Strip Trivial Pursuit Challenge

I had always flirted with Clare, she is good fun and desperately in need of a boyfriend. We had tried to match her to several of our single friends and her best friend my girlfriend Susan used to say she would have a much better chance if she lost a little weight. Clare was not really fat, she had a very big round bum and big breasts but quite a trim waist and had I not been with Susan I would certainly have been interested myself. She has short black hair, which I think if it were a little longer would make her look slimmer anyway.
Clare kind of feels relaxed with us and has spent many an evening with us on the sofa watching a movie or chatting whilst demolishing our fast depleting wine supply. Susan and Clare take turns to cook and we even all slept together in a hotel one night when a f****y room we had booked turned out to have only one double bed. Although I saw Clare in her skimpy knickers there was no threesome which I had secretly hoped for and Susan kept hold of me in bed so my hand could not inadvertently wander onto Clare’s curvy form which was so tempting being that close.
Susan and I have been a couple for four years and she is quite shy, I think mainly due to her tiny breasts. She is very pretty with long dark hair and frame so petite she has to buy c***dren’s clothes, in order to get anything to fit. We are very active sexually and she has gained much more confidence than she had, with my encouragement for her to show off a bit more. Susan has great legs and the best butt I have ever seen. I can get both her bum cheeks in one hand and she loves the fact I am obsessed with her arse.
My best mate Jerry lives in the Northeast and we don’t see him as much as I would like and Clare was getting quite excited when he was coming to visit. Although she was Susan’s best friend she has never met Jez but has heard all the stories and thinks we sound very similar. Sue and myself laughed about the possibility of a match, as Jez likes his women like stick insects it was highly unlikely. Susan frequently complained that Jez had been a bit too familiar with her as she put it, and I had to have a quiet word over a pint and tell him to keep his hands off my girlfriend’s bum, although I didn’t mind really.
I suppose it’s a North East thing but we spend lots of time in the pub when we see Jez, and although I thought Clare looked stunning Jez was doing all he could to pull the barmaid who had tried to short change me earlier.
Apart from sticking his pool cue up Sues short skirt and several smutty comments about parking his bike in Clare’s cleavage or bum crack we had a pleasant, funny inoffensive evening. Well that was until we started to argue on the walk back about why men in general were more intelligent than women were.
We laughed at ridiculous arguments trying to prove our points and then Clare had the brainwave of proving it by a trivial pursuit challenge boys against girls.
Just before the first throw of the dice Susan was goading us by saying how easy this was going to be, so I suggested if they were so confident we should play strip trivial pursuit. Susan immediately said no way but Clare was up for it as she was certain they would win. Susan reluctantly agreed and as we were working out that we had to get into six items of clothing each, I could tell Susan was really nervous as she does this lip licking habit when she is really under pressure.
So the girls started but we struck first with a history question and they lost a shoe each, which as part of my rules, we removed and they would have to in turn undress us if we lost. They quickly lost again on Science and Nature and Jez pulled Susan’s other shoe off as I slipped Clare out of her short boot to reveal her cute small feet.
We refilled the drinks and I could tell Susan was really on edge and she flushed as she had to loose her shirt and Jez peeled off Clare’s T-shirt. Clare proudly displayed her huge boobs in her skimpy bra and Susan looked very embarrassed in her thick padded bra still looking pretty flat against her chest.
We had still not lost a single item but Susan got an athletics question right and Clare one of the history ones and with in a few seconds we were only one item in front of the girls.
Then we got a geography question right, quite by chance more from our football knowledge but of course we would never tell the girls that. It was my turn to undress Clare and I un-clipped her bra when she stood up, she quickly fastened it again and said jeans first I think. I had quite a hard job getting Clare’s jeans off, as they were so tight but a great job all the same. I slipped my hands over her big dimply bum and over her strong muscly thighs. At last she stood in front of me, my eyes level with her knickers which could just not contain her abundance of jet black pubic hair, which f***ed its self out of all the seems of her tight pants. Susan shook her head as I sat there transfixed but was quickly snapped out of it by Jez who wanted to claim his turn.
amidst protests and warnings Jez unzipped the back of Susan’s skirt and slowly manoeuvred it past her bum, which looked naked in her tiny thong. Susan already had her hands over the see through front of her knickers and Jez grabbed her hips and thrust his face into her, licking and biting her bum, Clare and I laughed as she struggled free and stepped out of her small skirt and quickly sat back down. Susan was scarlet probably part with rage and part embarrassment.
We were looking good as the two questions we needed were now our best subjects and Susan knew I was good on sport.
Just as she started to protest and say this had gone far enough I rolled the dice and we landed on entertainment as Clare read the question Jez jumped up as he knew the answer saying to Clare it was time for us to see her big busters. Clare being a sport stood smiling whilst Jez blatantly groped her huge free tits. I was just pleased to still have my jeans still on or there would have been a wig wam situation.
Susan stood up accepting her fate and kissed me whilst I took off her bra, her nipples were the opposite of Clare’s they were tiny and very erect, she seemed to forget that her trimmed but hairy pussy was also on show through her see thu knickers. She was ready to quit the game but as she was already virtually naked she sat in again and seemed to relax even though Jez was staring at her.
We won the game next roll and I had the joy of slowly removing Clare’s knickers to reveal the hairiest pussy I have ever seen. Jez removed my girlfriends knickers with his teeth, which he insisted was with in the rules, and of course held on to her bum and pussy to steady himself whilst working.
This was the first time any man other than me had seen Susan completely naked, and although she was completely flat chested compared to Clare her embarrassment had disappeared and she was enjoying Jez drooling over her naked body and tiny tits.
The girls by now were totally relaxed about their nudity and it wasn’t long before Jez had manoeuvred his way between Clare’s thick thighs and I watched his circumcised cock rub briefly against her hairy brush before disappearing completely inside her. Susan giggled and nervously licked her lips as I easily pulled her on top of my aching erection, she slipped over it much easier than usual as Jez watched her being split and filled. Susan was so wet I easily pushed my middle finger completely up her tiny bum hole as we were all having sex openly on the floor. Jez and Clare kept changing positions as they fucked happily in front of us, I really think Jez was just getting himself into a better position to view Susan’s exposed pussy.
I was certainly enjoying watching Clare’s big naked arse impaling its self on Jez’s cock and her huge breasts swing from side to side.
Had some one risked asking to swap partners I think we may have all been up for it as Susan sucked my cock deliberately with her bum and open legs facing Jez, even she was horny beyond caring.
In the morning we had a great laugh and no one felt awkward, the girls even want a rematch and have promised to dress up properly, so who knows I may get my hands and cock into Clare yet, and Sue may give in to the lecherous Jez.
We have arranged to go to his next month, all three of us so I will keep you posted.
Alan
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Posted by award6
2 years ago    Views: 1,140
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2 years ago
Yes great story. I'd love to read what happens in the rematch if Susan will give in to her sexy side.
2 years ago
very sexy story, cant wait for the rematch
2 years ago
great story - hopefully part two to follow!