This is a story about crossdressing family sex involving all members of several families. If anything is offensive, don't read it and close this story. It is purely fictional and there is no relation to any real-life persons or families.
If you like the story/stories, email me at frackett@hotmail.com and I will try to answer every email. You've been warned; enjoy or close now! Fred
Jerry was just getting ready to head out when Carol drove in. He tried to act as nonchalant about the day as possible, the memories of him and Dan fucking like crazy still emblazoned in his mind.
Carol acted as blaise as possible about her first day at work; telling Jerry what a nice boss she had, he was married, strictly professional, wanted her to look nice for the clients, she'd have to buy more clothes but it was worth it, he gave her a $100 raise right off the bat for a clothing allowance, etc. Of course, Jerry thought that was just great, he'd have more to play in! She asked if he minded... he almost jumped to tell her how much he didn't mind! He'd even 'help her out' and go with her to shop... she liked that idea! When he walked out of the house he had a big fucking boner thinking of spending hours in ladies lingerie departments, openly looking at bras, panties, stockings, garterbelts, etc., picking them out! Whatever fit Carol fit him, so it was perfect!
Jerry's first client was already pre-set, all he had to do was write the policy and collect the payment. It was his second, and last appointment that interested him. He'd gotten a mailer back from him requesting disability insurance; he was a gym instructor and needed protection should he get hurt. Jerry had a policy that would fit right in with his Workman's Comp and Social Security, he thought it would be a nice sale! The guy's name was Hank and when Hank opened the door, Jerry almost whistled. Hank was in a pair of lycra skin-tight short shorts and a cut off tank top, and nothing else!
"Jerry, right? Sorry Jerry, was working out and the time got away from me! Hope you don't mind..." Hank smiled warmly.
"Oh no, don't mind at all!" Jerry smiled back at him. They chit-chatted for a half hour then got down to business, Jerry outlining a nice plan for him at an affordable price. When he got to the medical info, Hank told him of one problem he had - he'd had a hernia as a child and one testicle never descended, and was anxious that it might be a problem.
"No, according to underwriting there shouldn't be as long as it's still functional..." Jerry grinned.
"Well, you can inspect it if you like!" Hank grinned back.
"Oh really? Well, we don't normally give physicals... we're not licensed for it.. I could send you to a doctor.." Jerry lamented.
"Well, it wouldn't be a professional physical, just us two.. "Hank grinned at him, a twinkle in his eye. "Just like friends, you show me your's and I'll show you mine.."
"Well, that's a thought.." Jerry breathed heavily. His eyes were turning into lust-driven slits. "You could compare your's to mine, see how much it's affected the area.. I see you're anticipating such an inspection.." Jerry groaned, seeing Hank's cock stiff and throbbing in the tight lycra.
"Oh fuck yes, I sure am..." and stood up. Jerry motioned him to come close. "Now, we just have to have a gentleman's agreement that this is purely unofficial.. " as Jerry slid his palm up and down Hank's cock with one hand and felt his tight buns with the other. "I'll even admit to being a professional cocksucker, but I can revert to amateur status at any time.. so just think of me as a willing, cocksucking amateur, ok?" Jerry breathed heavily.
"Oh yes.. I"m a guaragteed cocksucking amateur also... and can do anything you want.. just ell me.. I love to be ordered around.." Hank groaned as he helped Jerry pull down his skin tight lycra shorts. "Hope you don't mind the extra finery..." as Jerry got to see the frilly little thong he wore under the short! "I have a thing for ladies undies.."
"Well now, so do I, as a matter of fact..." Jerry groaned, pulling the undies aside and slipped Hank's long, hard cock between his lips and going up and down it voraciously. "Damn, I didn't know I was so fucking hungry for cock!" Jerry giggled, sucking on his cock some more.
"Oh baby you do that so fucking nice... wanna put on lipstick?" Hank blurted, unable to stop himself from having a drag-fest night.
"Yess.. in fact..." Jerry grinned, yanking his pants and shirt off. He was wearing stockings, garterbelt and panties under his clothes.
"Ouuu you sexy stud! Lemme feel that cock in your panties!" Hank groaned, diving for it, sucking on it thru the panties, then pulling them aside sucking his hard, naked cock for him.
"You said lipstick?" Jerry cooed, guiding his head up and down.
"Oh yes, sweetie.. right here!" Hank moaned, pulling a tube from his pants pocket. He applied some, then Jerry did, both of them kissing, then slithering into a 69 on the floor, their hands groping each others' asses and balls...
"..... Hi, sis.. this is Carol, you busy tonight? I'm here alone, as usual, Jerry won't be home until 10pm or longer, he's got 2 appointments so ... I just thought.. if you're not too busy..." Carol said with a smile in her voice.
"Oh wow! Great! See you in 10 minutes!" Carol shuddered. Her sister said she'd love to cum over... she knew what that meant - her sister was as horny for her as she was for her sister! Ever since they were kids they'd explored all sexual avenues together and even today they loved to get together and whore it up,... She had to get ready! Carol flew into the bedroom, stripping naked, powdering and putting on perfume, a dab of lube up her cunt and ass, applied her makeup heavily like a true slut, then into bra, panties, stockings, garterbelt and a long flowing sheer negligee and high heels. Just then the doorbell rang. She ran to it, tossing the door open. There stood Cindy, her sister, a long overcoat on. She carefully guided her inside and offered to take her coat, her breath quickening. She gasped when she removed the coat - Cindy had on an outfit almost identical to her's. They'd worn these outfits for several years, but their impact on each other was still no less than spectacular!
"Oh honey... it's so good to see you.." Cindy smiled, drawing Carol into her arms, the two kissing passionately as they rubbbed their tits together in their bras. They both slid their fingers down each other and touched their breasts, bellies and asses, "Oouu yesss!" they both cooed!
"A drink?" Carol offered. Cindy nodded and they went into the kitchen. As Carol reached for a glass Cindy got behind her and slid her fingers up Carol's torso, massaging her tits and belly, then pushed her panties aside and slowly worked a finger into her cunt as Carol stirred her drink for her. "Oh fuck yesss you hot little slut!" Carol moaned, undulating to her sister's fingerfucking! "Lets go into the bedroom..." Carol moaned, leading Cindy by the hand, pulling her into the back bedroom.
"C'mere sis, I'm going to lick out your pussy and asshole and shove dildoes in you.." Carol groaned, slipping Cindy's negligee off her and guiding her to lay on the bed. Carol stood over her and dangled her big tits over her face to lick on, then slowly kissed down her belly to lick her pussy....
Jerry left Hank's over an hour early as he'd done all he'd had appointments for. When he pulled into the driveway he was surprised to see his sister-in-law's car there. And, he could see off the back fence that the bedroom light was on. Instead of going into the house, he thought he'd check it out.. he'd always wondered about his wife and her sister, ever since a New Year's Party when he unexpectedly walked into a back bedroom and they were kissing. And, it was more than a friendly 'Happy New Year' kiss. He carefully opened the gate and crept to the back. Ducking, he peeked up over the window sill where he could see under the blind - they always left one window open a crack for ventilation. 'Oh hot fuck!' he exclaimed to himself. There on the bed was his sexy wife in garterbelt and stockings, on her knees, her big tits swaying back and forth as her sister Cindy fucked her with a strapon dildo, her own big tits bouncing around like beachballs on her chest. Jerry always wondered what she looked like naked and it was a wonderful sight! Even though he'd just cummed down Hank's throat and Hank had filled his asshole with a big load of cum, then licked it all out, he could feel his cock rising again in his panties. Ouu yes.. in his panties and stockings and garters, just like his wife and sister-in-law had on... did he dare? Sure, why the fuck not?
He slipped back to the front door and slowly opened it, hitting the alarm button immediately so it wouldn't chime. He silently closed the door and stripped off his shoes, pants and shirt, rearranged his cock so it tented his panties and silently crept to the bedroom door. Carol was screaming, 'FUCK ME YOU CUNT BITCH - HARDER!' and Cindy was groaning as she thrust her fake cock in and out of her, the inside rubbing on her clit into orgasm after orgasm. Jerry silently pushed the door open, then crept towards them, both facing away from the door. He slid his hand out to rub on Cindy's rotating ass, then pulled it back and decided to rub his cock on her instead.
"Can anyone join in?" Jerry said softly, suddenly rubbing his panty-covered cock on Cindy's ass. She must have jumped 8 feet! Carol, who was sucking a dildo, suddenly spit it out and screamed.
"You two are just so lovely together, and I just want to add to your pleasure in my panties and stockings... please let me join you.." Jerry groaned, rubbing his cock on Cindy's ass again.
"It's fine with me if it's ok with Carol!" Cindy grinned.
"Oh fuck Jerry you're not pissed off?" Carol said with a tremor in her voice.
"OH hell no.. I've wanted us to do this for a long time! Let's swing and enjoy each other! I hope you like my panties and stockings and garterbelt... I just love wearing your things, honey.. I figured you wouldn't complain, seeings how you're fucking your sister... Cindy.. too bad Carl didn't cum with you.. I'd suck his cock again.. he and I've sucked each other in panties, bras and stockings several times... did you know that?" Jerry moaned as he buried his face in Cindy's asshole, tonguing her until she couldn't stand it.
"Oh fuck no.. but I'd love to see you two do it.. I'll call him up.. now... oh fuck your tongue is so fucking good.." Cindy groaned, going back to slamming her big fake cock into her sister. "Honey? Cum over to Carol's.. we're having a fuckfest and Jerry's here eating out my asshole and wants you to cum over in your panties, stockings, garterbelt and bra and he'll fuck your ass after he gets done fucking mine.. oh yes, he's dying to suck your big cock like he did before.. I forgive you.. You should see me fuck my sister with a strap on.. she's fucking enjoying it, totally!"
Carl could just stutter that he'd be right over.. fucking damn! He was home alone and had already dressed up while his wife was gone, so he just threw on pants and a shirt and headed out the door. When he arrived Jerry met him at the door, his cock out of his panties and obviously had been fucking Cindy's asshole.
"C'mon honey, let's show them what real fucking is!" Jerry smiled, pulled his outer clothes off him and led him into the bedroom by his cock sticking out of his panties. "The panty boys are here!" Jerry said gleefully, turning and kissing Carl on the lips, then slowly kissed down him and took his cock in his mouth.
"Well fucking damn... lookit that!" Carol laughed. "That so fucking turns me the fuck on.. ram me hard sis, I'm gonna cum like crazy!" Carol groaned.
"Yeah, I'm cumming right the fuck now!" Cindy shuddered, slamming her fake cock in and out of her sister's cunt, shuddering with each thrust as it ground against her clit....
"Daddy, whatcha doing out here?" Crystal asked, stopping her bike as she and Jr. rode up to the house.
"Oh, I wanted to fuck mommy but she's spotting and doesn't want to.. " he said wistfully. "And, I've got this big hardon you two gave me this afternoon and can't get rid of it... do you know anything we could do?" Dan grinned inside to himself. Lesson 101 on how to get your kids to fuck you!
"Yes, daddy.. we can go out to the playhouse.. that's where Jr. and I will go lots of time to get away from you and mommy when we want to fuck..." she grinned devishly.
"Oh really? Sure, show it to me.." Dan groaned. He'd figured they had a hideaway somewhere!
It was small and cramped but large enough for them to get naked. Dan sucked his breath in when he saw his daughter's supple, young, high breaste and smartly shaved bush. "My little girl has grown up.."
"So has your son..." Jr. groaned, pulling his panties down to expose his cock to his dad. "Remember how to suck cock, daddy? We watched you suck Jerry, remember!"
"Oh yesss, son..." Dan groaned, getting on his knees and taking his son's cock between his lips. He massaged his ass and felt his balls, then looked down and saw Crystal's mouth descend on his own cock, slurping and sucking on it. Oh fuck it felt soo good!
"C'mon daddy, let's fuck, ok?" Crystal cried. She got on all fours and pulled his cock to her, centering it on her cunt. With a couple good pushed Dan had impaled her, his cock sliding in and out of her young, hot cunt. He couldn't believe how great it felt! Then he spread his legs as he felt Jr's cock press against his asshole. Oh fuck, his son was fucking him while he was fucking his daughter!
Diane heard some noises from the back yard, ignoring them at first. But, they got loud enough she could hear some groaning. She crept outside and heard them in the playhouse. Who was in there? She almost crawled to it until she could peek in the little window. She saw her duaghter on all fours getting fucked by her husband who wes in panties and stockings and garterbelt who was getting buttfucked by their son, who's cock was as big as his dad's! Her kids were becoming hot little cumsluts like she was when she was young! it was about time! Diane felt her pussy - it was on fire! She pulled her panties down and started to fingerfuck herself.. it turned her on sooo much! Finally she couldn't stand it and had to crawl beck to the house so they wouldn't hear her. She ran for the bedroom and her dildo and fucked herself silly, groaning and cumming like crazy!
Dan felt his young, hard son's cock fuck his ass. It brought back memories of Bruce.. his boy lover he had in school. Bruce loved to cum over to his house after school as his mom was never there, always working. It started out innocent enough - they'd play games, hide and seek, and so on. But one afternoon Dan found a porno mag of his dad's.. it was of all men fucking and sucking any way possible. Fuck'n A horny mag! They'd stare at the pictures and check each other with furtive glances to see who was hard.. and they both were!
There was one section in the back of the mag called 'Frilly Fun' that interested them both. Guys wearing women's lingerie... it interested them alot. Dan asked Bruce, "Have you ever tried on anything?" and Bruce just smiled and nodded. Dan was sitting on a hassock and motioned Bruce to his side to look at the pics. "You'd look good in these ones.. " Dan pointed out. "Do these pics make you hard?"
"Oh yesss - very hard, how about you?" Bruce gasped in heated pleasure. "See him holding the other guy's cock? I'd love to be doing that!"
"So would I... especially in panties.. wanna put some on? We can get some out of my sister's drawers. Let's go look..." and they carefully walked into her bedroom and rummaged thru her drawer, coming out with garterdbelts, stockings, panties and bras. They were feeling the finery when Dan murmured, "C'mon, let's try it on.."
They went back to Dan's room and watched each other get undressed, and when both of them nonchalantly took their shorts down they stared at each other's hardons. Bruce let out a little moan as he watched Dan stroke his hard cock, then stroked his own in return. "Doesn't this make you fucking horny?" Bruce moaned.
Dan took a step forward and reached for Bruce's cock. "Go ahead, reach out and hold my cock like in that picture and I'll hold your's.." and Bruce did, gasping as he felt Dan's hot, hard cock in his hand.
"Oh fuck it feels just like I thought it would.. oh your cock is sooooo nice!" Bruce moaned as he stroked Dan's hardon and Dan stroked his hardon. "Careful, you'll make me cum..." he warned.
"No, let's not go too fast..." Dan groaned, letting go of Dan's cock, and Dan letting go of Bruce's. "Let's put on some undies, ok?" and reached for a pair of panties.
"No.. no panties yet.. put on your stockings and garters first.." Bruce instructed. "Once you get your garters and stockings on you can put on the panties, but not before.. if you do you'll trap them in the garterbelt and won't be able to get them off.. and I definitely want your panties off at some point while I suck your beautiful cock!" Bruce said knowingly.
"Yes, and I want your's too!" Dan answered. "How do you know that tho? Unless... you've put them on before?" Dan questioned as he rolled stockings up his legs, luxuriating in the feel of them.
"Mmmmmm.. yes I have..." Bruce smiled, wriggling as he snapped the garters in place. "Here, like this..." and bent down to help Dan snap his on. His breath was hot on Dan's throbbing hardon, only inches away.
"Oh fuck, ohhhh.. Bruce..." Dan almost pleaded, thrusting his hardon out with his hips, bruching Bruce's wanton lips.
"Yes.. a little right now.." Bruce groaned and bent forward an inch and slid Dan's cock in his mouth. Dan shuddered and leaned back, amazed at how good it felt!
"Oh Bruce.. yesss... oh fuck yess..!" Dan groaned.
"That's enough for now.. we have to put our panties on, remember?!" Bruce laughed, drawing his mouth off Dan's throbbing cock, sliding panties up his stocking'd legs and tucking Dan's cock in them. Then he kissed his panties all over, then stretched out as Dan put Bruce's panties on him and did the same.
"Oh you little whore slut!" Bruce giggled. "Don't you just love this?" Bruce giggled, pulling Dan to his feet, the two embracing, Bruce slowly kissing him, their legs entwining, their cocks in their panties rubbing on each other's.
"Yes.. oh yesss.. I just love it.. you hot little bitch!" Dan played along, kissing him back passionately. They slid to the floor into a 69 and pulled their panties aside with their teeth, slowly sucking on each other's cocks, then Bruce got Dan on all fours and pulled his panties down and carefully centered his cockhead on Dan's ass. Dan didn't know what to expect and at first it hurt, but then suddenly Dan rocked into him, telling him to increase his thrust, suddenly enjoying it!
"Fuck me honey..fuck me you sweet baby.. you hot whore, fuck my asshole!" Dan groaned. "Fuck me hard!" and Dan suddenly started shooting his cum everywhere totally involuntarily. Bruce grabbed his cock and got a few of the spurts and brought them to his lips, licking his cum, then shot his hot load up Dan's asshole. He pulled out and dropped to his knees, bending forward and sucked and licked every drop of his cum from Dan's asshole, tongue-fucking him rapidly.
"Oh fuck.. oh fuck.. fucking good.. oh that's so fucking wonderful!" Dan groaned. "How'd you learn this? It isn't something that cums naturally!" Dan queried.
"Promise you won't tell?" Bruce asked seriously.
"No, I won't tell a soul.." Dan promised.
"My dad... I caught him once dressed up.. he helped me dress up.. then we sucked and fucked.. we do it every chance we can now.. we both love it.. I'll get him and me and you together.. ok?" Bruce guaranteed.
"Yes.. oh yes.. oh yesss yesss yessss!" Dan moaned.
"Do you like it, Daddy?" Jr. asked, licking his cum from his dad's asshole.
"Oh yes Bruce.. oh fuck yesss... " he muttered.
"Bruce? I'm Jr., dad!"
"Oh fuck.. sorry.. thinking of something else..!" Dan came to his senses.. "It was wonderful, Jr.... just wonderful, you hot little daddy-fucker!" Dan laughed, back from his memories. Hurriedly, they got dressed and went into the house like nothing had happened, Diane asleep on the couch. Dan shook her.
"You feel better, honey?" he asked.
"Oh yes..." Diane smiled up at him, her cunt raw from the fucking she'd given it, knowing what happened......