The (fat And) Happy Hooer

"Oh God," he moaned as my fingers lingered in the stickiness of his shorts.

I smiled and said, "Thank you."

His eyes got big again and he said, "For what?"

I kissed him, just a soft quick kiss, and said "You just paid the fat girl a wonderful compliment."

"I'm sorry," he said.

"Noooo," I said, holding his hands, "No, Benjamin, no, it was a compliment and I'm flattered."

He was looking crestfallen so I moved closer, my belly touching him, my palms very light on his cheeks, and made him meet my eyes.

"Do you want me?" I asked. I was wondering, if we're being honest here, what his answer would be. I was pretty sure I knew but, well, he was young and it was a weird situation.

"God yes," he said, making me smile.

"Show me," I said, moving fractionally closer to him but stopping short of a kiss. One of the things Will Smith had right in that movie where he was the dating guru, I don't remember the name, was that it was important for the other person to cover that last 10 percent of the distance and initiate the kiss. It's a trick every hooker knows.

The first kiss was about what you'd expect from a just-turned-18-year-old who had cum in his tidy whities at the first touch. It was awkward, full of energy, and very low on technique.

But not a bad first kiss at all.

Once it was initiated I held it, my palms on his cheeks.

His hands were tentative, lightly brushing my arms and then my waist, getting slightly more confident as I held the kiss.

I could feel the instant he realized this was real, that I wouldn't suddenly say "no." He stepped in, pressing his body against mine, his hands reaching around now, pressing my back as far around as he could reach, his fingers starting to dig in.

I arched my back, pressing into him, meeting his interest with my own.

I held the kiss.

Finally, I broke the kiss, pushing him to arm's length, smiling, and shrugged out of the floor-length, filmy overrobe.

He sort of froze so I smiled, brushed my lips across his, and lifted his hands to my breasts.

"They're yours now," I said, giggling a little at the way his eyes got big, "go ahead, Benjamin," being sure to use his full name, "play with them. I enjoy it."

That stopped him. "What do you mean?" he asked.

I smiled, my best winning smile, the one I practice in the mirror, and said, "Happy Birthday, Benjamin. I am your gift from your mother and father."

His eyes got comically big. "What, how, ummmm," he got out before winding down.

I kissed him, this time it was me kissing him, and said, "Benjamin, I'm a whore. A hooker. A prostitute. A practitioner of the world's oldest profession. Call me what you will, I have made a good living exchanging sex for money."

I stopped, giving him a minute to process.

"Your mother and your father want you to know about sex, about women, about how to please a woman, and how to get a woman to please you. They know I'm here and what I hope we'll be doing over the weekend. They'll know when I start sharing your bed if you want me to. There are no secrets, Benjamin, so you need to decide if you want that," and I kissed him again, giving him another minute to process.

He started to say something but I put my finger to his lips.

"Let me finish," I said. Hell, this was a little speech I had been working on so I figured I might as well play it out.

"If you want me, there are only two conditions, Benjamin, no children, and no animals. Beyond that, I will never say 'no' to you," I went on. "But think about it, worst case, you're in for a memorable weekend, that I will promise."

He reached for me and I did nothing to stop him.

He was tentative at first, barely touching, watching, a smile growing on his face as my areolas tightened and my nipples turned into hard cones.

"Kiss me, Benjamin," I said.

He was starting to relax, and that second kiss was better although only marginally. He was still short on technique, but he was full of energy and anticipation.

I kissed back, a good kiss if I do say so myself, and reached down and found the hem of his T-shirt and peeled it off of him. I took my time, finding those sensitive spots every hooker knows. His nipples were hard little cones and I pinched them, giggling when he twitched.

I stood with him, then, and finished what I had started, getting his tidy whities off of him.

Apparently, short thick dicks were genetic in his family. He looked a lot like Jacob down there. Circumcised, of course, with thick, almost black, curly pubic hair. He was soft now so only a couple of inches of dick peeked out from the thatch of hair. Like his daddy, his balls were big, hanging in a loose scrotum. I lifted his scrotum and got the first signs of life from his dick.

"Ummm," I said, "this might be a good time to unlock the belt."

His fingers were trembling, I was pleased to note, as he tried to fit the little key into the brass lock that held me in the chastity belt.

The belt off I went to the refrigerator and got two beers.

"Come here," I said, sitting on the couch.

He came and sat next to me.

"You need to get used to being naked with me," I said, "or else we'll never be able to hold a conversation because, sweetcheeks, I consider clothes to be pretty optional around the house."

"Oh, I definitely think I could get used to this," he said, brushing his hand across my breasts.

I smiled and ran my hand down his arm. "Good," I said, "because I'm looking forward to teaching you."

"Can I," he started but I stopped him with a finger to his lips.

"I told you, Benjamin," I said, "no children, no animals. Outside of that, I won't say 'no' to you."

I could see that he had no hope of stopping the smile on his face, it was a smile I had seen on clients' faces before. He bent forward and I knew, with no doubt at all, what he wanted. Men, whether 18 or 78 are, when you get down to it, pretty predictable.

I lifted my breast, using my thumb and forefinger to work my nipple, and said, "Is this what you want, Benjamin?"

"Yes," he said bending toward it.

"Here, baby," I said, "let's do it right."

I scooted away from him, to the end of the couch, touching the armrest, and then guided him with my hands and told him what I wanted until he was laying on his back, his head supported in the crook of my arm. I used my hand to brush my nipple, hard with my own excitement, across his lips until he took it into his mouth.

I giggled as, once again, I realized how little he really knew.

Oh, he had plenty of energy, he just didn't know how to do it properly. His lips pursed and he took my nipple and started sucking. I figured he might have made second base with some girl at school, but no farther.

"Easy, baby," I said, "Open your mouth."

His eyes were closed but he did as I asked. I gently worked my nipple and areola into his mouth. "Now, take a little more, Benjamin," and I felt him suck gently, his lips working.

"Use your tongue, sweetheart," I said, brushing a few stray hairs back from his forehead.

I could feel that instant when instinct kicked in. He was still sucking gently, fully latched on. And his tongue started massaging my nipple and areola, the erectile tissue fully engorged now, against the roof of his mouth.

"Mmmmmmmmm," I hummed, tickling his forehead with my fingertips, "that's right baby."

I felt him relax and truly start nursing, his eyes closed, and I felt the rush deep in my belly as he was getting to me.

He jerked, well, more like twitched, when I touched his dick, still soft.

"Relax, Benjamin," I said in my best soft calming voice.

I brushed his forehead lightly with my fingertips and then slowly, fingertips barely brushing, moved my hand down again. He wasn't hard but he was, as they might put it in one of those stupid ninety-nine-cent romance novels, turgid. I was gentle, just holding him, wanting him to get used to us as a couple without modesty or inhibition.

I used my finger to break his latch on my nipple.

"Do I please you, Benjamin?" I asked.

"God, yes," he said, his eyes big.

"Good," I said, "you need to tell me that, honey. A woman needs the words."

He kissed my breast then, not reaching for the nipple, just kissing the soft skin at the top where stretch marks had developed from their weight, looked up, met my eyes, and in his first truly adult sentence said, "You please me very much, Sammee."

It surprised me how much that got to me. My damn eyes were overflowing when I bent into an uncomfortable position and kissed him. His technique was still pretty weak and the awkward position didn't help, but it got to me.

I pushed him away, very gently, not wanting him to think I didn't like, very much, what he was doing.

"Okay, sweety," I said, deliberately wanting to get him used to pet names and endearments, "easy now." I stood before him, naked, and smiled.

"Come here, honey," I said. When he came I took his hand and led him into the bedroom.

"I'll take care of this for you," I said, brushing my fingertips across his erection, like his daddy's thick and not very long although, if I'm being honest here, a little bigger in both dimensions than Jacob, "but it will be better for both of us if we wait."

"I trust your judgment," he said, the second truly adult thing he had said this weekend.

"Okay, sweety," I said, kissing him, a quick but inviting kiss before I crawled up onto the bed and patted the sheet in invitation.

He joined me and waited, understanding that there was no hurry.

I took his hand and laid it on my breast.

"What do you call it?" I asked.

He smiled and giggled, an oddly childish sound, and said, "ummmmm, your boob?"

I smiled.

"Yes, baby, my boob. Or my breast or my tit. My Jug. My hooter or my knocker or a headlight or a fun bag or any of a hundred different things you men call them," I said, being sure to refer to him as a "man."

"And this?" I asked, guiding his hand to my nipple, hard with my own growing excitement, standing on the tight cone of my areola.

He surprised me by bending and kissing the line where my areola rose from the pale soft skin of my breast, looking up at me, and with a big smile saying, "My new favorite thing."

I giggled.

"Okay, touche'," I said.

"This," I said, lightly tracing my areola with my fingertip, "is the areola and I don't know any slang words for it. These," and I touched the distinct love bumps on my areola, "are called love bumps although they are really Montgomery's Glands. And this," and I brushed the tip of my nipple," is my nipple.

"And my favorite thing," he said again, and bent to take my nipple, areola, and some more breast tissue in his mouth and begin nursing, suckling like a hungry baby. I smiled and stroked his hair for a little while before I used my finger to break his latch and free my nipple.

"All you want, Benjamin," I said, but lessons first.

"Yes Teacher," he said and we giggled together.

"My boobs are sensitive, and it feels good when you do that," I said then giggled and caught his hair when he started moving to my nipple again, "BUT," I said, "there are other places that feel good on a woman too. They're called erogenous zones. Now do you want to learn about them or do you want to just fuck?" I finished, deliberately using crude language.

That made his eyes go wide.

"Benjamin, I won't say 'no' to you, ever," I said, holding his eyes, "but what I'm trying to do is teach you how to make it better for both of us. So it's up to you," I finished and flopped onto my back and spread my legs.

And he said his third adult thing, this time a full sentence, heartfelt. "Sammee," he said, rolling up onto his elbow and very lightly brushing hair away from my forehead, "I apologize. Accept the apology of a known asshole and please," and he bent forward and kissed me very softly, "don't give up on me. I do want to learn."

So I laid my head back and posed with my hand behind my head, looking rather artful I thought.

"Slowly, gently, a light touch, tickle down the inside of my arm," I said, softly.

He did as I asked but missed those nerve ganglia that work so well for me.

"Again, sugar," I said, "you'll know when you find the spot."

On the fifth try, he found it. My breath caught and it took pretty much all of my concentration not to squirm. I could feel my skin tightening as goosebumps formed and I noticed his slight intake of breath as he saw what he was doing to me.

"You like that?" he asked, surprising me since my concentration had been so focused on what he was doing. His voice was soft and I liked it.

"Oh yes, baby," I said, unable to stop a sharp little gasp as his fingertip crossed the smooth skin of my armpit.

He found the ganglia deep in my armpit and pressed, sending a shock down my arm and making me jump.

"Shall I stop?" he asked, his voice low and insistent.

"No," I said, and added, "Please don't."

He did the thing again, starting at my wrist and then slowly down my inner arm. He lingered at my armpit, making my nipples almost jump they were so hard. Then, without direction, he followed those nerves around the base of my breast where it met my ribs, this time finding enough nerve endings to make me squirm.

That seemed to break my spell and I caught his hand again.

"My navel or my belly button," I said, guiding his fingertip to the deep crease that led to the aforementioned navel.

I giggled when he probed and said a soft, "Oww," when he found the bottom and pressed a little too hard.

"Easy baby," I said, giggling a little, "that's me under there."

I caught his hand and guided it further down, to grasp the heavy soft roll of that lowest layer of belly fat, the one that hung far enough to give me a bit of a belly apron, you know, a fat girl's natural modesty.

"My apron," I said, covering his hand with mine and giving it a shake, making it jiggle like that bowl full of jelly of

The Night Before Christmas

fame.

"Go ahead, Benjamin," I said in my best hooker's please-fuck-me voice, "play with it. I'm not ashamed of it."

"Kiss it, honey," I said, "show me you like it."

So he squirmed around and started kissing my belly. I couldn't help the giggle when his tongue probed my belly button, and then as he used his fingers to spread that deep crease and work his tongue, warm and wet, all the way to the bottom. This time I didn't have him stop.

Then he was at that last roll where I'm so damn sensitive. I don't know why, but I am, especially at the bottom of that roll where the chub rub of constant contact has left the skin dark and leathery but oddly hypersensitive.

I did stop him, my fingers tangling in his hair and gently pulling him away.

"This," I said, guiding his hand again, this time to my mons, perfectly smooth like the rest of me below my neck, "is my

Mons Veneris

, that Latin for the Mound of Venus. Just call it my mons."

"Can I ask you something?" he asked.

"You can ask me anything, Benjamin, and I will never lie or even try to shade the truth with you," I said, holding his eyes with mine.

"Why are you so smooth everywhere?" he asked, his fingers lightly tickling the current lesson.

I giggled and told the truth.

"It was the style when I was a working girl," I said, "and I couldn't shave because I just can't really reach everywhere and I tend to get rashy when I do, and I hated the pain of waxing. So I put in six uncomfortable Wednesdays with chemicals and lasers and now, well, what you see is what you get."

I smiled and kissed him. "I hope you like it," I said.

"I love it," he said, touching some more.

I guided his fingers lower, pressing the pad of fat right at the juncture of my legs. I don't have a FUPA, you know, that Fat Upper Pussy Area, but I'm a big girl and big down there too.

"This," I said, pressing gently, "is my clitoral hood, and this," and I pushed his finger deeper, "is my clitoris." I pressed until his fingertip found it, sending that little electric charge up my body. "It's called many things, Benjamin. The little man in the boat. The button. The spot. It's kind of my equivalent of this," and I touched the head of his erection, gently running the top of my finger around the corona, "so be gentle but play with it."

"That's nice," I said, as his finger started making little circles around my clitoris, stimulating me.

I caught my breath and then caught his hand.

"Easy, baby," I said and guided his hand lower.

"This is my labia, my outer lips," I said, using his fingertips to gently probe, "feel how wet, how slick I am?"

"Yes," he said, his voice shaky, a little tremble in it.

"I have mucus membranes down there," I said, "and in my belly there are a couple of glands, the Bartholin's and Skene's glands, that make me slick like this. It's so we can make love without either of us getting hurt."

"Go ahead," I said, "touch and play."

He did then, his fingers an odd combination of gentle and awkward as he learned.

I caught his hand then, pulling him away.

"Sit back, honey," I said, pushing him away so he was on his knees.

"These," I said, using my fingertips to open myself, showing him, "are my inner lips. They're very sensitive, very delicate honey, so be careful when you touch."

He didn't move and I giggled.

"Go ahead and touch, honey," I said.

His fingertips barely brushed against me and I felt that little jolt I always did when touched like that.

"Okay, Benjamin," I said, giggling and catching his hand, "I think that's enough lesson for tonight, don't you?"

"What?" he started but I pulled him down into a kiss.

"Take what you need," I said, pulling him down onto me.

His eyes were big as I reached down and took his not-very-long but very-thick erection, guiding him.

When he touched I grasped his hips in my hands, holding him, stopping him from entering me.

"Remember what I said," I said.

He looked blank and I giggled again.

"Say it," I said.

"You please me," he said.

I released his hip with my right hand and pulled him down for a kiss.

"Say it all," I said.

"I love you," he said.

I pulled him to me, accepting him.

"Do I please you?" I asked.

"Yes," he said, holding still, seeming to be almost afraid to move.

"Do you love me?" I asked.

"Yes," he said, still not moving.

"Say it," I said.

"I love you," he said, and I rocked my hips, encouraging him.

And he came.

"I'm," he started, I was sure starting to say something silly like "I'm sorry," but I pulled him into a kiss.

"Thank you," I said, breaking the kiss, "for your beautiful gift."

And I considered our first lesson complete.