Learning the Ropes

by Jacqueline Jillinghoff

Copyright© 2011 by Jacqueline Jillinghoff

Sex Story: Spring. The Newsboy finally gives up his virginity to a woman twice his age. He’s eager for a second encounter, but his lover turns out to be more demanding than he expects.

Caution: This Sex Story contains strong sexual content, including mt/Fa   Light Bond   First   Big Breasts   .

Top of Form

Bottom of Form

"Take off your clothes."

Mindlessly, I did as I was told. In a moment I stood naked beside the bed, open for inspection. My dick, which neither of us had touched, was solid as a post. It hovered over the mattress, pointing at her as she lay on her back, her head resting on a stack of pillows. She had dark, closely cropped hair, and brown eyes that shined as she gazed at my cock and balls. I could almost hear her salivate.

"You're very handsome," she said.

She was flattering me. I wasn't at all handsome, but any expression of modesty would have been stupid at this point. This was a teen dream: a woman twice my age, wearing nothing but a short blue robe, just told me to strip. The smart thing to do was go along.

She undid her belt. The robe fell open to one side, and I was looking at half her nude body, an unbroken block of flesh from the hollow above the collarbone to her toes, which she pointed toward the foot of the bed, extending her slender leg. The breast was small, flattish even, but with a long, blunt nipple. The side of the robe that stayed in place cut the black triangle of her pubic hair precisely in half.

With a fluid motion, she rolled across the bed, propped herself on her elbows and took my penis into her mouth. The floor seemed to drop from under me. It was an effort not to fall. Every muscle strained to stay in place, as though I were standing on the deck of a ship tossing in a storm. I grabbed her silk-covered shoulders and groaned.

"Oh, you like that," she said, taking her mouth away for an instant. "How about this?"

And she took all of me, all the way in.

"Hmmm?" Her voice hummed through my cock.

"Yes," I said. "That's ... very ... uh..."

Taking her mouth away again — "What were you going to say?" — and replacing it.

"I don't know. But I'm sure it was complimentary."

She chuckled at my loss for words, and my penis buzzed some more. She drew her head back slowly, trailing her tongue along the stiff underside of my hard-on. I shot off in her mouth.

The hot stream caught the back of her throat, nearly gagging her, and semen bubbled through at the corner of her lips. She hacked, once, but she held on and started swallowing. The gentle pumping of her tongue siphoned the come from my narrow slit. Nothing in my life had ever felt so good.

"Well," she said, with a smirk, when I was empty. "Didn't expect that so soon."

She wiped her lower lip and licked her finger.

"I'm sorry," I said.

"Sorry for what? You're excited. That's good."

"Yeah, but it's over now."

She cradled my shiny wet dick in the palm of her hand, examining it closely — the fat knob at the end, the purple vein that looped in the center.

"How old are you?" she said.


"Oh, you're a stud. We'll wait a few minutes and start over."

That was the one good thing I remember about adolescence. Erections were cheap and plentiful, like gasoline in the nineteen-fifties.

She rose to her knees, shrugging out of her robe, and she hung her arms over my shoulders. Our naked bodies pressed together as she knelt on the edge of the bed. We kissed. Her lips were salty, with an oily film like a raw oyster. My own come and I was tasting it.

My hands went everywhere, impatient to map the white wilderness — down her back and over the cool globes of her ass, then up to her small breasts and stiff nipples. At last, as I tweaked and twirled a nipple with one hand, I dropped the other across her taut stomach into her mat of kinky hair. Inside stood a pair of tiny flaps, tough but yielding, like rubber, and inside those, a sopping wet channel receded into nothing. I pushed my finger into it.

"Yes!" she gasped, breaking our kiss.

She clutched the hair on the back of my head, and I buried my face in the rose-fragrant curve that joined her neck to her shoulder. I licked. I nibbled.

"I am so fucking horny," she said. "Fuck me, please."

I froze at the words. I knew what was going to happen. I longed for it. But the sudden reality of it caught me off guard. She sensed me tensing up.

"Never?" she whispered, her lips at my ear.

I wiggled my head, still nuzzling her neck, and gave a noncommittal whine, like "Mmm-mmm." I could admit to some experience with nude girls, but I'd never done the Big One.

There was a smile in her voice as I heard her say, "You're going to enjoy this."

And she fell back onto the bed, dragging me down with her.

The wind shook the windows every few minutes with a violent thump thump thump. It wasn't raining, or very cold, but it was overcast and blustery, and it felt good to be inside, in a dim bedroom with rose-colored walls, and to be in bed naked with a woman.

She made her way down my body with her mouth. She licked my balls. Christ, she licked my balls! Is there any feeling in the world so delicate, yet so intense? Gently but expertly, she sucked one nut into her mouth, then the other. She knew just how much pressure it took to make them tingle without hurting. This was a married woman, after all.

Holding my half-limp dick in her hand, she worked her way back to my face, kissing and nibbling — my stomach, my chest, my neck.

I wasn't passive during all of this. When she reached my mouth, and our lips mashed together, I reached across my body and found her bush again. The hairy husk parted, and my fingers sank into the dank ooze beneath. I massaged her swollen clit.

She rolled us over, so that I was half on top, and she moaned as I worked my way down, keeping my hand on her on her pussy, lapping at her neck and chest. One of those log nipples grazed my chin. I caught it in my mouth and sealed my lips around it.

"Suck it hard," she said. "Bite it. Bite it."

I dialed up the pressure between my teeth, and her little tit swelled beneath my palette. I was afraid of hurting her, afraid she'd squeal and push me away. But she only demanded more.

"Bite it harder, you little shit! Fuck God yeah!"

My dick was back at full extension. She gave it an exploratory squeeze, and, satisfied I was ready to go back to work, bucked and pushed and flipped us over again. Her nipple was ripped from my teeth, and I was on my back, her knees on either side of me, her crotch spread above mine like an arch with a keystone of black hair. Her snatch descended fast, and just like that, my brief existence as a virgin was over.

No — it was not overrated. Everything I'd heard was true. A moment ago, I couldn't have imagined anything sweeter than coming in her mouth, but this! Every nerve, everywhere on my skin, focused its capacity for pleasure into the last half inch of my penis. Than which nothing greater can be thought.

The shock in my eyes amused her.

"Yeah, that's what it feels like," she said. "This what you've been waiting for your whole life."

"Is it like that for..."

"For me, too," she said. "But different. Perfect, isn't it? The way we fit together?"

All I could do was exhale.

"It's all new to you. I forgot what that's like," she said. For a second, I hated her being in control while I was so helpless to resist, but that didn't last. She would go crazy soon enough.

She lay down on my chest, kissing my nipples and neck and lips, lovingly, the calm before the storm.

"You're so hard," she said. "Let's put you to work."

There was a delicious tugging on my dick, and in my stupor I felt myself turning, ceiling and wall and window and bed passing in succession. Her face was below mine, framed in the glow of the satin pillow. I was on top yet again. She hooked her heels behind my knees, strapping me on like a dildo. I had no way to move but up and down.

"Just push and pull," she said. "Do what you feel like."

Gazing in her eyes, I began to stroke, tentatively, then faster as she spurred me on.

"Fuck me hard," she commanded. "Fuck me harder! Don't be a pussy. Don't be a puh ... puh ... pussy. Rape me!"

I humped her furiously. She wailed and scratched my back, but I couldn't keep it going. My knees were jammed together painfully, and they burned on the slick satin coverlet. The tension drained from my arms, and I collapsed on her, burying my face in the pillow. That helped: I could move more freely, even if I couldn't look at her anymore. I didn't care. All that mattered was the sweet ache building up in my cock.

She pushed her crotch at me as I rammed home. Her cat-sharp nails mauled my back. She grunted, bit and sucked my shoulder, and just when I couldn't stand anymore, she threw back her head and screamed.

I blew my bolt into her grasping cunt, my insane roars muffled by the pillow. Then we were gasping together, quickly at first, then in bursts that came farther apart, and farther.

She was the first to recover, if only because I was dead weight on top of her and she needed to breathe.

"Come on," she said.

It took all the strength I had to slide off her chest. My cock stayed where it was. I laid my cheek on the pillow, facing her. The satin was damp with my drool, and my ear — the one next to her mouth when she screamed — felt flattened and numb.

"It's been so long since I had a good fuck" she said at last. "How are you?"

I didn't answer. I couldn't move.

"Then I guess we did fine."

She touched a hot spot at the base of my neck.

"That's going to be as red as a cherry," she said. "If I were you, I wouldn't take my shirt off in front of my parents."

She explored my bare back with her fingertips, raising a faint but delicious sting along the scratches that were beginning to swell.

"Those, too," she said. "Here, see what you did?"

Lazily, I raised my head. She cupped a hand below her right breast, holding it up for me. A chain of red blotches circled the nipple, branded on the white flesh. Separately, they were nothing but poorly defined ellipses, fuzzy at the edges, but together they unmistakably reproduced the pattern of my teeth, which I recognized from countless sandwiches and candy bars.

"They're going to bruise like hell," she said. "I can tell you and I are going to have a lot of fun."

Her name was Zelda, believe it or not, and she was the daughter of my most cultured customer, a tall guy with a high bald head who played bass in the Philharmonic. I liked him a lot, and when I started spending my paperboy money on concert tickets, I would meet him backstage after the performances, and we would ride back to the neighborhood together on the el, arguing about music and current events. Our discussions stimulated my mind in ways nothing at home or school ever did.

Zelda married young. She left home before I started delivering papers, but one day she walked out on her husband and came back, and there she was at the door when I came to collect. She'd been playing the piano in the living room when I rang the bell, and when I identified the piece — one of the Debussy Preludes — we clicked the same way I did with her dad.

OK, maybe not quite the same way. It was about a month after she moved home, on that cloudy Saturday morning in April, that she met me at the door in her blue kimono and invited me upstairs. Her father was off at a rehearsal, preparing for a concert I attended that same night. I met him backstage as usual. All the way home, neither of us mentioned her.

That's all the exposition you require, I think. When you're fifteen, and a mature woman decides you're worth fucking, it's easy to convince yourself you're in love. Whether I really was or not, I was dying to see her again. I slowed down before the house when I delivered the paper, even knocking boldly on those days when I didn't see her father's car parked out front. No one answered. When I came to collect, her father paid me. Zelda was nowhere to be seen, and I had no legitimate reason to ask where she was.

At home, I jerked off over and over, remembering the way her pussy felt around my sophomore cock. Mom wanted to know why I was spending so much time in my room. I told her I had a lot of homework.

It seemed like an eternity before I met up with Zelda again, although in abstract, chronometric terms it was only about two weeks. She appeared again out of the blue, on a sunny Friday afternoon when we arrived at her father's house at the same time. She was coming home from work in a gray suit and carrying a slim brown briefcase. I handed her the paper at her door.

"Are you doing anything tomorrow night?" she said at once. Greetings are unnecessary between a woman and her boy.

"I was going to the Philharmonic," I said.

"Skip it," she said. "Come over. Dad will be gone all evening. We'll have dinner."

No need to explain further. My plans changed on the spot, even though, as far as my parents were concerned, the concert was still on. I left at the usual time and walked straight to Zelda's house, so keyed up I could barely breathe.

My temples were throbbing when I walked up the concrete steps, and they stopped cold when a woman I'd never seen before answered the door. She was shorter than Zelda, with rounder hips and much bigger tits. She had dark red hair just long enough to overlap her collar. I guessed it was dyed. Her lips were a garish shade of orange, and her eyelids were thick with blue shadow, which she probably thought brought out the pale blue in her irises. Her eyebrows were plucked thin, and reddish. She was wearing a red leather skirt and black panty hose and a black satin blouse that strained to hold in her knockers. She'd taken her shoes off. As she sized me up, she held the handle of the door in one hand and a glass of white wine in the other.

She was in my way, and I wanted her to die.

"He's here!" she called over her shoulder.

Zelda came in from the dining room, wiping her hands on a dishtowel. She was barefoot in jeans and a parrot-green T-shirt — and no bra, which was the first thing I noticed — and she was smiling like there was nothing amiss. She must have known I wanted to tear off her clothes, but here she was, calmly planning a leisurely sit-down meal with this strange bitch. When could we get rid of her?

"Don't you look nice," Zelda said.

I was wearing my brown jacket and a tie, all the better to convince my mother I was really off to hear Stravinsky and Beethoven. I felt foolish in them now.

"This is my friend Abigail."

"Abby," the bitch said. She held out a plump hand with stubby fingers, which I squeezed in a noncommittal way.

"I hope you don't mind she'll be joining us for dinner," Zelda said. "It was sort of a last minute thing. We're both going through separations."

"Disappointed?" Abby said with a wink.

"No, why?" I said.

"No reason," she said.

"I wasn't expecting you to dress up," Zelda said. "I only made pasta."

"It goes well with white wine," Abby said. "But everything goes well with white wine."

She took a sip, and we moved to the dining room. I sat down while Zelda and the big-breasted obstacle to my every desire brought in a casserole dish and some small green salads.

"Would you like some wine?" Zelda said.

"Men don't like wine," Abby said. "Offer him beer at least."

"Beer, then?" Zelda said.

"Do you have any Coke?" I said.

"Coke it is," Zelda said.

She sat at the head of the table with me on the corner and the bitch to my right. The pasta was limp ziti with chopped red and yellow peppers and some oil and Parmesan. It was nice, but my stomach was twisted in knots and I only picked at it. I didn't touch the salad.

I reached for Zelda's leg under the table, but she brushed me off. Then I tried holding her hand, but she pulled it away and looked past me while she talked to the bitch. It was like I wasn't there, or I was unimportant, or she was deliberately making me suffer.

The bitch asked me about school, and my favorite subjects, and what college I wanted to go to, for God's sake.

"I haven't decided," I said. "I'm only a sophomore."

"I don't understand it," Zelda said. "He's usually much more talkative. He's very knowledgeable about music. That's rare for someone his age."

"Do you play?" Abby asked.

"No," I said. "I collect records."

"I think he's angry I'm here."

"I can't imagine why," Zelda said. "Are you angry she's here?"

I didn't answer. My throat was tight, and my face was burning. Zelda must have noticed how red my ears were, but all she said was, "Come on. Help me clean up."

We carried the things into the kitchen while the bitch poured herself some more wine.

"Leave your plate on the counter," Zelda said. "In case you're hungry later. You didn't eat much."

Nonchalantly, she rinsed the plates and placed them on a rack. I wanted to shake her by the wrists, but a boy can't do that to a woman, even if she is tormenting him, or she'd think nothing of telling him to go on home. So I stood in close to her at the sink and whispered, "When is she going to leave so we can be alone?"

Zelda laughed out loud.

"What's funny?" Abby called from the dining room.

"He wants to know when you're going to leave so he and I can be alone."

"The poor thing!"

"You really have no idea what's going to happen here, do you?" Zelda said.

Utterly at sea, I could only stare.

"You're going to eat her out, and I'm going to watch."

She touched the front of my trousers.

"Oh, that's better," she said. "Abby, I think he's fine with it!"

"Oh, goodie!" came the voice.

"I told you we were going to have fun," Zelda said. "I meant it. Let's go. She gets mean if you make her wait."

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