Ginger and Jules Sissy Story

(Disclaimer: All depictions of sexual activity occur between consenting adults over the age of 18. Again, if it’s a cum-rope shooting orgasmathon you desire, you won’t be finding it here, yet.

This is the foundation for what I intend will be an extended series of two sissies and their wives as they explore new relationships and experiences.

There have been many helpful individuals that have assisted me by sharing of themselves to create these characters. I extend my thanks to them and a special thank you to Elke for her input. )

Ginger and Jules Sissy Story.

“Well, he does all of that as Ginger you know. That’s the trick,” Cheryl confided to my wife Cindy as they talked over their lunch break. “That’s his motivation. He was just like John until I found the key to motivating him”.

“What do you mean ‘as Ginger’?” Cindy asked, keenly interested and more than a little shocked. She thought she knew what Cheryl meant, but it was so odd to hear. She must have misunderstood. Cindy just thought that Paul was the dutiful, loving husband that Cheryl was always bragging about. It was turning out to be that it wasn’t just because he was thoughtful.

“You know, Ginger. Gilligan’s Island. Ginger. Big hair, big tits. Adolescent boys were hot for Ginger or Maryanne. Paul was a Ginger fan. But he wanted to look like Ginger, not have sex with her. Well, maybe both.”

“You’re not serious. How did you know he wanted to be Ginger?” Cindy asked, incredulous at what she was hearing.

“His sister, my sister-in-law, told me years ago. She caught him wearing my Mother-in-laws evening gown and heels when he was in high school. She wondered if I’d noticed anything unusual after we had been drinking one night. Turns out I had and he’s been my little Ginger ever since.”

“No way. Doesn’t that bother you? I mean, it did me.”

“What do you mean ‘it did me’? John too, huh. They’re every where I guess,” Cheryl said, laughing at Cindy’s reaction.

“Well, yes. But I put a stop to it twenty years ago. It just wasn’t my thing.”

“Do tell. What was John’s kink?” Cheryl asked, becoming the curious one.

“Well, it wasn’t Ginger or Maryanne. He wanted to be Julie the maid.”

“Yes, that’s a common one, but you’re asking me how to get him to help around the house more? You’ve had what you needed this whole time. What’s your problem, girlfriend?”

“I didn’t like it. I wanted a man around the house. The maid thing was just so weird really.”

“I get that, but didn’t you get fringe benefits? I mean, a maid and all.”

“Oh, he didn’t do much cleaning, and it didn’t go that far. He just wanted to get dressed up and be pretty and get his rocks off mostly.”

“I hear that too. You didn’t get anything out of it at all then?”

“Well, he did get into that cleaning chore. He’d stay between my legs until I told him to stop, yes,” Cindy confided sheepishly. “That wasn’t so bad, but he kept wanting more. He’d do anything when he was dressed, but he wanted more. More dressing up all of the time. He wanted to shave his legs so bad. It was too weird, so I said no more. I wanted the man I married, not a sissy husband. I don’t know how you can get over that part, myself.”

“Oh, there’s ways. I didn’t really get into the Ginger thing at first myself, but when he went on disability and I found his stash of clothes, I figured, what the hell, I’ll take charge then. I like the arrangement now actually,” Cheryl said thoughtfully. “It’s really nice in a lot of ways. I get to do anything I want, and he does almost all of the chores. It does present an obstacle to a social life though.”

“You caught him? But you said he’s been you’re little Ginger for a long time.”

“Yes, but we didn’t take it far. At least I didn’t. I’d just let him wear nighties and panties and stuff to get his motor running since that’s what it took. Then I found his Ginger stash he was hiding in the basement a few years ago. Just some clothes and a Halloween store red wig, heels and make-up. But there are ways to get things to go the way you want them to.”

“What do you mean exactly, ‘there are ways’?”

“You’ll find that the more you let him be his sissy self, or make him, the easier it becomes to control just about everything.”

“Well, I’m going to think about it. It’s not like we have a raging sex life anymore anyway. So if it turns out I don’t really care for him in a panties and a dress, eh,” Cindy said with a shrug.

“Now you’re thinking, and you can spend some time at the gym with me, maybe. You might be surprised at how a work-out at the gym changes your perspective.”

“Well, I’m sure tired of the way things are, that’s for sure.”

Cindy stopped by the mall on her way home that very evening.

I wasn’t expecting what happened that night, but you never know what a new day might bring.

Cindy and I had been together a long time at this point and entering a new phase in life. I had given up my spot in the rat race when I came into a large inheritance. Cindy kept her job as she liked the fulfillment it provided her. Not to mention the fact that insurance was still prohibitively expensive for us both to live a life of leisure. We had a ways to go before that wouldn’t eat the nest eggs. I was happy to hold down the home front in the arrangement.

Cindy wasn’t quite as happy as I was with the way things were going. Several months in she began to tell me so on a regular basis. I’d do some chores, but she still had her “responsibilities” and I only made superficial attempts to pick up the slack. In fact, I did less and less of them as I became comfortable with the way things were. Dinner was still primarily her role, etc..

Cindy didn’t quite see it that way. We didn’t have any knock down, drag out, dish throwing exchanges. She just wasn’t happy with things and I knew it. I just didn’t care. I sat on my fat wallet and enjoyed myself for the most part.

Cindy would tell me how her co-worker Cheryl’s husband “Had a drink made and ready for her when she got home from work. Dinner was on the stove, the house was taken care of, the laundry, the grocery shopping.”

“That’s nice,” I’d say. “He sounds like a keeper all right.” I wasn’t a hen pecked sucker like Paul, I thought. I’d never met either one of them, but he sounded like a real pussy.

Then today, Cindy comes home from work and throws me a curve ball. “I bet Julie would keep house if she were around,” comes out when she finds me in my usual position on the couch.

“I didn’t think you liked Julie,” I replied.

Julie. It had been twenty years since she’d mentioned Julie. Julie was my feminine alter ego when Cindy and I had first gotten together. She had been out of our lives for such a long time now and I wasn’t entirely sure I wanted to see her come back. It was Cindy that had wanted her to go away anyway and I now found it easier to be my male self and all the benefits it entailed. I missed Julie at first, but after twenty years, I had come to terms with it.

“That was a long time ago. I just think it might help us both to try something new now, but familiar. You know what I mean. I know you missed it when I made you give it up for me.”

“Yea, well, I’ve gotten over it I guess. People can change you know.”

The fact was, that part of me hadn’t changed entirely. I spent a fair amount of time on-line looking at the fabulous looking transsexuals that abounded these days. I actually preferred the sissy males though.

“So you’re not going to give it a try for me?” Cindy asked as she batted her pale blue eyes. She loved to use her eyes on me like that. She then dropped a pair of Vanity Fair Lycra panties with tags still attached in my lap. They were wonderful, I thought. I loved new panties, and Cindy knew it. They’re my Kryptonite.

“Maybe just some panties to wear around the house. Or maybe you’d be more interested in doing some chores in a little maids outfit? How about that? Some nice lingerie and your legs all shaved, and a cute little bra to wear under your dress. I bet that sounds good, doesn’t it?”

She had my full attention now and I wasn’t disagreeing.

She took the panties back and snaked her hand into my t-shirt with them. She started rubbing a nipple with the fabric as she let that statement sink in. My cock came to half mast almost immediately in the sweat pants I was wearing. It had been a long time since Cindy had played this way.

“I don’t know. I’m good I think,” I said in an off-hand way. It sounded like work.

“Hmm, Cheryl says Paul loves to do his chores in his little outfits.”

“Outfits?”. My curiosity was piqued and I struggled to control the arousal evident in my sweat pants.

“Yes, he’s kind of cute in skirt and heels.”

“No fucking way.”

“Yup, Ginger the househusband.”

“I don’t believe it. You’re just making that up. How do you know, anyway?”

“Cheryl told me. Let me see if I can get some evidence for you then,” and Cindy pulled out her phone and texted Cheryl. Thirty seconds later came the reply.

Cindy turned the phone to me and said “there you go.”

The reply was a photo displaying a tallish redhead in short black skirt and heels with a pink blouse. Whoever it was, they were obviously not a female.

It was true. I swallowed that sort of swallow of instant arousal. It didn’t go unnoticed and Cindy put her hand on my crotch, confirming my interest.

“Hmm, it feels like someone’s interested,” Cindy said with a smirk.

I wasn’t even making it a challenge for her.

“That’s just from you playing with me.”

“You are so full of it. I told Cheryl this would happen. It’s part of the reason I didn’t allow it all this time. You haven’t changed a bit. You want to meet him, don’t you? Wow.”

She had me cornered now. It had never went away entirely, if at all. The desire to meet another cross dresser. I realized I’d made a huge mistake when I told her that years ago.

My erection subsided as my defensive barriers came up. I just had to keep my mind off of the fact that another cross dresser was just a short cell phone connection away, and my wife held that connection in her hand right now.

Cindy stood and let me have it. “Oh, I expected this to happen. That’s the point. So why can’t you get your pervy jollies and I can get some help around here, and acknowledgment that I’m the one going to work every day. I want equity in this house. I want a cocktail chilling and dinner started when I get home. I want you to appreciate me more. If it takes you being my little househusband to get it, I’m giving you that option.”

Cindy left me to ponder the proposal as she went to change from her office attire. I was kind of bored, and I envied the attractive cross dressers I saw in the chat room I frequented. Their shaved legs in nylons and heels were a particular source of envy on my part.

On her return, I tried to get some clarification of her proposal.

“So, you wouldn’t be telling everyone about this, right? I could still be me most of the time then? It would just be between us. Maybe we could try it for a while, until Winter is over or something.”

“Well of course. I don’t want everyone to think we’re some sort of weirdos or something. It will just be between us, and Cheryl and Paul. That would be fun maybe. You can share recipes and stuff and have a friend to share with. I think it’s important for both of us that we can share it with another couple like that, don’t you? It wouldn’t be some deep dark secret hidden from everyone that way. We could even have dinner parties together.”

That would just be crazy, I thought. Me and another cross dressed husband in the same room with our wives, or maybe even without the wives. That didn’t fit my typical fantasy scenarios of meeting a hot little sissy on the sly, but any opportunity to dress with another CD was still terribly exciting to me.

“We would get together with them? That’s sounds pretty strange, don’t you think?” I thought out loud.

“I think it could be fun,” Cindy continued. We could use some new friends really. We don’t get out near as much as we use to, and you and him would have someone to talk to. Cheryl and I think it might be great actually. Why don’t you go put those new panties on and help me with dinner. Let’s just do it and see how things go. It’s not like your going to get a boob job or something.”

I changed into the panties and tucked my cock in them deep and tight. I didn’t want my arousal to be any more apparent than I’d already revealed to Cindy. The panties were nice and tight, allowing me to present a fairly smooth front. I liked how I looked in them, and how I felt even more.

As soon as I was back in the kitchen and within arms length, Cindy gave me a feel on my ass.

“Do they fit okay, Muffin? Your little butt looks so nice in them,” she teased.

I pulled away from her touch, playing hard to get. “They fit great, actually. Thank you.” She reached for my crotch on the next pass near her and tried to find my package.

“Ooh, got your self under control I see. Maybe we can play after dinner.”

I felt my cock struggle to rise at her touch and teasing. We hadn’t had this sexual tension between us in ages. I grabbed her in my arms and kissed her. Not one of those peckish married couple kisses either. The real thing with passion and a probing tongue. It felt so strange. We had definitely been in a rut. Cindy kissed me back as we held each other tightly. She pushed me away and broke free when I groped her ass with both hands, saying she was hungry.

Cindy browsed the internet looking at clothes for me as we ate dinner. Did I like this, or that, and that might be cute on you. There was a Macy’s nearby and she started looking through options there. Cindy logged in to her account and filled up her online cart. She picked out a shaper, a pair of Mary Jane memory foam pumps for daily wear and a pair of classic pointed toe pumps for special occasions, she said. On and on she went with hose, lots of panties, a couple of bras, starter make-up set, etc.. She checked availability as she wanted to make sure her shopping list could be picked up locally. The single dress she settled on was an above the knee sweater dress with pleated skirt and ¾ sleeves and high neckline. She didn’t want me looking like a slut, she said.

I didn’t see everything she ordered, but the total came to hundreds of dollars. She was excited about all of the savings and kick backs with her discounts and rewards.

Cindy relaxed and texted a bit while I cleaned up after dinner. “I think I like this,” she said, as she watched me do the chores.

I was called to the bathroom shortly after dinner and informed it was time to get ready for the new me. We set about getting me shaved smooth. No hair where it doesn’t belong she said. It felt amazing. I’d always wanted to be shaved bare, everywhere, and that’s what we did. She said that maybe I could grow some back, but wanted to start with a clean slate and go from there.

I fought my erection throughout the process and endured no end in teasing from Cindy as we finished, applying a generous amount of scented moisturizer afterward. I wanted to have sex with her, badly.

She took me to the bedroom and found some old lingerie that I had bought for her years ago and hadn’t been worn more than once or twice. She had told me it wasn’t comfortable at the time. I wedged myself into it as I heard her step into the shower. I agreed, it wasn’t very comfortable.

When she returned, she just dropped her towel and hopped into bed naked. We proceeded to have sex like we hadn’t had in years. She was still warm and smelled fresh when she pushed me down on her and said “Eat me”. I had been neglectful in this aspect of our sex life, as married couples tend to be over time, and she didn’t let me stop until she came with an orgasm that the neighbors probably heard. It was like our first time again. I didn’t know why I had resisted this at first. I felt 20 years younger. Cindy seemed to be enjoying herself as well.

I mounted her after she had her orgasm and easily entered her hot wet pussy. She always liked being filled after I made her cum with my tongue. I felt so sexy fucking her in my baby dolls and as she played with my nipples she teased. “Oh, you’re such a cute girl, with such a hard cock. You like being a girl don’t you? Yes, I think you do. Your cock feels so big tonight. It makes it seem bigger without any nasty hair around it, doesn’t it? You like it, I can tell you do sissy boy.”

Yes, I did like it, very much. It was almost like a dream had come true for me.

After a couple of more minutes of her teasing and taunting and saying harder, girls want it harder than that, she said “Just think, you might be getting a girlfriend to talk to about sex with.” That was it, and I came like a 19 year old. It was a release of years of pent-up sexual frustration that came flooding out of me and into her.

“Um, you came hard, didn’t you,” Cindy whispered pillow talk in my ear. “I haven’t felt you cum in me like that in years. Maybe ever.”

“Uh huh,” was all I said. My lack of completion had always been an issue and Cindy often helped me masturbate after we had gotten her off with vibrators. It wasn’t something I liked to talk about.

We spooned afterwards and soon fell asleep.

Cheryl and Ginger also shared this new twist in their lives that evening. Ginger wanted to know if they were going to meet us, and when, what did Julie look like, what did Cindy look like. Did they know about their special situation?

“We’re working on this weekend, settle down,” Cheryl admonished Ginger. “You’re like a kid that can’t wait for Christmas or something. This is all new to them, and you don’t want to scare them off, do you?”

Ginger felt ashamed at her anticipation. It was just so exciting. Cheryl had said he could maybe have another cross dresser for a girlfriend some day, and now that day was finally near. It had been several years that Cheryl had been calling the shots in their household and he was terribly excited.

Cheryl had had her own boyfriends for a while now, and they didn’t share the sex life they once did. Hardly at all actually, and as their relationship evolved, Paul’s desires as Ginger shifted to wanting one with another cross dresser for sexual gratification.

Cindy and John must be eased into this lifestyle he thought. It wasn’t for everyone, but it worked for the two of them. Almost anyway. Since Cheryl had cut him off almost entirely sexually, he was often frustrated. This could be a perfect solution to that, he thought.

In the morning, Cindy informed me that we would be getting together with Cheryl and Paul, or rather Ginger, this coming Saturday at their house. I was going to be going as Julie. I instantly felt my heart beating in my chest. No one but Cindy had ever known about this side of me. Not in person anyway and I hadn’t prepared myself for this rush of anxiety.

“I’m not ready for that!” I blurted out. “I’ll look silly. I don’t have clothes, or a wig, or know how to put make-up on, or anything.”

“You have some work to do then, don’t you?” Cindy replied. “I’ll let you know if you can pick up our order today and we’ll go from there. In the meantime, you can watch some YouTube for pointers, I’m sure.”

I did exactly that as soon as Cindy left for work. There must be thousands of videos on makeup, how to walk, seven things a cross dresser should never do, etc., etc. I spent the morning watching them and imagining all the looks I could try. After suppressing this for twenty years, I felt like a horny teenager.

Around Noon I got a text from Cindy that my order was ready at Macy’s and I should run down and pick it up.

She then added, “Be sure to get pretty for me with dinner started when I get home. I can’t wait to see your pretty things. There’s a bimbo wig in our Halloween stuff.”

Cheryl and Cindy caught up at lunch.

“I feel kind of bad about it. He was so cute and super horny and the sex was okay, but I’m just not that into him being feminine. At least he smelled nice and all, but he looks so femmy all shaved like that,” Cindy confided. “He was so horny I let him do his thing, but I don’t know if this is going to work for me.”

“You’re preaching to the choir, sister,” Cheryl said as she reached out for Cindy’s forearm to console her. “Paul and I didn’t get this way overnight ourselves. It takes some time to adjust to being in charge, and having a feminine man around the house is a little strange a lot of the time, I know. We’ve learned to accept it though, and the fringe benefits can be pretty awesome, let me tell you.”

Cindy was intrigued and was pretty certain she knew what Cheryl was referring to, but she didn’t come right out and say it. She wanted to hear it from her in no uncertain terms. “These fringe benefits you keep mentioning are what exactly? You’re not talking about housework, are you?”

“No. I’m not. I’m talking about men. Real men, with firm hot bodies and big cocks. Some Cougar time for me,” Cheryl said in a quiet, naughty whisper.

“How can you do that? I mean, what about your marriage?” Cindy said, with a hint of judgment in her voice.

“Well, it wasn’t my intention at first. It just kind of happened. I had the same issues you’re talking about. I want a man to have sex with me. Not, you know, just like you just said. I started looking around at the gym and one thing led to another, and another, and before I knew it, I was getting my brains fucked out by an 8″ cock. It was such a glorious feeling, I haven’t been able to stop.”

“But, Paul doesn’t know about that, right?”

Cheryl came right out with it, “He does now. Has for quite a while, yes. He was upset initially, and gets a little jealous still, sometimes maybe, but now I realize he always wanted it. He’s never seen me with another man or anything like that though as far as I know, but I’ve had to accept that he’s a sissy. I think it’s their nature really, and it’s not like he’s innocent himself. You must be thinking about where this leads for you two, right?”

Cindy had felt a tingle at Cheryl’s mention of an 8″ cock and she was a little distracted by the thought of it.

“I don’t know. I mean, well, yes. John’s not exactly being the man I thought I was marrying, but this was kind of my idea, too. But what do you mean by he always wanted it?”

“I didn’t realize it at first myself, but it finally dawned on me. He’s a sissy boy and he wants cock, and if I’m getting some, then maybe he can too. Or, he just gets horny at the thought of it. I don’t know, and at this point, it’s not that important to me to understand it. Let me ask you this. Did John ever try to get you into swinging, or anything like that?”

Cindy let out a quiet sigh. “Yes, years ago. I never thought of it like that, but yes, he tried to get me interested in getting laid by a big stud or getting into swinger groups. I thought it was fucked up, but never thought about it like that. Yes, since you put it this way, I see what you mean.”

Meanwhile.

I walked into Macy’s and headed for the in-store pick up counter. It was staffed by a young twenty something girl and an older woman, about my age.

“How can we help you today?” the young girl said as she greeted me.

I acted as if I was just playing errand boy for my wife. I would have preferred the older clerk’s assistance actually. I thought I could remain more inconspicuous with her, possibly. The young clerk was very cute.

“Ah yes, that big order. We didn’t get everything, but we have almost all of it for you. We didn’t have size 10 in both pairs of shoes, but we have the pumps and the comfort soles should be in tomorrow. I hope that’s okay?”

Damn, she said “you”, not “your wife.” It occurred to me that size 10 heels would be a little unusual. I started to blush. They had obviously seen the types of things and quantities Cindy had ordered as well. I was sure they knew the clothing and make-up were actually placed on order by myself, or at least for me. It was a complete feminine wardrobe after all. The idea that I was bare shaven and moisturized in my new panties wasn’t helping the situation either.

“Um, yea sure. That’s fine, no problem,” I said, trying to act as if I regularly picked up a complete women’s wardrobe.

“Great, we’re so sorry about that. The inventory was just off for that size. Is there anything else we can help you with?” she said as they older clerk set about bringing out several large bags to fill the order. “We have in-store styling consultants, if you know of anyone requiring assistance at all?”

Anyone, meaning me. How nicely put. I realized things have certainly changed.

“Um, no, I don’t, thank you so much,” I replied as I tried to gain control over my embarrassment. I wasn’t expecting to be made by a 20 something year old girl today. It was all I could do to carry everything to the car in one trip, but I sure didn’t want to make it two trips. I kept struggling to keep my jeans from sliding off of my hips due to the smooth finish of the panties and one trip was enough.

It was like Christmas, times two, when I got home. So many wonderful things to try. I chose a new pair of high cut panties, light tan pantyhose, the waist trainer and a wonderful full cup padded bra, all in matching nude.

I felt so femme as I slipped into my new things. It was heavenly. I tucked my cock and did my best to ignore it and not mess the new panties. I chose a pleated black skirt and bone colored silk like blouse. I stuffed the bra with spare panties, admiring my new shape in the bedroom mirror. It was hard to resist playing with myself, but I managed to keep control. I didn’t want to spoil any opportunity I might have tonight, I thought. I decided I needed to lose some weight.

Putting on the heels almost put me over the edge though. I had never worn heels with hose and shaved legs and it was overwhelming. Gawd I looked hot. I was a little unsteady, but they were only 3 inch heels and I adjusted pretty well for a beginner. The wig I found was a cheap blonde bimbo wig of Cindy’s and looked it. It would have to do, I thought.

I set to doing my first real make-up job on myself, referring back to a couple of YouTube and Sephora videos for pointers. I lightly trimmed my eye brows and plucked a few. It seemed counter-intuitive that the goal was to create a thicker, more defined brow line, but I thought I’d done a reasonable job and looked somewhat pretty.

I put the wig on and brushed and combed it out as best I could. It looked horrible. Hair was so important and I could see it was going to be an issue.

On the way home from work that evening, Cindy called her stylist. “Hi Mitzy, how are you? Hey girl, I have a huge favor to ask you. I’d like to bring my husband in for a make over… Yes… Well I loved that story you told me about the guy you did, and now I need the same… Friday, after hours… Nails? I didn’t think of that… Yes… That would be great. We’ll see you at 5:30 this Friday then. Thank you so, so, much… Yes, it should be fun, I think.”

If he wanted to be girly, he was going to get girly, Cindy thought to herself. She had been thinking about how John had wanted her to have sex with other men all afternoon and she was mad. This would definitely be fun, for Cindy and Mitzy.