Penny's Journey

(This story is dedicated to Penny, a real person, who asked me to put her fantasies into a story.)

Some months ago I was on the phone to my younger sister, Marina.

"Can I ask you something personal?" She asked. I knew her marriage was not a happy and contented one so was curious as to what she wanted to ask.

"Of course. You are my baby sister. Ask away."

"How often do you have sex?"

Well that came out of the blue but I replied, "At least once a week with Dan and I masturbate at least once a week also."

"Really, that often?"

"Of course. You?"

"He won't touch me. I don't know why. I get so frustrated some times."

"How often do you masturbate?"

"I don't. I feel too guilty. How do you do it?"

"I like to use my fingers in the shower but I also have some toys that work really well."

"Toys?"

"Yes, I use a couple depending on my mood. You don't have any?"

"No, I wouldn't be game to go into one of those shops."

"Come over and I will show you what I have. I am sure one or two toys would help."

"OK, give me an hour or so."

I laid my toys out in the bedroom and waited for her to arrive. Once she arrived I showed her into the bedroom and pointed out my toys.

"Wow," was her response. "What are they?"

I picked up the big black dildo.

"I use this to excite Dan and when I want my pussy to feel full and stretched."

"But it is so big."

I just smiled.

Next was my vibrator. I switched it on to demonstrate the vibration and the rotating head.

"But this is the best," picking up my We-Vibe.

"It stimulates my clit at the same time filling my pussy. Best orgasms ever."

She looked stunned.

I had always been hot for my sister so I took a chance.

"Come on, I'll demonstrate and you can try them."

I proceeded to strip off. She seemed reluctant.

"Come on we are sisters. I have seen you naked plenty of times."

With that she slowly stripped off. I hadn't been completely truthful as we were kids the last time I saw her naked.

I had to draw my breath when she finally turned to me, naked. She was slim with flawless Mediterranean skin, boobs still shapely with very prominent nipples and a big hairy bush.

I lubed up the big dildo, lay down on the bed, spread my legs and slowly inserted it, groaning as I did so.

"Does it hurt that much?" she asked.

"It hurts really, really good." I replied smiling.

I stroked it inside me a few times then took it out. Wiping it down with a cleaning wipe, I told her,

"Now your turn."

I gently pushed her down onto the bed and spread her legs. Her pussy was gorgeous. Outer lips and labia visible through her bush, lovely. Now I definitely wanted her.

"Do you want to do it or do you want me to?"

"No, I will do it."

I lubed the dildo again and she took it, ran it between her lips and found her entrance. Slowly but surely she pushed it inside.

"It's so big. You are right. It fills me up."

I watched as she stroked the dildo in and out a couple of times.

"Now try this one," as I lubed the vibrator as I set it to maximum strength.

Removing the dildo she tentatively inserted the vibrator.

"Oh shit, that feels so good."

"Try it on your clit then."

She did so and very soon I could see would soon orgasm.

"Don't cum yet. You have to try the last one."

Again setting the vibe to max I handed it to her.

I took the vibrator and slid it into my pussy as I watched her insert the vibe.

I leaned over to ensure that the clit stimulator was placed correctly and noticed how hard her nipples were.

As she worked the vibe inside her pussy, I couldn't help myself but ducked my head and took one nipple into my mouth. She was startled at first but her arousal obviously got the better of her as she pulled my head harder to her breast with one hand as she continued to work the vibe in her pussy with the other.

I soon started to feel her muscle spasms build up and her whole body curled into a ball as she shook with her orgasm.

I lay back, opened my legs wide so she got a good view and worked the vibrator on my clit. Too soon I was also orgasming in front of my sister.

Once we caught our breath and calmed down, I could see she was embarrassed.

"That was fantastic, Sis. We must do it again some time," I tried to reassure her.

She looked confused and got up from the bed, "I have to go. I'll see myself out," and she left the room.

I lay there gently stroking my well lubed pussy lips hoping that I hadn't frightened her off.

*

A week or so after my toy demonstration there was a knock on the door and I opened it to find Marina standing there.

"Everyone has gone out so I thought I would come over. I hope you don't mind."

"Don't be silly," I replied giving her a big hug.

"Come in. Have a glass of wine. I am home alone also."

We sat chatting for a while but I could see something was troubling her.

"What's up? Everything OK at home?"

"Yes things are OK. But..."

"Yes?"

"I can't stop thinking about that day with your toys. I still haven't been game to go to a sex shop. Could I try yours again?"

All my dreams come true, I thought. I had never been with another woman but had always had strong feelings for my sister. Now was my chance, I hoped.

"Of course. Come to the bedroom."

Once in the bedroom, she shyly began to slowly strip off.

"Let me do that."

I began to unbutton her blouse as she just stood there. Having removed her top I reached around to unclasp her bra and used that as an excuse to hug her closely while nuzzling her neck. I felt her melt into my body.

Tentatively I moved my head to face hers and gave her a gentle kiss on the lips. Fortunately she responded by opening her lips and gently probed my lips with her tongue.

That was all the encouragement I needed as I proceeded to give her a full French kiss. At the same time I brought my hands around and cupped her lovely breasts. I felt her nipples harden.

We both came up for breath and continued to undress.

"Which toy do you want?"

"I like them all but the We-Vibe was the best. Can I use it?"

"Of course."

"Also, I hope you don't mind but I loved watching you work the vibrator in your pussy last time. Would you do that again for me?"

I just smiled as I spread her bush and her pussy lips to insert the vibe. Like me she was now wet enough to allow entry without lube.

I slid the vibrator into my pussy and spun around on the bed so that my pussy was in front of her face and vice versa.

As we lay side by side, I took her hand in mine and placed it on the vibrator in my pussy, at the same time reaching across to work the vibe in hers.

For a novice she worked the vibrator in me like an expert. Our moans of pleasure soon filled the room.

I could feel myself building up to orgasm when I felt Marina withdraw the vibrator. I was about to complain when a new delicious sensation struck my clit. I realised she had removed the vibrator so that she could tongue me.

I moaned and pushed my pussy into her face. The thought of my sister licking my pussy was so dirty but such a turn on.

I removed the vibe from her and did the same for her at the same time rolling on top into a classic 69 position. As I pressed my pussy hard down on her face I spread her legs wide in order to access all of her pussy.

Her juices tasted fantastic and I lapped up as much as I could while teasing her labia and clit.

Of course it didn't take long before her muscles tightened in her orgasm and she leg locked my head against her pussy until the muscles relaxed.

She took a short breath then continued her work on my clit. I soon moaned and stiffened in my own orgasm.

We changed positions and lay spooning.

"You licked my pussy like an expert," I complimented her. "Have you done that before?"

"No but I have always wondered what it would be like with a girl. I was so turned on when I saw you naked and using those toys. I've been searching the porn sites for girl on girl and I tried to copy as best I could what they did. Was it OK?"

"It was very good, thank you."

I continued, "I have a confession to make. I have always wanted you. I was so excited when you wanted to see my toys. I hope you don't think I took advantage of you?"

"No I don't. I was surprised and scared when you suggested we undress but once I saw you naked I started to get turned on."

She turned around and gave me a big kiss on the lips.

"Thank you for showing me how good sex can be."

She hesitated then asked.

"Can I ask a big favour?"

"Of course."

"I am worried about Adrianu. He is too shy for a 20 year old boy. He doesn't go out, not with girls, but sometimes with his mates. I am too shy and embarrassed to approach him and my husband is not concerned. You are much more open with sexual things, can I ask you, as a loving aunt, to sound him out?"

Adrianu was a very nice Greek boy. Very quiet with a very good physique. I would be more than happy to sound him out, and who knows maybe more.

"Of course I can help if I can but won't he be embarrassed with his aunt talking to him about sex?"

"Maybe, but please speak to him. You are his favourite aunt."

"Do you know if he watches porn or if he masturbates?"

"I don't know about watching porn. I assume he does. I think he masturbates. There have been suspicious stains on his sheets occasionally."

With that we kissed again, got up, showered and Marina went on her way after a long, lingering kiss at the front door.

*

In my smallest bikini I was waiting anxiously for Adrianu to show up.

I had waited until my husband was out of town for work and asked Adrianu over on the pretext that I needed help with the pool.

I am sure I have never worn such a small bikini when he was around so wanted to gauge his reaction.

The doorbell rang and I went to greet him.

I noticed the look of surprise on his face when I opened the door and inwardly smiled to myself.

After the charade of fixing the pool problem we settled down in the sun beside the pool.

I had prepared some snacks and cold beer and he had changed into his swimming trunks.

A couple of times I caught him sneaking looks at me.

Unfortunately his trunks weren't Speedos so I couldn't check him out.

After he had a couple of beers and the snacks I went for a swim while he sat on the edge of the pool waiting for his food to digest.

I deliberately undid the clasp of my bikini top, swam under water to where he was sitting and made a show of coming out of the water, allowing the top to fall away as I did so.

"Oh sorry," as I pretended to be surprised.

His eyes were glued to my breasts and their now erect nipples.

Not bothering to put my top back on, I asked, "I am sure a handsome boy like you has seen many much younger and prettier breasts than these?"

He struggled with a reply.

Looking at his crotch I was sure I could now see a bulge forming.

"I'm sorry if I have embarrassed you. I can put my top back on if you want, only it feels so good to swim topless. I do it all the time."

"Not if you don't want to." He managed to stammer not able to draw his eyes away.

Swimming around the pool I made sure that I spent a lot of time on my back displaying my boobs and even doing dives that I know show off my bikini clad pussy.

Once I caught a glance of him trying to adjust the front of his trunks I thought it was time to act.

I swam over to him, swiftly reached up and grabbed his arms and pulled him into the pool in such a way that his chest made full contact with my boobs.

As we wrestled and tickled in the water I made sure that my boobs made as much contact with his body as possible. As he tried to swim away from my tickling I briefly stopped and hooked my fingers into the elastic of his trunks. As he swam away I also pulled and his trunks came free.

He came up for air, obviously shocked and confused as I laughed and waved his trunks in the air.

"You will have to come and get them if you want them back."

He swam after me and I made the pretence of trying to swim away. As soon as he caught up to me I turned and 'accidently' reached for his cock.

We both looked at each other in shock. Him because my hand was wrapped around his erection and me because his cock was so large and hard.

I wondered if I had blown it by maybe taking things too quickly as we just stood there looking at each other, with my hand on his cock.

Tentatively he reached out and cupped my breasts with his hands. I smiled back at him and gently stroked him. With no objection from me he strengthened the massaging of my boobs and even began pinching my nipples.

Having my nipples pinched and rolled is my weakness and I soon dropped his trunks from my other hand, reached up and grabbed one of his hands and pulled it to my bikini bottom.

I spread my legs slightly and pushed his hand between my thighs, showing how I wanted him to massage my pussy. He continued massaging me as I withdrew my hand and cupped his balls as I stroked his cock.

"Take them off," I whispered.

We separated while he did so. As I restarted stroking him he fumbled with trying to get his fingers into my pussy. I am fully waxed so it should not have been hard but he was clearly very nervous and very inexperienced.

With one hand I guided his fingers to my clit as I whispered, "Right there."

I rested my head on his shoulder and moaned as his fingers stroked my clit. He started to get a bit carried away and I had to whisper to him again, "Not so hard. Be slow and gentle."

I could tell the pool water was washing away my lubrication so I stood up and taking his hand said to him, "We should take this inside."

We got out of the pool, dried off and I led him to the spare bedroom.

Laying down on my back and opening my legs, I asked, "Have you done this before?"

His eyes were glued to my pussy and he just shook his head. I had been wet before but, with the realisation that a young, virgin stud who was also my nephew was about to fuck me, my pussy flooded with juices.

"Come up here." I reached for his cock as he moved between my spread legs.

I ran the head of his cock up and down my pussy lips as much for pleasure as to lube his cock. Finding my entrance with his cock I thrust upwards to get him inside me.

We both groaned as he got the message and thrust into me.

He was a bit uncoordinated as he started to thrust into me hard and fast. I knew, as his first, he wouldn't last long. Sure enough after only a few strokes he groaned and pushed hard into me as I felt him shoot deep inside me.

I held him close as he moaned, "I'm sorry. I came too quickly."

"Don't worry. It happens to everybody on their first time. Now that your first is done we can get down to some serious sex."

We cuddled for a while to give him a chance to recover. I pulled his mouth to one boob while I reached for his still slick cock.

The miracle of youth, I thought as I felt him start to harden again, much sooner than I thought he would.

Taking one of his hands I guided his fingers back to my clit.

As I guided his fingers to massage my clit the way I liked it, "You know what that is?"

"Yes, that's your clit. I have seen pictures."

"Well now you can see the real thing. See how I am guiding your hand? That is how I like it, slow and gentle. Now do it yourself."

He was a good student. He continued to massage me just the way I liked. It felt great but I needed more.

"Put your fingers inside and find my G spot."

Tentatively, a finger slipped inside me and I couldn't help but groan. Eventually I had to guide his finger to the right spot.

"Feel that bump just inside me on the top."

He nodded.

"That's the spot."

"Now leave your finger there and try to massage my clit with your thumb."

He fumbled for a bit then soon got the hang of it. I could feel that it would not be long before I orgasmed. My muscles started to spasm and I grasped his hand holding it hard to my pussy.

"Oh fuck that feels so good. I'm going to cum. I'm going to cum," as I curled up in a ball as my orgasm hit me.

As I relaxed I uncurled my body and lay splayed wide open in front of him. I could see that now he was rock hard again.

I smiled at him, "Come fuck me. Fuck your dirty aunt."

He didn't need any encouragement and was soon thrusting deep inside me. I wrapped my legs hard around his waist and reached down to pull his body hard into me.

"Yes, fuck me hard, fuck me hard. My cunt loves your hard cock. Cum inside me."

He lasted longer this time but was soon deep inside me as he spurted his second load.

We cuddled again afterwards.

"I hope you didn't mind my dirty talk."

"No, it surprised me but it was a turn on. You will have to do it again next time."

I looked at him and smiled, "Next time?"

*

"How did it go with Adrianu?" my sister asked me on the phone a couple of days later.

I felt myself moisten at the memory.

"Very well. We had a long discussion. He is definitely interested in girls. I think he just needs time to come out of his shell. I will talk to him again soon and make sure he is on the right track."

"Are you sure? How do you know?"

"Oh I know. Trust my, um, instincts."

Little did she know that I had released the kraken with her son.

Two days after the first encounter he was standing on my doorstep again. This time there was no pretence. He looked expectantly at me and I lead him to the bedroom. Our clothes were soon discarded and I once again lay back spreading my legs.

This time I wanted to teach him oral. Reaching down and gently spreading my pussy lips, "Come here and lick me."

Of course he was unsure what to do so I guided him in what I liked.

"Run your tongue along my lips."

Tentatively his tongue lapped the length of my labia.

I shuddered, "Yes, just like that. Nice and gentle."

I could feel my juice start to flow.

"Can you taste me?"

"Yes."

"Do you like it?"

"Yes, it is very hot to see how I am turning you on."

I lifted my legs higher and spread my pussy lips wider.

"Tongue my entrance."

He seemed unsure so I pushed his head down with one hand until his tongue was there and then gently pulled him in. He got the idea and his tongue was soon teasing me unbearably.

"Oh fuck that feels so good."

Now I needed my clit licked.

"Use your tongue on my clit."

He did so but got a bit carried away. He was too rough for my clit.

"Slower and gentler please."

He was a quick learned and did what I asked.

"Put a finger in me and massage my G spot."

He did so and I was soon moaning in pleasure.

I started to buck with my impending orgasm but he held on, licking and stroking until I cried out, "Oh fuck I am cumming. Oh my God."

I clamped his head between my thighs as I came.

He kept licking and stroking but I soon had to stop him, "Too sensitive, too sensitive."

I looked at him and smiled, "You said you like dirty talk?"

He just nodded.

"OK, come up here and fuck me with that big hard cock. Fuck your dirty aunt's cunt."

He didn't need a second invitation. He slid straight into me.

I needed to be fucked hard.

"That feels so good. Fuck me hard. Treat me like a slut. Fuck me deep and hard."

He pounded me hard. I could feel his balls slapping against my bum, hear the sound of a squishy cunt being thoroughly fucked and smell my arousal.

He continued without respite attacking my cunt until I finally heard him start to groan and spasm. With one final deep thrust I felt streams of cum fill me deep.

I reached up and cuddled him as he caught his breath.

"I lasted longer that time," he smiled at me.

"Yes you did. It was great."

"I jerked off before I came over so I would."

I was shocked.

"Don't you ever do that again. What a waste. I don't mind if you come quickly at first. You can fuck me as many times as you like. I am annoyed with you. We could have fucked twice."