DISCLAIMER: All characters are fictional, no relation to anyone living or dead, all are 18 or older. If you do not like sexually oriented material, LEAVE NOW.
Jerry was a 'bigwig' in the company. He'd worked hard, getting promotions until he reached the Executive group in over 30 years of advancement. He deserved it. He'd made many sacrifices for it, giving up weekends and vacations, traveling all the time, but it was worth it for the perks and benefits. None more so than the ones he afforded himself, however....
Jerry (Gerald P.) was impressive at 6' 4", lean and well built, no pot belly in his 50's. Looked great in his expensive suits, stood out in a crowd, big smile, down-to-earth, likeable kind of guy. Married with one grown son, a wife who didn't have to work, who busied herself with the Garden Club and golfing, tennis and playing bridge so she didn't mind him gone all the time making fantasic amounts of money!
His son, Gerald II, also known as Little Jerry, or Jerry Jr., still lived at home (their house had 28 rooms and 9 bathrooms - there would be days, even weeks, they wouln't cross paths, other than to hear his MG gun out of the driveway). He had his own set of friends who he'd invite over, but they would party out in the guest house, playing music as loud as they wanted, nobody could hear anyways.
Jerry would tour the company's plants. He was in charge of Production Management and was always looking on how to increase production efficiency; he had many very smart men and women working under him, but was always willing to talk with the trade and file, asking for their opinions on different matters. One such person was a fairly new worker named Matt, in his late 20's, who he'd briefly met on his last visit a few months ago. But, this time, Matt made it a point to shake his hand and smile. Then, when Jerry was walking by and Matt could say something to him privately, he whispered something in his ear....
"Sir... your garterbelt snaps are bulging...." is all he said, then let go of his hand and walked away quickly.
Jerry was mortified! No one ever even hinted that they could see anything, and he checked in the mirror to be sure. But.... how did Matt even suspect?
You see, Jerry was a closet gurlyboi, something he discovered in himself when very young, and loved getting 'dressed all under' in sexy, gurly lingerie under his fine suits! He just loved dressing in the morning after a hot, tingling bath in the hotel room, aching to put on makeup and lipstick right then, but held off until returning to his room after dinner.
His mother loved to put on her gaudy brassiere, black or red garterbelt, seamed stockings, and frilly panties and parade around their small apartment long before having to finish dressing from the time he could remember. The men she'd bring home would readily undress her, only sending him to his room once they were both naked and finished playing, now ready to fuck. She would often dress some men in her lingerie, they seemed to enjoy it and their dripping, throbbing hard cocks proved it!
As a teen during the summers while she worked, he'd sneak into her bedroom and try on all her things. It made him soooo hard! When he moved out, some of the first things he bought was underthings that fit him, scouring distant rummage sales where others didn't recognize him.
And ever since, he had a predilection for gurly underthings. Sometimes his desires got too much for him and he would invite another gurlyboi he'd met over for some fun.... sucking, fucking, pissing and playing in their 'things'. It didn't happen often, but when it did, it was fireworks!
So when Matt made reference to his garters, it petrified him, but also gave him a huge faming hardon too! It meant that he maybe had a new gurly friend!
That afternoon, before he left the plant, Jerry made sure to shake Matt's hand and palm a folded business card into his hand. On it was his room number and room phone number with simply, 'call me'. It was too late to fly out that evening anyways, and as soon as he go back to the hotel was a message from Matt.... Jerry called him back and invited him to dinner... in his room....
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Jerry Jr. and his best friend Clark had two females over to Jr's house. They were playing a card game called 'Swap'. It basically involved the players to swap clothes. Privately, Jr. and Clark had previously explored the many facets of male/male sex, including dressing, makeup, wigs, etc. So, with the girls, this should be lots of fun!
With each hand, there were 5 cads, and you had to follow poker rules. Whoever won a hand had to swap clothes with another, then once swapped once, to strip off.
Clark won a hand and asked to swap his t-shirt with Brandy for her bra. Brandy eloquently removed her bra and hooked it to Clark's back, then Clark turning and stuffing it with rubber breast molds. Brandy sexily slid his shirt on, shaking her naked tits inside it, teasingly.
Then Candy won a hand and asked for Jr's shorts, while she put on a strapon to fill them with. Jr. got to put on her lacy, frilly bikini panties, his hard cock bulging out the side of them! Of course, that got them all hot and Clark got on his knees and took Jr's cock in his mouth, sucking on it and Candy got behind Clark and worked her big strapon up Clark's ass. Brandy got all put out, wanting to finish the game, then Jr. made out with her, feeling her naked tits under the t-shirt, twisting her nipples. Brandy just LOVED having her nipples payed attention to and Jr. dipped his fingers into her hot cunt, getting her to cum, while Jr. came in Clark's mouth and Clark came in Candy's hand who was giving him a handjob while the strapon was rubbing her clitty to orgasm after orgasm! Clark took off the red, lacy bra and put it on Jr, who just loved it! That's when Jr's dad walked in, at that very moment....
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Jerry changed into a red lacy bra, red lacy garterbelt and sheer black stockings, high heels, slut red lipstick and long earrings just in time to take a pose on the couch when Matt gently knocked on the door. "Cummm in..." Jerry dripped.
"Oh my fucking..... oh fuck me silly!" Matt stammered, his cock immediately bulging in his pants!
"You guessed right about my garters bulging... thought you'd be interested seeing the complete package.... c'mere, kiss me.... lemme massage that wonderful lump!" Jerry giggled. "I didn't bother with my wig... do you mind?" he foamed, making out again as he pulled off Matt's clothes, wonderfully surprised to find similar gurly clothes on him too!
"Never in my wildest dreams.... oh darling!" Matt moaned, pushing his tongue down Jerry's throat, pulling out Jerry's big cock and sinking to his knees, taking his cock in his cocksucking mouth, lovingly sucking on it. "Oouuu you've got the lovliest cock, honey!" and bent to it again, sucking him longer and harder.
"Ouuu Ouuuu..... slow down, baby! I'm a once-a-night cummer now, not like I used to be...." Jerry giggled. "And yes, I do want to cum up your hot fucking asshole, sweetheart! Would you like that, baby?"
"Ouuuu fuck yessss... and i wanna cum in your mouth and your asshole, too!" Matt giggled.
"Ohhhh the wonder of youth!" Jerry moaned, bending over and taking Matt's hard cock in his asshole. "Cum in me baby, then I'll fuck you and suck you, too!" and the embarked on a wonderful evening of total bliss!
The next morning, Jerry awoke to seeing Matt scurrying around, gathering his clothes, rushing off...
"Gotta get to work.... um, boss...." he grinned.
"C'mere, give me a hot kiss good bye....." Jerry moaned, holding out his arms, the loose bra covered in dried cum hanging off his arms, where Matt shot load after load of hot cum all over him after Jerry got him to cum the third time while sucking on his balls... he was so glad to finally be able to share his gurlyboi fetish with someone else, esp. someone 20 years his junior who also loved being a hot, slutty gurlyboi too!
When he boarded his plane for home, he still had a hardon in his panties!
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Ann, Jerry's wife, didn't believe a fucking thing her husband told her about 'strictly business' and 'being too tired' when he got home. Who the living fuck was he kidding? She would climb the walls with lust until he'd get home, then he was too fucking tired to satisfy her? It didn't take many nights of that bullshit until she went out and got fucking relief from both men and women, getting licked, sucked and repeatedly fucked to satisfy her wanton desires! He always talked about her Garden Club work, showing off her lovely plants..... she earned those fucking plants eating out the older horny 60's and 70's women of The Garden Club... the bush gardens..... hot, orgasmning free-flowing, dripping wet cunts of the Garden Club.....
That particular day, Jerry decided he'd stay over instead of getting a late flight home, so she put some toys in a bag and went to see her girlfriend Gloria for the night.... about her same age, in her 50's, with a cunt annd asshole just flowing.....
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Jerry arrived home, no one to be found. He hollered out for his wife or his staff, no one there!
He faintly heard loud music from the guest house, so he drove over there to see what Little Jerry was doing, and not bothering to knock, he just walked in...
"OH FUCK!" Jr. groaned.
"OH SHIT!" Clark grunted.
"EEEEEEEE!" both girls screamed!
"D-dad... it's not what you think...." Jr. babbled, trying to get the bra and breast molds off him and got terribly tangled up, his cock hanging out of the panties.
"We... we.... we were just playing a game, called 'Swap'..., exchanginng clothes...." Clark stuttered, all of them putting on their original clothes.
"Wow, it sounds like fun to me! I love playing games! Erotic gurlyboi games.... let's all play it... but the first and only rule, I get to suck both your cocks, honey's!" and got down on his knees and took his son's cock in his loving mouth, sucking it voraciously!
"Ouuuu fuck yesss daddy... suck my gurlyboi cock for me, darling!" and Clark took Jerry's cock in his sweet mouth while Brandy and Candy ate out the two boy's assholes and dually fingerfucked Jerry's asshole.........
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Ann couldn't tear herself away from Gloria and decided to spend the afternoon with her too.... lucky for Jerry, Clark, Jr., Brandy and Candy, all sucking, fucking and cornholing each other in the guest house!