Higher or Lower

My sister Clare was in a right mess. She was nearing the end of her one-year in London as part of her Law training and was at the end of her finances. She was 22 and had spent most of her £22,000 bank loan and was nearing the limit of her credit card.

I had just finished my medical degree and was chilling before starting my first job in August. We had met for dinner in London once a month and this was the first time she had insisted on staying in and cooking for me.

She wouldn't tell our parents and the bank wouldn't lend her any more money.

I offered to lend her what she needed but she refused point blank. She didn't want charitable loans of anyone especially me. She was planning on doing night jobs or whatever it took to get herself out of this mess.

We were passing the time playing cards and Clare was doing most of the winning as usual. This gave me the idea.

"How about we play this for money?"

"I don't have any money remember." She instantly sounded like a kid again. "I thought you were supposed to be clever."

"Very funny. I'd have thought you'd have jumped at the chance given your run of luck and money problems. Tell you what. We'll set a £50 limit and if you lose that amount I will give you a 6-month holiday on paying it back. So you can earn it. You'll be a high flyer then. What you think?"

Clare thought about this for about 2 minutes and realised that it was a good deal and wouldn't involve a loan. If she won, the money was hers outright.

We played for about two hours. I was still trying to win as I wouldn't be loaning the money, I'd be losing it. Plus I'm an alpha male and didn't want to lose. Whilst we played we drank the wine I'd brought

"That's it. Finished. I'm £50 up. Hand it over Bro." Clare was pleased. It had taken her 2 hours to earn that money off me.

"I'll get my cheque book"

When I handed Clare the cheque she beamed. "You better thing of more ways of losing money to me Bro this is too easy."

I went to the toilet and thought hard. My sister was attractive and I'd always fantasised about her in-between girlfriends when I was frustrated. Maybe I could play this to my advantage. I thought of my knicker collection taken from ex's and housemates from Uni but featuring 3 pairs of my sister's. Maybe I could use this to get a fresh pair of her's, the ones she'd been wearing all day. I'd have to play it cool, I couldn't just buy them of her it would freak her out. I had to be cunning. Then it hit me. I went quickly back to Clare and she was still eyeing up the cheque in her hand.

"You keen to bet some more then?"

Her attention focused on me.

"Hit me, what's the game?"

"Higher or lower"

"Ok how's it going to involve money?"

"Well I know you can't afford to lose that money you've skilfully won of me so I've been thinking. What do you have lots of and could afford to lose some of?"

Clare looked puzzled.

"Clothes."

"Clothes? Hmm I guess I have quite a lot. You want me to gamble my clothes against your money? Which ones? I've got all sorts... Hang on. What you going to do with the ones you win? You hoping to make a drag outfit or something or sell them?"

"Sit and listen."

Clare slipped the cheque in her jeans pocket and looked focused.

"There's money involved here and you need it. Its up to you how much you're prepared to gamble. You know how much ...."

"Yeah what ever I'm a big girl what's the deal?" I know I would have to be quick and sell this well. She's had some wine but this was still dangerous ground.

"Ok, we will be playing for the clothes you're wearing one at a time. For example we play 50p a card for one of your socks. I turn the first card over (I demonstrate this), it's a 4, I ask higher of lower, you guess right we move on and you earn 50p for each card. There are a lot of cards in this pack so even at 50p there's a lot of money on offer to you. But importantly you can stop at anytime and keep the money and the item we're playing for. So you have to say stick for that or twist to keep going. We take it in turns to pick which item we play for."

"So if I guess wrong. You get that item for the amount of money we're on right?"

"Yep, it could be less then you paid for it or many times more."

"Who decides the value of each card for the said item?"

I looked surprised.

"Fair question isn't it?"

"Yes... just surprised how much like a lawyer you sound." We both laughed. I think it helped the mood.

"We agree it beforehand like adults."

"If I gamble using an item and stick with my winnings can I choose to regamble it at a later stage?"

This was a tough question til I realised that a 'no' would make it harder to win her undies and I'd simply end up with expensive socks.

"Of course, but it has a fixed price second time around of 50p a card."

"That's fair."

"You in then? You want to gamble your clothes?" I regretted that statement before it had even fully left my lips. I'd just spelt out what she was about to do in a way that didn't make it sound like a good think to do.

"You bet. Left sock- 50p a card, like you picked, lets go." What a relief.

We were sitting opposite each other with a coffee table in front of us. I cleared it and dealt the first card. Clare was on the edge of her seat. It was an ace. Clare looked bemused again.

"Is that hi or low then?"

"Emm. I don't know. High?"

"Ok. Low then." 7 was next.

"I'll go high".

I turned over a 4.

"Right. So that's £1 then for your left sock. Hand it over."

"You want the sock now?" Clare seemed unsure.

"Well its mine now isn't it not yours."

"Money first."

"I think I'll pay this one cash but it will have to be cheques later though."

I took Clare's sock and placed it beside me. I started shuffling the deck.

"What next Clare? The other sock?"

"No. We'll go for the cardigan. It's worth £30. £3 a card then?"

"£2.50"

"Ok. Lets play."

The cardigan cost me £12.50. Clare wasn't pleased.

"Bra - £7.50 a card" I said. I hoped this would encourage her to continue.

"Deal."

I was £60 down when Clare called stick and retained her bra and pocketed her cheque. She looked a lot more pleased with herself.

"My term. My top. £5 a card?"

"£4.50?"

"Ok"

I won the top for £18 and watched Clare slip her top over her head. I enjoyed the view of her black bra.

"So how much do you have then now?"

"Lets see, £91.50 plus the £50 from before."

"Good way to make money this hey?"

"Yeah though I need to make more. Lets play for my trousers. I want £10 a card."

The money was getting serious now.

"£7.50, its not worth more than your bra."

"Yes it is I paid over £20 for this, £9 then."

"Ok".

Another £60 got me Clare's trousers and had her sitting there in her light blue thong (at least it looked like one from the front), her black bra and her right sock.

"Hold on. My cheques are in my jeans." She reached into the pocket and looking for somewhere to put them settled with tucking them into her knickers waistband.

It was my pick. I desperately wanted that thong but knew to pick it now would give my intentions away. I looked my sister up and down. She looked back at me biting her lip. Clearly interested in my choice.

"I'm just going to the toilet."

Clare looked disappointed to be kept waiting. I had a dilemma here. If the other items cost me a fortune she might stop playing and I might not get the chance to win her thong.

When I returned Clare looked impatient.

"Come on what's it to be, time is money and all that."

"Ermm."

"Wrong answer, you've had too long to chose, my turn."

I shrugged and took a sip of wine. At least it spared me making a bad choice. She timed it to perfection, just as I was about to swallow."

"Thong- £20"

I spurted my wine out of my nose.

"You alright?"

"Yes. Just wasn't expecting that choice."

Clare smiled.

"I know"

First card was a 2.

"Higher then"

3

"Higher"

Queen.

"Lower"

Jack. I took another sip of my drink.

"Lower"

7

This was it. Clare was given her first difficult choice. She would surely stick and take the money.

"Lower."

I was startled.

"Lower- you sure?"

"Yes, lower."

6

Damn. I felt my cock stir for the first time.

"Higher"

6.

"Oh what does that mean?"

"Erm I guess you win it. Its not lower is it?"

"Ok I think I'll stick with that. That's £120 thank you bro."

I wrote the cheque and Clare took great delight in tucking it her thong.

"I think these might have to be my new lucky knickers."

Clare's sock was the only unplayed for item left but I wasn't going to play fair now with her being so smug.

"Bra- 50p now"

"Oh yeah ok."

I turned over a 7.

Clare gulped. The smile disappeared from her face.

"Higher"

I turned a 4. I was going to see my little sister's tits. Clare moved her hands behind her back and unclipped her bra. I watched it fall down her front and admired her firm proud breasts. She handed me her bra and I handed her another 50p in cash.

"Sock? 50p"

"Sure- not worth anymore is it?"

And indeed it wasn't. I got it for a pound. Clare seemed disappointed. I guess she realised that she only had her lucky knickers left and they would only make her 50p a card. I wondered whether she would end the game now.

"Lets play for my lucky knickers then. Come on knickers. Make me some more money. You don't want bro to own you do you."

I laughed.

Then it got interesting. Clare went on an amazing winning streak. 20 cards later and I was beginning to get suspicious. Clare was taking an amazing risk considering how little money was on offer and the consequences if she lost. Then I remembered that I hadn't shuffled the pack since I went to the toilet. I didn't let on while I considered my options. I suspected that she had fixed the pack so I waited a few more cards then I slyly dealt a card from the bottom of the pack. I watch Clare's face. The shock was there. She had cheated and couldn't see why her plan had failed.

I handed her the cheque and Clare slowly took the others out of her thong and placed them together beside her. She stood up and turned from me and pulled her thong down and stepped out of it.

"I need the loo". Clare left quickly without turning round so I didn't get even a small glimpse of her pubes. Had this gone too far I thought? I totted up her earnings. £307 for her clothes plus the £50. She'd done fine. I waited expecting Clare to return fully dressed but she naked and I was able to admire her neatly trimmed pussy. I smiled. Clare sat on the sofa and spread her legs wise so I had the best view of her pussy. I certainly wasn't expecting that or what she said next.

"I'm not stupid Sam. You wanted to see me naked and add these knickers to the ones you've already stolen off me, don't look shocked I've known for ages, so you used this game and your money to get it. Well done but now's the time to get serious if you have the balls."

I paused for a minute.

"I'm listening"

"Bigger money for bigger things. I mean hand jobs, finger fucking whatever you want to pay for, I'm game."

"Ok. I have the balls." I decided to call her bluff. "£100 a card to fuck you from behind." I paused and watched her face. She didn't look shocked but seemed to be weighing up the pros and cons.

"In for a penny, in for a pound. Lets make it £200 to fuck me up the arse from behind."

She looked me in the eye. This was big money. I wondered if she was calling my bluff now.

"Deal." It was too good an opportunity to miss out on even if it meant I couldn't go out for the rest of the year. It wouldn't matter because I could just sit at home and wank thinking about this!

"Good, it will be my first time you know."

I smiled. I was going to take my sister's anal virginity. I turned the first card, it was a 7. Brilliant start. I had practically 50:50 chance I could do this for £200.

Clare gulped.

"Higher"

"You turn it over"

Clare slowly reached over and turned the card so she could see it and I couldn't. She looked up at me. Our eyes met and we held each other's gaze for what seemed an eternity.

"It's a 7."

My heart skipped a beat.

Clare smiled wickedly. "I'll go higher again please bro."

I turned over a jack. This was getting expensive.

"Lower"

I turned a 10.

"Lower again."

9. So close. £800 down.

"Lower." Clare looked up at me. "Don't look so worried bro, if it takes the whole pack to get your wicked way with it will still be worth it. There can't be many men outside Texas who have fucked their own sister."

"Yes but what if you make it all the way through the pack?"

Clare laughed. "If that happens we'll go find a prostitute who looks like me and I'll pay for you to fuck her arse."

I smiled. "Lower did you say?"

Clare nodded. I turned the card and beamed. It was a 10.

I looked up at Clare and she beamed back at me.

"Write the cheque and let's do it bro!"

She stood up and walked around the back of the sofa and leaned over it arse in the air and legs spread. Wow I thought. She's actually keen. I wrote the cheque with my hand shaking and placed it on the sofa in front of her. Clare looked at the amount and seemed pleased. I stripped off quickly and Clare nodded her approval at my hard cock. I walked around slowly and admired the arse my sister had presented to me. I ran my hand over her cheeks and she quivered. I licked two of my fingers and inserted them into her wet pussy and slowly started to finger fuck her. She moaned loudly and the sound it made was amazing. I started to produce saliva in my mouth and spat it on to Clare's arse hole to start lubing it up. I removed my fingers and smeared her juices over her arse too.

"Well that's you ready time to make me ready"

Clare turned her head and I saw the puzzled look on her face disappear as I penetrated her juicy pussy in one easy motion. She understood as I gave her 10 slow long trusts of my whole length.

"Good idea bro, cover your cock in my juices 'cos my arse is going to be ...."

She didn't finish the sentence. As my 10th thrust entered her she came hard. Her whole little body (she's only 5.5" and about 7 stone) shook furiously with my cock deep inside her. My little sister was a screamer. The noise was incredible. The after shocks of her organism lasted 10 minutes. I held my cock in position and watched her shudder every few seconds on my cock. Her face was flushed red, as was her chest.

"That was incredible. That's the best organism I've ever had." I smiled and pulled my cock out to more moans from her. I repositioned my pussy juice covered cock over her arse whole and entered my sister inch by inch. I pushed the final inch inside her and it happened again. She came just as hard as before with no thrusting. When it settled down she was gasping for breath and couldn't talk. I was pleased I was having this affect on her and that I'd managed to control my own orgasm. I started to fuck her arse and Clare had to grip the sofa tight. I used long hard controlled movements and my little sister responded by pushing her arse back against my cock. I carried on the same way for 45 minutes, only pausing twice for my slutty little sister to have two more orgasms with my cock deep in side her arse. I was very pleased with my stamina and was beginning to think that the money it had cost me to get in this situation was well spent.

"I need it harder Sam. Harder please. Please fuck me as hard as you can." This was great. My sister was begging for more of my cock. I decided she better have more. I launched into hard fuck mode and began pounding her arse hole at a rate of knots. I lasted 15 minutes of pure porn star arse fucking and sweat was dripping of both of us and Clare seemed to be in a state of continuous orgasm for the last 5 minutes. I finally emptied by bollocks into her rectum and happily withdrew and wiped my cock on her arse. I need not have bothered as she turned and gobbled my cock into her mouth to give it a nice wash.

"Well that was fantastic. Well worth the money. You better keep out of financial mess for a while Clare cos I'm going to be a bit short for a while now." Clare removed my cock from her mouth.

"I feel really bad Sam."

"How come? Because that was incest?"

"No I don't care about that. Taking all this money of you. The clothes are hardly worth anything and really I should be paying you to fuck me not the other way around. I'm just a tight hole, you're the one with the talent."

I laughed at this.

"Don't worry. Think of it as me simply helping you out with money like when we were young only I don't want paying back"

"Well I am worried. I'm going to call one of those girls in the phone boxes and see how much they just for anal and half it. Then I can work out how many times you have to fuck my arse to get your money's worth."

"You don't have to..."

"Yes I do and I'll do it for half the cost of the local whores so I know I'm no better than them. I was silly to get into this mess and I'm luck I have a helpful brother. Anyway I do like you fucking me so its not like I'm not getting something out of it either."

I laughed.

"You might not be able to sit down by the time you have repaid me." Clare smiled.

"Good! It will mean I'll be the best fucked girl in London and definitely the happiest!"