Oral Servicing Pt. 02

(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.

I dropped them to my ankles, and they fell around my feet. I felt naked and embarrassed with my penis sticking out in front of Debra like this. I tried pleading once more, looking at her pretty face and sexy body..."Debra....please don't humiliate me like this."

Debra slapped my bare bottom hard, and said, "Oh, stop your whining! Spread your legs around that toilet bowl, Sissy! It goes in that toilet bowl where it belongs! You know I don't touch your penis. Spread your legs and slap your balls! Now, two fingers and jack-off! Quickly. In and out. We need to get this over with. We have things to do."

I was feeling so humiliated but at least I got to cum, by my own hand...just fingers, really. I spanked my balls, like she told me and pushed my hips in and out, simulating fornication. I almost fell forward. My knees bent, I grunted, pointed my penis down and emptied myself in the toilet bowl. Debra slapped my buttocks again. "Such a little Sissy! What man would degrade himself like you do? Clean yourself up and get your panties back on," she barked at me.

We were spending a weekend in the hotel room. The following morning, after I woke Debra with pussy kisses and her morning orgasm, Debra told me to take a shower. "Clean your asshole very well. Use your fingers inside. Just wear your panties, thigh high stockings and a baby-doll nightie with a condom." She never said this to me before. When I finished, I came out and Debra was just wearing a top and was bra-less. She said, "Put your heels on too. We're ready for the next step now."

I asked, "What next step?"

"In your Sissy training."

I said, "Debra, please don't call it that."

"That's what it is. You do know I've been training you as a Sissy."

"I thought you said pussy training me. That's what you said in the beginning."

"Yes, Sweetie." (That was the first time she ever called me that.) "It was pussy training, and you've done well."

"Then what's this all about?," I replied.

"You didn't think this was ever going to be permanent, did you? You know I'm looking for woman. I'm training you for both...a man or a woman. There are many men and women looking for a Sissy. Even some couples. I'm preparing you...for your future."

I hung my head.

"Don't be sad. Once you accept this, you'll like it. Maybe even more than pussy. It's like having your own special pussy back there."

Debra was attaching a strap-on dildo to her wide hips.

"Debra, it looks so big!"

"It's a little bigger than average. I'd rather start you this way. If a smaller man takes you, it will be easier for you, rather than the other way around."

"If a man takes me? What are you saying Debra? I want to be with you."

"Sweetie, I've been seeing a woman now for a few weeks. We're starting to get more serious. We're talking about me moving in with her. You knew this was temporary for me."

"Have you been intimate with her? Has she given you oral?"

"Of course! And I've licked her pussy! That's what lesbians do! Now I'm helping you for the transition phase when you'll be back on your own. You should be thanking me for this."

"You're going to help me with that? A fat cock strapped to your hips?"

"Yes, Sweetie. Just relax."

"What about plugs? I've heard about them. Shouldn't we start with that?"

"I don't believe in that. A man is going to plug you with his cock, not a small toy. We just need to give you lots of lubrication, which your partner should do for you."

"My partner?"

"Don't tell me you haven't thought about this."

I hung my head. I guess I had, but never wanted to admit it. "What do we do?," I asked her.

"This training takes a little while but the more we do it the more you will like it and enjoy it. You will usually have a suck a man first. That helps him prepare his cock to enter you. The harder you make him, the better for you. You want him very hard, so he slides in easily."

Debra took her top off and was naked with the dildo strapped around her waist. She adjusted the leg straps around her thick thighs until the phallus was sticking out straight in front of her. That is an image of her I will never forget. I didn't think seeing a big penis on Debra would excite me, but it did. I must admit she looked amazingly hot. She set her laptop in front of me and turned on a picture of a man's hard cock. "Focus on this picture and try to relax. Let's bend you over today. It's an enjoyable position for both the man and the Sissy. Lean forward over the desk, ass out, legs spread. Wiggle your bottom a little to entice the man. Take your panties down to show him how ready you are. Hold your ass cheeks open while he lubes you."

I felt Debra's finger circling my anus and her finger slipped into my rectum. I flinched and pulled up. Debra pushed my head back down. "Just relax. It's just my finger. Focus on the picture," she said.

I was nervous as the head of her rubber cock pressed against my sphincter. She said, "Push back, Sweetie. Until my head is in. The man is going to push in a little hard until his head gets in you."

Debra held steady and I pushed back. I felt her bulb go inside me. I could see her behind me in the mirror over the desk. She was smiling. Her tits exposed.

"Oh, Debra, that feels so big!"

"It's fine. Put your left foot on the chair next to me. It will open you up a little more. Feel your nylon stockinged legs. Men will like that. Just start pushing back. I'm going to hold your hips. I want you to take it all. Go back and forth. Push back into my cock, Sweetie."

I eased back onto Debra's thick cock. A little more entered me with each gentle push. I felt stuffed. "How much more do I have to go?," I asked her.

"Just another 3 inches or so. You're almost there. Come on, take the rest."

I was feeling hot now. It was feeling better. I wanted it. All of it. I wanted to do it for Debra. I pushed back for one final thrust and Debra seated the giant phallus all the way in.

"Debra, I feel so full. My penis is so hard."

Debra patted my ass. "You're all the way. All 8 inches."

"Oh, Debra. It feels so big. So full. So fat in my behind!"

"That's good. That's how it should feel. You can cum if you want. Stroke it. You can use your hand this time. You have your condom on."

Debra fucked me. Her long dong reached places inside me that I didn't know were possible. I used my whole hand and grabbed my penis, pumping it and screamed out, "Debra, I'm going to cum!!"

"That's my good girl. Go ahead. In your condom. It's ok to cum. It shows me you like this."

My ass felt stretched and sore, but Debra said I would get used to it. She led me to the bed afterwards to lick her pussy. She said I did really good for my first time. I wanted to cuddle with her, next to her breasts, her hairy armpits around me, but I knew she wouldn't allow that, so I just snuggled my face into her warm, wet, hairy pussy to comfort myself. I stayed there until Debra had her orgasm.

Over the next few weeks, we spent most of our time together with Debra pegging me in different positions, on my back, my side, from behind and on all fours. As soon as I saw her strapping on the dildo, I got excited and hard and would lower my panties in anticipation. Debra was so wet after fucking me she would have me eat her for what seemed like hours, usually face-sitting me, riding my tongue while she held on to the headboard. I hated to admit this to Debra, but I got more used to her fucking me and started to enjoy it. She allowed me to masturbate while she fucked me, to associate pleasure with my being penetrated. The last time I remember her fucking me, she gave me a hug afterwards, something she had never done before. I feared the worst; that the end was here.

And then, that was it. I never heard from Debra again. In all those months we were together, Debra never touched my penis, and I never touched her breasts. I tried calling, texting and emailing, but I never got a response. She took her profile down on the fetish site. The last entry on her fetish page said, "Trained Sissy available for you," that included several more pictures of me. The day after she signed off her profile, I was contacted by another woman. I think Debra waited to remove her profile until someone contacted me. The new woman said she found me on Debra's profile page. We're meeting for coffee next week. She wants to discuss our arrangement if she takes me as her new Sissy. I figured Debra was with her new girlfriend now and had done her job with me. I will never forget her, and hope she knows that I loved her. I never expected to end up here, as a Sissy, but Debra trained me for this...whatever happens next. At my age, I would never find a normal relationship with a woman anyway. After Debra, I'm not sure I wanted one...