The Chauffeur 3 First Day Jill
- 2 years ago
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Help From Jill free porn video
He walked slowly down the hall to the bathroom naked. Not even concerned about who might see him. He cold hear everyone downstairs having a good time at breakfast. After using the bathroom he stopped in front of Jill’s room and looked around. It was neat, clean and organized except for some clothes including a pair of black panties laying on the floor. He briefly wrestled with the thought of sneaking into her room last night to try on some of her clothes. The urge to dress like a woman was becoming unbearable. If he didn’t do it, become a woman soon he might go crazy. He had already started trying on Kate’s clothes at home but they were a a bit big on him because she had such nice curves. He’d thought about trying on his step-mom’s clothes but hated the clothes she wore. She looked like white trash to him. Even the thought oftaking photos of himself in womens clothes made him excited.
He looked around and made sure no one was watching before he slipped over and picked up the panties. He gave them a quick sniff. They were for sure dirty. He slipped them on and walked back to the bedroom he and Kate were to share but his Mom had spent the night having a lesbian threesome in Joy’s room and he had fallen asleep in Joel’s room. He felt comfortable in the snug undies. Their soft smooth material against his balls felt great.
He pulled on a clean pair of jeans and a long sleeve shirt and headed down for something to eat. He sat at the eat in kitchen table between Jill and Joel. Joel put a hand on his leg and gave it a little squeeze. Jill did the same on the other side. Sending his dick into attention mode. Joy smiled a big happy smile and slid a cup of coffee in front of him and a plate of pancakes and bacon.
“ not shocked everyones all smiles this morning considering the epic sex that everyone had last night." He thought to himself and smiled.
He ate slowly but downed the coffee for a refill as he listened to everyone planning their days.
Joy and Kate were going to visit old friends from school and Joel had to work and would not be home until late evening. Davie was disappointed as he really wanted to have Joel to himself today.
Jill had nothing going on and was just planning to hang out around the house and relax on her day off from training for her track meet, so she said that her and Davie could go to the mall and do some shopping, hang out and do whatever there.
“Or we can fuck” she whispered in his ear.
That is when Davie decided it was now or never.
He felt safe. He knew no one in the room would be cruel or judgmental after all the incest that went on under this roof, and the fact Jill, Kate and Joy had been having a lesbian threesome late in the night last night, a trans person would be the least racy thing going on. So he told Jill he would love to go to the mall as he wanted some new clothes.
When his Mom Kate asked what he wanted to buy he let it all out. How he wanted to become a trans woman. He wanted to be softer, more feminine, he was’t a guy he was a girl deep down.... well not even that deep. She was right there ready to come out. He even admitted to wearing a pair of Jill’s panties.
Jill smiled at the thought of her dirty panties covering a dick.
“well you’re in luck Davie hunny” Joy beamed with pride. “Jill has already had experience helping a young man transition. When she was done helping him he looked more feminine than she did.”
“well Jill is a bit butch.” Joel teased his sister. “You know being a dike athlete, eating pussy, weight lifting and shit” Jill and Joel were actually very close. She gave her brother a slap in the arm.
“Joel your such a queen everyone seems manly” Jill teased.
They all laughed.
“it’s true Davie” Jill beamed. My ex boyfriend Kevin, well, now Lila asked me to help him transition. Well he told me what he was going to do and I offered to help how I could and ended up taking him to buy shoes and shit. We aren’t together anymore he decided he wants only cock in him but we are really good friends, even act as her wing woman sometimes” She sat back taking in her cousin. “it’ll be easier helping you though, he was quite boyish, you already have long hair and soft features and great cheek bones. Plus if your wearing my dirty knickers you clearly don’t mind hand me down clothes. I may already have some clothes you can have. Then I can get some new stuff too”
Davie smiled a wide grin. “thanks Cuz” Jill gave him a playful wink.
Slowly everyone made there way out of the dinning room and out of the house to go to get on with their day leaving Jill and Davie who was still eating to discuss little things like what he wanted his look to be, what they should do first and had more coffee to get them started.
“well my dear" She finished her coffee. “Time to make you a broad. Or at least tart you up some" They laughed. Davie could tell it was going to be a very positive day.
They went up to Jill’s room. All she was in was a pair of pink plaid pajama bottoms that hugged her toned ass tightly and a white t shirt barely containing her breasts and semi-hard nipples.
She went to her closet and pulled out a large box of clothes that did’t fit her any more. All kinds of things like jeans, tights, shirts, bras and panties. He took the box and looked through it. He took out a couple pairs of jeans, a few tights and then put it all back and decided to take everything. There were the makings of at least six outfits in there. He needed a wardrobe he could wear everyday and this was a great start. She tossed a couple more skirts, blouses and a one piece bathing suit on the top of the box.
“You can have those too. I’ve lost a lot weight since I started training. I think it will be a bit tight on you but not really tight so it’ll look sexy"
“wow! thanks Jill!"
When he turned around Jill was laying on the bed. Propped up on her elbows completely naked. She was grinning at Davie as his cock shot to full attention.
“Listen Davie” She purred. “My services aren’t free” All he could do was take in her body, she practically had a six pack she was so fit. No wonder clothes didn’t fit her, she wasn’t so much skinny as she was toned and had amazing muscle definition. Better than even a dancer. She looked healthy, super fit and athletic her training must be going very well. Her long legs were smooth and shiny, her dirty blonde hair fell around her face framing it in an almost angelic light. “I am going to need you to fuck me. Maybe a few times” She opened her legs leading him to look at her tiny landing strip of pubes right above her pussy. “At least once for my consulting services and once for that box of clothes” She spread her legs farther and began masturbating. “ I hope your as hung as Mom said you are. I spent last night with two women. I need some serious D now” She bit her lower lip. “No condom either. Bareback me. I’m ready to go right now. No foreplay. Just fuck me”
“I think I can help with that” He said as he took off his pants and shirt and then the panties.
“you can just keep those dirty panties. They have my come on them anyway” she said as he knelt between her legs and began licking her nipples.
Not one to take her time she guided his big cock to her pussy and into her. She needed it hard and needed it now and Davie was all too eager to help.
“fuck you are just as big as Joel” She moaned as he pushed in up to his balls. She wrapped her legs around him and grabbed his hair as she matched his hip rhythm. “yes Davie fuck me” She cried as the beginnings of an orgasm were already gripping her. “fuck me hard”
He couldn’t belive how fast she came. It was amazing. He had masturbated to her photo, it was like a dream come true as she moaned and yelled for almost five minutes. He was so turned on he came too. He came deep inside her. She smiled and kissed him. Keeping her legs wrapped around him.
“I have wanted to do that for so long” he panted, kissed her again. “since you posed those bikini photos last summer”
“those photos have gotten me so much cock its embarrassing.” She said humbly. “ But I have wanted you too, ever since I could remember, I used to masturbate thinking of you too Davie. Lets fuck again later. Lets be fuck buddies forever”
He just smiled and nodded. “fuck yes” was all he could say. It was his greatest fantasy coming true. He might even get to be with her and Joel together.
“Okay now lets make you a really cute person of the feminine persuasion” she purred.
She went and started the shower. She brought him in the shower with her. Showed him how to shave his legs, pits, arms, chest and pubes. There was no hair on his back so she didn’t need to help him. But he listened to pointers on technique and types of products to use for razors and soaps. She described her skin rituals and how what soaps she liked. When they were done they were both smooth and she shared her moisturizer with him. Telling him to use it daily to keep his skin soft and supple looking. She then said they were now ready to get dressed.
As they toweled off he put her up on the counter and knelt in front of her. Spread her legs and proceeded to give her oral pleasure.
“this is for the grooming tips” he said as he probed her pussy with his tongue. Licking all the way back to her anus. Parting her labia and swirling along her sensitive inner area. He worked his way to her clit. Making more swirls with his tongue as he inserted three fingers in her and tickled her g spot. Sending tingles and waves of happy through her body. He used his other fingers and pinched her nipples, teased them to be as hard a possible. She grabbed his hair and humped his face. Her heels now up on the counter and she leaned back against the mirrored wall. His loud licking was about to blow her mind. No one had gone down on her like this before. Not even any of the women she had had. She growled, moaned and howled as she came in his mouth. Then for good measure he slowed down kissing along her inner thighs, then back up and licked along her pubic hair back to her clit and kept going. He went back to eating her pussy again. Pinching and playing with her nipples even more. But grabbed her legs and spread them as far apart as they could go getting his whole face buried in her watering pussy.
Her voice getting horse from the constant vocalizations. She fucked his face to her third orgasm in an hour. She pulled him up to stop him. If he kept going they would get nothing done. After a deep kiss she hoped into his arms and he lowered her down off the counter.
Wearing only towels they went back to her room. He watched her technique as she put on a red lace bra, red panties and pulled on a pair of jeans. She then pulled on a black baby doll shirt that showed her navel. But he was also sad she was covering up her banging body (that he wanted to bang again).
She then guided Davie as to what she thought we be good for him to wear for the first time in public. He put the dirty panties back on to her great delight. He was really enjoying the thought of wearing her dirty undies with her cum in them. Then a black bra. She was impressed at how easily he could do up a bra. He had clearly practiced that. He chose a jean skirt that was worn just above the knee and a dark blue long sleeve t shirt with a button up v neck to go with it.
“now” She said looking at him, hands on hips. “I don’t have shoes that will fit you. Your feet are bigger than mine or Moms and Joel does not crossdress. And so that is mission one at the mall. Get you some more girly footwear. I bet you would look hot in a red dress too babe. Lets just shop till we drop hey.
Second you cannot keep calling yourself Davie can you? Not a great name for a really cute girl. So have you thought of a new name? Darcy? Daria? Assuming you want something close to David”
He shrugged he hadn’t. She told him to think about it as she gave him make up pointers. How he applied eye shadow, mascara, a little foundation and lipstick. She told him he already had fairly soft, even cute features so it wasn’t too hard to do, he wouldn’t need a lot to make him into a cutie. He liked being called a cutie.
He brushed his long hair so the bangs flipped to one side. Jill said it made for a flirtier look.
When they were done he....she looked at herself in Jill’s full length mirror. “wow is that really me?”
“told you you’d be a hottie” She put her arm around her cousin and they hugged.
“Now we have no vehicle so we’ll have to take the bus. That cool with you? It’ll be your first time out like this. Don’t want you to freak out. How confident do you feel about your look right now?”
“actually Jill I’m good. With you with me I feel really safe. Plus. I have dreamed of doing this for months. Let’s go”
“right on. Right on but first things first.” She pushed her jeans and panties down. Then lifted up the jean skirt. “I need more dick. I find this whole situation really fucking arousing. I’m a freak I guess”
He just smiled and pushed her up against the wall and spread her legs. “You and me both hot stuff" Pushing down the front of the dirty panties she pushed into her from behind. Keeping one hand on the wall she reached around and squeezed her cousin’s tits as she turned her head and they kissed as she pounded her first pussy as a girl. It was so intense that she felt this new her would have an insatiable sex drive.
“Fuck Davie. Your so sexy. I can not deny how hot I get around you can I?" They French kissed. “Can’t wait for guys to see you like this. You will get so much cock. Pussy too I bet” She deep fucked Jill and bit her neck as she pushed back on her cock. “You and I have similar sex drives too.”
“I know right. Lets fuck again later.” she growled. Squeezing Jill‘s firm tit tighter through her top.
“lets fuck at the mall!” She said as she came again.
“oh god yes” she moaned. The thought of having dirty sex in a stall at the mall made her cum. So much come that it literally was dripping out of Jill’s now well used pussy.
Jill went and cleaned herself up. When she returned she watched Davie as she pulled on a jean jacket and did turns in from of the mirror.
“So ready to go cuz” She slipped on a pair of sneakers.
“Amy”
“sorry what?”
“that is what my name is now. Amy. David no longer exists.” She licked her lips.
“okay Amy. Lets get to the mall before we start fucking again.” They giggled and headed for the bus stop.
They sat near the back of the bus. It was a quiet Saturday so it was only half full. Jill gave pointers on how to sit and act lady like in public. Amy took it all in and mirrored what Jill did. They giggled and laughed and enjoyed themselves as they got off the bus Jill whispered to Amy that the bus driver had been looking at their asses.
“I think old pervs should get to look all they want Jill" Amy said with a smile. “gives them something to think about in their lonely beds at night"
They went straight to Jill’s favorite shoe store in the mall. It was trans friendly she assured Amy. They were having a sale too. As they walked in an older woman name Lara approached them.
“Hi Lara this is my cousin Amy.” Jill clearly knew Lara already. Lara looked at the mens sneakers Amy was wearing and smiled.
“Yessss. Well. Hello Amy how can I help?”
“Well” Jill continued. “as you can see she desperately needs more appropriate foot wear. Some heels for sure. Maybe a decent sneaker too”
“Yes I see. I can certainly help” She motioned for Amy to follow her. “This way please sweetheart”
“While you two chat I am going to try on some boots” Jill bounced away with a wink and a smile. Her enthusiasm almost contagious.
Lara took Amy to the heels section and sat here in a chair. She asked some questions as to what Amy liked. Amy had no idea what she wanted or even her proper shoe size. So Lara started by measuring her foot. After walking Amy though some options it was clear there was a certain level of discomfort.
“first time doing this honey?” Amy stared at her with a worried look and gave a slow head nod. “It’s okay. Your among friends here.” Lara put a hand on her knee. “I have a son who used to be my daughter. I understand what your trying to do.” Lara was very disarming and had a very kind trustworthy face. “Just keep those pretty legs closed. Short skirts might give away that sausage your packing okay.” Amy squeezed her legs together and smiled uncomfortably.
“Sorry” Amy said.
Lara gave her a warm smile “don’t be sorry Amy. No one is themselves right away” They smiled at each other.
“Here try these. They are a moderate heel. Good for beginners.” She put black pumps on Amy and she slowly stood up. Having never worn heels before she took a few awkward steps. Feeling shaky at first but gaining balance she walked around the store a bit and found Jill wearing a pair of dark brown knee high boots.
“aren‘t these the cutest boots Amy?”
“Jill. I feel weird. Never walked in heels before.”
“You’re doing fine. Really!” Jill gave her some direction on how to walk in heels.
They walked arm and arm around the store together. Jill said she should buy the shoes and wear them home. They looked good with her outfit.
Amy told Lara that she would wear the shoes home but also wanted a pair of red ones Since they were buy one get one half off. She also found a pair of pink and black sneakers and Jill bought the boots. As they were leaving the store Amy hugged Lara and thanked her for all the help.
Jill just waved at Lara. “good to see you again Lara”
“You too Jill. Another fine job done” Lara nodded at Amy and all three smiled.
It was Lara who had helped Jill’s ex too. Many people went to Lara for help with their new looks.
They stopped at the food court and had a cold drink. They giggled and had fun looking at boys and girls walking through the mall as they noticed two guys flirting with them from the next table. Jill asked Amy which one she liked. Amy responded by saying the one in the red shirt. He was dark skinned and clean cut looking. The other guy was just as dark skinned but had dread-locks. Jill smiled because she thought dread-locks was cute.
“Amy, I dare you suck him off in the bathroom” Jill leaned in closer. “but you can’t tell him till after that your trans.”
“well Jill. It so happens Amy really wants to hook up with a black man sooooooo.” Amy just smiled and winked at red shirt.
They got up and came over and sat down. Jill immediately began coming on to the long haired guy and they soon took off. The girls winked at each other. Jill really is a sexaholic Amy thought. But it was becoming clear she was too. After some small talk with Mace (that was his name) she leaned in and asked him how big his cock was. When he went quiet she told him he could show her instead. Maybe she could help him bust a nut.
Speechless at first he told her he was ten inched fully hard. When she did’t belive him he offered to prove it. They left the seating area and he took her into the mens room. They snuck into a quiet stall and he stood while she knelt on the floor and unzipped him. She pulled out a long thick cock. Even longer than her own or Joel’s. She started devouring it right away. Gagging and making sure there was lots of spit to lubricate the big dick in her mouth. He reached up and grabbed the stall walls. He came in her mouth very quickly with a groan and a gasp. She was sad she didn’t get to give him a nice long deep throat. But some boys just don’t know how to hold out. There wasn’t as much fluid as she expected either and she swallowed it all easily. Leaving not a drop.
She stood up and fixed her clothes as he tucked himself back in. “That was amazing Amy. Damn girl you can suck a dick.”
She smiled at him. Thanks stud. “Too bad you cum so fast. Not very sexy. Plus, I suck good cause I know how good having your cock sucked feels.” She kissed his cheek.
“wait how do you know that?”
“Think about it” She giggled and walked out of the stall and the mens room. He stopped her in the hallway.
“You mean you are ah-ah-ah”
“That’s right sweetness.” She whispered in his ear. “A trans girl just swallowed your cum”
She walked away. Leaving him to ponder the situation.
When she returned to the seating area Jill was there playing on her phone waiting. She had been in the backseat of dread-lock’s car for a very disappointing fuck.
“looks like we found a pair of minute men Jill said sadly"
They got on with their day. They went to a clothing store and tried on some stuff. Jill handed Amy a dress and told her put it on. It was a retro fifties looking dress with pleated hem and short sleeves and a black belt. She looked like an old school teenager.
“You wear this, maybe with black stockings and a red garter. Match it with red bra and panties you will look and feel so good.”
So she bought the dress along with red, black, flesh and blue stockings. They didn’t have garters. After that they were low on funds so the girls headed for home. By the time Amy had negotiated getting on and off the bus in heels she felt much more confident in them.
“and your ass looks hot in them Amy"
When they got back into Jill’s room Amy tried on more of the clothes in the box, mixing and matching outfits. She ended up with eight new outfits plus the red dress.
She was in a black pleated skirt and black stockings. A royal purple shirt that was tight enough to see the pattern in her bra. She sat on the chair to adjust a stocking and put on the black heels when Jill put her hands on Amy’s shoulders and pushed her back in the chair. She knelt over Amy and kissed her long and with tongue. Amy squeezed her cousins ass as her dick grew hard again.
Jill stood and took her jeans off again as Amy pulled her skirt up, pushed the panties down and pulled her dick out. Jill settled back on top grabbing the back of the chair as she lowered herself onto Amy’s big hard dick.
Caressing Jill’s ass as she moved up and down the two girls kisses and bit each others lips.
“I can’t get enough of you in me Amy”
“Good to hear” Amy squeezed Jill’s ass tighter. “ Thanks for everything Jill”
“ now you know my fee for further consultations. So no further talking until we both cum”
They moved in sync. Their bodies creeping closer to climax. Jill pulled off her top then her bra. Amy buried her face in those firm tits and sucked each nipple. Jill moaning in approval with every lick and suck. Jill could not remember the last time anyone had made her this wet. Except maybe her coach a few weeks ago on the road after she won. They fucked in celebration in his hotel room.
Without a whimper or a moan Jill began to shake and shutter and came only seconds before Amy. Both of them stayed in position kissing and touching each other.
Amy thought sex with her cousin Joel would have been the highlight. Jill had seemed too unattainable. Maybe even goddess like in her physique but here they were after having sex for the fourth time in less than six hours. He could not choose which cousin he was more into. Oh how amazing.
“Amy. you should wear that to show Mom and Kate. You look really good in it.” She kissed Amy again and stood up. She was topless but had pulled her old distresses Levi’s on when her phone buzzed.
“it’s Mom they’ll be home in ten minutes.”
“Jill you have the nicest tits I have ever sucked on"
“Suck ‘em again later if you like" They giggled out loud.
Amy stood and pulled her panties back up and her skirt down. She smiled at the thought of hers and Jill’s cum mixing in those very dirty panties.
The heels in place she fixed her stocking, make up and hair. Jill put an arm around her waist and kissed her cheek as they heard their Mothers coming through the front door.
“Well Miss Amy. Are you ready to see what your Mom thinks of your new look?”
“I am”
To be continued......... -->
Nanette
- 23.07.2022
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