Becoming Cassie Ch. 07


This was harder than I thought. I was trying to live as Matt and keep my thoughts focused on school, sports and life in general. Yet at the same time I couldn’t wait to be Cassie. And now there were all kinds of Cassies.

There was the Cassie in my mind who was happy just to toss on a pair of panties under some jeans and go throughout the day as Matt.

There was the Cassie that was real good friends with Kate and developing a niece-like bond with my Aunt Mary.

And then there was the Cassie who could not wait to be with the Warrens and whatever they were planning next. Exploring sexual fantasies with them seem so normal…as long as I was Cassie.


November was busy for me and the Warrens. I was rushing around at home trying to finish outside chores like outside painting as the fall weather had really kicked in. Soccer season was virtually over as we missed the playoffs but we had our wrap up meetings and light training.

And if I did babysit, it had to be babysitting. I still needed to make some money. I so needed a car and the only way I could get one was if I could save for it.

And I really needed to focus on my schoolwork…there were too many papers due and then final exams in mid-December. But then I would be free for a while. I never thought I would be this busy taking 5 courses.

I was only able to schedule one babysitting gig for the Warrens in November, and that was tight. It was a Thursday, exactly a week before Thanksgiving and I had a quiz the next day.

The Warrens had a simple business gathering/dinner on a weeknight and they expected it to be a short night. To some degree, that was good.

They asked me to arrive early because the event was starting at his office and then they were going to a restaurant.

When I arrived, I was surprised to see Mrs. Warren standing at the door, apparently waiting for Benjamin to come home from his playgroup. We stood and chatted for a moment and within a minute a nice black SUV pulled in and out popped Benjamin.

Along with him came another boy about his age and his mom. Benjamin ran over and gave me a hug.

“Matt, I like you meet Nick and his mom, Mrs. DiBona.”

“So glad to meet you, Mrs. DiBona” I said with a smile. I then rubbed Nick’s head. He had on an AC Milan jersey and was carrying his soccer ball into the house. “Nice shirt Nick!” He smiled back at me.

Mrs. DiBona said, “Sorry we are late. Nick needed a one minute potty stop right after we left and it ended up being a long one.”

Mrs. Warren said to all of us, “No problem at all. Please come in for a minute.”

Mrs. DiBona was blond and beautiful, with a fantastic figure. For picking up child at daycare, she looked amazing. I almost asked where she was going. Who wears a killer dress and heels during the day to pick up your child at daycare?

Nick put the ball down and lightly kicked it to Benjamin who kicked it over to me. We passed the ball around and I made a couple of fun moves with Nick. He laughed as he tried to get it away from me. I let him win the ball and he did the same with me.

“So Matt is Benjamin’s babysitter, and he plays soccer. What a nice catch Lisa. Matt, are you looking for any more work?”

I laughed and said, “Maybe, once this semester is over.”

“And a college man as well,” she replied.

They stayed for about 10 minutes, we spoke for a bit more, and then she and Nick headed out. I really caught myself checking her out as she left. She was a complete package for some lucky guy.

Benjamin showed me what he did at daycare and then went on playing. I sometimes forget that babysitting is what I came here for first.

In the other room, Mrs. Warren asked, “Well, what did you think of Mrs. DiBona?”

“From my whole 10 minutes of seeing her I can say she is very pretty and seems very nice.”

“If you were older, how would you like to date someone like her?”

“That would never happen, she is beautiful and apparently rich. Seriously, the clothes she was wearing in the afternoon and the SUV…she must be well off.”

Then she came up to me in an amazing sexy move and quietly asked, “Would you ever want to do her if you could?”

“Mrs. Warren, that would never happen. Plus, she seemed so nice.”

“I see how you could say that, but she’s really a witch.”

“Mrs. DiBona?”

“Seriously, she can be a real witch”

“I must be missing something.”

“Like…an Elvira witch.”

That stopped me in my tracks.

“No way.”

“And she and little Alice…”

“No way.”

“Uh huh…you did…or at least Alice did.”

“And Matt, this late drop off was absolutely not planned. I figured she was so drunk on Halloween that she would not even remember let alone recognize you. You didn’t recognize her either.”

“Her husband, or the Count as you know him, keeps her on a tight leash but also expects her to be dressed like that all the time…very possessive but loves to show her off.”

“But it is a nice thought to keep in your mind next time you see her. And I promise, I will never, ever say anything to her.”

“Now, I have to get ready for tonight. I need your advice.” Benjamin was playing in his room so she stepped into hers with me and closed the door.

Because of our Halloween romp, I could not look at her quite the same way and we both kind of knew it. It was a fun embarrassment that lasted for a just a minute or so.

Then she said, “Before I ask your advice, let me show you two new dresses I bought for some upcoming events.”

She walked me over to the closet and held up a red sparkly dress…this is for our Christmas Eve Party in Ohio.

“Beautiful, I love it.” I replied as I touched the material.

“And for New Year’s Eve, I decided on this silver one. What do you think?”

“They’re both gorgeous. I really hope I get to see you in them.”

“Oh, you will. But it will have to be when we get back. We are going to be away from just before Christmas at Mr. Warren’s parents in Ohio and then after a few days we fly to Aruba through New Years on vacation. You’ll just have to wait to see it until I come back.”

“Matt, would you help me out of this dress, I’m might go with this burgundy dress tonight.”

“That’s a good choice, that color works well on you,” I said.

It was actually nice seeing her in just a regular bra and panties. I loved the fancy ones on her, but these just seem more appropriate.

As I was helping her in such a non-sexual way she turned and gave me a big hug. “Do you know how comfortable you make me feel? I don’t even think twice about changing in front of you or confiding with about anything. I really appreciate that.”

“I’m getting to feel the same way too. I’m glad it wasn’t just me feeling that way.”

Then I asked, “Any requests for when you two come home?”

“Surprise us. Hey, my clothes are your clothes…except for these new ones I just bought.”

“Yes ma’am. I promise.”

“And Mrs. Warren, I just need to double check, are you OK with Cassie and your husband …you know…getting a bit intimate? The last thing I ever want is for anything to get in the way.”

“On the contrary, I love watching you two.”

Off she went to the party and Benjamin and I had two hours to hang out. We played a little soccer in the living room, had a little dinner, slowed things down and colored and then it was off to bed.

It took a few minutes for him to relax and then he fell right to sleep. I then tossed on a babydoll nightie, pulled on the wig and sat on the bed trying to think of what to do next.

It was tough coming up with an idea especially considering the Halloween extravaganza. It was going to be really hard to top that one.

I went over to her dresser and started looking through it to find something to wear that was different and would be fun. As I removed one item, looked at it and then placed it back into the crammed drawer. I then removed another and replaced it too. After a few minutes of this nonsense, I took everything out of the drawer and tossed everything on the bed.

I went deep into her closet and began pulling others out as well that were interspersed everywhere.

There were a lot of nighties. I started sorting them into styles. Babydolls, chemises, long ones, some with full bodices and some with spaghetti straps.

When I had gathered them all together into grouping there were 14 babydolls, 6 chemises, 9 long gowns and about 7 robes. I almost felt like this was a game show as I headed her pantie drawer and found the matching panties for more than half of the outfits.

This was like being in a lingerie store, and these were just the nighties. It really didn’t take very long to sort everything so I started the process of trying every item on.

I only got through about 5 of them before I got so excited in a new one I had never seen that I knew I had to masturbate soon or I’d ruin all of them.

I sat down at her dressing table, spent some more time on my make-up and headed to the bathroom and let it rip. Damn, did I look good.

Getting dressed and making my first bathroom trip was now almost a requirement in this household.

About 4 of the babydolls didn’t even fit, plus they were made out of this scratchy lace material. These had to be gifts because no girl in her right mind would ever try these on and then buy them.

As I kept trying them on, I worked more and more on my make-up as well trying to perfect my look for the different outfits. It was fun.

I literally tried on every outfit and made my own judgment over which ones I like more than others. I then hung up some of the long matching ones and neatly folded the others away.

At around 10PM I got a call they they were on the way home and should be there in 15 minutes. That was good, my make-up was still working great and I had decided what I was going to wear for their arrival home.

I moved over to the Bose system and selected one of their more romantic CD’s, dimmed the lights a bit and waited.

As I heard the key turn, I stood up from the far side of the room and slowly started my walk over to them. I tried to be as seductive as I could but still wanted to portray that “Honey, I’m so glad you’re home” look.

I was wearing a cute, ivory chemise, with a lace top. The soft chemise fell to the just above my knee and had matching panties with a little drawstring bow on both sides of the hips. I also had on the matching robe which was the same ivory color and style, but was floral as well. I let that stay open as I walked over to them.

“Cassie, you are beautiful! Where did you ever find this?” Mrs. Warren took my hands and just stood there looking at me. She then softly ran her hands down the fabric and lightly touched my breasts.

I never really replied to her question but slid over and welcomed Mr. Warren with a kiss and said, “Please sit down, I want to hear everything about this evening.”

Mr. Warren sat on the couch and I curled up beside him. Mrs. Warren sat directly across from us and started talking about the evening.

It was so comfortable just cuddling against him. It was so easy to just listen to the two of them talk as I lightly caressed his chest and ran my hands down to his thighs ever so softly. I could feel him getting harder and backed away a bit. I knew that excitement could end his night early.

They kept talking and I slowly undid his belt, opened his pants and just lightly stroked his cock as I sat there cuddling. I just wanted to make this feel natural and not super erotic.

As he was telling a story, I was able to slide down a little lower and began to slowly kiss his cock. I knew this was deadly territory with him so I worked very slowly, backed away, and played a bit with his balls.

When I felt he was in a safe place, I would slowly put more of my mouth over is cock until he got rock hard again.

After about 10 minutes of this, what started out as his comforting arm around me started to become a little more on the grabby side and his penis was beginning to throb. I slid away and nicely said, “I have a bit of a surprise for you. Let me show you both.”

As I stood up and adjusted my gown, Mrs. Warren gave me this wry smile of approval and asked me again, “Cassie, where did you find this sleep set? I had forgotten all about it.”

I took their hands and said, “Come, let me show you.”

With that I walked them to their bedroom door and let them open it. Hanging up in different places in the room were several nighties along with robes and matching panties, as well as two elegant lounging robes that had to be Mr. Warren’s. With the soft lighting, candles and music, it looked like a boudoir.

The two of them were like kids all over again. They truly had not seen some of these items in years. I could see them telling stories of the time they wore these or purchased them. It was a side of them I had not seen before.

I saw Mr. Warren starting to remove his clothes so I figured this was a good time to slip out, close the door and let them change. I went to the living room, sat down, opened up a Vogue magazine and waited.

I was trying to get myself excited, expecting that I would be sucking his cock to completion any time now. I was actually looking forward to it seeing I got shut out at Halloween.

After waiting a full 15 minutes, I closed the Vogue magazine and opened up my statistics book to study for the morning’s quiz. And I waited …and waited…and waited.

It was getting close to 11PM and I had classes in the morning. I was kind of in a jam so I crept down the hall and listened at their bedroom door.

It was quiet. No talking, no moaning, no anything. I listened even closer and it sounded like Mr. Warren snoring a bit.

Quietly I opened the door and there was Lisa, on her back, hair disheveled, one breast hanging out of her nightie, no panties on with her legs wide open, sound asleep.

I crept closer to see if she was awake and I couldn’t help but see her vagina was still moist and there was semen was between her legs and all over the bed in that area. Seriously, unless it’s yours, after the fact it’s not that attractive.

Mr. Warren still had on the burgundy robe of his I found and he was absolutely asleep. His cock had been reduced back to his normal soft size and looked pretty icky so I know he was done for the night.

Once again, little Cassie is all by herself and horny as hell. This was like Halloween all over again.

I quietly sat on the chair closest to her side of the bed. I needed to get home so I needed to wake one of them up, and I knew it wasn’t going to be him. He never wakes up.

Figuring it was going to have to be a fast exit when I did go, I moved the floor mirror a bit so I could see myself and sat back in the chair.

I loved this nightie, robe and panties. I even loved the make-up I did myself. I started playing with my nipples and watched them get harder and harder in the mirror.

I gently spread my legs like Cleopatra did at Halloween and slid my cock out of my panties. I tried to get into a rhythm and not get too loud myself.

I then heard Lisa stir a bit and roll over. I slowed down and waited to see if she had awakened but she was still sleeping. As I continued stroking myself I was getting closer and closer to cumming when I heard a gentle whisper…”Cassie…come over here.”

Lisa reached her hand out to me and I quietly moved to the edge of the bed.

She whispered, “Come, lie down her with me and let me cuddle behind you.” I gently slid my body onto the bed and she nuzzled up right behind me.

“Shhhh…”she whispered in my ear. She slowly reached her arm around me and began lightly fondling my breasts through the robe and nightie.

As she began to play with them ever so slightly, I could feel her nipples getting hard as they were pressing into my back. She was softly kissing my neck and shoulders.

“Shhhh…”she kept whispering. One of her hands reached down and slowly began caressing my penis through the ivory nightie and panties.

This was really nice. It was like she was making love to my penis with just her hand. So soft and gentle.

“Shhhh…drift away my little Cassie.” By then I was doing all I could not to explode. But it was almost like she was giving me permission too. I did my best to control any sound but my breathing deepened as I starting cumming long and hard.

“Shhhh…” she said one last time as my cock unloaded and filled the ivory panties. She stayed with me until I pulsed for the very last time. I don’t ever remember going for that long.

We just lied still for a few minutes. She kissed my back, and arms, and finally whispered in my ear, “I need to get my little girl home.”

Quietly I did one of my fastest clean-up and changes ever. Lisa did the same, but she looked different. She was radiant.

Once we got into the car I asked, “OK, Mrs. Warren, you have to tell me.”

“First, this is for Cassie.” She gave me the deepest kiss I have ever gotten in my life…tongue and all.

“Alan and I had the best sex in years. Pardon my English but he pounded the living crap out of me. I had forgotten how good it could feel.”

“Did you have an orgasm?”

“I lost count. He was amazing.”

“I am so happy for you.”

“Now, tell me about finding all the nighties and robes. Where were they?”

“Everywhere. Seriously, I spend so much time looking for things in your room when I babysit, I thought I would organize a few things of yours. I guess I got carried away. I hope it was OK. You did say your clothes were my clothes or something like that.”

“Yes I did. And I have to tell you, some of those outfits brought back such great memories. It was like they woke up a sleeping giant in him.”

“Like what?”

“We had real foreplay! He came down on me orally for the first time in years and he could not get enough of my breasts. It was so nice.”

“By the time he mounted me I was sooo ready that I just had orgasm after orgasm. It was fantastic. I think he’ll sleep for days.” We both laughed.

“And I have Cassie to thank…sorry for that kiss Matt, but now you know why I had to thank her.”

“You’ve been so good to us. Is there any fantasy you would like exploring?”

“Yes, I do have one fantasy…sort of. One day, could you and I take an afternoon and go through your entire closet and drawers, we could try everything on and then arrange everything? Kind of like a girls day in?”

“Let me get the approval from Mr. Warren. I don’t want him thinking anything other than the fun we all have together. But personally, I absolutely love the idea.”

“And Matt, good luck with your quiz.”


It wasn’t but a day later when Mrs. Warren called my mom and asked if I could babysit on the Wednesday before Thanksgiving. From our chat earlier, she knew I had if off from school and would be available.

I had wanted to relax a bit, but then again, what’s not to like babysitting at the Warrens.

I called her back to confirm the time and she discreetly said, “Matt, it’s going to be less babysitting and more organizing. Mr. Warren loved the idea and said that we could get together if we gave him a fashion show when he got home from work. It would be an early day for him.”

Now this was going to be fun. We agreed upon a time and now I could not what until Wednesday.

When I arrived that Wednesday morning, she was still in a robe. Once inside she gave me long, sensuous hug. “Well, 10AM is different isn’t it, young man?”

“To be honest, Cassie has been a night time person, so this will definitely be a different experience. I almost expected to see you in curlers and fuzzy slippers.”

We both laughed and she replied in a serious tone, “That’s exactly what I have for you to wear…just kidding.”

“But I did put a nightie and the wig out on the bed just to get you into the Cassie mode if that’s all right with you. Then we can have some coffee and figure out what we are going to do.”