Natalie's House: First Time Fuck

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I take a young man's virginity as a favor to his aunt.
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IsabellaEmily
IsabellaEmily
3,772 Followers

Welcome to Natalie's House.

The Natalie's House series will feature a wide variety of kink and fetish entries, so check the tags and descriptions before diving into each one. This one hints at some very mild incest that will be further explored in part two.

Check out Friday Night Delight for an early entry in this series but be warned it has some specific peeing/spitting kink that isn't to everyone's taste.

As with most things that I write this story takes place in a happy alternate reality where people don't worry about pandemics, std's, or the need for birth control.

Featuring:

Natalie: A single woman that I met online a few years ago. She and I have begun a lesbian relationship.

Noah: A twenty-one-year-old virgin. He's a college senior, and Natalie's nephew.

Isabella Emily: A wife, a writer, a pervert, a pleasure seeker, and your humble escort through this story.

As always I enjoy your comments and private messages here on Literotica.

IsabellaEmily

~~~~

As usual my husband is home with the kids, having a Friday evening of video games and junk food. He knows I've gone out of town to visit a friend and won't be home until Sunday afternoon. He is aware that I'm sexually exploring with another female even though he doesn't know her name or any details about her.

He doesn't ask any prying questions in exchange for my letting him explore a bit as well. So far it's worked out great for us both. As individuals we're growing and having fun, and as a couple we're fucking as much as we did on our honeymoon. Maybe even more.

My friend's name is Natalie and she and I met nearly two years ago in a kink chat room. After months of chatting, and then voice chatting through Skype, we decided that we were ready to spend some time together in the real world. She's far more sexually experienced than I am and wanted a female friend with benefits where she could play sexually, without any romantic or relationship attachments springing up. I hadn't been with a female in a sexual way in several years and wanted someone to explore with.

Within forty-eight hours of meeting for lunch mid-way between her house and mine, we took the next step and spent an afternoon in a hotel room. I was shyly the recipient of pleasure that afternoon, sitting against the headboard and clutching pillows with my skirt bunched around my waist while she explored every inch between my legs with her fingers, lips, and tongue. She gave me so many intense orgasms that I could hardly walk out to my car on my own.

That Friday night I went to her house for our first overnighter, and it was a night of slow eroticism, with lots of candlelit cuddling, touching, licking, kissing, rubbing, caressing, sucking, soft moans, and loud screams as we took turns causing each other's bodies to be wracked by orgasmic tsunamis.

Finally, after so many years of trying to convince myself it had just been a college phase I admitted to myself that I crave the taste of aroused cunt as much as I lust after hard cock.

Ever since we've met as often as possible. Sometimes on weekends, sometimes during the day, and once for a delicious four-day weekend where we left our hotel room only twice for food. Sometimes I push my sexual boundaries as she urges me to try new things, and sometimes I ask to try things with her that I've always fantasized about.

Sometimes we don't try anything new, just staying in bed, repeating all the sexual things that we've come to love sharing with one another, losing track of our orgasms as we pant and moan in her king sized bed.

No matter what we do I always leave satisfied, with my clit tingling, my nipples pleasantly sore, and the taste of her delicious pussy lips lingering on my tongue.

I pulled into her driveway as the sun was setting. I felt a flush of lustful anticipation course through me. I grabbed my overnight bag from the backseat and approached the front porch, my heart thumping in anticipation. No matter how many times I knock on her door I still get butterflies.

However before I could knock the door opened, and Natalie was standing there, smiling at me with a look that was equal parts wholesome and seductive minx. I pulled open the storm door and stepped into her house, and felt her arms wrap around me as she pushed the front door shut and locked it.

Her lips found mine, and we kissed passionately, spending several long seconds pressed against each other in her foyer.

Her hands wander all over my body, staying outside of my clothes. But when her fingers began to lightly knead my pussy lips and clit through my yoga pants I knew that my first orgasm of the evening would take very little effort.

Finally she broke the kiss and pulled my bag from my shoulder. I could feel my wet arousal spread across my vagina, and I nearly moaned in anticipation.

"C'mon in." she said softly. "Let's sit for a few minutes."

"Sure." I smiled at her. "I need to unwind after that drive."

"Was it bad?" she asked.

"No, just rainy and frustrating." I replied, taking off my coat and hanging it on her coat tree. "It will do me good to sit quietly for a few minutes."

Sitting with her is one of my favorite things. We sit and talk, slowly working the conversation around to sex while undressing each other with our eyes and anticipating physical contact. By the time one of us reaches for the other we're usually both so horny that our first orgasms happen on the couch or the floor of the hallway before we even get to the bedroom.

She set my bag on her recliner and we snuggled up together on the couch, our fully clothed bodies pressed together.

"Remember when we talked the other morning?" she asked softly.

"You said you had a question to ask me?" I answer. "Ask away."

"Remember when you told me that one of your fantasies involved taking a young man's virginity and teaching him all about pleasure?" she asked.

"I do. It's something that I've fantasized about a lot over the years."

"Well I have a nephew. My older sisters son. His name is Noah and he goes to college near here. I'm the only family he's got within two hundred miles and over the past few years he and I have gotten kind of close." She said.

"Go on." I prompted her.

I had an idea where this conversation was going and a flush of heat spread through my chest.

"He was pretty sheltered while he was growing up. The only reason his parents let him move so far away from home for college was because I lived out here and could keep an eye on him. He and I have had dinner together almost weekly for the past three years. We've gotten to the point where we talk about everything. And I do mean everything."

She was using her fingertip to trace figure eights on my forearm, and I let a slight shiver of delight move through my body.

"Last week," she continued, "he turned twenty-one and I bought him a few drinks to celebrate."

"And.....?" I asked, erotic hope running through me.

"He's a virgin. He has almost no experience with girls and is pretty shy about sex." She answered. "He's a good looking kid and has a great sense of humor. He's not socially awkward or strange or weird or anything. He's been out on several dates but he's just never really gotten any of them further than making out."

She pointed to the mantle above her fireplace, and I saw the picture she was pointing at. It was her with a young man who was a bit taller than her. He was boyishly handsome, as if he'd grow into his looks and be a real head turner by the time he was thirty.

"And....?" I prompted her again, knowing she was enjoying making me drag this out of her.

"I've known about his virginity for a while, and have tried giving him some pointers." She answered.

I waited, knowing there would be more.

"So, after a few drinks he admitted that he's gotten fed up with having no experience. He asked my opinion about finding an escort just to get his first experience out of the way."

"No one's first experience should involve paying for it." I frowned. "He'll be nervous enough as it is. His first time should be with someone he can actually talk to and explore with. It should be someone he can ask to if he has them."

"My thoughts exactly. And I told him that in no uncertain terms." She said.

"How did he respond?" I asked.

"He asked if I had any idea on how he could find someone who would be comfortable with that, showing him the ropes, answering questions, and making sure he has a good time." She replied with a grin.

"Were you able to think of anyone?" I asked quietly, reaching out to take hold of her hand.

"I did actually." She replied. "I know that guiding someone inexperienced is a fantasy of yours, and I figured you'd be good at keeping the experience erotic and fun, while at the same time making sure he sort of learned what was what."

"Learned what was what?" I asked. "Exactly how much doesn't he know?"

"I didn't mean to make it sound that bad." She laughed. "He's twenty-one for crying out loud and has had unrestricted access to the internet for the last three years. I'm sure he knows everything there is to know. He just hasn't had a chance to actually put any of it into practice."

"Well can I ask a few questions?" I queried.

She nodded.

"First, how close is he to his parents and how deeply conservative is he? I don't need them out there angry with me for corrupting him."

"He gets along with them great, and they're actually pretty mellow now that they've accepted that he's an adult with his own thoughts and plans and ideas." She told me.

"Sounds like things have improved in that regard since he's been away from them." I said.

She nodded. "I don't think they'd have a problem. They get that he's an adult. And I can definitely assure you that he wouldn't tell them anyway."

"You say he's inexperienced." I went on. "He wouldn't misunderstand this encounter and assume we were now 'in love' or something would he?"

"Oh hell no." Natalie said with a smile. "He's not really interested in anything romantic or long term with someone your age."

"That's good." I giggled. "Carter is really understanding, but he might draw the line at having a college kid develop romantic feelings for me."

"I absolutely agree on that point. I've spent lots of time over the past few months talking to him about this." She said.

"Few months?" I asked. "I thought this came up recently?"

"He brought it up recently." She said. "Good old Aunt Natalie has been wondering about letting him fuck you for a while now. I've been conversationally exploring, even before he knew he was going to bring this up."

"Well then, just two more questions I guess." I said, taking a deep breath. "Where and when exactly would this be taking place? And do you think he and I will hit it off personality wise? It will be lots more fun if we actually get along."

"The where can be right down the hall in my guest room." She said softly. "And the when can be tonight if it's something you'd be up for."

"Tonight?" I giggled. "I knew something was up."

"As for hitting it off, he's down the hall right now, so you can go in and talk to him and see how it goes. I told him I'd tell you he was down there fixing my closet door. He's under the impression that tonight is just for you to meet and get to know each other. He's planning to head out after I introduce you."

"You filthy perverted schemer." I whispered, pulling her close for a quick kiss.

"Of course if you like him enough to actually fuck tonight I'm sure he'd be more than willing." She grinned.

"You must have been fairly sure I'd say yes." I laughed.

"I had a feeling you would." She answered. "And if you weren't comfortable with it, or with him, I'd just break the news to him next week that you weren't comfortable for whatever reason. He understands that you hold the deciding vote here."

"Have you told him much about me?" I asked.

"Just your first name, but not where you're from, or anything like that." She said. "Just that you're a dear friend, you're married and clean, and you love sex and orgasms and that you're about the nicest person I know."

"You might have built me up too much." I said with a smile.

"Nonsense! You'll be a fantasy come true." She said. "A gorgeous woman who's willing to have anonymous sex with him his first time, and you won't even make him wear a condom."

"I suppose that will be unique for a single guy his age." I said.

"Plus I know how much you've told me about your love of seeing, tasting, and feeling hot sperm." She said. "Here's your best chance to have some that's completely untried and fresh."

"You're horrible." I said. "And that would offend me if it weren't so fucking true."

We both laughed.

"Okay, one last question. Does he know about you and me? Or does he think we're just friends?" I asked.

"He knows." She said. "I thought it fair to tell him at least that much, about both of us, so he'd be comfortable knowing that neither of us were 'in-the-dark-missionary-position-only' women. I wanted him to be comfortable talking about this with both of us and exploring with you."

"Just with me?" I asked softly.

"If I thought he was a bit braver I'd be more than happy to teach him myself." She said with a smile. "I figured if he's comfortable enough fucking you then perhaps I can work him around to that someday. But for a start I assumed that introducing him to my degeneracy right away might be a bit too much."

"Speaking of your degeneracy," I asked, "where will you be while he and I....get to know each other?"

"Anywhere the two of you would be comfortable." She replied. "I can go to the movies. Or I can stay out here in the living room reading with the tv on so I don't hear you."

I raised an eyebrow quizzically. I trusted her to do it that way. But I knew her too well to assume that was how she wanted to do it.

"Okay, okay." She grinned. "I'd fucking love to watch. I'd love to sit on the corner of the bed and watch the entire thing. But I won't press that point. He's nervous enough without realizing exactly how degenerated I really am. But if you're okay with it I probably will be across the hall in my own bed listening and touching myself."

I leaned over and kissed her again, this time aggressively and passionately with lots of tongue. I slid one of my hands around the soft skin of her throat and used the other to grab a fistful of her hair.

After several moments I pulled my lips from hers and moved my mouth to her ear.

"You're the filthiest fucking slut I've ever known." I whispered. "It makes me so wet to think of you listening. Or watching."

She grabbed me and pushed me back against the arm of the couch, pressing her body against mine and kissing me again. This time it went on for several minutes, our hands wandering around each other's bodies.

Finally she pulled away.

"So what's the verdict?" she asked. "Are you willing to make a fantasy come true tonight?"

"Oh fuck yes." I said. "His. And mine."

"Great!" she smiled. "This will definitely make me 'Aunt Of The Year' for sure!"

"And," I said, putting my fingers against the side of her face, "if he gives any indication that he'd be okay with an audience, maybe we'll make this a fantasy fulfilling weekend for you too."

She smiled and stood up, and I joined her. She reached for and took my hand.

"Want me to take you in?" she asked.

"Maybe just to the doorway?" I said. "I'll go in by myself. If he really is shy or nervous there's no sense overwhelming him."

"Makes sense." She agreed.

She picked up a lit candle from the coffee table.

"Do you think I'm dressed okay?" I asked. "Should I change?"

She looked at my outfit, which I had chosen to be comfortable to drive in for a few hours. I was wearing black yoga pants, with a baggy sweatshirt over a sports bra, and running shoes.

"You could walk in wearing a parka and ski mask and he'd probably be okay with it." She answered. "He's shy, not picky."

I'd noticed that she was wearing what she often had on when I got to her house. A dark blue button up blouse and a yellow skirt that ended up above her knee. I'd noticed that she was wearing a bra, which made sense if she'd had Noah in the living room with her until I'd arrived. But I was willing to bet she wasn't wearing panties.

We walked hand in hand down the hallway and stopped outside the door to the guestroom. I'd been there enough times to know my way around her house pretty well. She and I had made each other orgasm in her bed, in the bed in her guestroom, in her shower, on the kitchen counter, and on the foldout couch in front of her fireplace.

She smiled at me once more and held out the candle and I took it.

"Thank you for this. I'm almost as excited for him as he probably is." She whispered with her lips against my ear. "If you need anything I'll be in my room pretending to sleep."

"Let me give you something to dream about." I whispered back, leaning in for one last kiss, using my free hand to slowly hike her skirt up until I could feel her bare thigh.

I'd been right about her lack of panties. She gasped into my mouth as my fingers found her slit. She was sopping wet and I pushed my tongue into her mouth as I pushed my finger into her hole.

I slowly teased it back and forth around the outermost half inch of her sensitive opening as she sucked my tongue. I broke our kiss and slid my finger out of her, pulling it up along her slit to drag over her stiff clit. I brought it to my mouth and gave it a quick suck, before pushing my tongue into her mouth to share the taste with her.

"Before I go home I'm going to lick some pleasure out of you!" I hissed in the dark hallway.

I stepped away from her and reached for the knob of the guestroom door, glancing back at her once and blowing her a kiss over my shoulder.

And then I opened the door and stepped inside, pushing it closed behind me.

Noah was sitting on the edge of the bed, and he looked positively surprised to see me. He glanced at the closet doors and then back at me, as if he was trying to decide if he should be busy doing something besides sitting and waiting.

"Hi Noah." I said, smiling at him. "I'm Emily."

"Uh, yeah. Hi. It's good to meet you." He stammered. "Aunt Natalie said you'd be stopping by tonight."

"You look surprised to see me." I told him.

I put the candle on the dresser and took the desk chair from the corner of the room. I wheeled it closer to the bed and sat down. The only light in the room was from a small reading lamp on the desk, but I could still tell that he was blushing furiously.

"Well, I guess I thought Aunt Natalie would come get me to introduce me to you." He said. "Not that I mind you coming in." He smiled then, and even though he was nervous his pleasure at seeing me seemed completely genuine.

"Well Natalie and I were talking when I first got here, and she told me about your situation." I said. "So I thought maybe I'd come spend some time with you one on one. So we could get to know each other."

"My situation?" he asked.

"Noah, don't be embarrassed." I told him. "I'm too old to be impressed or worried about how much experience or how many sexual partners someone has had."

"That's good." He said. "Because if she told you the truth then you know that I'm pretty new to.....well to anything sexual."

"Noah," I said, "I'm more concerned with what kind of lover someone is. Are they skilled? Are they kind? Are they inventive and willing to share and help create pleasure? Those are the things that impress me."

I kicked my shoes off and put my bare feet on the corner of the bed. I knew he couldn't clearly see the outline of my vulva in the dim light, but I got a thrill out of watching him pretend not to try.

"Some men," I continued, "can't arouse a woman or make her have great orgasms even after lots of sex with lots of different partners. Others are very good at making love with hardly any experience at all."

IsabellaEmily
IsabellaEmily
3,772 Followers