Ginger and Jules Sissy Story Ch. 04

(Disclaimer: All depictions of sexual activity occur between consenting adults over the age of 18. This story is very sequential, making previous chapters suggested reading.

This is a work of fiction. All characters are composites of any persons that appear to be represented within. A big thank you to those that help me write this tale by sharing their thoughts and experiences.)

Ginger and Jules Sissy Story -- Chapter 4

Wow, I'm a cocksucker now, I thought as I stood there holding my nightie up and peeing in the middle of that first night of this new phase of my life, and Cindy knew it. She knew what I'd done and asked me if I liked it. Never in a million years did I think this would have ever happened. I started to get hard as the thought of the events of a few hours ago ran through my mind. Maybe I could just sit down and jerk off real quick in the bathroom. No, I better get some sleep. These last few days had been exhausting. I returned to bed starving, tossing and turning the rest of the night.

As I sat at the table with my second cup of coffee, Cindy came out of the bathroom all bright eyed and bushy tailed. I poured her coffee and she started peppering me with instructions after the small talk was out of the way.

"You have a busy day sissy boy, better get started. Let's do shish kabobs for Cheryl and your girlfriend tonight. That sounds good, and it's something you can handle. Cheryl and I are going to the gym this morning, and maybe lunch too, so I'll let you do the shopping and the housework. Make sure you wear your cincher all day too."

"What? I can't go out. My nails, and my ears. We didn't even talk about what they did to my ears yet, Cindy. Why did you have Mitzie do that? What the fuck am I going to do about this?" I reached up and toggled the studs for dramatic effect.

"Lots of guys have pierced ears. Relax. You're going to look so cute with some big hooker hoops in them. But seriously, you don't know what it's like until you've worn them. They'll be fun. If you decide you don't like them that much, you can just let them close up. You'll have to be careful about your hands the rest of the weekend though, yea. I want them to last at least the weekend. It's your first girly weekend after all and your hands are so feminine that way. They're really one of your best features. Mitzie kind of did a number on your eyebrows too. I'd avoid any close up conversations, unless you like people knowing your, you know, a sissy boy. You do look a little different now. It's hard to figure out what it is though, really."

I hurried then, as I wanted to beat the Saturday morning rush. Shopping was uneventful as I avoided displaying my hands whenever possible, until the checker spotted my nails. She looked at them, then looked me in the eye and gave me a raised eyebrow look, but that was it.

I was doing house cleaning when Cindy arrived back home much earlier than I'd expected. It wasn't even Noon yet.

"Hi, shopping all done?" as she approached me. "Good, you haven't dressed yet."

"Not yet, I was going to clean first. You're home early."

"We cut it short today. Something came up."

Cindy came up behind me, cornered me against the counter in the kitchen and kissed me hard on the lips. A tongue probing, wet kiss. She was unusually passionate. Something was up.

She pulled back and looked me in the eyes and said "I need my pussy licked, now," and grabbed me by the shirt collar and dragged me to our bedroom.

As she quickly stripped out of her yoga pants and top, I said "What are you doing?" in exaggerated fashion. It was her favorite line from the movie 'War of the Roses' and we used it when the either of us was acting unusual, or irrationally.

"I'm putting you to work. You've got chores to do." and she continued stripping down to nothing and lay back on the bed, with her knees bent at the edge of it. "Eat me," she added with effect, and she spread her legs. She looked moist.

Not wanting to spoil her mood, I got down on my knees and went to work on her pussy. She was wet, which wasn't like her at all. It was obvious she had been aroused by something, or someone.

She started coaching and encouraging me as she forced herself on me. "Yes, there. That's it, more." It was all very strange, and then she confirmed my suspicions. "Did you taste that cock on my lips?"

I froze for a second, and thought 'no, she's just fucking with me', and went back to tickling and sucking her engorged clit.

"I sucked a cock after my workout today. I was thinking of you sucking Ginger while I did it. It was so strange to think about you doing it too."

I was starting not to doubt what she was saying as she humped my face. I latched on to her and sucked her as I tongued and bit her clit for all I was worth. I found myself becoming incredibly excited at her arousal and dug in for the payoff. It wasn't long before I was rewarded with a quaking, grunting orgasm from her. As it subsided, she pulled me off her pussy by my ears and said "I need a cock". She always wanted something to fill her after cunnilingus and I quickly obliged. It was hard to believe how well things were turning out.

"Yes, fuck me. Harder. Harder cocksucker. I want you to cum in me. Cum in me." She found my nipples through my t-shirt and twisted them aggressively, knowing it would be a challenge for me to cum. As I worked my hips, allowing her to hold on to my nipples, she whispered in my ear. "Cum in me and I'll let you lick it out. I know you'd like that. Pretend it's another man's cum and lick it out of me. You sissies are so nasty. Cum in me sissy cocksucker, then we can get you dressed up for the party tonight. All pretty and sexy, for everyone to see."

I whispered back "I want to cum." I then fell on to her and rolled us over and she lifted off me enough so that I could masturbate. We had done this many times to get me off and she let me pound the head of my cock against her pussy as she found my nipples again and pinched them hard. Neither of us spoke as I concentrated on orgasm. I finally got there, and as my ejaculation started, I released my cock from my hand and she sat on it as I came. It was the kind of practiced sex lovers that have been together a long time have.

Cindy rolled off of me, pulling me with her, guiding me to her pussy to lick her clean. She was musky and sticky and it didn't last long. We rested afterwards and I tried to get details. The only thing I could get out of her was "You know all you need to know for now. It's not that important really. It was just a quickie."

She shushed me from any further interrogation and we lay in bed resting, discussing dinner plans.

After a quick lunch, Cindy said "We need to go shopping for you, I think."

"Why? What do I need?"

"I don't like the wardrobe we have for company tonight. That little consignment shop in the old strip mall had some nice things the last time I was there. It's real small, so we might have the place to ourselves too. Come on, get dressed and we'll just pop in real quick."

The store was a small shop occupying a sliver of a dated business row, likely built before the term strip mall had been coined. It was overstocked with all sorts of women's things, jeans, bags, skirts and tops, shoes and dresses. The proprietor welcomed us warmly. She was about forty and smartly dressed.

"Hi, I'm Laura, how are you two today?"

"We're well, thank you. I love your store. Don't you love it, Hun?" Cindy put me on the spot.

"Yes, it's very nice," I offered.

"Is there anything you're looking for in particular today?"

Cindy spoke up for us. "Yes, we need something for evening wear perhaps, a hostess type outfit I'm thinking, in a larger size."

Laura seemed to key off this remark and looked me over. My freshly pierced ears, plucked brows and red face was all she needed to see to understand the situation. It wasn't the first time apparently.

"I see, having a party are we?"

"Yes, exactly, and we want to make a good impression, don't we, Hun?"

"Yes, of course," I muttered.

"How fun. Size,,, 14 I'm guessing. I don't have a lot in, but lets take a look, shall we," and she led us to the rear of the store to a rack of formals, prom dresses, and suit type outfits. "I just got this in," and she pulled out a sleeveless prom style dress with a billowing skirt.

"That would be perfect, but I'd like sleeves if you have something along those lines," Cindy said, looking over the racks. Then she spotted it. A simple straight line print dress with eye popping huge fuchsia orchids on a black background. I wasn't going to go unnoticed wearing it, that was for sure. It did look nice.

Cindy pulled it off the rack and admired it. "It's wonderful, and a 14 too. I think it will fit, don't you, Hun?"

"If you like, we can sneak you two in back to make sure," Laura offered.

"Oh, could we. That would be so helpful. Feel it Honey. It feels wonderful."

I reached out to touch it and realized why Cindy did it. Laura looked at my french nails and smiled. It felt very nice.

Laura led us to the backroom, which included a private changing room, and she showed us in.

"I may have some shoes to go with, if you're interested?"

"Yes, absolutely, dear. A size ten or so,,, really?"

"Let me see what I can find. You two make yourselves at home," and she was gone.

The dress fit well and Cindy was admiring me in it when Laura cleared her throat and handed a pair of 4" pink heels past the curtain. "How are you doing in there? See if these work for you."

Cindy grabbed them. I could tell she loved them. "We're doing great with the dress. Sold. We'll give these a try. They're perfect with the dress. She shoe horned my into them practically, but we did get them on my bare foot. "It's better if they're tight at first," she assured me. I wasn't so sure about that, and I manged to stand in them for her. Another sale. I dressed and we headed back to the front of the store. A woman had entered and was browsing the jeans rack. She didn't seem to notice what was transpiring as far as my shopping.

"We'll take them," Cindy said, handing them to Laura. Cindy spotted a jewelry display near the counter and made a bee-line for it, dragging me along. She picked some gold earrings, a multi-strand gold necklace, wrist bracelets, and a string of faux pearls, etc.. She provided commentary the entire time, "this will look nice, I think these will go well,,,, do you like this?" She even had me try a few rings on my fingers and found a couple that fit nicely.

"Oh, we should look for a purse to go with the dress, just in case you'll be going out in it," and headed for a tree of handbags. The female shopper picked up on that, if she hadn't already, and turned to look us over. I tried to ignore her appraisal, and I could see her smiling out of the corner of my eye.

Cindy picked out a small pink bag with long straps. It would probably look nice with the dress, I agreed when asked. I just wanted to go at that point. Women took so long shopping, stopping to examine everything they passed. She was driving me nuts at this point, but our audience seemed to be getting a kick out of the production.

"There, that should do it, I think," Cindy finally said. Laura rang up over $400 and seemed quite pleased.

"It was nice meeting you two. Thank you so much for shopping with me today."

I'll bet, I thought.

Cindy prattled on about loving her store and we most definitely would be back. "Here's my number, in case you get anything in that you think would be fun," and scribbled her cell on the back of a card from the store business card holder and handed it to Laura.

"Why thank you. I will certainly do that. Here's my personal number for you. I'd love to know how everything works out for you two; see if everything fits, you know," and she smiled, in a hint, hint sort of way. Great, another potential recipient for Cindy's photo sharing. She allowed me a reprieve, finally, and we were on the way home. I did have some wonderful new things and I couldn't wait to see how the dress looked on me when fully dressed and made up.

Cindy sensed my anticipation. "We're so lucky we found that dress. I love the color. I'll help you with your makeup, Hun. We'll use pink and purples," she said as she reached over and grasped my hand for a squeeze.

"I do like it. Thank you for taking me shopping, as much as I hate it. I'm glad you're enjoying yourself so much."

"You know, this is way more fun than I thought it was going to be," Cindy reflected.

I showered and shaved close, twice, did the skin care regimen Cindy had me follow and was ready to get dressed.

It was quite the project to get dressed, cincher, bra, wide garter belt, hose, panties, forms, chemise. I had to slow down to avoid breaking a sweat. Cindy was in the living room watching TV as I dressed, instructing me beforehand to stop when I got to this point.

"Wow, look at all that. You sure have to put a lot into this, Hun. Do you like carrying those boobs around all the time?"

"I don't mind too much. I'd like a real corset to wear though. The cincher isn't enough to shape me, don't you think?"

"What a queen you're getting to be. Damn, that didn't take long. You're worse than before. Let's get your face on." We spent a considerable amount of time on my makeup. I was still a man, but she did her best. I paid close attention as she coached me and we chatted. It was odd, how starting this adventure had actually brought us closer, so far.

The wig, dress, shoes, and jewelry finished off my look and we were both mostly happy with the result. I still wanted to work on my figure, but I loved the look I was achieving. Cindy complimented me several times on my appearance and insisted I pose for pictures before starting dinner preparations.

I felt sexy as hell as she coached me on smiling, turning my toes in, lifting my chin, etc.. As she did so, I was wondering if she and Cheryl were going to allow Ginger and I some more alone time tonight. I really wanted some more alone time with Ginger, in spite of my mishap the night before.

Once we concluded the photo session, Cindy had me bring her a glass of wine as she relaxed on the couch. "You just don't have the girly walk down, Hun," she mocked as I served her. "Bend at the knees, too, not the waist like a guy does. A corset would definitely help with that. I'll ask Cheryl were your girlfriend got hers."

I don't know if it was her intent, but I had a twinge of excitement every time she referred to Ginger as my girlfriend.

I pored myself a whiskey and water, put one Cindy's old apron's on and started prepping vegetables for dinner. Cindy sat on the couch, sipping wine and texting, with an occasional laugh or giggle. She really seemed to enjoy that aspect of all of this and I was thinking of a way to get a hold of her phone when I wouldn't be caught.

"Honey, could you bring me my purse, please. I want to show Laura how the dress looks on you." I brought her purse to her with a sigh, trying to do a feminine hip swivel as I did so. I thought I was getting the hang of if and the restriction to my gate the dress afforded seemed to help in that respect. Cindy obviously thought I was missing something though. "Heel to toe, Hun. Keep your feet closer together."

I resumed my food prep as Cindy went back to work spreading the results of my ongoing feminization far and wide via text messaging.

"Laura thinks you're stunning, Sweetie. Very impressive what I've done with you," she says. "She would love to see you and Ginger posing together. Don't let me forget to get one of you two when they get here, okay."

"Yes, Dear," I said, trying not to be too sarcastic. It sounded fun actually. I loved to browse online looking at sissy couple photos. It was one of my most favorite things to do and I still couldn't believe we were doing all of this to the extent we were.

"Denise loves your outfit, by the way. She says those heels are cute on you." I don't know why, but my arousal level ticked up a notch at that statement. "I'll ask her what's she's doing for dinner tonight. We should have enough for one more, don't you think?"

I wasn't so hot on Denise getting involved really. The more people involved, the less chance of girl time with Ginger I thought. I tried a sly objection. "Do you think that's a good idea? Cheryl and Ginger don't even know her."

"Oh, I know Cheryl won't mind. I'll invite her and she what she says. Besides, don't you want everyone to see how pretty you look? You're the Hostess with the most-est, Honey," and she laughed at her own bad joke.

"Ah, she can't make it tonight, but she's open tomorrow. How about you whip up a brunch for her and I? She says she's got to see this in person. How about that? Maybe you could wear your little pink outfit for her."

I thought that was going to far. "No, I don't want to be wearing a sissy dress in front of you two. Really, thanks, but no thanks. It's a sissy dress, Cindy."

"Well, yes, I know what it is. So, when do you wear it then? Just when you're having sleep- overs with your girlfriend or something. I think Denise would love to see it on you. You know, because you're such a stud. Yes, you're wearing it all right, for sure... She says she'll see you at 9:30 tomorrow. My, such a busy weekend it's turned out to be," and she laughed and held out her glass for a refill.

I knew she was still holding that over me; the stud thing. I was young and could orgasm two, maybe three times a day on a good day back then. The tables had been turned, whatever the fuck that was supposed to mean. Whatever it means, it was going to be more dress up time for me tomorrow. It was definitely turning into a long weekend.

Cheryl and Ginger arrived just at dark. I wondered about that as any prying neighbors might be getting an eyeful, depending on how Ginger was dressed. I had visions of a silly evening gown on Ginger at some point, just like the television show.

Ginger was actually quite sophisticated in a black knee length dress with full button front, a stylish belt, modest heels and straight red hair this time. He wore a fitted jacket that accentuated his corseted figure. From a distance, he just seemed a bit tall. He looked hot I thought actually, as I welcomed them at the door. I was so glad that Cindy had taken me shopping for the dress. I would have otherwise felt under dressed.

Cheryl wore simple comfy jeans that accentuated her nice figure as well, with a sleeveless blouse and similar jacket, with flats.

"Hi, come in please. Welcome to our home." I had assumed a subdued speaking voice when dressed, without forcing it too much. It was starting to feel a little bit comfortable. Ginger handed me a bottle of wine as they entered and said hello.

Cheryl jumped on our tepidness. "That's no way for girlfriends to say hello. Hugs now you two." We each took a half step and gave each other a hug hello. It was the strangest thing to me still, hugging another male dressed the way we were, our fake breasts pressed against one another. I would have enjoyed it considerably more without the audience. I wanted to kiss Ginger hello really.

Cheryl was complimenting my new dress and heels as Cindy rose off the couch to join me in welcoming our guests. "Yes, don't you just love it. We made quite a find shopping today. I'll have to tell you about it," Cindy said excitedly. "Come in, come in."

Our modest home doesn't require much of a tour, as most of it is seen upon entry, so the women had soon seated themselves on the sectional sofa. This was all still quite new to Ginger and myself, so we briefly just sort of stood there.

"Well, aren't you going to offer our guests a drink, Julie?" Cindy admonished me. "Your the hostess, remember."

"I'm so sorry, yes, what can I get you both?"