Simon And Sam's Second Weekend Pt. 01

Story Info
Sam buys Simon a full prom dress and undies.
1.1k words
4.29
9.7k
4

Part 1 of the 4 part series

Updated 06/10/2023
Created 07/13/2020
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A week had passed and the two mothers where again working combined shifts at the hospital, because of covid they were sleeping in a converted dormitory so Sam knew he had a whole week end with Simon alone. His mother was only too grateful that Sam volunteered to look after the boy, and also she'd noticed some changes in him lately, he was showering more and his room was cleaner and he washed up and laundered his own clothes. When she asked Simon about this he simply said it was Sam's idea so she nodded and approved of their friendship, and was glad the older man took a interest in the boy.

Man and boy had had their tea and washed up and we're relaxing watching TV, it was a pleasant July evening and the windows were open.

'I've bought you something Simon, it's upstairs on my bed.'

Simon looked at him wondering but quickly went upstairs and into the room. There on the bed carefully laid out was a blue 50's style full dress and attached petticoat plus underwear. With a sharp intake of breath he picked up the garments and held them to his cheek. The dress appeared to be satin and rustled when Simon held it to his cheek. Best of all a small bra with silicone falsies inside and a pair of satin panties.

Sam went to foot of the stairs and shouted up 'Shower first!' which startled Simon but he undressed quickly and dived into the shower, he spent a whole 12 minutes washing every where, hair, bottom and penis all got thoroughly washed and rinsed. Back in the bedroom he toweled off and stared at the garments, his heart was beating quicker and his hands where shaking but he was certain this was meant to be. He pulled up the panties tucking his small package inside and put the bra on all the while looking at himself in the full length mirror, next the dress and petticoat, he struggled with the zip but finally managed it.. He combed out his long hair and smoothed the clothes down and was startled to see how girl like he was, only 5' 3" and of slender build and although he was 19 he looked younger, indeed he looked better than most of the girls in his small friendship group.

'Hello Susan, you look lovely' and she nearly jumped out of her skin as she hadn't heard him come up, turning they flew into each other arms and embraced and kissed, Sam forcing his tongue into her mouth till she relaxed and played back and forth with him. He reached round and up under her dress and down the knickers till he found the little balloon knot of her anus and circled it with his index finger.

'Good girl, now across my lap please' and as though in a daze she did, he took the little tube and pulled down the panties to squirt a good measure up her anus and smeared some around the outer area. 'Now lie down' and she did and gazed into his eyes as she felt his hardness, quickly he rose took off his shorts and underpants and tee shirt and lay back down.

'Are you sure you want this Susan?'

'Yes, I've been thinking about it all week and I want to be her again, and I want to take care of you so you stay with me and Mum.'

He smiled at that, 'Well stay next door you mean, I wasn't about to move!' and they both laughed as his hand worked it's way under her dress and found the wet patch she'd made. On her back with her legs drawn up and apart he moved over between her legs and slowly drew the panties down but left them around one ankle. There is was, the small penis with long foreskin and leaking pre cum, he couldn't stop himself and dived down to take it into his mouth and sucked and licked as it grew.

'I'll take care of you later' and she nodded as he crawled up the bed and let his weight sink on her. He'd showered earlier but she devoured the musky scent of him as she was pushed down into the bed. She felt him bumping around her hole. 'Push out Susan, let me in!' and she did as his glands slipped into her anus and she flinched at the pain so he rested there. 'Good girl, good girl! You're doing so well!' Slowly she accommodated around him and the pain lessened.

'You can go deeper now' and she kissed him and used her heels to draw him further in, finally at the bottom his glands found her prostrate and rubbed over it. Resting there for a minute he began the slow but urgent trusting which he needed. Fully open now and reacting to the rubbing of her prostate she leaked more pre cum and clung to him as his tempo built up. 'Oh my god, fuck me, Daddy fuck me!' she hissed in his ear. All he could do was grunt and trust even harder as the dress rustled, bed creaked and the headboard tapped the wall.

Finally with a great bellow of 'Take my fucking cum you whore!' he shot his first load of semen into her rectum and collapsed sweating onto her as he fought to get his breath back. They lay there for 20 minutes listening to their heart beats returning to near normal. Then she pushed him urgently down the bed where he took her small hardness into his mouth and began a rhythmic sucking while gently squeezing her scrotum.

'Oh! Oh! Oh!' was all she managed as she flung her hands over her face and trust upwards into his wet warm mouth. His hands found her bottom and a index finger eased into her and her trusting became even wilder.

Finally shouting 'Fuck! Mummy! Cunt! Fuck!' she clutched his head and ejaculated into his mouth, one, two, three long spurts and he fought to swallow them but some escaped him and dribbled off his chin. Gasping she pushed him off and they clung to each other as she fought to get her breathing under control. They lay there entwined while the sun went down and the children played outside.

Eventually he rose and washed his face and hands and putting his clothes back on sat on the bed, she was curled up in a ball and he gently stroked her hair.

'I'm going to have a drink, you come down when you're ready' and he left her and went down stairs, he pottered around and poured a pint of beer and turned the TV back on. Upstairs he could hear her moving around and correctly guessed she was looking at his wife's clothes. 'What a wonderful weekend this will be' he thought to himself and smiled.


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3 Comments
AnonymousAnonymousover 3 years ago

NOT my thing.

ShadowRosieShadowRosiealmost 4 years ago

We are needing some plot and character building to happen. Are there three male characters? In the first paragraph we find Sam, Simon, and older man. Who is "older man"? It doesn't make sense.

You also have some horrible spelling errors. Please find someone to edit your story. Not to change the story but to fix the spelling errors and English grammar errors.

AnonymousAnonymousalmost 4 years ago
Confusing

Confusing and poorly written.

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