Sister in Law's Sex Games

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My sister in law sets a holiday weekend challenge.
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This is the incredible story of the most amazing holiday weekend of my life. A couple things to note: a) that my wife's family is loaded b) they were very close - particularly when alcohol was involved. They have a number of holiday homes, one of which we share regularly with her siblings and parents. Their amazing beachfront mansion with views over the Pacific Ocean was the setting for a non stop fuckfest with the two hottest women I know - my wife and my sister in law.

To introduce our participants - I'm John - 35 year old sales rep for a large tech company - just a regular college educated guy you'd never notice in a pub or club. I have had my fair share of partners and sexual experiences and never had complaints. In all honesty I agreed with my wife JJ I need to look after myself better and was carrying a couple extra pounds. My dick is a decent 7 inches when hard, but I had received more than a few comments on my substantial girth - which honestly I was proud of.

My wife of 6 years, JJ (Jennifer Jane) was definitely the knockout of the couple - she was a year younger than me but looked at least 5 years my junior and turned heads. She had an amazing set of 34C tits, a really tight arse and stunningly long legs wrapping up her 5 foot 11 frame. Her brunette hair was halfway down her back and normally in a low ponytail or left out. I loved it when she wore it out as it outlined her amazing face perfectly. Not only was she beautiful she was incredibly intelligent, sharp witted and dedicated. Boy could she tell a story. She works as a senior executive in a real estate development company where she was on the fast track to superstardom.

The third in our trio was JJ's younger sister Sam (Samantha) - she was the black sheep of the family. Never went to college, and went straight to work as a hairdresser, then an actress, before settling on becoming a masseuse. Money was never an issue (the loaded parents thing), and she had a run of dud boyfriends (and occasional girlfriends) in the time I'd known her. She was currently single and travelled a lot and was making noises about wanting to become a stewardess on a private jet company. She has amazing blond hair, she's about 4 inches shorter than JJ (a constant source of sibling disappointment as they couldn't trade outfits) but had the most spectacular set of 36DD breasts. Sam had assured JJ they were real, but even if she had some work done but they were still perfect. She loved to flaunt them too - bikinis, crop tops and sundresses were common occurrences for my sister in law. Sam also hated wearing panties - something she was oddly vocal about - if she was wearing them it was a thong and was almost certainly complaining about it. But she was fantastic company, another great talker (and equally great listener) and always the life of the party.

The holiday home was huge; 5 bedrooms and bathrooms, an amazing kitchen and dining room overlooking the ocean, huge living rooms but the real highlight was the cascading decks that wound down to the Pacific. On the biggest one which adorned the master bedroom and main entertaining lounge is an amazing 6 person hot tub spa with an adjacent sauna and large pool.

It was a long weekend and we agreed that a family get together would be a welcome retreat after a busy couple months. Sam arrived early in the afternoon and by time JJ and I arrived just before 6pm she had champagne on ice and dinner prepared. We chucked our bags away and got straight to dinner. The beers, bubbly and soon enough cocktails were flowing and eventually I suggested a swim and spa might be a good option before we passed out on the couches. JJ and Sam both agreed it was a great plan and rushed off to get changed.

I followed JJ into our suite (room doesn't do it justice) just as she was extracting a new very small pink and purple bikini from her bag. As she was changing I noticed she'd freshly waxed her pussy into an even thinner than normal landing strip. She must have ducked off at lunchtime as it wasn't like that when we fucked last night. I should mention JJ and I have a fairly adventurous sex life - we had sex at least twice a week and openly shared and even acted out some of our fantasies. I made a comment about how amazing she looked in the bikini - she thanked me with a passionate kiss on the lips and said that her and Sam weren't sure if bathing suits were allowed in the tub. I pondered it for a second as the spa was originally my idea, then figured she was just talking about the lint in the filter and nothing more sinister. I dismissed my suspicions and chucked on my smallest swim trunks and rushed out to the deck.

Sam was obviously taking a bit longer to get ready as she wasn't there when we got back. We both slipped into the tub and immediately enjoyed the heat and soothing bubbles. We were annoyed that we'd left our drinks inside, until JJ remembered the outdoor kitchen had a drinks fridge, which Sam had fully stocked up. I poured 3 glasses of champagne handing one to JJ and leaving one on the table for Sam.

Sam arrived about 10 minutes after we did. I swear she looked a bit red and flushed in the face, but my gaze was soon diverted to what she was wearing. It could only be described as 3 tiny triangular pieces of thin see-through black material held together by some equally tiny string. Those pieces of string were earning their keep as they held up Sam's massive tits. I was pretty sure she was fully waxed downstairs as the bottom fabric wasn't covering much. I could just make out the markings of her pussy lips and her arse was fully on show. A simple "Wow" was all I could muster, JJ was up to the challenge and gave her sister a rousing "god I wish I had your rack" to which Sam replied "I'd trade for your legs any day ". Sam grabbed her drink and slid into the tub.

After a few rounds of drinks, JJ suggested we should play a game to pass the time. She had seen something on "Taskmaster" and thought we could modify it for home. Essentially it was a low stakes game of 'bluff'. The jets in the spa had made it impossible to see much below the surface, and Sam suggested we play 'fists or flats' whereby someone either made a fist or left their hand flat and dropped it under the water within 10 seconds and one of the others had to guess if it was a fist or flat. The third person would be the referee and place their hand on the player's to make sure they didn't change or cheat. We took turns and Sam was the first to guess, JJ had to make a fist/flat. That made me the ref. I slid closer to JJ and cupped her right hand. It was definitely flat but as I touched it she slid both her and my hands close to her inner thigh. I could feel the heat as our hands rested on her bikini bottom. Sam incorrectly guessed and JJ got a point.

We swapped around for a bit and eventually it came around to me being the ref for JJ guessing about Sam's hand. I slid nearer to Sam and felt under the water and found her fist. It was resting on her bikini bottom and as I cupped her hand, her free hand gently rubbed my wrist before directing my hand to the top or her underwear, and then used my hand to trace her pussy lips. She finally used it to put pressure on her clit through the shear fabric. JJ seemed oblivious but didn't seem in a hurry to make her guess. She eventually guessed correctly and Sam made an off hand comment about "the last time she tried fisting was in her lesbian phase" which we chuckled about.

Sam then took it up a notch by suggesting a variation. We would each have 1 minute to either lose our swimsuit bottom or pretend to. We could use the minute to give the appearance of losing clothing in the hope the others fell for it. The others would then have to guess if they were bottomless or not. If you were correctly guessed you had a sit on the side of the tub naked. We all quickly agreed and thought it sounded fun. It was a challenge deciding what to do but I eventually settled on losing my pants. I set about making a big show of it in the hopes they would think I was over acting. Just before the minute was up I slyly slid off my trunks and sat on them so they wouldn't float to the surface. I was trying to watch JJ and Sam while dealing with my own trunks, but was pretty convinced Sam was bottomless (she hated anything resembling panties) and JJ not - but much less confident on JJ.

Both girls fell for my trick but I only then realised that I would have to prove it by standing up. I stood up and exposed my semi hard dick to the others. There was a brief round of hollering and some comments from both. My dick softened slightly as it went from the warmth of the spa to cold of open air. I felt better about being naked when I realised JJ was excited by this, and Sam was clearly planning something. It also occurred that very soon one or both would be joining me in the buff.

I correctly guessed Sam's status, and she who shot up like a rocket and lost her skimpy black top too. She made a show of flicking it at me. Seeing her exposed breasts for the first time was absolutely magical. Due to its size the bikini top hadn't been covering much, but they were the most amazing set of nipples. Slightly darker than my wife's but the perfect size; and rock hard. My wife repeated her earlier refrain of "sooo jealous of your tits sis" - Sam took the compliment gracefully and attention turned to JJ and whether she taken her bikini bottom off.

We had split opinions. I'd said "no", Sam thought "yes" - but we had to get a consensus and Sam deferred to me - and I was very wrong. My wife stood up completely without panties on and laughed at me. She then pointed to a tiny pink string protruding from her pussy lips. She said she wasn't sure how to hide them so stuffed them inside her pussy. As I was the false accuser JJ demanded that I be punished and that the punishment should be retrieving her panties only with my mouth. I was keen but not sure how keen Sam was to watch. I should never have doubted as she grabbed another bottle and settled in for the show. I made a complete spectacle of it - we'd fooled around with people watching previous so I knew how to drag something out (in this case both literally and figuratively). Even though the bikini was pretty small and JJ was clearly wet I took ample time on her clit and outer labia before latching the strings with my tongue and removing them completely. It wasn't lost on us that both Sam's hands disappeared below the water and she was gently rubbing her own clit and pussy.

Eventually all loose garments were removed and we all sat there excited. Sam said she had an idea for another game - and i was the intended target - but first she wanted some snacks. She disappeared to the main kitchen, and I took the opportunity to check in with JJ. She told me she loved me and I could go as far as I wanted this weekend. She said she wanted to try a few things out as well and who better than with her smoking hot sister.

Sam returned with supplies and launched into the rules of her game. Essentially I had to jump in the cold pool and stay there until my dick was completely flaccid. We would then see how long it would take me to get a full erection. I had to honestly say when I was hard and everything had to stop. Sam suggested 3 rounds - Solos, Duos and Trios. Round 1, Solos was me playing with myself; round 2, duos me and my wife, and round 3 trios - me and both girls. Sam said whatever group was the slowest would be those involved in getting me off (4. the prize round). The only rules were "only hands may touch the dick" and "those not involved in the round were not allowed to touch John", but could do whatever they wanted away from me. This meant I needed to try to last as long as possible with two gorgeous women giving me handjobs or risk just ending up jerking off myself. It was part torture and part three way fantasy.

We agreed and I dived into the pool. The cold hit me like a truck, and my testes rushed up into my body. My dick was smaller than normal. I rose quickly from the pool and started fondling my dick. I was laser focused on getting myself as hard as possible as fast as possible. I'm pretty sure JJ and Sam wanted to be involved as they were both busy stroking their own clits. I did notice their legs intertwined and overlapping and a degree of 'helping each other out'. Mutual masturbation was a real fantasy of mine and the sight of the others brought red hot heat into my body and balls and I was hard in no time. I called time and it came in at 3 minutes 15 seconds. I don't think it would have taken much longer to blow my load.... But JJ and Sam also had to stop - both just short of their orgasms. I found out later that Sam had a secret 'Ruined orgasm' kink.

Round two followed immediately and i jumped back in the pool. This time JJ could help. She was an expert at (and loved) giving head and normally skipped handjobs but that wasn't the rules here - hands only. The freezing pool took much of my manhood away so I swam around a bit. I did enjoy a good skinny dip, JJ asked if she could join me but I said 'no' as the time started when I exited the pool.

As I got out, JJ met me with a passionate French kiss and her tongue massaged mine. I was surprised as I thought it was handjobs only, but JJ pointed out this was Taskmaster based and there the rules were there for literal interpretation. One of JJ's

hands lowered to my cock and cupped my balls and while the other she inserted into her pussy. She eventually removed it and used her flowing juices as lube to get me hard. The whole situation was incredibly hot and I was rock hard in no time- or 2.59 to be exact. This meant that it was either going to be me flying solo or a three way in round 4.

The third and final round kicked off immediately, so I dived back into the freezing pool. Both JJ and Sam could help this time, and I noticed they were developing a strategy (or at least there was a lot of giggling). I really wanted this to be the slowest and I was confident it would be. I walked back to the spa and jumped in. Immediately JJ grabbed a champagne bottle and took a big swig, she then proceeded to kiss Sam and in the process transferred the champagne to Sam. After that she poured champagne over Sam's luscious breasts and naked body like something straight out of "Wild Things ". She then slid the neck of the bottle into her pussy. I could tell she was super wet and keen to ramp things up. This was obviously incredibly arousing and I was rock hard in 2.30 flat. Just as the champagne bottle took JJ to her first orgasm of the night Sam called time. She declared it time for round 4. So despite having two horny and gorgeous women there I was forced to jerk off alone.

Given what I'd just witnessed I was about ready to shoot my load. I took JJ's champagne bottle, smelling strongly of her pussy, and took a swig. I made eye contact with Sam as I stroked my dick; she licked her lips and gave me a come hither look as she fingered her clit ferociously to a shuddering orgasm on the side of the pool. I waded over to her til my dick was right in her face and then felt the unmistakable feeling as my balls twinged up. I was dying to come all over her tits and did just that, shooting rope after rope onto her melons and lower belly. JJ, who loves the taste of cum swam over and licked it all up so it didn't drip into the spa. She made a show of starting at Sam's pussy "just in case" and working her way up much to Sam's joy. She then opened her mouth and dropped most of the cum into Sam's mouth and tongue - they then simultaneously both swallowed. Technically the game had finished so we got some fresh drinks and took a break.

Sam then suggested a more traditional party game of "I have never". It seemed tame based on what had just gone down but we agreed. Sam started - I thought maybe she didn't know the rules as she kept saying things she'd done a lot. Her and JJ rattled though 'kissed a girl', 'skinny dip', 'nude run in public', 'masturbate with other people', 'play strip poker', 'truth or dare', drinking each time. It was my turn and said "I have never eaten own my cum"; the girls sought clarification on how to apply that and I said it was about tasting themselves during masturbation or sex. Sam drank but JJ didn't which I thought was interesting.

Sam took charge again and listed 'sex with three or more people', 'eaten pussy' (we'd all done that), 'fucked something inanimate (excluding sex toys)', 'sex using food', 'have anal or be pegged'. I nearly spat my drink at the pegging - I didn't mind the occasional prostate play but nothing too big. JJ chipped in with 'a cumswap' and 'fucked blindfolded'; i cheekily added 'cumwalk' and 'being fucked air tight' - the first things no one had done, and then really wanted to know how far Sam had gone previously so said 'fucked a stranger for money'. Sam (and JJ) both hadn't.

By this point we were absolutely trollied and out of ideas, and Sam loudly shouted "Surprise!!!" and reached into the kitchen and pulled out a card. I looked at JJ who was as perplexed as I was and clearly knew nothing. Sam slurred incoherently and just passed the card to JJ who read "every sex act mentioned tonight must be performed over this weekend". Sam's 'I have never' made much more sense now. I was thinking back to what was said in the 'I have never' game and shuddered with equal parts fear and excitement. Sam said "and don't even think of cheating I have been recording everything on the cctv cameras". There were a lot (about 18 acts were mentioned) and the ones from this evening counted so we were part way there.

With JJ's older sister Lisa and her husband Bob arriving tomorrow we were going to have some explaining to do, and hopefully some extra help with our challenge. I really hoped her parents were still busy this weekend though.

Sam wandered inside and fell asleep naked with her hands in her crotch, while me and JJ gabbed a bottle of champagne, and headed to bed where we jumped straight into our favourite 69 position for some sustained pleasure thinking about what was coming next.

To be continued in part 2... if it is any good??

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14 Comments
jedt2016jedt20162 months ago

Can't wait for part 2....

AnonymousAnonymous3 months ago

Yes pretty fun in this part, but the things mentioned for next time jump the shark. No thanks! Yech.

AnonymousAnonymous3 months ago

started out interesting and ruined with the end.

so you are going to have his wife being fucked airtight and having sex with a stranger for money ? and husband being pegged ? no thanks.

AnonymousAnonymous4 months ago

Not bad for a start but it needs better proof reading. I look forward to having them complete more of the acts that were mentioned and including the rest of the family.

AnonymousAnonymous4 months ago

Simply put, yes for part 2....

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