The Awakening of a Sissy Pt. 10

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Mistress continues the training.
2.2k words
4.54
12.9k
10

Part 10 of the 11 part series

Updated 06/09/2023
Created 12/25/2019
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Best I could tell, neither one of us had moved an inch from the position that we fell asleep in. The urge to pee woke me quite early, like 4 AM early. A smile came to my face as I realized I was still holding Tim's cock. While barely awake, I made my way to the bathroom and took a seat to pee. While sitting there peeing, it hit me that I should probably do a quick freshen up before Tim fucked me in the morning.

After a quick douche, I brushed my hair and my teeth and added a touch of perfume. Walking as carefully as possible, I made my way back to the bed. Moving as cautiously as possible, I made my way back into bed without waking Tim. After successfully re-positioning myself, I again took hold of Tim's cock and soon feel back to sleep.

A few hours later, I began to slowly wake up. To my surprise, Tim's cock began growing in my hand. While Tim was still asleep, his cock was clearly coming to life. It was an amazing site, watching his beautiful cock grow and swell to its full size. Studying it, the veins, his length, and the thickness, I realized that I was truly a cock slut.

Moving carefully, I positioned myself so his cock was now resting right by my lips. After licking my lips, I slowly began running the head of his cock on them. I marveled at the sensual feeling of that smooth velvet head on my lips. This was the cock that hours earlier, had taken my virginity and ejaculated and deposited its warm man seed deep inside me. Yes, the same cock that had brought me so many intense pleasures throughout my body, while making me a complete sissy.

My thoughts were interrupted when Tim asked "are you enjoying rubbing my cock on your lips as much as I'm enjoying it Jolie?"

Smiling and with not a moments thought, I responded saying, "I am but, I'd enjoy your cock more if it was fucking me right now."

"Looking at that sweet ass of yours, that is exactly what I plan on doing Jolie. I want you to get your sissy ass, face down, ass up, and legs spread wide. Reach back and open those sweet cheeks, so I can see that pussy of yours."

There was no need to tell me twice. That was music to my ears. Quickly, I moved around on the bed, positioning myself as Tim directed. Tim grabbed the lube and pushed some into my eager hole with his finger. As he fingered me he started to laugh. "It seems your pussy has tighten up a little since last night. Don't worry Jolie, I'll be opening that thing right up in just a moment. Now tell me exactly what sissy wants this morning."

"This sissy needs your beautiful cock. I want you to fuck me and open my pussy. I want your cock in me and I want you to fill me with your morning load of man seed Tim."

Moments later, Tim was behind me, rubbing his cock on my waiting hole. It took a few tries before my hole opened up, and welcomed the head of Tim's cock inside. Tim gave me a few seconds to adjust before pressing more of his cock into my pussy. Once 3-4" were inside he slowly began fucking me.

It took no time at all, for my pussy to relax and welcome the rock hard invader. I lifted my head and looked back at Tim. As the strokes went deeper inside me, I began moaning in pleasure, while pushing back to meet each thrust of his cock. "let go of your cheeks, but your arms out, and get that face down on the bed bitch."

As he said it, he began smacking my ass. In a rather loud voice Tim said, "Fuck yourself on my cock bitch. Show me what a nasty sissy cock slut you have become. Smack, Smack, Smack.

"That's it Jolie, take my cock up your ass like a good little sissy faggot. Ride my dick you fucking slut." Smack, Smack, Smack.

Tim's words and actions encouraged me to ride him hard. I felt the warm redness on my ass cheeks which added to my lustful need. I was breathing heavy and moaning in pleasure as I continued fucking myself on his cock. Tim grabbed my hips and slammed his cock into me.

I let out a loud grunt as he slammed his cock into me. He began pumping into me harder, while occasionally smacking my ass cheeks. My heightened state of lust kicked in and the words began pouring out of my mouth as my clitty began to leak. "Yes Tim, fuck me. Slam me with your big dick. Use me like the cock slut I am. Fuck me and stretch my hole."

Tim continued his assault on my hole. Occasionally, he'd pull his cock all the way out of me before slamming it right back in. The name calling and slapping of my ass also continued as I begged for him to fuck me harder. He was fucking me so hard the headboard was banging on the wall. This went on for another 10-15 minutes before Tim let out a loud grunt and exploded deep inside me.

I felt shot after shot, as he emptied his balls inside me. this also caused my locked up clitty to again leak a stream of fluid. When Tim was done filling me, he collapsed his body on top of me, while leaving his cock inside me. We were both breathing hard and totally sweaty. Neither of us said a word for a good 5-7 minutes, while we regained our composure.

Tim withdrew his cock and rolled off of me. "Fuck, that was amazing Jolie. I don't think I have ever cum that hard in my life. When word gets out about what a great fuck slut you are, you are going to become a very wanted bitch. How do you feel?"

I rolled on my side so I could face him. Smiling at him, I said, "how do I feel? I feel like a well fucked sissy slut. I'm full of your cum. My ass cheeks are quite warm. I can feel the cool air on my gaped hole and I am a sweaty mess. What a way to start the day, and look, it's just a little after 8 AM."

A few minutes later I made my way to the bathroom and took a seat on the toilet. I sat there letting Tim's sperm drip out of me. When I was done, I gave myself a through douching before starting the shower. Seconds after entering the shower, Tim stepped in to join me. He pulled me to him and held me close as he whispered in my ear "I'll fuck you any time you want."

We stayed there pressed together for several minutes while enjoying the warm spray of water washing over us. Tim spun me around grabbed the shampoo and began washing my hair. When he was done, he took the soap and started washing my back, shoulders, and legs. After spinning me around, he gently washed my front side. When he was done, he stepped back and let me rinse off.

I spun him around and washed his backside. Spinning him around, I slowly began washing his shoulders and chest. With that completed, I slowly and softly, began to wash his crotch. Once again, his cock started coming back to life in my hands. helping him along, I slowly started stroking him. Stepping slightly to his side, I let the water rinse him off before dropping to my knees and sucking him off. Swallowing his load, I smiled and told him that was for the great fuck this morning.

After Tim left the shower, I went about the task of conditioning my hair, while enjoying the taste of Tim's seed in my mouth. Once I was done, I stepped out of the shower and wrapped my hair in a towel like Mistress had taught me. I dried off and rubbed on my scented body oil. Before heading back into the bedroom I took my hormone medication.

I had barely been sitting on the bed for a minute when Mistress Di came into the bedroom smiling. "Well my little cock slut, you seem to have gotten an early start to your morning. You didn't think all the noise wasn't going to wake me, did you? The damn headboard slamming into the wall. Bam, Bam, Bam. You screaming out fuck me harder Tim, stretch my hole Tim and all that. Yes, I heard it all, and was quite impressed with the sissy slut I have created Jolie. Get you robe and your slippers and meet me in the kitchen sissy."

When I walked into the kitchen, Mistress was just putting her phone on the counter. "Great news Jolie, I just got off the phone with Nikki and she wants us to stop over. She said she has made some great progress on the remodel and wants us to see how it is coming along. While it is not move in ready just yet, you should get a good sense of how your new sissy house will look. When it is finally ready, I'll pull together a very special sissy house warming party for you. Now please tell me that your pussy has not been wrecked for the day."

We spend the next 45 or so minutes in casual chat, while sipping on coffee and eating some eggs. She was curious to hear about my night and morning of sex with Tim. It was very clear that she enjoyed hearing how my clitty leaked while Tim was fucking me. After, she led me to the powder room and styled my hair. Then she spent more time sharing makeup tips with me. I was then handed a bag and learned that Mistress had picked out the items for me.

Once I was dressed in my new clothes, I walked over to the full length mirror to check myself out. What reflected back at me was Jolie, a well made up sissy. Joe was removed and in his place stood a sissy wearing red stretch jeans, red 5" come fuck me heels, a white blouse, with red bra showing clearly thru the thin white material of my blouse. I looked myself over from every angle. My ass looked great in those jeans. It's teardrop shape seemed to proudly stand out.

"You look great Jolie, go get your purse, we need to check out Nikki's work. After that we are heading to Helen's so you can meet up with Roy and Ronald. They are so looking forward to blacking you for real."

I grabbed my purse and we were out the door. During the short drive over to my place, all I could think about was Roy and Ronald. Their beautiful Black Cocks were most certainly going to be invading both of my holes. I was not certain I was ready for that. And yet, I was excited by the idea.

As we approached my house, the first thing I noticed was that there was a new and much larger picture window in my living room. On the wall opposite the picture window, there was a very large picture which was clearly visible to anyone who might approach. The picture was a naked black man, well built and very well hung. My once white walls was now a blend of soft rose and pink.

Walking up to my front door, I saw that my once gold knocker was replace by a large black spade knocker. Nikki greeted us as we walked inside and showed us around. She was quite proud of her work and how effeminate the place was looking The once white hallway was now coral pink.

The master bedroom was a very soft pink color. On one wall there was yet another large picture of a well built and very well hung naked black man. Hanging on another wall, was a captioned picture of me, naked in come fuck me heels and locked in chastity. The wording read - THERE IS NOTHING BETTER THEN SERVICING A REAL MAN AND HIS BEAUTIFUL BIG FAT COCK!

The master bath was completely redone. The tile floor was now a mix of pink and rose. My once blue sink and toilet were a very bright pink, along with a new and larger thermal tub. The walk-in shower was now much larger and redone in a soft coral pink. In one corner there was a built in douching station set up for my use, before showering.

When the tour was done we sat in the kitchen and drank coffee while Nikki talked about her further plans for the place. Mistress Di seemed quite pleased with the way things were progressing. She complimented her on the work.

When Mistress Di told Nikki that we were needing to leave to meet up with Roy and Ronald, Nikki insisted that she get plenty of pictures. She was certain some pictures would add to the ones currently hanging. Nikki gave each of us a hug before we departed for our drive to see Mistress Helen and the others.

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AnonymousAnonymousover 3 years ago
Transformed

My sissification started after i met a cross dresser in a club who said he could help transform me in to a full on sissy.I went and met his wife who has turned him into a sissy dresser.She controls every thing when it comes to his cross dressing.I have been with them for a year now.She has transformed my body to a female one.Small waist wide hips hairless body female breast 38d long hair.She likes me in full body stockings and 6'' high ballet boots.Now they both will have sex with me.Bound and with hands and ankles cuffed and a ring gag in my mouth they started.I was sucking his cock she fucking me with a 12'' horse cock strap on She had invited some friends over to brake me in.Soon i was swallowing loads of cum and cum running out of my ass.She loved to eat out my ass an suck the cum out.They finished by shooting cum all over my body.Their finial act was to piss on and in my mouth and ass..

alnycalnycalmost 4 years ago
Great

Fabulous story can’t wait for more. I’m get so excited reading this and identify with Jolie. Keep the story going PLEASE

Alan

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