The Awakening of a Sissy Pt. 08

It was only a matter of minutes before Mistress pulled the car into a long driveway. My mind was still processing the idea that I was now on hormones. Once we were parked, Mistress had me grab my bag and follower her on the path to the house. She clearly knew this pace well, as she walked right into the house, with me following closely behind. As soon as we walked in I heard the sound of someone clearly getting spanked.

Walking into the living room, the first thing I saw was to well build and well hung naked black men standing there. They were having quite the laugh. On the sofa, was a naked woman, with someone else who was naked in just pink heels, over her knees getting spanked.

The woman looked over at Mistress Di and smiled. "Hi Di, nice to see you made it here. Don't mine me, I am spanking this sissy husband of mine, because he raked his teeth on Roy's cock while he was fluffing him." As she spoke, she continued spanking her husband. His bottom was a bright red and he was crying, while telling his Mistress how sorry he was.

Mistress Di looked over at me with her wicked smile. "You better behave or you will be next Jolie. She point to a door and said, "go in the bathroom and get undressed and put on you pink come fuck me heels and get back over here. She added, "hang your dress on the door and leave your bra and panties on the table in the bathroom. You will not be needing them for some time. Don't forget to touch-up your lipstick."

Doing as I was told, I went into the bathroom, removed my cloths, and put on my heels. As I touched up my lipstick, I wondered what Mistress had in mind for me. All the while I heard the spanking continue.

When I returned to the living room, Mistress was naked, in just heels, and standing between the 2 naked men. They were both rubbing their hands on her body. She had a hand on each of their cocks and slowly stroking them. Mistress introduced me to the 2 black men.

"This man over here is Roy, and over here is Ronald. Guy's, this is sissy Jolie. Jolie, you will refer to them as Master. Over there is Helen, you will refer to her as Mistress. Over her knees is sissy Brianna."

When Mistress Helen was done spanking sissy Brianna she had him stand up and apologize to Master Roy for raking him with his teeth. Brianna was about the same height as me as me, but more slender. She was also locked in chastity but his cage was semi clear pink. I immediately noticed her sissy tan lines. Brianna was clearly on hormones that had already produced budding nipples and a slight shape of breast.

Mistress Helen then directed Brianna to get back over her knees. Once he was in position, Mistress Helen told me to come and stand in front of her and "spread his sissy ass cheeks wide open. Roy, come over here and fuck my sissy husband up his sissy ass. Ronald, come over here and fuck him in his mouth."

The 2 men wasted no time taking their place at each end of Brianna. Master Ronald held Brianna's head as he pushed his cock into Brianna's mouth and began fucking her. Master Roy showed no mercy as he forced his cock into Brianna's ass and started hammering away. As they went about punishing Brianna, I was made to stay there holding his cheeks wide open. I could hear muffled whines from Brianna as Master Roy pounded away at her bottom. There was something very erotic about watching the whole scene.

Mistress Di started telling everyone about how I had spent the night with Tim and what we had done. She also told them all about my doctors visit. Mistress Helen spoke about how much she loved humiliating her sissy husband as well as other sissies. Looking at me, Mistress Helen said, "I'm going to love being a part of your training Jolie." I wondered to myself, how long will it be before I'm getting fucked at both ends.

When Master Ronald made it known that he was about to cum, Mistress Helen directed Brianna to hold the cum in her mouth and not swallow. After Master Ronald filled Brianna's mouth with cum, Mistress Helen directed me to go kiss Brianna and sample his cum. I looked over at Mistress Di who simply said, "do as you are told sissy Jolie."

I went over and knelled by Brianna, and began kissing her. Brianna wasted no time pushing cum into my mouth. As we kissed Master Roy continued fucking Brianna. While Brianna and I kissed, Master Ronald walked over to me. He held out his black cock and said, "suck it clean sissy Jolie. He pulled my head to his cock and pushed it into my mouth. "Suck it, you sissy faggot, don't use any hands. Clean my black cock and balls like a good little white boi sissy bitch."

I could not believe the power this man seemed to have over me. I took his huge black cock in my mouth and went about the job of cleaning it. I felt very aroused knowing I was sucking a black mans cock. "White sissy boi's like you need to learn to respect the power of black cock, you sissy faggot. Lick my balls, bitch. You're going to clean Roy's cock too, once he finished fucking sissy Brianna.

As I was sucking and cleaning Master Ronald, Mistress Helen told Mistress Di that she wanted to see me eat Brianna's cum filled pussy after Roy is done fucking it. Mistress Di laughed and told her, "that is a wonderful idea Helen. Sissy Jolie needs to realize the role and duties of a true cum slut sissy faggot."

To say I was shocked to hear what they had in mind for me would be an understatement. Was Mistress Di serious, was I going to have to eat Brianna's cum filled pussy. The simple idea for it made me feel so humiliated and yet somehow excited.

Brianna was now moaning and whimpering in pleasure. "Yes Roy, yes, fuck my sissy pussy with your big black cock. Fuck me good, and fill my pussy with your black man seed. I love feeling your big black cock up my ass," Brianna screamed.

While still cleaning Master Roland's cock, I heard Master Roy let out a loud grunt. There was no question that he was black seeding Brianna's pussy. After he was done black seeding Brianna, I was made to crawl over and clean his cock. I felt totally ashamed knowing that I was taking his cock in my mouth after fucking Brianna. There was a different taste to him, I knew it was a mix of his cum and Brianna's pussy.

It was not long before Mistress Di was holding me by my hair and having me crawl over to Brianna's gaping pussy. Some of Master Roy's cum was already leaking out as Mistress pushed my face in. As I began licking up the mess the Men and Women were laughing and making fun of me. Mistress Di made sure I got my tongue deep into Brianna's gaping hole. While I felt totally humiliated, there was something very erotic about licking Brianna's gaping hole and lapping up Master Roy's black man cum. I believe it was the knowledge that Roy's cock had just been in there, filling it with his black seed. Once I was done, I was made to kiss Brianna, so she could have a taste of herself.

Mistress Helen then directed me to sit on the edge of the coffee table. "Spread your legs wide open sissy Jolie and lay back on the table. Brianna, get down on your knees, between Jolie's legs, and eat her pussy, Mistress Helen directed. Brianna wasted no time kneeling and burying her tongue in my pussy. In no time at all, I was moaning and whimpering in pleasure.

While enjoying the feel of her tongue in me, I saw Mistress Di and Helen embracing one another, in the middle of a deep passionate kiss. They were running their hands over each others bodies while Master Roy and Ronald stood by watching. I found it quiet stimulating.

Around 15 minutes later, we were told to go to Brianna's bedroom, to put on our bathing suits, and work on our sissy tan lines. Brianna, held out her hand and helped my off the coffee table. She continued to hold my hand as I walked to the bathroom to grab my things.

Once I had grabbed my things, Brianna again took my hand and led me to her bedroom. As we walked off, we were told to use sun lotion and turn every 20 minutes. Master Roy told us to be prepared to lick clean the pussy' and asses of our Mistresses later on. Brianna giggled upon hearing that.

Brianna's bedroom was clearly very feminine. It was full of pink and white lace. She locked the door once we were inside. She then promptly pulled me to her and kissed me deep. While I surprised by her action, I found it rather pleasurable. We continued kissing fro awhile before Brianna stepped back.

"I'm so glad we finally got to meet. I've seen some of the video's that Mistress Di shared with my Mistress. The one of you sucking Tim's cock for the very first time was really hot. I could see you really got into it Jolie. My very first time was with an old boyfriend of my Mistress wife. She made me suck Reggie's black cock to show that I accepted the fact that I was a failure as a man. That same day she took me to get this spade tattoo on my ankle. Maybe you will get one also one of these days."

As Brianna spoke, I could not help looking at her body. She was so effeminate in every way. I really admired her, the way her breasts were developing and wanted the same for me. She noticed me looking at them and told me I could touch them, which I happily did. I was amazed at the puffiness of her nipples.

While putting on our skimpy little bikinis, Brianna told me how they had slowly developed. I learned that she had been a sissy cuckold to his wife from before they were ever married. She told me that it was her idea to start on the hormones and his wife fully agreed.

Out on the deck, while working on out tan lines, Bri, as she asked me to call her, and I had a wonderful time chatting all things sissy. I found out that she had also been with Tim. Not only did she suck him but that he and also fucked her a few times. I told Bri that Mistress Di had informed me that Tim would be the first one to fuck me and how I was so hoping it would happen soon. That led to a sexy discussion about cocks, cum, and sex. My desire to experience it grew stronger. We also chatted about hormones and the changes I would experience from them.

Our conversation was broken by the intercom. "Your services are needed in the master bedroom. We need you to clean the men's cocks and then our pussy's. You will then fluff the men and get them ready to fuck us in our ass. Leave your bathing suits in sissy Brianna's room and get your sissy asses in here now," Mistress Helen stated.

We quickly put our heels back on and headed toward her bedroom while we removed our suits. As we tossed our suits on the bed, Bri, with a big smile on her face said, "hurry up Jolie, time for us to enjoy some flavored black dick and cum filled pussy!" As soon as we entered the master bedroom, we were ordered to our knees.

Master Roy walked up to me saying, "open your sissy mouth and get cleaning my cock bitch." Without any hesitation, I took his cock in my mouth. As I sucked and licked him clean I saw Bri doing the same for Ronald. "That's it, suck my cock you sissy bitch. White sissy boi's like you are meant to serve black cock. I can't wait to fuck that white sissy ass of yours. You will be begging me to use my black cock to fuck you up your ass bitch. You will know what it means to be blacked," Master Roy stated.

True to their words we were made to clean the cum from the women's pussy and ass. Before getting dressed and departing, Mistress Di had me suck off both Roy and Ronald. She wanted to ensure I had plenty of black seed in my belly.

As we drove away, Mistress was smiling and laughing. "So Jolie, what did you think of those black cocks of theirs, be honest with me."

I looked over, as I blushed and giggled. "Oh my, they were so big and thick. They are so intimidating and yet so manly and sexy looking. I can't believe how much cum their big balls were able to produce. Does Roy really want to fuck me with that big cock of his? I'm not sure I'd be able to handle that big thing inside me. Am I going to end up getting a spade tattoo like Brianna's?"

Mistress, while smiling, patted my leg and told me how proud she was of me. "Yes Jolie, both Roy and Ronald told me that they want to hit that cute white ass of yours. Something tells me you want that as well. I saw the look on your face as the 2 of them were using Brianna. You couldn't take your eyes off Roy's cock as he fucked her. I know that there will be other black men that will want your white pussy too. Black men love white effeminate sissy boi's like you. They love conquering and dominating sissy white boi's and putting them in their place. I think you have the makings of a wonderful black cock slut. As for the spade tattoo, lets discuss it after you have done your first black gang bang."