Hillary: The Summer of '92 Ch. 08

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Ben works on giving Hillary the favor she asked for.
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Part 9 of the 10 part series

Updated 08/30/2017
Created 08/03/2002
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D.C. Roi
D.C. Roi
1,335 Followers

From Benjamin Dornier's Journal

Wednesday, August 5, 1992

Today Hillary came to school wearing a pair of faded jeans and a short sleeved top that was short enough to expose a delightful strip of her bare belly. It took all of the self control I had not to stare at her most of the time she was in class with me. Of course none of the other students would have noticed because they were too busy staring at the very thing I was trying not to stare at.

Hillary was the last one to leave class. Before she did, she stopped and stood next to me as I stood at my desk. "What time will you be getting home?" she asked very softly.

I looked at my watch. "I should be home a little after one," I told her. Then I did something that surprised both of us. I ran my fingers lightly over the expanse of silky abdominal skin her outfit left exposed.

"Ohhh!" Hillary murmured, shuddering.

I grinned up at her. "I've been wanting to do that ever since you walked in here this morning," I told her. "Now get out of here. I'll see you at home."

"You bet you will," she giggled. She turned and walked out of the room.

I sighed as I watched her leave my classroom. Hillary had a body built for jeans.

I didn't have any meetings after my class and I'd allowed myself plenty of time to pick up some items I'd need to help fulfill the request my adorable young lover had made the night before. I still hurried. I wanted to get home and have things set up before she got there.

When I got home, the first thing I did was trim my fingernails short and smooth them with an emery board to make sure I didn't hurt Hillary. Next thing I did was heat up some water to almost boiling. I poured the water in a heat-retaining travel mug and stuck the tube of lubricant I'd bought in the hot water. I'd learned long ago that there's nothing like a dollop of cold lubricant to instantly kill desire. I set the cup with the lubricant on the nightstand next to the bed and got a few towels. I was pretty much ready. And just in time, too, because when I turned around, Hillary, still dressed as she'd been in class, was standing in the bedroom doorway.

"I didn't hear you come in," I said.

"What are you doing?" she asked. "What's all that stuff for?"

"Things we'll need if you still want to do what you asked about doing yesterday," I replied.

"Oh," she said.

I walked to where she stood, slipped my arms around her bare midriff, and kissed her gently on the forehead. "You don't have to do anything you don't want to do," I assured her. "If you've changed your mind, no problem."

She wrapped her arms around my waist and shook her head. "I haven't changed my mind," she said, very softly.

I took a deep breath, inhaling her wonderful fresh scent. I have no idea what perfume she wore, if any. In my mind, what I smelled was the scent of youth and I loved it. As it almost always did, having her lovely young body pressed against mine produced an effect. Pressed against each other the way we were, Hillary couldn't help but notice.

She leaned back in my arms and smiled up at me. "Feels like you're happy I'm here," she said, her voice filled with glee. She twisted her hips back and forth. "I'm glad. I love it that I turn you on."

"How could you not?" I responded.

Holding my eyes with hers, she stepped back, reached down between us, and opened my belt. After that she undid the clasp at the waist of my pants, then the zipper went down, as did my loosened slacks. Her warm hand slid behind the waistband of my jockey shorts and I moaned when slim, lovely fingers wrapped around my erection.

"Oh, wow! You're really glad to see me!" she murmured. She began to caress my swollen shaft while, with her other hand, she tugged down my undershorts.

I was a bit surprised by how aggressive Hillary was being, but I didn't mind. I thought she might just want to enjoy a session of regular love-making before we took the next step in our plan to attempt anal sex. Her gentle caressing of my erection continued, making me moan softly. She'd learned what pleased me and seemed to take delight in doing it.

"You like that, huh?" she murmured.

"Oh, yeah!"

She pushed me backward across the bedroom until my legs hit the edge of the bed, then she sank to her knees and I moaned even more passionately when she took my erection into her mouth. She proceeded to turn me every way but loose with her lips, tongue, and fingers. Her head bobbed in and out and I could feel her lips dragging along the veined sides of my swollen penis. The feelings her oral caresses evoked were electric, as if sparks of erotic electricity were arcing between us. My chest felt tight and I could hear myself gasping. It felt incredible! My legs were shaking and my penis felt as if it was getting harder and harder. God, if she kept doing what she was doing, it might explode! At least it felt that way to me and, of course, I was so turned on I wasn't really thinking clearly.

"Hillary, oh God!" I groaned when she cupped my dangling testicles in her warm hand and began fondling them. "Oh, baby, that...feels...so...good! Too...good!" I realized I was holding onto her bobbing head and had no idea when I'd taken hold of it. I had to fight an impulse to haul her back and forth on my erection. I was so turned on and what Hillary was doing to me felt so good I knew I wouldn't be able to hold back too much longer. "Baby, I...I'm gonna...I'm gonna...come...if...if you...if you don't stop...soon," I croaked, barely able to form the words and get them out through the waves of delight that crashed over and through me.

I was surprised when my young lover didn't stop what she was doing. It felt as if she was sucking on me even harder, her tongue was lashing the shaft of my erection, and her fingers were doing incredible things to my balls. It was as if she was trying to make me come!

"Hillary! Oh...God! Oh...God! Oh...Hillary!" I groaned. My hips were rocking back and forth as my body involuntarily kept time with my young lover's moving mouth. Then it happened. The wonderful feelings I was already experiencing jumped exponentially in intensity as my loins began pulsing, sending powerful jets of my hot juices gushing into my teenage lover's mouth. The grip I had on her head tightened and I held her on me while I sank to a sitting position on the bed because my quivering legs would no longer hold me. Hillary went with me, continuing to suckle and lick my erection, which began softening after my orgasm began to wind down.

Hillary finally let my now-flaccid penis slip from her lips, sank back so she was sitting on her feet, and grinned up at me. "Like that?" she asked, her eyes bright.

"Oh, God! It was unreal!" I gasped. I laid back on the bed, trying to get myself focused again.

The bed moved, then Hillary's smiling face appeared over me and her jean-covered leg brushed against me. I was still clothed from the waist up and she still had all of her clothes on. Her face dropped toward mine and our lips joined. I could taste myself on her as we shared a fervent kiss. It was a taste I'd long since come to enjoy.

I finally composed myself enough to sit up. When I did, I shed my shirt and undershirt while Hillary laid on the bed next to me, watching. I turned to her and said, "Stand up for a minute so I can get your clothes off."

Hillary giggled and stood up. So did I. She acted surprisingly shy when I pulled her top off over her head, then undid her bra and removed that. Her nipples were hard and as I bent and opened the clasp at the waist of her jeans, I managed to lick both of the rubbery buds of flesh. My action drew a soft moan from her. She sat down when I'd loosened the jeans and I pulled them down over her lean, gorgeous legs.

"Lay on your belly," I told her.

"O...K," she replied. Again her voice betrayed a trace of nervousness.

"You're sure you want to do this?" I asked.

"Ah...um...yeah...I...I'm sure." She stretched herself out on the bed next to me, on her belly.

I'd already decided to take things very slowly and gently, but knowing how nervous she was, I tried even harder. It seemed to me, beginning at the bottom was the best way, so I began by caressing her feet.

"Oh, God, that tickles," Hillary giggled.

"You want me to stop?" I asked.

"No way!" she replied. Her delectable body squirmed delightfully on the bed as I continued my caresses, paying careful attention to being thorough, working on the soles of her feet, her toes, and the top of her feet, too. I did each foot in turn. By the time I moved my attentions from her feet to her lower legs and calves, she was giggling and gasping. My attempt to relax her seemed to be working.

When I began trailing my fingers up and down over the silky warm skin of her calves, her giggles turned to soft murmurs of enjoyment. Keeping my touch as light as I possibly could, I trailed my fingers up and down along outside of one leg, then over her calf, then the inside. I did one leg first, then the other, taking time to thoroughly touch as much of her as I could. I looked up at my young lover's face and saw that her eyes were closed and she was breathing gently.

"You awake?" I asked softly.

"Um...hum," she replied sleepily. "Just...barely. That...that feels sooo...good."

I'd finished with her lower legs and moved my caresses to the backs of her knees.

The minute I began running my fingers over the skin at the back of her knees, she jumped. "Oh, God! That tickles!" she gasped.

By the time I finished teasing her knee area, Hillary was again wide awake and giggling so hard she had difficulty catching her breath. "You're...making...me...nuts!" she whimpered. "Oh, God, that tickles so much!" Her demeanor changed abruptly when I slid my fingers onto the back of a firm thigh. "Mmmmmm!" she moaned.

Since I'd been tickling the insides of her lower legs and knees, her legs were already apart. That allowed me access to the silky skin of her inner thighs as well as the rest of her delectable upper legs. I'm not sure which one of us was enjoying this more. It's difficult to accurately describe how wonderful her skin felt under my fingers as I caressed her incredible upper leg. The moans coming from my young lover were interrupted only by gasps for breath. Her body was trembling and her hips had begun a gentle rocking movement. From the way she was acting and the sounds she was making, I had a feeling Hillary was so aroused she only vaguely knew what was happening to her

Touching her had an effect on me, too. I had an erection that was probably harder than it was when she'd been working me over with her lips and tongue earlier.

My fingers stole lightly all the way up the baby-soft skin of her inner thighs and I caressed the little expanse of skin between her legs and labia. The sparkling dampness adorning her pink lower lips told me just how turned on she was. Her hips jolted when my fingers slid over the sensitive skin. She rocked them from side to side, too, seemingly seeking my touch on her labia.

"Please! Oh, God, Ben, please!" she groaned.

"Patience, my darling," I told her. "Just lay there and enjoy this." I slid my fingers along the crease between her buttock and upper thigh, around her buttock, onto her back. Across her back I moved, stopping to carefully attend to each of her sacral dimples, then I moved around her other buttock, back to her leg, then down between them.

"Oh, Jeezum! God, Ben, you can't believe how good that feels!" the object of my attention whimpered.

This time I traced the outline of her vaginal area, just barely brushing her labia, moving up, toward the little expanse of skin between her vagina and anus. Her hips bucked upward as her body sought more contact with my tantalizing fingers.

"Oh, yesssss!" she hissed. "Oh, God!"

I spent quite a bit of time on the small area of flesh, clearly making her wilder, before I moved my caresses up between her buttocks. I purposely avoided touching her anus, although I doubt very much she was aware of that. Her hips were rising and falling and twisting almost constantly now. I knew all I had to do was reach under her and touch her clit and she'd explode. But I didn't do that.

While I trailed the fingers of one hand over her firm, wonderfully formed buttocks, I reached for the tube of lubricant I'd put in the cup of warm water on the nightstand. I silently thanked the person who'd decided to put snap-off caps on the tubs as I used my thumb to flip the tube open.

"Don't stop," Hillary murmured when I stopped caressing her to squeeze some of the lubricant onto the fingers of the hand I'd been caressing her with.

"Just a second," I told her as I made sure my fingers were amply coated with the warm, slippery gel. "I'm not stopping." I flipped the lid of the tube closed, laid it on the night stand, and turned back to my exquisite young companion. I slid my left hand down over her inner thigh, between her legs, and this time I touched her labia.

"Oh, yessss! Oh, God, yessss!" Hillary whimpered. The motions her hips were making became much stronger.

I slid my lubricant-slick right index finger down between her buttocks, onto her anus. I spread as much lubricant around the area as I could, then I began gently pressing the tip of my finger against the tiny puckered opening. At the same time, I slid the fingers of my left hand down and began caressing her swollen, slippery clit.

"OH, GOD, YESSSS!!" she cried and her hips rose. My finger slid inside her snug nether opening to the first knuckle. "OH...YES...OH...YES...OH, GOD...YES! GONNA...COME...GONNA...COME...MY...GOD...OHHHHHHH!!! OHHHHHH!! OHHHHHHHHHHH!" Her screams of joy were so loud I momentarily mused that it was good we weren't in a motel somewhere. Her wild rocking motions continued, drawing my finger deeper into her. After a surprisingly long time, her moans began to decline in volume, but didn't stop. "Oh...God...oh...God...Ohhhhhhhh!" Her motions became less fervent, too. After another lengthy period of moaning and motions, she took a long, deep breath, then she lay still.

I slid my finger out of her bottom, and pulled my other hand out from between her legs. I stretched out next to her, put my arm around her, and kissed her gently on the cheek. "Are you all right?" I asked her.

"Oh, God, I think I died and went to heaven," she murmured in reply. "That was sooooo awesome!"

"It sure was awesome to watch," I told her and kissed her cheek again.

"You had your finger in my bottom," she whispered. "I could feel it."

"It didn't hurt, did it?"

"No way! That's what made it feel so wild, I think," she responded. "When you first started, I wasn't sure what you were doing. I mean, that tickling and all..."

"I wanted you relaxed," I told her. "I didn't want you thinking about what I was going to do."

"Well, you sure did that," she said. She made a face. "I gotta go to the bathroom." She slid out of bed and padded toward the bathroom.

I laid in bed, watching her go. There are few things nicer to see than a well-built nude young woman walking away from you. It was a sight I'd miss once our affair ended.

A few minutes later I heard the toilet flush, then I was treated to an equally delightful sight, that of a well-built nude young woman walking toward me. The sight of her jellied breasts dancing as she moved across the bedroom literally made my mouth water.

Hillary cleared her throat and I looked up at her rosy face. "You embarrass me when you look at me like that," she said. She flopped down on the bed next to me, then she reached down and wrapped her fingers around my revitalized erection. "You want to do something about this?" she asked.

"Um...I was kind of hoping to," I replied. "I mean...that is...if you want to."

She giggled and kissed me. "When was the last time I didn't want to?"

"Good point," I responded and kissed her back. That led to our laying there, necking, for a little while. Kissing her was incredibly enjoyable.

"I want you," she gasped after we broke one of our kisses to get some air. "Do...do you want me to...to go on top?"

I nodded. "Face away from me, toward me feet, though."

She looked puzzled. We'd never made love that way.

"Trust me," I said. "There's a reason."

Hillary gave me yet another quick, passionate kiss, then she moved so she was straddling me, facing my feet. I ran my fingers up her back and she shuddered. Then she lifted her hips, placed the tip of my erection at her vaginal opening, and sank down onto me. "It...it feels different being on you like this," she murmured.

"It doesn't hurt, does it?" I asked.

She shook her head. "No way. It feels great, just different." She leaned forward and started moving her hips up and down while I kept sliding my fingers up and down her back. "Oh, yessss! That's so neat!" she cooed. As her motions continued, she began gasping and moaning. I could feel her fingers tightening around my ankles and her bottom began to smack audibly against my thighs. She was getting close to coming...and so was I. I reached over to the nightstand and got some more lubricant on my finger. Then, as one hand continued to move up and down her back, I slid two slippery fingers of the other down to her anus and put just the slightest bit of pressure on it.

"Oh, God! I love how that feels!" she exclaimed and pressed back against my fingers. I could feel her anus spreading to let them inside her. She had to twist her hips up a little and that caused me to experience some very interesting reactions as it bent my erection into a position I don't remember it ever being in before. I kept the pressure on my fingers and the result was that the more Hillary moved the farther they sank into her bottom. Then her back arched and muscles clamped down on both my fingers and my erection.

"I...I'm gonna...oh, God, Ben! I'm gonna come!" she cried. I could feel her fingernails digging into the flesh of my ankles where she had hold of them. Her bottom was moving so fast I was worried my fingers would go in too deep and hurt her, but she didn't seem to mind. "Oh...God! Oh...God! Ohhhhhhhhhh!!! Ohhhhhhhhhhhhhhhhh!!!"

"Me...too...oh, God, yeahhhh!" I groaned when my second stupendous orgasm of the day exploded through me.

When our passion had finally expended itself, we laid there on the bed in the same position we'd been in. Hillary was lying on my legs, my softening penis was still inside her, as were my fingers. As my penis continued to soften, it slid from her. I finally was able to work up enough strength to pull my fingers out.

"You...you did it again," Hillary whispered. "You can't imagine how wild it feels to have something...in...in both...in both places." She rolled off me, turned, then slid up so we were lying next to each other again.

"You aren't hurt, are you?" I asked. I was afraid two fingers had been too much.

She smiled and shook her head. "No way. It's hard to describe how it felt," she said. "It stretched a little..." She took a breath and a gentle shudder went through her. "...but it was a really good feeling." She bent forward and kissed me. "Thank you," she said after the kiss. "You did it, you really did it."

"Well, sort of," I said.

She kissed me again. "I know, we didn't really 'do it' yet, but..." She took a deep breath. "Are we...you know...going to...to...do it...today?" Her tone of voice told me she wasn't sure that was a good idea.

I hugged her and kissed her forehead. "No, we aren't going to 'do it' today," I told her. "But maybe tomorrow...if you think you're ready."

I could feel her relaxing in my arms. "OK," she said softly. "Maybe tomorrow."

D.C. Roi
D.C. Roi
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