Milky Nipples

My paper is delivered by a twelve year-old boy, Kyle, who lives three houses down from me. He has delivered the paper for almost a year now, and is often the way, he inherited it from an older sibling who "outgrew"the job. In this case the sibling was his sister, Jennifer, who was now almost 19. At first she helped him with the route, but after a week or so, he was able to deliver the paper with the same bullet-proof reliability as his sister. It had been months since I had seen Jennifer, and I missed her. She was a cute, likable girl, and she would often stop and talk when she wasn't in too much of a hurry. I am a single male, and while it might not have looked good for us to chat so much, she seemed to like the attention, and I liked talking with her.

So it surprised me when the doorbell rang, and I found Jennifer standing on my front step. It was December, and it was snowing outside. She said, "Merry Christmas," and handed me the annual calendar the newspaper distributes to it's subscribers.

"What are you doing," I asked. "I thought your brother had the route now."

"He's behind, and this particular delivery is slow every year," she said.

"So I volunteered to help him out a little. I don't mind, it gives me a chance to catch up with my old customers." Just then I remembered the expectation of a tip with this delivery, and I reached for my wallet. I dug around a bit, and pulled out a five. I handed it to Jennifer with a smile and instructed her to keep some for herself, and give the rest to her brother. She thanked me, but she didn't move. Instead, she asked a question which stills echoes in my ears as though it was yesterday. "I'll give it all to him, he's earned it all year," she said. "But I would like to get a little money for myself. What would I have to do?"

This question was clearly exactly what it seemed, but it took me so much by surprise, that I stood there a moment or two trying to be sure that I hadn't misinterpreted something. I steeled my courage, and offered my reply. "Your brother got $5, if you want $5, you could lift up your skirt," I said calmly, though my heart was pounding in my chest. And I held out another five dollar bill to Jennifer. She was leaned against the wall inside the door, still wearing her coat. She leaned forward, and took the bill between her lips, and held it there. I thought I might have a seizure.

Jennifer then undid her coat, and dropped it on the floor. She attended an all-girl's Catholic High School, and was still wearing their easily identified uniform: plain skirt below the knee, opaque white blouse, no nylons, no jewelry, black shoes, white socks. Jennifer took a deep breath, then let it out, and reached down to the hem of her skirt with both hands. She gathered the fabric slowly, lifting the plaid skirt inch by inch. first I saw her soft knees, then the beginnings of her thighs. The skirt continued to rise, and then, after a brief pause at mid thigh, it came up all at once. Jennifer held it there, gathered around her waist, while I stared at her lovely legs, and body.

She was wearing white, cotton string briefs that looked one size two small for her growing body. They were probably a year old, and the barely covered her anymore. Small tufts of curly brown hair peeked out from the edges, and, and the elastic at the top seemed stretched as far as it would go. "Do I have to turn around," she asked, not a bit scared. "Yes"

With that Jennifer raised the skirt up in the back, held it high above her waist, and turn slowly away from me. Like the front, the little bit of cotton fabric seemed barely enough to cover her. And, in fact, the sweet cleft of her ass was just visible above the waistband. At the bottom, her ass cheeks dropped below the elastic, and the lines marking the juncture of her thighs with her cheeks was plainly visible. I could feel myself sway, and beads of sweat were rising on my back, and forehead.

I couldn't think what to say, what to ask for. I didn't know how far Jennifer was willing to go. I didn't know how far I was willing to go. Then she bent over at the waist, while keeping a curve in her back, the way women do when they want to stick their bottoms out at heir lovers. The soft mound of her pussy stretched the fabric of her panties, and I just stared at it for a while. "Is this worth a little extra?" Jennifer asked, breaking the silence. "Absolutely," I stammered, and fumbled for the last five in my wallet. Jennifer reached back between her legs for the money, and tucked it in the pocket of her blouse. I continued to stare at her fine body. Her legs were slender and smooth, with less curve than a woman's, but more than a young girl's. The position she was in put tension on her panties, and they slid slightly down her ass, exposing more of her splendid cleft. I wanted to reach out and touch her, stroke her, but I didn't. Instead, I asked another question.

"How much money are you interested in making?", I inquired. It seemed to be an indirect way of asking the question I really wanted to ask, namely how far are you willing to go. "As much as you got," came the reply. And I stepped up the pace.

"I'll give you ten to take off the skirt entirely, and another ten to take off your blouse." Jennifer did not hesitate. As I dug for a twenty, she unzipped, dropped, and stepped out of the plaid skirt; leaving it on the floor in a heap. She then unbuttoned the cuffs of her long sleeve blouse, just as I held out a twenty dollar bill. She motioned for me to tuck it in her shirt pocket, which I did. I took the opportunity to caress her small breast as I did so, but Jennifer did not react. She undid the buttons down the front of her shirt, and let it drop slowly off her shoulders, and down her soft arms.

Jennifer stood before me in her white panties, and a small white bra. She made no effort to cover herself, nor did she seem afraid. I looked at her, and both of us smiled as our eyes met. Then Jennifer walked past me, and into the back bedroom. I the realized that we had been going about out encounter near the front windows of the house, and I was glad to be in a more private space. I followed Jennifer, watching the muscles of her ass rise and fall with each step. She moved her fingers under the elastic of her panties to readjust them.

In the bedroom, I stayed behind her for a moment, and lifted another twenty from my wallet. I reached it over her shoulder, she took it, and tossed it on the bed. Then I unhooked her bra, and slit it carefully off her slender shoulders. Across the room I could see her small breasts in the mirror, and her smile as well. She raised her arms over her head, and I took the invitation to reach around her and cup one tit in each hand. Her breasts were small, but round. They were soft, and her nipples were small, and pink. I rubbed each breast, and moved the tips of my fingers across her flat nipples. With some attention they rose from the middle of those pink circles, and hardened beneath my touch.

Jennifer craned her neck so she could whisper in my ear. "How much for the panties?," she inquired. Her deep whispers drove her hot breath into my ear, and I squeezed her soft mounds hard. "Another $100 for everything," I moaned in a determined voice. "$100 for all of it."

Jennifer let her arms down, and spun away from me. Her nipples remained hard, and she rubbed her breast herself while I dug in a drawer for money.

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Two fifties emerged from beneath some socks, and I handed them to Jennifer. She laid them on the dresser, and then pushed me back on to the bed. I watched from there as Jennifer danced, and moved around the room. She rubbed her breasts, and her flat tummy. She smiled at me, and pushed her ass back like before. She reached back with both hands and pulled the panties in to the crack of her ass, making an impromptu thong. She gyrated her bare ass at me, and I wanted to fuck her.

Jennifer then stood over me on the bed, and I obediently laid still between her legs. My time would come. Jennifer thrust her hands don the front of her panties, and out the leg holes in all manner of contortion. Then she pulled up hard on the waist band in front, pulling the white fabric hard against her crotch. A patch of wetness soaked through the flimsy material, and I heard the fabric begin to tear.

Jennifer use both hands to pull, and tear at the panties. She dug her fingernails through the fabric to make holes, then feverishly tore the holes larger. The panties disintegrated before my eager eyes. In a minute or so there was nothing left except the stubborn elastic around one thigh. She stood over me, her legs apart, her damp pussy looking down on me.

I reached up with one hand and touched a single finger to her soft pink cunt. She lowered herself to the digit, and just the right pressure parted her narrow lips, exposing the pink skin between them. I could feel the warm wetness drip out on to my finger, and I stroked her soft pussy carefully with that one finger.

As my advances became more deliberate, more firm, Jennifer began moving over me. She kept herself in a slight squat, her hands on her thighs to help with balance. My finger moved deeper between her lips, and I began to pay special attention to her clit. Her sensitive button was already hard when I found it, and she started to lose her balance as I teased it from it's lair. Jennifer lowered herself to her knees, keeping her torso erect.

I was still fully dressed, but Jennifer began to unbutton my shirt. I laid there passively and let her do all the work. She crawled over and around me as she stripped me bare, then I recalled her to the position she had before. Keeping her elevated over me, I reached between her legs and began to stroke her cunt with purpose. Jennifer humped against my hand, and I let one wet finger stray between the cheeks of her ass. As it touched upon her dry asshole, she lurched, and fell forward over me. I wrapped my free hand around her back, and stroked her ass from behind. She held on to me tightly, and rode out what was apparently a new experience. I worked my finger and inch or two in to her tight ass, but no more. Jennifer seemed increasingly interested in the sensations, but I could not resist the promise of her cunt.

I rolled Jennifer on to her back, and ran quickly to the bathroom. When I returned I positioned Jennifer with her legs wide apart, and her knees up toward her chest. Then I flicked on the electric hair trimmer I had retrieved from the bath. Jennifer put her legs down when she heard the sound, but I returned them to their former positions, and touched the buzzing clipper to her thick brown bush. In a few quick passes I trimmed away the bulk of her surprisingly thick pubic bush. then I dampened the stubble with a cloth I had soaked in the sink.

I let the cloth soak on her mound while I squirted shaving foam in to my hand. I tossed the sloth to the floor, and massaged the white foam hard in to her pussy. I let my thumb push in to her cunt, and massage her clit some more. With a fresh blade in my razor I made long, smooth, careful strokes over her foamy crotch. In seconds, she was as bald as the day she was born.

After letting Jennifer take a good look at her newly clean pussy, I began stroking it briefly. Then I plunged my face into her soft clean snatch. My tongue ran up and down her lips, and I sucked her clit into my mouth. Holding the little nugget between my lips, I flicked the tip with my tongue while I rubbed her tits with my hands. AS I felt her tension build, I rubbed harder and harder, and sucked deeper, and deeper. As she came for the first time; screaming, and lurching, I refused to release her clit from my soft vise. Instead, I continued to lick it even while in shoved my thumb up her damp ass, and my finger in her cunt. I could feel her orgasm squeeze me.

As I allowed her climax to subside, I rolled her over on all fours. She let her chest sink i to the bed, and her ass came up nicely. Behind her, in the well lit room, I admired her wonderful cunt. Clean shaven, and pink I allowed myself one gentle stroke with a finger before plunging my cock in it. Jennifer was breathing very hard when I first stroked the head of my thick prick between her bar lips. I held her down with one hand, but it wasn't necessary. She thrust her hips back at me as much as she could, and my cock slid part way in to her sopping cunt.

Her pussy was tight, and I pushed hard to make progress at first. I could feel her skin stretch to accommodate me, and my cock became wet in her pussy. With most of my cock inside her I pushed forward in one huge stroke, and buried my shaft to the hilt in her warm bottom. Jennifer screamed out,"Fuck me! Fuck me!", and she began humping back toward me with wild energy. I grabbed her hips, and pounded in to her. Her ass slapped against me as I drilled her with all I had.

Beneath herself, Jennifer moved one hand to her clit, and began to rub it furiously. Before I knew it she came again, and her spasming cunt gripped my cock. I pounded forward, and Jennifer screamed, and moaned as I continued to fill her cunt. "Fuck me," she yelled, "Fuck me in the ass." I didn't need to be told twice. I slid my rock hard cock from her pussy, and moved upward to her tight asshole.

Jennifer held very still as I smeared her wetness across her puckered behind. I was careful not to go too fast as I pressed the swollen head of my cock against her slippery asshole. Jennifer relaxed, and several careful minutes got the head of my prick inside her virgin ass. Now she started moving slightly, pushing back to meet me. My cock slid further and further inside her over the next several minutes. I watched as it disappeared in her vice tight ass.

Several inches had plunged i to her when I started to fuck her in earnest. Slow careful stroked brought moans of pleasure form both of us. Each move forward earned another fraction of an inch of penetration. In time, I was fucking her as deeply as when I was in her bald pussy, and her hand returned to her clit. I began pounding more feverishly, as I felt my own orgasm build. I squeezed her hips tight as I pushed myself inside her. Suddenly I exploded. My hot cum shot inside her, and my cock pulsed with glorious pleasure. Jennifer rubbed her clit in a frenzy, and her whole body shook with her third orgasm. I pulled out of her, and watched her ass, and cunt spasm and twitch with waves of sexual ecstasy. Jennifer began to giggle, and I kissed her soft ass gently.

Jennifer and I would meet again.

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