The (Fat and) Happy Hooker Ch. 09

I spent the weekend with Maggie. She had a Friday night client but when she put him on the plane Saturday morning she headed straight over to the house.

The first thing was business, so I dumped the contact list from my phone onto hers and started explaining all of my client's little foibles and quirks. She was fascinated by the infantilization of Vickie, the submission of Randall, the desire to spank of Steve, and so on down the list. Mostly it was a matter of explaining the little code I had worked out and put in the comments section of each entry.

"I'll send you 40 percent of everything I make off of your clients," she said and I raised my hand in negation.

"No, Maggie," I said, "this is my gift to you. I'm retiring. You introduced me to The Profession and asked for nothing. Now accept this as partial payment for all that you did for me and all that you mean to me."

She smiled and crooked her finger, beckoning me.

"Come here bitch," she said with a giggle.

I went to her and she wrapped me in an embrace, kissed me, and whispered, "today I do all of the work."

As she undressed me I had an image and broke out laughing.

"What?" she asked, looking up from where she was on her knees getting my shoes and socks off.

"I was just thinking," I said, "if someone had a camera we could title this movie something like '600 Pounds on the Hoof,' or something like that."

She turned serious, suddenly.

"Did you ever do any work in porn, Sammee?" she asked.

"Nope," I said, "nobody ever asked."

"It was fun," she said, "in a weird way but not like you probably think."

"How come?" I asked.

"Oh, it was interesting," she said, "the lights and the camera and the director, you know," and she giggled, "directing. But it wasn't really sexual. I had to fake it as he told me, you know, 'getting closer now, cry out,' but it was pure acting. The script called for me to, you know, 'squirt,' and that was special effects, a water balloon, and my very educated muscles."

I giggled and then it went into a full-on laugh.

We made love then, and it was making love, not just fucking, well, not just getting each other off. Then we cleaned up and went shopping.

The thing is, neither of us had much of an idea of what would be appropriate. We knew how to look like whores. But how do you look like a tutor, or a nanny, or a housekeeper, or whatever the fuck my new role was?

So we went to Penney's. We figured that was about as middle-class a place as we could find.

We looked at the models, and at the women shopping, and it hit me, well, us, that there was damn little in this store that would fit me.

I got on Google maps and found a Lane Bryant store at the outlet mall and we headed over there. We were, well, let's say, out of place there. Oh, there were plenty of fat women but we stood out. Our bare midriffs and uplift bras and skin-tight shorts made us look like, well, okay, hookers.

We spent two hours in Lane Bryant and another two hours in a store called Maurice's. I left with a whole new wardrobe, all purchased, of course, on my new credit card. We did lunch then, a classic three-martini lunch, and went back to my apartment where we got naked and spent the rest of the afternoon and deep into the night with a pot pipe, a gallon of Rocky Road, and a case of beer, trading orgasms. We nursed on each other's tits and worked our way through my toy box.

She particularly liked my pregnancy toy. I used the thin probe to ease the end of the little pink balloon past her cervix into her uterus while she held herself open, her arms wrapped around the backs of her thighs, pulling her legs back until her knees touched her nipples, her thighs squeezed belly fat out, and her fingers pulled herself open. She grunted once as the probe penetrated and then relaxed.

"Now for the good part," I said, and started pumping the little inflator bulb, exactly like that thing the doctor uses to check your blood pressure.

"Oh my," she said as the pressure in her uterus built. I was kissing her as I pumped, telling her she was beautiful.

"Oh MYYYYYY," she said after a couple of minutes, "Sammeeeeeee, where can I get me one of these."

I giggled and said, "ask Samuel Long to hook you up when he calls for an appointment. He's an ob-gyn and he gave this to me."

I would let her rest for a few minutes, until her breathing was slow and easy, and then give five more pumps. Within an hour she looked pregnant. Not just a baby bump either, hugely pregnant, ready to deliver. When she stood you expected her water to break.

When it was her turn she rolled me onto my back and sat on my thighs, ponderous with that huge belly, and started mauling my tits. She knew just how much pressure to apply. Just how to twist to the edge of pain and suddenly delve into that area and back to pleasure. She squeezed and pinched and twisted and when I came, my pussy untouched, she giggled and called me a tit whore.

It was early morning before we went to sleep, sweaty, exhausted, and very VERY satisfied.

When I woke she was gone and I laughed when I saw the envelope she had left on the bedside table. I opened it and there was a hundred-dollar bill and a note. "Sammee, I love you, you know that. I'll keep your clients happy. If you come back to The Profession I'll be ready to share my list. But I think you won't. You struck it rich, girl. EVERY whore's fantasy. So enjoy, and frame this bill as your last payment in The Profession. Maggie."

And damn if I didn't cry for a while after reading that.

The rest of Sunday I tidied up the apartment. I made sure any perishable stuff was out of the cabinets and refrigerator. I vacuumed and even washed the baseboards down. I thought of movies I'd seen where the family was getting the place ready when they came back after an extended absence. "On Golden Pond," one of my favorite movies, was in my mind as I flipped sheets over my couch.

I went to the post office and changed my address. Did the same with my driver's license. Then I spent an hour on the computer changing my address on a variety of sites from which I ordered things from time to time. Amazon, of course, but some other online retailers as well. It was getting dark when I looked around the apartment and decided I had done everything I could think of to do. So I went to Appleby's for dinner. I wasn't about to mess up my spotless kitchen.

I was watching the big television over the bar, some men running up and down a basketball court, a sport in which I have no interest, contemplating what would happen tomorrow, when a voice pulled me back to the here and now.

"Did you get stood up too?" he asked.

"Excuse me?" I replied, having no idea what he meant.

"My date didn't show," he said, "and I thought maybe you'd like some company."

I looked him up and down. God, I think if you looked in the dictionary under "nerd" you would have seen his picture. He was short with thick glasses and the image of Johnny Galecki's Leonard Hofsteader from "Big Bang Theory" jumped into my mind.

I thought for a second and then giggled and said, "sure, have a seat."

And again that image of Leonard flashed when he sat and grinned at me.

"I'm Steve," he said, reaching across the table and offering his hand.

I giggled again, accepted his hand, and said, "Samantha, call me Sammee."

He was so obviously inexperienced I just wanted to take him home and cuddle him. I guessed him at 19 although they did serve him the beer he ordered so maybe I was a little shy on that or maybe he had a fake ID.

He wanted to talk, obviously, and, well, I'm really good at listening.

It turned out he had finally got his courage up and asked his dream girl out (more images of "Big Bang Theory" flashing through my mind). She had said "yes," but then hadn't shown up.

It was an interesting evening and part of my mind was having a discussion with itself.

"This isn't all that different from the 18-year-old boy you're going to be teaching," I said to myself.

"So look at it as practice," I replied.

So I did.

As dinner progressed, a double Whisky Bacon Burger and Oriental Chicken Salad for me, a Quesadilla Burger for him, with a pitcher of beer to share, I decided that my last night as a hooker was going to be the only freebie I had ever given, and this young man was going to have his world rocked.

In a way, I was on kind of new ground here. I was used to being the obvious hooker and first meetings being a straightforward negotiation. It had been quite a while since I had trawled conventions. My business was almost exclusively repeats and referrals for the past six years. But with Steve, I had to play the reluctant fat girl.

We finished dinner and he was SO cute when he stammered, asking if I'd like to "have a drink or something."

I said yes and we called an Uber. The place he suggested was new to me, and turned out to be interesting. It was kind of a nerd's version of a roadhouse. Rather than cowboys and mechanical bulls and dart boards there was a long bar, a chalked list of microbrew beer available at that time, and a rack of video games across the long wall that made me think of movies I had seen when there had been whole stores devoted to those things. Names like Space Invaders and Asteroids and something called Galaga were on display, the squeaky door sound of Pac-Man chasing dots, and a half dozen of them had young men, virtual clones of my night's date, standing in front of them.

As I looked around I saw three other women, well, girls, I was clearly the oldest person in the room. We ordered beers and found a table. There was a small open floor, something I took to be a dance floor, and the background music in the building, much softer than any other place I frequented, was playing something that sounded modern and slow but I couldn't have named the song or the artist.

We chatted a little more as I looked around, taking the place in.

He was SO damn cute. You could almost see him working up his courage. Finally, he stood, moved around the table, and held out his hand. "May I have this dance?" he asked and I couldn't help but giggle at his formality. But I stood and let him lead me to the little floor.

We were the only couple, but I didn't mind. Hell, I'm a good dancer. I'd better be. I'd done the Arthur Murray thing and worked with private teachers. I figured it was part of my toolbox.

But tonight I needed to be the awkward fat girl so I stood, awkward, letting him take the lead.

"I don't get many chances to dance," I said, "so you'll need to show me."

He smiled and said one of the most adult and sophisticated things he said all that night.

"Come on," he said, "a beautiful woman who doesn't get asked to dance? Don't bullshit a bullshitter, Sammee."

I put on my best simper face and said, "thank you for the flattery."

Well, you can cut a few yards of that conversation yourself. I won't try to replicate it here.

We stayed there for a couple of hours. We danced a few times, played the silly video games, and mostly talked. He was a Junior at one of the local colleges, a history major who wanted to be a teacher. As midnight loomed, and yes, I was a bit drunk by then myself, I said, trying my best to look awkward and sort of defensive, "ummmmmm, would you like to come up and see my etchings?"

His eyes got big.

"It's okay, Steve," I said when he hesitated as I knew he would, putting my best hurt look on, "I understand. Thanks for being nice to the fat girl."

When I started to stand he covered my hands with his, holding me there. Oh, I could have kept moving but this was part of the act.

"Sammee," he said, and there was pleading in his eyes, "I'm sorry. I'm just, well, shocked. I don't get invited to beautiful girls' apartments."

"EVER!" he added.

I put on my best wan smile.

"It's okay, Steve, I understand," I said, thinking it would make it better for him to break through my self-image issues.

"Sammee," he said, and there was pleading in his eyes now, "ask me again, please."

I smiled and said, doing my best Mae West voice, "Why don't you come up and see me sometime?"

He jumped to his feet and said, "yes, NOW!"

I giggled at that and took his offered hand and stood.

He was nervous on the Uber ride to my apartment and I didn't try to ease it.

After the walk-up, I lied and told him the elevator was broken (the "Big Bang Theory" in my mind again, wondering if he was seeing that comparison too), and we were both a little breathless. Me because I was lugging a lot of weight up the steps, him because he's a nerd and not in good condition.

Inside, we stood, facing each other for a long moment before I decided it was time to start this young man's lesson.

I took the step that separated us, laid my palms on his cheeks, and then gave him my absolute best, five-star, I-am-going-to-rock-your-world kiss. It was a long, lingering kiss and I pressed against him, making him lean into me or have to take a step back. He leaned.

I was in one of my new outfits, practicing my new look I guess. When I broke the kiss, leaving us both a little breathless, I reached over and undid the top button of his shirt. When he didn't move I took his hand in mind and moved it to the top button of my blouse.

"Now you, Steve," I said, trying for my best breathless voice.

His fingers trembled a bit but he managed to get the button unbuttoned.

I did the palms-to-the-cheeks thing again and kissed him, a gentle kiss full of invitation. "Now kiss the skin you exposed," I said.

He smiled like a little boy on Christmas morning and bent to brush his lips against the small section of cleavage now on display.

He couldn't see as I rolled my eyes.

I dug my fingers into his curly hair and pulled him away gently but firmly. "No, honey," I said, "kiss," and I kissed his cheek, thoroughly, my lips dragging across the skin, my tongue lightly tracing, "like this."

I'll say this, he was a quick study. His next kiss was good, his lips on the tops of my breasts, the small triangle he had exposed, making me tingle a bit.

It took us a half hour to get undressed, well, to undress each other. When he had undone the second button of my nice middle-class blouse and then moved his fingers to a third I spatted his hand.

"No, Steve," I said, "take your time. Pay attention to what I'm teaching you and you'll never be stood up again, I promise you."

"Teaching?" he asked.

I smiled and said, "yes, Steve, teaching, now pay attention."

And he did.

By the time he got the blouse off, he was getting better.

I grabbed the second roll of fat, the one below my breasts, and said, "Steve, I'm a fat girl. I'm not ashamed of it. I won't break and I won't get mad. Touch. Play with it. Enjoy me as I'm enjoying you."

He started then, enjoying my body, no longer afraid that every touch would break me or be too far or something. He would kiss and squeeze and play with the rolls of my body. I had his shirt off by then too and my own fingers were busy.

I turned and he got my bra unhooked, no small feat actually, at my size my bras are, well, heavy-duty, and there are six hooks on a four-inch wide strap.

He stared at my breasts for a long moment before touching them, very tentatively, just his fingertips.

So I lifted my right breast, deliberately squeezing it, distending my nipple with the pressure I was applying.

"They won't break either. baby," I said.

He was still too tentative so I dropped to my knees, figuring it was time to move to the bed and get things horizontal.

I lifted his right foot, forcing him to grab my shoulders for balance, and untied the shoe and peeled off the sock. Then I did the same with the left. Still on my knees, I undid his belt, unbuttoned and unzipped his jeans, and pulled his jeans and boxers down as one unit.

He was erect, of course, and I kissed it, just a light kiss, full of promise I hoped.

Then I stood.

"Your turn, baby," I said.

He smiled and dropped to his knees, as I had done. He got my loafer-style shoes off and the knee-high hose I was wearing, before starting on my jeans. It felt funny, actually. After a decade of wearing nothing that wasn't skin-tight, the momjeans I had purchased the day before felt baggy and almost fell off. The panties, big granny panties, replacing the high-leg French cut that I had worn for over a decade, were next.

"Wait," I said as he started just pulling the panties down, "take your time, do it right." I began at the waistband, rolling them down showing him what I wanted.

He caught on and kept rolling them down. By the time he got past the big roll of my belly apron, they were a tight band.

"That's right, baby," I said, smiling down at him, "hobble me and then I can't get away, can I?"

He smiled up at me, an interesting smile, part shy, part almost feral, and rolled the band down to my knees.

He buried his face in the deep crease of my navel and his hands squeezed my ass, pulling me to him. I drew a sharp breath.

"Is this what you want?" He asked, leaning back and looking up at me over the rolls of my belly.

I smiled down at him then and said, "wrong question, Steve."

His smile changed to a quizzical look.

"And what is the right question?" he asked.

I grinned, my own feral grin, and said, "what do YOU want?"

He grinned back, used both hands to lift my belly out of the way, and found my mons with his mouth. The panties prevented me from parting my legs for him, but he didn't mind. His tongue became a living thing, and it turned out he was pretty darn good with it.

"Oh, honey," I managed, "that's nice."

He kept at me and I made no effort to control myself. That delightful pressure in my belly built until it overflowed and he pressed harder, deeper between my legs as I came.

And he kept at me, sucking and licking as I came a second time.

And he kept at me, sucking and licking, as my body built up to another climax, until I was trembling and now I was straining, pushing, seeking my release.

And he stopped.

He leaned back and looked up at me, his face shiny with my nectar and his hair soaked, hanging lank.

"Do I please you?" he asked.

"Oh my, yes," I said.

He rolled the panties the rest of the way down and I stepped out of them. He stood and I led him to the bed. I pulled the quilt and blanket down and climbed in, not something I do gracefully at my size.

He was grinning as he crawled onto the bed and got his knees between mine.

"Now," I said, "use your control, baby. Make sure I make it at least twice before you take your pleasure."

He grinned, slipped inside of me, and began nuzzling my neck. He was actually pretty good, but I still had to talk him through it, and remind him to slow down.

There are tricks you learn, though, and I used them. At one point, when it looked like his control was going to fail I used my thumbs to jab him in the ribs making him jump so hard in that natural reflex when that happens that he slipped out. I pulled him down onto me, but not into me, and held him there.

"Easy, baby," I said, "you have me close, don't ruin it now. Relax for a bit," all the while my hands were covering his back, my fingertips pinching skin here and there, and my lips were right at his ear so he could feel the words being formed as I breathed them.

When the tension left his body I moved my hips in that way I had practiced over and over and he was back inside of me.

I hadn't been lying. He had me close.

"Now, baby," I breathed, my voice thick with my own arousal, "take me over the top."

He did it well.

His rhythm was slow and his mouth was at my throat and my breasts and when he latched on, suckling like a hungry baby, I came.

"YESSS," I cried, "Yes, yes," my hips bucking a little to meet his, "yes YES, HARDER NOW!"

He pulled out slowly until he almost slipped completely out and then suddenly, unexpectedly, slammed into me, our pubic arches meeting with an audible SMACK and an audible splashing sound I was so wet.