The (Fat and) Happy Hooker Ch. 05

Anal

When I got home I looked at my phone (I never take it with me when I’m working) and saw that one of my regular clients had texted that she would be in town for three days and would like me to be with her. I quickly checked my calendar, found I was free, and texted back that I was available. She sent me her flight information and I had a few hours before the flight came in so I selected my outfits, packed a bag, and took a nap. I knew it would be a long night.

Vickie is pretty typical of my female clients. She was a successful woman in a man’s world, climbing the ranks to be Vice-President of something or other in a Fortune 500 company. She was married with two kids. She was, in other words, responsible for something 24/7/365 as they say. What she wants when she’s with me is to be relieved of all responsibility. And I love fulfilling her fantasy.

When I woke I showered and then went to work giving her what she wanted. My hair was simple, I just pulled it back into the tightest bun I could manage. The face took more time and effort. I like to think I’m pretty, but I’m also big and round. It’s hard to make a soft round face look severe. But with careful application of eyeliner, eye shadow, rouge, and blush I think I pull it off. The pale blue contact lenses and scarlet lipstick and nails help too.

I made the trek to Denver International Airport, looking as it always did like some weird bedouin encampment, and parked in the short-term lot before heading into the greeting area.

She waved to me as soon as she spotted me and I waved back.

She looked like exactly what she was, a successful businesswoman. She was dressed much like I was in a severe black pants suit, a very white shirt, conservative jewelry, and sensible walking shoes. Her suitcase, one of those leather bags with the wheels and the pull-behind handle, followed her dutifully. She was blonde and cute rather than pretty. She was one of those blondes with thick hair and soft skin who had wrinkled badly when menopause struck. She was still attractive, but in a grandmotherly way if that makes sense.

She was almost breathless when she took my hand and tugged me toward the woman’s bathroom. “God, I can’t wait to change,” she said as she dropped my hand and went into the restroom and disappeared behind a stall door.

I waited, knowing what was coming.

When she stepped out of the stall she was completely changed. No longer the severe businesswoman, she was a little girl with wrinkles. Her blonde hair was in pigtails and her face was scrubbed clean. She had no jewelry. She was wearing a blue pinafore over a very white puffy-sleeved blouse, obviously imitating Judy Garland’s Dorothy in the Wizard of Oz. When she did a quick turn ruffled underpants peeked out. I couldn’t resist looking at her feet but there were no ruby slippers, just black and white saddle shoes.

She giggled as she came over and took my hand.

“Can we get some ice cream?” she asked in a high-pitched girl’s voice.

“Sure honey,” I said, patting her head and taking charge of her suitcase.

I tossed the suitcase into the back seat and headed for Joe’s Drugs, a place I knew where they still kept the soda fountain running.

She asked if she could have a milkshake and I ordered two, chocolate for her and vanilla for me. While we sat at the counter I watched as her transformation continued. Her voice got higher and she developed just the hint of a lisp. She told me of things she had learned in school, getting wide-eyed when she would tell me some little secret.

She giggled when she told me about how a boy had tried to kiss her and assured me she was still a good girl.

I laughed at her silly jokes and told her she could pick the movie that night. When we got to the hotel I checked us in, using the credit card she had given me, and we went up to the room.

Over time I had gotten used to what she needed so I told her to get undressed while I made popcorn. I tossed the Orville Redenbacher’s Movie Popcorn bag in the microwave and shrugged out of my jacket and blouse, leaving me in only my slacks and nursing bra. When the popcorn was ready I put Netflix on the TV, selected “Kids” and sat back.

Vickie came back into the room, skipping lightly, dressed only in her ruffled panties. She was almost boyish, a small woman with nearly non-existent evi olan gaziantep escort breasts. She giggled as she snuggled against me and selected Frozen II. As the movie started she snuggled against me and we started eating the popcorn, one little white ball at a time.

I was actually enjoying the silly movie and when she started nuzzling at my breast I just automatically unhooked the flap of my nursing bra and let her nurse. She worked her way around until she was laying on her back, her head in my lap, and closed her eyes while she suckled. My hand worked its way down her belly until I found the hard little button of her clitoris and began gently, slowly, masturbating her.

The movie actually had my attention and I yelped when she bit down with her orgasm but I didn’t stop what I was doing. I took her through a half dozen orgasms, each more intense than the last, until with a final scream she emptied her bowels and her bladder.

“Mommy,” she said, “I had an accident.”

I patted her head. “It’s okay honey,” I said, “we’ll clean you up later.”

She nursed and I continued to eat popcorn until the movie was over and then I took her into the bathroom. I pulled the dirty panties off of her and threw the sodden rags into the trash. I turned on the shower, cold, and stood her under it.

I watched as she stood, shivering, while I took my own clothes off. I blended some hot into the water and when it was right I stepped in and started soaping her down.

She was an amazing mixture of young and old. Her body was trim, she obviously worked on it, almost girlish. Her hair was blond with no hint of grey. Her body was absolutely hairless. Her face, though, had never been worked on and she was one of those blondes with that wonderfully fair skin as a girl whose face becomes a mass of fine wrinkles as she ages.

I cleaned her up, dried her, took her into the bed and laid her on it, and then powdered her butt and her pussy, lifted her by her ankles, and slipped her diaper under her. I did up the tabs, patted her butt, and said, “bedtime honey.”

“Can I sweep wif you mommy?” she said, now reduced almost to baby talk.

“Of course honey,” I said and crawled in with her.

She snuggled against me, nestled her head into my arm, latched on, and within a couple of minutes she was snoring softly as I stroked her hair and hummed a little lullaby.

I gently broke her latch on me and went to the bathroom, peed, turned the tv onto the news, and drank a beer. Vickie’s easy money.

I spent the next hour thinking about Jacob and Marta and their “problem.”

Then I crawled back in bed with her, smiled at the way she lay there on her side, sucking her thumb.

I was asleep in a couple of minutes.

In the morning I cleaned her up. As usual, she had filled her diaper so I got the dirty one off of her, threw it into the trash, and got her into the bathtub. I bathed her as she sucked on her pacifier and then gave her a bottle of breast milk (not mine, obviously) and held her head in the crook of my arm as she sucked it down.

The transformation always fascinated me when I was with her. She stepped out of the room as a toddler in her diaper and rubber pants and walked back in, a few minutes later as the executive she is. She looked professional and you had to look very closely to see the thick line of her pullups under the tailored pantsuit. But I could see it. I knew where to look.

“Back for lunch?” I asked, “Or will you be wanting me?

She smiled and said, “I always want you, honey, but it’s a working lunch day. I’ll show you off at the banquet tonight.”

So I kissed her goodbye and headed down for a spa day. One nice thing about a free day with a room key, you just write the room number for whatever goods or services you want and this hotel had some VERY nice goods and services.

The spa was a full three-hour treatment. I steamed and swam, first in a pool about blood temperature and then in one that felt like it was barely above ice. The massage, with the hot rocks and all, left me limp. The makeup girl and hairstylist did the best with what they had, and with my mass of almost black hair, they had quite a bit.

I figured I deserved a new outfit or two so I stopped in one of the dozen gaziantep evi olan escort clothing stores and picked out a nice bright red long flowing pantsuit. They didn’t have red stiletto heels in my size so I settled for some simple pumps.

I went ahead and had lunch in the rooftop restaurant since I hadn’t been invited to Vickie’s gig. The double lobster with the trimmings added a quick $200 to her room bill.

Up in the room, with nothing in particular to do, I turned my phone on and figured I’d go ahead and check my messages. I turn it off when I’m with a client.

One message, from a repeat client, named Roger if it matters, booking me for next month. He knew my date book tends to fill early. I liked him and it was easy money so I texted back, “Done.”

Then there were the 54 missed calls from Marta. I was thinking, clearly, “WHAT THE FUCK, 54?” as I hit “call” on the last one.

“Mandy,” she greeted me, her voice loud and sharp, “where the fuck have you been?!”

So I hung up.

Surprising me not at all, the phone rang in about 10 seconds. It showed “Marta” on the screen.

“ONE FUCKING WORD AND BLOCK YOU!” I said by way of greeting.

I waited a few seconds and then said, “Okay, now what the fuck exactly has your oversized panties in a wad, Marta?”

She said nothing and I giggled.

“You may speak,” I said.

“Mandy,” she said, much subdued, “I’ve been trying to get ahold of you for two days.”

“I have other clients, you know,” I said, “and I’m with one now.”

“When can we,” she started.

“You and Jacob are on my schedule for a week from Friday,” I said.

“We’d like to,” she started again but I cut her off.

“We can talk then,” I said, “and do NOT call me between now and then.”

And I hung up.

So I spent the rest of the day just laying around, doing not a damn thing. At my level, being a whore is not exactly back-breaking work.

I laid around, watched stupidity on television, caught up on the news on Fox, and, generally, did nothing.

When she walked in I was laying on the bed, naked, in one of those “seductive” poses I’ve practiced over time.

“Are you a dirty girl?” I asked as she stopped and looked.

I liked that she blushed before saying, “yes.”

“Well, come here honey,” I said, lifting my breast, offering my nipple, “let mommy take care of you.”

She stripped quickly, leaving her expensive suit and her bra in a pile on the floor, and then crawled up onto the bed in just her pullups and latched on like the hungry baby she was at that point.

I stroked her hair while she suckled, her saliva and drool making a reasonable facsimile of leaking milk on my tit and down her chin.

“That’s my good girl,” I crooned as she nursed.

Her fingers found my clitoris, timidly at first but then more firmly, as she started masturbating me while she nursed.

“That’s my good girl,” I crooned some more, “make mommy happy.”

She released my nipple then and began kissing her way down my body.

She was very good with her mouth when she got to my pussy. Well, she had better be, she had been a client of mine for a couple of years now on a regular, two or three times a year, basis. She brought me along nicely, her tongue busy, her mouth sucking, adding pressure slowly until I was swollen and filling her mouth.

When I came she coughed, spewing my natural lubricant over my belly.

Then she crawled up and snuggled against the side of my breast, her lips nuzzling.

“Thank you, mommy,” she said.

I held her for a few minutes, snuggled against me.

“Okay, honey,” I said, patting her hair, “let’s get you cleaned up for your banquet.”

Another sodden diaper went into the trash and another dirty ass was hosed off in the shower. She would be wearing a dress tonight so there was no need for the relatively discrete pullups. I put her in a full-blown diaper with the tab closures and the heavy padding between her legs making her walk a little bow-legged. A couple of wraps of ace bandage and her already-small breasts were completely flattened.

I watched, fascinated as always, as she did her makeup, turning into the executive.

And I pulled on my new red outfit, smiling at her reaction.

At the banquet, gaziantep evi olan escort bayan she was that odd combination of proud and ashamed I had seen before. She introduced me as her “special friend,” and I hung on her arm and on her every word as a dutiful whore should. We made no attempt to hide our relationship.

It was fun, actually. Some of the men had brought wives, and a few women had husbands. Most, though, came single. The wives tended to giggle behind their hands, and whisper to each other. The husbands tended to stare openly. And many of the singles made approaches. I enjoyed it.

Back in the room, our little three-act play reached its climax. When we got behind closed doors I turned on her and said, “GO STAND IN THE CORNER!”

Her tears started almost immediately, but she went and stood where I had pointed.

I got the single chair from the dining room area of the suite and set it in the middle of the room.

I sat and beckoned her with a crooked finger.

She came, reluctantly, eyes downcast, finger in her mouth.

I yanked one of the tabs on her diaper and found her dirty again.

“Jesus Christ,” I snapped, and stood, grabbed her by the ear, and led her into the shower.

I hosed her down with cold water, standing well back. Me staying dressed was part of the, well, the script.

She was shivering as I toweled her down.

I grabbed her ear again and dragged her back to the front room. I sat on the chair, yanked her across my lap, and slapped her ass, hard enough to draw a yelp.

“You know what you did,” I said. SMACK!

“No, mommy,” she sort of wailed. SMACK!

“You were flirting,” I said. SMACK!

“No, mommy,” she said, sniffling, “I was just being nice.” SMACK!

“THAT is what you call nice?” SMACKKKKK!

“Mommyyyyyy,” she wailed. SMACKKKKKK!

She was crying now, seriously. With each slap to her small ass, she would shake her head, and tears and snot would fly.

Before I ended the spanking she was limp across my lap, just sort of whimpering.

Her ass was hot and red.

My palm stung.

All in all, a good end to the first day of a three-day stint that would earn me $2,500.

She was done, then, being a child. I went down on her, my tongue busy at her smooth pussy, finding her already wet and ready.

She was an interesting woman, sexually. Once we got past her child fantasy, she was a bit of a wildcat. And she was a squirter. She liked when I covered her with my mouth when she came and squirted.

Well, okay, I did too.

There’s a real feeling of accomplishment when you can make a woman cum like that.

And I made her squirt a dozen times, drinking her release every time.

Finally, she slept.

Vickie is attractive when she’s being a woman. She’s cute when she’s fantasizing about being a little girl. But she is NOT an attractive sleeper. Her mouth was open. She was drooling and blowing snot bubbles.

I thought she was adorable and liked watching her sleep.

Eventually, I slept too.

The next two days were like that. She would infantilize and become an adult and infantilize. Working her way through her fantasies.

The alarm woke me and so I woke her, with kisses, wet slobbery kisses as I knew she liked in the morning. Then I went down on her, kind of a wake-up orgasm before taking her into the shower.

She looked odd, dressed in her woman clothes, with real woman panties and a bra, as she put on her dark suit. I wondered, briefly, if she had any light-colored clothes.

Finally, she was dressed and had her little rollaway bag packed.

“The offer stands,” she said, looking up at me. I was still naked, the way she liked me.

“I’ll pay you enough that you can retire in 10 years,” she said. She was one of those women whose gaze switched from one eye to the other, making her own eyes kind of twitch slightly.

I kissed her, softly, and said, “when your fantasy becomes your reality it’s no longer a fantasy. You’d get tired of me if I was there all the time.”

She smiled and said, “I’d write a contract.”

I giggled and patted her head.

“I know you would, honey, but no,” I said, “now scat” and I turned her and slapped her ass lightly, propelling her toward the door.

She turned back and took a step.

She smiled up at me, handed me an envelope, sighed theatrically, and turned and left without another word.

I flopped onto the chair, opened a Coke from the honor bar, and opened the envelope she had given me. Now that was a pleasant surprise. There were 30 $100 bills plus a handwritten note – “Mandy, Please think about my offer. Vickie.” It was sealed with lip prints.

I dressed and headed home.

I like my job.

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