Becoming Cassie Ch. 07

When I returned to the kitchen, I was all dressed in a cute nightie and robe, I could smell the coffee that she already poured. As she walked behind me she gave me another little hug, sat down with me and said, "I like this...I could really get used to this."

"Mr. Warren is going to be here around 4:00. We have plenty of time to go through everything, figure out what we are going to show him and how, and hopefully get some time to play throughout the afternoon. Does that sound good?"

"I could not have planned it better," I replied.

"Cassie, I have to be honest. For the last two nights he has fallen right to sleep and I've been using my vibrator...a lot, especially thinking about today. So if I'm a bit over the top, it's really not my fault."

"I can deal with over the top. I just completed a huge intensive time at school. I'm ready for it."

Our first stop was the closet. Virtually everything came out and we made certain areas in the room for dresses, for skirts, for blouses, for jackets and for pants. The only things that were organized in her closet were the nighties that I did from last week.

"See," she exclaimed proudly, "I kept my nighties neat all week!" I just shook my head.

We were to begin with the dresses so she turned and asked me which bra and panties set I wanted.

"I'll take the ivory bra with the flowers and matching panties," I said. She located them and tossed them to me.

Then facing me, she dropped her robe and standing there completely naked in front of her dresser drawers she announced she was going to wear her black bra and panties.

As I was putting mine on and adjusting them in front of the full length mirror, she walked behind me, still naked and gave me another hug. I then heard her say..."Crap."

"Is something wrong?"

"No, everything is perfect. That's the problem."

She reached over and grabbed her vibrator on her night stand. "You need to excuse me for a minute. This is the third time this morning."

"My mornings are the worse...or best depending on how you look at it. I wake up and my nipples are rock hard and all I want to do is have sex. Cassie, does that ever happen to you?"

"It does on occasion. And sometimes it's almost embarrassing because my nipples stay hard for a while and show through my shirt."

"Well, it happens to me all the time. Come sit beside me for a bit," she said.

I curled up beside her on the bed and she was still naked. She offered her breast to me as she began to use the vibrator on her clit. I gently played with her nipple with my tongue and she said,

"You're getting so good at this Cassie. That is so nice and gentle, just what I need this morning."

I could feel her breathing change, sense her body moving in a simple rhythm and her hips rising up and down. I knew her moans and picked up my pace slightly, playing with her nipple with my tongue and lightly massaging her other one with my fingertips.

She had to have had 3-4 deep orgasms in a row. After her last one she cuddled up to me for a couple of minutes and whispered,

"There, that's much better. They are so peaceful and wonderful. And it won't be the last for either of us."

After a big stretch and playful kiss, she said, "Now, on to the dresses."

By noon time we had tried on all the dresses and made several piles. One pile was to be given away. We both agreed they neither fit her or me, or they were so outdated that they would never come back into style.

We had Lisa's group that only that were perfect for her and were simply too tight for me. We also had a Lisa and Cassie pile that we could both wear, and a Cassie only pile alone.

I loved my collection and we named it the Cassie Collection. It was a younger looking pile and made me feel more like a college girl that a 30 year old woman. We organized these in the closet, along with my long dress I wore for the formal night.

In another group I found some fun outfits. Plaid kilt skirts, a nurses outfit, and several cheerleader outfits.

"You were a cheerleader? That's awesome."

"Try it on Cassie, I bet it will fit, there's a lot of give in it. And here, put on these white ankle sox. Let's go for the complete the look."

While standing in her cheerleader outfit, she fixed my make-up a bit more to make me look more young and innocent...a lot of pink lipstick and blush. I loved it.

Standing in front of the full length mirror, the cute make-up was absolutely perfect. I stood flicking my hair over my shoulder with my hand or with a shake of my head, standing with my hands on my hips, and posing in every cheerleader pose I could remember. I even tried a few gymnastic moves and loved the look.

"I have to tell you, Lisa, as a guy, I never wanted to do a cheerleader, but I always wanted to be one. It must have been such fun."

"It was. I can't remember the number of cocks I sucked in that outfit...and proudly, I never spilled a drop on it."

"Mrs. Warren!"

"No seriously. Even seeing you in it now brings back those memories. How does it make you feel Cassie?"

"Horny, for sure. Like, if I was a girl, I would love to get laid right now. I can tell my nipples are hard just thinking about it. I guess it's the ultimate fantasy."

She went to the corner and picked up a box.

"What is in the box?"

"These are my big girl toys. Do you want to see?"

There had to be 4 strap-ons, a half dozen vibrators, several dildos and two belts with this little butterfly looking thing on it.

She stood behind me and began to caress me and whisper in my ear, "Cassie, you are the sexiest cheerleader on the whole squad."

As she kept this up, she began grinding against me and running a large dildo up and down the cheerleader outfit. I got more and more excited.

"My beautiful cheerleader, I want to do you soooo bad."

She then walked over to her nightstand, pick up the lotion and returned with a smaller dildo in her hand.

"Cassie, remove you panties and relax for a bit by yourself. Use the lotion and this for a few minutes. I will be right back."

I knew what the lotion was for and I was secretly hoping we would use it at some point today. I bent over and slowly began using it and the dildo to loosen myself up. Just the smell of it alone brought back great memories.

Seeing myself as a cheerleader in the large mirror beginning to penetrate myself with the cock like dildo was a dream come true. The more I used it, the more I adjusted my body, and the easier it became to probe deeper and deeper.

The feeling was overwhelming and I actually forgot Lisa had left me as I got the entire dildo in me. This was so overwhelming.

When Lisa returned she had on a pair of her jeans, a tshirt and her hair tied up in the back, not her usual hair down to the shoulders look.

She walked around me as I continually slid the dildo in and out and said, "That's right girl, you want it. Take it all in." She draped her hands all over me as she continued to walk around me in a cat-like pattern.

She then led me over to the bed and instinctively, I took the same kneeling position as I did the last time on the bed.

Lisa dropped her jeans and put on the smaller strap-on she had used on me once before. Slowly she slid it in me as if it belonged. She whispered, "See, that was so much easier than before. You can take me easily now. You've learned how to relax girl."

It felt so good and I was enjoying not just the feeling of her being in me but her words as well.

She stayed with me for 10 minutes, slowly moving in and out of me, and was whispering, "You are the hottest cheerleader ever and I wanted you ever since the first day I saw you." This was wonderful and I could feel the long slow thrusts inside as never before.

"Hold on Cassie, another member of the team wants to meet you."

She slowly removed the cock from me and I could tell he was changing the strap-on.

"Cassie, you are freaking beautiful and I want to pound that cute little ass of yours," she said.

I could feel a lot more pressure on against me and thought I was going to split open but she kept saying in a strong voice, "Relax Cassie and let me in...let me in."

Then suddenly, my muscles relaxed more and I felt her penetrate me. It was nothing like I had ever felt and was a combination of pain and pleasure.

Lisa held right there and kept whispering erotic words to me. Slowly, the pain went away and I could enjoy having her in me.

As I looked to the mirror the vision her in jeans dropped around her ankles in a tshirt, with her hair up made it feel like it was a guy and not her.

Lisa began sliding the cock in and out at a real slow pace and then picked it up just a bit.

"Enjoy it Cassie...you want it Cassie. Take me in you deeper."

She then reached under the cheerleader outfit and began caressing my cock as it grew harder and hotter.

Her pace was picking up more and I could feel her penetrating me deeper and deeper with each slow lunge.

"How does this feel head cheerleader Cassie?"

I did my best to squeak out, "Wonderful...I want you so bad."

"What was that Cassie?"

"Fill me up...now...I want you." I began thrusting back on her as I watched her behind me.

"Cassie, my little cheerleader...you are the freaking best."

And with that I could not hold it and released a huge load all over the sheets. My body quivered like never before.

Then Lisa talked to me in a whisper as she gently removed the strap-on, laid me down in the bed and cuddled up behind me.

"Cassie, no guy will ever be in you as long as I just was. It may hurt at first, but you need to learn how to relax before he gets to the point of coming inside you. Slow him down with your words and relax."

"Some boys will be rougher than others, some cocks will be longer, some thicker, some smaller. But you will be able to enjoy them. You control what happens."

"Their emotions will be going crazy...loving every moment of being inside you. You might not be at that same place as they are when they explode inside you, so be ready for that."

"Make them feel like they are the best you ever had...ever."

I think I heard what she was saying but I was still in a daze.

After a few minutes of recovering, Lisa said, "Why don't you take a shower I will make us a light lunch."

She handed me a cute pink sundress with matching pink panties that I had not worn before, gave me a comforting kiss and I headed in the shower.

My head was spinning and my butt was sore, but I felt good. It was so satisfying and it was like another milestone. How could instruction and erotic times feel so good with her?

The rest of the afternoon was spent going through skirts, blouses, jackets, wraps, shawls, all kinds of fun things. We were like two best friends helping each other dress, playing and complimenting each other.

Never in my wildest dreams did I expect to be having this much fun. We teased each other when outfits didn't fit. We grabbed each other playfully pretty much at will, and faked orgasms as we rubbed each other in sensuous places. At times I wished Mr. Warren wasn't coming home.

By around 3:30 we had pretty much set up a game plan and decided to get dressed in nice dresses to welcome Mr. Warren home.

I was going to be young Cassie and Mrs. Warren was going to dress a little older and wear her dark rimmed reading glasses..

When Mr. Warren arrived promptly at 4:00, I removed his jacket and handed him a drink. After he had a sip, I gave him a big kiss and lifted one foot up behind me to act cute as I kissed him.

I told him "All my school girlfriends want to meet you. They are so jealous of me. They all want to suck your cock but I told them you were all mine!" He liked that.

I walked him over to the couch and Mrs. Warren began instructing me as to what to do and I had to obey her. This was all done in a nice way, calling her ma'am all the time. Not it a mistress type of way but a respectful type. It was fun and playful and he loved it. She knew what he liked.

After about ten minutes of this playing around, I excused myself and changed into naughty Cassie by putting on one of the corsets, long black stockings, panties and a black robe. I was to stay in the bedroom until Lisa came in.

She was playing with him as I was changing. She then told him she needed to check on me and wanted to freshen up. After a few minutes, Lisa left him, headed into the bathroom and turned on the shower.

I pretended to sneak out of the bedroom all underdressed carrying a gown and asked, "Would you help me into this long dress?"

I opened the robe and he loved seeing me dressed in a black corset, stockings and panties. I hinted that if we hurried we would have a chance to play a bit while she was showering.

I told him I wanted to suck his cock so bad. In fact I wanted to do it all day at school. He was to keep a look out in case she came out of the bathroom.

I straddled him with my long legs on the arms of the chair where he was now sitting and began kissing him before sliding down and started to give him a blow job

The shower stopped and she came right out, catching us. She made him stand up on a chair and watch me in the mirror give him a blow job. It was a pretty good feat but kept him from going off too early.

We then left him step down and she and I left the room for yet another change into some oldie but goodie dresses which were so much fun to primp in.

The final show featured us in long nighties, robes and heavy sexy make-up. After a little modeling and letting him touch us all over, we brought him into the bedroom and helped him to change into a robe.

Lisa tied a blindfold on him and lowered him back onto the bed. She and I took turns and began lightly sliding our bodies on him in our slinky outfits, giving him teasing little blowjobs along the way.

The blindfold was a great idea because we had two vibrators going as well. This kept Lisa as busy with her vibrator on herself and me.

As I was crawling over him and whispering his name, he actually ran his hand down my body, reached under my nightie, found my cock and started stroking it through my panties.

It was electrifying. This was the first time a male touched me while dressed and I loved it.

I moved my hips to at least acknowledge that I liked it and then his hand moved back to my breasts. Although they were small, I knew he liked that my nipples got hard with his touch. He returned to my cock again and seemed to enjoy feeling me getting excited by his touch.

After him touching me, my mind was racing and I was ready for anything. I decided that it was time to finish Mr. Warren to completion. His cock was already nearly purple and really hot.

I began licking his cock slowly and then hungrily took it deeper and deeper into my mouth. I could sense him pulsing more and more and finally he exploded. It was hard and fast and he drove it deep into my throat. After about 30 seconds he slowed and I stayed with him for several minutes as he quivered, remembering Lisa's story about not spilling a drop.

When I looked over, I saw Lisa leaning back in the chair beside the bed with her legs apart and a large dildo inside her. She had her small vibrator in her other hand and enjoying every minute watching us.

With Mr. Warren out, she motioned me over with her index finger and then to her lips making the shhh sign.

She laid on the floor and undid her robe exposing her breasts. She guided me on top of her with her as I straddled her. She took my cock in her hand, added some lotion and placed it between her breasts, slowing massaging her nipples with the head of it. She was smearing her nipples with my pre-cum and breathing deeply.

I leaned over her and she took my nipples hard in her mouth and I began rocking back and forth on her, driving my cock along her stomach and chest.

She then rolled me over onto my back and she straddled me. She glanced over and made sure Mr. Warren was still pretty much out and began to rub my cock between her ass checks. She was all lubed up and it was so hot. I really thought I was in her. I kept driving my hips upwards into her and she was grinding her ass on me. I could not stand it and exploded.

When I opened my eyes, she had this amazing satisfied smile and gave me a wonderful deep kiss. She took my hand and we quietly went into the bath.

We were both equally a wreck and kind of laughed at ourselves in the mirror. She helped me out of the wig, earrings and make-up and then we both stepped into the shower together.

This was another first. After a couple of minutes of relaxing and working on my face make-up, she took a soft sponge and slowly worked on me top to bottom.

"I miss doing this," she said. "I hope you don't mind this extra attention."

My nipples were red and enjoyed the soft feel of the sponge over them. As she continued down my body, I started getting hard again. Her hands reached around me and when she lathered my cock, it was nice and warm, and it started growing even more.

"Two times in 15 minutes...I'm flattered." She slowly and gently stroked my cock and it got harder and harder. With one of her hands on my breast and the other on my cock, I exploded all over the shower.

"So, Cassie can have multiples just like me," she whispered.

We toweled each other off and I almost collapsed coming out of the shower. We each dressed in the living room, she in her classic commando look and me looking like good ole Matt.

We slowly made our way to her car, and on the drive home she asked, "What was it like when Mr. Warren reached over and started stroking you? I never saw that one coming. "

"I really liked it. I wasn't sure if I would, but in the moment, it felt so nice. Knowing that being with him gets him that excited means a lot. But then again, it must make you feel that way when he responds to your touch as well."

"It does," she replied. "And just to repeat what you asked earlier, I love seeing Cassie and him together. I'll be curious to see what he has to say about the encounter when he awakes, whenever that is." We both laughed.

Shifting gears she asked, "Do you have plans for Thanksgiving?"

"Yes, do you remember my cousin Kate I told you about?"

"Oh yes, the one who has known about Cassie for a while now? Are you seeing her?"

"Yes, and three of her female friends from college. I am so nervous."

"Cassie will do fine. You are a much different person now. Be yourself. I love the Cassie I get to be with when you come over, and not just the sexual part. "

"That means a lot to me," I replied.

We continued talking. As we got close to my house she reminded me,

"And we head closer to Christmas and New Years we will be traveling and most likely not see you until after that. But, we promise to get Cassie a wonderful Christmas gift when we return."

"Oh, and I almost forgot. And I got a call from Cleopatra. She's having a get together right after we get back in January. Her husband is away for a long business trip in Europe so it will be quite an event. Would Cassie like to attend?"

"With Cleopatra?...I would really like that. She was a lot of fun in her own way."

"And I hope to have my own car by then. Once this semester is over in a few weeks I have been lining up some inside painting jobs so that should put me over the top to buy my own car. I hate having to ask for rides everywhere."

"I understand, but I'll miss our talks."

She took my hand, leaned over and gave me a nice hug before I left.