The (Fat and) Happy Hooker Ch. 06 – BDSM – Free Sex Story

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I like my days off too. I enjoy the domesticity of taking care of my apartment. My apartment is the second floor of one of those old Silver Baron’s mansions on Capitol Hill that had been converted sometime in the 1960s when such big, old, hard-to-maintain houses got to be just too much for a single family to handle. I had a kitchen, bathroom, living room, and bedroom, all good sized. It was a walk-up. There was an elevator that had been installed at some point, but I didn’t use it.

I enjoy doing my housework naked. I don’t know why, I just do. So I spent a pleasant morning sweeping and mopping, dusting, cleaning the shelves in my refrigerator, and even washing my windows. I giggled and waved at the old man across the street, standing in his window, naked too. He waved back.

My phone buzzed and when I looked at the screen it had a message from Steve, one of my regulars. “Nooner Holiday Inn Room 457.” I giggled and keyed in “30 minutes.”

“Well, fuck,” I said aloud, “so much for my day off.”

I liked Steve, it was easy money, so I took a very quick Shower and went downstairs and hopped into my little car. 28 minutes later, by my watch, I knocked on his door.

“Hello beautiful,” he greeted me, making me giggle. He was naked and obviously ready.

So I entered the room and wrapped him in an embrace.

“Have you been my good boy?” I asked, knowing what he needed.

“Mostly,” he said.

So I pushed him away, holding him at arm’s length.

“Mostly?” I asked.

“Wellllllllllllllll,” he said, standing there, eyes downcast, his foot making little arcs on the rug.

“What have you been doing?” I asked, my face serious now.

“I can’t help it,” he said, “it feels so good.”

“You’ve been touching yourself, haven’t you?” I said.

He looked down at the floor.

“Go stand in the corner,” I said, putting as much snap into my voice as I could.

So he went.

As with every motel room in the world, this one had a chair and a desk, but the chair had arms so it wouldn’t do. I looked around, but couldn’t see a good substitute.

I snapped my fingers and said, “Over here, Steve.”

He came, eyes downcast, head hanging.

“On your knees,” I said, “facing the bed.”

He complied.

“Hands right here,” I said, stretching his arms until they were flat on the bed, forcing him into an awkward position, supporting himself on his toes, his knees not quite reaching the floor.

“If you move,” I said, “the count starts over.”

When he didn’t reply I snapped, “DO YOU UNDERSTAND?!”

“Yes,” he said in a small, frightened voice.

“I think 50 is about right,” I said, “don’t you?”

“Yes,” he said in that same, small, frightened voice.

I looked around and found his clothes, folded neatly on a chair. I took his boxers and folded them into a small square.

“Open your mouth,” I said. When he refused I pinched his nose shut until he did as I said and then stuffed his mouth full of boxers.

“Now it’s 55,” I said and enjoyed his little moan.

I rolled the desk chair over and sat.

The spanking I administered took the best part of an hour. I know how to deliver a proper spanking. The first stroke, after I had caressed his Ass for a while, smiling at the goosebumps as I tickled, was barely a pat.

Each successive stroke involved taking time to caress until he relaxed then lifting my hand and giving him time to relax again as he anticipated. The stroke would be slightly harder than the last one.

He was crying by stroke 15, which was mostly drama. I wasn’t really striking that hard yet. By 25 his tears were legitimate. By 35 I was glad for the boxers stuffed into his mouth. He was wailing.

At 45 he broke and reached back to protect himself so I reached into my oversize bag and brought out the spool of carpenter’s twine I kept in there. It’s a nylon string, strong enough to string across a hundred feet or more without sagging. I bound his wrists behind him and then looped around his elbows, pulling them far enough back to completely immobilize him.

I checked his breathing. His mucus membranes would be badly swollen I figured, so I checked pretty closely. He was breathing okay so I picked up the count at 46.

At 55 I gave him time to rest, reminding him that it would be over except for him reaching back as he knew better than to do.

At 65, when I said it was over, he collapsed.

I reached under him and jacked him off quickly and efficiently, then pulled the strings on the bow knots that bound his wrists and elbows, stood, picked up the envelope laying on the dresser, said, “you have my number,” and left.

At home, I looked in the envelope and there were eight $100 bills. It’s funny really. My base rate of $500 includes unlimited vaginal and oral Sex. But “extras” are, well, extra, and spanking (giving) was a $250 premium whether or not he collected on the base service. The extra fifty bucks was a tip. As I say, easy money.

I called Maggie, my college roommate, and the girl who had introduced me to The Profession.

“Got anything on tonight?” I asked.

“Nah,” she said so we made a date for a Girl’s Night Out.

We went in her Cadillac CTS, a car that held fond memories for me. When she bought it, two years old at the time, she had brought it over and showed it to me we had the giggles playing with all of the gadgets. But when I asked how she could afford something like that on her salary she had told me of her “real job,” in The Profession. That had got me thinking and, well, here I am now.

The Student Union was a bar that was always fun for working girls on the make. College students were thick, and when a couple of plus-size, well, let’s just say 30-somethings, walked in we stood out among the skinny college girls.

As always, I couldn’t help but be amused. It was almost like you expected the music to stop. The line from a Dashiell Hammett book might have been “a hush fell over the room.

I went to the bar and Maggie scouted for a table. The bartender met me, his eyes drawn almost hypnotically, as most men’s are, to the full 8 inches of cleavage I was displaying. I got a pitcher of “whatever’s on tap,” two mugs, and found her at one of those hubcap-sized tables.

“Shall we give lessons?” I asked and she laughed and said, “sure.”

So I went over to the foosball table and laid two quarters on the edge of the table, signifying that we would challenge the winners.

The four guys who were playing finished their game and we took our places, side by side, and prepared to do something we’d been doing since we were college roommates, showing how this game should be played.

We took on all comers for the next couple of hours, drawing a small crowd to watch including, predictably, several college boys. We went through a second pitcher of beer too. As always happens, two of the alphas started hitting on us, something we both enjoyed.

When I felt a little jostle to my back I didn’t think much about it, but when the second one came, a bit harder, I held up my hand indicating “time out,” and turned. The girl behind me was scowling and I’m sure it was a very intimidating scowl for her cheerleading or gymnastics or track or whatever sport she excelled at, team.

I was unimpressed.

I didn’t hesitate.

I grabbed a handful of the T-shirt she was wearing and lifted, pulling her up to tiptoes.

“Now listen, toots,” I said, my nose about one inch from hers, “I have,” and I leaned back and looked her up and down, “about 175 pounds on you, about 15 years, and infinitely more meanness than you. Touch me one more fucking time and I will break your pretty nose.”

Her eyes got big. She was obviously used to being the alpha in her group.

“Up to you, honey,” I said, my voice low and calm, “if you want, we can go outside right fucking now, fair enough?”

I saw I had won when her shoulders sort of sagged.

I turned back to the game which we finished and then surrendered the table.

We finished our pitcher and headed out. We were regular enough that we knew about the strip shopping center parking lot across the alley from the bar, so we headed out the back door, past the bathrooms.

I was so surprised it didn’t really register on me what I was seeing at first but then the cheerleader I had confronted earlier stepped away from the group she was standing with and took a step toward me.

You don’t get into my Profession without being careful and one of the things I had done was take three different self-defense related courses, Korean Tae Kwan Do and Hapkido, and a generic “Self Defense” class taught by a grizzled old guy who had spent 27 years in the army. Eventually, I accepted the formal Oriental martial arts as good exercise, but paid attention to what Sergeant Dunham had taught me when it came to self-defense. He was fine with me learning formal kicks and strikes, but he reminded me, over and over, that you won the fight by NOT being formal or letting it become anything scripted. You hit first, you hit hard, and if you did it right, the fight was over before it actually became anything that could be called a “fight.”

I could see that she was going to tell me, probably in great detail, why she was kicking my Ass.

So I didn’t even break stride, didn’t say anything, gave her no warning at all when I swung my elbow, all of my 348 pounds behind it, and as I had promised, broke her nose.

I took a step back, happy when Maggie came up to stand shoulder to shoulder with me. I was confident I could take any of these girls, hell, any of the boys for that matter, one-on-one, but I ain’t Stephen Segal or Chuck Norris or Jack Reacher and I would lose against a half dozen.

But I didn’t need to. She was busy crying and holding her nose. The front of her blouse was already red.

“Get her to the Emergency Room,” I said, my voice a little shaky, not from fear but I was in the middle of quite an adrenaline rush. “That needs to be set. And you ALL probably want to think hard before you pick a fight with someone my size again.”

I stopped and waited a few seconds.

“Are we done here?” I asked, happy that my voice was steadying down.

Nobody said anything or, more important, moved, so I shouldered my way past them to Maggie’s CTS.

As we drove away I noticed her hand were shaking more than mine.

“Are you okay?” I asked.

“Honey,” she said, her voice shaky, “if we don’t get into a bed pretty goddam fast I’m going to explode.”

I laughed, a bit hysterically myself, and said, “well, my place is closer.”

I’m a VERY big girl, as I think I’ve made clear. Maggie’s a bit bigger still. When we got past my front door she had me pressed against the door and was kissing me, panting as if we had just run a marathon. Well, we HAD just come up a flight of stairs.

“I need,” she said, a little breathless, her fingers wrapped in my hair, “you to get your biggest, longest strapon and then fuck me until I’m too tired to cum anymore. Jesus, that was the most exciting thing I’ve done in YEARS!”

I laughed and said, “why do I have to do all the work?”

She grinned, her hooker grin (I have one too), and said, “because you got me this way.”

“You want me to undress you too?” I asked.

“Please,” she said, her voice suddenly soft.

So I started on unbuttoning her blouse, nuzzling and nipping at the soft skin I exposed as she hummed very softly.

As I’ve said, Maggie is bigger than I am, but it’s more than that. She got knocked up young, had a brief marriage, and now her son lives with her ex and his new family. She saw him a few times a year, but they were pretty much strangers.

But it had an interesting effect on her body.

For one thing, her tits are even bigger than my 52GGs. But they sag worse than mine. She’s one of those women who, when her tits fell, actually left her nipples under them. I think they’re sexy, always have.

She’s a bit older than me too. She took a couple of years off after the baby. Fucked around and tried to lose weight leaving her with an absolutely amazing set of stretch marks. And a belly apron that was truly a fat girl’s natural modesty.

I got her blouse and bra off, played with tits and fat, and then grinned as I got to my knees to get her shoes and socks off, her jeans unbuttoned and unzipped, and then her jeans and a pair of granny panties that would have made a passable parachute for a fairly good-sized animal. I kissed every square inch of skin I exposed.

The scent of her arousal was strong in the air by the time I had her naked.

“Up on the bed, bitch,” I said, turning to my toy box.

She giggled and with a dexterity absolutely amazing in someone of her size, hopped up onto the bed, laid back, and said, “fuck me until I faint, Sammee.”

She had asked for the “biggest strapon,” so I showed it to her. I had bought the thing because I just couldn’t resist. It’s a full three inches in diameter, a perfect replica of an erection with distinct veins, like a cock redrawn at about 250% scale. The damn thing is a foot and a half long.

Her eyes got big, but she was smiling.

She watched as I worked the harness on over my own big Ass, and tightened things up The big dildo bobbed and gave me interesting little sensations as I moved up into position.

“Spread those legs,” I said, flashing my best feral grin.

She pulled her legs up until her knees touched her nipples then reached down and opened herself up. She stretched open nicely but as I moved forward the dildo was clearly too big for even her well-used Pussy.

Her natural lubricant was running now, thick and white, almost like a man’s semen. As I watched it pumped out, and ran down the long crack of her Ass. She twitched a little when I touched her with the end of the strapon.

“I don’t think I can take that,” she said.

I laughed and thrust, hard, burying it into her.

She grabbed a pillow, covered her face, and screamed into it.

I pushed harder until our bellies were touching as she screamed again.

She lifted the pillow and met my eyes, her face a strange rictus of pain and pleasure.

Her fingers found my nipples then and she twisted hard enough to make me yell in my turn.

“Come on, bitch,” she said, her voice a strange mixture of laughing and crying, “TEAR ME UP!”

I laughed myself, then and said, “tear them off if you can,” and started fucking her as hard as I could. Each thrust I would pull out almost all the way and then slam back into her, our bellies making an audible slapping sound that got wetter as I went on with a combination of sweat and her mucus being pumped and smeared.

It was my turn to yell as she took me at my word, her fingers digging into my tits, yanking on them hard enough that I knew there would be matching little bruises.

We kept doing that, not making Love, hell, not even fucking, kind of sexually torturing each other, until I just collapsed on her.

I was exhausted, sweaty, panting. My nose was running and I couldn’t seem to catch my breath. I have no idea how many times I came, or she came, but I know it as several.

I was making her carry my full weight, and it felt like we were absorbing each other.

“I Love you,” she managed before she started snoring.

I rolled off of her, afraid I might kill her if I went to sleep, nuzzled against one of those immense tits, and drifted off myself.

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