Cindy’s Journey Pt. 5

I had been seeing Scott for more than a month, and we got along well. You wouldn't call what we had a relationship. It was more of an "arrangement" that we found agreeable. I knew that Scott liked turning out effeminate young boys. After all, that's how we got involved.

Scott knew that he was too old for me, but the sex was great. I loved how he fucked me. Of course, I had no basis for comparison, because I had never had sex with anyone but Scott. That was about to change.

Every time I had been at Scott's house there was a party going on. I almost always heard voices and music coming from the living room. Scott never introduced me to the partygoers, he just hustled me into his bedroom, which was where I wanted to be.

I had become used to coming and going freely, and always dressed in girly clothes with makeup. I had worked up the nerve to visit the local mall, and bought a small collection of skirts and tops, claiming that I was buying for my girlfriend. "Yeah, right," I could hear the clerks mutter under their breath. Increasingly, I found that I didn't care what the clerks thought.

For weeks, I showed up at Scott's house and found him available and ready for sex. One Saturday night, however, I went to the house and found Scott's bedroom door closed, which I knew meant that he was with someone. Fighting to supress feelings of jealousy, I turned to my right, where I heard voices coming from the living room.

I came face-to-face, and almost collided with Steven, whom I had met briefly about a month ago. My heart jumped into my throat as I blurted out, "S-Sorry. Oh, Steven. Hi. It's Cindy."

"I remember you, Gorgeous. Is your stud muffin busy with someone else?"

"Apparently," I said, barely trying to conceal my annoyance.

"You look luscious. why don't you come in and join the party?"

He looked me over in a way that I had seen straight guys look over real girls they wanted to fuck, and I felt an ego rush come over me. "Sure. Lead the way." I held out my hand and he took it in his with a little squeeze that reminded me of our first meeting.

I was wearing one of the outfits I had recently bought, intending to show it off to Scott. A black denim miniskirt with a frayed hem, sheer black top and four-inch black heels. My makeup was the slutty look that I was becoming good at. The overall look just screamed SISSY SLUT. I felt butterflies as I turned the corner into the living room and held tighter to Steven's hand.

"Everyone, say hello to Cindy. Scott dissed her, so she wants to party with us tonight."

A chorus of laughter and "hello Cindys" filled the room.

I surveyed the room, which was full of men, with the exception of two boys about my age, who were clearly sissies. There were 10 people in all, sitting on two large couches and two overstuffed arm chairs. There was one place to sit, at the far end of the couch against the wall to our right. Steven led me across to the open seat, sat down and pulled me onto his lap.

Steven opened his legs and my butt sank down between them. My skirt slid up my thighs, leaving my black thong clearly visible to at least half the room. I felt myself blush, but also felt aroused as the men all turned to ogle me. Steven put a hand on my thigh and began rubbing up and down. I wrapped my arms around his neck and leaned in to nibble on his earlobe.

A joint was passed around the room, and when it came to me, I took a long hit and offered it to the man sitting next to us. He said, "Take another hit, Cindy. You need to catch up."

I took another hit and passed the joint back to the man. He took a hit and passed the joint on, then casually laid a hand on my left thigh and began slowly rubbing up and down, stopping just short of my thong each time.

Another joint came around, and I took a deep hit. I was totally stoned at this point, and felt like a complete slut, in a room full of men with my skirt hiked up to the top of my thighs and two men groping me. It felt so good, I wasn't the least bit embarrassed or ashamed. Besides, I assumed that everyone in the room knew I had been fucking Scott for the past month. I imagined they all thought of me as a slut. I giggled as I realized that I didn't care.

"What's so funny?" Steven asked with an obviously stoned look in his eyes.

"You, ya stoner," I replied. "Look at your eyes!"

He laughed as he pulled my face toward his and kissed me. "Let's get outta here before Scott comes out and rains on our picnic."

"My thoughts exactly." I giggled and slid off his lap and gave the man on my left a kiss on the cheek as a thank you for helping to make me the center of attention. He high-fived Steven as we made our way out of the living room. I had no trouble imagining what that little celebration was about.

Out behind the house, we leaned on my car and kissed. I could feel Steven's cock getting hard in his pants, and I knew he wanted me. My little cocklet was straining against the chastity cage, but I thought of all the sissygasms I had experienced with Scott, and decided to keep it on.

Steven asked, "Do you want to go to my apartment?"

Since I had left the key to my cage at my apartment, that was exactly where I wanted to go. "Okay, lead the way."

We got in our separate cars and headed for Steven's apartment, which was a short drive. I was still feeling a euphoric high from the weed, and so was glad that I didn't have to drive far.

We both parked on the street, and I hooked my arm in Steven's for the walk to his building. His building was in a busy neighborhood, and there were lots of people on the street. I felt very safe with Steven. He was a substantial man, and walked with confidence.

Steven lived in a high rise, and we kissed in the elevator on the way to his apartment. His kisses were passionate, but with a tender quality. I entertained high hopes that his lovemaking would have the same quality.

Steven's apartment was nice -- much nicer than mine. The tastefully furnished living room was dimly lit, which I found very romantic. There was a balcony that ran the full length of the far wall, and featured a breathtaking view of the downtown skyline.

"Steven, the view is magnificent!"

"Thanks, Cindy. I was lucky to get it. I was on a waiting list for two years." He took my hand and led me to the couch. "Sit, please. Can I get you something to drink?"

"Some water would be great." I watched him move across the room toward the kitchen, and let myself smile at the curve of his ass in his tight jeans. Was that a low moan that escaped my lips? I slipped off my heels and leaned back into the plush couch as Steven returned from the kitchen with two glasses of water.

He handed one of the glasses to me and settled into the corner next to me, placing his hand on my thigh and giving it a gentle squeeze. I set my glass on the coffee table, wrapped my arms around his neck and leaned in for a kiss.

Our lips met and I felt electricity travel up my spine. Our tongues swirled around each other, and I moved closer, running my hand down Steven's muscular chest and rubbing his thigh. The slut in me wanted to squeeze his cock, which I could see growing in his jeans, but I resisted the urge. I wanted Steven to take the lead.

I didn't have to wait long, as I felt Steven's hand slide up my thigh and under my skirt to fondle my chastity cage. My body shuddered and I moaned softly at his touch. "Mmmm." My breathing became faster as our kisses became more passionate.

I felt Steven's mouth on my neck, sucking and gently chewing on my soft skin. Chills ran throughout my body as I heard him breathe in my ear, "I want you, Cindy."

"Oh god, yes, Steven." My words were barely audible.

Steven stood up, took my hand and started to lead me across the room. My bare feet padded quietly behind him, across area rugs, then tile, and into the softness of thick bedroom carpet.

Our bodies pressed together as our lips met, and I felt Steven's hand drift down and start unbuttoning my top. I shrugged out of it and let it drop to the carpet.

I unbuttoned his shirt and pushed it off his shoulders, and smiled at his lean, muscular frame. I fumbled with his belt, and then the top button of his jeans.

Steven helped me pull his jeans down his muscular thighs while I slipped my fingers into the waistband of his briefs. I smiled as I slid his briefs down over his firm ass, giving his butt cheeks a playful squeeze.

Steven's cock was fully erect, and was impressive. I guessed it to be 7 inches and just girthy enough to stretch my little pussy. I put my hand around his cock and squeezed, causing him to moan. He reached for the button on my skirt, and soon it joined my top in a loose pile on the carpet.

I pressed my body against Steven's as we kissed again. I could feel his hard cock throbbing against me as he gripped my butt and started grinding his hips. "You have a terrific little ass, Cindy," he said as he continued to grind his hips and massage my ass.

I moaned softly as I felt his strong arms pull me tighter against him. I wrapped my arms and legs around his back as I felt him lift me up and lay me on the bed. He hooked his fingers into my thong and slowly pulled it down my legs and sent it to the floor.

My cocklet was throbbing in its cage, and the only thing in the world I wanted was to feel Steven's skin against mine. I opened my legs to invite him in, and he stepped forward, crawled onto the bed and settled in between my open legs. I moaned deeply and wrapped my legs around his back, pulling him tighter to my trembling body.

Steven nibbled on my neck and earlobe, causing chills to run the length of my spine, then slowly moved down to kiss my swollen nipples. My breathing became shallow and low moans escaped my throat. Steven was clearly an expert at building sexual tension, and I smiled at being the beneficiary of his expertise.

My fingers were running through his thick black hair as I felt his kisses travel down my torso, across my cage and to my waiting pucker. I opened my legs wide, and he pressed his tongue at my opening and swirled it around and inside me.

"Oh god, Steven," I gushed, "that's so good!" I pulled his head tighter to me, and he pushed his tongue deeper into my willing pussy. My whole body was trembling and I was breathing heavily.

Steven raised himself up until we were face-to-face, and smiled. "You like that, Baby?"

"Fuck!" I was still breathing heavily. "That was incredible. You're incredible."

Steven grinned. "You ready to take some cock?"

I could feel his hard cock throbbing against my lower abdomen as I exhaled and rolled my eyes toward the ceiling. "God, Steven, I'm more than ready."

Steven reached for a bottle of lube on the bedside table and spread some on his fingers. My pucker felt like I could take his cock without lube, but I reminded myself that I was relatively new to this life, and lube was probably a good idea.

I relaxed my pucker as I felt Steven push one finger in, and then a second finger. I kept my eyes locked on his as he ran his fingers in and out of me, stretching them apart to open me.

He kissed me as he pulled his fingers out of me and rubbed lube on his fully erect cock. He moved in between my legs, and I opened them wide, inviting him to enter me. My legs were quivering and my breathing was shallow.

I felt the head of Steven's cock press against my slippery pucker, and then the pressure as he pushed inside me. The pain was nothing compared to the pleasure I felt.

"Ohhh, oh yes Baby."

I wanted more and Steven knew it. He pushed his cock into me steadily but slowly, until every inch was inside me.

"Mmmmm. Oh god. Ohhhh." His cock felt so good, I could scarcely contain myself. I begged him to fuck me. My pussy ached as he began to pull out and then push all the way back in, slowly but steadily, causing me to moan loudly.

I was still looking into his eyes as I felt his pace increase. Soon enough, he was pounding my pussy mercilessly as I moaned and writhed beneath him. I relaxed my body as much as possible, and opened my legs wide to let his hips slam into me.

After just a couple of minutes of this intense fucking, I heard a deep, gutteral moan come from him, and his hips start to gyrate. "Can I come in you?" After a banging like he had just given me, how could I say no?

"Yes, Baby. Please come in me." My voice was raspy and desperate.

I felt his hips slam into me one more time, and my guts were flooded with his hot seed. We looked at each other and laughed, then melted into a kiss unlike any I had felt before.

We used separate bathrooms to clean up. I found a robe, which I wrapped around myself and went back to the living room to find Steven waiting on the couch. He patted the space next to him and said, "Come here, sweetheart." I curled up next to him, and felt his arm wrapped around me. We kissed some more, and talked about how great the sex was.

I suddenly felt very sleepy. "I'd better go, Steven, I said sleepily. It's late."

"It's after 2:00 a. m., Cindy. You don't want to be out dressed the way you were earlier at bar closing time. Why don't you stay?"

I felt my stomach jump. Spending the night with a man was a big deal, and honestly, something that I had never contemplated. Still, Steven was right about the way I was dressed. At this hour, I couldn't count on finding a parking spot close to my apartment. The thought of walking two or three blocks dressed like a hooker didn't appeal to me. I agreed to stay.

We crawled into Steven's king-size bed and cuddled, which led to sex. The thick sheets and plush pillows made it easy to fall asleep. Steven woke me up two more times for sex; the last time just before dawn. After that, we both fell into a deep sleep, and woke up after 10:00 a. m.

"Good morning, Love," I heard him say."

"Good morning, Sexy."

Steven slid over, wrapped his arms around me and proceeded to nibble my neck. It felt so good that it got a low moan out of me. I knew that I couldn't stay, however, because it was a work day and I had to change to boy mode.

"I can't, Baby. I have to go to work," I whined.

"Yeah, me too," he conceded. He slapped my ass playfully, jumped out of the bed and headed for the bathroom.

I spun out of bed, collected my clothes from the floor and headed for the bathroom I had used last night. I washed my face and re-did my makeup; not so slutty as before. I put my clothes on and looked in the mirror. I looked like a sissy slut coming from a night of fucking.

I met Steven in the living room, and he looked at me with a sideways grin and said, "Next time, you'll know to bring a change of clothes." His expression changed as he asked, "Will there be a next time?"

I put my arms around his neck and looked into his eyes. "Do you want there to be a next time?"

"Do you want us to be a couple?" There was a note of earnestness in his voice.

I asked, "Is that what you want?"

"I asked you first," he said with a laugh. "I know it's still early for us, but I'd like to know what you're thinking."

I thought for a second and said, "Obviously, I'm attracted to you, and you're an unbelievably talented lover, but that's all I know about you. Ask me again when we get to know each other a little better."

Steven smiled and said, "Fair enough, Cindy." We kissed lovingly, and I headed home, my thoughts lighter than air.

It was almost noon when I pulled into a parking spot about a block from my apartment building. There weren't a ton of people on the street, but there were enough people to give me anxiety abot how I was dressed.

I took a deep breath, stepped out of my car and started walking. I held my head up and looked people in the eyes as we passed. Most simply looked me up and down and kept walking. A few grunted in disgust.

When I got into my building, I turned down the hallway toward my apartment and noticed one of my neighbors leaving his apartment. It was the same man who had seen me leaving my apartment a couple weeks earlier, dressed in my homemade denim skirt.

"Hi neighbor," he said in a friendly voice. "You live at the end of the hall. My name's Chad." He held out his hand.

I shook his hand daintily. "Cindy," I said. "Nice to meet you." I noticed that Chad was well-dressed and wore nice shoes. Girls always notice a guy's shoes.

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"Well, I'm on my way back to work. Again, it was nice meeting you, and if you ever need anything, just knock."

"Okay, Chad, see you around."

"See you, Cindy."

I stepped into my apartment and thought to myself, "Hmm. He's kinda cute..."