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NON CONSENT STORIES

Timmys Secret Is Discovered

Timmys Secret Is Discovered

by trueorfalse78
16 min read
4.26 (10600 views)
adultfiction

Timmy was everybody's friend, married at 19 years old to his childhood sweetheart he was much loved at home and a good friend to his work colleagues, overall a very nice guy.

You would have thought Timmy had the perfect middle class life, his wife Chloe was an attractive slim blonde, always on a diet and spending her days at the gym, and in her free time she would be obsessing about her look in front of the mirror.

Looking good was everything to Chloe.

Everything seemed ideal from the outside but for Timmy he was deeply frustrated by the lack of compassion from his wife who showed little to no loving in the bedroom.

After the children were born, so often things can change in a marriage and Chloe found many other ways to keep herself busy and was often exhausted by bedtime. Chloe was always there for Timmy in many other ways, taking care of their household chores and cooking some fabulous meals.

They had 2 children who had now flown the nest to University, so Timmy and Chloe now in their early forties had the house to themselves. With all of this time on Timmy's hands he began to ponder the way his marriage was going. He loved Chloe and was sure she had not taken another lover and so he had no thoughts about cheating on her either. Anyway Timmy had wed his first ever girlfriend and had no idea how he would go about finding another girlfriend in this modern age.

Timmy did have a secret though, a very special one that he kept from Chloe and from everybody else. In order to keep his sexual tension under control, when his wife was at the gym he would go to their bedroom, and he would select a pair of her silky panties from the linen bin. He would put the gusset of her panties to his nose and inhale, he loved the smell of her female scent and would then jerk himself off into the gusset of her panties, covering the gusset in buckets of cum. He would then dry them the best he could and place them back into the washing basket before she came home.

Of course Chloe knew all along after finding crusty deposits in her underwear what was going on, so she decided to play along with Timmy and would deliberately leave a couple of used panties in the wash bin.

On this Wednesday Timmy was going to Chicago for the annual Pottery convention, he had only been a couple of times, usually it would just be his boss who would go. This time Timmy with his boss Luke and Luke's secretary Emma would all be staying at a plush hotel for two nights and then return to home on Friday afternoon.

Although he would have his own room Timmy hated these conferences, so much so that he usually sat at the back of the conference hall in case he came under the spotlight, and in the evening he would retire to bed early after the evening dinner whilst the rest of the delegates would drink and party all night until the early hours.

On Wednesday morning Timmy met his two colleagues at the airport gate and boarded the plane. Timmy sat at the window seat, Emma in the middle and their boss Luke sat in the aisle seat.

Timmy had always fancied Emma, she was five years his senior but the way she dressed was immaculate, always wearing black skirts and pantyhose and with her long black hair she looked very attractive and womanly.

Timmy felt very invigorated sitting next to such a delicate and sexy woman, he sensed the faint odor of perfume, and the occasional touch of her arm on his own. She made little conversation preferring to read a woman's magazine. Then it was time for our meal and the air stewardess came round and served us all. Much like Emma she was dressed in a knee length black skirt with black hosiery.

Having sex with an Air Stewardess is a fantasy of Timmy's, like most of us to be honest and he enjoyed the attention she gave him as she served his food and drink.

Once the meal was cleared away and the table folded and pushed back up to the seat back, Timmy couldn't take his eyes of Emma's perfect legs then Emma looked down and could see the profile of a hard-on at Timmy's lap.

Seeing this Emma flicked off her shiny high heels shoes complaining about a blister and how men didn't have wear such hideous garments, and brought her leg up and rested her hosed foot on the edge of the seat. Timmy noticed her skirt was ruffled up more than usual and he could see her white silky panties showing through the darker support top of her pantyhose. Timmy felt some movement in his groin again, his cock was stiffening and so he turned to face the window imagining how good it would have felt to be wearing those pantyhose and her silk panties.

Next he felt a hand brush his wood, and Emma said "I see you are enjoying the flight Timmy."

Sexual tension was ended when the seat belt sign came up and the plane came in to land.

On landing the three colleagues passed through the airport and Luke called a cab to take them to the hotel. Hotel check in went fine, Emma and Timmy were on the fifth floor and boss Luke on the fourth floor. The three of them made their way to the elevator pulling along their travel bags.

Luke entered first taking his time, next Emma hurried in through the elevator door and just as Timmy pulled his small wheeled case into the elevator the door closed trapping and squeezing his case between the doors. Luke pulled at the doors and Timmy yanked his bag but the door was having none of it, there was no budging, not even one inch, then Emma calmly pushed the button with the outward arrows opening the doors and releasing his bag which had been badly damaged, spilling the contents of Timmy's case onto the elevator floor. Everybody looked down in shock as laying there on the elevator floor was a white pair of silky panties and a pair of tan pantyhose. Luke bent down first, collected up the spilt garments and immediately looked up at Timmy's red face.

" Are these yours Timmy, what's going on here?" Luke said as he waved the lingerie in front of Timmy.

Emma seeing the embarrassment in Timmy's face quickly grabbed the items and said "They are mine Luke, my bag was over weight and Timmy was looking after these for me."

Emma then gave Timmy a cheeky smile and stuffed the panties and hose into her coat pocket.

"Well that's a relief," said Luke with a puzzled look on his face and requested that they all meet in the bar at 7.30pm to decide on a plan for dinner.

As the elevator arrived at the 4th floor Luke departed leaving Emma and Timmy alone.

"Lets go to your room Timmy and you can tell me what was that all about," said Emma who grabbed Timmy's hand and consoled him by saying "Don't worry, Luke suspected nothing."

On entering Timmy's room Emma looked into Timmy's bag to replace the garments and see what else he had hidden away.

"Oh these are lovely" said Emma as she held up a pair of shear black stockings and a suspender belt, "what good taste you have," she commented.

"I just like to sleep in them in secret," said Timmy.

Emma, all excitedly then said "I will come to your room after dinner and bring some make up and you can see how you look as a girl, now have a shave down below before dinner and we can have some girly time together later on."

"There's no need Emma," but secretly Timmy was excited and couldn't wait until night time, "Well OK," said Timmy, "And if that's what you want to do, after all you saved my job today so I owe you a big favor".

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Dinner went fine but Timmy still felt embarrassed and in the moments their boss went to the rest room Emma would hold and squeeze Timmy's hand comforting him.

Later that night and after several drink the three of them retired to their own rooms.

About 20 minutes later there was a knock on Timmy's door.

"Who is it?" Timmy whispered.

"Its Emma, please let me in," and in she came, dressed in her dressing gown and carrying her make up bag. She guided Timmy to the desk with a mirror and started to make him over, taking great care to apply red lippy and blushed his cheeks.

Timmy was astonished how feminine he looked, he was so grateful to Emma that he gave her a hug.

"Now try on your lingerie Timmy and we can share some girly time together."

Timmy removed his clothes, pulled up his silk panties and sat on the edge of the bed to pull up his tan pantyhose. Next Timmy opened his case and pulled out a pink baby doll nightie, something he had purchased especially for this trip. This totally completed the look he wanted and who he secretly wished to be. He wandered over to the mirror and looked at this stunning lady, he felt so proud and excited.

"Come to bed," said Emma "we will watch a girlie movie together."

Timmy was in heaven, feeling the sensations that he had been seeking all along, feeling his cock growing inside his silky panties in the company of a sexy woman was just what he needed. Emma had chosen the film Pretty Woman, a story about a prostitute in LA, and how she met a wealthy business man. The two of them were relaxed, sipping white wine and giggling when all of a sudden they heard Bang! Bang! Bang!

"Its Luke, open the door!"

Luke had been back to the bar, failed to pull a woman, then he had gone to Emma's room to find nobody in. Then he remembered the elevator incident and went all out to retrieve something from the night.

Emma quickly collected her things and hid in the wardrobe.

Bang! Bang! Bang! and the door nearly came of its hinges again.

Timmy put on a jumper and pulled up his trousers over his pantyhose as quickly as possible and then opened the door.

In rushed Luke, pushing Timmy onto the bed "I know those pantyhose were yours, Emma only wears black and yours were tan, what do you say you tranny?"

Then Luke looked down at Timmy's feet, sure enough he could see the tan nylons "take those clothes off and sit on the edge of the bed in your pantyhose you slut."

Luke turned off the TV, dimmed the lights and made himself at home, he took a beer from the mini bar, looked down at Timmy in his nylons. Well he thought if I can't have that prude Emma then this is 2nd best.

Luke drank some beer as Timmy waited, his heart pounding, his body dressed in lingerie and a baby doll nightie, he sat on the edge of the bed scared of his boss Luke and what may happen next.

Luke stood in front of Timmy. He unbuckled his belt and pulled his trousers down to his knees before discarding them.

Next he pulled down his briefs and a soft floppy cock of about 5 inches slapped Timmy in the face.

"Open your mouth and take it bitch," and Luke put one hand behind Timmy's neck.

Without a route of escape Timmy having been caught cross dressing by his boss decided to accept his fate and leant forward and licked the head of the beast, and while Timmy opened his lips Luke pushed forward and all 5 inches entered filling his mouth. Timmy swirled his tongue exciting Luke whose cock had now grown to 8.5 inches, 5 inches inside and 3.5 inches more to go. Luke held the back of Timmy's head still, and slowly thrust forward. The raging cock head popped through the muscles of Timmy's throat, Timmy couldn't breath, then he realized Luke wasn't withdrawing so he breathed through his nose and Luke pushed further down Timmy's throat making him choke. All of a sudden Luke withdrew in one go, Timmy took some deep breaths, coughed and then composed himself.

All this time Emma was watching quietly from the wardrobe, too scared to make a noise she stayed very still.

"On the bed tranny, on your front slut," Luke said and Timmy laid onto his front.

Luke now positioned himself with a leg either side of Timmy legs and sat just below his ass taking in the magnificent site of Timmy in a pink baby doll nightie, tan pantyhose and white panties there right before him.

Luke reached over and took a photo of Timmy laying there in nylons and a baby doll.

"Now Timmy you will experience what its like to be a real woman."

Timmy feeling this was out of control pleaded "No Luke, No! I was doing you no harm, leave me alone!"

"No Timmy, you have brought our company into disrepute with your perverted behavior and now I am going to punish you. It's either this or you are fired."

With that Luke yanked down Timmy's panties and pantyhose to below his ass, he spanked both ass cheeks making them pink and then reached over to the bed side table for a tube of KY jelly he had placed there earlier. He smeared the cold gel along Timmy's ass crack, then suddenly and with no warning pushed in his finger and circled the pinky around the anal ring causing Timmy to wince.

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Next he smeared more gel onto his cock and lined up his uncut 8.5 inches with the entry point, easing forward slowly, pressurizing and invading the outer ring then as Timmy succumbed to the force and his sphincter dilated open just enough to let the cock slowly move forward stretching Timmy, who had now lost his breath due to the sudden shock of the stretching and the burning feeling in his ass.

Luckily for Timmy, Luke stopped half way, giving his ass time to acclimatize to the invading cock before Luke pushed hard to the end, and then some more. When Timmy could feel Luke's balls against his ass he knew he had taken all of this huge piece of meat and strangely felt proud of himself.

As Luke slowly pushed in and out he asked Timmy "So what's it like losing your virginity, you dirty slut?"

"All is good sir" said a frightened Timmy.

The fucking proceeded and as Timmy's hole began to accommodate the 8.5 inches the pain began to subside, and then he started to enjoy a feeling he had never felt before.

Timmy was being driven to an anal orgasm, with no touch to his own cock, he had risen to an impressive 6.5 inches and as Luke pushed back and forth ever harder Timmy felt his own cock throb, his own ass contracted and a thick rope of cum wet the sheet below. Timmy's ass was grabbing hold of Luke's cock, squeezing it tightly as he came, feeling this super intense orgasm envelope his body.

Luke paused to enjoy the moment he had created, then began again thrusting again with long slow strokes, causing Timmy to cum again, draining the last drops of cum onto the sheet below before releasing his own sperm into Timmy's ass.

The coolness and creaminess of Luke's cum soothed Timmy's sore ass and then Luke collapsed on top of him.

After a few minutes Luke sat up and pulled Timmy's panties back up to his waist keeping his sperm inside Timmy's underwear.

Luke got up and knelt in front of Timmy, he then pushed his still hard cock to Timmy's face, "clean me up," and Timmy did, tasting the aromas on Luke's cock now stained with Luke's cum and his own anal scent.

"That's a good boy, there's more of this to come when we get back home you know."

Luke then got dressed and left the room without further comment.

Timmy lay down exhausted and sated, not knowing what to make of the evening.

Just then Emma opened the wardrobe door "has he gone?"

"Yes, he's gone."

"You poor thing, did he hurt you?"

"Yes he did!"

Emma climbed on the bed and spooned up to Timmy, she could feel the dampness of the cum seeping from the back of his pantyhose and onto her stomach. She reached over and slid her hand down the front of Timmy's panties and cupped his balls and cock.

Timmy could feel her stockinged legs touching his pantyhose, the shear pleasure of the nylon on nylon was fabulous for him. This is what he dreamed about before.

" Timmy, be honest did you enjoy it?"

"I guess so, I had an amazing orgasm like never before."

"Emma, have you ever had anal sex?" Timmy asked.

"Oh yes, I once had a boyfriend who took me every way, I grew to like it too. He wasn't as big as Luke to be honest, Luke's cock is truly amazing."

Emma stroked Timmy's cock until he started to jerk and throb and cum inside his panties.

"Thank you Emma, your so sweet for caring about me."

"Timmy, your so nice, please never change, just be a nice Timmy."

If you like we can watch him fuck you again as I filmed it all on my camera?"

"Oh no, not tonight Emma, can you delete it for me please?"

"We'll see hun, you get some beauty sleep and we can discuss tomorrow."

The two of them fell asleep together and woke up in the morning in time to get ready for the 1st day of the conference.

Timmy wondered what was in store for him tonight?

The End of Chapter One.

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