A deal with Lucy

I guess everyone has been in a relationship that was going nowhere, but they were too lazy to break up.

That’s where I was with Lucy. But I can’t say it was difficult to stay with her, either. I stayed with her for the same reasons I noticed her in the first place – namely that she was smoking hot. Slim, blonde and petite at only 5’3”, Lucy attracted attention wherever she went. She was also unfailingly kind, generous and loving. So it hurts me to say that she really only had one big failing – and you’ll think I’m being unkind here – but she was really not too bright. I know lots of people will think that they could live with that, no problem. But when you actually live with someone like that for 3 years, little things begin to grate.

Little things like her conversation. She took zero interest in current affairs, and probably wouldn’t even be able to name a politician. She took zero interest in travel, and was happy to revolve her in own little world – the same circle of friends, the same places, the same conversations. In fact she took zero interest in many things, and I quickly came to realise that she had only very limited ambitions for her own life. She would probably have achieved everything she ever wanted once we married and had kids. Not only that, even these limited goals weren’t something she’d thought of herself, but just something she saw other people doing.

After 3 years together I still found her attractive. But, not surprisingly, our sex life couldn’t really be described as adventurous or imaginative. I would have liked it to be, but that was probably ambitious when only one of us had an imagination. Instead we settled into a routine of standard “missionary position” sex when Lucy wasn’t too tired. You’re probably thinking that with someone so hot that this wouldn’t be a chore, and it wasn’t. But that really was the extent of our sexual repertoire – anything other than me climbing between her open legs and poking her as per our usual routine was too dirty, not nice or would “gross” her out. So we settled into a regular pattern – she seemed to enjoy it, I enjoyed it – and nothing ever changed.

That’s how things stayed for three years. I was dissatisfied, but Lucy thought we were in a “stable relationship”. I guess we were – we rarely argued and we had a good life. It’s just that we were very different people. But In Lucy’s world what happened after a “stable relationship” was that you got married and had kids. Not being very bright, her plan to achieve this next step was childishly transparent. She began pointing out friends or acquaintances that were married, and describing how happy they apparently were. She began slipping in references to how long we had been together. And she began pointing out the advantages of us being married.

We were spooning in bed one Saturday morning when Lucy resumed her campaign. My arms were wrapped around her body and my face was pressed against the back of her neck, with my nose buried in her hair. In the borderlands of sleep and waking, her smooth, tight body fitted perfectly cradled in mine. I felt very content, and right then it wasn’t actually difficult to imagine us being a married couple. My arm moved up and cupped her breast, stroking her impossibly soft skin. She murmured something, and I felt my own lust rising. Gently, with one finger, I stroked one nipple until I felt it harden to my touch.

I leant over further so that I could whisper in her ear: “You just have…..the most gorgeous body”.

I said it because I knew she loved to hear it, and it turned her on. And also because it was simply true. Lithe, smooth and petite – she was truly gorgeous.

I watched as her eyes opened and her lips formed into a smile

“Well it could be all yours if we got married, you know” she replied.

Right then it was a very attractive proposition. My hand moved back to her breasts to stroke them.

“Including these?” I asked teasingly. She knew very well I loved her tits.

“All yours!” she told me

As slowly as I could, my fingers traced a gentle path from her breasts down her stomach, until they reached between her legs and settled on her pussy lips.
She opened her legs slightly and I nudged one finger inside her slick little pussy.

“And this? Would this be all mine if we married?” I asked

“Whenever you want!”, she giggled happily.

I moved my finger gently inside her. She was very wet now, and I could smell her cunt. I knew I would have to fuck her in a moment, and in my lust a new idea came to me.

My hand glided from her pussy, across her waist and gently cupped her bottom, just one cheek.

“What about your bum?” I asked softly

“That too” she replied again, but a little primly and less sure of herself now.

I knew why. Right at the start of our relationship I had wanted anal sex, but Lucy had been horrified by the idea. It was “disgusting” and she wouldn’t even talk about it, making clear that the subject was never going to up for discussion. And there we had left it for 3 years. Now she wasn’t sure whether I wanted her bum in quite the way she thought.

Now seemed like a perfect time to test her. I kept my hand on her bottom, then using the finger still wet from the juices of her pussy I wiggled until I found the puckered little entrance to her arse. Her whole body stiffened suddenly in response, but she said nothing and she didn’t move away.

I waited a fraction. She knew what was coming next. So I said it: “And this?”

She didn’t answer, even as my finger rested on her arsehole. I knew that she was torn because her simple end goal – marriage – was so tantalisingly close. She didn’t know what to say, so I thought I would help her out.

“Let me do this, and you’ll have an engagement ring on your finger by the end of the day. You can even pick the ring while we do it” I said.

I knew picking the ring would be an incentive because Lucy kept one of those department store catalogues by the bed – a thick volume full of low quality tack mostly imported from China. It had a jewellery section with about a dozen pages devoted to rings, of various quality starting with total crap and gradually ascending to just average. At some time Lucy, I had noticed, had bookmarked a page of the average rings by bending a page corner over. I assumed that she had made her choice of engagement ring already, as part of her grand plan. But fucking her up the arse while she made that choice again suddenly seemed like a great proposition.

I could see from Lucy’s face that she thought it could be a reasonable proposition too. Her face was completely transparent – you could see the range of emotions going through her mind: the expectation of finally getting the ring, through to the dismay of what she’d need to do. She said nothing while she thought things through – slowly. Finally she said:

“You’re serious? You would get me a ring? Today?”

“Absolutely serious. We will go get the ring this morning” I replied, and I meant it.

She studied my own face for a long time, eventually satisfied that I wasn’t joking. Then, she thought of a flaw in the plan:

“Any ring in that catalogue? I can get any ring?” she said suspiciously. I could see that this was the deal breaker. She wasn’t going to do this for any cheap rubbish from the first page. Then a crazy plan popped into my head.

“Here’s the deal”, I said, laughing. “When I’m an inch up your bum you can choose any ring on the first page….”.

“What? The first page!” she began hotly

“Wait! Wait” I interrupted, laughing harder. “You haven’t heard the rest of the deal. Every inch I go in, you get to turn the page”. It was a plan so strange I couldn’t help laughing.

Lucy wasn’t laughing. But looking at me laughing, she began to suspect I was joking again. She started to frown, and sensing that I was starting to lose the deal, I explained that when we got to page 7, she could choose from any page she liked.

“And that’s my final offer. Take it or leave it. Let’s do it, and you can be wearing that ring in an hour. I’m serious, and I give you my word.” I told her.

Lucy thought it through. She did at least know that I wouldn’t go back on the deal. Then without a word, she skipped out of bed and out the bedroom. I saw her bare butt disappear into the bathroom and then she closed the bathroom door. I heard movements inside, a cupboard opening. I realised that she’d probably gone to get some Vaseline for the occasion and was right now lubing around her arsehole. Then she darted back into the bedroom (she didn’t even like me seeing her naked) and rejoined me in bed.

She watched me intently with a serious look on her face.

“Go slow, ok? And stop if I say so” she told me quietly.

“I promise” I replied. “Are you going to grab that catalogue?”

“You’re serious about those pages?” she asked disbelievingly. Then she shrugged and took the catalogue from the bedside table, opening it up at the jewellery section.

“Not yet, first things first. That’s the deal!” I reminded her, and closed the catalogue again. Then I coaxed her to lay on her front with her bum in the air, and climbed between her legs, pressing myself against her back. With one finger I explored between her bum cheeks until I found the little puckered hole there. I had been dead right, she had lubed herself up already.

Lucy lay with her face into the pillow, clearly not looking forward to what was coming. She said nothing, but I was so excited that it seemed my erection was harder and bigger than it had ever been, almost painfully large. I don’t want to boast but erect I’m at least 7 inches, and very thick. Lucy’s build was very petite. For a moment I started to worry myself that I would hurt her.

I manoeuvred my prick into position, until I could feel the wetness of the Vaseline she had applied. Underneath me, Lucy’s whole body tightened reflexively. As slowly as I could, I push into her butt and felt the soft flesh part around the head of my cock. Lucy grunted, and gave a long breath out. I pushed my cock just barely into her arse and then stopped. She felt so tight that I didn’t think any more would go on.

“First page!” I whispered into her ear.

There was a pause, then Lucy propped herself up enough to open the catalogue. She didn’t seem too worried at this point. With my head of my prick still embedded in her bum, she flicked through the catalogue until she came to the first page of the rings. I could see her book mark of the ring she really wanted about a dozen pages on – a long way to go yet. The page we were looking at just contained cheap tack worth less than $100, nothing you’d want for an engagement ring.

“Nothing from this page, then?” I asked her

She shook her head, didn’t say a thing. So I pushed on into her. I hadn’t even made the next inch when she gave a squeal of pain:

“Oh god, that really hurts. That really hurts. You’re too big, you’ve got to stop” she protested.

“I’ve stopped honey, don’t worry – just relax” I told her. I stopped pushing but I kept my prick in her.

She was breathing heavily now, still with her face buried in the pillow. I waited and gradually her body grew less tense.

“How about we call this pages two and three?” I offered.

She said nothing, but again propped herself up and flicked the page. She didn’t even look at the double spread of rings, but buried her head again. But the progress seemed to encourage her: she was three pages closer to her goal. So softly that I could barely hear her, she told me to carry on.

So I did. I pushed deeper into the tight little hole and felt myself enclosed by tight warm flesh. She grunted again but her body was not so tense. We made it to about three inches and I stopped once more.

“Pages four and five” I announced.

Again she flicked the page over to a new double spread, but didn’t even glance at it. Then she settled back into the same position.

Taking this as consent I pushed again, but this time less carefully than I had before. Feeling overconfident I stabbed her up the butt with probably two inches in one movement. Shocked and in pain, Lucy cried out. Her face shot up and I could see a solitary tear running down one cheek. Her breath came in rasps now. I felt bad immediately, and thought about pulling out.

“Sorry” I told her “Do you want me to stop?”

Lucy’s breathing calmed slightly, and she considered the offer.

“No” she said finally. “We must be nearly done, and I want that ring”.

We were indeed nearly done. Two more inches and I would be totally embedded up her arse.

“Listen”, I said “Let’s change the deal. How about I just do the rest really slowly and then you choose the ring?”

She nodded, and as slowly as I could I pushed in. The next two inches went more smoothly this time, and I marvelled at how her tight little body managed to accommodate my fat prick so deeply. Finally my balls were pushing against her cunt lips – I was completely in.

“That’s it” I told her, “Do you want to choose?”

Without saying a word, she flicked a few more pages until she came to the bookmarked one and then pointed at a great, fat, diamond studded engagement ring at the bottom of the page. It was very expensive.

“That one”, in a tone which didn’t invite argument.

I hadn’t actually realised the rings got so expensive. This would have to be worth it.

“Remember, if you’re wearing that ring your body’s all mine. All day, every day. You promised” I told her.

“I know that” she replied.

I pulled out of her arse very slightly, just enough to admire the tightness of her arsehole – so tight it dragged out slightly as I withdrew. Then I gave a little push back in and immediately pumped her body full of hot cum, the longest, biggest orgasm I have ever had. It felt like I would fill her body up.

When I finally pulled out in a great slurp of semen, I noticed with interest how her tiny arsehole was still distended and gaping. A trickle of cum ran down from it and settled into the hairy confines of her pussy. I felt full of desire for her. I wished I could have stayed in bed with her all day.

Lucy, however, had other plans. With a grunt of pain from her sore bottom she pulled herself upright and rummaged in a drawer for some panties. As she pulled them on I imagined my cum settling inside them in little pool from her arse. I would have to investigate later. But not now –

“Get up! We’re going shopping” she announced brightly.

(To be continued)

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