Becoming Cassie Ch. 10

After each night of painting I stopped by different car dealerships and found two vehicles that would work at two different places. My favorite was the used Rav4 but still about $2,000 more than I wanted to pay.

On the last day of painting, my mom needed the car and dropped me off early. I was easily going to finish today even with all the visitor interruptions. I had already gotten so many contacts that I could line up more work probably through the summer. Everyone loved what they saw.

Being the last day Jennifer brought in a real nice lunch. She was so impressed with the job.

"Matt, what are you doing New Year's Eve?"

"Most likely just getting together with some friends from high school. Nothing special really. The Warrens have been away since before Christmas and they won't be back until January 3rd. They're in Aruba I think. Why?"

"You know the soft opening we are having New Year's Eve? Would you be interested in coming? We are doing make-overs for the New Year Eve revelers starting at 4:00 and I'm having a few of my friends helping me out. We have booked over 20 appointments already.

"Then we are opening our doors and having an Open House from 7 to 10PM . We sent out a mailer and hope to get some new business as well. We are doing raffles and giveaways. We are hoping people will stop in on their way to their own celebration, all dressed up and all."

"That sounds like a great idea and a great night," I replied.

"Do you think you're up for a Cassie night?"

"Hmmm, maybe. Can I let me know by the end of the day?"

"Oh, Jennifer, and one question. My mom's picking me up at 5:00. Can I give her a walk through and introduce you? I've been talking about this job for a while."

"Absolutely, and I won't say a word about Cassie or New Years. I promise."

By 4:00 I was done and began touching up little areas. It really looked good. The color schemes were perfect and I have to say, the painting looked great. Jennifer did a complete walk through with me and was equally excited and as I piled my equipment near the door.

Jennifer came over, handed me a check for $2,500 and gave me a big hug.

"Thank you. You really did a super job."

"And did you think about New Year's Eve? I forgot to mention earlier, but as part of the promo, Derek will be here as Britney. You know, come have your picture taken with our own Britney."

"As long as I can be just Cassie, I'd like to come. Are you really sure it would be alright?"

"I know it will be. It's my opening and I know it will be fun. I'll have Derek bring some extra clothes and things for you. You just have to bring yourself. Can you be here around 5:00 for a make-over?"

"Sure, see you then.

About 15 minutes later, right on schedule, mom appeared and I introduced her to Jennifer. "Your son is amazing. Let me show you some of our "before pictures" before you even look." Jennifer brought out her iPad and took mom room by room bragging on my work. She was so nice.

Jennifer said "Thank you for lending him to me during the holiday season. I hope you are proud of him."

My mom was impressed with my work and on the way home said how pretty Jennifer was and how she looked like Reese Witherspoon. And maybe someday I'd be lucky enough to find someone as nice as her.

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

On New Year's Eve day, I got a call at 10AM at home.

"Matt, this is Joe at the Toyota dealership."

"Hi Joe. What's up?"

"You know the Rav 4 you were looking at? We are putting it and about 10 other vehicles on sale today at noon so we can close out the year and get rid of some inventory. I know you were interested in it. Low mileage, great shape. I know it's going to be picked up right away so I was giving you a heads up."

"I'm listening. What's the price?"

"We are willing to take $2,000 off the asking price."

"Joe, that's still a bit out of my price range but it's closer."

"How much more do you need?"

"If you could go down $3,000 you have a deal."

"Let me confirm with my sales manager and I'll call you right back."

Within ten minutes he called back and said it was a deal. I borrowed mom's car, grabbed a $2,000 bank check and headed over to put the deposit down. We filled out the paperwork and shook hands.

"Matt, we will get the plates and registration for you, and we can settle up right after the first of the year. Congratulations!"

I was pumped, the vehicle I wanted at below the price I wanted to pay. A nice way to end up the year.

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

The rest of the day I was elated and I still had the New Year's Eve event at Jennifer's new place to go to.

I arrived promptly at 5:00 with nothing but me. The place was all decorated and looked fantastic. Jennifer was pure radiant. This was another new Jennifer I had never seen.

"Matt, this Rachel. We've done a lot of bridal showers and wedding parties together. She's going to do your make-up. You two are going to get along great."

Rachel was this cute, lightly tattooed gal with short red and black hair, and awesome make-up, but then, that was to be expected.

"Hi Matt, what did you have in mind for tonight?"

"Seriously, I'm not sure. I don't even know what I'm wearing."

"Oh, now this makes sense, Derek dropped these off earlier. One dress is black and one is silver. I kind of like the silver one for New Year's Eve." She held it up and it was angle cut just above the knee and gorgeous.

"He also left off about 5 different wigs here plus this other bag. Let's see which wigs pops with this dress."

We got down to two wigs and she said, "Let me check with Jen." In two minutes Jennifer came in and checked out the wigs. She picked up each one again and paused with the auburn wig with bold blond highlights. It also had one long side and one short side...real sexy. She kept looking at the dress, the wig and me.

She looked at me in the eye and asked, "Are you game girl?"

"I am...game on."

With that she scooted out and it was me and Rachel. Here, go change and put the robe on and we can get started.

Derek had everything and to my surprise I was going to be a D cup tonight. I got all dressed and when I came out Rachel had a book open with make-up for different hairstyles. It only took about 5 minutes to decide on real flashy runway model make-up look.

When Jennifer came by, she looked and said..."Perfect"

Rachel loved her worked and asked me a hundred questions about school, sports, crossdressing, boys, parties, everything. She was like being with a counselor. I was slowly developing better answers and even shared a little bit about Eric. She was so much fun to talk with I'd love to meet her in another setting.

She helped me into the dress as if it was no big deal that a guy was wearing a dress. She brushed out the wig, adjusted it to my head, dug out some clip on rhinestone earrings and a necklace and said, "You are freaking hot girl."

I stood up and faced the full length mirror and could not believe it was me. I looked like the picture in the book and with the padding Derek left me, I had to agree. Hot was a great adjective.

From 6:00 until 7:00 I helped Jennifer and her crew set up little things, arrange tables, put up some more decorations. I kept meeting people and introducing myself as Cassie, one of Jennifer's clients. I got a number of second looks but always offered nice comments to deflect them.

Around 7:00, Britney arrived in all her glory. There was no Derek in her that I could see. She was sooo good and practically sucked all the air out of the room.

Allison, the photographer, was busy taking complimentary photos of everyone who came in and had me pose for several, some with and some without Britney.

After a while, I went over to Jenifer and quietly asked, "I really want to let your associates know I'm Matt. I think I'd feel bad later on if I didn't. Are you OK with that?"

She whispered back, "I was hoping you'd say that. It's a great idea."

As Allison took another picture of me with Jennifer, she asked, "Would you like me to email you a copy?" This was part of the marketing plan to get everyone's email address.

"Sure," I replied in my Matt voice, "It's Matt@aol.com"

She stopped and looked up and said, "No way." She kind of shook her head in disbelief, gave me a big smile and hug, and then had me pose for about 10 more pictures in all kinds of great poses that she set up.

As more and more people arrived, I helped greet, direct and introduce them. I was having so much fun.

Derek also pulled me aside throughout the evening and gave me all kinds of tips.

"See that mirror? Mirrors are your friends. Use them. Always check your posture, your hair, and your make-up."

"See that model looking gal over there. Watch how she holds her champagne glass. See how she stands. Watch how she walks. Observe how she greets people with a touch of her hand and smile. She is very good."

Ten minutes later he came up to me and said, "Cassie, don't move a muscle and look at yourself in the mirror to your left. "

I glanced over with just my eyes and I kind of looked like a guy at the moment. I was bummed. I thought I was doing OK in my heels and dress.

"Now, make yourself look like her over there."

Glancing back and forth between her and the mirror I slowly adjusted myself. "Better," he said, "Much better. Keep working on it tonight while you are here."

He was worse than Aunt Mary, but realistically, he knew his stuff.

As the night went on, he told me all kind of stories about his entertainment business and how he studies a half dozen popular icons and learns their most popular moves. He practices at home with large mirrors and video playing on large screens. And then he videotapes himself. "I'm my own biggest critic."

He went on and told me, "After years of dance, ballet and gymnastics as a kid, this is a natural. I can blame this all on my parents."

He was so much fun to talk to. Now I was so glad I did not get a blowjob from him at the Warrens on Halloween.

Later he asked, "What are you doing after 10PM?"

"To be honest, I have no idea."

"I have a corporate party to do at 10:30, want to join me?"

"What would I have to do?"

"Mingle, be friendly like you are now, and tell the guests how wonderful they look and then tell them how amazing I am dancing."

"I could do that."

"And if you want to play a bit, they tip nicely."

"I'm naïve. Play?"

"Well at this place, some of the executives love extra private attention. I give one of the guys, not sure if he is the CEO or CFO, a blow job in his office after my show. Seriously, a blowjob by Britney Spears is a big deal in this guy's life, or any guy for that matter."

"And come to think of it, there's a gal there named...Leigh. She's hot, a little older, kind of a lesbian or dyke or something like that, but loves me to pieces. She always likes to role play and then gives me a blowjob. It's such an easy gig with her."

"That's a nice option. Let me think about it."

"It's just an hour show and after that I'd be happy to drop you back here to change and you would be home at 1:00 if that would work out."

A little later I told him that sounded like a great plan and I'll give the party my best shot. I kept practicing all the little tips he gave me and I could tell I must be doing something right because I got more stares from the men.

"Looking hot there Cassie," Derek whispered as he walked by me more than once.

"If I didn't know better, I'd want to do you myself girl," he whispered another time.

Another time as he walked behind me, he dragged his hand across my ass which was sticking out a bit like he suggested, and he whispered with a grin, "I'd love to pound this little ass."

As I walked across the room to greet another client, I heard his voice in my head saying, "Place one foot directly in front of the other, and own the room as you walk." This was so much fun.

I also had a chance to prank the travel agent by pretending to book a trip and then giving him my real name.

And then the fashion consultant by asking her questions about my wardrobe, and then asking about my painting clothes.

And the wedding planner by having Britney plan our Vegas wedding, and then her forgetting my name like in the song by Carrie Underwood. "Matt, my name's Matt. Why can't you remember that?"

All three of them had no idea until that moment. They all then had Allison take pictures of me with them.

The Open House was a huge success for Jennifer. There were lots of giveaways and she and her associates made lots of contacts. And at 10PM, Britney and I updated our make-up, gave Jennifer a huge hug and headed out.

The party was in a corporate function room of an investment banking firm on the top floor of a building I had never been in. When we walked in there was security and all Derek said to them was "Britney and Cassie" and they checked us off the list. No IDs needed.

We took the glass inside elevator up and got the greatest of looks from people in the building. This was really exciting.

We had another checkpoint at the party entrance and then Britney strutted into the room as little Cassie slinked in beside her. "Own the room Cassie," Derek whispered. Seriously, every one stopped and looked.

Britney was welcomed with a big hug by one of the men dressed in a real nice suit so I followed her and did the same. There were lots of pictures being taken of us and I did my best to arch my back with my shoulders back and mimic as many of the hot babes at this party as I could. This was work. There were over 150 people there.

Promptly at 11PM, Britney was introduced and did two dance numbers. Derek was freaking amazing. He had all her great moves down just like the music videos. I worked the room and tried to make the guests feel special, always complimenting the women and always eyeing the men.

Then there was this amazingly hot woman, maybe mid 30's with short cropped spikey hair, who kept checking me out.

Right after Britney stopped dancing, she came over and introduced herself. "Cassie, I'm Leigh. Derek has told me you might come. I have to say, you are lovelier than he described you."

I nicely shook her hand and replied quietly, "Leigh, I am so glad to meet you. I loved the way you looked at me the moment I got here. I was hoping Leigh was you."

Derek nodded to me and the two of us exited into the hallway. We headed down to her office and we chatted on the way. She was so nice. She was the Executive Vice President and had this wonderful office with desks, sofas, chairs, a conference room, massive floor to ceiling windows overlooking the city and her own bar. This was like on TV.

"I know we only have 30 minutes, so let me help you out of your dress. There is an outfit in the bathroom for you. And would you unzip me as well please?" I could sense her tone changing a bit.

I unzipped Leigh's dress from the back, and as she stepped out of it, I could not help but stare.

Earlier, I could not tell when she was in her halter dress, but she could not have been any more than a B cup, maybe even just an A. She was really muscular and was now wearing just her black panties.

She spoke in a deeper voice and asked, "Do you like what you see my Cassie?"

Looking at her up and down, I quietly and seductively said, "Oh yes. And I want you so bad. Let me go change into something more comfortable."

I headed into her executive bathroom and there hanging on the door was a beautiful, Simone Perele black short nightgown and robe. I was changed in 5 minutes and fixed my make-up.

When I came into the room, she was wearing a pair of jeans and wife beater shirt with no bra. And if I was not mistaken, there was a noticeable bulge in her pants where a cock would be. That was a dramatic change.

As she walked over, she stroked my breasts through the nightie, felt my nipples and asked, "Well my Cassie, are you getting excited wearing the new gift I worked so hard buying for you?"

"Does it show?" I asked as I pressed my nipples up to her hands even more which were getting hard as she lightly rubbed them.

"I love it when I get you excited," she replied.

"I'm always excited when I'm with you," I whispered in a submissive type of way.

She then began lightly squeezing my nipples through the nightie. Her hands were wonderful and I closed my eyes and sighed as she squeezed them tighter and tighter.

Instinctively I reached for hers and she lightly moaned as I returned the favor through her Tshirt, and then ran my hands down to her groin and rubbed her bulge.

She began driving her pelvis against my hand and I pushed harder and harder against her. "Cassie, you know you want it girl."

Leigh was lightly stroking my arms and face with one hand while squeezing my nipples with her other. "Please don't stop," I whispered.

"You are so feminine my little Cassie. I love your breasts."

Then she suddenly stopped and said,

"Wait. What's that between your legs, young lady?"

I backed away quickly, trying to look embarrassed.

"Nothing Leigh. I don't know what you're talking about."

"Cassie, have you been hiding something from me?"

She dropped to her knees and said, "So Cassie has a cock, does she? Let me see."

OK, that woke my fella up and as she slid my panties down to my ankles, she began kissing and nibbling on my cock.

"Oh Leigh, I was so afraid you'd find out and not like me anymore."

"Cassie, I knew there was something special about you. You have a cock just like me."

"And it's a beautiful one at that," she said as she planted another kiss on it.

Leigh then took my entire cock right down her throat. She began playing with it with her tongue and cradled my balls with her hands.

I was playing along as we went back and forth with our dialog, and she got more aggressive with her hands. By now my own hands were caressing her short hair and face.

This continued and she reached behind me and began probing my hole with her moistened finger from her mouth. She went into me deeper and deeper, but ever so softly.

This was feeling real good and she knew she was getting me more excited. This was no longer role playing on my part.

She kept backing away with her mouth, allowing me to calm down and then taking me fully down her throat again and again.

"Oh Leigh, I can't hold out any more. This feels too good!!"

Then she said, "Then cum for me Cassie. Cum and fill my entire mouth like you have never done before."

Holding her head with her short hair was like holding a guy. I was now fantasizing that I was with Eric, and as I began to vigorously cum I said, "Leigh I want you in me so bad."

With each pulse of my cock in her mouth, she penetrated me deeper and deeper with her finger. My whole body was shaking. Instinctively, I leaned forward a little to let her finger in deeper. I was still cumming and did not want to stop.

As I slowed down, she placed two fingers in me and was massaging me deeply inside. My legs were quivering and I needed to lean over even more. I was now resting on my arms on the corner of her desk just to balance.

Leigh then moved behind me, continually probing and massaging me inside with her fingers. This brought back wonderful emotions and I was almost crying with pleasure as she went deeper and deeper.

"Do you like me in you Cassie?"

I could barely get out a "Yes."

When she finally removed her fingers I slowly worked at getting myself upright. My head was spinning, but she was not done.

Leigh moved to in front of me on her knees and continued sucking my completely soft cock, almost making love to it. She kissed it repeatedly and licked it all over. "I so love your cock Cassie," she whispered.

I stood there in a daze as she continued. This was so unreal.