Summer of Servitude

[wickedpen]

Tracy enjoyed the transformation of Jason from firm "No way!" to "what do I get?" She smiled but not too much.

"You get to remain a closeted cross dresser" she said holding up the phone with the pic of him in the bra and panties.

"Go on" she said nodding towards the closet as her legs moved opening for him then closing unconsciously. "I think the yellow sun dress will look nice, especially with the black thong and bra underneath." she said licking her lips.

 

[georgerb]

Jason was chilled and heated at the same time. Never had he thought about wearing a dress...that was just gross. And seeing Tracy lick her lips caused him to think what that tongue would feel like on his balls even with the panties on. Now that his cock had felt the inside of Ann's moist pussy and her cum, he wanted more.

Opening the closet door he saw the dress she directed him to put on. With his smaller but athletic stature and Tracy's larger one that was almost Amazon like he should be able to fit into it. Pulling the dress out, each movement caused more excitement where the waistband rode against his cock. Slipping the dress over his head and putting his arms into the short sleeves. Feeling foolish as hell, but wildly excited as the soft fabric draped him and added sensation as it fell over the tip of his hard-on.

Turning towards Tracy on the bed, still idly opening and closing her legs, he caught a glimpse of himself in the dresser mirror. Holy shit. And with that surprised look on his face as the camera flash went off several times.

"Do I get to fuck you now bitch?"

 

[wickedpen]

"Oh no honey I need to make you up!" Tracy said excitedly bouncing up to her feet.

"Sit sit" she said excitedly. "Jalynn you must let me make you pretty or nobody will want to have sex with you"

She pulled the chair from the make up table back and stood awaiting him to sit. Seeing his hesitation she licked her lips and said "I only let lips with lots of red lipstick suck on my big nipples" her voice trailing off as her hand cupped her right breast and rolled the thick hard nipple.

 

[georgerb]

He hesitated a bit too much and Tracy stepped forward and grabbed him by his balls. Directing him to the chair and forcing him to sit. Sitting made the waist band of the black panties push deep into his hard cock but all he could see were those large nipples.

Almost as big as his Moms’.

It wasn’t as if he had done anything wrong...just snitch some panties.

“What’s your favorite shade of lipstick for sucking on titties, Jalynn?”

Her smirk was broad as she toyed with her pussy.

Ann looked shocked watching the screen while her Mom just chuckled.

“Leave it to your sister to invoke Slave 101. Should be an enjoyable summer for sure...before you know it, we’ll have him caged correctly.”

 

[wickedpen]

Grabbing the "whorish red" from her counter she moved around and straddled jalynn's thighs. Tracy pinched his chin and began wiping the red lipstick into his lips. She was not doing it nicely either.

"You need a lot so it leaves a nice circle" she explained as she ached to move her hips forward and feel his cock against her clit but resisted. After covering his lips she looked at him. "Eye liner" she said turning and grabbing the tube and pulling the applicator from the black liquid.

"This works best if you look away" she said as she used her fingers to hold his eyes lids open. His eyes had a difficult time peeling away from her tits. but did and she dabbed the balck onto his lashes and lips.

She leaned back and looked at her cousin. He looked more clownish than girlish but that was not really the point.

Tracy stood and stepped over his thighs as he seemed in shock.

"OK bitch, you are ready." she hissed as she moved to the bed and laid on the side. "I want you to stand next to the bed with your hands behind your back . bend at the waist and make a perfect circle around my nipple." she said without looking at him.

 

[georgerb]

Jason, or now as Tracy's Jalynn, felt whorish as hell, foolish, and excited all at the same time. Shoving the thoughts of deciding how to get out of this situation to the back of his mind as he watched his cousin stand up and he got a clear shot of her pussy.

He stood as told and put his hands behind his back and was again straining to keep from cumming as the dress material rubbed against the head of his cock. He didn't even glance at the mirror to see how he looked...

Bending over as told, he lowered his head and formed on "O" with his lips and encircled Tracy's nipple closest to him. His lips met with such a tender warmth that belied the situation of being used by his cousin. Like an eager baby, he sucked in on her nipple relishing the texture.

 

[wickedpen]

"Suck it" Tracy hissed as her clown painted cousin leaned over as an obedient bitch. As he locked on like a hungry baby Tracy groaned happily. "Make a nice circle, don't mess it up" she cautioned. "How does it taste bitch? Like cousin Tracy's nipple? Lick it now" she instructed as she watched him. His eyes were closed and was enjoying this a bit too much.

"OK Stop. Stand!" she commanded. He hesitated dragging his tongue over her stiff nipple. She pushed his head back bring a "pop" from the break in suction as he stumbled back.

"I said STOP!" she screamed angrily. "I think you are enjoying this a bit too much Jalynn. Mother!" she cried into the air like she would materialize. Jason't face was pale and scared as Tracy spun up and got in his face like she wanted to fight.

"You aren't gonna follow my instructions. Then you are going to meet instructions you will!" she hissed as close to his face as she could come. Like a marine drill Sargent.

Aunt Jean opened the door and stepped in closing it behind her.

 

[georgerb]

He barely heard Tracy's direction as he was more concerned about getting to savor her tit...another first for him. To hell with a perfect circle he thought.

Before he could even dare to try her other one, Tracy shoved him up and back, stronger than he thought was possible. Fearful of what was happening or was about to happen, he stood there like a clown in a yellow sundress, with no place to hide or run to.

"Tracy, I..I just did what you said!"

She was in his face big time and he could sense her anger. His cock shrank as he heard Aunt Jean come in and close the door. The lace fabric of the panties like little fingers tickling his cock, as his balls shrank at Aunt Jean's voice....

 

[wickedpen]

"Jesus Christ Jason! What the fuck kind of fag are you?" Aunt Jean yelled angrily. "Tracy you know better than treating a man like this." she said as Tracy left the room. Aunt Jean came to him and ripped the dress off him and then the bra and panties painfully as she then pulled him by his ear across the hall itnto he bathroom.

"Get int he shower and clean that off" she directed him. he did as she said washing his face the best he could .

"I thought you were a man Jason? Not some trans freak? What will your mother say? Your father? when I tell them. You are going to have to somehow make this up." she went on handing hiim a towel when he was done but snatching it from hsi hands before he was dry.

"Get back in there" she hissed as she dropped the towel and followed him back into the room. She closed the door and then looked at him. She lifted the nightgown she was wearing off and stood naked in front of him.

"You want to prove you are a man? I know I look like your mother. I know that turns you on. Make me feel you are a man." she said as her nipples stood hard but small and her mound was unshaven. She did not look back for forty but not Ann or Tracy.

"You want to call me mom boy?" she said glaring at him standing naked and wet in front of her.

 

[georgerb]

Jason was completely shamed being stripped in front of his Aunt for some reason. Despite basically so in front of his cousins, there was another air to this exposure. He did his best tp get the make up off..he hated that waxy/chaulky taste of the lipstick.

Getting back to Tracy's room, naked and wet, Aunt Jean seemed to inspect him and then stripped. His mouth hung open as he saw her hairy pussy... the porn videos led him to believe all were shaved. His cock started to harden as it looked similar to his Mom's that he had caught glimpses of in the past.

He closed the distance between them and grasped those small nippled breasts, worried what would be deemed wrong over anything he did. He secretly wished he still had panties on as he always did when watching his Mom. With his thumbs running over her nipples he lowered himself to his knees so her bush was right in front of his face. Damn...how fucking sexy....

 

[wickedpen]

Aunt Jean paused for a moment as Jason knelt in front of her. Oh did she want him to go into her forest but she resisted.

"Fucking pussy" she hissed and slapped his head. She then walked back towards her bedroom. "When you are ready to be a man and treat me like a woman, you let me know" she said before pulling the bedroom door shut.

 

[georgerb]

His head snapped from her slap just as his nose neared that bush. "What..what did I do wrong?'

But the door slammed shut as he looked at her ass briefly. He was confused and still horny, and had no clue what to do about it. Seems he was always doing something wrong. Laying back down on the bed with his cock pointing upwards, he killed the room light. Just over 48 hours here and things were a mess.

In the dark, he went to Tracy's drawers and found another pair of panties to put on. He needed to clear his head with some sleep and hopefully an answer would come. Just as he did in those silk panties before drifting off.

 

[wickedpen]

In the morning the three women were in the ktichen when Jason came down. Things were different. They were all wearing pastel sundresses that were low cut. Ann in blue, Tracy yellow and Jean in green. Their hair was done and makeup too. Jean was wearing an apron and had bacon and eggs and pancakes all cooking. On the table was a pitcher of fresh orange juice and four place settings.

When Jason came in the two girls stood up and they all three said "Good morning" with big smiles and cheerful tones.

Aunt Jean quickly wiped her hands on her apron as she stepped to Jason and said "sleep well dear? Have a seat. We have a wonderful breakfast for you." She pulled out the chair at the table for him. Ann and Tracy beamed like girls in love.

"A young man like you needs to keep up hsi strength" Aunt Jean said letting her hand slid up his arm and feel his bicep. "Oh girls feel this." she said excitedly smiling at Jason. The girls jumped up and had their hands on his arms squeezing and rubbing.

"Do you work out?" Ann asked excitedly.

"You must lift a lot!" Tracy said letting her hands linger as she leaned over and gave him a view down her dress. She was bra less.

"The girls must be all over you" Ann said leaning over not to be out done by her older sister.

"Girls!" Aunt Jean hissed shooing them back to their seats. "Let the man have some peace." she said as she came and reached around him brushing her unsecured breasts against his shoulder as she set a steaming plate of delicious breakfast in front of him. She stood back up over his shoulder and folded her hands.

They three of them watched him smiling.

 

[georgerb]

Okay, something was askew or he had woken up in an alternative world Jason thought. Not wanting to be a trigger for anything, he smiled back at his extended family and took the seat offered.

Being graced with a healthy view of Tracy's and Ann's breasts and then feeling his AUnt's being rubbed against him from behind as she set the plate of food in front of him.

"Thank-you, it looks great! You shouldn't have gone to all this fuss, ladies."

As much as all three looked edible in those dresses, he tried to concentrate on the pancakes, but got that hidden feeling he was bing toyed with by three cats all out for the chase and capture of a victim. After all, they had had the whole night to plan and scheme...something he would bet his last dollar on that they did regularly.

"Aren't you ladies going to join me?"

 

[wickedpen]

"Oh no dear" Aunt Jean started putting her hands on his shoulders and massaging them softly. "We are here to please our man. Anything he wants we will certainly try to provide" she said with just a slight hint of sarcasm.

"You are the man of the house today. We are going to treat you as such" Tracy said with a smile that could melt any man's heart.

"Your mother called last night" Aunt Jean continued "and she was a bit concerned about you. She said there were some items missing from her drawers that she found, disconcerting. Do you know what I am talking about?" Jean said now walking behind Ann. "I assured her that you were a red blooded male with not a hint of girly in him." she said with a smile.

Ann jumped in now, "we only want to provide what every red blooded American male would want on his summer vacation, turning eighteen." she said in a voice that stiffened the wettest cardboard.

"Now we are going to let last night go, as I know you are not that girly man." Aunt Jean continued. "Today we are going to hopefully see a man who takes what he wants.." Ann and Tracy leaned back from the table pushing their chests out and looking more serious at him, almost challenging him. "Aren't we dear? I would hate to tell my dear sister her big strong son wants to sniff panties and wear dresses." Aunt Jean said with a laugh then returned to the kitchen.

 

[georgerb]

Jason definitely heard his Aunt's tone of sarcasm, as well as Tracy almost doing a parody of Ann's normal demeanor. All to scripted he felt, but he couldn't resist the offer even if knowing there would be consequences... on doing something or doing nothing. Damned if he did or didn't. And he knew that realized that.

At first, hearing of the conversation between Aunt Jean and his Mom sent a bolt of fear through him, but he couldn't really trust anything she said. Hell, he had no way to trust anyone right now but that was it's own temptation in a way. So many what ifs.

He'd bet that most men have at one time or another wore panties, even if on a dare.

Standing up, he walked around towards where Ann was setting, betting she was the safest course of action. It was more than insinuated for him to do something. He reached a hand under her dress and found her pussy, bare as her top was. Betting she would be receptive, he plunged two fingers into it, causing Tracy to exclaim, "Damn it...I hate being second choice!"

His cock grew and reminded him he still had Tracy's panties on under the shorts he pulled on when he got up.

 

[wickedpen]

Aunt Jean looked over as Jason looked towards her. She turned and faced the window over the sink and then pulled the skirt of her dress up until her naked ass was revealed.

"Doesn't momma get something for making such a good breakfast?" she cooed without looking back.

 

[georgerb]

Jason had his fingers deep into Ann's pussy and glanced towards the kitchen as he heard Aunt Jean's voice..

"Doesn't momma get something for making such a good breakfast?"...

...and watched her bare her ass at the sink.

He abruptly pulled his finger's out of Ann's wet hole and went to the kitchen, standing behind his Aunt. Reaching a hand around her and grabbing a breast and squeezing it...wondering if his Moms' felt the same.

"Well, they say if Momma ain't happy, no one is."

His other hand did his best to pull the front of his shorts and the silk panties down under his balls, then guided his cock between her legs. The tip just grazing her pussy lips now and then.

Ann was pissed that her Mom stole him away, and now Tracy felt she was third choice. Jason didn't give a fuck, he was to busy enjoying the feel of Aunt Jean's offering.

 

[wickedpen]

Aunt Jean's smile went unseen as she felt Jason behind her and then he grabbed her tit.

"Give momma what she needs, like a man" Jean moaned as she felt him bring his cock between her legs. "OH Jason take me, make me your woman. Fuck me" she hissed. She encouraged as much as instructed and arched her back for him.

AS he tentatively eased himself into her she reached back and grabbed his hip pulling him into her. "Is that how you imagined taking your mother?" she hissed as if reading his mind. "Gentle like a fawn?" her tone was sarcastic and annoyed. "Fuck me Jason!" she commanded and then spread her hands on the counted to brace herself as she pushed he hips back into him.

"Momma, maybe he is just gentle, ya know?" Ann said defending her cousin.

"Yeah mom maybe he is just a pussy?" Tracy said with a laugh and a glance at Ann disgusted.

"So what is it boy?" Aunt Jean asked as Jason stood motionless with his cock half way into his Aunt. "Karen said you were a wimp. Imagine that, your own mother calling you sexually confused." Jean said with a laugh.

 

[georgerb]

Aunt Jean's voice hissed in that increasingly familiar tone, one that Tracy often mimicked. Confused with emotions over her insinuation that his Mom had actually spoke to her about stuff like this. But in a sidelight was thrilled that she had.

With Aunt Jean's hand on his ass and her obvious stance he rammed into her, thinking of all the porn videos where MILFs and Moms got their desires. With the waist band of the panties cutting sharply up into his balls, he fucked his Aunt hard. So much better than doing so in his hand covered with panties as he spied on his Mom.

Reluctantly letting go of her tit, he grabbed her ass cheeks, not bad for her age by the way, and dug his fingernails into the supple skin. Pumping in and out of her and the physical pleasure for sure as well as the emotional part of her being his Mom's sister. And a small part of him wondering what his two cousins were plotting behind him.

Sometimes the risk of actions taken gave consequences later. His balls didn't care...they just tensed and released his morning juice into his Aunt.

 

[wickedpen]

Jason was giving her a good fuck but she felt his stiffen and cum way to soon. She wrapped her legs around him and looked up at him.

"That was quick" she said without remorse. She was brutally honest. "I didn't even get close and that is what is the true test of a man, if he can make the woman cum." she explained. She moved her hips enough to keep him interested as she spoke.

"So Jason," her hips embellished her words. "You didn't call me momma?" she said as his cock jumped inside her. She smiled an groaned as they both felt it and knew she was massaging a nerve that ran straight to his libido.

"She left her panties out for you" she continued as her hips gyrated slowly. "She always hoped you would be overcome with desire or need and approach her. So why don't we pretend so when she picks you up at the end of the summer you are ready. Now what do you imagine she would call you if you two were in this position?" she said with a smile as his cock beat faster than his heart which was nearing the breaking point.

 

[georgerb]

He felt rebuked by his Aunt though still riding the high of fucking her. He supposed he should care about the orgasm part, but his hormones were raging, despite hearing Tracy and Ann chuckle behind him. He guessed they thought it funny that Aunt Jean was suggesting he call her Momma.

His cock was already twitching over hearing that his Mom had hoped he would do something...he never even thought that a possibility. Then again, he had no clue about his Dad fucking his Aunt either. He kind of wondered how long that had been going on. Longer than that old video?

He backed up and out of her, his cock almost chilled by the room air. Aunt Jean looked down at it as he said, "Suck my cock, Momma."

Again the giggles from behind, but they both moved to either side to see what Mom would do.

 

[wickedpen]

Aunt Jean's lips turned into a smirk as she reached out and wrapped her strong hand around my cock and squeezed.

"We better get you good and hard first" she said. "Girls come grind on your cousin with those bodies. In your clothes but rub those tits he likes so much against his arms and back.:"

Aunt Jean stood in front of him and slowly jerked him as Ann on the right and Tracy on his left quickly pushed his biceps into their cleavage and bent their knees to grind into his hip. They each kissed then bit his ears and breathed into his head fueling his fire.

"Oh cousin I want that big dick next!" Tracy groaned nearly to orgasm.

Jason I will wrap my panties over your face as I ride that cock" Ann sighed running her hand down his ass.

Aunt Jean dropped to her knees and took his head into her lips as she held his stare.

 

[georgerb]

Jason shivered at his Aunt's hand stroking his cock, still wet with juices from her pussy. Though his cousins nibbling at his ears also caused his balls to shrink up a bit with a tingle that ran down his spine, almost in they exact movement of Ann's hand down on to his ass.

As Jean's mouth took in the tip of his dick, he stared back at her, realizing how close they were to his Moms'. He worried that she would bite for some reason as he also wondered what she said of her sister was true.

With his cousins rubbing their tits on him and grinding their pussies on his leg, he pushed deeper into his Aunt's mouth.

"Momma likes her boy's cock?"

And part of his brain thinking of Ann's panties on his face....

 

[wickedpen]

Aunt Jean's eyes closed as she began to take as much of the cock as she could sliding forward as Jason thrust into her and then locking her lips on as he pulled back.

"Fuck Jason, I want to ride that shaft" Tracy groaned as she ran her hand over his chest.

"Yeah Jason don't waste it on on mom" Ann said as her fingers slid down nearing his ass.

"Are you gonna cum in mom's mouth Jason?" Tracy sighed into his ear with her warm breathy voice.

"Does it feel good?" Ann asked as she reached down and put her hand on Jean's head to move her in unison with his hips. "Fuck her mouth" Ann said more forcefully.