Oral Servicing Pt. 03

(Please read Parts 1 and 2 first)

I met the new woman about a week later. She had emailed me, said her name was Helen, and said Debra had sent her my file, whatever that meant. I didn't know Debra had a file on me besides the pictures she took. The woman was rather brazen and said she wanted to interview me at 2 pm that day and told me to meet her at her house. It was a Tuesday. I was depressed about Debra and didn't really even want to go. But if Debra recommended me to her, I thought I should honor Debra and go. When I met her at the door, I wasn't expecting to meet such an old woman. I thought she must be 85! I must be at the wrong house! I asked, "I'm sorry, is Helen here?"

"I'm Helen. Please come in. You weren't expecting someone like me, were you?"

"To be frank, Ma'am, no." She was about 5'4, all grey-haired, small frame.

"Well, it is Robert, isn't it?"

"Yes."

"And Debra called you Alice?"

Now I knew I was at the right house. "Ummm, yes, yes she did."

In a very pleasant voice, she said, "Well, Alice, you can just call me, Helen. I prefer that. It's nice to meet you! Please come in, Alice." Debra said in her email that you wear diapers. I have one here for you."

I blushed and turned red-faced. "Oh, no, Helen, I don't like to wear them."

Helen's tone turned stern and serious. "Alice, sissies never wear male clothing in my house. So, you have 1 of 3 a choices now. You may stay by putting on the diaper or come in naked, or you can leave right now, and this interview will be over. If you decide to stay, put your clothes in the trunk by the door and close the lock. You have 5 minutes to meet me in my living room, naked or in the diaper that I was kind enough to leave out for you, or shut the door behind you on your way out! I assure you I am alone in the house and no one else will see you."

I knew Debra must have must communicated with this woman. I wondered what was in my "file" and what pictures of me this old woman, Helen, had seen. I wondered if this was serious but had only minutes to decide what to do. I thought I should at least stay long enough to find out about all this. But humiliating me at the door? I certainly didn't want to walk in naked! The diaper at least covered me, but it's so embarrassing for me to wear it. Especially in front of this new woman that I've only known for 2 minutes! This woman knew what she was doing. I had to decide quickly. I guess if Debra spoke to her, it would be ok. I stripped down and put the diaper on. With about 1 minute to spare I walked into Helen's living room, feeling ashamed, covered only in my diaper.

Helen stood up to greet me. "I see you made a good sissy choice and decided on the diaper. Turn around." I turned completely around with my hands in front of my genitals. Even though I was covered by the diaper, I still felt embarrassed. I couldn't believe I was even doing this. I remembered that Debra was fast with me when we first met, but at least we had a lunch meeting the day before. I got lost in my thoughts while the old woman stood with her arms crossed over her chest and looked me over. Helen finally spoke to me, "And I see you're keeping up on your shaving like Debra taught you. Do you have any trouble shaving around your anus or doing you balls?"

There was no small talk. She started right in on me. I wondered if Debra might have just been setting me up for the this to make a fool out of me. But I couldn't take any chances now. My clothes were locked up and Helen sounded very serious. I knew her question was serious and not to be ignored. I thought it best to answer her truthfully. "Well, yes, those are a little hard to get to."

"I'll be inspecting you and helping you with that."

What was she saying to me? Who was this woman? She was probably at least 20 years older than me, maybe more!

"Now that you're in something more appropriate, let's have a proper greeting from you. Kneel in front me." My head was spinning. I just followed her directions and kneeled. Helen lifted her dress and said, "Smell my panties, Alice. Press your nose into them."

I had been in this woman's house for less than 10 minutes. Really, a stranger to me. And here I was wearing a diaper, on my knees in front of her pussy! What was I doing? But she was from Debra. Helen's voice was pleasant at times, demanding other times. I felt confused, but almost compelled to listen to her and do what she said. She wore beige nylon granny panties, but I was surprised she wore an old-fashioned garter belt with her hose. I could smell her pussy scent right though her panties.

When she was satisfied, she told me to take a seat. I sat in a chair across from the couch where Helen sat down.

"Now, Alice, you got off to a poor start with me, didn't you? You disrespected me in my own home."

I didn't want to upset her. "Yes, I'm very sorry about that."

"Always remember, Alice, you will always respect me. I will always know what's best for you and I expect you to follow my directions. As a sissy, you should already know these things. They are basic rules for sissies. Now I have to ask you about a few things first. Debra told me you're reluctant to admit that you're a sissy. From what I've seen so far it appears this is true. Is that correct?"

"Well, I never thought of myself as a sissy before Debra."

"I understand that Debra had trained you for a life of sissyhood and servicing. As an older, twice divorced former male, with no prospects and a small penis, I can understand why Debra found you to be a good candidate for sissyhood. I know it can be hard for you to admit this. But it's really nothing for you to be ashamed of. But this didn't start overnight or even with Debra, did it, Alice? I'm sure you were a panty sniffer as a young boy and played with your sisters or mother's clothes or even your former wife's. I was married to a Sissy for over 40 years until he passed two years ago. I know how they act and what they do. I caught him early on in our marriage wearing my clothes and masturbating, and our marriage changed immediately and permanently. He tried to hide it, deny it, and felt ashamed, just like you do now. I gave him a choice. Leave and we get divorced or live the rest of his life as my sissy. He was an accountant and I threatened to expose him if he ever changed his mind. There was no going back. He made his choice. I never had normal sexual relations with him again. I teased and embarrassed him about his decision. The more I humiliated him the more I found it exhilarating for me. And the more humiliating he felt the more excited and submissive he would become. I'm 84 years old now and we lived a very kinky life. But I'm not done. My pussy still requires attention. I'm not looking for some old man on Viagra trying to fuck me. I want another Sissy to pleasure me as I see fit. Alice, some men are sissies. You are what you are. You can't change that. There is nothing to stop you from leaving. If you make this decision now, and you say no, you are free to leave. If your choice is to stay, rest assured you will be emasculated and humiliated. You will be a sissy. From what I've heard from Debra, you are a sissy. Are you ready to confirm that now and make this commitment?"

I hung my head in silent shame. Fifteen minutes after meeting Helen she wanted a commitment to her. She already had me in a diaper and smelling her pussy. She had the right words for me, even though I didn't want to admit it. She knew what she was doing. But did I want an 84-year-old granny, 22 years older than me, that I would be required to pleasure at her discretion? She already got me excited by smelling her pussy. Debra did the same thing to me. The smell of a woman's pussy can addict me to her. That's why she did it. She knew I would find it hard to leave after smelling her there. Even if she is 84 years old.

Helen said, "You're looking down at the floor, Alice, feeling ashamed. Look at me. I know how you're feeling. My husband reacted just like you in the beginning. But if you accept that you're a Sissy, it will be very freeing for you, and you'll love servicing me. Think of it this way, Alice. We all have needs. My need is to be pleasured. Your need is to pleasure me, as my Sissy. I understand your needs. I have a dominant nature. You're submissive. Alice, what you do between my legs stays between us. But you'll be in your happy place between my legs when you're servicing me. You'll be begging me to have your tongue in my pussy. Now, Alice, let me ask you one more time. Are you ready to confirm that you are a sissy and want to commit to me? Otherwise, you are free to leave."

She had me. I couldn't say no. I said, "Yes."

"Yes, what?"

"Yes, Helen. I'm a Sissy. I will commit to you. I want to be between your legs for you."

"Good. That's how a real Sissy responds. I knew you'd make the right decision again. And it didn't take you long. Now, go in the kitchen. You'll find panties, stockings, and an apron on the table. Put them on. Pick a shade of lipstick. My husband's heels are there and should fit you too. Put them on, then come back and see me."

"Right now?"

"Why not, right now? Are you questioning me again? I don't believe in wasting time. You just made a commitment to me...to my pussy. Now go put the clothes on. You don't ever wear men's clothes in my house."

I went off to the kitchen, undressed and put on the clothes. When I came back into the room, Helen didn't look the least bit surprised that I followed her directions. All she said was, "Lift up your apron. Show me your panties, sissy." I did as she said. My little penis was hard and tented my panties out a bit.

"Alice, I expect you to worship my pussy. That's what a sissy does. Now, on your knees and crawl over here, between my legs. Get my skirt up and take down my panties."

I crawled over to Helen, and she surprised me by reaching into her bag and bringing out a dog collar. It was pink, but definitely a dog's collar. She put it around my neck. She said, "You will always wear this when you're here. It's not a slave collar. You are not a slave but here willingly to service me. I only attach the chain when you're at my pussy to keep you in place and guide you. I pull on the chain when I want you to draw in deeper to my pussy and I relax the chain when I want less pressure. I can also guide you to the right or left with the chain. Some women guide their sissy's head with their hands or tell them vocally. I use the chain. I will keep it taught when I'm near orgasm. I also use the chain for the same reasons when you pleasure me anally." Helen attached the chain to my collar. I knew this meant she was going to have me service her now.

I helped lift her skirt to around her waist. I didn't notice the first time that she was actually wearing an old-fashioned garter belt with four straps on each leg holding up her nylons. For an old woman, I liked her sexy look. Debra never wore anything even remotely sexy with me. But of course, she was a lesbian dyke. I gently took down Helen's granny panties. Her legs did look nice in the stockings. I licked her nylons on instinct, up near the tops of her stockings. She seemed to like that but didn't say anything. I was already imagining being able to rub my nyloned legs against hers. That would be such a treat for me, but I doubted if I should be asking her for anything. She was in complete control.

She had very little natural hair left around her shriveled, prune-looking pussy, a few long curly strands of mostly gray and blonde. But something about seeing this old woman's pussy aroused me. Her dark brown, long pussy lips stood out against her fair skin. I licked her wet labia and not surprisingly, I got even more excited. I started leaking in my panties. Although she didn't have the soft, thick thighs and hairy pussy like Debra, I felt like I was back where I belonged, between a woman's legs, eating her pussy...Helen's 84-year-old pussy.

"There, isn't that better?," she said to me. You're where you belong, eating my pussy. I've had a lot of cocks in there over my many years and a lot of pussy-eating sissies. You'll be spending a lot of your time down there, where all those cocks have been. It's like you're sucking all the cocks that have been in my pussy."

Helen didn't get excited at all while I licked her. Apparently, she was very used to this. She's obviously had a lot of sexual activity over her years, and I would probably have to work to give her orgasms. She spoke very casually to me while I lapped at her pussy, almost like I wasn't even down there, and she was just having a casual conversation with a friend. Every once in awhile she pulled the chain tighter and then would loosen it. She asked me, "What was your ex-wife's name?"

"Pam."

"How long ago was that?"

I answered her questions in-between my licking. "Over 20 years ago."

"How long since you've been in a woman's pussy with your penis?"

"It was last, with her, more than 20 years ago."

"How long has it been since you've had your penis sucked?"

"That would be Pam too. I didn't date much until Debra."

I was trying to satisfy Helen, but she acted as if I wasn't licking her pussy at all and kept on with her questions.

"Do you still love Pam? Miss her? Miss her pussy?"

"Yes, Helen, I do."

"But you couldn't please Pam sexually, could you?"

"No, I couldn't"

"And you felt emasculated."

"Yes. She stopped having any sex with me."

"How did it end with Pam?"

"I wasn't having sex with her anymore. I was frustrated."

"And?"

"She caught me wearing one of her bras while I was smelling her panties and masturbating. The divorce was final two months later. She remarried 3 months later."

"And what if Pam could see you now? Her former husband, a sissy now, dressed in panties, stockings and heels, on his knees, lapping at an old lady's pussy like he can't get enough. While she's probably at home, in your old house, with her new husband fucking her. Just so you understand, you won't be doing any fucking or getting any blowjobs here either."

I didn't think Helen wanted me to answer her. She didn't need to pull the leash. I tried to tongue her, deeper into her pussy. She knew she was humiliating me and that's what she wanted to do to me. She answered her phone while I was between her legs and relaxed her grip on the chain. I could only hear Helen talking. "Hi, Julia. Yes, he's here. He's between my legs right now. (laughter) Of course! He's in panties, stockings, an apron, and Cindy's old heels. He stripped and put on a diaper 2 minutes after he got here. (more laughter) Good tongue. He's getting good into my pussy now. Been at it at least 20 minutes. I have to go, Julia. He's about to make me cum for his first time. I'll see you here Sunday. I want to spend Saturday with this new one." She brought her wrinkly fingers down to her pussy and opened her large, flappy labia lips. She lifted her clitoral hood and pulled tighter on the chain. "My clit," she called out to me. "Lick my clit until I cum. I have a big button. You'll enjoy stimulating it." She was right. Her clitoris must have stuck out at least 1/4 inch! Longest I've ever seen! It looked like a little tiny penis head! Helen held the chain taught and I knew she was ready to cum. The women I've been with all closed their legs after they had an orgasm. Not Helen. She seemed to open her legs wider and told me to just keep my mouth over her pussy and relaxed her grip on my chain. Not to lick or anything. Just to hold my mouth on her. I don't know, but I was getting so turned on by this Dominatrix. At least that's the way I was starting to think of her. Maybe she was right, and I'll be begging to lick her pussy.

After she calmed down, she took the chain off and I brought up something to her. "Helen, you said this would be private between you and me and yet I just heard you talking to someone on the phone about what I was doing to you."

She continued, "Oh, that was just my friend, Julia. She's my best friend and the only one who knew my husband was a Sissy. She will be here sometimes, usually on weekends. You'll serve us coffee or tea and make lunch for us. We like to sit naked on the couch together and watch TV. We're not gay, but sometimes we kiss, especially when we're naked together. She's married but her husband lost interest in sex many years ago. So, she gets lonely and so we kiss and play a bit. We like to suck each other's tits. She spends the day naked with me. Sometimes we play Scrabble at the kitchen table. And sometimes on nice days, we'll take our coffee on the patio outside. My backyard is very private. You'll apply our suntan lotion and service our pussies. She's a little chubby but she has a nice pussy, and her tits are bigger than mine. You'll like her."

"But you also said that I'm a new one. You've had others besides your husband?"

"Oh, yes, of course I have! In fact, I just finished training a sissy about a month ago. A young one, about 28 years old. I trained him for a friend of mine from the fetish website, where I found Debra and you. A male friend. I did it as a favor. He wanted a young new sissy as a houseboy and his cocksucker. The young man, who I named Chrissy, had an ad up looking to be trained. I had him dressing and doing chores. He practiced on a dildo and I mouth-fucked him. Of course, he also paid homage to my pussy too, or I never would have trained him. You see, Alice, most sissies know who they are at an early age. It just took you a little longer to admit it."

Helen got out a notebook and began to dictate her rules. She rattled them off to me:

1. No man clothes are to be worn in her house. There would be a trunk by the door. Strip and leave all my clothes in the trunk and lock it. Walk naked to the guest bedroom, the one used by her late husband and change there.

2. Dresses, skirts with panties, bra and stockings, with heels, must be worn daily. Lingerie will be worn at night.

3. She wanted me Tuesday nights and as a live-in on weekends. She didn't like to do housework and I would be assigned chores on the weekends. Vacuuming, dusting, dishes, washing floors and doing her laundry. Her panties and bras were to be hand-washed only. I would take my clothes home to be washed.

4. She said she didn't like maid uniforms. Chores would done in a little schoolgirls outfit. White button-down blouse and white bra, pleated plaid skirt, white panties, ankle socks and black and white saddle shoes.

5. She would cook for us. I would do all the clean-up.

6. She has a bell. Whenever she rings it, I was to come to her right away.

7. I was to use the guest bedroom. It was her husband's room, and I would be free to wear any of the clothes left there.

8. Her bedroom was off-limits except for cleaning, putting away laundry and changing her bed. Only if she rang the bell at any other time.

9. Never call her. We will communicate by email only.

10. No dating or chatting with any other women. There will be gay porn magazines in my room to keep my mind off other women.

11. Rules would be posted on a mirror in my room.

"Do you understand these rules, so far?" I acknowledged I did. "Good," she replied. "Here are a few more. No kissing. You're not my boyfriend! Always sit when using the toilet and leave the door open. Use the feminine wipes on your penis. Wipe any drips around your head and use them on your shaft and crotch."

I was feeling ashamed and embarrassed having Helen talk to me this way. I felt like a child being talked to by his mother. I guess Helen was old enough to be my mom. But I already made my commitment to her, and I couldn't help feeling excited the way she talked to me. I answered her, "Yes, Helen."

"Make-up is not a requirement but there is a vanity table in your room. It would please me if you experimented with the make-up there and surprised me sometimes, especially on weekends."