My First Time as a Sissy Ch. 03

I suggest you read the first two chapters before reading this one.

I was coming to the realization I was a natural born sissy. I had sucked Raoul's cock a few times and had been feminized with the help of his sisters. I found I loved being feminine, specially wearing the clothes and makeup and I loved sucking Raoul's cock. I wasn't completely "out," yet but, I had developed a more androgynous look in my daily life. I wore more feminine clothing, had fairly long styled long hair and wore at least light makeup.

I knew after my last time with Raoul that he wanted to take my sissy cherry and I wanted him to. I had bought a dildo and butt plug when shopping with his sisters. I wore the plug regularly and was practicing with the dildo every night and really enjoying it.

Raoul called me and said he wanted to take me out on a date. I gladly said yes. I had given Raoul blowjobs but, had never been out with him. I was giddy with excitement. He said he would pick me up Friday at about seven. I hung up the phone lightheaded with happiness.

I got out of class early and went home to prepare for Raoul. I took a long bath with a scented oil. I shaved to remove any body hair, even though I didn't have too much. I moisturized to make my skin as soft as I could, paying particular attention to my ass.

I then got dressed for Raoul. I had spoken to his sisters about what he liked women to wear and I tried to comply. I put on my black bra and matching bikini panties and black thigh high stockings. I loved the feel of sliding them on my shaved legs. I was getting turned on just thinking about tonight. I put on my makeup which I now was getting pretty good at thanks to Raoul's sisters and the girl at the Mac store where I had purchased it.

Finally I picked out my outfit. I put on a white blouse, leaving a couple of buttons undone to give glimpses of my bra. Then i put on a red mini skirt I had bought when shopping with Marta and Alicia. I then slipped into a black pair of strappy four inch heels i had bought the same day as most everything else. I looked in the mirror and was amazed. A hot chick was looking back at me. I was proud of myself and anxious for Raoul to arrive. I lit a cigarette and waited for my man.

The doorbell rang a few minutes later. Raoul was at the door. He looked incredibly hot in black dress slacks and a white shirt.He said that I looked gorgeous then kissed me on the cheek and handed me some flowers which I put in a vase. I felt so girly taking flowers from a handsome man before going out with him.

He asked, "Are you ready to go?'

I said that I was and we headed out the door. As we got to his truck he opened the door for me like a perfect gentleman.

He asked ,"Do you like Chinese food?"

I replied, "sure."

As we drove to the restaurant I couldn't help but think, "wow, I'm on a real date."

Raoul kept looking over at me as we made small talk. He said. "i can't believe how beautiful you look." He then took his hand and put it on my leg.

We got to the restaurant and had a wonderful dinner although I ate lightly since I was still nervous and didn't want to upset my stomach. After we finished Raoul asked if I liked to dance.

I said that I did. I didn't tell him the first time I had danced with a guy was when I went out with his sisters although they may have told him.

We went to a small club. Raoul ordered me a daiquiri. I said I wasn't 21 yet but, he said not to worry. I took a few sips of my drink then Raoul asked me if I wanted to dance. I said "yes," of course and he led me out onto the dance floor.

We danced several fast dances and I was really enjoying it, The DJ then played a slow song and Raoul took me in his arms. I felt warm and safe in his arms but, having him so close was turning me on and apparently him too. I could feel his cock pressing into me. I groaned and reached down and gave it a squeeze.

He kissed me first just on the lips but, then his tongue invaded my mouth. I eagerly returned the kiss, getting more turned on. It felt so naughty to be kissing a man in public but, so hot.

We went back to out table and finished our drink. He asked if I wanted to go back to my place. I eagerly said "yes."

We got back in his truck and started making out. I had never been kissed like that. He was grabbing my ass and pulling me close to him as we kissed. He said that we better get going or he was going to take me right there in his truck. I replied that he should drive fast.

As we drove he couldn't keep his hands off me. I reached over and unzipped his pants and pulled his cock out. He groaned. I kissed the head and started licking the shaft. I then started going up and down on his cock. I couldn't get enough. I loved the salty taste. The idea someone might look in the truck and see us was a turn-on too. He groaned. "oh yeah, baby suck that cock."

The truck stopped. I looked up. We were in front of my apartment. He said," let's get upstairs."

I reluctantly stopped sucking his cock. We took the elevator up to my apartment, making out the whole time. We got inside my door and I immediately dropped to my knees, got his beautiful cock out and started sucking it.

Raoul groaned and said if I sucked his load out he'd last longer when he fucked my sissy pussy. I kept up the sucking, almost out of control. He started face fucking me; I was so turned on. Finally he held my head still and shot a big load down my throat. I hungrily swallowed every drop.

I stood up. I took Raoul"s hand and led him into the bedroom. I sat him on the edge of the bed and undressed him. I said, "Lay back," and he laid back on the bed. I went and got each of us a glass of wine. I then stepped into the restroom to freshen up my makeup.

I came back into the bedroom and took off my clothes. He said to leave the stockings on so I did. I climbed up beside him. We snuggled for a few minutes then began to kiss. He kissed my neck and worked his way down to my nipples. I found I love having my tits played with and was getting very turned on.

I then straddled him and kissed his chest and played with his nipples. I worked my way down to his cock which was starting to get erect again. i teased it with my tongue and stroked it with my hands. He was moaning and saying how good it felt.

He stopped me and said, "I want to fuck you baby."

I said, Yes please fuck your woman."

He had me get on all fours saying it would be easiest for my first time. I complied and told him there was lube in the cabinet in the headboard. He got some out and I felt him squeeze some onto my ass. He used his finger to get it inside me. It felt so good. Then he put a second finger in and I screamed with pleasure.

He took his fingers out and I felt his cock at my hole.

"Do you want this big cock in your ass pussy baby?'

"Oh God yes."

"Beg for it baby."

"Please give me your big cock. Make me into your woman."

i felt him slide the head of his cock inside me. It hurt for a second even with the dildo practice I had. He told me to relax and stopped for a second. I started to relax and told him to go ahead. He did, sliding his big cock inside me. It was like nothing I had ever felt. I screamed a little.

"Is it hurting you baby?"

"No, it feels so fucking good. Fuck me."

With that he started fucking me. I had never felt anything that good. I loved being fucked and having a cock inside me. With my encouragement he started fucking me harder. I was moaning and screaming. He was moaning and saying how good it felt.

I felt him tense up and soon he was filling my ass with cum. It felt unbelievably good, I then realized I had cum into the sheets without even knowing it. He pulled out of me and I felt a great emptiness. I squeezed my ass cheeks together to keep it from leaking out. i crawled up next to him and he kissed me and told me that it was wonderful. I thanked him for making me so happy.

"You want to do something dirty baby?"

"I thought we just did but, with you of course."

"Clean my cock off with your tongue."

"OK." So I slid down and started licking his cock. There was the smell and taste of sex but,it was still wonderful. It started to get hard again. I sucked harder. Raoul was groaning.

"Girl, you are amazing."

I looked up at him. What, an amazing cocksucker.?"

"Yeah, among other things. I want to blow this load on your face baby."

"Don't let me stop you."

With that he pulled out and gave me my first sissy facial. Like all other things related to cocks and cum I loved it. It made me feel so slutty.

I licked as much as I could reach off then got up to wipe my face. I returned to bed.

Raoul asked, "Do you mind if I spend the night?"

"No of course not but, I might need some more cock in the morning."

"I'll do the best I can baby."

With that I crawled up next to him and fell asleep in his strong arms.

I woke up before Raoul the next morning. I sneaked into the bathroom to remove yesterday's makeup and put some fresh makeup on. I then got back into bed with him and started stroking his cock. It was an incredible sense of feminine power to feel it harden in my hand.

Raoul groggily woke up and said, "What are you doing?"

"What do you think I'm doing? I'll stop if you want."

"Oh God no, please keep going."

With that I slithered down to his hardening cock and took it in my mouth. This elicited a groan from Raoul. I licked it up and down, paying attention to his balls. Then I took it in my mouth again. I couldn't believe how much I loved sucking cock. When he was nice and hard he told me to stop.

"Stop, I thought you were enjoying it?"

"I am but, I want to fuck that tight ass pussy again."

"Well, I'm not going to stop you."

"Get up here and lay on your back."

I complied although I was reluctant to stop sucking his cock. He grabbed some lube and rubbed some in my ass, first with one finger and then with two.

"Wrap your legs around me girl."

I did. Then I felt his cock slide in. There was a brief moment of discomfort then it slid in much easier than the night before. I moaned wrapping my legs around him. I pulled him close with my legs.

"You're really getting into this aren't you girl?"

"Oh God yes. It feels so good. I feel like such a girl. I love it."

"Well, I love fucking you babe."

Raoul, getting more and more excited fucked me hard, I was loving every minute of it. I couldn't get enough. It felt so good to be fucked. He reached over and started stroking my cock.

I asked, "What are you doing babe?"

"I'm making you feel good by playing with your clitty."

"You make me feel good anyway with your cock."

" I want to make you feel really good babe."

"Well don't stop fucking me or playing with my clitty then."

Raoul tensed up a minute later and I could feel his cum shooting into me. I screamed in pleasure. I came on my chest a minute later. He pushed off me after a couple minutes. As he lay beside me he scooped up my cum with his fingers and put them in my mouth. I greedily lick my own cum off them.

We lay there a few minutes and Raoul said that he had to get up soon because he was helping a friend move later. I groaned and said,"Don't go."

He said that he had too but, would be back to see me again.

I said O.K. but wouldn't he like to be cleaned off first.

"Oh God, you are insatiable."

"Its your fault, you turned me into a cum junkie.

With that I slid down and started licking his beautiful cock. I could feel it get hard again.

"One more load baby?"

"Girl you are going to wear me out but, O.K."

With that I took his cock in my mouth. I started deepthroating him to see if I could, I managed. Apparently I was born a natural cocksucker. Raoul started getting excited and was sliding his cock back and forth in my throat. He moaned and I could sense he was close to cumming. I started bobbing up and down on his cock faster and he tensed and shot another load deep in my throat. I, of course swallowed every drop.

After cuddling for a few minutes Raoul got up, got dressed, kissed me good-by and left. I got up after he left and went out to the living room and lit a cigarette. I thought about what had happened with Raoul and decided I didn't regret one moment of it. He had made me see what I naturally was, a sissy slut. I knew I was not going to end up living happily ever after with Raoul but, also knew there were a lot of cocks to please out there.

I was talking to Marta a few days later. We had become good friends since the shopping experience. She asked me what my name was going to be if I lived as a girl. I don't realy know why but, the name, "Tara," popped into my head. I told her "Tara." She said she liked it and Tara and her should get together soon. I agreed.