Ginger and Jules Sissy Story Ch. 02

(Disclaimer: All depictions of sexual activity occur between consenting adults over the age of 18. It's not too sexy yet, but it will get there.

Chapter 1 is suggested reading.

In Memorium to Dawn Wells. May she rest in peace. She will forever be remembered.

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 2

A light fish and greens dinner was started and the table set, with white wine chilling and mood music playing for Cindy's arrival. It felt odd to be doing it all dressed as I was, but I wanted to show Cindy my appreciation. My nerves were shot as I awaited her arrival.

"Oh, wow. I'm impressed," Cindy exclaimed as she entered. "What's that I smell? It smells good, whatever it is. Not too bad," she said, giving my new look and a set table the once over. "Turn around, let me see."

I did my best to pirouette for her. It felt so fucking girly and silly, and stupid, all at the same time.

"You're going to need to work on that, Dear. Why aren't you wearing the other shoes I ordered? Those are a little over the top, but you do look nice in them. I bet you love them, don't you? You look like such a silly sissy, really." She was seeing me the way I felt apparently.

"They didn't have the other ones in. I'll need to go back for them. They knew all of this stuff was for me, by the way. It was embarrassing."

"Yea, well, you might need to get used to that. Aren't you forgetting something?"

I leaned in to kiss her, and she turned aside. It was a telling, visceral response and we both felt it.

"That's not what I meant. Don't you have a drink for me?"

"Oh, sorry. It's your favorite," and I served her white wine. Serving her a glass of wine seemed a big deal to her. Serving her at all was maybe what it was about actually, now that I saw the way she responded.

"Well did you try everything on? We should make sure everything fits if you have to go back for the other shoes, and that wig looks terrible."

"Yes, I should do that, I guess," I replied, but I wasn't in a hurry to go back, and returns presented even more opportunity to confirm the situation to the employees. I hoped to let it go.

Cindy sat herself at the table. "Come stand right here. I want to send Cheryl a picture," and she aimed her phone at me. "No, smile for the camera. A girl looks so much better with a smile. That's better."

She had me strike a few different poses and once she was satisfied, texted Cheryl. Cindy smiled and giggled to herself, apparently with some sort of inside joke at my expense. Cheryl responded quickly and a lively text exchange ensued as I put dinner on the table. My appearance was now documented with photos.

I recalled how I was always interested in photographing myself during my earlier dressing days. There was just something compelling about pictures of myself when I dressed.

"Cheryl wants to know what you're doing for tits," Cindy remarked, still focused on her phone. Paul has some silicone falsies to give him some weight and jiggle. I agree. You don't have the right jiggle with a stuffed bra. I'm going to go ahead and get some ordered real quick before we eat. That will probably help you feel more feminine too."

"These look good, don't you think?" and she showed me a pair of silicone forms that were supposed to have natural bounce and realistic nipples.

"Yes, those look good, if you think so," I replied, viewing them.

"If I think so. You're so funny. It's all for you, Hon. Done, they should be here Friday."

After we had finished dinner and I cleaned up, Cindy had me refill her glass and patted the couch next to her.

"Come sit with me. We need to talk." I felt a knot in my stomach as I took a seat beside her and crossed my legs in as feminine a manner as I could muster. I couldn't help admiring my heels and slim ankles, in spite of the situation.

"So, we have a problem already, don't we?" Cindy said as I adjusted next to her.

"I think I know what you mean, yes." The kiss. It hung in the room like a bad odor when it occurred, or hadn't.

"Yes, the kiss to welcome me home. That's no good. I'm thinking we need to change this up. Maybe set some boundaries here to be able to make us both happy with the situation."

"Boundaries. What sort of boundaries are you thinking?".

I'd heard this before, and it spelled the end of Julie twenty years ago.

"Well, I really loved coming home and having you serve me dinner, Hun. You don't know how much that means to me, but I can't bring myself to kiss you hello when your dressed like this. You know what I mean. I just can't, and I don't want that. Do you want to dress like this all of the time, really?"

I had considered this myself already. "No, I don't actually," I admitted to her and myself. "It's so much work to do. I can't imagine doing it every day really. It will take the fun out of it too, I think."

"Yes, exactly. The fun," Cindy replied as she reached out and gripped my hand. "It's about trying to find more happiness, for both of us. I realized it after you came in me last night, it makes you happy. I don't think you've cum in me in years, and especially like you did last night."

Damn, I didn't like to talk about this.

"Have you?" Cindy pried for a response.

"No." It was an undeniable fact we were both well aware of.

"I liked it when you did. So, I'm thinking, we shouldn't let this crowd out the rest of our life, just be a part of it. Isn't that what you really want, after all?"

"Yes, it is. I like things the way they are, for the most part."

"Me too, mostly, and I see that expressing your feminine side might be good for the both of us, within reason."

I waited for the qualifiers and they didn't come.

"What does 'within reason' mean?" she forced me to ask.

"I'm not entirely sure. If I tell you no, I guess. If I wave my finger in your face, it means no. If I catch you fucking around, it means no and I take half of everything. You know, like it would always be. I might want to try some things myself too, though."

"What kind of things?"

"Well, Cheryl and I were talking and she gets her womanly needs met from other men. That kind of thing." She squeezed my hand tightly as she spoke those words. It wasn't easy for her either it seemed.

My stomach felt like it had turned upside down as I heard them. "Well how is that fair then? I can't believe you just said that. Why would you say that?"

"Well, it's often part of the deal, Cheryl tells me. I hear Paul gets off on it, a lot, and Cheryl and I were talking and I remembered you did try to get me to swing with you, or for you, years ago. You asked me to, remember? Hey baby, do you want to try a big cock out? Cheryl helped me realize it's because you wanted a cock yourself and it's also probably trying to compensate for your inadequacy too. It's okay, I understand, sort of."

She just left the statement hanging there for me to digest.

"Um, so you want to do that now? That seems kind of strange, doesn't it?"

"I don't know if I do or not. I guess we'll see how it goes. You know what else I was thinking. Since I don't want to come home to you all dressed up every night and it will complicate things in so many ways, how about you buy yourself some little maid outfits to wear to clean house and make breakfast for me on weekends to satisfy your urges. You sure loved that little black satin outfit you had a long time ago. Julie the French maid wasn't it?"

I did love that dress. It was so short, my panties were visible when I bent over. I always wanted a pair of heels higher than 3 inches to go with it, but shoes weren't as easy to come by, or as cheap as they are now.

"I think just a few things for when it's not just us will do then," Cindy continued as my mind wandered back twenty years or more. Unless there's something else you want to tell me?..."

"No, there isn't." I knew what she was fishing for, and I had no intention of going further than dressing up occasionally. We weren't in unfamiliar territory and I knew that. I also didn't want to be a domestic servant. It had always been about sexual stimulation and ultimately satisfaction for me, then it was on with the day, just like anyone else really.

"Okay, just making sure. I had to ask. You're the only one that knows after all, and I don't want any surprises later. So you just want to get dressed up and have some cock once in a while maybe then?" Cindy said with a smile. I couldn't understand why she was smiling. I had always been slow to catch on when people were just fucking with me.

"Let's just say I'm a transvestite. I get sexually aroused by it, yes. Sorry, I can't change that," and I turned away and looked at the floor.

"Yes, I realize that now, or should I say, I'm going to try and accept it better. I just want us both to be happier with... everything. So let's spend some time getting you in touch with your feminine side. I realize that might mean you getting a big cock stuffed in your face."

"Why do you keep saying that?" I said to the floor, defensive barriers going up.

"I've seen your browser history, for one. You didn't know that, did you?" Cindy said with her eyebrows raised. "I'm not as dumb as you think I am."

Fuck, I thought I'd been more careful about that.

"No, I know you're not dumb. Well, I don't do that all the time," I lied.

"Oh sure, if that's your story, go ahead and stick to it. But why should you get all those big cocks all the time. I might want one myself once in a while. Cheryl sure speaks fondly of them. It makes me horny just thinking about it sometimes lately. I think I'm having a mid-life crisis or something maybe, I don't know. I'm going to go change into something more comfortable and we can play again though. How about that. But sorry, I won't have a big cock like those transsexuals you look at all the time."

Fuck.

With that, Cindy gave me a kiss on the cheek and left me on the couch alone with my thoughts. I sat there admiring my new heels as I tried to get 'big cock stuffed in your face' out of my head; and that 'Cheryl sure speaks fondly of them' comment. Cheryl seemed to be having a strong influence in all of this, that's for sure.

Cindy soon called to me, "Hey Lover, come in here."

I attempted my best heel to toe gait as I entered the bedroom and found Cindy had placed all of our purchases out on the bed and seating bench. She had changed into a short chemise she seldom wore and was holding the dress she had picked out. She looked great to me, having kept a careful diet over the years. I could see her nipples peaking out through the fabric and she wore tummy control panties underneath. I'm sure they were a part of our Macy's order.

"You need to try this on, sissy boy. I want to make sure you have things to wear for your initiation weekend."

I stepped out of my heels and stripped down to my underwear. This was the first Cindy had seen me in my new underwear and she started feeling my waist and prodding my tummy.

"Not bad, all in all I think. You need to work on that middle of yours though, just like all of us girls. Let's see how the dress looks," and she helped me into it. "No, no, not going to make it. You're going to need to go up to a size 14. Darn it. Well, that's one return. You might make a size 12 though if you lose a few pounds."

We went through the rest of the things with her teasing me throughout the process. "Oh, this is going to be cute on you. That will feel good. Don't you love these panties?" After having been together so long, she knew what buttons to push, she just hadn't done it for such a long time. My restricted cock was becoming painful as she went.

"I think you should wear panties every day, Honey. That will help keep you motivated for the weekend and you'll get a little something out of it during the week. Yes, let's do that. Clean out your drawer and we'll put these in there and we'll get lots more so you have plenty on hand. Just in case you have any accidents." She was having more fun than I was with it all.

She approached me again. As I changed out the clothing in my dresser she started feeling my crotch and digging to find my cock. It sprang free when she lowered my hose and panties and I quickly came to full mast for her. It had been such a long afternoon of self denial and Cindy was playing with me like a horny teenager.

She grasped me with a fist and squeezed just a little bit, causing me to become weak in the knees, whispering in my ear "you sure are hard tonight, aren't you?" Is it your panties, honey, or have you been out there thinking about big cocks." I hated how much I loved the teasing.

She rubbed the tip with the pad of her thumb as the pre-cum oozed out and I tried to pull away from the sensitivity in my urethra. It was an involuntary reaction, but I wanted more and she knew it. I was disappointed as she pulled my hose and panties back up over my cock and traced the outline through the fabric. A small wet spot grew from her touch as my abdomen tensed.

Cindy then held me by the hand and led me to the bathroom. She pulled the ugly wig off my head and demonstrated the proper routine of make-up removal and moisturizing. It was an oddly intimate few minutes as I stood there in brand new lingerie while my wife instructed me on skin care. I paid close attention and briefly forgot my sexually aroused state, likely from the fact I was looking at my male self in the mirror from the neck up.

Cindy handed me a deep green satin tie string nightgown when we returned to the bedroom. "Put this on and see how it feels," and she jumped into her side of the bed to watch me strip and put the nightie on. It felt fantastic and I came to her to adjust the ties to bring the small cups to the proper place on my chest. My hard nipples were apparent through the fabric and she made sure to run her hands over them as my erection tented the fabric below.

"Oh, your nipples are so hard tonight," she said as I reached out and felt for hers in return. I wondered why we couldn't have just done this more often as I found her nipples and gave them a gentle twist with thumb and forefinger.

"I want you to cum in me again," she said as she pulled me down on top of her. Fuck me and cum in my pussy, lover girl. I want to feel your cum in me," and she reached over and turned out the light. I felt the front of her control panties, reveling in the texture and compression of her belly. Finding the waist band, I rolled them off her and got between her legs. I tried to put my head down and lick her first, but she stopped me, saying "No, fuck me now. I want you to fuck me and cum in me now." I moved up on top of her and she guided my cock to her wet, waiting pussy. I didn't often find her as wet and ready as this and I entered her smoothly and without resistance.

We found our rhythm and played each others pelvis. As I tired, I propped myself up on my hands and thrust as deeply as I could, trying to stimulate her clit. Cindy reached up and caressed my chest through the fabric of the nightie, causing me to increase my tempo as I tried to find that release point of orgasm.

Sensing my frustration, she started talking "does that feel good, you have such hard nipples sweetie" and I slowed, allowing her to really get a hold of them. "Cum for me, Lover. Cum in me. I might let you taste me. Would you like that?" I might, I thought.

I exhaled deeply and continued to push against her. She tried a new tact with "I was thinking maybe I'd loan you out as a sissy maid to my friends. Would you like to do that? Get all dressed up for them too and clean their house."

She felt me respond to the thought of that humiliation and continued. "Oh, you like that do you. You want Denise to see you all dressed up sexy, don't you. In panties and heels and your new titties we ordered. Wouldn't that be fun? She might make you lick her pussy again. Do you remember when you fucked her? She'll love seeing you in bra and panties." With that I increased my pace to cum and felt it making it's way from my scrotum to release into her. I shuddered and buried myself in her, and with short strokes I came inside her with a shudder.

"Yes, that's a good boy. You're such a kinky sissy boy though. Damn. Get down there and lick me until I cum. Make me cum on your face," and she pushed me by the shoulders to her sticky wet pussy. I made an attempt to concentrate on her clit and avoid the slickest of her labia, but she would have none of that and placed her hands on my head and lifted herself to my mouth. "Eat me panty boy. Lick your cum out of me...Yes, that's it," as she rubbed herself on my face.

We continued this coupling for what seemed like forever as I struggled to breath, until finally, she reached her own climax. She put on quite the show as she grunted and quaked with my head clasped between her thighs, until it finally subsided and she collapsed.

She lay there in bed eyeing me as I returned from showering the cum off my face and joined her in bed. I snuggled up to her and cupped one of her breasts and she clasped her hand over mine.

"You don't mean that do you, about Denise?"

"Why, does that bother you? It seemed to me you like the idea."

"Yes, but you wouldn't do that really. Tell her about this."

"She's my best friend. I tell her everything. She thinks you look cute all dressed up."

I had already gained some hardness back from the cuddling and my cock reacted against her ass cheek. It had been a huge fantasy of mine forever and it was an involuntary response.

"I felt that. Damn, you're such a pervert. Go to sleep now."

Tomorrow would be another interesting day I thought as I tossed and turned.

"Be sure to give yourself a good once over with a razor today, Lover. You're starting to get scratchy. I have something special planned tonight so we won't be needing dinner either. You're new boobs should be here today too. That should be fun, and don't forget to take your dress in for an exchange. You'll be needing it, and go ahead and pick up anything else that catches your eye. I gotta run. Be ready at 5:00 tonight," and she gave me a quick kiss before heading for the garage.

"Don't forget to moisturize", she yelled over her shoulder and was gone.

No dinner and something special. What the hell was she planning to do to me now? I'd, or rather Cheryl, had created a monster.

I prepped myself thinking about Denise. Why would Cindy want to share this? I thought we agreed not to let this into our regular life and we still saw her from time to time. It was such a long time ago now I didn't even think much of it anymore. But it was one of my great claims to stud-man's ship. Yes, it was that, and Cindy never liked it, at all. I had prodded her into it. I didn't get to cum in Denise, but I was close when I got her to cum. Now that fifteen minutes of manliness was gone to me. Damn, I wonder if she thought of it that way?

I chose a pair of Bali control panties for my trip to the mall.

The scent of the moisturizer was evident as I approached the counter to exchange the dress. The same matronly clerk and a different young female were working the counter. I'd arrived shortly after opening in an attempt to avoid other shoppers.

The bubbly young associate greeted me with a happy "Hi, welcome to Macy's, blah blah blah. I was annoyed with the usual corporate chit chat shtick.

"Hi, I need to make an exchange on this, to a 14," as I set the bag on the counter.

"Oh, I'm so sorry it didn't fit" as she pulled the dress out to examine it. I stood there trying to be cool about the situation. "Let me go check stock. Be right back," the eager young woman said as she departed.