Jessica was saying "You like that? You want that big cock inside your ass? You want to make me cum?" while she grabbed my hips and was pounding me.
"YES! MISTRESS! PLEASE! FUCK ME HARDER!" I gasped. "PLEASE! CUM IN MY BOI CUNT!" and at that moment, I started to cum, my clitty shooting large spurts of cum all over the chair, my own legs and the floor. I screamed "Oh! Mistress Jessica! I'm cumming!"
She smacked my ass so hard I thought I would bleed, saying "Stupid sissy! No one cares about you or your clitty! You are here for my pleasure." And she suddenly with drew the cock from my ass, leaving me open, gaping and wanting more. I started to cry again, against my will. I didn't want to, but I couldn't stop it. I turned around to face her and knelt down.
"I'm sorry Mistress Jessica. I'm sorry I couldn't please you." My tears were streaming down my face and I was sobbing. What was wrong with me? Was I really this pathetic? I was. I knew I had to accept my place.
"I hope you learned your lessons today and expect you to do better tomorrow. Now get out." She said.
Sniffling and drying my tears, I collected my bag, and I walked out. I was so ashamed. For being weak, for failing. For embarrassing myself. For not being good enough. I went to my car, and sat in the parking lot thinking about it, and I started to cry again. After a few minutes, I was all cried out. I dried my face, and fixed my makeup as best I could, and drove. I didn't go home right away. I drove to the nearby town, looking for a shop or a mall where I could buy a purse, and maybe something special to surprise Jeff. I found a mall about 30 minutes away and felt like everyone was staring at me. Was it because I looked like a man? Or did these men desire me? I ignored the looks and picked out a few nice things, including some lingerie, jewelry and a much-needed purse. After my shopping excursion, I felt better mentally, and more determined, so I drove home.
I was so happy to see Jeff when I got there. It was later in the day than I realized. I had been with Jessica all morning and shopping all afternoon. My ass hurt from the fucking and I felt like a mess. I went into my apartment, took off my clothes, showered, shaved and ate some salad I had picked up. After the hot shower, the food and a nice cup of tea, I felt better. I really wanted to impress Jeff. I wonder what he had planned for tonight.
Jeff came downstairs while I was getting ready. I had already dressed and was finishing my makeup when he said "Well, don't you look nice!" I blushed a little, beaming at the compliment. I wanted to stand up and kiss him. What a strange thought. I WANTED TO. He walked over and stood behind me while I was sitting in front of the dresser and put his hands on my shoulders, and we looked at ourselves in the mirror. I picked up his hand and kissed it a little. An endearing gesture. He smiled and said, "I think we make a nice couple." I wanted to leap into his arms, but I held myself back, not wanting to be desperate.
I gathered up some courage and asked "Jeff, do you think this, I mean, me, us, could be, you know, something permanent? I mean obviously, I don't live here, but if I ... changed, could I be what you want? Or is this just a 'thing' you are doing?" I needed to know before I got my hopes up.
I was watching his face for a reaction, but he was impassive, contemplating. He said "I don't know. I thought this was fun when it started. I've never done this before, I mean, with a guy. In the past few days though, you have really started to seem more like a woman to me, but not. Women are complicated, and selfish and needy. If I think of you as a woman, I like it. I like you. But you aren't a woman."
My face betrayed how hurt the last part of that was. I wanted to be a woman, for him. Didn't I? I said finally while finishing my makeup "but if I could be MORE of a woman for you? With breasts? My own hair, not a wig? Not... pretending?"
