The Awakening of a Sissy Pt. 07

I was a giddy as a school girl knowing that I would be sleeping with Tim, Curiosity was building inside me. I was going to sleep with a man for the very first time. What was the special surprise that Tim had planned for me.

All night long, as we watched sissy porn, Mistress kept harassing my pussy with various levels of my trainer. I was happily enjoying using my mouth to pleasure Tim. I was amazed at his seemingly endless supply of cum.

Around 8:30 she led me to the spare bedroom where Tim and I would be sleeping. She leaned in and casually whispered in my ear, that Tim had made her promise to let him be the first one to fuck me. Right after that, Mistress casually told me to go about and take care of my normal evening preparations.

"Make sure you douche extra well. I'll put your trainer on the charger, you will not need it tonight. After your bubble bath, dry off and put on your body lotion. Don't bother with lube this evening, you won't need it. After you are done, put on your lipstick, and slip on your just your robe. Tim will want you totally nude and vulnerable for the evening."

While soaking in my bubble bath my mind raced. What did Tim have in store for me? Why did he want me totally nude? Was he planning on fucking me, would I be able to handle his big cock? Was I ready for that, how would it fee, would it hurt?

Once I was fully prepared, I made my way back to the living room. Tim was still naked and watching more sissy porn. Mistress was now wearing a long black silk nightie. She again had her wicked smile on her face. "Oh look Tim, your sissy slut is ready and waiting for you. You 2 have a fun night. I want full details in the morning Jolie."

Tim stood up and put an arm around my waist, and kissed me on my cheek. "Let's go to the bedroom Jolie, I'm so looking forward to having some alone time with you." With his arm around me, he led me to the bedroom. Once inside, he closed the door and led me towards the bed.

He stood in front of me, looking me up and down. "You truly are a remarkable submissive sissy Jolie. I am so looking forward to getting to know you better. I want to get to know every inch of that body of yours and help bring it to life. I so want to experience your passion and lust. There is a true slut in there and I want to help bring it out of you."

As he spoke, he moved in closer to me and untied my robe. He slowly opened it and looked me over before sliding the robe completely off of me. Once I was naked, he moved in closer and placed his hands on my waist. I was pulled in toward him, our bodies pressed together. I felt the warmth of his skin against mine, and it sent tingles throughout my body. With that done, he he leaned in and kissed me firmly on my lips.

Joe would never have been in a situation like this. Jolie however, was a totally different story. While a little surprised, and feeling rather vulnerable being totally naked, I welcomed his kiss, finding it quite enjoyable. We began making out, our tongues danced together. Tim's hands wondered all over my body.

The kissing got more and more passionate, my heart rate increased, and I was breathing faster. My hand began rubbing all over his body. Using one of his hands on my bottom, Tim had me raised so I was on my tip toes. His other hand began moving around my chest. It was as if he was searching for my breast.

His fingers found my nipple and softly began teasing it. This sent a whole new level of tingles racing thru my body. Never in my imagination would I have thought a mans touch could do this to me. These new sensations were pushing Joe further away. Jolie was coming stronger to the forefront of my mind.

While I did feel vulnerable without a single piece of feminine clothing on, I was not feeling shame. Somehow I was delighting myself in being so exposed to Tim. It felt right, so feminine, exposing myself to him as the effeminate sissy I was. His hands on my body felt incredible.

Tim pushed me backward until I fell on the bed, He continued kissing me, while pushing me further on the bed. He began kissing my neck and ears. At times his tongue would tease my ear. My emotions and passion continued building. Soft moans and whimpers were slipping out of my mouth. Tim's hand was rubbing my chest and playing with my nipple.

He continued his kissing, working his way down to my chest. Soon his mouth found its way to my nipple. At first he just teased it with his tongue, running it in circles around my nipple, which was now at full attention. Next he wrapped his mouth on it and began softly sucking on it. More wonderful tingles and sensations again raced throughout my body. The effeminate in me was coming to life and blossoming at a greater rate then I could ever have ever imagined.

"Oh my god Tim, that feels so good," I involuntarily exclaimed. As if natural, my hand went to his head, pressing it to my breast. Simultaneously, without a thought, I ached my chest to him. I was seemingly and naturally, offering more of my tiny breast to his mouth.

As he laid on top of me, I felt his cock growing. I worked my hand between us and softly began stroking it. Tim's mouth continued sucking on my nipple. His tongue was now flicking at the tip of it, bringing about even more new sensations. Tim's hand played with the other nipple until his mouth shifted to it.

After a while he moved back up and was again kissing me on my lips. As we kissed, I felt him shifting his hips around. My hand was still on his cock, when I suddenly realized, I had opened my legs and wrapped them around him. My ankles locked together, as I was unknowingly, pulling him closer to me.

We continued our kissing and touching for several minutes, my emotions were running in high speed. Tim rolled us on our sides. His hand worked it's way toward my bottom. His finger began tracing the line between my cheeks. It didn't take long for his finger to find its way to my pussy. The warm touch of his finger on my rose felt wonderful. I kissed him deeply while slightly pressing myself to his finger.

In shock, Tim suddenly stopped kissing me and touching my pussy. "I want you to turn around Jolie. Climb on top of me, spread you legs open, so your pussy is facing me, in a 69 position. I want to see you as the naked sissy bitchboi you are. That way, you can enjoy my cock, while I get to know your pussy better."

I was more than happy and ready to take Tim's cock back in my mouth. As I shifted around, I giggled and said "like this Tim?" I knew what 69 was however, I had never done it before. We both shifted around a bit until I was in the proper position. I could feel the warmth of Tim's breath on my bottom. I wondered what Tim had in mind for us.

Wasting no time, I slowly began giving Tim's cock my undivided attention. As I began working my mouth on him, I felt his warm wet finger again softly teasing my pussy flower. With my effeminate emotions running at the rate they were, I pressed my rose to him. I was both willingly and wantonly offering it to him. I knew there were more pleasures to yet to experience.

He finger traced me as a pressed to him. Soon my pussy opened and welcome him inside. I immediately noticed the warmth as it slowly slid into me. There was a sense of pride in my mind, knowing I was letting a man finger me. I was Tim's sissy bitchboi. Somehow it seemed so right, perhaps fitting. A soft moan of pleasure slipped out of me just as it happened.

Tim's finger moved both in and out of me as well as twisting inside. More moans of pleasure came out of me. With Tim's cock in my mouth and finger in my pussy, I felt content. My hips were naturally moving in response to his finger. Soon a second finger was making it way in. As he worked them in and out he was also using them to expand me wider. This was so different then my trainer, it was a man doing this to me.

After some time, to my disappointment, he stopped and removed his fingers. I don't know if it was the effeminate in me, the slut, or the passion and lust but I quickly stated "don't stop Tim, it feels so good." I really want your fingers back in me, please?"

"Relax Jolie, I think you will like what I have in mind," he stated. I felt his hands spreading my cheeks open wide. His lips made contact with my flower as he softly began kissing it. Tingles raced thru my pussy and body. After some kissing, his tongue began tracing all around my flower. All new sensations again came to life within me. I was softly moaning and whimpering in pleasure. His tongue felt delightful. The effeminate that was once buried within me was growing stronger.

My hips were rolling around as his tongue danced circles along my pussy. Suddenly, to my delight, his tongue pressed to my flower and slightly slid into my pussy. I was shocked at how good it felt. "Oh Tim, that feels wonderful," I exclaimed. His warm wet tongue slid in a little deeper. My pussy was alive with so many new and exhilarating feelings.

As if it was totally natural, I was pushing my pussy to him. I wanted his tongue in me even deeper. While my body and mind dealt with all these new sensations, I did my best to give his beautiful cock the attention it deserved, While Tim was tongue fucking my pussy, his hips began pumping his cock into my mouth. In hope of getting, and wanting his tongue deeper in me, I spread my legs wider, as I pressed my bottom to his mouth.

There was no hiding the pleasure I was experiencing. My hips were rocking as Tim was tongue fucking my pussy. His cock was buried in my mouth, while I mumbled words of pleasure, passion, and lust. "Your pussy tastes so good Jolie, I so wish I could fuck you right now. I'm going to so enjoy taking your sissy cherry one day. You're going to be molded into the proper little sissy bitch that you were meant to be."

Letting Tim's cock slip from my mouth I responded telling him, "ohhh Tim, your tongue feels so good. My body is alive, fuck me with your tongue. I can't wait for you to fuck me. I want you to take my cherry and make me a sissy bitch. I want your tongue deeper in me."

As i spoke, I never stopped stroking his cock. I was right back on it, the moment I finished responding. In my hunger for his cock, I took in in deeper then ever before. I felt his cock begin to slip into my throat. As I held it there, proud of what I managed to accomplish, his cock erupted. He started shooting his cum directly down my throat.

I backed off and happily accepted the remaining blasts in my mouth. My hips were rocking. almost uncontrollably. Tim's cock remained in my mouth for several moments, as I enjoyed the tongue fucking I was receiving.

Tim used his tongue on me for several more minutes. When he was done he told me to slip on my nightie and hand him my trainer. Without question, I did as I was told. Once the trainer was in place Tim had me join him on the bed.

I laid on the bed, my head on Tim's chest, and his soft cock in my hand. The last words I remember hearing before falling asleep were Tim telling me that as soon as I woke up I was to remove my nightie and suck his cock. "From now on, that is your morning duty, whenever you sleep with a man."

I woke to my trainer going off in my pussy. I still had Tim's cock in my hand however, it was now rock hard. As instructed, I removed my nightie and took Tim into my mouth. I loved the feel of his hard, warm wood, as it slipped between my lips. I fully embraced the fact that I had a mans cock in my mouth. Clearly this is what I was meant for.

As Tim woke, he began softly moaning in pleasure. His hand pressed on my head, encouraging me to take him deeper. "That's it sissy, suck my cock like a good little slut. Get it all in your mouth, just like you did last night. We both know you love cock, Jolie, you're a sissy faggot now. Accept it slut."

Tim's words made me smile as I sucked his cock. He was right, I was a sissy faggot now. Jolie fully embraced those words with pride. As I sucked his cock, my trainer was swelling and thumping in my pussy.

"Be a good little sissy faggot, get all of my cock in your mouth faggot," Tim said as he pushed my head down on him. "That's it Jolie, deepthroat my cock like a good hungry cock slut should. We both know you love having a mans cock in that sweet faggot mouth. Get it all in there again slut. That's it Jolie, all the way down. Keep doing that, I'm going to cum."

My head repeatedly slid down, taking every inch of Tim's manhood. His morning wood exploded, sending the initial blasts directly down my throat. I back off just enough to get the remaining shots in my mouth. He filled my mouth with a pool of cum. After a few seconds, I swallowed it down, and went to work cleaning his cock.

Once he was properly cleaned, I moved up and rested my head by Tim's. "I hope you found your morning wake-up to your satisfaction," I whispered in his ear. "What a nice way to start the morning. A nice hard cock in my mouth and the taste of your cum."

We had been laying there for several minutes when Mistress walked in. "Time get up Jolie, we have a busy day ahead of us. Put on your robe and heels and meet me in the kitchen."

"I'll see you later today Jolie, have a great day. I look forward to having you in bed with me again," Tim told me.

Once in the kitchen, Mistress asked me about my night with Tim. Taking time and using my best effeminate voice, I slowly explained my nights experiences. I also told her about what I had done this morning. She seemed quite pleased with how my body had reacted to Tim's tongue.

"I knew from your performance yesterday, that you were well on your way to becoming a true submissive sissy cock slut. We will be working on more of that today, as well as other things. Finish your coffee and go about your morning preparations. Once you are dried of and oiled, I want you to give Tim another blowjob. After that, I'll be waiting for you in the living room, with your first outfit for the day. Bring your plug with you, we will need it later on."

"I spoke with Nikki and she said that the remodeling is coming along fine. She wants me to keep you away for a few more days while she is doing the bulk of the work. That means you will be spending at least a few more nights with Tim. Somehow, I am certain you will like that. I also spoke with my doctor friend and we will be meeting with her today. There will also be a few special surprises for you during the day."

As I went about my morning, my mind raced with thoughts of what the day might bring. What did Mistress mean by my first outfit of the day. Once my body was oiled, I applied some of my cocksucker red lipstick. I walked totally naked, back into the bedroom. Tim was on the bed still naked. I climbed between his legs and promptly sucked him off. As I left the bedroom, I looked back at Tim, a big smile on my face, and told him how I was looking forward to seeing him again tonight.

Mistress was waiting for me in the living room. On the sofa I saw red lace panties with matching bra. There was also a pink and red flowery sun dress and pink sandals. Mistress had me don the bra and panties and began working on my makeup and hair. My toes and fingernails were painted a very bright pink. With a laugh she said, "from the smell of cum on your breath, I'm sure you wouldn't mind spending some additional nights in bed with Tim, will you Jolie?"

I looked at her and smiled, telling her how much I would enjoy more nights with Tim. Mistress laughed again and said I was really becoming a hot little sissy cock slut. She also informed me that we would be seeing her doctor friend for our first stop.

As we prepared to head out the door, Mistress handed me a pink gym bag. "This has all the things you will need for today's adventures Jolie. I took the bag and my purse and we were out the door.

Once we were on the road, the conversation turned back to the doctors visit and hormone prescriptions. "I know you will love the changes that your body will go thru as the hormones begin altering your body. Your skin will get softer and more feminine looking. Little by little your chest will begin to develop breasts. Your nipples will start to grow and become more sensitive. Your body will start to slowly produce less and less of that unneeded testosterone. Gradually, your clitty and jewels will begin to shrink. We both know they are useless anyway. I'm guessing your already cute bottom will become even more shapely."

My mind began to wonder, thinking of thoughts of the changes my body would experience and what I might look like growing breasts. I wondered how they would feel being sucked on. Then me mind went back to Tim and his tongue. I so wanted to experience more of that feeling. I then thought about Tim's beautiful cock and how it would be the first to actually fuck me. Maybe it would happen tonight, I thought and hoped to myself.

About 30 minutes later we pulled up to a small brick professional building. There were signs for lawyers, doctors, and various management services. Mistress led me into the building and directly to the doctors office. When we entered there were other patients in the waiting room. Mistress pointed to a sofa and directed me to take a seat. She walked up to the receptionist and spoke with her for a few moments. When she returned she had a clipboard with some forms I had to fill out.

The initial challenge came with my name. Mistress told me to mark it down as Jolie Meadows, my new sissy name with actual last name. The first forms were basic medical questions about my health, previous illness' and weight gain and loss. There were also questions about any allergies.

The final forms were more of a personal nature. My childhood development, years of sexual confusion, my sexuality, sexual activity, gender identification... Mistress helped me craft the appropriate responses, which made me blush. While much of it was true, I was now putting it on paper for others to read.

By the time we were done with with the forms, we were the only ones in the waiting room. Mistress and I were casually chatting about the forms when the receptionist walked over. She had a smile on her face as she looked at me. "Please follow me and I'll lead you to the exam room. The doctor will be with you shortly." As I followed her, I quickly remember my cum breath, pulled out my breath spray from my purse and freshened my breath.

In the room, she handed me one of those exam robes. Guiding me to a changing area, she said, "you will need to undress, removing all of your closes, and put this on for your examination." Looking at me with a smile she added, "don't worry, we have seen it all before. There is nothing to worry about in this office."

I expected the nurse to leave me alone as I undressed but she just stood there. While I removed my sandals and slipped out of my dress, I dawned on me, I was in my chastity cage. A bit of panic momentarily came over me before I figured out how I would handle the situation. I removed my bra and took the robe. Once it was on and tied, I removed my panties. My problem solved for now, but there would still be the doctor.

As I was led to the exam table, Mistress must have noticed the concerned look on my face. "Don't worry Jolie, you are safe here, they are very professional. You can relax, you are in good hands, I've worked with them before."

As Mistress spoke, the nurse left to room but not before looking back and smiling at me. Mistress walked over to me, placed her hands on my legs. "I'm sure you are a little nervous. Remember, I'm right here with you as you take this very important step. In time, the hormones will help you become so much more feminine feeling and appearing. They will help bring out your already natural sissyness. You already make a lovely effeminate when you are dressed. Trust me, you know you need this" she said as she softly kissed me on my cheek.