Dinner With the Boss

Dinner With the Boss 3

By Jamie

The author wishes to remain anonymous and can't receive feedback

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This work is intended for ADULTS ONLY. It may contain depictions of sexual activity involving minors. If you are not of a legal age in your locality to view such material or if such material does not appeal to you, do not read further, and do not save this story.
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Dinner with the boss Part 3

One week later:

A week passed, and Friday morning arrived ad Tommy was busy getting ready for school making sure he had everything he needed both for school and the swim meet afterwards. He was in the 50m breaststroke and in the relay team today.

“I’ll be down at the pool by 530pm darling so in plenty of time to see the races. Good luck if I don’t get to speak to you.” His mum gave him a kiss as he opened the front door to leave.

“Bye Mum, love ya” he called out.

Linda smiled as she walked up stairs to check she had got everything that needed doing for this evening. Victoria was coming to the swim meet after work with her and then back home for dinner and staying overnight. She mused on the last time Tommy had been with Victoria and how he had been naked throughout the stay... I wonder she thought...

Sitting in her office, Victoria was having the same thoughts as she contemplated her forthcoming evening. It would be fun seeing all those fit young lads in their speedos and then returning home with Linda and Tommy... how to get him naked again, she did enjoy how he was embarrassed by it all. Perhaps she could suggest a photo shot of him in his speedos? “umm have to give it some thought during the day”, she smiled and got on with her work in hand.

The changing room

After a pretty boring school day, Tommy was in the changing room along with his team mates. The school swim team had 13 -16 year olds, 4 year groups, so he was in the second youngest group. The older boys ruled the roost but generally everyone got on. Soon the room contained 24 teenage boys all dressed the same... if you can call a pair of red speedos dressed that is. Coach walked in and gave a short talk and checked everyone was present and correct. They were swimming against two other schools and so in each individual race there would be 6 boys, 2 from each school. The relays would finish the swim meet and were by age group, except for the last race which was a medley with one boy from each year group. Coach would decide that team based on performances during the evening.

The swimming pool.

Outside the swimming pool stands were filling up mostly with family members coming along to support their boys. A lot of the girls from the school were there for the boy’s swim meet, perhaps because they liked seeing the boys in just their speedos! Sitting in the middle Linda and Victoria were chatting after having just arrived from the office. Linda was explaining what races Tommy would be in.

Suddenly a voice spoke over the PA to announce the start of the meet. Music followed and out walked the two other school teams, St Josephs and The Newtown Academy. Then with a fanfare the announcer asked everyone to cheer the boys from Hardcastle College. Victoria lent forward as the boys in their red speedos paraded out, oldest first, so she had to wait a little until she saw the near naked Tommy walking out, she smiled, he looked good and the taking in all the boys she pondered how revealing a pair of speedos was. They hardly hid anything, the bulges fully front and centre!

As he walked in Tommy was looking up at the stands to see if his mum had made it in time. He looked towards her usual spot and sure enough there she was, chatting to another lady. On closer examination it suddenly dawned on him that the other lady was indeed Victoria. He blushed involuntarily and shook his head in disbelief. The memories of their last meeting came flooding back to him – him naked in front of her and his mum! The scary thought then emerged - what if mum has invited her back to ours after? He tried to push that thought aside and concentrate on his first race which was number 4 on the list.

Race number 4 saw Tommy and 5 other 14 year olds step forward, all in their speedos. Tommy and his friend Simon in red, the boys from St Josephs in blue whilst Newtown had lurid yellow speedos which none of the boys from that school liked. They stepped onto the blocks and bent over finger touching the edge ready for the starting whistle, all was quiet for the Under 14s 50m breaststroke, 2 lengths of the pool. The whistle sounded and all six dived into the water swimming short way underwater to emerge with Tommy in second, neck and neck with Simon in 3^rd. The top 3 touched the end almost together and the sprint of the second length commenced in earnest. Tommy was really pushing himself determined to win, and soon was alongside the boy from Newtown. Into the last 10 metres and he drew ahead as the other boy was tiring and with a final push both his hands touched the end first closely followed by Simon who had also overtaken the over boy. A 1 -2 victory for Hardcastle. A quick shake of the hand with the other competitors a, hug for Simon and Tommy pulled himself out of the pool, the water running down his body glistening in the lights.

Victoria gave a big whoop of a cheer and he looked up and waved, blushing somewhat as Simon said,

“Well done Tom, good push at the end there. Who’s that next to your mum cheering you on?

Tommy paused, “It’s my mums boss, I met her last week when we went to dinner at hers, she said she might come along, didn’t realise she’d be embarrassingly loud!”

Simon laughed, “I think our parents enjoy annoying their kids, well that’s what my Dad says” the boys laughed and grabbed their towels.

Looking down from the stands, Linda and Victoria were taking in the two boys standing there chatting. They looked quite grown up and had well toned swimmer’s bodies. Linda was saying,

“That’s Simon with Tommy, they are best friends, Simon half lives round our house it seems. I often get home to find his bike strewn across the path, go in and all I can hear is music blaring from Tommy’s bedroom which suddenly gets turned down when they realise I’m home. And they always tell me it helps them work better. As if! He’s a nice lad and good influence on Tommy so I don’t mind really.”

The swim meet continued and Tommy and Simon relaxed on the side benches with their mates waiting for the relays. In their age group relay Tommy would swim breaststroke and Simon backstroke with Duncan and Paul doing the crawl. Up in the seats, the ladies were enjoying looked at the boys and even noticed how one younger boy from Newtown clearly had an erection as he stood on the block waiting for his race to start. He looked embarrassed as his erection was pushing his bright yellow speedos out. Fortunately, the race starter didn’t leave them standing on the blocks long, so he was able to dive in and when he emerged at the end of the race all his equipment was back to normal size!

The boys from Hardcastle Under 14s came second in their really race, but Tommy had swum his leg well again, so coach chose him for the final relay doing the breast stroke again. It was first time he had been chosen so Tommy felt good and found himself thinking how well he wanted to perform not just for his Mum but for Victoria as well. He shuddered and wondered how this woman had got inside his head like this.

The final race soon came around and Tommy walked forward with his 3 team mates to take their place in the lane 1 which was the closest to the stands. Linda noticed immediately that Tommy was in the race and excitedly told Linda this was his first time he had been chosen. Victoria smiled and looked down at Tommy giving him the thumbs up as he looked towards them. He smiled, without realising adjusted himself in his speedos and prepared for the race. The backstrokers started the race and breaststroke would be second with the two fast front crawl legs at the end.

The race was close, and Tommy dived into the pool in second place and when he had finished his 50m he and the boy from Newtown touched almost simultaneously. They got out and stood with their team mates cheering on the swimmers in the pool, the sound was deafening as the roars got louder as all the swimmers were within a stroke of each other. The final leg and school swim captain 16 year old Alex Harben powered into the lead, did a wonderfully smooth tumble turn and brought home the victory for Hardcastle by a whisker. A big cheer erupted from the home crowd as the school celebrated not only winning the final race but tournament as well by a few points. It had all rested on the final race, it had been that close.

Tommy was thrilled with his part in the race and got an encouraging well done from coach who was fun but strict too. He had been known to dish out the punishment as well the praise, but the boys thought he was great even though a few of them had at times felt his wrath, usually well deserved!

They victorious side walked into their changing room, the visitors having been given the girls changing room for the meet, so it was just the 24 happy boys in there enjoying their victory. The Head popped in to say well done, and they then hit the showers.

Tommy walked into the showers still wearing his speedos and suddenly found himself grabbed by Alex Harben the captain and 2 of the other 16 year olds.

“Well done Tom, good swim in the relay. Relay initiation time” he said in Tommy’s ear whilst holding him firmly from behind. One of the older boys reached over and pulled down his speedos, laughing and then plonked them on his head. “Now Tom all new relay team members have to do the star jumps until we say stop.” Alex slapped him on the arse and the older boys laughed as they stood under the showers, the naked Tommy in front of them, most of the other boys watching as well. Tommy had seen this happen before but had forgotten it, and now he realised he had to do it.

“Come on Tommy boy, get jumping.” He started doing star jumps much to the amusement of everyone and soon his willy was hardening and slapping against his tummy each time he did a star jump. Shortly after he was allowed to stop and stood there getting his breath back as the older boys laughed.

“Works every time” laughed Alex, as Tommy’s erection bobbed. He blushed but although embarrassed was glad to be part of the team. He sought refuge under the warm shower and Simon came and joined him, laughing

“Hey big boy! Remind me never to get picked for the relay team, Tom. I’d think I’d die if I had to do that!”

Simon looked down at Tommy’s still erect penis and added conspiratorially, “I didn’t realise you were such a grower Tom.”

Tommy re-joined, “well next time you are round mine, you will have to do a practice for when you get chosen.”

He laughed as Simon said, “No way”.

The boys finished up and soon were dressed back in their school uniform and headed outside, where they walked up to Linda and Victoria who were waiting in the foyer.

Linda gave Tommy a big hug, which made him somewhat embarrassed and Victoria said how impressed she was by his prowess.

“Are your parents here Simon?” He nodded and pointed over to his parents and his older sister, said cheerio, slapped Tommy on the back “way to go big boy, see you later” and ran off to join them.

Victoria thought it was rather a strange choice of words given that Tommy was definitely smaller than Simon. She tucked away the thought that crossed her mind for later.

They walked over to her car and soon were back home. As they entered the warm house, Tommy dropped his bag down and began to head for his room to get changed out of his school uniform.

“Not so fast young man” said Linda, “come here.” She pointed at the bag and said, “I assume you were not planning on leaving this here sunshine?”

“No mum,” he replied.

“Good! Now I want to get a picture of you to celebrate your win today and being chosen the combined relay team. No don’t look like that Tommy, you did really well, and I want a picture, so take your bag upstairs please, hang your towel up to dry and then change back into your speedos and come back down. “

He started to protest, but Linda stood firm, “Come on I’m not exactly asking you to swim the ocean am I, I just want a couple of pictures of my winning boy. Chop chop, up you go now.” She stressed the word NOW and knowing his mother he knew this was the final word, so grabbing the bag he trudged upstairs.

Victoria turned to Linda, “did you just come up with that idea Linda, if I didn’t know you better I’d think you were planning something.” Linda just smiled, and said quietly, “I did enjoy our visit to yours last week and how it all panned out. Tommy has been pretty good this last week, and been much more compliant, so I think a little more naked ‘therapy’ will do him and me some good.”

Victoria smiled, and thought she’d get a picture or two as well.

A few minutes later a near naked tommy emerged at the top of the stairs in just his red speedos. About half way down his mum told him to stop. She had the camera out and took a couple of pictures looking up at him. Victoria noticed there was only a slight bulge in the front. She took out her phone and captured a couple of pics herself.

Linda directed Tommy into the living room where there was a large fireplace with mantelpiece, a large mirror hanging over the top. She got Tommy to stand arm resting on the mantelpiece looking to one side so that she wouldn’t be in the picture in the mirror and then added, “perfect and smile for goodness sake Tommy please.”

He manged a nice smile and then before he could escape again, Victoria said,

“Your friend Simon, what did he mean by calling you big boy Tommy. He must be about 3 inches taller than you.”

Tommy blushed, and muttered, “oh nothing”

“Really?” Said Victoria arching an eyebrow at him. “it sounded very deliberate to me.”

Tommy looked at the ground, and said nothing, his mind racing to think of an explanation which wasn’t the truth.

Victoria pushed, “well we know that you are certainly a big boy under those Speedos don’t we Linda?”

His mother giggled, “well we did you see you in all your glory last weekend dear and it wasn’t small”.

By this time Tommy was open mouthed and shaking his head in disbelief.

Victoria, said, “I assume you’re bigger than Simon then? “

“I’ve never seen him hard, but he saw” said Tommy suddenly stopping mid-sentence realising at the same time that meant that Simon had seen him erect. A point not lost on the 2 women. He realised too late what he had said,

“well it’s not what you think...” he stammered

“well tell us then dear.”

He was simply left with no choice having backed himself into a corner, Tommy could have kicked himself for not having made some joke about Simon’s comment earlier, but now what could he say, he had just as near as dammit admitted that Simon had seen hard. Perhaps the truth was the best answer, as he didn’t want his mum thinking other things...

He began to explain about the initiation and how he had had to do star jumps in the showers

Linda laughed when he finished describing it, “well I think we should share in the victory celebration don’t you Victoria? I think our guest would like to see a repeat.” He shook his head,

His mum stepped forward and said, “Come on darling it’s not exactly anything we haven’t seen before is it? It will be a giggle.”

“A giggle for you may be, but it’s not funny Mum. Its embarrassing. “

“Oh, come now darling, don’t so precious and shy. You weren’t shy last weekend were you. Now stop being silly and lighten up. We are waiting...

In his head Tommy was torn in two. he was embarrassed and mortified but also quite turned on by the fact that Victoria was watching. He wasn’t best pleased about his Mum, but he did like Victoria, there was something about her that attracted him in a way he didn’t understand.

He reluctantly, anxiously but inwardly rather excitedly pulled down his speedos, his willy had hardened up a bit with all the talk and it wobbled as it was released from the tight-fitting trunks.

“GO Tommy” shouted Victoria.

He started doing star jumps just like he had done less an hour ago, but only this time rather than a few naked mates in the showers, it was his Mum and her boss watching him. It didn’t take long for him to become filly hard and erect and his penis slapped against his tummy with each movement. After a few minutes he stopped out of breath

His erect penis stood vertical waving about in the air before coming to a stop pointing sky wards. He was well endowed for a 14-year-old before and was already 5 inches long and still growing. There was a neat bush of jet back hair and the beginnings of a hair line rising up to his tummy button.

He looked good and fit with his swimmer’s body.

“Wow “said Victoria “thank you Tommy that was quite a display, all that movement certainly turned you on didn’t it.”

Tommy looked down at his willy and to his horror noted that the top was glistening with pre-cum, he hoped the ladies hadn’t seen it.

His Mum clapped her hands, “brilliant my son is well and truly a young man. And hung like his Dad it seems.” She turned to Victoria,

“Tommy’s dad and I didn’t last together long but the one big thing in his favour, pun intended, was that he was hung like a donkey and knew how to use it. Seems Tommy has inherited his father’s endowment.”

She turned towards the boy who had a quizzical look on his face having never heard this fact about his Dad before.

“Next time you visit dad, Tommy, go swimming and have a shower after, you’ll see how big he is. Now Victoria and I are parched, so before you go and get sorted can you go into the kitchen you’ll find a tray with 3 glasses on it and inside the fridge is a bottle of bubbly. You know how to open it so open and bring it in, you can a small glass tonight.”

Tommy almost ran out the room to escape and busied himself with the drinks. Thank fully as he was busy his willy gradually returned to normality.

In the adjoining living room, his mum put on music and so he didn’t hear the front door bell go.

His Mum answered the door to find Simon on the doorstep asking if Tommy was in because he had forgotten to give him a textbook he wanted, so he had cycled round when he found it in his school bag. Linda smiled and said come in, he’s just getting some drinks for us.

“This is Victoria, Simon, my boss and friend. She’s come to stay with us after watching your great swim meet today. You swam well, good to see 1-2 in your race.”

“Err thanks, “said Simon blushing a bit, as he was quite shy around adults, especially those he didn’t know.

It was at this point the oblivious Tommy walked in carrying the tray of bubbly wearing absolutely nothing at all....

(End of File)