Becoming Cassie Ch. 11

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
TGJamie
TGJamie
450 Followers

Laughing I said, "Oh yeah, I know exactly what you mean."

"And the hardest part for me is how they like to stand so close to each other and like to lightly touch each other."

"OK, got it. I will work on that. What time?"

"Can you be at Jennifer's around 7:30? I can do your make-up and then we can head out. It's only 10 minutes away. Oh, and what did you want to ask me?"

"It can wait. See you then."

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

Monday and Tuesday were good work days, but I kept dreaming of Tuesday night with Eric. It had been over a month and did my dreams exaggerate reality? Would he feel the same way?

I got over to Kate's around 5:00 and started to change over. Since Eric was coming from work, I decided on one of Kate's nicer dark dresses. This would be a nice contrast from the red Holiday Bash dress. Kate looked great as well.

We pulled up to the restaurant and Eric was there waiting with his coworker Justin. Nerves kicked right in and Kate came up beside me as we exited the car.

"Cassie, don't worry, you look wonderful and everything will be perfect. And who knows, maybe you'll get lucky!"

"And if you do, I'll disappear and will leave the door open for you," and she squeezed my arm.

After the introductions and a professional hug from Eric, we made our way in. Eric and Justin talked about their jobs and how much fun the internship was. I was so jealous of them, and kept asking them all kinds of questions. They loved talking about themselves and their jobs.

After dinner, Kate sensed that Eric and I wanted to be alone and paired up with Justin as we walked around the downtown area and chatted.

"So the company puts you up for a week? That's a nice internship."

"It is, but because it's an unpaid internship, they needed to do something I guess. And if it all works out well, I might get a paid one this summer."

In a bold move he said, "Would you like to see my place for the week? It's quite nice."

I think the way I was hanging on his arm, it was clear that I did. It was only a short drive from the restaurant. We said an awkward goodnight to Kate and Justin and headed over to his car. It was kind of like, "We're going to have sex now...goodnight."

The place was like a nice apartment complex rather than a hotel. We walk into this real nice courtyard that led to his room. "I think this would be a great place to sit around a fire pit if it wasn't so cold," he said.

With my head on his shoulder all I could think of it would be nice to sit anywhere with you, but replied with, "Yes, that would be romantic, especially if we were by ourselves."

The closer we got to the room, the closer we got to each other. Going into a hotel type room was a little strange at first, but the room was not just a room but a mini-suite complete with a separate little living area and kitchen. "This is like an apartment," I said as I walked around the unit.

Time passed quickly with him and I really don't remember all the things he was saying to me about his job, but I loved just sitting there next to him while he held my hand.

Finally, the words I wanted to hear woke me up..."Cassie, I really missed you this past month."

It wasn't a sexual comment but a genuine one. I was now eagerly listening to every word.

He continued, "When we met at the school, I thought that there was something special about you but then discounted it because of the excitement of event, us getting together later that night, and finals coming. But as the days went on, you were still there in my mind."

"Eric, I felt the same way," I said while looking at him with the biggest of eyes.

"That's a relief. I thought it was just me."

"But don't you date other girls, you know, genetic girls, on campus? Why me?"

"That is a question I don't have an answer for. There was just this connection and I have trouble explaining it even to myself let alone to anyone else."

"I do too. I just know I want to be with you." And then I asked,

"But what about Vera?"

"I've dated Vera a couple of times, but seriously, it was only about the sex after the first time. She's nice and all, but I'm not sure it will be an ongoing thing. We are not a couple if that's what you mean."

"It's kind of what I mean. I'm not good with understanding this relationship stuff, especially with a guy." (Oh, that was awkward.)

"And we don't have to. Cassie, can we just enjoy our time together tonight? I mean, I don't think we are going to do anything to solve the world's problems tonight."

"I'm sorry. I have been thinking about us for so long that all these random thoughts keep jumping out."

"I know, I feel the same way. Let's just give it some time, agreed?"

"Yes, agreed," and I gave him a kiss and a hug.

"Can I get you a soda or something?" he asked.

As he got up I followed him just to change the venue a bit. "May I take off my heels? They're fun to wear, but not for 4 hours."

"Sure. I can't even imagine it." Now I could stand in front of him and look up at him for a change. It made it easier for me to give him a hug as we just stood there. I could feel his cock hardening through his pants.

"OK, no more talking," I whispered as I pulled my body even closer to his.

We never drank the soda, and I lead him into the bedroom. For next hour we made love. There was no awkwardness now. Eric kissed me like he had done at his dorm. My eyes darted as his hands began to squeeze me all over.

It was so nice, we were making out with our clothes on and I was getting real excited. I loved feeling his hands running up and down my dress as he kept holding me in his arms.

I led him over to the nice chair beside his bed and straddled him as I continued kissing him. Then within minutes, he reached behind me and began unzipping my dress. It felt so good to have him disrobe me.

Feeling the dress come off over my shoulders and begin to fall off me was so sensual. Now my hair could softly fall on my shoulders and I felt like everything was in moving in slow motion.

After a few minutes I stood up and stepped out of the dress and carefully draped it over the dresser. He came up from behind me, reached around me and squeezed my breasts. I loved watching him do that in the dresser mirror.

I watched his reflection as he moved my hair aside and kissed my neck and then my shoulders. I was not only aroused but felt so wanted.

Our pace picked up as I turned around and unbuttoned his shirt. I continued giving and receiving quick little kisses. By the time I had his shirt off, I could feel his cock pressing hard against me through his trousers.

I undid his belt and then knelt down as I slid off his pants and underpants down. "I have missed you so much," I whispered and immediately took his entire cock in my mouth.

I had been longing for this so much. I so wanted every inch of it in my mouth and even that it wasn't enough. I was reaching around him with my arms and pulling his ever hardening cock deeper and deeper into my throat.

But, I needed to slow down. I was not going to make it through the next 5 minutes at this pace. Still in my black bra and panties, I led him to the bed and put my head on his chest while I played with his cock with my free hand.

"Eric, tell me what you like."

"Right now, this is perfect. I love your soft touch."

"Like this?" I asked as I played with the tip of his cock and slid his precum over it.

"Cassie, you always seem to know what I love."

With that as encouragement, I played with him a bit longer then straddled him cowgirl style, and slid his cock behind me. "Comfy?, I asked as I sat on his stomach and playfully kissed him

"This is so nice," he said as he reached up and caressed my breasts through the bra. That caused me to stretch up even more and push back against his cock.

I kept leaning over and kissing him and then sitting up, reaching behind me and playing his the head of his penis.

"Cassie, I want to be inside you so bad," he whispered.

"Eric, I've been dreaming of having you inside me...again."

I rolled over in the bed and he cuddled up behind me. Eric then slid my panties down a bit and began lightly pressing his cock into me. With his precum he began to try to penetrate me a bit, but I was not ready.

"Give me a minute, hun," I asked.

I reached over for my purse and took some lotion. As I went to use it he said, "Let me."

The smell of vanilla only added to the sensation and before long his finger slowly began massaging me.

"Oh...oh...that feels wonderful."

I just was lying there on my side with now two of his fingers inside me.

There was no rush. I was enjoying every minute of this, no, every second of it. "Cassie, you feel so soft," as he kissed my shoulders and arms while still massaging me.

"Eric, I feel so alive when you are in me."

Eric, now sensing I was ready, placed the lotion on his own cock and helped me into a kneeling position. He slid in so much easier than the first time. There were no stages this time.

"Oh...Eric," I moaned. I knew his feel and eagerly moved to accept all of him.

"I love it when you are in me," I said softly as he began slowly driving his cock back and forth into me.

Eric began increasing is pace and I could now enjoy the warmth of his penis inside me. "Oh Cassie..." He moaned as his penis began pulsing, shooting cum deep inside me.

"Please, please don't stop," I cried as I pushed back on him harder and harder. Having him inside me felt so...belonging. I knew he was done but he stayed in me as long as he could and then he slowly slid out.

As he rolled over on the bed, I went into the bathroom, got him a nice warm wet towel and hand cloth and cleaned him up. He just laid there motionless and moaned softly as I gently washed him and showered his soft penis with kisses.

As he rested, I cleaned myself up and did a major make-up overhaul.

I crept back into the bedroom, slowly got dressed and checked myself out in the mirror from a couple different angles. I really loved how this dress looked on me, especially in the soft glow of the evening lights. I was still horny, but it could wait.

When I was ready I moved back to the bed and gave Eric a kiss on his cheek.

"Eric," I whispered, "I have to leave. I so wish I could sleep with you tonight and be here beside you when you wake up."

I kissed him again on his cheek, and then his neck and his back.

I sat down on the bed and started putting on my strap heels.

"Eric, I need a ride back to Kate's." I whispered again.

Finally he cuddled up to me and said, "Just trying to savor the time with you. I just love watching you get dressed. I could get used to that."

"You were awake?", I asked as I lightly hit him.

He playfully grabbed me and kissed me one more time.

"Eric, are you excited again?" I asked as I slid my hands down to his hardening cock.

"Sorry, Cassie, I've got it real bad for you."

Even though I was tender in my butt, my mouth was fine. Equally as playful, I began lightly kissing his cock and taking more of it into my mouth.

"Can't you stay?" he asked.

Taking a break from sucking his cock, I looked up and said, "No silly, I can't stay. Not this time. But there will be others. I promise."

I gave his cock one more, deep swallow and then a light kiss.

Reluctantly he got dressed and took me back to Kate's. We had a great talk, shifting right back to work and economics, and I actually loved it.

I practically skipped up the walkway to Aunt Mary's house...the same walkway I was petrified walking on just two months ago. Cassie, you've come a long way.

When I arrived in, the house was quiet and everyone was asleep. I was expecting to have to give Kate a full accounting, but was so glad that could wait until morning. I was tired, and still horny.

As I got ready for bed, I went through the drawers of nighties and decided on the one sexy black nightie Aunt Mary warned me about to play in right now and the cute lavender one to sleep in.

I quietly carried them down to the bathroom, and as I slid the black one on before removing my make-up, I quickly realized how bad I needed to masturbate. My cock was still practically purple underneath the spanx.

My make-up was still working and the black nightie just fell perfectly, lightly caressed my breasts. I could not believe that this was one of Kate's nighties.

Slowly I began massaging my nipples and they got harder and harder. The little tuck of my cock into the sheer black panties was no longer working and I slowly began stroking it, just as if Eric was inside me. In my mind, I could still feel him in me pushing deeper and deeper, and it was wonderful.

I so wanted to wear this nightie next time he and I were together, and began dreaming that instead of me having a cock, that Eric could come inside my vagina. I was squeezing my nipples so hard with my other hand I nearly cried. I could feel him exploding inside me again as I came all over the sink.

My legs went weak and my upper body was trembling all over. I stayed there watching myself in the mirror and imagined what it would be like to wake up with him in the morning. Would it be everything I imagined?

I slowly removed the nightie and then the make-up and started the process of showering. I had a lot to clean up and was hoping the long shower would not wake anyone up. The lavender nightie was a perfect choice and I had a nice restful sleep.

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

I had two full days of work ahead of me and then the Bachelorette Party that Thursday night, so I got up at 8AM, had coffee with Aunt Mary in my Matt mode, gave her an abridged version of the night and promised I would be back. Kate never woke up but Aunt Mary said she sleeps forever these days and would update her.

The next two days were uneventful, just painting, making money, daydreaming and waiting for the Thursday night Bachelorette Party with Derek.

TGJamie
TGJamie
450 Followers
12
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
45 Comments
HST666HST6664 months ago

Please continue this story

SPRH85SPRH858 months ago

Will there be more.?

Carolyne131Carolyne131about 1 year ago

Great start to this story but it truly needs to be completed. Many questions arose about who knew Cassie's secret so a part about her mother and family finally knowing about Matt's feelings and direction he is going is necessary along with the parties, Derek, Kate, Aunt Mary and Eric needs to be addressed to make this story into an all time great. If TGJaime is unable to finish it, maybe she could assign someone else the task of finishing the story.

DiaperboyMiDiaperboyMialmost 2 years ago

What a truly Wonderful story!!!!!! I'm really hoping to see a new chapter. Thank you!!!!

AnonymousAnonymousover 2 years ago

The story you’ve written is really very erotic and captivating, It would be great if you could get back into it, and do more chapters, Cassies story needs to have more things, to show her growth into a woman, or something.it’s been just too good to just leave it hanging like this. Please write more to her story soon.

Show More
Share this Story

READ MORE OF THIS SERIES

Similar Stories

How I Became a Cheerleader Guy changes schools, life and sex to fit in.in Transgender & Crossdressers
My Feminine Side Guy becomes a beautiful sexy girl.in Transgender & Crossdressers
A Job in the Theatre Ch. 01 The Beginning.in Transgender & Crossdressers
Caught by my Sister Young man caught in his sister's pantiesin Transgender & Crossdressers
Party Slut Never fall asleep at parties!in Transgender & Crossdressers
More Stories