Chapter 5

"Hi, is that Miss Mason? It's Jeff Williams, you said I could ring you."

The voice that replied was soft and gentle and reassuring. "Hello Jeff, yes, this is Diana Mason. I am so pleased you called. Did you want to come and see me?"

Jeff's ordeal at the interview in front of 41 year old Miss Mason and a teenage assistant had been traumatic, and his total failures during training at home had been depressing, but he was hoping that things might improve now he had actually plucked up the courage to phone her.

Miss Mason, Diana, was delighted he had called. She remembered every moment of that first interview. Jeff had been so deliciously shy as he obeyed her instruction to undress, that Diana had felt her heart pounding. When he finally sat down with his hands covering his penis, she didn't know whether to laugh or cry. What she really wanted to do was take the terrified boy in her arms and kiss him!

The teenage assistant beside Diana firmly instructed Jeff to put his hands down by his sides, and he reluctantly did so, exposing a quite remarkable and very upstanding cock. He was biting his lip and looking away from the two women inquisitors, obviously desperately embarrassed.

When Diana just sat there admiring the sight of him, the young girl started the interview. She explained what Last Man Standing was all about, and stated firmly that the males in the cage would be naked all the time until they were evicted. Jeff nodded nervously. She went on with more of the rules, about what the girls could and couldn't do, and about what she and Miss Mason and Jeff would be doing shortly as part of this interview. Diana interrupted the girl just once. "Open your legs wide, please, Jeff darling."

The girl then started asking the questions that were in the mandatory part of the interview notes, quickly finding that Jeff had really very little experience with girls but was eager to try for the competition. He admitted that mostly it had been Mandy who had pressured the other members of the family into volunteering. Jeff was keen to do his best but not sure whether he would be any good.

Diana was thinking, 'This darling kid will capture the hearts of the television audience. We have to make sure he isn't eliminated too quickly.'

It took the girl a long time to extract all the answers she wanted, and by the end of the inquisition Jeff was almost in tears, and Diana was in love. His answers had been delightful, and Diana knew that he would be a hit on U-tube when he was reluctantly answering these same questions inside the cage.

Yes, he had seen his sisters naked, but only by spying on them in the bathroom or when they didn't shut their bedroom doors properly. Yes he had seen his mom in her undies quite often when her dressing gown came open as she was preparing breakfast and things. No he had never seen any other girls or women naked. He had kissed one girl at a party and liked it but the girl hadn't let him do it again.

Yes he masturbated. Several times a week. Diana interrupted, "Just show us how you do that, darling." Jeff tentatively put his hand on his cock, but it was so obvious he would spunk if he moved his hand that Diana told him, "Yes, that's fine, put your hand down by your side again." She gestured to the girl to continue Jeff's torment.

Yes he did sometimes go into his sisters' rooms, and his mother's room, and yes he knew which drawer they kept their undies in, and, after repeatedly trying to avoid answering, he confessed that yes he went through their undies drawers. Yes he sometimes put their undies on, first taking worn ones from the laundry basket but also more recently he had been putting Mandy's fresh panties on in the girl's bedroom and watching himself in her mirror! Diana butted in again, "So is Mandy your favourite?"

Jeff nodded shyly. "Please, don't tell her." Diana promised, but had her fingers crossed. She was longing to watch Jeff squirm when this came out on live television.

The girl now explained that they needed to test his ability to withstand temptation, to make sure that he would not cum too quickly. She asked Diana if she wanted to go first. Diana was reluctant, she didn't want to humiliate the darling boy, but it had to be done. She stood up and removed her blouse. Jeff stared at her expensive lacy push-up bra, nothing like what his mom wore! Diana came around in front of her desk and bent forward to grasp the hem of her skirt, giving Jeff a fabulous view of her cleavage.

Then she slid her skirt slowly and sexily up to her waist, exposing long stocking-sheathed legs, then suspender straps over bare thigh, and then silky panties. And sadly that was it, for Jeff. His groan must have been heard in the waiting room!

Assuming he had failed dismally, he started to cry and Diana took him in her arms and was about to press herself against him when the girl warned her to be careful of the semen on his tummy. So Diana knelt down and licked it all off! The girl watched incredulously. Diana held the boy tight for a few moments then told him to get dressed. She asked the girl to go and get her a cup of coffee, and the girl left the room. While she was out, Diana gave the boy her business card, and told him to phone her.

Which he was now doing. Diana was delighted, she really hadn't expected him to dare to call. "How are things going, darling?"

"Um well not so well. I mean, there's nothing wrong or anything it's just that I'm letting the family down all the time. Like I did in front of you."

She could tell that Jeff was nearly crying as he admitted this. "Oh baby don't get upset, most of the other boys your age that are trying to get into the competition are having the same problem. Look, would you like to come and see me and discuss it? See what we can do to help you?"

Jeff felt a wave of relief! "Oh please Miss Mason please yes can I?"

She asked when he could get away, and he said he had just got home from school, his mom was at home but she wouldn't mind if he went out for a bit. Diana said she would send a taxi to collect him. "Tell your mom someone from the network wants to see you for some training."

When he arrived at her house in the suburbs, she was wearing a house coat over sexy undies, and the first thing she did was tell him to undress.