Aandc2 02 Jenny Gets Her Fantasy

Thanks to Freya Gersemi for her assistance in refining this story. Do yourself a favour and check out <a href="

https://literotica.com/stories/memberpage.php?uid=7564050

">her stories</a>.

This story is fiction and you are welcome to imagine the characters as you wish but everyone is 18+ at the time the story happens. Hopefully this is plausible. Issues such as STDs and family planning are considered outside of the narrative.

It is part of the Second Alice and Company series and you are recommended to read the first series first <a href="

https://www.literotica.com/series/se/alice-and-company

"> here. </a>

In particular, this follows on, a sort of second part, from A&C 11. Jenny Gives Billy His Wish<a href="

https://www.literotica.com/s/aandc-11-jenny-gives-billy-his-wish

"> here. </a>

Jenny here as this is my story. If you haven't read Jenny Gives Billy his Wish, and earlier revelations you may have problems understanding what is going on, until it gets to the fucking.

I have moved into Fourways Farm and I am living with Billy in the so-called Guest Wing. To say the house is big is an understatement as it has over a dozen bedrooms, all with their own sitting areas and bathrooms, across two wings, plus other facilities. Our sex lives are fulfilling but there was the inevitable, 'time of the month' intercourse fast, until, with a bit of guidance from Al, I discovered that I like anal sex.

I might say that I more than like it, but I definitely really enjoy it. In our third session, we accidentally went ass to pussy and the slightly taboo aspect of that turned me on. I had thoughts of experimenting more.

That night I dreamed of having a Gang Bang

, but all of the men were Billy and all of the cocks were Billy's shaft, as I call his penis.

----

However, as we were back to 'normal' sex, with a lot of fun in multiple positions, I wasn't immediately thinking about anal sex, except that we would be doing that next month. When we did we had lots of anal fun and I did more switching between ass and pussy when I was riding him in the reverse cowgirl position.

As I had switched to a cup, I needed to put out the training butt plugs as a clue to Billy that we were going to be doing anal. Accordingly, Billy knew what to expect, and he had files ready so that we had porn on the TV that matched what we were doing. Not only did it give us ideas to enhance our sex, it added a sense of 'others in the room' which turned me on even more. But that was something we reserved for our anal sessions.

----

After a couple of months, I began to get curious about doing anal and pussy sex at the same time, but without getting other men involved, a bit like Alice was doing with a vibrating butt plug. However, I wanted movement rather than just vibration.

I needed to search online to see if there were sex toys to make my dream come true. I found a site for sex toys via Literotica, a place where Alice had got someone called Alex to put her stories, along with mine, Donna's and others.

Now, I don't think his name is Alex, as mine isn't Jenny (I find it a bit amusing that the names go Alice, Billy, Callum, Donna, Eric, etc.) but I understand that Alex got confused reading a story where there was a Karen, Kate, and Kylie, so he prefers to use names that begin with different letters. What he will do once he gets to Zoe, I have no idea! But back to the website.

Amongst the anal toys, I found some things, double penetrators, that were like a cock ring, but with a dildo attached, or dual riders, that had a ball harness as well. Some had vibrators and one made it clear that the cock could be in the pussy or ass and the attachment in the other. I went for the non-vibrating ones, but of both types.

What I also found was a Dual Pleasure Vibe that had two dildos on one handle. I immediately got turned on with the mental image of getting myself "airtight" working the Dual in my pussy and ass whilst Billy deepthroated me.

Then, on a whim, I bought a dildo that had a sucker on the base as a possible alternative way of doing things, but I would have to think about how I was going to use it.

Whilst I was there, out of curiosity, I looked at some light bondage and found a set that had straps under the mattress with Velcro cuffs and ankle straps. It even came with a soft paddle. I bought this, partly to qualify my order for the free shipping option, and wasn't sure when or even if I would use them.

Once they arrived, I immediately played with the two types of 'add on' dildos to find out what they would feel like in both my pussy and my ass. I also had fun with the Dual Pleasure vibrator, but I really needed more time to get the most out of it, which would mean Billy being there. My plans for that were not yet ready.

----

I thought I would ambush Billy on a Friday night, mid-cycle, so we could continue our play over the weekend. He was getting ready for bed so I put out the training plugs and put the simpler double penetrator under my pillow. I dived into the adjoining bathroom. As Billy came out and heard him say, "Jen-babe?..." As the door closed.

Now I had done most of the 'prep work' earlier in the evening, so it wasn't too long before I emerged naked and ready.

Billy was sitting on my side of the bed, fumbling with the largest plug. "Jen-babe, have I got the dates confused?"

As seductively as I could, I said, "No, I wanted to try something new whilst we can."

Billy sounded cautious. "OK. Like what?"

I smiled. "Well... Al told me that, twice, you and Cal gave her a double penetration." Billy had never let that slip. "And I wondered what it would be like."

Billy's mouth dropped open and, eyes wide, he looked towards the bedroom door, possibly expecting Cal to come waltzing in.

I laughed and he looked back at me. I crossed the room, leant down to give him a deep kiss, and he reached up to cup my dangling tits. I stood up. "I'm not talking about a three-way... I bought some special toys." And I winked with a big smile.

His eyes widened again. "Like what?"

I reached under my pillow and pulled out the simplest one, the cock ring with the dildo attached and passed it to him. "It's called a double penetrator. You wear the cock ring and it gives you a second shaft."

He took it, twirled it in his fingers, and tugged on the ring to see how stretchy it was. "Oh, I see, I presume the probe goes in your ass?"

"Not necessarily. You can wear it above or below. I rather like your shaft in my ass, but I also enjoy it in my pussy, too." I had seen some of Al's videos, especially the time she had a DP, and I knew Cal was longer than Billy, but Billy is thicker. I have decided, not that I am going to be shopping around for any more cocks, that I prefer a thick shaft over a long one.

Billy smiled. "Now why do I think this is not the only toy you have purchased?"

"Well... I might have bought some more, but let's not worry about that. Let's try this one first." Billy smiled and I realised I had effectively confirmed that I had, indeed, purchased more. By saying 'let's try this one first' there was at least one other. At a minimum.

Billy slipped the cock ring on his already erect shaft and moved the dildo bit back and forth. He then moved it to the top and tried again. "I think the above position may be more comfortable for me, but what you want is the most important."

"Hmmm... let's try doggie with the dildo in my ass." With that I climbed on the bed and assumed the classic hands and knees, ass up position parallel with the mirrored wardrobes. But Billy took the double penetrator off and I frowned.

He gave me a little slap on my bottom and said. "Not so fast, missy. If you think I am going to go straight to the bang to try out this toy, you are mistaken. I want a taste of your delectable pussy first. I also want to see you orgasm at least once."

I smiled, what a change from when we first got together, when he was known as 'Billy the Bang'. A man who thought that, as long as the woman had an orgasm, then he could just get his end away, job done!

I rolled onto my back and spread my legs, I was already wet as both preparing my ass for sex and the anticipation of being double fucked had got me turned up to ten!

Billy climbed on the bed and straddled my hips and we started to kiss, at first little nibbles and then full-on tongue wrestling, before he broke off and moved down to worship my breasts. He worked wonders on them, kissing, sucking and nibbling my nipples whilst massaging them with his strong hands.

I was squirming and coming as close to a tit orgasm as I ever have. There were times that I almost regretted Cal's advice 'Not to screw a woman's ass off, but to screw in on until she screams, let her unwind and do it again until she begs you to fuck her'.

Almost, but there again, all I had to do was beg. "Bill-boy, please, my pussy and ass are waiting." And with that his mouth moved south, down across my tummy and belly button, getting its own bit of loving, and down into my bush. Unusually, for most women, I was as nature intended because Billy said he preferred it that way, and that it added to my aroma, so, apart from some bikini line trimming I didn't shave.

Billy used his thumbs and tongue to open up my pussy lips and lapped up my juices. He then found my clit which he sucked and teased. My hands were in his hair, massaging him but also trying to subtly control his position and pressure.

He then worked three fingers into my sex and curled them up, massaging my g-spot until my hips were bucking. I held him hard on my clit as I screamed, not caring that I might be heard by the new residents living in other rooms in the Guest Wing, not that Rachel was averse to making some noise herself.

Panting and shuddering. "Enough, Bill-boy, enough, I want your shaft in me. I need your shaft in me. I want to be filled in both my pussy and my ass." He eased his fingers out, and with another long lick of my pussy lips from base to clit, he moved away. I rolled, on my second attempt, onto my hands and knees. Billy took up position beside me, so that he was facing the mirror, and after kissing the middle of my back he started to play with my butt plug with his left hand and my tits with his right.

I turned my head to look in the mirror to see him playing with me, but also his shaft sticking out underneath me. As it rubbed my tummy, I could feel how much precum it was pumping out. I reached for the double penetrator and held on to it, determined that Billy would be wearing it. He moved his right hand from my tits to my pussy and his fingers worked on my entrance, but also my clit and I orgasmed again, not as hard and loud as before but still pleasurable. As I came down, I relaxed, and Billy eased my butt plug out.

I passed him the double penetrator which he slid up and down my ass cleft, and I wondered why, but he then eased it into my rosebud. I realised he had slicked it up with the lube that had seeped out when the plug was removed to get it completely ready. He moved behind me, spreading my legs slightly more, but it was making me impatient for us to move on. He removed the dildo from my ass and was doing something. I then realised he was fitting it to his shaft, as I then felt that he was now proudly sporting two cocks and I shivered in excited anticipation.

As he was lining up the dildo on my rosebud, I reached my right hand back to guide his shaft into my sex, as both the dildo and Billy's cock were of a similar length. Once started, Billy gently began to thrust in and out, working himself and the penetrator deeper and deeper, and I moaned in appreciation of how full it was making me feel. When Billy was deep in me, I moved my hand from where it had been guiding him in, to my clit, and I started to play with it. easing my shoulders down onto the bed enabled me to use my left hand to play with my tits.

With me bent over, Billy used his hand to spread my cheeks so he could get both his shaft and the penetrator as deep as he could go as he bottomed out! "You alright Jen-babe?"

"Oh, Bill-boy, so good! So full! How about you?"

"It feels different, and you are so tight! Seeing the probe in your ass is incredibly erotic."

"Then go for it, Bill-boy, bang me!" And with that he started to work his wonders, pulling out and driving back in. I don't know what the stretching of the cock ring was doing to Billy, but the slight delay in movement of the penetrator compared to his shaft gave the sensation of two different people trying to keep in sync.

My orgasm began to rise again, and as I glanced at the mirrors, I could see both cocks glistening as Billy drove them in and out of me. I looked at his face just as he turned to look as well. We smiled at each other, and I gasped and muttered. "How's it feel?"

"The pulling of the ring is alright, but distracting. But in a good way. Nice call on this toy but I wish I could also feel what the probe is feeling." And with that he picked up the pace. He slightly adjusted his stance to get his cock to go deeper. I gasped and pinched my clit causing my vagina to spasm onto his shaft, resulting in a groan from Billy.

He kept thrusting with his rate increasing and his right hand moved around to my clit. I took my hand away to play with my right tit that had been feeling neglected, and I gave the nipple a twist and pull. Having Billy working on my clit always felt better than when I did it, as I didn't know quite what he was going to do in terms of stroking and pinching. Just then his fingers slapped my clit and my orgasm broke with screaming and much more profanity than I would never use in real life.

As I came down, I could feel Billy was nearly about to come. He seemed desperate, and looking in the mirrors his face was clenched up. Then he pulled out, leaving me gaping in both my pussy and ass! Just as I was about to complain, I felt his shaft ram into my asshole, with the dildo running wetly on my back. The extra girth in my ass made up for the loss in my sex, but then he more than made up for it when he curled his fingers into me and yanked on my pussy as he drove himself in and out, groaning and sweating.

And then HE CAME!

He drove in hard and I felt the warmth of his hot spunk filling my ass. He held himself hard in me and I could feel his shaft pulsing as he came. Then he fell back, his cock slithering out of my ass, and he curled up in exhaustion.

It being Friday night, after a busy week, I thought we had had enough fun for the evening and after we tidied and cleaned up we went to bed, nicely sated and looking forward to some morning and evening excitement the next day.

----

Saturday morning, after we had got comfortable, and Billy had given me an orgasm by tasting my pussy, we had more fun with the double penetrator. This time with me on my back at the edge of the bed, with Billy in my ass and the dildo in my pussy. I felt fantastic as not only was I full, but Billy was not just able to work on my clit but also my tits. I was soon screaming my head off again, not once but twice, before he came, flooding my ass with his cum.

We then got up properly, showered and dressed, had breakfast, and went about the sorts of things a normal couple do on a Saturday.

----

At bedtime, I was already in bed, naked of course, when Billy entered. He noticed the other toy, the Dual Rider, on the bed. He picked it up and looked at the attachment point, and then looked at me and smiled. "So I was right, you have bought more than one thing. Any other surprises?"

"Well... if I told you it wouldn't be a surprise, presuming there are any others, of course."

"'Any others,' as in more than one?"

Ah, busted. "Possibly, but let's play with this one, I needed to buy more than one to get free postage."

Billy didn't look fully convinced, but he wasn't going to make a scene about it, not when there was sex on offer. And it's not like I had been spending his money. But to seal the deal I flipped the duvet off me onto the floor before I raised my knees and opened my legs to flash my pussy and jewelled butt plug at him. This had immediate effects on his shaft.

"OK, how does this go on, I presume there were instructions?"

"Well, now that I have something to work with, I can show you." It was more or less a cock ring, like the other one, plus a second ring to go behind his balls. The other thing it had was a wider base where it rests against the root of his penis and the front of the sac, clearly needed due to the second ring.

Having got it on, Billy played with it a bit. "Well, it feels different, and clearly it has to go below me. But before we play with this, I want to eat up that naughty pussy of yours for wanting to play sexy games."

I snapped my knees together, as if I was going to resist him doing that, but he just shook his head and smiled. "In that case..." He turned, grabbed my wrists, and held them above my head. He brought his head over my tits to kiss one and then the other. "I'll just have to feast on your nipples until you beg, really, really, beg me to eat you up!"

Well... I didn't struggle, why would I? Billy quickly was able to use his hands as well as his mouth on my tits. I was stroking his hair with one hand and reaching out for his shaft, which still sported the dual rider, with the other.

Needless to say, I let my legs spread open and whispered, "Billy, my naughty pussy is waiting." With that he quickly moved around the bed and was between my legs, stroking and kissing them as he moved slowly, but relentlessly, towards my already soaking pussy.

So, unsurprisingly, Billy breathed deeply through his nose, smiled and used his hands to open me up before he lowered his head. He used his nose to brush through my bush so that his tongue could lick unhindered along my sex lips and taste my excitement. Then, as always, he said, "Oh! Jen-babe you smell great and taste fantastic."

Eventually, after plenty of teasing work on just my entrance, Billy went to town on my clit. I got really excited and was bucking my pussy up into his face whilst holding his head pressed hard against it. He then worked three fingers in me and curled them up to torment my g-spot. In short order I came, holding onto the sheets to keep me from flying away as I was screaming the place down.

When I recovered both my breathing and sanity, Billy started to work on my butt plug, which actually gave me another small orgasm. He then eased the jewel out, setting it aside and moved his body between my legs. I reached back with my right hand and forward with my left to steer the dual rider into my ass and his shaft into my pussy. Once they were both penetrating me, Billy started to thrust and because of the lube in my ass and the juices in my pussy, he was able to slide all the way in in one shot without any problems.

He then slowly pulled back, not as far as if it was just him inside me, and then slid in again, nestling against my pussy and my clit. The toy felt both similar and different to the double penetrator, and not just because it was below his cock. Somehow it felt more assured, the toy moving at the same time as Billy's shaft, without any delay. Once Billy was comfortable that it was working, he looked at me and asked, "Jen-babe, how's that feel?"

"Oh, so good! The other one felt like there might have been two people, but this feels like it is you, twice, which is my ideal fantasy." With that accolade, Billy picked up the pace of the thrusting. I wrapped my legs around his waist and my arms around his neck.