The Awakening of a Sissy Pt. 09

Mistress Di pulled her car into her garage and instructed me that I was to immediately go prepare myself for the evening. "Remember to douche extra well for your evening time with Tim," she added. "Who knows what Tim might have planned for you tonight Jolie." She said that while winking at me.

My mind was full of thoughts as I made my way to the bedroom. Was Mistress giving me a heads up about possibly getting fucked by Tim tonight? Was Mistress Di going to be present if and when it happened? Was it going to happen in the bedroom?

I removed all of my clothes and made my way into the bathroom to begin my evening routine. On the sink was a bag with my name on it. Inside I found my new hormone medications, which I promptly took. As the bathtub filled with my bubble bath, I took time to ensure I was properly douched.

I eased myself into the tub, and went about the task of shaving myself smooth all over. By now, it was second nature to me. Once done, I laid back and relaxed, while my mind reviewed the days events.

A warm and relaxing feeling came over me at the realization that I was now on hormones. I let my mind drift to the 2 men, and those beautiful black cocks, that I had happily taken in my mouth. My next thoughts were that of Tim. Would tonight be the night that he would take my cherry? How would it feel, could I handle it? I knew I wanted it to happen.

Possibly 20-25 minutes later, I climbed out of the tub. After carefully drying myself, I applied my body lotion. I loved the way it made me feel so smooth and smell so feminine.

I took some time to look, perhaps admire my body, in the full length mirror. The tan lines clearly stood out and screamed sissy. My belly button piercing only added to the image. I tried to imaging myself with small budding breasts, like what Bri has. Looking at my butt, I wondered how it might fill out more from the hormones.

After some time, I put on my heels and robe. After some makeup and lipstick, I was ready to make my way to the living room. I was in a rather excited state of mind over what I hoped might happen. When I got to the living room I was a little disappointed to find only Mistress Di sitting on the sofa.

She must have seen the disappointed look on my face. "Don't worry Jolie, Tim will be here shortly. He's outside taking care of the Hot Tub on my deck," she stated. "Why don't you take off your robe, and place it on the chair over there. I think Tim will love to see your sissy body and those deeper tan lines you now have."

As instructed, I removed the robe and placed it on the chair. Clearly, I was getting use to being naked and vulnerable around men. "I love those tan lines on you Jolie. You look so sweet and effeminate. Why don't you come over here and bend over the arm of the sofa."

As she spoke, she stood up and approached me. Once I was bent over, she told me to move my ass up higher on the arm. I was then instructed to spread my legs open. She then had me reach back and spread my cheeks open. When I was properly positioned, she opened an end table drawer and took out a bottle of lubricant and set it on the small of my back.

"Now stay just like that Sissy Jolie. I want your ass to be the first thing Tim see's when he comes in from the deck. Can you guess why I want your ass this way Jolie?"

My heart and mind was racing as she spoke. I looked over at her and with my giddy sissy voice said, "yes Mistress, you have me like this because Tim is going to fuck me. Am I right Mistress Di?"

Mistress laughed at my response. "Yes Jolie, you are correct, Tim is going to fuck you. You are finally going to find out how it feels to take a Real Man's cock up your sissy ass. I'm fairly certain you want it to happen. But, before he does, I want you to beg him for it, I want to hear the conviction in your voice. Tim will love hearing you beg him to fuck you up your ass, and make you a true sissy cock slut."

About 5 minutes later I heard the door open and Tim walked in. I was surprised to see that he was already naked. He stop in his tracks the moment he saw me. "Wow, now that is such a sweet way for a sissy to be greeting a man, Jolie. Is that lube on you back waiting for me?"

Looking at him, well mostly at his cock, I responded. "Yes Tim, the lube is for you. I what you to use some so you can fuck me. I want you to fuck me in my ass and make me into a true sissy cock slut. Please Tim, please fuck me with your beautiful cock. I want your cock up my ass and fucking me like the sissy I am. Please Tim, please fuck me."

Tim walked over to me and knelled by my face, holding his cock out. "Okay Jolie, suck my cock and get it hard so I can fuck you." I wasted no time at all and took him in my mouth. I so wanted to get him hard as quickly as I could. It took only a few moments and Tim was rock hard and ready.

"What a good sissy bitch, you got me nice and hard," he said as he pulled out of my mouth. Tim walked behind me and took the lube. Soon he was running his now lubed finger on my rose and pressing it into me.

"Lets get you lubed and ready for my cock Jolie. I'm going to so love fucking that ass of yours. I am so sure you will love taking my cock up your sissy ass before this night is over."

After a few moments, with Mistress standing over me, he removed his fingers and put lube on his cock. He then positioned himself so I felt the warmth of his mushroom cock head at my rosebud. "Beg me Jolie, beg me to fuck you."

The words poured out. "Please Tim, please fuck me with your beautiful cock. I so want to feel your cock up my ass. Please make me a true sissy cock slut. Fuck me like the sissy I am. I want your cock in me, fuck me, please."

As I begged, Tim pressed himself to me. It took a moment but my rose opened and let his head in. I felt the warm head inside me. Tim stayed still for a moment to let me adjust to him. he then pulled out of me and repeated the action.

He did this several times until my rose easily opened to his cock. Then he slowly he pressed forward a little more. I felt the warmth of his cock on my inner walls. I could feel myself being stretched. Once he had worked maybe 4 inches into me he slowly began to fuck me.

"That's it Tim, fuck that sissy bitch. Fuck him up the ass so he learns what a sissy faggot he really is," Mistress stated. I could not believe how full I felt. I knew there was much more cock to still come.

As Tim fucked me, he slowly worked more of his cock inside me. I loved the feeling of his cock going in and out of me. My body seemed to naturally start rocking back and forth to the rhythm of his pumping action.

"I knew it Jolie, you are a natural born sissy cock slut aren't you? You are loving taking cock up you ass, aren't you? No real man would let another guy fuck them in the ass. You're a failure as a man but you make a great sissy boi. You know this is your life now. Your goal in life is now to please Real Men and their cocks. You know it and you love it don't Jolie?"

I was breathing hard, but somehow managed to say, "yes Mistress I love taking it up the ass like a good sissy. I'm a failure as a man, I'm a sissy." I'm certain the look on my face confirmed what she already knew.

Tim continued fucking me and slowly adding more of his length to me. I felt so full of cock. My walls were being stretched by his invading monster. It was making me feel so good, soft moans and whimpers of pleasure, began slipping out of my mouth.

"That's it Jolie, take my cock up your ass, like a good little sissy faggot bitch. Your tight hole feels so good on my cock. Push back on my cock and show me and your Mistress that you love taking it up the ass. Fuck yourself on my cock, bitch. You know you are a cock slut now, so show us."

Tim stopped moving, and as directed, I began fucking myself on his cock. As slutty as it was, I just wanted his cock in me. I rocked back and forth, working more of it into me. Out of nowhere, I yelled out "Oh god, your cock feels so fucking good up my ass."

After a few moments of that, Tim took hold of my hips and began fucking me again. Before I knew it, I felt his hips hitting my ass cheeks. I was delighted to know I was now taking the full length of his manhood inside me. I was moaning and whimpering in pleasure. The feeling of fullness was amazing.

Without realizing it, I began begging Tim to fuck me more and harder. My mind was completely taken over by the feeling of being fucked. Both Tim and Mistress were laughing and calling me all kinds of names. They were right, I was a total sissy cock slut faggot now. My clitty was leaking fluid as I was being fucked.

"Yes Tim, yes, fuck me harder. Fuck me like the sissy slut I am. I love taking your cock up my ass. Fuck me good." I'm your slut now, fuck me!"

Tim rode my ass for over 15 minutes before he said he was getting ready to cum. I delighted in hearing that, and begged him to cum deep inside me. Seconds later, he drove himself hard into me. His cock grew and twitched and I felt the first warm load of cum splash inside me. Then it kept shooting more and more. I was amazed how good it felt being pumped full of his seed. It was the most amazing effeminate feeling I had experienced.

When Tim was done, he slowly withdrew his cock from me. Immediately, I was overcome by that empty feeling. Then there was the feeling of some of Tim's cum leaking out of me. Mistress scooped it up and brought it to my mouth. "Lets not waste this Jolie, lick it up." Promptly, I opened my mouth and lapped it up.

Trying to regain my sense of composure, I stayed bent over the arm of the sofa for a good ten minutes. My legs felt like rubber. I felt the cool air on my now gaped pussy. Mistress walked over and handed me a towel. "Hold this between your legs. Lets get you to the bathroom."

Thankfully, Mistress held my arm as she guided me into the bathroom. My legs were still rubbery as we walked away. She helped me to the toilet so I could "empty out."

"Jolie, I am so proud of you. You are one amazing little sissy faggot slut boi. The look on your face, as Tim was fucking you, was one of pure lust. I've seen a few sissies who liked taking it up the ass, the very first time, but nothing like you. Be honest with me, now that you have been fucked, how do you feel? Do you want to do it again?"

Looking at Mistress, I smiled. "Yes Mistress I liked it, I mean wow, I really really liked it. Tim's cock felt wonderful inside me like that. When he was inside me all the way, the feeling of fullness was incredible. Feeling him cum inside me like that was mind blowing. Hopefully, Tim liked fucking me as much as I like it. I so want to do it more. The one thing I didn't like, was that empty feeling I got when he pulled out of me."

Mistress laughed and suggest that I should clean myself and then join them back in the living room. She told me that she fully expected that Tim would want to fuck me a few more times tonight. I took my time cleaning my self up. By the time I was done, I was already hoping that Tim would be fucking me again.

When I was back in the living room, I found Tim sitting alone on the sofa, watching some TV. Tim informed me that Mistress Di had gone out to meet with some friends. As I reached for my robe to put it on, Tim suggest that I leave it off so that he could enjoy my body.

Patting the sofa, Tim said, "come over here and sit next to me." I put the robe back down on the chair, and then made my way toward him. I took a seat next to him, very close to him.

"How are you feeling Jolie, did you enjoy that as much as I did?"

I started blushing. "I'm fine Tim, thanks for asking. Yes, I did enjoy it very much so."

Tim leaned in and kissed me on the neck, before asking, "do you want to do it again?"

Giggling, I told him yes. "Do you want me over the arm of the sofa again?"

Tim laughed saying, "no slut this time I want you face down ass up in the bed, like a good little sissy faggot."

Off to the bedroom we went and Tim took me face down and ass up. The second time was even better. While taking a break after the second round, I called Bri to let her know I was no longer a virgin. She wanted details which I promised to give her the next day. As we were talking, Tim walked in with 2 drinks.

"Hi there Bri, how's that sweet sissy ass of your's", Tim stated. Bri told him it had been getting a lot of black cock. She then asked him how he was enjoying fucking me. Tim told her I was a great fuck, and suggested that one day, the 3 of us get together.

Later that evening Tim took me a 3rd time. This time it was on my back. It started with my legs on his shoulders at the edge of the bed. It ended with my legs wrapped around him, my ankles locked, as he hammered himself into my pussy, until he came one more time.

As we laid there spent, with his man seed swimming around inside my sissy pussy, with my head on his shoulder, I asked him if he would fuck me first thing in the morning. I told him I wanted to start my morning as a proper sissy cock slut. The last I remember before falling asleep was Tim saying he had already planned on it.