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  • Becoming Cassie Ch. 02

Becoming Cassie Ch. 02

When the fall came around, my opportunity to babysit was reduced a bit. I still wanted to, especially with the Warrens, but it looked like it was going to be on a once a month basis with them as there were less events and less nights out for them. September is like that.

They called me in late September call and it was a real busy time for me. With sports and homework in my first semester at college, it seemed like even my time to think about cross dressing was reduced.

I had done gymnastics and played soccer in high school. I was fast and nimble by all accounts there, but at college, the level was really high. I was working very hard in practice and getting very little playing time. It was frustrating. The best news though was that I was fit, real fit. And being 5'9" with effectively no body fat and fit made cross dressing so much easier, if I ever got the chance again.

I was commuting with friends to school. My mom couldn't afford my room and board, and that was OK, but it was taking a toll on me as well.

But despite a tough first month at school, I always liked the Warrens as a couple and said I would be glad to watch Benjamin this Saturday night.

When I got over there, I chatted with them for just a bit as they were making their final preparations. That night Mr. Warren had on a sharp looking leather jacket over a crew shirt and Mrs. Warren was wearing a shorter than usual black empire style dress and some pretty high heels.

I loved seeing her dressed, plus I probably could guess what she was wearing underneath. I told them they both looked very nice and they thanked me as they headed out the door.

Shortly after the little guy went to bed, I walked into their bedroom, put on a black bra and matching panties. I looked through her closet and found a similar black empire dress, took the wig out of the box in the back of the closet, applied a little lipstick and slipped on the heels.

I could now get dressed in about 15 minutes at her place and knew exactly which articles of clothing fit and which looked good on me.

I stood in front of the bedroom mirror and looked at myself from every angle. I was getting real good at putting outfits together. Heck, I could be Mrs. Warren's sister!

I walked into the living room, read a few articles from Cosmopolitan, looked at all the gorgeous advertisements and decided it was time for round one.

I slinked my way down to the bedroom, grinding my hips all the way and flirted with myself in the mirror from every angle again. I then moved into the bathroom and hiked up the short dress, slid the black panties over and began slowly stroking my cock. I loved this time. I was never in any rush to cum because the immediate downer that followed until I recharged.

I kept telling myself how good I looked and how much I wanted this. I must have been there a good 15 minutes, controlling myself, getting excited again and then, bam. I exploded and it was real good. Being away for a month was rough!

I kept stroking myself until the last drop came out into the sink. That was so satisfying!

I then cleaned myself off several times with a warm face cloth, waited until I completely stopped dripping and then headed to the living room to do a little homework...in girl mode, no, in babe mode.

I had a big history test coming up so I broke out my book and my notes and started at it. I loved this studying dressed. This was definitely something I could not do at home. I sat there all dressed up in a wig and heels with my legs tucked under me.

The Warrens had mirrors almost everywhere and could see my reflection whenever I looked up. This was so much fun! And so relaxing...

The next thing I knew, I heard the soft gentle voice of Mrs. Warren sitting next to me saying, "It's time to wake up little one."

My first reaction was..."Is Benjamin OK? I must have just nodded off. I'm so sorry. I'll go check."

As she lightly stroked my cheek she said, "He's just fine. He's sound asleep...just like you were young lady. And I can see you've been hard at work studying...my little beauty."

Then it dawned on me. I was still dressed!

Mr. Warren was standing there smiling at me and she was sitting there holding my hand. I was so embarrassed.

She then said to me, "Here, let's go into the other room and get you cleaned up a bit. Looks like you have had quite a busy night."

She led me by the hand into their bedroom. I was still groggy from waking up from the sleep. My thoughts were racing every which way. I was so waiting for an explosion from them. I know they were going to call my mom. I was trying to conjure up any excuse but none were coming.

Standing in her room she walked behind me, softly lifted my hair from my neck and slowly undid the zipper on the dress. The smell of her vanilla like perfume filled my nostrils.

Gently she slid the dress off my shoulders and carefully placed it over on the bed, right beside the nightie I had laid out there earlier. This was getting more embarrassing.

She then turned and looked at me standing in her heels, black bra and panties and sighed,

"Oh, I remember being that young. Youth is so wasted on the young. Please, come over here and sit at my make-up table."

She started removing some of my make-up and then picked up one of her make-up brushes and said,

"I think you need some eye shadow and blush to help bring out your features."

Now I was totally embarrassed and confused and asked..."Aren't you mad?"

"Oh no, silly. We are actually relieved a bit. We called earlier and when you didn't answer, we decided to come home a bit early. I had actually forgotten that I turned the phone ringer down earlier in the day so you probably could not hear it anyway...my little sleeping beauty."

As she kept applying a little more make-up she continued, "We were a bit worried so when we walked in the kitchen door we were very quiet. We didn't want to startle you so. You were sleeping so soundly that we chatted in the kitchen to decide what we should do."

"You looked so adorable with the book in your lap. Oh, do you want to see some of the pictures we took?"

"You took pictures of me??"

"Absolutely...you were so cute...especially sleeping in my clothes."

"So, do you like dressing up as a girl?" she asked as she applied more make-up.

Seriously, what could I say? I was sitting there in her wig, bra and panties.

I swallowed deep and replied "Yes, very much."

"How long have you been doing it? And does your mom know?"

I sheepishly replied, "I have been wearing lingerie and dressing for as long as I can remember and my mom does not know. She would most likely ground me for the rest life if she did find out."

She listened as she kept applying more make-up, blush, mascara and lipstick, always moving back a bit, admiring her work, and then applying some more. She kept asking me more and more questions.

"You're a lot like me I think. Do you like to put on pretty things, walk around and check yourself out in the mirrors?"

"Yes, I do. And Mrs. Warren, you do have the most wonderful clothes, but I'm very embarrassed about wearing them. I'm so sorry."

She then went into her closet and selected one of her more slinky tight dresses and said, "Let's see what this one looks like on you."

She steadied me in my heels and then slid the dress up and over my shoulders. As she adjusted the shoulders and neckline she said...

"Oh, that looks wonderful on you. Do you like behaving as a girl too?"

"At times I do. At home when no one is around, I enjoying pretending I'm the woman of the house. I even enjoy folding laundry with my mom and helping out with cooking, but I never dress at home unless I have secretly slipped on a pair of panties while doing chores."

As she was checking me out head to toe she signed and said, "Come back over here and hold still. Let me fix your make-up one more time and adjust your wig...ah...that's better. Now go and take a look at yourself in the mirror."

When I finally got to see myself in the full length mirror I was shocked at how amazing I looked. I was not longer just some boy in a wig wearing girl clothes, I was a freakin' hot babe. What a difference some sultry eye make-up, blush and the proper lipstick made!

She could see the bulge rising in the front of the dress as kept checking myself out.

"It appears that you like the look as well. Do you like to play with yourself when you are dressed?"

OK, this was a tad more personal but with a raging hard-on, it was hard to deny.

"Yes, it seems I get real excited real fast when I am dressed. I usually have to masturbate a couple of times in an evening. But I'm always careful not to ruining anything I might be wearing. I'm so sorry."

"Well, you must be very good at it because I have never noticed a thing amiss when you have been here. Now turn around and please tuck yourself in a little more."

I did my best to calm down and tuck my penis between my legs. As embarrassed as I was, it did not reduce my excitement. When I turned around she said,

"Mr. Warren and I have a surprise for you. Since we got home a little early and since you're not expected home for a while, you get to stay and play with us for a while rather than just yourself!"

"I'm not sure I would be comfortable with that Mrs. Warren."

"Really?", she continued softly and stroked my hair gently and walked around me.

"I think someone who dresses up in my clothes and wears my bra and panties, and masturbates in my house probably owes us a little something. Don't you think? I would hate to have to show these pictures to your mom," she said with a wry smile.

"But I am not sure I can handle this. I have never been with anyone before."

"Honey, turn around and look at yourself in the mirror again. I see a beautiful, hot young lady that any man would want to be with. Do you see her also?"

I had to agree. I looked better than I ever expected in any fantasy.

"Sit down and let me tell you a little about Mr. Warren, he is gentle. You will not find a nicer person. He likes to be teased and flirted with. Just follow my lead and I can assure you, this will be fun for you too."

"Oh, but, we can't call you Matt. What girl name can we call you? "

I had to think for a moment and replied, "I've always liked Cassie"

"Then Cassie it will be. And please call me Lisa while you are Cassie."

She took my hand and walked with me into the living room.

"Alan, I would like you to meet our babysitter Cassie."

He got up and greeted me with a little hug and kiss on the cheek. I had never been kissed as a girl before and strangely, I loved the attention.

"Cassie, you are beautiful."

"Thank you Mr. Warren, that is so sweet for you to say."

"Please, let me see what you are wearing."

I did my best to twirl around in my heels. This time he took my hands and gave me a kiss on the lips. Now this was different.

I arched my back up and pressed my little breasts into his chest. I could feel him getting excited them more he embraced me. He dropped his hands and softly caressed my butt.

"Please, call me Alan, and come sit on the sofa next to me."

As he sat down in the middle, I sat next to him on the left of the sofa and I pulled my legs up under me. He placed his hand on my thigh while Lisa sat on his other side.

"I could get used to this," he said as he looked at both of us on either side. For several minutes he gently rubbed both Lisa's and my upper thigh. I could hear his breathing become deeper. I was actually enjoying this as well. I loved his touch...he was gentle.

Lisa then looked at me as she unbuttoned Alan's belt and pants. With a little nod from her I got the idea it was time to help her slide his pants off. Together we slid his pants down to his ankles first, and then his briefs.

Alan was now sitting there of the sofa with a semi-erect cock and his eyes closed. I was no longer excited, but nervous. This was unchartered territory for me. I had never seen a penis this up close and personal n my life.

Lisa slowly reached behind her, placed some hand lotion on her hands and then reached over and gently placed some on mine. Watching her eyes she directed me to slowly rub Alan's cock with my hands along with hers.

Other than my own, this is the first cock I had ever touched. I was amazed at how he responded to the littlest touch and was fully erect in seconds. "Cassie, this feels so wonderful...please slow down a little."

Slow down? I had barely started.

I backed off and moved to caressing his thigh instead. He like that and stayed fully erect. I kept watching Lisa and followed her move as she slid her hands down underneath his balls. He slowly spread his legs out and made them easier to reach.

I replaced her hands with mine and kept cradling and lightly playing with them as she had. Watching Lisa, I slowly slid my upper leg on top of his like she did. After just a few moments, I heard Alan deeply moan with pleasure.

Lisa then let me know through her eyes it was time for him to cum. With one hand under his balls and my other one now around his cock, I began the slow tender stroking. Lisa smiled in approval and as he climaxed. Lisa had a small hand towel ready in her other hand to catch the hot semen. She was good. I kept slowly stroking him until he stopped.

"Cassie, that was so wonderful." I leaned over and gave him a soft kiss on his cheek.

Lisa then asked me softly, "Cassie, please get a warm face cloth from the bathroom." I did she showed me how to gently clean him up. He was so peaceful. And then within minutes, Alan fell fast asleep.

Lisa then whispered, "Let him sleep, I have something else to show you. "

She took me by the hand and led me into the bedroom. Lisa asked me to sit on the bed beside her. She smiled and began to lightly stroke my face, arm, shoulders, and thigh as we talked.

"How did that make you feel? You know, being with a man", she asked.

"Different than I thought, I guess."

"How so?"

"First, before I explain, I absolutely love the way I look. Your make-up is fantastic and I absolutely adore your clothes! But you kind of know that already. I love being Cassie!"

"I've fantasized over what it must be like to be you with Mr. Warren all the time. But I think I had too many expectations about what it would be like."

"It just didn't get me as excited as I thought it would. I really liked getting kissed...twice...a lot...and I really, really liked knowing that what I did got him that excited. But it seemed to end there. I'm sitting here now like nothing happened at all."

"Welcome to my world."

"What do you mean?"

"Well, I love Alan. He is wonderful and is a terrific provider, father and husband. But our sex life is not quite where I would like it. He's kind of a one and out type of guy. Loves to step up to the plate but can't go nine innings. Sometimes we don't even get through the batting order. Does that analogy make sense?"

"But he fancies himself as a great lover. It does get real frustrating for me."

"So what do you do then?"

"That's what I wanted to show you." She reached over to her dresser draw and pulled out a small vibrator. "This is a girl's best friend. Let me show you."

Sitting up against her headboard, she gently closed her eyes, turned on the switch and slowly began moving the vibrator over and between her thighs and then under her dress...which was real short to begin with. Within about one minute, her hips began to start rising up to meet the vibrator and any sense of modesty she might have had was gone.

She pulled her dress up above her black panties and started breathing deeper and deeper. I was watching her moving the vibrator right to those special spots that only a woman really knows. As I watched in amazement, I was getting harder and harder myself. She finally let out one long moan, turned the vibrator off and effectively went limp in the bed.

She then smiled with her eyes closed and whispered..."That was sooo good."

I could not say anything meaningful. I just sat and stared at her lying there.

"Come, lie here beside me."

"Cassie, I don't know exactly how you feel dressed up as a girl, but I know that every time I get dressed, I love it. I love the attention it brings to me and I love that it gets my husband excited."

"I also like that other things gets me excited as well. Like seeing you tonight when we got home dressed in my clothes. It was a shock at first but it actually turned me on...a lot. I told Mr. Warren, let's have some fun."

"He had his fun, I had mine and now it's your turn."

"Cassie, go change into the black baby doll nighties on the chair over there. You know, the one you had placed on the bed earlier. I figured you like that one."

I hated changing out of this slinky outfit, so when I stood up I looked at myself in the mirror one more time. I then removed the dress and then the bra, and tried my best to tuck in as much of my hard-on as I could between my legs in the panties.

I slid on the black baby doll I then looked at myself in the mirror, with full make-up. Crap, I was still gorgeous, especially in the soft lighting.

"Stop admiring yourself so much and come back here little Cassie. Lay back on the bed. Let's see if me and my little friend can make you satisfied as well."

Before she turned on the vibrator, she began lightly kissing my nipples through the nightie. She then worked her way down towards my cock while she used her hands to lightly play with my nipples even more. Lisa then turned the vibrator on the low setting and slowly began working it around my cock and balls.

My breathing got deeper as I tried to take in every minute of it. She then slowly pulled away and I could relax a bit. She was always whispering nice little girl thoughts to me and made me feel beautiful inside.

This went on for about 20 minutes. It was as if she loved every minute as much as I did. It then got to the point when I could not hold out much longer and told Lisa "I am so close."

"Cassie, my beautiful young lady, you are so sexy. Let it all out and enjoy." With that I had the longest and best orgasm of my life. She kept the vibrator on my cock until the last drop filled my panties.

"Cassie, you and I are going to be the bestest of friends!" With that she gave me a deep kiss and said..."Stay here for just a minute and let's get you cleaned up."

Lisa came back with a warm wet towel and gently cleaned up every trace of semen. She helped me change and removed every trace of the make-up. When I had changed back into my boy clothes she smiled and said, "Matt, I hope you can come back again."

"I would love to Mrs. Warren."

As we walked through the living room to pick up my books, Mr. Warren was sound asleep.

"I think we will let Mr. Warren sleep it off and I will drive you home."

Before we left, she tucked a parting gift of two pairs of her panties and a bra into my backpack. "Keep these as a remembrance until next time."

As she was dropping me off she said, "Hopefully we will see you in two weeks? We have a formal gala on a Friday night at a museum hosted by Mr. Warren's company and I know Benjamin would love to see you again."

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