Thomas was lounging in his office chair, looking out of the window at the postman, he walked past, Thomas gave a sigh, no mail, things were moving slowly, when he heard his mother ascend the stairs. She was dressed in a lightweight beige suit, chestnut coloured stocking and high heels.
'I'm going shopping, for a pair of "whore boots".'
Thomas looked at her, 'you mean a pair of elegant shoes with a strap going around the ankle?'
'Exactly, "whore boots".'
'Your skirt is,' he paused as he checked her out, 'above the knee, flared, not exactly the most appropriate for sitting in a low chair while a salesman helps you on and off with shoes.'
'Exactly,' she repeated, 'ideal flashing outfit.' She held her skirt out to show the flare. Thomas moved forward in his chair and placed his hand on the back of her knee and slowly ran it up her leg, he felt the thickening as he reached the stocking top, then her bare flesh, she shivered.
'So, is there anything you want from me, money, a lift to the mall, what?'
'I've got my own money thank you, anyway, Stephanie's arranging a lift with Charlie but there is one thing, something I've never done before.'
'Oh,' Thomas was getting uneasy, his mother could be a bit of a wild card at times.
'Yes, I want to wear a dildo,' they're all up here.'
Thomas stood up and went to a cupboard, 'some are unused.'
'Yes, I know, plenty to choose from,' she handled a black one, it was soft and swollen at the top, 'this seems perfect, I doubt if that will fall out, do you?'
'No chance, you could trampoline and not lose that.'
She handed it to her son, 'I need someone to fit it, someone I trust to do it right.'
Thomas immediately stood up and removed his erect penis, 'this is a pleasant surprise,' and so saying turned her round so she was facing his empty desk, she leant forward on her arms, Thomas lifted her skirt, she was naked underneath. 'I hope you're not going shopping dressed like this?'
She indicated to the chair where she'd left her handbag, 'no, of course not, this was just to make it easier for you.'
Thomas probed between her labia, gently, yet he quickly felt her getting moist, 'the dildo might prevent me leaking cum, well I hope so.' As she completed the word "so", Thomas pushed his penis inside.
'Hmm, you can take your time if you want, I'm waiting for Stephanie, she's never on time.'
'I wouldn't allow you to go out dressed like this on your own, you know that.'
Thomas looked over his mother's bent body, 'uh, uh here's Stephanie, looks like Charlie's dropping her off.
'Do you want to stop?'
'Is the front door unlocked?'
'Yes, I left it open for her.'
Just then a loud, cheery voice called, 'Hi, where are you?'
Selene responded, 'up here, in the office.'
Thomas pulled out, 'I'll finish off when you get back.'
'Don't be silly,' Selene urged, 'It's Stephanie, she won't mind.'
Sure enough, 'I thought we were going shopping, have I got the day wrong?' Stephanie asked, all eyes on them both.
'No, I'm performing a magic trick,' he pulled out, Stephanie looked on, 'now you see it, now you don't,' and pushed it quickly back in.
'Thomas, it's magic but there's no trick to it, what are you really doing?'
'I'm going out wearing a dildo, Thomas is preparing me for the insertion.'
'Oh, I'm jealous, why didn't you tell me, I could have brought mine.'
'No problem, look in the box, they're some still in their wrappers, choose one of those.'
Thomas had stopped his "in-and-out" movements, instead he waited patiently for them to decide what to do.
'Thomas, I'm moist and I'm horny but not enough to take this one,' she said unwrapping a slightly oversized dildo, could you help fit it for me?' She had a big smile.
'Well, I'm kind of busy right now,' he said pointing to his penis which he had slid halfway out of his mother.'
'I'll tell you what, put my dildo in, I can get used to it and you can deal with Stephanie.' Saying this she pushed back on Thomas then forward raising herself from off the desk, his penis emerged, still fully erect.
'That's most kind Selene, how do you want me, Thomas?'
'I'll just fit this dildo and provided it goes in okay you can just take Selene's place.'
And so saying, he pulled Selene's labia apart with his thumb and fingers and inserted the selected soft black dildo. It went in surprisingly easy. Selene stood up, jumped up and down once or twice and pronounced that she was satisfied.
'Okay Stephanie, your turn,' without saying a word she took Selene's place over the desk and assumed the position.
Thomas had the pleasure of lifting her skirt and lowering her underwear, standing behind her, he placed the end of his penis against the top of her labia which were wide open, 'good position Stephanie,' and pushed, 'that's gone in no problem,' he told her.
'Yes, I know, feels good.'
'You know I'm going to have to come in you.'
'Of course, I expect nothing else.'
Thomas didn't mess about with thrusting and then stopping, he was too near his climax, the room was filled with the slapping of his thighs against hers and his groans as he orgasmed. He paused to get his breath back then pulled out, Stephanie looked over her shoulder and handed him the dildo, once again he went to work with his thumb and fingers, and it went just as easily as Selene's.
Thomas went to the bathroom and cleaned himself and returned to his office. The ladies were still there. 'Hang on a minute,' he asked, 'Isn't Charlie supposed to drive you two into town?'
They looked at each other slightly bemused when Thomas's cell phone gave a "ping", he read the message, 'problem solved, those books I ordered are in, I'll drive you in and pick them up at the same time.'
'We're not going to be quick; we'll be going to a few shops.'
'I'll be browsing round a couple of bookshops, before I finish off at Waterstones, tell me where to meet.'
'How about we phone when we're at Fleetwood's Shoe Emporium, then we can finish off at our favourite shop, "Heels", it's expensive but they're not a chain, and Freddy, the owner gives personal service, very personal,' the two ladies giggled at some private joke though Thomas could guess what they were alluding to.
The town centre was busy, and Thomas had no choice but to park in the overpriced underground parking lot, he argued that if you were coming into town to spend money, parking should be free. He wandered from bookshop to bookshop until he found himself at Waterstones, he perused the books they had until he decided to meet up with the ladies, he picked up his order and made for "Heels", hoping that they were ready to go back home.
He arrived at the shop and could see them at the far end, being fussed over by the owner, shoes strewn all around. He sat opposite them, Freddy looked over his shoulder, 'I'll be with you in just a moment.'