My First Apartment Chapter 5

I couldn't believe what I was doing! What surprised me even more was the fact that I was enjoying it! Chloe was moaning softly as I kissed and sucked on her beautiful cock. I tried to take a little more each time without choking. I loved the way it felt in my mouth. I loved feeling my lips and tongue moving across her veiny shaft. Every time I looked up at her, she was smiling a loving and grateful smile. It was very encouraging to know I was pleasing her.

Chloe stood me up and knelt down. She started serving me similarly. My mind flew away. I was lost in an ecstasy I'd never experienced before. In all my years of masturbation, I never had a sexual fantasy as erotic as this one. Chloe washed and fingered my hole. She was gentle, her touch was incredible!

I reached below and massaged her pierced nipples. I wanted to show her my appreciation. When Chloe started giving me head. I was already on edge. Moments later I started cumming. I warned her but she let me cum in her mouth. Chloe opened her mouth and showed me my cum. She stood up and kissed me. I was surprised by the gesture. I didn't shy away from her as we kissed.

We towel-dried ourselves, and she led me to her bedroom. I was still in a state of euphoria. I couldn't stop myself. I didn't want to stop. All I wanted to do was please her and learn more about the amazing sex we were having. I love the way she looked at me. She was so beautiful and inviting. I was stone-cold sober, and yet I couldn't think of anything except Chloe.

She positioned me on all fours. I felt fingers and lubricant on my hole. Before I knew what was happening, she was slowly inserting herself into me. I was so turned on I could only moan. My body accepted her in me. There was some pain at first, but the pain was being replaced by pleasure. I accepted my role in our lovemaking as the receiver. I was loving it as she pushed deeper inside me with every new thrust.

I arched my back trying to see her beautiful face. She bent down over me and kissed me. I felt her tongue studs, and it only reinforced my desire as I submitted to her power and beauty. I felt myself building to another orgasm as I felt her swelling inside me. It felt magical as we came within seconds of each other. I collapsed, face-first on the bed. I was exhausted and breathing erratically. I never felt so exhausted and alive at the same time. I was lost in the beauty of the moment.

Chloe pulled me close, she invited me to lay my head on her breast. I lay beside her, cuddling her silky smooth body. She felt warm and inviting. The scent of her body was intoxicating. Chloe didn't say anything. She stroked my face with her index finger and kissed me softly. I scooched up and returned her kiss.

She pulled me closer and smiled.

You were fantastic, Lana!

Really! I was okay? I said.

Yes, Lana! You are a good lover!

I blushed, shifted my head, and lowered my eyes.

Lana! Is something wrong?

No, I turned away a bit more.

Sweetheart, what's going on? Chloe asked with care and concern.

I, I...

It's okay, Lana, you can tell me anything. Chloe said.

Chloe could see my emotional state. She took my hand and stroked my hair. It felt very motherly and loving. I started to calm down a little.

Lana, darling! Was this your first time having sex?

Ye, Yes... I'm sorry! I started to cry.

Ohh! Lana, baby! I had no idea. Come here, sweetheart!

Chloe rolled on her side. She rested my face between her beautiful breasts. I started calming down. She tightened her hug slightly. I felt loved and cared for. I kissed the inside of her cleavage.

Lana!

Yes, Ms Chloe.

Relax, darling, you were great! I love how you took care of me. You are a very passionate lover.

Really! I said softly with surprise.

Yes, Lana! I just hope you enjoyed it as much as I did! Did you enjoy it? Chloe asked.

Yes, I loved it! But why do I feel so ashamed and guilty?

Because you still believe you are a boy. Subconsciously, your feminine side is growing within you. You were raised as a boy, with a loving mother and father. You grew up around a normal lifestyle of a man and a woman.

Now your beliefs are shaken up because you made love in a beautiful and alternative way. While the sex we performed wasn't what you imagined, it was beautiful and very passionate. You feel guilty because it's contrary to what you originally pictured; you loved it. That's why you feel guilty.

You didn't do anything wrong! In fact, you were fantastic! I felt your passion. Did you feel mine?

Yes, I felt it! It was unbelievable! I never imagined sex could be so amazing. I said.

I hope I didn't push you too much. I kinda lost control with you. You're so beautiful and compassionate. It's been a while since I felt such compassion from another person. Chloe said.

I had tears in my eyes. My emotions were everywhere. I hugged Chloe tightly like I used to hug my mother.

I'm sorry, Chloe! I don't know why I'm like this! I mean, you're beautiful, sexy, smart, and very nice. I, I... I always imagined having sex with a girl. Now I don't know what I'm feeling! I loved it. I am so attracted to you, and I'm so very confused. I feel like I did something wrong! I never intended to do any of this. I mean, you're my boss! I just had sex with my boss! What does that say about me?

Lana, it's okay! I didn't hire you to have sex with you! I hired you because I thought you would do a good job! You're doing a good job at work, better than the last five people before you. I gave you a woman's uniform because it's all I had on hand at the moment. Plus, with your measurements, the men's uniform would have been very baggy and heavy.

When I noticed the way you were applying light makeup and the change in the way you were walking, I decided to support you. I thought it was cute. Mrs Wilson thought you were lovely. She doesn't like anyone! I've received several compliments on your work around the complex.

You seem to enjoy the uniform, so I thought I would support your new style. I never intended to be so taken with you. I couldn't help myself. Dana thinks you're adorable! She should know! Dana is just like you! So is Bunny!

Bunny! My stylist? I said in shock.

Yes, Bunny too. Bunny has been on hormones for 18 months now. She told me you were very sexy and cute.

Bunny gave me her phone number! I said.

Maybe you should ask her out for a coffee! Chloe said.

I, I, don't know! She is so beautiful! She could have anyone!

She likes you, Lana! She chose you!

But I'm just a boy in girls' clothes!

No, you're not! You're a very beautiful person! You're Androgynous, Lana. It's not a bad thing to explore your sexuality. Most young people don't have a clue about their own identity until later in life. Most of the ones that do find out later in life end up depressed.

Give yourself a chance. If you want to be feminine, be feminine! If you want to live as Larry, live as Larry. I'll support you! Chloe said.

Chloe?

Yes!

How old are you? I asked.

26, Chloe answered.

You seem so wise and educated, but you look like you are my age.

I was raised by my mother and grandparents. They were teachers. I've read everything from the Bible to War and Peace. I'm finishing up my degree in Pharmacology. I've been managing the complex since I got divorced.

Why did you get divorced? I asked

I got married right out of high school. My wife was a family friend, she was 25. We were happy at first. But the more successful she became, the less she needed me. By our 3rd anniversary, she was going on lots of business trips and working late all the time. She is an investment banker/hedge fund manager.

The more she worked, the more money she made. I was going to college and taking care of the house. Eventually, I started hearing whispers about her infidelity. It broke my heart. I did everything I could think of to show her I loved her. In the end, she left me for another man in her office.

A friend of mine had pictures of her cheating on me. I ended up with a nice alimony check, this house, my car, and her healthcare plan. Not long after, I discovered my feminine side. I've been in transition for almost 5 years now. I'm a lot happier now.

When I saw you that first day with your father, I sensed it. When I saw you at your interview, it only reinforced my initial impression. You started acting a bit more feminine. I could smell and see the tinted moisturizer and the woman's T-shirt. I had a feeling you were like me.

So I took it upon myself to guide you a little bit. I never intended to seduce you. You're very special, Lana.

What will my Dad think? I asked.

If he loves you as much as I suspect, he will support you. He will need time to adjust. Right now, all you have to do is decide what you want! You need to be sure that being feminine is right for you! A lot of boys adopt a feminine style. How feminine you choose to be is entirely up to you.

I'm not sure what I'm feeling right now. I know I love being right here, right now. I kissed the top of her breast. You have beautiful breasts, Chloe.

Thank you, sweetie! If you want your own breasts, I can help! I know a great endocrinologist!

What's an endocrinologist? I asked. I was starting to think about what it would be like to have breasts.

An endocrinologist is a doctor who specializes in hormone therapy. In cases like mine, they prescribe estrogen and testosterone blockers to help me develop physical female characteristics like breasts, hips, ass, feminine facial features, and softer skin.

What does it feel like? I asked, getting more curious and interested all the time.

It's an incredible journey! You're more emotional than ever before. You'll experience hot flashes, cry a lot more. You will find yourself wanting to express yourself with more emotion. Your thoughts and brain become more feminine in your thinking.

It sounds magical! I said.

It can be at times, other times it seems impossible. Living as a transgender woman isn't easy. Not everyone is going to understand or accept you. If you decide to transition you have to understand it's not an easy road.

I started thinking about everything she said. I was also thinking about the past 10 days. I was actually enjoying the clothes, shoes, jewelry and my appearance. I loved my hair. I wasn't sure about hormones, but I did like the thought meeting Bunny for a coffee.

Chloe kissed my cheek and got out of bed. She slid on white satin thong panties and wrapped herself in a white satin robe. She flipped her hair and smiled at me.

Are you hungry? I was going to make a salad.

Yes, please! I said.

Why don't you soak in the hot tub for a few minutes and I'll make us some dinner.

Thanks Chloe!

You're welcome honey!

I soaked in the hot tub naked. I started thinking about everything over and over. I couldn't get stop thinking Bunny. She was my age and very beautiful. She was so forward and so friendly. She could almost read my mind with the way she offered, and explained things.

Chloe made us Chicken Caesar salad. She drank a Chardonnay and I had a bottle of water. We chatted about Dana and Bunny. She showed me a couple of texts Bunny sent her. It appears Bunny wants me to call her. I promised Chloe I would call her.

Chloe took me back to my apartment. I showered and laid out my things for tomorrow. I was thoroughly exhausted from a very long weekend. I was asleep by 8:30 pm.