The night club was dark and the music blasted out and Lee walked to the bar to get another beer when he spotted Diana standing the bar having a drink. Lee was 35 and, like many other men, had fancied Diana like mad since school days but being a good bit overweight had never been in her league. "How you doing?" asked Lee and they entered into a conversation that lasted for about half an hour or so when Diana decided that she wanted to leave. Lee said he'd walk her home as they lived nearby to each other. The couple walked for about 20 minutes when they got near to Lee's flat. "Would you like a nightcap before I take you home?" asked Lee and as it was a bit in the cold side Diana accepted. The nightcap extended to several bottles of lager and as they were both getting a little worse for wear Lee began to think that this was possibly his best chance ever to get inside the woman of his dreams. "How do you fancy a game of cards" asked Lee. "I would but I don't have any money left" replied Diana. "That's Ok" replied Lee "how about I'll stake £10 a deal and you stake an item of clothing or a forfeit of my choice?" Diana thought for a moment, she was a bit short of cash at the moment and she was a reasonable card player so why not. What she didn't know was that Lee was a bit of a card shark. Lee lost the first couple of hands on purpose and happily handed over £20 but then his "luck changed" resulting in Diana losing her shoes and then her blouse where he could feel his cock rising as he could see her soft breasts rising above her bra and a hint of the nipples beneath the material. Next Diana's skirt hit the floor as she lost the next hand and Lee admired her shapely bum. Lee really was on a roll and felt momentarily sorry for her as he won the next hand and Diana removed her bra to leave the top half of her body naked. Lee's eyes were transfixed on Diana's breasts and was only broken when she said "What's up Lee never seen a pair of tits before?" Lee became a little flustered as he'd not had much luck with women and certainly none as gorgeous as Diana. Needless to say Lee won the next hand and sat back to enjoy the view as Diana stood up and slowly pulled her white cotton knickers down her legs. Diana felt a little uncomfortable standing naked in front of someone she'd known for so long and Lee's eyes drank in the view of her dark bushy pubic area. "Well you've won then" said Diana "have you seen enough? she asked. Lee knew that if he didn't do something she'd get dressed and he stupidly blurted out "can I fuck you Diana, I've fancied you for ages?" Diana explained that she had a boyfriend and the answer was no but if Lee promised to never ever mention tonight to anyone then he could "feel her up for a while." Lee knew that this was the best offer he'd get so he moved towards Diana and took a breast in each hand and squeezed them repetitively whilst Diana stood with a hand on each hip looking at him feeling her body. Lee became braver and gently pushed Diana towards the table so that her bum rested against the edge and then so that she lay back on the table. Lee's hands reached under Diana's thighs and raised them so that her legs splayed open and after all this time he finally got to see Diana's vagina. Lee's hands moved between Diana's legs and he rubbed his index finger between her slit which became moist and warm and gradually allowed him to ease a finger inside her sex. Lee got down on his knees to get a closer look and felt compelled to pull Diana's fanny open so that he could see as far inside her as possible and imagine what it would be like to put his cock inside this beautiful pink hole. Lee wasn't a virgin but he'd never been this intimate with a woman before and like all men had always wondered what the insides of a cunt looked like and now he knew. "Is that you finished then?" asked Diana who was feeling a little embarrassed by having allowed Lee to look inside her. Lee didn't answer yes or no but motioned Diana to stand up and turn around. "I just want to look at you from behind cos you've got a fantastic arse." Diana stood up and turned around and Lee gently pushed her forward so that she was bending over the table and Lee gently pushed her legs open and stood back to admire the view of Diana's naked bum and her fanny lips between her legs. Lee's right hand moved onto Diana's buttock and roamed all her arse and felt her bum crack between her buttocks. Again Lee felt gradually braver and his hand moved to the top of Diana's bum crack and slowly moved his fingers down until they passed over her anus. Lee's excitement jolted a level at the thought of what he'd just fleetingly touched and as Diana didn't comment he moved his fingers back up her bum crack until they were touching Diana's bumhole again. Lee had certainly never been allowed to do this before by any of his previous women and gently he tried to push his index finger into Diana's arsehole. "Sorry you're going to have to stop that Lee that's for me to poo out of only and not for fingers or cocks!" said Diana. Lee stopped as requested and asked if he could wank over her arse to finish and Diana agreed. Lee's cock sprang out as he looked at Diana's arse and he wanked his cock with one hand whilst his other hand held her bum cheeks open so that he could see her very intimate poohole between them and imagined what it would be like if he'd been allowed to put a finger inside. It didn't take Lee long before his spunk shot out onto Diana's bum and the night ended but at least Lee had had a night to remember.