Training Her Baby (Part 37 added 11/29/2020)

[Sarah Penguin]

[CDfm]

Wow I would have a hard time accepting that my wife was wanting to sleep with someone else. Even if I was being turned into a sissy baby. I am also a little confused that they would be wanting Nancy to crave cock. I would think they would want her to pleasure women so they could be better satisfied. I am looking forward to reading more. 

[Sarah_Hillcrest]

Yes good point, but Cindy gave Pam the new hypno CD only telling her it would help with wetting and feminization.  She hasn't listened to it.  I would have a hard time accepting that my wife wanted to sleep with someone else too. 

[Sarah_Hillcrest]

Training Her Baby Part 31

Complications at Work

 

“I’m sorry Baby but you’re going, it’s already been decided,” Pam said.

“Why can’t I just stay home?” Nancy whined.  She’d just been changed into her morning diaper and stuffer and waiting to be helped into Jim’s work clothes.

“We’ve been through this Babydoll, we both know that you can’t be left alone. I’ve made up my mind,” Pam said.  Nancy huffed and folded her arms, she had been thinking of having this Tuesday evening home alone for a week now.

“I’m not going to your stupid meeting, and you can’t make me!” Nancy said.

“You know you’re turning into a real brat!” Pam shot back.

“Fine I’ll be a brat here at home,” Nancy said.

“I told you, I volunteered you watch the children, it’ll only be a few hours,” Pam said.

“Why did you do that, if anything you should have volunteered someone to watch me!” Nancy said.

“I told you, Cindy and Sally are both busy tomorrow night so they can’t watch you and Gretchen’s husband is busy so we needed someone to watch the children while we have our meeting, so I volunteered you,” Pam explained.

“But..”

“We both know if I left you at home, you’d probably tear your balls off trying to get to your little clitty,” Nancy said.

“Well you’re little clitty is getting plenty of action, you see to that I’m sure,” Nancy snorted. Pam wasn’t sure how much of this bratty act was real, and how much was just playing around but she had enough.  She reached forward and grabbed Nancy diaper and ripped it off tearing the sides.  The Pampers stuffer fell out on the floor.  “Hey, what the hell, you just ruined that diaper.” Nancy said.  She stood nude except for the pink chastity cage.

“That’s enough out of you.  You can’t behave so I’m taking your diapers away,” Pam coldly said.

“Wait what?”  Nancy said.

“You heard me, no diapers today,” Pam said.

“Is that supposed to be a punishment?” Nancy asked.

“You’ve been in diapers 24/7 now for 4 weeks, you know how much your bladder’s already shrunk.  You’ll be praying for a diaper in an hour,” Pam said.

“Well how about this?” Jim said in his old masculine voice as he grabbed his balls and lifted up the cage.

“Nope that stays on, if I unlocked you, you’d probably have an accident on the way to work trying to whack off in the car,” Pam said with a laugh.  She tossed Jim his khaki pants and dress shirt then left the nursery.  Jim stomped out of the nursery into their old bedroom and went to his underwear drawer in the dresser.  It was full of panties.  “Pam where the hell are my boxers!” Jim yelled.

“I threw them away, those are my old panties, just pick one out if you want,” Pam answered from the doorway while she inserted an ear ring.

“You threw them all away?” Jim asked.

“Yeah, you don’t need them anymore, plus I know you’d prefer to wear panties if you can’t wear a diaper,” Pam said.  Jim felt himself swelling in his cage and turning red.  His wife kept finding new ways to humiliate him, but he was not going to be a baby sitter.  He pulled on a pair of plain classic white cotton panties with a little bow on the waistband and Pam walked off snickering.

Jim’s commute was short, he could be to work in less than 20 minutes, but today’s drive felt much longer.  For weeks the part of Jim’s brain that was responsible for holding his bladder had been on vacation, and now he was asking it to come back to work.  His need to pee occupied his every thought, He rushed from the parking lot, and straight into the bathroom on the first floor.  Standing in front of a urinal felt so alien, and then the pee began to dribble and run down the cage.  “Geeze,” Jim said as he quickly rushed to a stall to wipe himself off and pee sitting down. 

It was a typical Monday morning, if you could call any morning at AMP Marketing typical anymore.  A sense of dread had settled over the employees, rumors of the bankruptcy were growing every day.  One of Jim’s team members had already quit to take a job somewhere else and just about everyone was looking.  Jim dropped down into heavily into his chair.  He felt groggy, despite being keyed up from the morning’s argument, even worse he felt naked without his diaper on.  His empty coffee mug stared at him.  Jim felt a slight need to pee, but decided to ignore it, he had just went five minutes ago.  The first order of business was to prepare for a 10:00 meeting with his team. 

Jim took a drink of coffee from his now filled mug, he just couldn’t seem to focus.  By 10:00 the mug was empty and Jim had just finished printing out materials for the meeting.  The slight need to pee was stronger but he didn’t have time he could see everyone assembling around the table.  “I’ll just make it quick,” he said to himself.

“Well I’ve heard that corporate plans to let everyone go in December, right after we’ve done all the Holiday campaigns,” Jill said.  Jim glanced at his watch, it had been nearly 30 minutes, and the need to pee was overwhelming.  Just as Lou was about to add his two sense Jim felt a sharp pain then an actual squirt.

“OK guys, I’ll be right back,” Jim said as he rushed out of their conference room.  He dropped a folder on his desk and looked down at the front of his pants, there was a tiny wet spot.  He began walking as fast as possible towards the executive bathroom as was fiddling in his pocket for the key.  His steps were jerky as he could actually feel small squirts being released as he walked.  He was sweating, and getting a couple of weird looks from his walk.  He entered the small back hall where the executive bathroom and watercolor were and saw Ted smiling by the watercolor talking to Doug’s secretary.  Jim felt a sharp spasm, involuntarily his knees buckled, he doubled over and wet himself.  Jim felt it running down his legs and collecting in his socks, he looked down to see a quickly expanding stain expanding around his crotch.  He looked up and saw the secretary had covered her mouth with a manila folder to hide her expression, but Ted’s mouth hung open.  “Umm, are you OK,” he asked.

“Fuck no I just pissed my pants,” Jim said as he glanced behind him.

“You’re dripping on the floor, do you have some other pants or something?” Ted asked.

“No,” Jim replied.  The sound of people talking could be heard and few people turned the corner into the hallway.  Jim glanced back again, he was fighting the urge to take off running.

“Wait, I’ve got an idea.  Hey Jim, what’s up buddy,” Ted said overly loud as he begin walking towards Jim, he bumped into him and purposely dumped his cup of water right into the front of him.

“What the hell,” Jim yelled out surprised and not realizing what was going on.

“I’m trying to cover for you man,” Ted whispered.

“Shit, oh damn man, I’m so sorry,” Ted said as he stepped back from Jim.

“I’m soaked man,” Jim said.  The employees stopped, and watched the scene, one of them chuckled a bit.

“Man you live pretty close don’t you, you could run home and change pants,” Jim said.

“Dude, take the stairs, they’re right around the corner,” one of the employees said. 

“OK yeah, good idea,” Jim said.  He had to walk through about half the office to get to the stairs, he got a couple looks but no one said anything.  Crossing the parking lot people walking towards the parking lot were noticing, the stain was so much darker then the rest of the pants.  A few snickered.  Jim was turning red and fighting back tears. 

He climbed into his car slammed the door then called Pam.

“Whats up, hon,” Pam answered. Jim began to bawl, he couldn’t catch his breath and couldn’t get his words out. “What’s wrong honey, calm down.”

It took a few moments and Jim blew snot out of nose onto his shirt before he spoke.  “I just wet myself,” he said.

“Oh my God, did people see?” Pam asked.

“Yes, I did it right in front of Ted and Doug’s secretary,” Jim answered between spastic gasps of air.

“Oh I’m so sorry, I’m so sorry,” Pam gasped.

“I can’t go without diapers now, I’ll wet myself again,” Jim said. 

“Oh baby, I’m so sorry, I should have never made you go to work without protection, I never thought you’d have an accident” Pam said.

“I shouldn’t have argued with you, it’s my fault.  I don’t know what to do,” Jim said and began to cry some more.

“Listen, Mommy loves you, it’s going to be OK, you’re going to be fine.  I can’t leave work right now, but  go home, put on a diaper, change clothes and go back to work.  People have accidents, it’s no big deal.  When I get home we’ll talk OK.”

“OK Mommy,” Jim said in Nancy’s voice.  “I love you,” she said.

“I love you too babygirl.” 

[CDfm]

How does he explain that when he gets back to work? Now, because of the accident people are going to be much more attuned to his crotch and much more likely to nothing the diaper. At this point he should be hoping the company folds really fast just to save his reputation. I am looking forward to reading more. 

[Sarah Penguin]

[Sarah_Hillcrest]

OK, I don't want to toot my own horn, but I love this chapter, it's probably one of my favorite things I've ever written.  It's kind of complex jumping through time a bit at the beginning.  JIm is refered to as Jim until near the end of the chapter when he becomes Nancy.  So if you haven't been following along Jim = Nancy.  Pam is his Mommy/wife.  Cindy is the Dom and Sally is her trans wife.  Let me know if the opening part is confusing or if it flows as you read it.

 

Training Her Baby Part 32

The Halloween Party

 

“Hey folks Happy Friday to you! Hey you know that most spooky time of the year is fast approaching, how about a little something to get you ready for Halloween,” the DJ said and the opening bars of Michael Jackson’s thriller came on the radio.  Jim shifted nervously in the passenger seat. 

“Pam, I don’t know about this,” he said.

“Would you please relax,”  Pam said and glanced over at her sissy husband fully dressed in his work clothes, then glanced back at the garmet bags in the back seat.  “I really don’t get it, I thought you’d love this idea,” she said.

“Oh I love the idea, but it’s the execution that’s got me scarred,” Jim said. 

Eleven days ago he accompanied his wife to her women’s club meeting to be the baby sitter.  Something he was quite nervous about, but it turned out to be no big deal.  The ladies met at Sophies big house to plan out their annual Halloween costume party.  The ladies gushed praise and thanks of Jim for volunteering to watch the 4 children during the meeting.  Jim to admit that he hadn’t exactly volunteered, in fact he’d argued and been punished for it, though the punishment didn’t work out exactly as Pam had planned.  Taking away Jim’s diapers for the day revealed that he couldn’t trust his bladder, he’d wet his pants right in front of one of his good friends at work.

Monday after work Ted cornered Jim as he was about to get into his car, “What happened this morning man?” he asked.

“You saw what happened,” Jim replied.

“You pissed your pants, yeah but what’s going on?” Ted asked.  In the past Jim would have just made up some story about drinking to much coffee, or a bladder infection, but Nancy wanted out, she wanted him to be exposed.  Jim began to sweat, he wanted to tell him he was a sissy, an adult baby in diapers, but he decided to split the middle right between honesty and lying.

“About 4 months ago I started wetting the bed, so I started wearing, um diapers to bed.  It wasn’t long that during the day I was constantly worried about having an accident so I started wearing diapers all the time.  Yesterday I wanted to try not wearing and, well you saw what happened.”

“Diapers?” Ted asked.  Jim loosened his belt and pulled the side of pants down just enough to show his friend the shiny white plastic of a Tranquility ATN adult diaper.

“Oh, wow, I umm… Have you been to a doctor?” Ted asked.

“Yeah, they can’t find anything wrong with me,” Jim said. 

“Wow, man I’m really sorry,” Ted said.

“You really saved my butt this morning, that was quick thinking,” Jim said.

“Well yeah, but Secretary Jones saw it too, and she isn’t known to be the best at keeping secrets.”  On the surface everything seemed fine, but by Thursday Jim could feel something wasn’t quite right at work.  People were whispering when he walked by, he noticed people staring at him and quickly glancing away.  It was one more thing for Jim to worry about, but the thing that had him worried at present were the costumes in the back seat of the car and the house they were quickly approaching. 

Jim’s thoughts turned back to the women’s club meeting.  The club’s President was Sophie Wentworth and meetings were held over other Tuesday at her palatial estate.  Sophies house had a rather large nursery for their two children, they were millionaires or at least they’d have to be to have a house as big as theirs.  Sophie, and the ladies handed over their children and then went down to their wine and gossip or whatever they did on the first Tuesday of the month.  It turned out this month they were planning a Halloween party with a special twist.

Jim looked at his charges with trepidation, there were 2 girls and 2 boys, 2 in diapers, one in pull ups, and one who couldn’t take his eyes off of a Nintendo Switch.  It turned out that Jim was a Natural with the children.  He sat on the floor and played tea party with the girls while the one in pull ups showed him every doll she owned and explained it’s life story and he changed his first diaper that wasn’t his own.  He felt a deep warmth and satisfaction from it, then a growing sadness when he realized that neither him, Pam, or Nancy would ever be able to have children of their own.  The children offered him hugs and the ladies thanked him when the meeting was over. 

“Yeah it wasn’t that bad, they were really good kids,” Jim said. 

“Great honey, I knew you’d be perfect for it,” Pam said.

“Was I just imagining it or was everyone trying not to chuckle when we left?” Jim asked.

“Oh I’m sure you’re just imagining it,” Pam said as she herself couldn’t hold back her chuckles then explained the concept for the annual ladies club Halloween party.

“You’ve got to be kidding!” Jim said from the passenger seat.  Fast forward to now, and Jim kept wanting to bite his fingernails.  They pulled into the driveway of Cindy’s house, as they approached the door Jim realized it was too late to back out now. 

Cindy greeted them as usual looking impeccably dressed in a little Rockabilly number.  Her sissy husband Sally stood behind her in skin tight pair of shortalls and tight sleeveless T-shirt.  Jim immediately felt aroused.  He knew that Sally technically was a man, or at least had been, and still hard the parts to prove it, but every part of her screamed girl.  Jim couldn’t take his eyes off her as Cindy spoke, “This party of yours sounds like a marvelous idea, it’s a shame we weren’t invited.”

Pam immediately felt like a heel, she had asked for Cindy and Sally’s help, but hadn’t thought they would want to go to the party themselves.  “Oh I’m sorry, it’s kind of for members only,” Pam lied. There would be several people at the party who were not strictly club members. 

“Oh, I’m only giving you a hard time honey, but a Disney themed Halloween party is such a great idea,” Cindy said.  It was decided that Sally and Jim would prepare in the downstairs bathroom while Pam and Cindy would get dressed upstairs.  Jim felt himself gulp at being alone with Sally. 

Sally unzipped the garment bag and felt the luxurious fabric inside. “Oh my gosh, this costume is so perfect, where did you get it?” Sally asked.

“It’s a rental, we can’t keep it, you don’t even want to know how much it costs,” Jim said realizing that his voice had softened and raised in pitch. 

“Oh Nancy I’m so jealous of this party, it sounds so amazing,” Sally said. 

“Well I’d send you in my place if I could,” Nancy laughed.

“I would so take you up on that. Why don’t you go ahead and get undressed,” Sally said.   Jim hesitated then began to take off his boring old Khaki work pants and dress shirt.  Soon he stood in front of her naked except for a diaper.  They both realized this was going to be hard.  “Well even if I can’t go I can make sure you’re the belle of the ball,” Sally said and began to pull Jim’s hair up in a headband.  After several long minutes the silence hung in the air.  “Where have you been, it’s been like 3 weeks since you were last here?”  Sally asked.

“We’ve been at home, and to be honest with you I’m not sure why we haven’t visited, I just assumed there was never a chance,” Nancy said.

“We’ve had a few little events, I’m sure that Cindy invited you and your Mommy,” Sally said. 

“I’ve really missed you,” Nancy said.  Sally bent down and kissed Nancy on the cheek, they looked at each other for what seemed like eternity then their lips locked together and they both wrapped their arms around each other’s necks.  Nancy felt passion, and she felt the stainless steel prison she wore around her clitty.  They came up for air and each shared a look of desperation.

“We better focus,” Sally said and began to apply foundation.

Upstairs things were a bit cooler, Cindy had leveraged her huge makeup collection and found just the right colors for Pam, who was doing most of the work herself.  Finally Cindy couldn’t contain herself  “OK I’ve got to ask, what happened?”

“What do you mean?” Pam replied.

“It’s been over 3 weeks since we last met in the parking lot, you said you would talk to Nancy about us,” Cindy said.

“I did actually,” Pam replied.

“Well!” Cindy said.

“Well… She seemed OK with it,” Pam answered.

“Why haven’t I heard from you then?” Cindy nearly shouted.

“I’m not sure if I’m OK with it, Nancy had an accident and over the last 3 weeks we’ve drawn closer and…” Pam trailed off.

“I see, and you just needed help tonight to get ready for your little party,” Cindy said.

“No, we could have gotten ready at home, it’s just… I really wanted to see you,” Pam said. 

Cindy staked across the room like a panther and rested her hands on Pam’s shoulders and slid a bra strap down.  She worked her hand under and popped one of Pam’s pert little boobs out and began to trace a finger around her nipple.  “Your so horny aren’t you baby,” Cindy said.

“Yes” Pam whispered.

“Aww,” Cindy said as she began to pinch and kneed the nipple.  Pam felt herself tense up and grow wet.  Her breathing became deeper, and she went to raise a hand for Cindy.  “No girl, keep your hands on the chair, don’t move a muscle.” Cindy said.  She began to work the nipple through the bra.  And Pam clinched down tight on the arm rests.  “Your panties are wet aren’t they?” Cindy asked.

“Yes,” Pam whispered. 

“Tell me what you want.” Cindy commanded.

“Take me, I want you fuck me,” Pam said.

Cindy stopped and pulled the bra strap back up over Pam’s shoulder then took a step to stand in front of her.  “One week from tonight we’ll have a date and well send Sally and Nancy out on a date.” Pam looked up at Cindy with desperation, her body was pleading for it, her brain told her it was a bad idea, her heart told her it was wrong, but her pussy said do it and her mouth said, “OK.”

“Very good, be here at six next week, now lets turn you into a Princess.” Cindy said.

It wasn’t long before Nancy and Pam were reunited, but they were no longer Nancy and Pam.  “Oh my God Sally, go get the camera,” Cindy said.  She led them out onto the front lawn as Sally rushed through the front door with a big professional camera and flash.  “Really we have to do this on the front lawn?” Jim asked.  A car nearly screeched to a halt in front of Cindy’s house while Nancy and Pam posed for pictures.  Two little girls got out of the backseat and rushed to the sidewalk.  Their young parents not far behind. 

“Anna and Elsa!” the two girls were screaming and giggling with excitement.

“I’m so sorry, but your costumes are so amazing the girls really wanted to see you up close,” the mother said.

“Aww thank you,” Pam said as she lifted up her long crystal blue gown and stepped to the girls. 

“I saw you at Disneyworld,” the girl screamed. 

The other little girl came up to Nancy and wrapped around her legs, “You’re my favorite Princess Anna, I love you!” she said. 

Jim felt his heart melt, he blushed red.  “Thank you!” he said in his best feminine voice.

“Would it be OK if we get some photos,” the mother said.  For the next 5 minutes they all posed, hugged while Mom and Dad took turns handing the camera back and forth and jumping in the photos.  The family thanked them again as they huddled back in their SUV and drove off.

“Wow, that was something,” Cindy said.

“You are so beautiful,” Sally said to Nancy.

“Only because you are so talented,” Nancy replied.  They hugged and neither one wanted to let go.

“I’ll see you next week,” Cindy said as Pam and Nancy climbed into their van. 

“What’s next week,” Nancy asked as they drove away.

“Well apparently you and Sally are going out while Cindy and I have dinner,” Pam said.

“Oh,” Nancy said.  She was already too nervous about the party to think about it. 

“I can’t do this,” she said as they walked up to Sophies mansion. 

“You can and you will!” Pam said. 

“Seriously, they’re all going to think I’m a freak,” Jim said.

“Nancy, Jim, it’s Halloween, no ones going to think you’re a freak, hell you’re fucking beautiful, quit your whining or I will pull up that dress, pull down your diaper and spank you on their front porch.” Pam said.

The ladies club had decided this year’s Halloween partie’s them was Disney Princess, with the twist that everyone had to dress as a Disney princess and that included husbands.  The men hadn’t taken it too seriously, a few had worn wigs and makeup, but that was about it.  There was a Tinker bell wit ha beard, an Ariel with a marine tattoo and mustache, and an overweight snow white about to rip her dress in half. 

Pam and Nancy turned out to be the hit of the Halloween party, their costumes were so good they didn’t look like costumes.  No one believed it was Jim under that dress, until they heard his voice.  Everyone was astounded, just as before everyone wanted a picture.  Pam and Nancy won the costume contest hands down.  With a few mixed drinks in her Nancy raised her voice and tried to talk like Anna, her mannerism became more feminine and she forgot she was nervous, she forgot she was ever Jim.   Before long she was doing Karaoke with Tinkerbell, “Let it go!” they sang as everyone cheered. 

By midnight the Disney princesses were getting pretty sloppy drunk, Cinderlla tripped on a glass slipper and fell to the floor where she fell asleep, and Ariel was on her knees in front of the toilet.  Nancy slured in Pam’s ear, “I’m soaked.”

“I warned you not to drink to much, are you leaking?” Pam asked.  She had double diapered her with super absorbent ABDL diapers, an held them up with padded foundation girdle to give Jim a more feminine shape. 

“Not yet Mommy,” Nancy said a little to loud then lowered her voice.  “It’s so swollen up that I can barely walk.”

“OK, it’s time for us to go anyway, this party’s falling apart.” They found Sophie and said their goodbyes. 

“Jim, you are the best looking princess here,” Sophie said, her words a bit slurred.   Pam was tired but wired, she’d been drinking coffee all night and avoided alcohol entirely, knowing she’d be driving home.  Beside her in the passenger seat Nancy was singing “Let it Go,” messing up about half the words.

“Did you have fun babygirl?” Pam asked.

“Yes Mommy it was the most fun I’ve ever had in my life,” Nancy said. 

“That’s good darling,” Pam said.

“Umm Pam,” Nancy said, her voice turning serious.

“Yes dear.”

“I’m transgender, I want to be a girl, I always have since I was little,” Nancy said.

“I guessed that awhile back,” Pam said.

“I want to start taking hormones,” Nancy said.

“OK, we’ll look into it,” Pam said and felt a gulp run down her throat.  She drove in silence for what seemed like an eternity until she saw a deer standing in the middle of the road frozen by her headlights.  She came a quick stop and the deer was shook out of it and dashed off.  “I know how you feel deer,” she said.

[Sarah Penguin]

yay that sounds like a fun party poor pam

[CDfm]

That was definitely an interesting admission at the end of this chapter. I guess you could kind of see it coming though. Nancy sure didn’t seem to mind being dressed like a baby girl at all. She still has to have some male left in her at the same time because she was turned on with how Sally looked so good as a girl. I will be waiting for the next new chapter. 

[SissyBabyWannaBe]

 so are we getting any more to this story. thought you were doing a really good job with it so far

[Sarah_Hillcrest]

On 7/17/2019 at 5:32 PM, SissyBabyWannaBe said:

 so are we getting any more to this story. thought you were doing a really good job with it so far

As of now I can't say when I will write more.  I haven't been interested in diapers in almost 2 months, but it makes me really happy that at least one person is asking about it.  I put so much work into writing as much as I did and I had big plans for Jim/Nancy and Pam.  I'm sure I'll come back to it one day.  

[Tld17]

We all loved it.

[Sarah_Hillcrest]

Finally felt some inspiration and had time to write.  Hope you enjoy!

 

Training Her Baby Part 33

The Date

 

Pam sat beside her husband, baby, daughter, wife, Jim who she was trying to remember to only call Nancy, while a doctor explained the many effects and dangers of Gender Affirming Hormone Therapy.  What had started as a harmless bit of sexual roleplay had become a lifestyle, and now it was becoming her life.  Words like Spironolactone, Estradiol, Progestin, were floating through her mind but she couldn’t focus on what the doctor said. 

“You didn’t say much, are you sure you are OK with this,” Nancy said while Pam navigated the freeway home.

“Umm, what?” Pam said.

“Are you OK with this?”  Nancy asked.

“Does it matter?” Pam said.

“Yes it matters, this is a decision I can’t make without you,” Nancy said.  Pam didn’t reply she began to think about the last several months.  Discovering her husband was an adult baby and a sissy, discovering that she found herself sexually attracted to women, then the admission that she had been expecting, her husband was going to become her wife. 

“Maybe we were meant for each other,” Pam said as she tried unsuccessfully to fight back tears. 

Nancy began to bawl, “We were, I know we were put together for a reason.”  Pam pulled Nancy up against her and wiped her eyes, she had to focus on driving while her partner bawled into her sleeve.

 

 

 “I won’t do it!” Sally yelled.

“You will do it,” the mistress said as she turned and gave Sally an icy glare.  Sally realized she had no power here, she could pout and fight all she wanted but she knew that she would submit to Cindy, she always had.  

“Why do we have to do this,” Sally pouted.

“Because I say so and because she needs it.  You know as well as anyone, what sissy training is like.”  Cindy replied.

“Yes, mistress,” Sally pouted and turned her back towards her wife, mistress and mommy.

Cindy grabbed her and whipped her around, “You will wipe that pout off your face girl or I will slap it off, make sure that Nancy is having the time of her life tonight.”

“Yes mistress,” Sally said.

An hour later Pam and Nancy arrived at Cindy’s for the long-awaited date.  Cindy and Sally both did a double take when they saw Pam and a conservatively dressed woman behind her.  “Nancy?” Sally asked.

“Yes it’s me,” Nancy said in her best female voice.  Cindy couldn’t hide her grin as she led everyone to seats in the parlor.

“So Nancy has decided to transition,” Pam announced.

“I’m still going to work as Jim, but I’m living as Nancy as much as possible,” she explained.

“I’m so proud of you,” Sally exclaimed.

“So what’s up with your wardrobe, you going to church?” Cindy asked.  Nancy was dressed in a below the knee skirt, tan panty hose, long sleeve black blouse, and was carrying a plain crossbody purse.  Her makeup was light and natural and her wig was pulled back in a tight clasp.  In contrast Sally was dressed to go clubbing in a black bodycon dress and her makeup was anything but conservative. 

Nancy looked down at herself and seemed a bit flustered, “I thought it looked nice.”

“Yes darling, you look very nice,” Cindy said with a laugh, “You also look like a librarian.  Sally take her down and help her get ready.”  Sally took Nancy by the hand and bounced down the stairs with her.

“You know you don’t have to be so rude,” Pam said once the Sissies were gone. 

“Oh really,” Cindy said and sauntered over to Pam.  She placed her hands on the woman’s shoulders and slid them down her chest slowly.  Pam shuddered when Cindy delicately caressed her nipples.  “Have you been thinking about me?” Cindy asked as she took hold of Pam tightly.

“Yes,” Pam said and bit her lip. 

“That’s good,” “We have reservations at Nico’s, I’ll be right back,” Cindy said and released her then walked down stairs.  Pam realized she was shaking just at Cindy’s touch, she also realized she was dripping.

Downstairs Nancy was stripped down to her diaper and stuffed bra.  “We’re leaving, your car will arrive in about an hour so don’t dilly dally,” Cindy said as she walked over to Nancy and grabbed the front of her thick diaper and could barely feel the steel chastity device through it.  “Do you have two boosters in there?”

“Yes mam,” Nancy answered.

“Good girl, it may be awhile before you can be changed.  You two have fun tonight,” Cindy said and left.

“We’re so lucky that we wear the same size,” Sally said and opened a closet.  First thing first girl, we got to shape that body,” Sally removed the stuffed bra and attached some adhesive clasps to Nancy’s chest and connected them together.  Once the bra was back it looked like she had cleavage, next she began dressing her in an ultrafirm shapewear body suit.

“Umm Sally am I suppose to be able to breath?”

“No babe, but it’s worth it,” Sally said as she wedged silicone hip pads into the garment.

“Will I always need this stuff?” Nancy asked.

“Well depends how your body reacts to hormones, I don’t need any padding now, but it took years,” Nancy answered.  “I still need the tight shapewear though to keep diapers quiet and smoothed out when I dress in something a little tight like this.”

Sally returned to the closet to pick out a dress, “I’m so glad you’ve shaved everything, so many more cute options,” she said back.   

“Actually, Pam and I waxed, mostly me, oh my God I’ll never do that again,” Nancy said.

“No one said being a girl would be easy,” Sally said as she tugged a black bodycon dress over Nancy similar to hers.  It was several inches above the knee and closed with a halter neck and choker.  Sally zipped her up, replaced her wig and directed her to the mirror.

“Oh my God,” Nancy said.  She was drop dead sexy and looking every bit a woman.  The shapewear, padding, and diaper were doing their job and Nancy appeared to have generous hips and a small waist.

“Damn girl, you look good.  You’re really lucky your face is so naturally feminine, now lets just tone up that makeup,” Sally said.

 

***

By ten O’clock Nancy and Sally were sitting a small table in a neon lit dance club that was known to be friendly to LGBTQ people.  They had both been dancing and Nancy was a bit flustered and light headed from the drinks that guys had been bringing them.  Nancy wet herself a little but was pleased that she didn’t even feel wet, and even more please she didn’t have to wait in line for the bathroom. 

“Do you always get hit on so much?” Nancy asked over the thumping music.

“Well when you go to a place like this that’s kind of expected,” Sally answered.

“Do they know?” Nancy asked.

“Know what?” Sally asked.

“You know, about us,” Nancy replied.

“Yeah, probably, most of them do, there are tons of guys who are really into transgirls.  They’re called chasers.” Sally said.  Nancy watched two hot women on the dance floor grinding against each other, then scanned the room, were guys dancing with guys and mixed couples, it didn’t seem to matter.

While Nancy was studying the dance floor Sally took her phone out of her tiny purse and checked her messages then frowned.  “Hey girl, lets get out of this noise for a minute,” Sally said and took Nancy by the hand and lead her across the club to a hallway. 

“Where are we going?” Nancy asked.

“This club has some chillout rooms,” Sally answered.  They entered a room together, it was small and dark, lit with blue decorative lights; there was also a couch and chair.  A small speaker played light trance music.  Sally seemed nervous and Nancy began to suspect something was up, “What’s going on?” she asked.

“OK listen, I just want you know that this isn’t my idea,” Sally said.

“What isn’t your idea?” Nancy replied.  Before she could answer the door opened and Sally slipped out and a man slipped in and shut the door.

“Hey girl, I hear you like to party,” said a voice that she was very familiar with.  The lights switched on and Nancy saw her old boss Doug looking down at her like a wolf. 

[Sarah Penguin]

[ppbenn]

Oh my! A wonderful addition.  I hope to read more soon. Thank you for continuing this excellent story. 

[Sarah_Hillcrest]

This is the first chapter I've wrote in awhile that's overly sexual, hope you enjoy.  While Nancy is facing down his X-boss while crossdressed and diapered at a nightclub her wife is about to find herself in a predicament as well.  

 

Training Her Baby Part 34

Pam’s Date

 

“Do they know?”  Pam asked.

“Know what?” Cindy said.

“You know, about us,” Pam said.

“Yeah, two woman enjoying a romantic dinner at a fine restaurant, yeah I’d say they know, no one gives a shit,” Cindy said.

Pam scanned the room discreetly, Nico’s was a fine restaurant, their supper and drinks would probably cost more than some people made in a weeks’ wages.  Pam received nothing but looks of support and encouragement from the other patrons and they weren’t the only same sex couple in the room.  These are liberal progressive rich people, hell they not only don’t give a shit, but they actually like that we’re two women on a date, Pam thought. 

They shared excellent conversation and excellent food, Cindy told stories discreetly about some of her clients, and Pam talked about her life, and her family ambitions that were sidelined by infertility.  “Jim didn’t want to get treatment, didn’t want to adopt, just pretended everything was going to work out,” Pam explained and felt a tear in her eye.

Cindy took her hand, “Listen honey, imagine how hard this would all be if you and Jim had kids, because trust me, nothing would change.”

“Well, I would know what it’s like to really have that bond with someone, to really be a mother,” Pam said.

“Oh you know what’s like and more,” Cindy said pausing for dramatic effect she looked Pam in the eye.  Nancy is the luckiest woman in the world to be your wife, and you’re the luckiest woman in this room tonight, or at least your going to get lucky tonight.” When the waiter came Cindy ordered for Pam, which she thought was a bit overbearing, but also kind of sexy.  When it came time to pay Cindy took the check, and when it came time to leave, she helped Pam put on her coat.  There was no doubt in Pam’s mind who was in charge here.

They shared a glass of chardonnay back in Cindy’s kitchen and Pam realized that Cindy was looking at her with lustful eyes.  Cindy sat her glass down and stood behind Pam.  She ran her fingers down Pam’s shoulders and across her nipples and she felt her breath tighten in anticipation.  Pam was spun around in her chair and Cindy enveloped her lips in a deep lustful kiss.

At some point Pam found herself in Cindy’s bedroom nude while Cindy was still in her evening wear.  Cindy began doing things to her pussy that were driving her to moan incoherently.  “Yes darling, just let it out, just let it out,” Cindy continued to say.  Pam felt a growing pressure, like she needed to pee.  She wanted to tell Pam to stop but it was so good she just ignored it, then like an electric wire Cindy placed a vibrator against her clit. Pam felt a slight release from the pressure and a wetness on her leg, in her state she was unable to understand what had just happened to her.

“Oh, you naughty girl you just wet all over the bed,” Cindy said. 

“I.. what,” Pam said.

“You squirted honey, all over me and the bed,” Cindy said seeming just mildly annoyed.

“Oh my gosh I’m so sorry,” Pam replied.

“Oh baby, it’s really OK, you can’t help it, some girls can’t control themselves when they are being touched the right way,” Cindy said.  Pam noted that her tone of voice had changed, she was now speaking to Pam less like an adult and more like a child. 

Cindy reached into her nightstand and Pam heard the unmistakable crinkle of a diaper, she recognized the pink princess ABDL pattern immediately. 

“Umm, what?” Pam asked.

“Lift up your legs baby,” Cindy said as she unfolded the diaper and laid it on the bed in front of Pam.

“Now, wait that’s Nancy’s thing, I’m not really into it,” Pam said.

“Well dear, I’m not into having wet sheets, but if you’re not interested, we’ll just call it a night,” Cindy said.

“No, wait, are you saying the only way we’ll have sex is if I’m diapered?”  Pam asked.  Cindy nodded with a smile.

“It makes you really happy doesn’t it?” Pam asked.

“What’s that dear?” Cindy asked.

“Taking people’s control, making them feel helpless,” Pam said.

“Do I make you feel helpless?” Cindy asked.  Pam nodded and raised up her legs.  Cindy smiled and slid the diaper under her bottom and said, “Now that’s a good girl, lets get you all diapered up.”  Pam felt her cheeks turn red with humiliation, she couldn’t believe this was happening, but at the same time she couldn’t help it. “Now little one, if at any time you decide you want to stop your safeword is cactus, do you understand,”  Pam nodded.  “OK baby I want you to roll a round a bit for me,” Cindy said.  Pam rolled around on the bed and felt more shame listening to the crinkle of the plastic backed diaper. Cindy directed her to lift her bottom up in the air and gave her a spanking for wetting the bed.

30 minutes later Pam was sweating and moaning, Cindy was such an expert, multiple times she had brought her close to orgasm only to stop and leave her wanting more.  She had then used Pam’s mouth for her own orgasm.  Pam was beginning to feel more and more frustrated and upset.  “Please I want to come,” she begged.

“You know babies don’t really talk,” Cindy said and pulled a pacifier gag out of her nightstand.  “Now I’d like to play with you more but I need your permission first baby.” Cindy said.

“Yes, please just make me come,” Pam said.

“OK, very well, now once I put this on you it will be hard for you to say your safeword,” Cindy said.

“Please, just whatever,” Pam said.

“OK I want you to say, Mommy I’m your babydoll to play with,” Cindy said.

“Mommy I’m your babydoll to play with,” Pam quickly replied.  Pam was directed to stand and placed in the gag and some pink wrist cuffs that were secured behind her back.  Cindy held her carefully and took her downstairs to the nursery, then into the small room to the side, the one with her more serious toys.  The room was most black and stored various pieces of furniture that Pam instinctively knew were for sex.  Ropes, chains, and all manner of toys hung from a peg board on one wall.

Cindy locked Pam’s wrist to the top of a large X shaped cross then strapped her waist to the back of it and finally her legs.  Pam was immobilized, she began to think that maybe she had made a mistake, maybe all of this was a mistake, then Pam began buzzing the front of the diaper with a magic wand and all other thoughts were gone. 

A few minutes later Pam was breathing heavily and found herself suckling the pacifier gag wishing for release.  Cindy took Pam’s chin and raised to towards her“Now babygirl, I’m going to do something to help you more enjoy your diapers, would you like that?”Pam mumbled yes into her gag which was removed.  Cindy replaced it with a similar gag but with a larger nipple that filled Pam’s mouth.   Cindy moved outside of Pam’s view and she heard the sounds of things being moved around.  A short time later a device that looked much like a large enema bag stand was wheeled in front of her.  A bag of green liquid was hung and from the stand and Cindy attached the hose to the new pacifier gag.  She then placed part of the hose with a switch in Pam’s secured hand above her head.  Next Pam locked the magic wand in another stand and placed it directly underneath her and switched it on.  Pam realized it was just a fraction of an inch under her diaper. 

“Now babydoll, you are in a predicament, you want to come but you can’t quite reach the magic wand,” Pam said as she began to peel the replaceable tapes off the diaper and pulled it up very tight and snuggly refastened it.  “This is a bag full of diet mountain dew, it will make you wet your diaper, and these ABDL diapers will expand when wet and push down against the magic wand, and you’ll get the wonderful release you’ve been waiting for.  All you have to do is push that switch in your hand and start drinking, but once you start you can’t stop.”

Pam’s eyes were bugged out, the idea of wetting herself was so humiliating but she was being driven crazy with desire.  It only took her a moment to push the switch and feel the sticky sweet liquid start flowing into the pacifier gag.  Cindy giggled and sat down on a bench to watch her helpless slave suckle down the soda and make sure she didn’t choke.  Before it was through soda was dribbling out from under the gag, and Pam was struggling to drink it down, but Cindy only watched knowing that her baby was OK.

“Good job baby, I’ll be back in awhile, I hope you enjoy the ride, oh and this camera is catching everything,” Cindy said as she pointed out a camcorder on a tripod.  Cindy left the room and Pam felt her swollen stomach and belched.  She could already feel pressure building up in her bladder, then the sudden thought hit her, once she soaked her diaper if it did swell up and begin rubbing the wand there would be no one to turn it off.

 

[ppbenn]

Wow! An amazing chapter. Thanks for writing this story. 

[Sarah Penguin]

[kirababy]

very interesting return, and turn of events.  Looking forward to finding out more about this visit, the video, and what Cindy is doing while Pam is "suffering"

[Diaperingdaddy]

That's a great update! 

[Sarah_Hillcrest]

Thank you for all the comments.  The following chapter picks up where 33 left off, and I'm going to make the assertion that if someone was very highly "made up" then they wouldn't be recognizable even by someone who knows them well.  I apologize that this chapter doesn't really mention diapers at all but is far more concerned with gender roles and the darker side of a humiliation fetish.  It is of course wildly unrealistic fiction.

 

Training Her Baby Part 35

Nancy’s Lesson

 

Nancy felt a shot of adrenaline through her body, she had never been this shocked before in her life.  The date with Sally had been going so well, she was on cloud nine, then suddenly everything changed.  Was this some kind of setup, why had Sally left her with her ex-boss Doug?  She wanted to try and bolt around Doug, he noticed her glance at the door.  “Relax doll, this is all part of your training,” he said calmly.  Nancy looked at Doug in the eye and realized he didn’t recognize her, she quickly looked to the floor.

“Aww I can see you’re a shy one, why don’t you take a seat there,”  Doug said.  Nancy glanced at the couch and sat down smoothing hour her short dress.    “Tell me your name,” Doug commanded.

“Nancy,” she said as soft and high as she dared.

Doug smiled, “OK Nancy, I know you are a sissy, I know your mistress keeps you locked in chastity and diapers.  I help your mistress with training sissies in their most important function.  Do you know what that is?”  he asked.

“No,” Nancy said as meekly as possible.

“Whenever you address me you will call me Sir, do you understand,” Doug added.

“Yes Sir,” Nancy said.  She always knew Doug was an asshole, but this whole dom thing was so over the top, she wanted to ask him what life was like on unemployment after losing his job in a stupid scam, but still thought it best to keep quiet.

“Good girl, the most important function for a sissy is to please, and right now it would please me if you would suck cock,” Doug said.  Nancy felt a bead of sweat on her forehead, there was absolutely no way she was going anywhere near Doug’s cock, no matter how big it was.  Wait, did I just think that, Nancy thought.   

“Now just let it go and relax,” Doug said and began to pull his shirt over his head.  Nancy instantly recognized the words from Cindy’s hypnosis CDs, it wasn’t like she became a mindless slave, but those words seemed to open up her mind a bit and she glanced up at Doug, I’d never realized how toned he is, she though.   She examined the tightly groomed chest hair and the way the light played on his muscles.  Doug turned around and locked the door then turned back around with a smile on his face.  “I only do this for Cindy because her sissies are always hot, do you realize that Nancy, how hot you are?” Doug asked.

“No Sir,” Nancy said and began to feel her chest rise and fall, she felt her clitty press against her cage.

“It’s hard to believe you were ever a man, but truth is you never really were, you were just a sissy waiting for the right person to turn you into what you were meant to be, do you know what you were meant to be?” Doug asked.

“No Sir,” Nancy said breathlessly.

“A pretty little cocksucker,” Doug said as he unbuttoned his pants.  He zipped them down and pulled them to his knees, then his boxers went down and his manhood sprang out ready for action.  This cock was nothing like the clitties that she and Sally possessed, it was easily twice as big.    Nancy felt her mouth water.  “On your knees slut,” Doug commanded.  Nancy was familiar with the command having heard it in her sleep many times.  Without a second thought she was off the couch and on her knees in front of Doug.  “Very good girl, the only thing a sissy craves is cock, you want it, nothing pleases you more than pleasing someone else,” Doug said. 

She had imagined herself in this very situation so many times, she had wondered what it would be like to give a blow job back when she was Jim, but forced by the hypnosis CD  she had imagined it in great detail, dreamed about it, and now she was living it.  It only took a couple seconds for Nancy to realize she didn’t have a choice.  She crawled forward until his rod was inches from her lips then took it in her mouth. 

“Good girl, use lots of spit,” Doug commanded.  Nancy slid up and down the shaft relishing the feel in her mouth the smell, the feel of Doug’s pubic hair.  Doug let her explore for a several minutes but then he placed his hands on the back of her head pushing it in a little further with every stroke, soon it was banging the back of her throat and she was fighting a gag reflex.  “Use your tongue, push up against that cock,” Doug commanded.  Nancy could feel his breathing getting faster, and the fact that she was getting him off only made her more excited.  “OK, slow down, not so fast,” Doug said and pulled his cock out of Nancy’s mouth.  “Now get your hands in there, stroke the shaft, slow and steady,” Doug said.  After a few moments Nancy could tell he was starting to feel it, he was going to come.  His glans were swollen now.  Instinctually she slowed down even more, keeping him on edge.

“Oh yeah, you’re a natural, now get that cock in your mouth,” Doug said as he force plunged it back between her lips.  Nancy had salvia running down her chin and relished each moment as the cock slid in and out, in and out.  She felt something slightly salty in her mouth and knew it was precum.  Doug was breathing hard and his whole body was tensing up.  Nancy grabbed around his tight ass cheeks and felt a gusher of cum in her mouth.  Doug pulled out and yelled, “stroke it, stroke it,” Nancy began to furiously stroke as another gusher of cum splashed across face, then another smaller one.  She latched back on and sucked the last drop out.

Doug reached down and pulled his phone out of his pocket, Nancy watched in a daze as he posed his still hard cock near her lips.  “Open your mouth,” he commanded. Nancy was like automation, she opened up revealing a mouth full of cum.  He took a photo of her cum covered face.  She knew she had just been violated but was too caught up to say anything.  “Damn girl,” Doug said as he put the phone back in his pocket and pulled up his pants, “You can suck a cock.”

“Thank you sir,” Nancy said without thinking.  What the fuck is wrong with me, that asshole just took my picture, Nancy thought, but remained silent.

“Don’t worry about the picture, that’s just for your mistress, I’ll let her know how good you did.  Maybe we’ll meet again,” Doug said as slid his shirt back on. He turned to unlock the door and stepped back out into the thumping music in the hallway.  Nancy collapsed in a pile on the floor, she stared up blankly at the blue light bulb in the ceiling and felt the sticky warm liquid flow off her face.   Sally came in, shut and locked the door then settled down beside her with a package of Kleenex.  Nancy took one and spit the cum out of her mouth, then looked up at her and couldn’t hide the anger from her face.  “You set me up.”

“I’m so sorry, I swear I didn’t want to,” Sally said as she felt a tear began to fall and began wiping Nancy’s face.  Nancy couldn’t hold the anger and began to sob.  Sally explained it was part of sissy training, that she’d been through it too.

“You want to know what’s really fucked up, I liked it,” Nancy sobbed.

“I know honey, I know,” Sally said as she wiped away tears from Nancy’s face. 

“What’s wrong with me?”  Nancy said trying to get ahold of her sobbing.

“Nothing, their is nothing wrong with you, your perfect,” Sally said and began to cry.   

[kirababy]

interesting - and lucky she was not 'made', i'm sure.

[SissyBabyWannaBe]

will there be any more?

[sissibaby]

I think it would be a good idea before you post a story to read it out loud and make corrections.  You constantly confuse Pan and Nancy and even Sally and Cindy.  You also make a ton of errors in spelling as well as with words.  The writing is excellent but it is important to be sure you are posting something that has been edited.  Spell checks work well and reading out loud to yourself helps to make sure you have names correct when they are speaking.  Keep up the good work, you will only get better and better at the art of writing.

[BB888]

God I hope you continue!!!

This is, BY FAR, one of the best stories ive read in years!!!

 

Don't pay attention to others who can't look past a few stupid typos... Your story is AMAZING!!

 

PLEASE PLEASE CONTINUE IT!!!!!