It all began after a normal drunken night out in a university town in England, Jess and Tom had been good friends for years, they had met in halls at university and now in their second year lived in different houses but regularly went out drinking together. More than once they had stayed at each other's houses, usually sharing a bed in a completely friendly way.
Jess was a pretty girl, she had had numerous boyfriends during her time at university, but at that time she was single. She was 5'6" with short blonde hair and blue eyes. She was always exercising and was proud of her slim body, but even more proud of her 34D boobs!
Tom was a rugby player, but not the usual laddish type. He was quite shy with strangers but had a very good relationship with Jess. He had an athletic build, broad shouldered and toned all over.
This particular night they had been out until about 3am with a group of friends and Jess had invited Tom in after he walked her home, time dragged on as they sat around chatting and eventually Tom ended up staying the night as he had several times before. They cuddled down in Jess's double bed, Tom in some borrowed shorts and a T-Shirt and Jess in her PJs and fell asleep for the night.
Tom didn't sleep well, he had been single for about 6 months and other than a one night stand a few weeks back had had no action in all of that time. For the first time in their friendship he began to struggle to keep Jess out of his mind especially spooned up as they were. As the morning came he was dozing and had a vivid dream of the two of them playing truth or dare, a game he had played as a kid but never since. But he awoke with a start to find Jess propped up laughing at him.
"What?" he asked rubbing his eyes sleepily,
"Nothing!" she replied "it's just you were smiling and muttering in your sleep and you looked cute, what were you dreaming about"
"Oh ha-ha!" Tom laughed nervously "it was nothing honestly!"
"No tell me!" Jess insisted "or else..." and she reached across as if to tickle him (a frequent punishment between the two of them)
"You don't want to know..."Tom said dodging away
"Ooo was it dirty?? Tell me!!!" Jess replied, sitting up now
"You really want to know??" he could tell when she got in this mood she never backed down
"Yehhhhhh!" she smiled and bounced a little
"Ok fine... well I was dreaming... that we... well we were playing truth or dare... ok...sorry it's nothing!"
Jess giggled, looked thoughtful, and then smiled "hmm wellllll you seemed to be enjoying the dream... so let's play!!"
"Really??" Tom look amazed at her
"Yeh" she said, "it could be fun!" and she smiled her winning smile.
They lay back down facing in towards each other and Jess still smiling started straight away asking Tom if he wanted truth or dare. For the first few games both chose truth, Tom learnt that Jess had last had sex 3 weeks ago with her ex, that her favourite position was to be on top, and that her boobs were 34Ds!! Jess asked him about his favourite position (doggy style), had him describe a fantasy (sex on a beach and in the sea) and wanted to know how often he masturbated (usually most days).
On the next round Tom decided to bite the bullet and took a dare, giggling Jess thought for a few seconds and dared him to act out a sex position with her. Nervously Tom agreed and carefully hiding his growing erection had her come up on her hands and knees while he pretended to come from behind doggy style. As they lay back down again Jess opted for a dare too. Tom with hardly any hesitation dared her to remove one item of clothing. Jess stuck her tongue out and reaching under the duvet slipped off her PJ shorts.
After that they had a couple more nervous rounds of truths. Jess had to admit that she too masturbated most days and that she did own a pink "rabbit" vibrator. Whilst Tom described the wildest place he had had sex (behind a small hill in a local park one summers evening) and then embarrassingly for him tell her how big his cock was hard. At 7.5" he wasn't worried about it but he had thought Jess would stick to more simple questions.
Jess was having a hard time controlling her excitement, she knew Tom was an attractive guy but she had always just considered him as a friend. Now though she could hardly control her mind as it pushed forward idea after idea for truths and dares. When Tom chose dare next though, she knew exactly what she wanted and dared him to take off one item of clothing too. Tom looked resigned and slipped off his t-shirt to revealing inch by inch his rugby players physique. Jess could feel the dampness spreading between her legs and wondering how far this was going to go asked for a dare back.
Tom laughed, "Well if you can check me out I should be able to too" he said "I dare you to take another item off!"
Jess looked at him, pretending to be annoyed and then had a sudden brain wave, " fine!" she said, and reaching behind her back unhooked her bra, she slid the straps of both arms and pulled it out triumphantly, "taadaaaa!" she flourished and lay back down giggling.
Tom looked un-impressed but promptly picked a dare again, he was hoping that she would pick dare too and he could get her top off. Jess though had a sudden mental blank; her brain which had been swimming with the greatest ideas for dares was suddenly empty other than daring him to take off his shorts which she didn't think she was quite ready for as it would only lead to her having to strip too.
Finally she settled on a bit of a cop out and dared him to hell her how turned on he was by the game. But she was happy as his face turned a bright shade of red and he was forced to admit that he was fairly turned on!!
A few truths followed as both gamely tried to ignore what was probably going to happen next, Tom was made to describe his favourite types of porn, which clearly embarrassed him all the more, and then admit that he had only had sex with 3 girls in his life. Jess though had possibly an even more embarrassing time of it, having to admit that she always swallowed after a blowjob because actually she kind of liked the taste and then describe the drunken threesome she had once had with two guys on Tom's rugby team (which she definitely regretted). It was this last one and the fear of more truths like it that made her pick dare next.
There was a moments silence as they both looked at each other then Tom suddenly smiled "I'm not going to go with the obvious..." he said pausing again "I think I have a more embarrassing one for you!!"
"Go on..." she replied, "I don't think I'm going to like this!"
He laughed again "oh I think you will like it, it will just embarrass you... I dare you to masturbate under the duvet for 30 seconds!!!"
Jess's jaw would have hit the bed if it could; she could barely even think, shy Tom suggesting something like that... "Errrrm I dunno" she finally came out with,
"CHICKEN!!" teased Tom reaching across as if to tickle her. She tried to fight it a little longer but really Jess was incredibly excited by the idea and was dying to touch herself to relieve a little of her tension, finally she gave up and slowly and obviously slid a hand under the covers and seductively down her tummy, she slipped her fingers gently under the elastic of her French knickers and over her outer lips immediately feeling how soaking wet she was. Staring straight into Tom's eyes and sticking her tongue out again she slipped her finger deeper and gently began to masturbate
"There!" she said, hardly believing that she was doing it. All too quickly Tom called time and reluctantly Jess stopped.
Tom couldn't believe that she had gone through with it, he had thought that would be the end of the game and in a rush of excitement he chose dare too. Jess looked thoughtful and then decided "I'm short of ideas..." she said "off with the shorts mate!!"
Tom laughed and reached down to slide them off, staying well under the duvet even though he still had is boxers on. Jess took a truth next and had to admit that she too was really turned on by this game.
Tom though decided to stick with dares and Jess had to think for a bit before rolling over onto her sTomach, "I want a back rub!" she said, and pushed her face into the pillow "I promise no peeking!" With some difficulty Tom climbed on top of her and began to rub her shoulders. He knew he was good at massages but today he just couldn't focus, it didn't help that he was staying very upright to keep his rock hard cock away from Jess's back and he was quite relieved when she called time and he rolled off catching a glimpse of her gorgeous bum clad in purple French knickers before she pulled the covers back up.
Jess was torn, she had loved her back rub and had been so excited when a couple of time she felt his erection press into her back, but she knew what he would want next if he chose dare... but she also wasn't ready to stop playing. In an instant she decided "dare!" she said scarcely believing she had done so.
Tom looked delighted "well I only have one left so you should too!" he teased "loose the top missy!" Jess rolled her eyes and carefully adjusting the duvet reached under to pull up the hem of her top, with a little wriggling she got it off without showing him anything and threw it at him. Tom smiled and immediately asked for another dare.
