(Please read Part 1 first)
Over the next several weeks there were many changes to our relationship. I still hoped Debra might want to someday have me as her boyfriend, or husband, but that didn't seem likely. Still, I did everything I could to please her. I hoped someday she would let me go in her pussy and maybe allow me to at least fondle her breasts, maybe suck on them. But I was losing hope for any of that. She didn't think much of me as a man, much less at a potential boyfriend.
In our hotel room time, I was now dressing completely as a Sissy for her. This isn't what I planned for when I placed my ad on the fetish site looking for a woman wanting oral sex. I thought I might just meet a woman who enjoyed that, and it could develop into something more. Instead, now Debra and I were shopping together at thrift stores to help me find more outfits. She would embarrass me by holding dresses, slips and skirts up against my body in front of other customers in the stores. Once she asked a store clerk at the check-out, "If these don't fit her (pointing at me) can we return them? Or can she try them on here? She has her panties on." I turned beet red. Fortunately for me, the try-on rooms were for real women only and I didn't have to go in there. But if I wanted to keep Debra happy, this was my life now.
Debra gave me most of her old dresses and skirts since she only wore pants now. I did like getting her old bras and panties. I wanted to please Debra, so I wore what she told me. I now had many dresses, skirts, panties, bras, garter belts, stockings, pantyhose, shoes, slips and lingerie. I even had a panty girdle and corset. She said I was fat even though she weighed far more than me. I also had to get some gaff panties to give me a smoother look down there. She had me get my ears pierced so I could wear earrings. She wants me to have my nipples pierced. I will do it if it means keeping Debra happy and in my life. She would like me to pierce my tongue too, for her clitoris stimulation. She usually picks out what I'm going to wear. I usually must wear pantyhose since they keep my penis tight against my body so as not to rub against her.
Debra was always taking pictures of me, thankfully sans my face, mostly in Sissy outfits in various sexual and embarrassing poses. Sitting, one nylon encased leg crossed over the other. Up the skirt of my dresses. Caught twirling, with an open flared dress on. Even pics of my cum soaked panties outlining my erection! I looked up her fetish account just to see if she was still looking for a female. What I saw were some of these pictures of ME, posted under her profile page with the words, "A new Sissy I'm training." It left me little hope she would ever consider me as her lover or boyfriend. Further, it said to me that she may have done this to other men. But I was falling hard for Debra and didn't want to give up my hopes. Debra was too special for me to give up on. But every time I went back to her account, she added more new pictures. I never mentioned any of this to her. I was afraid she would be upset for me for even looking at her account.
Thankfully, I didn't have to wear much make-up. Debra said, "You're a sissy, not a girl!" But Debra always told me to wear lipstick. She loved to see my lip prints on her inner thighs. I had several shades from light pink to dark red. And she liked me to clip little bows in my hair.
She cut her hair and dyed it jet black. Very short and spikey. Some would say it was "butch" or "dyke." To me it was just sexy. Everything about Debra was sexy to me. I thought if only I had a vagina maybe Debra would make love to me. But I really wanted her to like my penis and let me make love to her like a real man. That was the furthest thing from her mind. She continued to humiliate me and demand more from me.
She had me shave off all my body hair, even my armpits, although hers remained hairy. My crotch also was now shaved smooth. Debra said, "It will make you feel better in your panties and stockings with smooth skin." I must admit it did feel better. But now I looked like a little boy down there. "It's a cute look for sissies," Debra told me. Debra was still hairy, the way I liked her anyway. But we were such a contrast now. I didn't have to wear the diapers as often anymore either which was a relief to me. I dressed in sissy clothes to pleasure and service Debra. Although she still made me wear a condom over my penis inside my panties.
She wanted me to bathe her now too. Her tits were still off limits to me, but I could wash them if I used a washcloth and not my hands. I secretly longed to kiss her breasts and suckle her. She taught me how to shave her legs and I would wash and brush her hair. I love when she gets on her hands and knees in the tub, and I get to loofah her big bottom. I'm careful when I wash her pussy, not to be too rough. But she lets me use my hands and fingers there and that makes it nice for me to wash her there.
I would always have to apologize Debra for anything she felt I did wrong. The bath water was too hot or too cold. Not enough bubbles or too many bubbles. She liked to play on her phone in the tub while I washed or shaved her. One time I forgot to bring her phone to her phone when I started her bath. I apologized, but she said, "See why I don't want a man in my life? They can't do anything right!"
I thought to myself, "Its just your phone," but after her bath Debra punished me. She sent me to stand in a corner and face the wall.
Debra told me, "Hold your dress up and pull your panties down." I didn't question her; I just did what she said. I didn't want to make her more upset with me. She knew I was jealous of her vibrator because I feared it made her happier than I could. With my back to her, I heard her vibrator turn on. Very apologetically, I repeated, "Oh, Debra, I'm sorry, I'm sorry. Please don't do this to me. I know I'm useless sometimes. Please forgive me and let me use my mouth for you." I felt so foolish. The way I looked. Practically begging to lick her. Doing her bidding.
She ignored my pleas and said, "Just stay there until I tell you." Then I heard the familiar buzzing. She turned on the TV to cover the buzzing sound and the buzzing and her moaning continued for at least another 20 minutes. When it stopped, I thought she was done, but I didn't hear her orgasm. She moans out quite loudly during other orgasms. She called out to me, "Bring me a glass of wine and my big black dildo." I dropped my dress and started pulling up my panties, scurrying round quickly to get what she wanted, so I wouldn't displease her. "I didn't tell you to pull up your panties! Hold your dress up, leave your panties down and go get what I told you!" I apologized again, repeatedly as I shuffled around the room with my panties still down. I poured the wine with one hand, still holding up my dress with the other. I brought her the wine and went to get her dildo. I hated that thing. It was so big, and she would take it all in and she wouldn't ever even let me put my little penis in her. She paid no attention to my little pink boner when she told me to go back to the corner.
I heard the buzzing again and this time her pussy sloshing sounds. I knew she was using both implements. It was another good 10 or 15 minutes until she was done. I knew her vocal sounds when she came. When she was done, she said, "Panties up! Here. Take this dildo out of my pussy and my vibrator. Lick them clean and then go wash them. Next time you won't forget when I tell you to do something!" Her pussy hole was stretched open, gaping, creamy and oozing.
"Debra, your pussy looks so beautiful right now, all spread, open and wet. Can I just lick you up a bit and clean your pussy for you?" My face flushed red again. Thinking how pitiful and pathetic I must have sounded.
"Ha! You want a reward for bad behavior? Go clean up the toys and bring me a washcloth. Put your nightgown on and get in the other bed. You can lick me awake in the morning."
Debra became so demanding. I think it was to push me and see how far I would go and what I would do to please her. She often suffered from cramps. A woman her size isn't eating healthy and caring about her weight. This often left her feeling bloated and cramped. She would have me rub and massage her belly while she laid in bed naked until she passed her gas. I struggled with the smell, but I never showed it. I know the belly rubbing felt good to her and relived her, but she never said "thank you" to me. I also gave her full body massages. And she made me in charge of her footcare. She loved foot soaks and massages.
I was always hard around Debra. It annoyed her and made her mad. She usually ignored it, but once, while I was changing outfits, she was particularly upset seeing my erection in my panties. She angrily barked at me, "Do you always have to get hard every time you put on your panties? Do I need to let you jack-off again?"
"Oh, Debra, I wish you would help me and touch me, just once, please?"
Debra looked angrily at me and grabbed my balls in the pouch of my panties. She pulled on them, stretching them down. "Listen to me! Do your sissy business now, in the toilet, or put your dress back on! And you can have a boner in those panties and not come near me the rest of the night! Do you understand me?"
"Yes, Debra. I'm sorry. Being here with you and...well, yes, the panties do make me hard. I'm sorry."
I sheepishly stepped towards the toilet and raised the seat.
"Pull your panties down!," Debra shouted at me.
