After what happened at work today, Jill can hardly wait to get home to tell Allie. As she changes into her girl clothes, she can't resist sitting in front of the mirror to brush her hair and admire herself. She loves the way Jorge styled her hair, and she feels extra feminine tonight. She feels so feminine that when puts on her bra, she decides to stuff cotton in the cups before putting on her dress. She likes pretending she has real tits.
Joining Allie on the couch, she lies down with her head in Allie's lap. Allie lights a joint and holds it in front of Jill's lips so she can effortlessly take the relaxing smoke into her lungs.
"I see you stuffed your bra," Allie remarks. "You must be feeling your woman tonight."
"I do, Allie. I feel more comfortable being a girl with my new hair. It really feels like I'm home. And what Rosy did for me today was so sweet. I wish you could have seen her."
"Yeah, I was going to ask you how work went when you showed up with your new hair."
"Well, the guys really gave me a hard time when I punched in. But when Troy started calling me a sissy, I didn't feel ashamed. I actually felt proud to be a sissy because I know that's what I truly am. They made fun of me all morning until Rosy showed up. She looked so hot when she brought me my lunch. She wasn't wearing a bra and she wore tight jeans that hugged her ass like a tight glove.
"She wiggled her ass and made sure the guys saw her tits bouncing when she came back to where I was working. She even kissed me while the guys were watching, and when I was walking her to the door, she put her hand on my butt so all the guys could see it. They never said another word about my hair the rest of the day. Rosy really saved my ass."
"I told you, Jill. Rosy likes you a lot. I think she wants to go to bed with you."
"Yeah, she made it pretty clear she wants it. I can't believe I'm going to actually get to fuck a real girl."
"It's a great thing to thing to look forward to. We're really good together, Jill. Our lives have been magic since we've been together."
"Yeah, I know... that's what I meant when I said I feel like I'm finally home."
~~~~~~~~~~~~~~~~~~~~~~~~~
The next day the guys at work still tease her a little bit. But they aren't teasing about her hair, they tease her about Rosy. They tease her by asking if Rosy has a tight pussy, or how many times did Jerry fuck her last night. They call her names like 'lover boy', and 'cock hound'. Jill just smiles and chuckles to herself, thinking, 'If they only knew.'
It's Tuesday, and she has a date scheduled, so she rushes home from work to take a quick shower and get ready. She's kinda tired tonight and would rather not go, but she's a part-time whore now, and she made the date last week. She has to deliver the product she is selling, so she honors her commitment and meets Dr. Walt at the same place they met last week.
Walt is waiting for her in the lobby as she walks in with Allie's overnight bag over her shoulder. "Hi Jill!" Walt greets her, "Wow! You got your hair styled. What a difference!"
"Yeah... Allie took me to the stylist Saturday, do you like it?"
"Like it? I love it! It really brings out the feminine features in your face."
Since there are three other people in the elevator with them, no words are exchanged as they ride up to their floor. As soon as they get in the room, Walt gives her a hug and says, "I really enjoyed our time together last week, Jill. I've relived our time in the shower several times this week."
"Mmmm... yes. That was fun, wasn't it? I had such a good time with you last week, too. I've been really looking forward to tonight," Jill says, but she's lying. Truth be told, she'd rather not be here at all. She wants to be a good little whore, so she tries to tell Walt what he wants to hear.
Since this is their second date, Walt is more relaxed being with Jill this time. She's more relaxed herself as they chat and look at the dinner menu. After making their choices, Walt goes down to order the food like last time and Jill goes into the bathroom to change.
Allie packed her bag again, and this time she gave her pink panties and matching bra, along with one of her three-quarter length red slips, instead of a plain dress. 'Hmmm...' she thinks, 'This is a bit more sexy than last time.' She also finds a stick of lipstick, some pink rouge, and a bottle of perfume along with a note:
I think it's about time you start making up that pretty little face of yours to go along with your new girl hairstyle. You know how to do it, baby. Have fun... you pretty little whore.
Jill smiles as she reads the note. 'Allie's always teaching me,' she thinks to herself. Remembering what Carla showed her last week, she carefully applies the makeup, being careful not to put on too much. She's rather proud of herself when she looks in the mirror and sees a pretty girl with pink lips and rosy cheeks smiling back at her.
She's so glad Jerry's shaggy, uncut hair is no longer a part of her. After adding a couple dabs of perfume here and there, she looks and feels like a sexy little whore. She gets a little giddy, knowing she's taken another step on her path towards feminization.
Since she's spent more time getting dressed than last week, Walt is waiting for her when she comes out of the bathroom. "Well, don't you look pretty," he tells her. When he gets a whiff of the perfume, he hugs her tight and kisses her. Walt's not as shy about coming on to Jill as he was on their first date.
While they wait for room service to bring their dinner, Walt takes her to the couch and has Jill sit on his lap. She's liking this different side of Walt, a side of himself he was too shy to reveal last week. Sitting on his lap, she feels like she's his baby girl, and it's actually turning her on.
She puts her arms around his neck and let's him kiss her all he wants. By the time dinner arrives, he's worked his hand inside her panties and given her a hard-on.
They didn't talk much while they were making out before dinner; but as they eat, they engage in the pleasant conversation they both enjoyed last time. "I brought you a book you might like to read," Walt says.
"Oh, that's so sweet of you, Walt. What's it about?"
"Well, remember how you were telling me about how you grew up poor and now you're looking for opportunities instead dwelling on the past? This book might help you. It was written by one of my favorite authors, Neville Goddard, it's called 'At Your Command'. It's a short book, but it has a powerful message. You'll probably have to read it a couple times to really understand it."
"Aww, thanks, Walt," Jill says, "You didn't have to do that."
"I know I didn't have to, but I wanted to. I really like you, Jill. I want to see you and Allie succeed. I'm so impressed with how you look with your hair styled that way. You look more feminine every time I see you."
"Yeah, I really like my hair this way. It's like I just got rid of another part of my male body."
"Speaking of your body," Walt starts to say, "remember when we talked about the hormones last week? Well, I wrote a letter to my friend Maggie, in Chicago. I told her about you and Allie, and asked her if she had any information she could share with you. If she writes back, I'll pass it on to you."
"Wow, thanks, Walt. I hope she writes you back. I told Allie what you were telling me last week. We'd both like to find out more about it, for sure."
After they finish dinner, Walt takes her back to the couch and resumes where they left off. Jill was hoping to talk a little more about hormones, but she's mindful of the fact that she's Walt's date. More specifically, she's his whore. This is his time, not hers, and he's more interested sex tonight, not conversation.
As he plays with her cock, she unzips his pants and reaches inside. She's pleasantly surprised to feel him halfway hard when she grabs him. Before she gets on the floor to suck his cock, she stands in front of him and gives him a little show, wiggling her ass as she takes off her slip.
Standing in front of him in her in her pretty pink lingerie, Walt smiles and reaches for her cock. She lets him play with her a while before she undresses him and sucks his cock. Unlike last time, Jill easily gets him hard and takes him over to the bed. She's enjoying this different side of Walt as they get in the sixty-nine position and suck each other's cock.
They spend an hour or so on the bed enjoying care-free fellatio with each other and Walt really gets into Jill's hard cock. Jill feels a feminine side of him wanting to express itself as he kisses and sucks on her. Sometimes she lays on her back as he sucks her. Other times, he is on his back as Jill sucks him.
Several times, Jill straddles his face and offers her ass to him, but he isn't interested. He just wants to suck her cock, and never even touches her pussy.
When they get back in the sixty-nine position, Jill thinks it's about time to end this date. Remembering how she got him off last week, she starts playing with his ass and sucks him harder. She can tell how much he's getting turned on to the ass-play by the way he's sucking her on the other end.
She lightly caresses a wet finger around his asshole, sucking him harder until his cock can take no more. As Walt fills her mouth with cum, she starts fucking his mouth, wanting to get herself off so she can go home. Walt grabs her ass as he feels a wave of femininity sweeping over him.
Jill closes her eyes and imagines Rosy sucking her cock. It doesn't take her long to release her load with Rosy on her mind, and Walt eagerly swallows every drop of her cum. Lying on the bed together, Walt tells her this is the most turned on he's been in a long time.
As they talk, he opens up and tells her about a close relationship he had with one of the guys in the Club. They had gotten together every week for years to enjoy fellatio, but he passed away a year ago and Walt has been secretly grieving him ever since. Jill is touched that he trusts her enough to share this with her.
She feels closer to Walt as they walk into the bathroom to clean up. She cleans his cock and balls for him before he gets dressed, and when he gets ready to leave, he asks Jill, "I'd like to make another date for next week, but would you mind if I'd like to see Allie instead of you?"
"No, Walt, of course not. I think Allie would love to see you. Let's make it a date, and if Allie can't make it, I will. But I'm sure Allie will be available."
"Thanks, Jill. I'm really attracted to both of you. You each have different qualities that compliment each other so well."
Jill replies, "Well maybe some night you might like to have both of us pleasuring you at the same time?"
"Now that's a suggestion that gives me naughty thoughts," Walt chuckles.
"Give it some thought," Jill says, as they walk towards the door.
When Walt leaves, she goes into the bathroom to change back to a boy. She notices an envelope in the back pocket of Jerry's pants before she puts them on. Walt put her tip there when she wasn't looking. She opens it up and finds two $100 bills.
'Hmmm... A bigger tip than last time,' she thinks, 'I must be a good little whore'.
Once she's dressed, she starts to wash off the makeup, but likes the way her face looks, so she leaves it on. She's pretty sure she can get through the hotel lobby without anyone noticing her if she walks fast.
~~~~~~~~~~~~~~~~~~~~~~~
Allie greets her at the door when she gets home. "Hi babe," Allie says after they kiss, "How was your date?"
"It was way better sex than last week. I didn't feel like being there at first, but when I got dressed and put on the makeup you gave me, I felt like a sexy little whore again. We actually had a good time sucking each other off. He didn't have any problem getting hard this week either. And when we got done, Walt made another date for next week.
"Oh... he gave me this book, too. He's really a nice man. There were times tonight when I felt like he was the father I never had. He had me sitting on his lap and I felt like his little girl."
"He must really like you if he wants to see you again."
"Well, actually... he wants to see you next week, Allie. I told him you'd probably be available to see him. But if you don't, I'll go instead."
"Of course I'll see him, Jill. We're their whores now, this is what we do." Allie says as she laughs. "Go get your nightgown on, I have to tell you what happened while you were gone."
Allie rolls a joint while Jill hurries to changes into her nightgown. Joining her on the couch, she's anxious to hear what happened while she was on her date.
"You're gonna love this," Allie begins, "Roger came over to bring your refund check for the deposit on your apartment."
"Oh yeah?... I suppose he wanted sex, too?"
"Yup... and I fucked him real good, too. Cuz I wanted something from him."
Jill's curiosity is aroused. "What did you want from him?"
"Well... You remember when Carla said the only way to really make this apartment feel like it's our home is to paint the walls and start from scratch?"
"Yeah, I remember."
"Well... when he was here, he started coming on to me like he always does. And I thought, 'I wonder if I can play slutty and bribe his horny ass into painting this place for us?' He didn't want to at first.
"But when I started sucking his cock, he got more receptive to it. And when I had his cock up my ass, I asked him again in a slutty little girlie-type voice. He had no choice but to say, 'Sure, I'll send my painters over next week.'"
Jill giggles as Allie tells her that. "Oooo... What a clever little bitch you are," she says.
"Yeah... I was rather proud of myself, the way I used my pussy. I fucking had him wrapped around my little finger, Jill. I used my pussy to get what I wanted. And why not? All the times he's fucked us for free? I figured he owes us something for that."
Jill laughs her ass off, "Oh Allie... You're such a little whore. This is too much fun, playing the game as girls. Walt gave me $200 tonight, and Roger's going to paint our apartment, for free! It's amazing what men will do for sex. Being whores certainly has advantages."
Allie agrees, and they spend the rest of the night watching TV and smoking joints. For the second night in a row, they do not have sex when they go to bed. They're learning the joys of just holding each other as they tenderly kiss each other in bed. Feeling the bond of love growing inside gives them all the pleasure they need.
~~~~~~~~~~~~~~~~~~~~~~~~~
Jill is super excited when her day starts on Wednesday. Tonight she's taking Rosy out to dinner, and then they'll go shopping for Jill's first outfit to wear at Ladies' Night this Saturday. The anticipation has been killing her all day.
Rosy's been excited about it all day, too. She's been thinking about Jill all week. After Carla gave her permission to go to bed with Jill, she gets wet just thinking about her. She knows she has to be patient. Carla made sure she understood about taking precautions to prevent an unwanted pregnancy. But still, just thinking about Jill gets her juices flowing.
She greets Jill with a hug and a kiss when she arrives. Carla is at the Melody working, and Rosy's been pacing the floor, waiting for that doorbell to ring. After a few kisses, Jill walks her to the car and opens the door for her as she gets in.
On the way to dinner, Rosy asks Jill about what kind of outfit she wants to get. Jill tells her she wants something really sexy. She wants to go full whore Saturday night, and Rosy tells her she knows just the place to go.
They enjoy a delightful dinner together, happily talking and giggling like the girls they are. They are more attracted to each other when they leave, having learned more about each other as they talked over dinner.
Rosy directs Jill to a medium-sized strip mall, and she pulls into a parking space in front of a store called, 'Naughty Lady'. Walking hand-in-hand with Rosy into the store, Jill gets nervous.
"You seem nervous... Are you?" Rosy asks.
"Yeah... I'm kinda scared all of a sudden."
"Try to relax. There isn't even anyone in here. It's good we're here on a week night."
"Yeah... But this is still scary. I feel like running away."
"Well, don't worry. I'll take care of you."
As they look at some of the dresses on display, Jill freezes when she hears a woman's voice behind her. "Can I help you find something?" the sales lady asks.
Jill turns around to see a woman in her late forties offering to help them. She is petrified, not knowing what to say. Luckily, Rosy steps in to speak for her.
"Yes, we could use some help. This is might sound a little weird, but we're looking to buy the sexiest outfit we can... for my husband."
When Jill hears those words coming out of Rosy's mouth, she totally freaks out, squeezing Rosy's hand as if to say, 'Fuck! Why did you have to say that?'
Jill doesn't say anything, of course. She's frozen, unable to move or speak. Rosy smiles and says, "Relax, baby. You said you'd do this for me."
Jill thinks to herself, 'What the fuck is she saying? She's making me look like a fucking fool!'
Rosy begins to speak to the sales lady, who is a bit confused at this point.
"OK, let me explain why we're here. You see, some of my parents' rich friends live in the Riverdale district, and they host this fundraiser for charity every year. They call it the 'Reversal Ball". What it is, the men go dressed as women and the women go dressed as men.
"Now, the highlight of the evening is when the men have to take off the dresses and display themselves in lingerie, while the women vote with $50 bills for the sexist man. I want him to win. He wouldn't go last year, but he promised he'd go with me this year."