My First Time as a Sissy Ch. 02

This story is about my journey to being fucked as a sissy for the first time. Part One should be read first.

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When Raoul left after I had given him the first blowjob I had ever given I was feeling confused. I knew that I had enjoyed it but, didn't know how I felt about having to do it again as he had promised I would have to. I guess I wasn't going to have much choice. A couple days later he called me and said to dress nice, that he was coming over tomorrow night. I felt like a schoolgirl who had been asked out on her first date. My doubts disappeared and were immediately replaced with nervous butterflies.

I immediately went out to buy a new outfit for him. I headed to a local discount store and bought a floral sundress which looked like it would fit. I didn't dare try on female clothes at this time in my life. I also got a gold plated chain and a costume ring.

The next day I left school early to get ready for Raoul. I painted my toenails bright red and put on artificial nails and painted them bright red. I wore my sundress with purple bikini panties and a purple bra. My brown hair was already fairly long and I put it in a ponytail. I did my makeup with foundation, eye shadow, eye liner and red lipstick. My refrigerator was stocked with beer a friend of mine with a fake ID had bought for me. I put some soft music on the stereo instead of having porn on the TV this time.

Raoul showed up after work about six or so. I invited him in and offered him a beer.

He said, " sure," and told me that I looked pretty. I think I blushed. He noticed the music playing and said, "let's dance."

He took me in his arms. I felt incredibly feminine. He pulled me closer and I could feel his cock pressing into me. I looked up at him and he kissed me. I hesitated at first then I began kissing him back. We were really getting onto it and he said let's take this to the bedroom. I gladly took his hand and led the way,

He slid the shoulder straps off my dress and I let it fall to the floor and stepped out of it. I felt so feminine standing there in my bra and panties in front of this handsome man. I had him sit on the bed and pulled his shoes and socks off. He stood up and I unbuckled his belt and slid his jeans down. I gently squeezed his hardening cock then I unbuttoned his shirt and took it off him.

I was now getting really turned on and ran my hand through his chest hair and kissed his nipples. He moaned. and kept saying how hot I was.

He laid back on the bed. I crawled up between his legs and took his boxers off. His cock sprang up and I took it in my mouth with absolutely no hesitation whatsoever this time. I swirled my tongue around the head and up and down the shaft.

He was groaning now. I started bobbing up and down on his cock. I think this is when it really hit me that I just loved sucking cock. My own little cock (I didn't know what a sissy clitty was yet) was hard and I reached down and played with it while using my other and my tongue on him.

He started to lose control then. He put is hand behind my head and started face fucking me. I loved it. I couldn't get enough. I was moaning now and was so incredibly turned on.

He said that he couldn't hold back any longer and shot his load down my throat. I hungrily swallowed every drop. I then came myself a moment later.

He laid back in the bed and I crawled up next to him. It felt so right to be snuggling in a man's arms.

He asked me if I liked being a sissy girl.

I said that I did, more than I possibly thought I could.

He said, "Good, you are a natural sissy girl."

I think I blushed again, then said "Thank you."

He said, "I've got a surprise for you if you really want to be a sissy."

I said that I did. I asked," what is it?" but, of course he wouldn't tell me. He then said if I wanted to be a sissy girl I should get fucked like a girl.

I didn't exactly understand at first but he told me that sissies had ass pussies and they needed to get fucked.

I said that I wanted to but, wasn't sure if I was ready for that yet.

He said that he would give me time but, not too much and he wanted to be the first guy to fuck me.

I had no problem with that since no one else knew I was interested in guys, not even me until a week ago.

He said he had to go.

I looked sad and pouted a little and then slid down and started sucking his cock again.

He groaned and said he may have created a cocksucking monster. He was right but, I didn't know that then.

I got another delicious load out of him, and again swallowed every drop. He left and I fell into a contented sleep.

He texted me the next day and said to be home Saturday afternoon but, not to wear any makeup and to dress casually.

I replied, that I would of course, but was rather puzzled. Oh well I had nothing to do but wait, though my curiosity was killing me.

Saturday afternoon showed up and my doorbell rang. Two girls about my age or a little older were at the door.

One of them said, "hi, I'm Marta and this is my sister Alicia."

I said, "hi," with a puzzled look.

Marta said, "We're Raoul's sisters and we're here to help make you into a girl for him."

I was kind of shocked but, said "O.K."

She looked me up and down then said, "the staring material is not too bad but, it needs a little polishing."

Both girls giggled and Marta said, "come on, let's go."

I said "OK," and went out and got in their car with them.

They took me out first to the MAC store at the mall where a friend of theirs worked. She taught me how to do my makeup much better than I had before, and showed me several different looks. We left after purchasing a significant amount of makeup, with me wearing makeup in public for the first time.

Then we went to the Forever 21 store a little farther down in the mall. We clothes shopped and they made me try everything on which wasn't as embarrassing since I was doing it with other girls who tried on clothes too. I got a couple more dresses, skirts and blouses and some very short shorts that they both approved of. I wore a denim skirt and white blouse out of the store.

We then went to a shoe store. I am a men's size 8 so luckily women's shoes do come in my size. i bought some pumps, some cork sandals, and a caged heel. Then I got some pink Nike running shoes for good measure. I left the stores wearing the sandals with my new outfits.

We then went to Victoria's Secret naturally. They had a clerk measure me for my correct bra size and i bought several bras, pairs of panties, a corset, and several pairs of pantyhose and thigh highs. This was a great thrill shopping in a store i had dreamed of going into but never having the courage to do so before.

I noticed as we were walking through the mall we were getting some looks from the boys. I felt complimented and girly though I imagine they were probably looking mostly at my new friends.

We then went to a hair salon the girls used and my hair was styled in a more feminine look than my pony tail. I had some lighter highlights put in. I saw myself in the mirror and was amazed.

The girls said we had one more stop to make on the way home.

I asked, "where?" but, the girls wouldn't tell me.

We stopped at a store I had never been to before but, had seen as I drove by it. . It was labeled as an, "adult bookstore." We entered and I saw row after row of x-rated movies and then further inside rows of sex toys.

I asked the girls what we were shopping for and they said that a girl has to have toys.

We looked at dildos and they picked one out for me that they thought was suitably sized, then a smaller vibrator, "to keep in your purse," then an array of three butt plugs in small, medium and large. I embarrassingly paid for the items and we left.

They asked if I wanted to stop for a drink on the way home and I said "sure," but that I was underage and couldn't drink. They said that they knew a place with a bartender one of them had dated and we'd be o.k.

We stopped and they ordered a round of strawberry daiquiris. I was enjoying sipping mine when three college age guys came over to the table and asked us to dance. Alicia immediately said "sure."

Feeling a little light headed from the liquor I danced with a boy named Rob. The first two dances were fast and I had no problem but, the third song was a slow one and Rob was holding me pretty tight. I looked over at Marta and she was smiling at me. After the dance they said we should probably go since she didn't want to be responsible for me cheating on her brother. i started to protest and she laughed and said, "just kidding."

We went back to my apartment where they dropped me off. When Marta was getting my packages out of the trunk she found the one from the adult bookstore. She said, "make sure and use the dildo and butt plug before Raoul comes over next time and it won't hurt so much," then she winked at me and giggled. Marta and Alicia said that us girls should get together again some time and go out for drinks.

I said, "I had a really good time and would love to."

They said, "be sure and treat Raoul right."

I promised that I would.