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  • Becoming Cassie Ch. 03

Becoming Cassie Ch. 03

12

For the next two weeks all I could think about was being Cassie again. All my life I've always had dreams of being dressed but the people in those fantasies were never real. My fantasies were now becoming realities.

And I had to wonder what were the Warrens thinking this week. I had really been expecting the absolute worst scenario if I got caught in real life. I never really thought that they would find it to be stimulating that their guy babysitter would turn into their girl babysitter each night when they were out.

But it was going to happen...again. I was really going to the same apartment where I could become Cassie again in less than 14 days, then 13, then 12 days. While it was something I had always hoped for, now that it was coming closer, it was almost scary.

When that Friday finally came, I was excited and nervous all at the same time. My mom dropped me off as usual and as I knocked on the door I was almost shaking. This was a different feeling. I was hoping it was going to be Mrs. Warren, but Mr. Warren appeared in a tuxedo.

I was shocked to see how dressed up the Warrens were getting for this event. I knew it was formal but I did not really expect it to be this formal.

The last time I saw him he was sound asleep after I had him a hand job as Cassie while wearing his wife's dress and lingerie. Now I'm standing in front of him dressed as Matt. This was a bit awkward.

It was a very pleasant greeting and I told him that he had this James Bond look going with his black tuxedo. I think he appreciated that.

And Mrs. Warren could easily have passed as a Bond girl. She had her hair up with long sparkling earrings, and even though she was still running around in her long robe, she looked absolutely stunning. True to form, she had not yet changed into her gown but she was still radiant.

I was barely there for a minute when I heard her call,

"Matt, would you help me for a moment?"

I looked to Mr. Warren who gave his approval with a nod. I was so glad I was still on good terms with him. He apparently was cool with all this.

I had to believe his wife never told him about what had happen after he fell asleep. Seriously, wearing her clothes is one thing, but being intimate with her in their bedroom, even as Cassie, is completely another. I had yet to figure this couple out.

I opened the door to the bedroom and Mrs. Warren asked, "Matt, would you be able to help me into my gown?"

"Certainly," I replied.

Facing me, she untied her robe and let it dramatically fall off her shoulders onto the floor...almost like in slow motion. There she was, standing there in the sheerest of black lace panties and an extremely low cut black bra. Her nails her perfectly done in deep red and all I could do is stare.

"Jealous??" she asked coyly.

I knew immediately what she meant. The Cassie in me wanted to be her so bad.

"Absolutely...you are so beautiful. But I don't mind being jealous one bit. Here, let me help you with your gown."

With delicate ease, we slid on her gown and I adjusted the straps from the back. There was actually very little to help her with and I think she knew that. She just wanted the attention. I stood back and admired. She looked spectacular.

"Now I am really jealous!" We both giggled.

"I want to wear this dress so bad", I told her.

"You'll just have to wait", she replied with a wry grin.

After she adjusted her hair and make-up one last time, she said "Oh, before we leave, we have a surprise for you." Emphasizing the word "we".

"First, Mr. Warren has not stopped talking about you since two weeks ago. It's been Cassie this and Cassie that. Now I'm beginning to get a little jealous of you! But I actually think it's cute."

"But second, we knew this event was coming up and talked about it for a while. We felt that if we came home all dressed up like this, then maybe you should have something special to dress up in as well. You know, to welcome us home in and all."

With that she took me by the hand and brought me over to the corner of the room. There on the chair were two boxes with bows on them. She handed me the smaller one first and said, "These are for you. I hope you don't mind."

Inside the first box was a bra and pair of panties. "We went out together and bought you the same matching bra and panties as mine."

They were beautiful. "Really? These are so nice." I held them up to me and embraced them.

"Yes, and there is more." Mrs. Warren handed me the other box and inside was a black gown and under the gown were heels.

"And heels, you bought me heels?"

"A girl has to have her heels. Now you have your own!"

I gave her a big hug but was careful not to smudge her hair or make-up. "Mrs. Warren, you are being way too nice to me. I still feel so bad about sneaking around in your clothes, and then you and Mr. Warren go out and buy me these?"

She replied, "I told you we were going to be the bestest of friends. And to be honest, I have not had this much fun thinking about you and planning to be with you in a long time."

"Oh, and one more thing. Make-up."

"Mr. Warren felt that if you were going to be wearing such elegant clothes when we arrived home you should also have some make-up on. And since tonight is such a special night for us, we've arranged to have it done for you."

"At about 9:00, my good friend Jennifer is coming over to do your make-up. I told her all about you and she cannot wait to meet you. She's an expert and actually does make-up for a living."

"Just be dressed in one of my regular dresses before she gets here to do your make-up, and then shortly after 10:00 change into your gown. We hope to be back no later than 10:45 or 11:00."

It was now time for the Warrens to leave. I took a few pictures of them together and then with Benjamin. It was a fun time watching them pose for pictures but my mind was elsewhere. Where was all this heading?

From the time they left, the minutes dragged. I kept looking at the clock every two minutes and realized that if I could keep myself busy with Benjamin, then maybe the time would go faster. And it worked, we played some games, read a story and then the clock struck 8:00.

I felt relieved that he was such as good sleeper, just like his dad, and by 8:15, he was fast asleep. I decided to make a quick change before Jennifer arrived so I headed into Mrs. Warren's room.

Seeing Mrs. Warren all decked out before they left, teasing me to no end about me wishing be her and then giving me clothes to wear was just too much. I had this burning desire to change into Cassie right now.

I stripped off my clothes and quickly changed into one of her nighties from her drawer. I located the matching pair of panties and grabbed the wig.

My comfort level in their apartment was real high. No more sneaking around. No more worrying about putting it back in the right drawer. It was if she had opened up her room to anything I wanted to wear.

Even without the make-up, I could see the Cassie from two weeks ago in the mirror. I could barely contain myself as I made it into the bathroom and unleased a massive load I felt I had been carrying for days.

It was so intense that I shook! I'm an athlete and I was breathing hard.

This is Cassie stuff is tough. But now I could at least calm down before Jennifer came.

I grabbed some hand towels and washed myself real good. Jennifer was coming over shortly. I wanted to look and feel good.

Now that I felt more relaxed, I put on the new bra and panties the Warrens bought me. I looked at myself in the full length mirror. Much better, but I almost got immediately excited all over again.

Stop it, I told myself. I just had to keep telling myself to slow down.

I then tried on the new gown and heels and was so glad they fit. They were simply elegant together. I put the gown on a hanger and changed into one of Mrs. Warren's nice dresses as she had requested. I then added a little lipstick in my own clumsy way because my look was so wrong without any.

I looked over at the clock and I still had five minutes. I plunked myself down on the sofa and said to myself, breathe, just breath.

Promptly at 9:00 there was light knock at the door.

"Jennifer?"

"Cassie?"

I opened the door and there was one of the cutest little blondes I have ever seen. She had kind of that Reese Witherspoon look to her.

"Cassie...you are adorable, just like Lisa said." She gave me a professional but sweet hug.

"Thank you, that is so nice of you to say" I replied.

"Cassie, just so you know, I've known Lisa for a couple of years now and just love her to pieces. I am so glad you have had a chance to meet her, too."

"Now, she said you have a special outfit to wear tonight and she wanted me to do some make-up, so let's have a look see at the gown."

We walked into the bedroom and she looked at the gown and then at me, and then at me and then at the gown and asked, "What color wig do you fancy?"

"I only have this one I'm wearing, why do you ask?"

"Lisa asked me to bring a couple over for you to try. I'm thinking that with this black gown and your light complexion, maybe this dirty blonde wig would work best. It's just past shoulder length and with these wispy bangs, I think it would be perfect. But let's wait to decide. I brought a few. "

"OK, first let me help you off with this dress and you can put on this robe."

Jennifer walked behind me and unzipped my dress and slid it off. "Leave your heels on for now until we get the right look."

"Cassie, that is such a cute bra...and I love those panties on you. They fit you so nicely."

"Thank you," I replied. "They are actually a gift to me from the Warren's tonight. I could not believe they would do something like that."

"I think someone really likes you girl."

She then walked in front of me and started studying my face. She stood back a bit, and checked me out from each side.

"Nice, very nice. I'm really excited about doing this. And I know I said it before, but I so like your bra."

"May I?" she asked as she reached out with the back of her hand and lightly touched the fabric of the bra. She could feel that my nipples were rock hard.

"Oh my, little Cassie likes it as well. May I borrow it after tonight?" She laughed but I think she was serious.

I could see she was going to make this fun. I almost hated putting on the robe, but complied as she began applying the make-up.

She was a real artist. She first put on a foundation and then began with the eyes. "Cassie, your eyes are a window to your soul. They are a girl's best weapon. And you have gorgeous eyes and long eyelashes. Use them."

She continued with eye shadow, eyeliner, mascara, blush, lipstick, always explaining what she was doing at each step. She then placed the wig on. As she sat back I thought she was done. I could not wait to see what it looked like. But, she removed the wig and continued to make adjustments for about another 10 minutes.

"May I see now?"

"Do you want to see yourself with the wig or without?"

"Let's see it without so I know what it should look like if I ever do it myself someday."

"OK", she said. She turned the mirror towards me and I stared in disbelief. I barely recognized myself. There was lots of make-up and very little me. I was nervous, very nervous. What would the Warren' think? They spent so much money on the new dress and now I don't even look like me.

Jennifer read my face and kept saying I looked great, but I had my doubts.

"Just wait", she said.

I stepped into the gown with her help, steadied myself in the heels and she began the process of brushing out and adjusting the wig.

"No peeking until I am done...promise?"

"Promise."

The wait was unbearable. She adjusted it more and kept brushing it a little left and right.

"One more minute...now hold still as I clip on your earrings...now just a little more lipstick and I think we are there."

She finally said, "Cassie, now you can turn around and look."

I slowly turned around and gasped. I was beautiful...seriously...model material. What a difference professional make-up makes. I had been so wrong about the look. I kept looking and staring at the make-up and wig from every angle. I thanked Jennifer at least hundred times.

And then Jennifer said,

"You need to calm down there young lady. It's one thing to have sexy nipples popping through your gown, but not your penis."

I looked down. This gown showed everything.

I then looked at the time and it was only 9:45. I said the obvious to her, "I will never be able to keep this down for 45 minutes until they come home. This is not looking this good."

Jennifer said, "I agree. Let's get that dress off and fix that." She moved behind me, helped with the zipper and steadied me in the heels as I stepped out of the gown. That only made things worse. Now I was a smoking hot babe standing in sexy lingerie in front of the mirror with a raging hard on.

I thought it was off to the bathroom for another round, but Jennifer said, "Alright, remove your new bra and panties. We don't want them ruined either."

She walked over to Lisa's drawers and pulled out a black babydoll nightie and pair of skimpy satin panties. "Here, put these on."

She helped me change the clothes and I swear my cock grew even more. She just laughed and said, "Damn, you are way too excited young lady." I didn't have the heart to tell her I had masturbated just before she arrived.

With one quick move she removed her top and then her bra exposing two of the perkiest breasts I have ever seen. I couldn't help but stare for a moment in disbelief.

"Do you like these Cassie?"

I said something smart like, "Oh my."

"Let's move this floor mirror over closer to the bed so you can watch what we are going to do next. Don't want any of my awesome make-up work to go to waste in any old bathroom sink."

"Cassie, I'm going to lay down on the bed and you're going to straddle me...you know, cowgirl style."

"Not sure what cowgirl style means, but I get the straddle idea." I said.

She then looked at me and asked, "You don't mind being on top, do you?"

I just laughed and said something stupid like "I don't think so."

Jennifer, still in her jeans with her legs closed tight together laid on her back and had me sit on her crotch with my legs spread. "Do you like this Cassie?", she asked.

Let's see...wearing a baby doll nightie and with satin panties while straddling this amazing chick...It was easy to say, "I love it!" And the mirror was positioned so perfectly I could see my entire body riding her. I now understood cowgirl style.

Jennifer then began fondling my breasts through the nightie and slowly began rubbing her groin up into my outspread legs. "Do you like this Cassie?"

I caught my breath and replied, "This is unbelievable!"

"Do you like what you see in the mirror?"

All I could see what this hot, dirty blonde in a black nightie grinding away on another hot blonde. I had trouble believing it was me. I started moaning a yes in response.

She then began squeezing my nipples, harder and harder. "Is this better Cassie...is it?"

"I can't hold it!", I cried. The visuals and physical touch were just too much.

"Cassie, yes you can. Close your eyes and think about anything else."

Jennifer slowed down her pace but kept lifting her crotch and grinding into mine in a slow rhythmic pattern.

"That's better", I said. Looking down I could see that Jennifer had her eyes closed and was beginning to softly moan with each lunge. Her breathing got deeper and longer. I could not believe for such a small girl she was lifting me with each thrust.

With each moan and thrust I could feel myself getting closer and closer to exploding again.

"Stay with me Cassie!! Don't you dare even think of having an orgasm before me." She was now groaning with each thrust.

With her legs, Jennifer slid me up even further on her and tore the skimpy panties right off me. My cock was now between her breasts and she was squeezing her little breasts together on my cock. It was getting hotter and wetter.

I kept rocking it back and forth between her breasts. I was now squeezing my own nipples until it almost hurt. I loved seeing what I was seeing in the mirror.

Then Jennifer pulled my body down on top of hers, reached behind me and slid her wet fingers right into my butt hole. At first it hurt but then I wanted more. I leaned forward even more to let her in even deeper.

I was now feeling things I had never experienced before..."Now Cassie, now!"

With one final push by both of us, I came all over her breasts, and I mean all over. Jennifer still had her fingers in me and slowly massaged me as she removed them as we slowed down our pace.

"Cassie, you're freaking awesome! Those were the best orgasms I have ever had."

My head was spinning but I was able to get out another brilliant statement..."But, I hardly even touched you. I don't get it."

"Honey, it's not just about you. You simply being here made it happen"

After about 10 minutes of relaxing and chit chatting, I had calmed down and we started cleaning up. We were both a mess, but the make-up was untouched. We could now laugh about it.

"Do you feel relaxed now Cassie?", she asked sarcastically.

"More than I could ever imagine."

"Good. Let's get you dressed beautiful, and ready for the Warrens."

For the next 15 minutes, Jennifer was all business. I changed back into my new bra and panties. Thank goodness Jennifer suggested I changed.

We put on the gown, adjusted the heels, touched up the make-up and put the wig on for its final time. We tried the other style wigs, but decided that for tonight, it was the blonde. Jennifer did say she like the short funky auburn one, but maybe some other time.

As she packed her final brush into her bag she said, "Cassie, you are beautiful. Have a wonderful time with Lisa and Alan tonight. And I really hope to be able to hook up with you again. You are a delight!"

With that we gave each other a little air kiss and off she went.

+++++++++++++++++++++++++++++++++++

I now had to radically change my thoughts over to the Warrens. They would most likely be here within 30 minutes and I needed to refocus.

Think, think. What would Mr. Warren be like tonight? What are his thoughts after an evening like this? Especially after being all dressed up in a tuxedo and all.

And Lisa, did she have fun all dressed up? Did she get the attention she so loves? And would she share with me some more secrets when she got home?

I tried to prepare mentally the best I could so I could not only make them happy but also exceed their expectations.

I had to keep remembering that they were coming home with amazing anticipation of seeing me in the new dress and all made-up. I was doing my best to recharge after just having one of the best times of my life with Jennifer.

I sat down and opened a Vogue magazine. I began visualizing I was one of the models. That lifted my spirits a lot and by the time I heard the key turn in the door, I was up and ready.

"Cassie? Is that really you?" I guess they liked the look.

I slinked over to them in my best sexy walk and planted a kiss on Mr. Warren, tongue and all. "You look so handsome in this tux...As I hugged him, I turned and looked over at her and asked, "And Mrs. Warren, how did you ever keep all the ladies away from him?"

"Easy, I clung onto him all night long" she laughingly replied.

"And all the men must have been wishing they were you Mr. Warren...having such a beautiful wife."

With that I walked over to Lisa and gave her a little air kiss but I really wanted to give her more. I was hoping that would come later.

"Well, our little Cassie has certainly grown up in since her last visit. You look beautiful. What did you think of Jennifer?"

12
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