Glen and Casey - Doing It The Hard Way

This story continues on from my previous two stories, A Sleepover With Aunt Stephanie, and A Sleepover With Aunt Stephanie – Part 2. If you have not already read those stories, here is a brief rundown on the story so far, to put you in the picture.

In A Sleepover With Aunt Stephanie, seventeen-year old Glen lost his virginity to his Aunt Stephanie, aged thirty-one. They then began a casual affair, for several years.

In Part 2, four years later, they were caught in bed by Glen’s younger sister, Casey, then aged sixteen, and she asked to join them. Although reluctant to take his sister’s virginity, Glen gave into temptation, and as Stephanie looked on, he became the first man to make love to his young sister. During their session in bed together, accompanied by Stephanie, Casey informed them that she had recently been experimenting in oral sex with her best friend, Rowena.

Glen and Casey’s parents were away on a cruise together at the time, and the story ended with the three of them contemplating the next two weeks together, until their parents returned home.

The story continues…

For the next two weeks, until my parents came home, Stephanie stayed at our place, and the three of us fucked the nights away, my beautiful aunt, and my sweet little sister, and me. What a fortnight!

I got to explore Casey’s pretty little body, and Casey got to practice some of the oral sex skills she had honed with her best friend, Rowena, by going down on Stef, and teaching her a few things about the subject. Naturally, Stef returned the favour, while I looked on, driven to incredible extremes of lust by Stef’s and Casey’s oral lovemaking, and then satisfying that lust by fucking either one of them, or sometimes both of them in one session, by holding my own orgasm until the first one had come, and then fucking the other to a mutual explosion of ecstasy.

It was like an incredible two-week orgy, but like all good things, it had to come to an end when our parents returned from their Pacific cruise. They were happy to find that Stephanie had spent so much time with Casey and me while they were away, and my mother thought it was just great that her little sister had so much in common with us. It seemed that life was about to go back to normal again, when just one week after returning from the cruise, my dad got word that another branch of the company he worked for was opening up in an outer suburb of Melbourne, and he had been hand-picked to oversee the opening.

It meant he would be away for nearly a month, but since our mother still had some annual leave left in her job, they decided that she would go with him for the first two weeks. I got the impression the Pacific cruise had been a bit of a second honeymoon for them, and another two weeks down south were going to lead to some more horny times down there, but of course, that would leave Casey and me alone in the house again…..

Ten minutes after we got the news, Casey beckoned me into her room, and said, in a quiet voice, “Are you gonna ring Stef, or do you want me to?” Her smile was wickedly mischievous.

“I’ll give her a ring,” I smiled.

A short time later, I went to my own room, to ring Stephanie on my mobile phone, to tell her my parents were going away again, but her response was, “I’d be there in a flash, Glen, but my boss was supposed to go to a manager’s conference in Sydney for the next two weeks himself, but his wife’s pregnant and she’s having some sort of complications, so he’s asked me to go in his place.”

“I see,” I replied into my phone.

“It was only a request, but I don’t think I can refuse,” Stephanie continued, “but I’m sure you and Casey will find plenty to do without me.” I could hear the smile in her voice, over the phone.

“I’m sure we will,” I answered back.

“Just remember, when I get back, I expect a long, slow session with you, okay?” I heard her say over the phone, “Preferably with Casey there to help things along.”

“Now that’s a request I can’t refuse,” I answered, smiling myself.

I wen to Casey’s room, and told her told her the bad news, that Stef couldn’t join us while our parents were away again, and her reply was, “I’m sure you and I can find plenty to do without her.”

“That’s exactly what Stef said,” I said, shaking my head.

“Well, you keep saying how much alike we are,” Casey smiled.

It was true, though. Casey had definitely inherited the curvy figure that seems to run in the women in my mother’s family, and except for her ash-blonde hair, and fairer skin, she looked like a smaller and younger version of Stef. I think that was part of what made threesome sex with the two of them so exciting, the fact that they looked so much alike.

Later that night, as we sat around the kitchen table, my dad said, “Well, you guys managed to stay on your own here without wrecking the place for three weeks when we went on the cruise, so I know your mother and I can trust you while we’re in Melbourne.”

“No problem,” I said.

“And I know I can trust you to look after your little sister,” my dad went on.

“She’ll be in good hands,” I said, and then, I added, “I’ll take good care of her,” as Casey rubbed the top of my foot with hers under the table.

The next morning, my boss at the bank gave me a couple of hours off to drive my parents to the airport and see them off. Then, it was back to work, and after the bank closed, I drove straight home. Casey was already home from school, and we cooked dinner together, and ate it, then watched some TV, just like any other night. We had a few laughs, like we always did, and then it was time for bed.

I was sitting on the side of my bed, getting ready to get in, and Casey appeared at my door, dressed in a pale blue silk nightie. It was pretty short, and kind of sexy. “Can I sleep in here with you?” she asked.

I looked at what she was wearing, and I said, “You realise, if you get in here dressed like that, I’m probably gonna fuck you, don’t you?”

“Well, I was hoping,” Casey said, with that mischievous smile. She walked over to me, and stood so close that she had one leg on either side of my left thigh, as I sat on the side of my bed, and she looked at me, and said, “We’ve got the house to ourselves again.”

I looked up and said, “So, where would you like me to start?”

“You can start by throwing me into bed, and we’ll work it out from there,” she smiled, down at me.

“I’m not going to fuck you tonight, Casey,” I said, looking up.

“What’s going on?” she answered, looing a little surprised.

“Not until I’ve gone down on you first,” I said, and I put a hand on each of her hips, taking her weight, and turning her so she fell back onto my bed. She landed next to me on my left, and scooted back into the middle of the bed, and as she bent her legs to push back with her feet, I saw she had no pants on, and her pretty little pussy was exposed to me.

“You’re not wearing any knickers,” I said, in surprise, but it was hard to keep the smile off my face.

“What’s the point?” Casey replied, with a girlish smile, “They wouldn’t be on very long.”

I turned Casey’s nightdress back, and gently but thoroughly explored her sweet young pussy with my tongue and lips, taking her to the brink of orgasm, but not letting her go over the edge. Then, when I knew she was ready to come, I fucked her gently in the missionary position, as we kissed deeply, and she tasted her own pussy juices from my lips, and before long, Casey had a shattering orgasm, underneath me. Only then did I allow myself to take my own pleasure, and I immersed myself in sweet release, as I filled my little sister’s exquisite pussy with my seed, for the first time since our parents returned home from their cruise.

Casey and I went to sleep fairly quickly after our orgasms, but a few hours later, in the middle of the night, we both woke up, and she rolled over to me, putting her mouth near my right ear, and whispered, simply, “Fuck me.”

Once again, we made love in my bed, short but very sweet, and resulting in a whimpering climax for my sweet little sister, and an equally satisfying orgasm for me, as her snug little pussy milked my hard cock to perfection.

Then, in the morning, when we awoke, Casey reached over, found my morning erection, and asked me if she could get on top. This was only the second time she had done this, but she climbed on top of me, and impaled herself on my rigid cock, riding it to a shuddering orgasm that saw her clenching her fists, and twisting her arms across her chest, and then collapsing on top of me in exhaustion. I gently turned her over onto her back, and entered her again, fucking her until I filled her with come for the third time in less than eight hours.

After she had recovered, Casey climbed out of bed, and went to the shower. I got up a few minutes later, and as I walked to my parents’ bedroom to use their en-suite shower, I could hear Casey in the bathroom shower, washing our sex fluids from her beautiful body.

She emerged from her room, dressed and ready for the day in her school uniform, consisting of a blue and grey plaid skirt, a white blouse with the school crest on the pocket, and white ankle socks. Her ash blonde hair was pulled back in a ponytail, and it was hard to believe this innocent young thing was the same person who had writhed in ecstasy in my bed, the night before.

After breakfast, I drove Casey to school on my way to work, and outside the school, she leaned over in the car, and gave me a sisterly good-bye kiss on the cheek. She smiled, and said, “I’m allowed to kiss you like this in public,” then got out of the car. While I was waiting for a break in traffic, I watched the sexy, girlish sway of her walk, as she went over to join her best friend and baton twirling buddy, Rowena, waiting for her outside the school gate, wearing the same uniform. Rowena looked up, saw me, and gave me a smile and a little wave, and I returned her wave as I pulled away from the kerb to join the traffic stream.

Like Casey, Rowena was sixteen years old, and their birthdays were only a month apart. Rowena had been Casey’s best friend since she moved to town with her parents, when she was thirteen, and Rowena had joined Casey’s baton twirling club. They went to the same school, and hung out together a lot, but for most of the time I had known Rowena, I had just seen her as Casey’s skinny little friend, and hadn’t taken much notice of her.

After Casey told me she and Rowie, as she called her, had been “experimenting,” and had practised oral sex on each other, I had seen Rowena in a new light. Rowena was a couple of inches taller than Casey, and a little thinner, but she still had a few curves just the same. She had wavy black hair, down past her shoulders, and olive skin, and it appeared she had inherited her looks from her mother, whose parents were Italian. She had those big brown eyes, and chiselled features, that a lot of Italian girls have, and lately she seemed to be getting prettier by the month. She had smallish, but nicely-shaped tits, legs that were long and thin, but shapely just the same, and a cute little butt that was like a magnet to my eyes when she walked past. In a couple of years, she was going to be a looker, and it was certainly no hardship having her coming over to our place all the time, to go through her twirling routines with Casey, in her electric blue practice leotard, and pale blue shimmer tights.

After work, I drove straight home again, and walked in the back door, and through to the family room, where I saw Casey sitting on the couch, with her legs crossed, sipping on a glass of lemonade with ice cubes in it. She was still wearing her school uniform, which was unusual, because most days, she would come home and change into some casual clothes. “Hey,” she said, smiling at me.

“Hi, Case,” I smiled back. We made some small talk about her day at school and my day at work, and she put the drink on the side table and got up. She walked over to me, and stood very close, close enough for me to smell her girlie scent, and her hair shampoo.

“See what I’m wearing?” she said.

I nodded, but didn’t speak. “I left my uniform on,” she said, “Do you know why?”

I had an idea where this might be leading, but I said, “Tell me.”

“I want you to fuck me in it,” she said, smiling that mischievous smile at me.

I felt a wave of excitement passing through me, and I said, “Why do you want me to do that? In your uniform, I mean.”

“I just thought it might be fun,” Casey answered, “You do want to do it with a schoolgirl, don’t you?”

I put my arms around Casey’s shoulders, and said, “I’d love to do it with you, dressed like that. Your room or mine?”

“My room will do,” Casey answered, “Pick me up and carry me in there. I’m all yours.” I picked Casey up with my left arm behind her back and my right arm under her knees, and started walking to her room. As we walked down the hall, she leaned over and kissed me on the mouth, a soft and sexy kiss that caused another wave of excitement to pass through me.

I walked into her room, and set Casey down on her feet next to her bed. She smiled at me with that mischievous, sexy and challenging smile, and said, “Like I said, I’m all yours. You can do anything you want.” She slipped out of her shoes, but left her white ankle socks on.

I looked at her in that uniform, next to her bed, inviting me to do whatever I wanted, and I held her to me, kissed her on the mouth again, holding the kiss, tasting her, tasting my little sister’s mouth, and with our faces close, looking her in the eyes, I said, “I’m going to go down on you first, then I’m going to fuck you, but I’m gonna take my time over it. I’m going to enjoy this, and I’ll make sure you do, too.”

Casey sat on the bed, and slid back over, to give me room to get on with her. She lay back on the pillow, without speaking, but looking me in the eyes. I lifted her blue and grey plaid uniform skirt back, and I saw she was wearing pale pink cotton panties, the colour of a strawberry milkshake. They were moulded to the shape of her pussy, suggesting some dampness down there, and I kissed her on the pussy through them, inhaling the sexy scent through the cotton. Then, I decided to do this a different way. I looked at her, and said, “Can you turn over?” speaking softly.

“What do you wan to do?” Casey answered, as though she knew whatever it was, it would be fun.

“I want to lick you from behind, and then fuck you doggy-style,” I said.

“Sounds like fun,” Casey said, almost in a whisper. We had done it doggy-style a few times before, during our threesomes with Stephanie, but I had been gentle with her, because it was less than three weeks since I took her virginity. I was planning a nice gently doggy-style fuck, but Casey said, “Glen, when you do it, can you do it hard?”

“How come?” I asked, smiling, but wondering why.

“Well,” she started, “Up till now, you’ve been gentle with me, because I only just started having sex, but I think I’m ready for a deep, hard fuck. I want to see what it’s like.”

“Okay,” I said, “but I’ll start off gentle and work up to it. Just let me know if it gets uncomfortable.” Then, I added, “But I want to give your pussy some attention with my mouth, first.”

Casey turned over on the bed, and I gently moved her into the position I wanted her in, face down, on her knees, sideways on the bed, so I could kneel on the carpet and lick her pussy from behind. There was a special kind of excitement in the way my little sister was letting me do whatever I wanted, even letting me position her just the way I wanted her on the bed, so I wanted this to be special for her, too. She had the right side of her face on the bed, so she could turn to the left and look back at what I was doing, and she said, “I love it when you lick me down there.”

“Well, that works out pretty well,” I said, standing back, “because I love licking you down there.” I looked at Casey, and took in the view, as her plaid skirt was pulled up, due to the position she was in, revealing her pink panties. I lifted her skirt, and turned it back over her hips, so I could have a good look, and get down to business. I wanted to leave her school uniform skirt on while I plundered her sweet little body for the pleasure it could give.

Casey’s pale pink panties were pulled tight across her buttocks, and were moulded to the contours of her pussylips. I kissed her gently between her inner lips, holding my kiss, and inhaling her scent through the gusset of her panties, and caressing both of her buttocks with the palms of my hands. “Mmmm, that’s nice,” I heard her ...


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