Becoming Cassie Ch. 03

"Jennifer, she does amazing work. I mean, just look." I spun around and tried my best to be as sexy as I could. " She knows exactly how to handle every little detail."

Mrs. Warren then offered to take a few pictures of me by myself, and then me with Mr. Warren. And Mr. Warren took some of me with his wife.

Truthly, I now loved the idea of having pictures plus there was no possible way anyone could recognize me anyhow. We even used the remote timer and pictures of all three of us.

We stood talking for a bit and they shared some tales from the fundraiser. I asked about the ladies outfits and got a blow by blow description of the hits and misses. Even Mr. Warren contributed a few fashion observations.

"And Benjamin, does he ever wake up? He is so good. You two are so lucky."

After about fifteen minutes it got to that awkward stage in the conversation so I took a major step.

"Here, Mr. Warren, let me get you comfortable." At that point I walked over and removed his tuxedo jacket from behind. Carefully I folded it and laid it on a chair.

I moved back behind him and reached around him with both arms and placed both of my hands up on his chest in a hug. He really seemed to like that. I then slowly ran my hands down his shirt to his groin and began lightly caressing his cock through his pant. I could feel him getting hard.

Lisa was staring at me almost in disbelief and said, "Cassie, it looks like you know what Mr. Warren likes. Let me help from this side."

Lisa kissed her husband and then undid the tuxedo pants, which was not the easiest thing to do. She let them drop to the ground as she reached her hands around his butt and slowly began sliding off his briefs. As she was reaching back and rubbing his butt, she was also sure to touch me as well.

"Cassie, come over this side with me. I want you to experience what I am feeling."

I slowly walked around and knelt down beside her. I watched as Lisa took his semi-erect cock into her mouth, first in little amounts and then progressively larger ones.

I then said, "Mr. Warren, I want to thank you for this beautiful gown and lingerie. I hope this is a good start at thanking you."

By now Lisa had her hand inside my gown and was lightly caressing my breasts. I was getting more excited and started playing with his cock. I followed Lisa's lead and started with my tongue and then took him in my mouth. His penis was not huge like some I had seen in our sports locker room showers, so that was a plus. It was actually quite pleasant.

Lisa kept kneeling beside me and was giving me little non-verbal hints like wiggling her tongue, opening her mouth wider, and moving her head in and out. I took these cues, and loved her little facial expressions. It was almost funny to watch but hey, I was getting real on the job training. And there was no way he could see us.

As I took in more and more I could feel Mr. Warren backing away so I eased off. I knew that move all too well from myself. I then had an idea to slow things down.

I slowly stood up and asked "Mr. Warren, would you like to see my new underwear?" I still could not call him Alan and I think he liked the Mr. Warren thing with me. And I was always careful to call Lisa Mrs. Warren in his presence. This name thing was getting tough.

Lisa stood up to help me remove my gown and there I was standing about five feet from him wearing the sheerest of black lace panties, a sexy black bra, heels, make-up and a blonde wig. "Stunning" was all he could say. "Simply stunning."

Then Lisa, in a surprise move did the same thing. We were both there, without gowns in matching lingerie.

Almost on cue, we each grabbed a hand, led him to his favorite chair and had him sit back to enjoy the ride. Lisa sat facing him on the arm of the chair, slid her bra up and placed one of her breast right in his mouth. I knelt down at his feet and began playing with his cock again with my tongue. This was actually more enjoyable than I imagined.

"Mr. Warren, I love your cock and want you so bad." That little phrase changed things immediately. Not only did he get rock hard right away but he started moaning like last time.

I knew what was about to happen but this time there was no Lisa with a towel. Lisa was busy having her breast chomped on by her husband. I could hear her moaning as well.

I could feel his cock getting hotter and harder, and then it started pulsing . I knew he was cumming. I was not really prepared for this but at the same time could not wait for it to happen. I took in every inch of his cock as deep as I could and sucked out every drop.

He shuddered, moaned and virtually collapsed, if that's even possible in a chair.

I stayed down there for several minutes just kissing and gently sucking on his cock. Then I felt a soft hand on my back and it was Lisa.

She whispered, "Let's let him sleep". We then put a small throw over him to keep him comfy and picked up our gowns.

When we went into the bedroom, I could not help but notice Lisa wince a bit as she slid her bra back over her right breast.

"Are you OK", I asked.

"Yes, I'm just a little tender. He is usually so gentle I was just surprised. It really was a nice change, I actually got excited from him being excited and grabbing me. He's generally very passive."

She then asked, "Can we change into something else? I've been in this bra all night and I would really like something different to wear." Lisa went over to her drawer and looked for a nightie for each of us.

She said, "I seem to be missing a couple."

"Oh yeah, that was me. I got way too excited earlier tonight."

She put her hands on her hips and laughingly said, "Well young lady, I want to hear all about it."

She tossed me a pretty pink short nightie and panties. "That one will go wonderfully with your blonde look tonight." She put on a light purple one herself.

We sat on the bed like two best friends at college all the while gently caressing my arms and lightly playing with my nipples. I told her all about the entire evening, including my getting so excited...twice.

While she was stroking my hair and kissing my shoulders she asked, "So you and Jennifer really went at it?"

"It wasn't my idea. Really. I was trusting what she was asking me to do and then, well, things happened. And she never even took off her pants. I don't get it"

Lisa laughed and said, "Let me tell you about Jennifer. I met her at the athletic club I work out at a few years ago. We were in one of those 6 week challenges. It was a fun time and being athletes at heart, we started a friendship...always encouraging each other in workouts, diets, stuff like that."

"Then one night after a workout, she and I stopped for a drink and we started sharing personal stories. We both played sports in college and the more we talked the more we found we had in common. We even both had intimate experiences with our teammates."

Lisa crawled behind me and began kissing my neck and continued playing with my breasts. She continued...

"So Jennifer and I hooked up one night after a class at her place and we felt that there was chemistry between us. She likes to be more of the dominant one and I like to be more of the submissive type when we are together."

"And when you told me she was wearing her jeans, keeping her legs together and grinding you, that makes all kinds of sense to me."

Moving her hands down lightly to my thighs and then slowly around to my lower back she asked, "Cassie, what was it like when she penetrated you from behind with her fingers? Did it hurt, was it pleasurable?"

"Actually, both. I was not expecting it at all but I definitely enjoyed it once I could relax the muscles back there."

"Are you sore now?" she asked as she let her hand trail of my thighs and onto my backside.

"No, not at all, why?"

Lisa kissed me again on the shoulders, got up and went to her closet. After a minute of her moving some boxes around she returned with something that looked like a belt with a penis attached to it.

"Have you ever seen one of these?"

My look pretty much answered her question.

"It's called a strap-on and girls wear them when they get intimate with each other."

"This is a small one and I keep it around for when a friend, like Jennifer or someone, might stop over and we play a bit. They come in much larger sizes, but let me show you how it works."

Lisa walked over to her nightstand, dropped her panties, put on the belt and positioned the strap on so the base of the penis would press against her perfectly. "Oh," she sighed deeply, "Even that feels so good."

She then looked at herself in the mirror and said, "I'm sorry, I have to take my nightie off. This just looks too weird in a nightie."

In the dimly lit bedroom, I thought she looked amazingly hot. And if even possible, I started getting even more excited. She took some lubricant from her drawer and softly said, "I want you to kneel on edge the bed and bend as far forward as you can...and relax."

Lisa kissed my arms and my back a few more times and then slid my panties down. She took the lubricant, reached under me and slowly began lightly massaging my cock and balls. She whispered, "How does that feel Cassie?"

She then slowly began to apply the lubricant up along my butt and began playing with and probing my hole with her finger. I could now vividly remember that feeling from Jennifer. Every minute or so Lisa would go a little deeper.

After several minutes, I could feel her two fingers in me and it almost took my breath away. All the time Lisa kept whispering nice, supportive words, like, "I want to be in you little Cassie."

I then started feeling the pressure of something bigger than her fingers. It was slow and constant, and to some degree hurt until my muscles relaxed. I could now feel the cock inside me.

Lisa held still as I kept adjusting to this new sensation. The mirror was still in the room and as I looked to my right, there I was with this awesome brunette with this cock penetrating me from behind. Lisa kept her hands softly on my hips and continued talking to me and telling me how beautiful I was. She even reached up further and began playing with my nipples with one of her hands.

She then added some more lubrication and slowly started with the littlest of movement...going in a bit and out a bit. She continued with slightly larger moves and the feeling was overwhelming. And the more I looked to mirror the more excited I got.

I could see out of the corner of my eye that Lisa was checking out herself in the mirror as well and was now using one of her hands to squeeze her left breast and kept the other one caressing my back.

Her lunges got deeper and deeper, and her moans got louder and louder. "Cassie, you are so beautiful." I could feel her legs shudder from behind.

The pleasure was finally so intense that I grabbed my own cock and masturbated all over the bed. It did not take much. I practically collapsed as she slid the cock out of me.

Lisa joined me on the bed and as she laid there on her back...and with the strap on cock standing straight up...it left me with a surreal image.

I asked her, "Do you want me to get your vibrator for you?"

"No silly...I just had an amazing orgasm. Couldn't you tell??" She rolled over and gave me a big kiss and actually tickled me. "Cassie, you are amazing!"

I was not getting this female orgasm thing.

It took about 30 minutes to clean everything up. Taking off all this make-up was a chore. As I changed back into my Matt clothes, Mrs. Warren said, "Please keep the bra and panties. They're yours."

I put the new bra and panties into my backpack and asked Mrs. Warren if she could keep the dress and heels here. I was afraid my mom would find out if I brought too many things home.

"Matt, how many things do you have at home?"

"Not too many. With brothers and sisters poking around, I am always nervous of them finding things. Right now it's just the things that you gave me and few older items of my mom, an aunt and cousin."

Before we left, she asked, "We have a party coming up in a few weeks. We might host it here and it will have a bit of a Halloween theme to it. Would you be interested in coming?"

Thinking this was just another babysitting job, I readily agreed.

When she left to drive me home, Mr. Warren was still asleep in his chair. "Is he always like this?" I asked...

"Always"