Ginger and Jules Sissy Story Ch. 03

(Disclaimer: All depictions of sexual activity occur between consenting adults over the age of 18.

Previous chapters are 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 3

Cheryl and Paul's home was well lit now that darkness had fallen. I saw a person peaking around the drapes as we came to a stop. I couldn't make out any features of who was peaking, but it was apparent that I wasn't the only one anxious about what was about to transpire. A wave of panic overtook me as I stared at the shadow cast upon the draperies.

"Are you coming? Everyone is invited," Cindy's voice broke in, bringing me back to the present. "Join the party, Honey."

"Yes, sorry," and I grabbed my purse and caught up.

As we clicked our heels up the walk, I thought to ask, "But how did you know where you were going?"

"I've visited once or twice, of course," Cindy said as she turned and gave me that 'you think I'm stupid or something' look she gave me from time to time. I guess that would make sense, yes. It was a big decision we had made. Well, Cindy had made. I had just been following my sexual instincts, without too much thought to anything else.

We must have made for an interesting group to any inquisitive neighbors as we made our way to the front porch. Annie and Mitzie had wonderful asses in their tight skirts and heels. I wondered if Annie's pussy tasted as good as she looked. I bet it's as sweet as molasses I thought as I watched her ass wiggle ahead of me. She walked in heels and skirt in the most intoxicating fashion. I was feeling better already, but damn, I had to pee.

A dog was making a ruckus as we approached and we heard voices making demands for it to settle down. "They have the cutest little Eskimo dog, but Muffin is a bit of a pest," Cindy warned us.

Cheryl and Ginger opened the door together. Ginger held the dog against his right breast as they greeted us and invited us all in. My first impression of Ginger was 'wow'. He wore a Ginger Grant red wig with a very retro outward flip. His makeup used a pinkish palette and was flawless. The eye makeup was a bit overdone, just as I remembered it should be, causing the observer to be drawn to them. Her facial makeup was perfectly smooth, contrasting nicely against his shoulder length red hair and brown eyes. Even Mitzie and Annie were impressed and would soon be giving him approving compliments.

We were about the same size I guessed, but he possessed the better feminine shape. He wore a tight skirt with a closely fitting silk blouse and wide belt. His breasts appeared naturally large and heavy as he gripped the anxious dog.

Cheryl was a few inches shorter, but similarly dressed, with dishwater blonde hair. She had a nice figure in skirt and heels. It seemed to be a uniform tonight. Feeling out of place in my dress with it's high collar and flowery print, I appeared very much the debutante of the group.

Introductions were quickly made all around by Cindy and Cheryl. Cheryl then put the onus on Ginger by taking the dog from him and forcing the issue with "Now that's no way to introduce yourself to your new girl friend. Give Julie a nice hug, Dear." Ginger, without hesitation stepped to me and embraced me.

It was the oddest feeling, being hugged by another cross dresser. I was accustomed to hugging Cindy, whom I possessed a significant physical advantage over. Ginger's strength was the thing that impressed me initially, not the fact that we were pressing our fake boobs together, as I would have expected. The sexual aspects soon followed and I felt a tingle in my panties. I was more than a little self conscious, but still able to be aroused. I had to pee.

"Aah, that's so sweet," Cindy was the first to comment. "We just knew you two would get along."

I blushed and had to quickly request to use the bathroom.

"Down the hall on the right, Julie, and we only sit in my home, Dear," Cheryl instructed me. Still reluctant to speak, I simply offered a "thank you."

I could hear rather loud laughter as I sat and relieved myself. I surveyed the room as I did so. It absolutely sparkled. I could see how it would appeal to Cindy, her having already visited previously. Cheryl definitely put her live-in house husband to work, it appeared. I could only think it must be a lot of work to keep this level of housekeeping up, on top of looking like Ginger did. I had no intention of emulating this.

I was still feeling somewhat aroused and I had to settle for leaving my cock somewhat to the side in my control top panties and hose as I adjusted myself to exit the bathroom.

As I exited, I was met by Ginger blocking my path. He looked into my eyes and said "You look great" and simply and quickly advanced and took me in his arms and kissed me full on the lips. As I felt his embrace and his hands roaming down to my ass, I reciprocated his kiss. I was getting that feeling I got when Cindy had rubbed my ass earlier. It had an amazing effect and I wished I had known how it felt to women when I was younger.

Our lips yielded and we gently touched our tongues to one another. It felt sublime kissing another pair of lipsticked lips. It was all happening incredibly fast as we pressed against each other as much as our breasts would permit, our hands exploring each other. I felt my cock responding in my hose and panties, struggling to find room to expand. I had waited a life time for this moment. Ginger was acting as if he had been waiting even longer as he started probing me with his tongue.

As I felt past the edge of the cincher of his firmly encased waist, hoping to return the exotic effect of having my pantied ass rubbed, is when Muffin bit me. She had sneaked behind me, and either being jealous, or protective, nipped my right calve. It wasn't a bold, hold on and rip flesh bite, but a sneak attack nip and it felt like a Yellow Jacket had stung me. I struggled to get free of Ginger, and he not knowing what was happening, didn't let go. It actually seemed that Ginger acted as if I was trying to thwart his sexual advance and we struggled just a bit. Muffin seeing this, came in higher this time, got a hold of my dress and I heard it tear. Ginger finally realized what was happening and yelled at Muffin. It was so strange hearing that male voice come out of that feminine appearing face, it even startled me as Muffin beat a hasty retreat.

"Bad dog, get home!," and Muffin scampered down the hall, into a bedroom and what turned out to be her kennel. At least the dog was trained. Ginger chased after her as fast as he could in heels and tight skirt and locked the dog in her cage.

"I'm so sorry, are you okay? Did she get you?"

"Yes, but I'm sure I'll be fine," and I looked and did see my hose were torn and a speck of blood at the point of contact. It still stung. It wasn't the first time a dog had bit me. Even in play it hurts though, and this dog wasn't playing.

"What happened to the women?"

"They're off to dinner. We're on our own, Sweetie, but look at your dress. Damn her. Let's go get that cleaned up. I'm so sorry."

Ginger led me back into the bathroom and bent down to examine my leg. "You're going to need to take those hose off so we can get this cleaned up."

Looking down and seeing that Ginger was right, I flipped off my heels and reached under my dress, stripping the ruined hose off in a single motion. It appeared the dress had been destroyed as well. Ginger stood and I was suddenly feeling rather diminutive in his presence as he towered over me. His tits had gotten much nearer however, which I liked. Too bad they're not real, I thought.

He cleaned me up with hydrogen peroxide and a large square bandage and I was good as new, but feeling much closer to naked in nothing but panties and torn dress and I reached around to see if it appeared salvageable. Probably not.

"We'll replace your dress, of course. I'm so sorry."

"Oh, don't worry about it. Cindy picked it out anyway. I thought it a bit prudish myself."

"We'll have to get you changed into something more sexy then, won't we. I think most of my things will fit you. Follow me." Ginger had a nice, practiced sway to his walk, I noticed. How did they do that, I wondered. I followed him with my heels in hand. I felt my cock starting to swell again as we went.

As we entered the back bedroom, I felt as if I had entered a secret sissy hide-out. There were wigs on shelves, a lighted vanity mirror and makeup desk. Extra chests of drawers with necklace stands on the top of them, a love seat upholstered in pink and white, and on and on. It smelled like the department store fragrance counter too. One side of the room was a closet wall with mirrored doors. Ginger turned me around and unzipped the dress, letting it fall to the floor.

As he stood behind me I saw our reflection in the closet door mirrors opposite us. My cock was nearly fully erect just from following him down the hall and pressed against the front panel of my panties. At 5", I'm not impressive, but did look kind of hot that way. Ginger seemed to agree and reached around me and touched my cock with the tip of his manicured finger. I was almost instantly fully erect and felt weak in the knees as he gently played with the outline of my cock in my silky white panties. He wrapped his other arm around me and held my girdled waist tightly, pressing me against him. I could feel his breasts on my back and I pushed back against him and wiggled my butt.

As I felt the size of Ginger's cock against me, it occurred to me that Cheryl's fucking around wasn't about cock size. Gingers felt plenty big enough to satisfy.

As my thoughts returned to my own cock, I was consumed with the desire to orgasm. Without heels, we didn't line up well and as I felt him in the small of my back, it only made me hotter.

As I started making slight moaning sounds, Ginger whispered in my ear. "I want to taste that girly little cock of yours." I moaned again and arched my back to push my ass against him.

Ginger then started using his thumb and forefinger to masturbate me through my panties. Having easily been able to cum while I also could watch it happen, I whispered "you'd better stop then, if that's what you want." He caressed my little ball sack through my panties and I pushed back against his hardness even more forcefully while rubbing against him. Ginger then took me by the waist with both hands and pushed me away.

He led me to the pink love seat and sat me down and quickly getting to his knees, he pulled my cock free of my panties. He started slowly at first, licking the pre-cum from the tip and tickling my urethra with the tip of his tongue. Then it was the full head in his mouth and he swirled around the head with his tongue. I wanted to do the same to him.

As I placed my hands on his cinched abs, he circled his thumb and forefinger around me and pulled it out to take it as fully in his mouth. He continued bobbing on it, retracing the motion and sucking the head with his lips locked on it. Then a little tickle with his tongue, and back down again, and again. He continued to repeat the same technique, until he felt me arch my hips, and for the last time he locked onto me and I came. I shuddered and shot my cum into his mouth and he never released it from his lips. I'd never had my cock sucked like it before. I finally finished and exhaled deeply . He released me at that point, looked up at me and smiled. I had an intense urge to kiss him again and pulling him up to me, put my lips to his and stuck my tongue in his mouth. I probed his mouth for the taste of my own semen in a state of post orgasmic bliss. It felt so slutty.

He continued the motion to standing, breaking off our kiss. Ginger lifted me up and said "I need a drink. How about you?"

"Yes, that sounds good, and I'm starving, Ginger. Cindy dropped me off here without dinner tonight."

"That sounds good to me too." He pulled a short silk dressing gown from the closet and handed it to me. I was still barefoot and half naked as I followed him to the kitchen. Ginger mixed up some whiskey and water for us, threw some breaded fish and frozen fries in the oven, set the timer and said "Let's get you dressed, shall we."

We returned to the dressing room and Ginger started picking through her lingerie drawers looking for something. He pulled out a wide garter belt with 6 suspenders and asked "How does that work for you with your white panties?"

"Do you have any stockings to go with it? I'm kind of short handed at the moment."

"Oh, of course. We owe you a pair anyway," and he dug out a new pair of white sheer hose to go with the garter belt and handed them to me. I fastened the garter belt and sat to slide the hose up as Ginger opened a closet door and started searching for something. The hose were high end and felt wonderful sliding up my smooth legs. I started to get a bit hard as I attached the hose to the garters, in spite of having cum just fifteen minutes before. Hose and garters felt so sexy and I had never worn white.

"What would you like to wear, Sweetie?"

"I thought skirt and heels like everyone else tonight, but what's that pink dress?" as I eyed a puffy ball of pink.

"Ooh, that will go good with white I think. Yes, a cute sissy dress. Let's see if it will fit you," and Ginger pulled out a frilly, lacy, wide skirted dress with a high waist. It was definitely not work attire. He held it up to me and it looked close, so I stepped into it and Ginger pulled it up, fitting my arms through the sleeves. It fit reasonably well and I was zipped into it. I looked at my reflection and thought I looked very much the sissy in it. I slipped my shoes on and was admiring myself, just as the oven timer sounded.

I put a wide napkin in the bodice of the dress and as we ate Ginger and I chatted about how our dressing first started. I was per-pubescent, he was early teens. Other typical stuff, how many girlfriends we had told, or boys we had experimented with. How we'd tried to find other's like us to meet with.

I had second thoughts about the sissy dress. "I don't think Cindy should see me in this. It's a little over the top, don't you think?"

"I love it. I'd keep you in it all the time if it were up to me, but yes, you're probably right. Let's find something else for you. White hose don't go well with much though. Definitely no little black dresses. Blue though, that might work."

Ginger freshened our drinks with two full shots and we returned to the dressing room. He found a light blue skirt that fit me with a dark blue synthetic blouse to go along with it. It would do as my fake tits looked nice in the blouse.

"Cindy brought you half dressed. No jewelry? Let's do a string of pearls, and some clip-ons."

"I can't do clip-ons. They pierced my ears tonight," and pulled my wig back to show Ginger a stud.

"Oh my, I wish I had mine pierced. I'm so jealous. Cheryl might have mine done after she sees that. Wow. You two are going all out."

"It was her idea, actually. I'm not to crazy about to tell you the truth."

"Oh but you'll be able to wear real earrings. It will be great, I think."

Ginger helped me with a single strand pearl necklace that hung just at the top button of the blouse. He reached my neck to adjust it and we came close to one another again. Another round of kissing and feeling each other up and down ensued. That was as far as we got with the jewelry.

Once we had broken off from that round of kissing, I asked him what size breast forms he wore as I had been feeling them pressing against me a few times now. He unbuttoned his blouse to show me his over bust cincher and boobs. I just kind of stared at his upper body, examining the cincher intensely with my eyes as I wondered what it would feel like on me. "Where did you get your corset," I asked.

"We custom ordered it from a TG shop. Standard foundations don't fit a guys hips you know. Waste of money really. Do you like it?" and he reached out and took my hand and brought it to his torso to feel him.

"Gawd yes. I need one like this," and I felt him, letting my hand wander over the cups, feeling the weight of his forms in them. It was a fabulous effect. As I did so, Ginger unzipped his skirt and let if fall to the floor. His large cock was apparent in his full cut black satin panties. I moved my hand lower and with my eyes locked there, caressed his large cock through the material. I quickly dropped to my knees and pulled his panties down, exposing it just inches from my face. It was circumcised and thick. It was a man's cock compared to mine and I marveled at how much bigger it was as I reached out to hold it. I'd never actually done this as an adult and touching him was a surreal feeling. An actual cock in my hand, large, and still getting larger.

I kissed it, reveling in the feeling of it against my lips. Where I was small and quick to achieve erection, Ginger seemed slow to become hard by comparison. I licked the head tentatively, then gaining confidence, took it in my mouth as Ginger encouraged me. It was soft and velvety, yet almost hard at the same time.

I started taking it as deep as I could in my mouth, but there was plenty to spare so I wrapped my hand around the base and softly squeezed it. I started bobbing up and down on it, attempting to emulate the technique Ginger had used on me. It was hard now and filling my mouth. I rubbed it against my tongue and brought it completely out of my mouth and looked at it up close. I saw a drop of pre-cum ooze out the large urethra and gave it a lick. Ginger seemed to like this.

"I need to sit down and enjoy this, Julie," and I got up and followed him to the love seat. He held his cock out for me and I resumed my efforts, sucking hard, then kissing it, cupping his large balls in his panties, squeezing the base and sucking again. I wanted to prove myself as a sissy cocksucker and doubled my efforts. I wanted Ginger to cum for me. I was beyond trying to understand why, I just did.

He seemed to really like it when I wrapped my lips around the head and sucked as I flicked it with my tongue. I felt him tense when I tried to open him with the tip of my tongue, as if I was licking a teeny little pussy slit. I'd suck, then lick and squeeze some and do it again. My jaw was starting to tire when he placed his hands on my head and started pushing. I struggled against a gag reflex and tried to grip it with my mouth to no avail. His cock head hit the back of my throat and he came. I gagged and choked as his ejaculate erupted. It was more difficult to take than I expected it to be and I struggled against his grip as more hot salty semen filled my mouth. It was incredibly intense for what seemed like longer than it was, and then it was over. I felt a little queasy, but I had done it. I found my drink as Ginger rested. I took a couple of large swallows of whiskey and water, washing it down. I knew at that point I would be doing this again.

I brought Ginger his drink and I sat with one butt cheek on the love seat next to him.

"Did I do good, you think?"

"Very good, yes. Did you enjoy yourself?"

"Honestly, swallowing cum wasn't the greatest for me. It was being able to make you cum that was the most intense part. The same as making a woman cum for me when I eat her pussy I guess, now that I've done it. It's being able to do that. I might want to get fucked some day too, and feel what that's like."

Ginger smiled, put his hand on the back of my neck to pull me in and kissed me. "I'd be gentle," he said as the kiss was short and sweet. I kissed him back and instinctively reached for his breast. It wasn't real, but I still had the impulse to grasp it. I let my hand fall down to his cinched waist as we kissed.