Free Story Four

Written by Laiton Knight (2,500 words)

I am Kay. My husband Ray married me 15 years ago. We’ve always had a good sex life. With family commitments, it’s rare for us to be alone long enough to do much more than a quickie. We received an invitation to a Guys and Dolls fancy dress evening at a posh hotel. We have taken the opportunity to book a room at the hotel. I will go as a gangster, and Ray will dress as my moll. It should be a fun evening.
The thought of dressing up gets me excited. I love to play with my sexuality and I have always enjoyed role-play. Ray, my dear husband, is always open to trying new things. I catch his gaze and wink at him. “Hey, Moll, you look fucking hot,” I say, “I can’t wait to see you in that dressed as my woman.” He loves it when I talk dirty to him. It gets me wet every time. He runs his fingers through his hair, “I can’t wait either, big boy.”
We arrive at the hotel, and our room is perfect.
It has a separate bathroom, and the bed is large and inviting. I walk over to the window and look out over the picturesque countryside. A shiver runs down my spine as I imagine how it’s going to go.
Ray comes up behind me, wrapping his arms around my waist. “So, gangster, what’s the plan?” He whispers in my ear, his breath hot on my neck.
I turn to face him, a wicked smile spreading across my face.
“Well, Moll, first things first,” I say, reaching up to run my fingers through his hair. “We’ve got to get dressed for the party.”
Ray’s lips press into mine, his fingers tracing every curve of me. “I can’t wait to see you in that outfit.” He murmurs, his lips brushing against mine.
We spent the next hour getting ready for the party. I slipped into my gangster costume: a sharp black suit, crisp white shirt, and black fedora. Ray looked at me with lust in his eyes.
“You look fucking amazing, Kay,” he said, his voice low and gravelly. “Are you ready to take control?” I nodded, a thrill of excitement coursing through my veins.
I walked over to him, keeping my gaze fixed on his as I unbuttoned his shirt. He helped me take it off, revealing his muscular chest. I stroked his body, my nails scratching his skin with gentle pressure.
“I’ve missed this,” he said, his voice husky with desire. I moved closer to him, my body pressed against his.
I could feel his arousal through the fabric of his trousers. I reached down and ran my hand over his erection. “I can see that you’re ready, Moll,” I said, my voice low and sultry.
He groaned, his head falling back as I continued to touch him. “You have no idea, Kay.” He said, his voice strained with desire.
I broke away from the kiss. “We’ll have time for this later. Go and get dressed. I want to see you in your costume. I’m sure you will look sexy as fuck.”
He smiled at me and went into the bathroom, closing the door behind him. I took the opportunity to freshen up, and when he came out, I wasn’t disappointed. Ray looked hot in his 1920s-style dress, with a short bobbed wig and his red lipstick. His legs looked great in the stockings.
“Wow, you look amazing!” I said, my appreciation was clear in my voice.
“Now, let’s head down to the party.”
“Stay where you are. I have to add my finishing touches. And I disappeared into the bathroom.”
As we made our way to the elevator, I couldn’t help but grab his arse. The way he had done to me so many times over the years. .”
The music was pumping, the room was starting to fill, and the excitable chatter bounced off the walls. I scanned the room for our. I saw an unoccupied table in the corner with a sign ‘reserved for Kay and Ray’. I made my way over with Ray following close behind. We ordered a bottle of champagne and settled in for the evening.
As we sat and watched the crowd, I couldn’t help but feel a growing attraction towards Ray. I slid my hand onto his thigh, feeling his muscles tense underneath my touch. I leaned close to him, my lips brushing against his ear, “I can’t wait to get you alone.” I whispered, “I’ve got to have you now, Moll.”
The party was in full swing as Ray and I sat at our table, sipping champagne. Laughter and music filled the room, creating an electric atmosphere.
My thoughts were racing. I felt a growing excitement as I looked at Ray, the man I loved, dressed as a woman. His wig shone under the dim lights. The 1920s dress he wore made his feminine appearance stand out.
We exchanged playful glances as we bantered back and forth. The alcohol loosened our inhibitions. We both became enthusiastic about our new roles.
The night went on. The party was in full swing. We engaged in sexy banter, laughing and enjoying our time together. Ray was completely oblivious. I was very serious about taking on the role switching all evening.
I slid my hand onto Ray’s thigh. I felt his muscles tense under my touch. I felt the clasp of a suspender through his thin dress. I whispered, “I need you now, Moll.”
I leaned in closer, my lips brushing against his ear. Ray turned to face me, his eyes filled with confusion. He lowered his voice, trying to keep up the act as he asked, “What do you mean, Kay?” But I could tell he was starting to pick up on my hints. I flashed a charming grin and told Ray, “Don’t bother with that.” Let’s finish our champagne and enjoy the party.”
I watched as the alcohol started to take effect on Ray, making him more relaxed and disinhibited.
His eyes were glassy and his movements were slow. But, he still managed to banter with the other guests at the party. He even played the part when another ‘Gangster’ tried to chat him up. One look from me soon made her scamper off. The music got louder, and the dancers took to the floor in a whirl of fabrics and feverish movement.
I couldn’t help but feel a sense of anticipation building inside me. I had never taken the initiative like this before. The role switch ignited an intense excitement that consumed me completely. It was time to make my move.
“Hey, Moll,” I commanded to Ray as he returned from a toilet break.
The music shifted to a slow and sultry tune, and the room became quieter. “Sit down,” I said. He sat. His face showed confusion and curiosity.
I sat beside him, running my fingers along the curves of his dress and the stockings that held them up. He fixed me with an intense gaze, his eyes wide open.
I leaned in to whisper in his ear, feeling the warmth of his skin against mine. “I want you, Moll. Now,” I whispered. His cheeks flushed, and his eyes gleamed with desire. “Here? Now?” He spoke in a soft, hushed tone.
“No. “Let’s go back to our room,” I murmured, running my hands up and down his thighs. I avoided his groin because a woman doesn’t have a cock.
I glanced around the room, and everything else seemed to fade into obscurity.
In the elevator, my hands were all over him. Touching his bare flesh above the tops of his stockings. “I want you, Molly. I want to fuck you hard.” I breathed a sharp tone into his ear. Ray grasped the situation, and a surge of adrenaline flooded his veins. He clutched the elevator rail, his muscles contracting.
“Are you sure, Kay?” He asked, his voice trembling with a mix of fear and excitement. “I’ve never… I’ve never done this before.”
I smiled at him, feeling a wave of confidence wash over me. “I’m not Kay. I am your gangster lover, who is going to take your virginity. You can call me Ronny. And don’t worry, I’ll guide you through it.” I promised.
With that, I took Ray’s hand in mine and led him towards the hotel room. I couldn’t help but feel a sense of power as I walked ahead of him, his eyes on me, watching as I moved.
We arrived at the hotel room door, and I slid the key card into the lock, pushing the door open. I turned to face Ray, standing in the doorway, looking unsure. I moved close to him, grasping his shoulders, and pressed my lips to his.
I could feel him relax in my arms, his body surrendering to mine. I broke the kiss, stepping back to take in the sight of him. His messy wig and smudged makeup caught my attention. But, it’s his eyes that captivated me. A mix of fear and anticipation filled them, and I wanted to devour him whole.
“You’re beautiful, Molly,” I whispered, my voice low and sultry. “I can’t wait to make you mine.”
I kissed him again, my hands exploring his body as I undressed him. I removed my jacket and shirt before pushing him hard onto the bed. He looked so sweet in his balloon-filled bra, lacy knickers and suspenders.
I traced my fingers along the curve of his hip bone and ran my thumb over the frilly edge of his knickers. He jerked back and gazed at me with astonished eyes, struggling with intoxication. I couldn’t help but laugh at the adorableness of it all.
“You’re mine now, my now, you little slut,” I said, smirking. “You are mine to do with as I please.”
He looked nervous but excited. I could see it in his eyes. This role switch, our little game, was doing something to him. I stood to remove my trousers, and as they slid to the floor, Ray spotted it. “What the…” he trailed off. He looked bewildered, but there was also a flicker of fear in his eyes—pure, raw, honest fear.
I lay on top of him and forced his wrists to the side of his head. I could feel his erection, so he must have felt my surprise package pushing against him.
“What the hell?” He stammered, his eyes searching for an explanation. His bewilderment shifted to terror, as he realized I held him trapped. With a grinning smile and a twinkle in my eye, I leaned in close and whispered, “You know what this is, Molly. I’ve been dying to have you since the first time I laid eyes on you. I’m going to take your virginity.”
I stood up and removed my boxer shorts to reveal my strap-on. Rays erect cock was peeking over the top of his lacey knickers. “Suck it, Molly,” I ordered.
My tone was commanding but gentle, laced with a hint of playfulness that I knew he would appreciate. He hesitated for a moment, unsure. But then he followed my instructions. His mouth wrapped around the artificial penis with intense desire. I could feel the moisture between my legs start to flow.
I closed my eyes. I imagined the feeling of his warm mouth. His tongue darted around the fake shaft, giving me waves of pleasure. I couldn’t stop the moan that escaped my lips. He was going faster, sucking me with a fervour that defied his inexperience.
I opened my eyes and saw the stunned look on Ray’s face as he worked to pleasure me. He was still in the lingerie. But, now he was on his knees. His head bobbed up and down in front of me as he took me into his mouth.
I placed my hand on the back of his head, trying to pull him away. “Turn around and bend over,” I commanded.
He obeyed, the curves of his bottom accentuated by the frilly knickers. I ran my hands over the lacy fabric, feeling him shudder underneath my touch.
I wrapped my arm around his waist, pulling him tight against me as I reached down to adjust the strap-on. I could feel his heart pounding against my hands. Fear and excitement mixed as I pressed my lips against his bare shoulder.
“Relax, Molly,” I whispered, my voice low and reassuring. “I know it’s your first time, but I will be gentle with you,” I reassured Ray.
I sensed his body relax, and I seized the opportunity to enter him. He flinched, and I seized him in a tight grip. I whispered soothing phrases in his ear. “Breathe, Molly. It’s going to get easier. Let yourself feel it.”
I drizzled some oil onto my plastic cock. I established a pace. I found a rhythm that brings intense pleasure with every thrust.
I wrapped my other arm around Ray’s waist, pulling him closer as I increased my pace.
The sounds of our bodies slapping against each other filled the room. He was moaning softly, his body trembling as I filled him up over and over again. With each thrust, I sensed his muscles tightening around my cock. The thought sent pleasure through my body.
I leaned forward, pressing my lips against Ray’s ear. “Let go, Molly,” I whispered, my voice strained with pleasure.
My hand tightened on his shoulder as I felt him shift beneath me, his body relaxing in surrender. He groaned as his orgasm overtook him. “Go on, Molly, cum for me. He expelled a heavy breath as semen spilled onto the bed sheets.
I could feel myself following him. Tension built in my body before exploding in ecstasy. We lay there breathing heavily, our bodies glistening with sweat and perspiration.
A smile tugged at the corners of my mouth as I looked down at Ray. I had never seen him so vulnerable before. His dishevelled appearance and cloudy eyes spoke volumes about his experience.
I planted a few kisses on his forehead before propping myself up on my elbow. My plastic cock pointed right at him. The lubrication on it glistened from the reflected light in the room.
There was silence for a long moment, and I wondered if I had crossed the line. But then he turned towards me, his eyes shining with a mixture of emotions, and I knew everything was okay.
“Thanks, Ronny,” he said quietly.
“For what?” I asked, genuinely curious.
“For taking charge tonight. For being the man to take my virginity.”
I gave him a gentle smile. “Well, Molly, I’m glad you liked it. Now I can fuck you anytime you feel like it.”
He returned my smile and pulled me close for another kiss, this one gentle and tender.
“You are an amazing woman, Ronny,” he murmured, his breath warm against my cheek.
“Fucking amazing,” I replied, tipping my head to kiss him again. Our bodies melded together, and I felt a warmth spread through me as his hands caressed my shoulders.
We spent the rest of the night exploring one another. Experimenting with new positions. And sharing a deep intimacy that I had never experienced before. Each touch, each kiss, was a way for us to reaffirm our love for each other.