement, moaned louder with anticipation. I was so close, so needy, so ready for it... my first sissygasm.

"Get ready, Becky," Richard grunted. "Get ready to feel my cock filling you with cum."

With a hoarse sound, he climaxed and began to shoot his masculine load into my sissy hole, pounding me so deep I wailed with every rope he fired into the depths of my trembling body. I felt him twitching and throbbing, emptying his balls until he had nothing left, totally spent. I sadly didn't get to climax. Richard took me right to the edge, but I couldn't quite get over the line.

"You're a good sissy, Becky," he sighed, withdrawing his cock. "A very good sissy."

I collapsed onto the bed in a heap, hot and sweaty, recovering my breath while Richard went to the bathroom to clean himself up. I'd done it. I'd met and man, sucked my first cock, and let him fuck me bareback. His cum was deep inside me, messing with my pregnancy fantasies. For my age, I was screwed up, but it felt good, it felt right.

Reality dawned when Richard left without kissing me. I understood. He was satisfied until the next time. Now we had each others phone numbers, he promised to call me soon, insisting upon meeting again. I told him I was already looking forward to it. I then unlocked my clit and assumed the position, jerking off over my face.

After taking a shower, I changed back into Ben and went outside the motel for some food. I stayed the night on my own, falling asleep in my classic pink and white sissy romper. I didn't think, I just slept, making sure Becky got plenty of rest. My journey as a sissy had truly begun, and I was thrilled, eagerly awaiting my next experience.