The Sissy Department Store Ch. 01

Introduction: This is a short, first time submission drawn from my tastes and an older perspective. It reflects a cross dresser coming of age in a different time.

The Sissy Department Store

Chapter 1

"Go on, give it a kiss, Christina. You know you want to!"

I'm Christina, and that's my girlfriend, Sandy, telling me to kiss "Jamie's" hard cock as it protrudes from his lowered black satin panties. His cock is hard, yet soft to the touch, and my heart races as I hold it tentatively. I have never held a cock other than my own, and it is as exciting a moment as I can recall up to this point in my life.

"Come on now, don't be so shy, Christina," Kathy, my girlfriends co-worker and mentor chimes in. "Give it a big wet kiss already."

They both loved to call me Christina; always emphasizing the feminine connotation.

So there I was, on my nylon clad knees, holding a hard cock only inches from my made-up face. My pink nails contrasted sharply against Jamie's black satin panties as I hesitated to take this step into sissy-hood. A step once taken, I was afraid I may never step back from. I could see the bead of pre-cum moistening the slit of Jamie's hard 5 inch cock. I held His cinched waist with my other hand as I steadied myself, our powdered and perfumed bodies emitting intoxicating feminine scents. It was all so much to absorb. My heart pounded in my chest, further reminding me of the restriction created by the long-line Playtex bra I was wearing.

There had been many steps leading up to this biggest of steps. Steps which I had either been willing, forced, or cajoled into taking the past several months. My aching toes often reminded me that many of these steps are now taken in my new pair of red faux patent leather 3 inch pumps. I had now been educated to the fact that a feminine appearance wasn't all fun and games.

I whetted my painted lips. Up until recently, I didn't realize how sensuous wearing lipstick could be. I loved the smell and taste of it on my tongue. I pursed my lips and gave his cock head a gentle kiss. The salty taste of pre-cum rapidly reached my taste buds. I pulled back and saw the imprint of my lips on the head of Jamie's cock.

How, you might ask, had it come to this? Let me go back to the beginning.

This story begins in a different time. A time before the Internet and instant porn 24 hours a day. A time when LGBTQ was just a bunch of random capital letters. Where a "men's" magazine from your friends older brothers basement bedroom was a treasure trove of female beauty, inspiring wonder and awe. That was the good stuff back then.

Lacking the good stuff, one could make do with a department store catalog and its lingerie section. Perhaps my interest in feminine clothing was rooted there? Whatever the reason, it became my thing and the intensity only burned hotter as I came of age.

My high school sweetheart, Sandy, and I began living together shortly after graduating high school. It was a cheap one bedroom apartment, but it was freedom. We thought we were in love.

Sandy found retail sales work at the local mall department store as I started a Community College program in Culinary Arts. I supported myself, and Sandy partially, on an insurance trust fund created after losing both of my parents in a traffic accident. This allowed me to focus solely on school. Well school and jerking off a lot in Sandy's absence. I also took on most meal preparations due to my career choice. My Mother had been an excellent cook and I often helped in the kitchen in my youth, leading to culinary school.

With so much free time I began sneaking Sandy's underwear out of her side of the dresser and masturbating in them while perusing old porn magazines. The lingerie the models wore often excited me as much as the female flesh, oftentimes more.

Sandy's clothes didn't quite fit me, but that didn't stop me. She had been on the track team and had a wonderfully toned body, but her being 120 pounds and a few inches shorter than I, her things didn't quite fit my still slim 160 pound frame.

I had begun purchasing the X-rated "reader letters" magazines of the day, as I noticed they occasionally printed submissions related to cross dressing/transvestism topics. The first one of these that caught my eye at the convenience store had a cover teaser something like "When He Becomes She" It was the October edition and I read the article and reader letters regarding transvestism repeatedly. That's when I saw it in the side bar of come-on advertisements. An ad for "Lee's Mardi' Gras Boutique" in NYC. An emporium for cross dressers and female impersonators said the small ad. What would such a place be like in far off New York City? Write to us for our news-letter said the ad.

Intrigued, I sent off for the news-letter and waited. Finally, a nondescript envelope arrived from New York. Inside I found a folded photo-copied multi-page mailer full of cross dressing and drag magazines, French maids uniforms, fetish shoes and beard covering makeup, etc.. I was astounded at the array of products and publications. I jerked myself raw just perusing the mailer.

I had to see more, so I carefully selected a few magazines, with titles such as "Men in Skirts - #17" and "Sissified Males Digest - #8" and sent off the money order with my selections. For those younger readers not familiar with this type of publication, they were single folded, saddle-stapled novellas of sorts and are now highly collectible. Vintage copies found online these days can be rather expensive. They usually carried cover illustrations of feminized men in skimpy lingerie, often wearing corsets or cinchers and ridiculously high stilettos. Of course, the cover art frequently depicted dominating females similarly attired and with exaggerated figures and sporting expansive breasts with large protruding nipples.

The other thing about the fiction booklets is they were much cheaper than the glossy 4-color print magazines offered, featuring female impersonators and the like.

Careful to control the Mailbox key at our apartment, I anxiously awaited their arrival. What arrived was more than I could have imagined. My selections featured sissified, humiliated males, subjected to feminization by domineering women. The stories revealed things I hadn't imagined. Feminized men forced to serve as French maids. Taken to beauty salons for makeovers. Forced to service women, and sometimes men sexually, etc..

After their arrival, I would dig in Sandy's drawers every chance I could and jerk off as I read my coveted reading material. Caressing myself in her lingerie, I Imagined I was a feminized and sexy sissy pet to my girlfriend, or to others. This always lead to explosive orgasms. I was hooked, and soon ordered a few more of these exciting publications.

I tried to be discrete about using Sandy's clothes, but later learned I had quickly grown careless. Unbeknownst to me, Sandy had found my tell-tale cum stains on one of her slips. I had quickly learned to love the cold electric chill of a nylon half-slip over my hard panty encased cock. Sandy had also noticed other things like pantyhose missing, as I had clumsily ruined a pair and had no easy way of replacing them.

As I would later learn, Sandy had confided in Kathy, an older female co-worker, about her discovery while the two of them took a break together later that same day.

It was just the two of them in the department store break-room.

"What's the matter, hon? You look a little down today." Kathy asked.

"Yea, you could say that. I discovered my boyfriend is a perv today. He's been in my clothes," Sandy confided. "I can't believe it. It's so disgusting."

"In your clothes? How do you mean "in your clothes" Sweetie," Kathy replied with one eye brow cocked. She usually called everyone Sweetie or Sweetheart. Kathy had been at the store for about 10 years after failing to achieve a university degree. She had transitioned to a career sales clerk and enjoyed chatting with the new girls starting out on the sales floor. Being a "flower child" from the tail end of the hippie age, she usually hit it off with the younger girls.

"I think he's been wearing them. I know for a fact he's been playing with himself with them. The slip I wanted to wear today had his jizz on it; that I'm sure of, and some of my other things have seemed stretched out lately. I thought my bra clasp broke in the laundry, but now I'm pretty sure it was him," Sandy said with a disgusted look.

Kathy gave a knowing nod. "So he's one of those is he? It seems as if they're coming out of the woodwork since they started the midnight showings of "The Rocky Horror Picture Show" at the theater downtown."

"The Rocky Horror Picture Show - That transvestite movie!" This was all so new and unsettling to a young woman of 19. "You see a lot of them upstairs?"

"Oh my, Sweetie, if you've seen as much as I have working in Women's wear and lingerie, you'd think half the men in town wear panties. Well, not that many, but it's more common than you might guess." stated Kathy with another firm nod of the head.

"Really? Men come in here buying female underwear for themselves a lot?" Sandy replied, still upset at her discovery and yet intrigued by what Kathy was telling her.

"Oh sure, they think they're being sly about it, but I can tell 'em a mile away anymore. I call it "the look"... Looking at the foundations out of the corner of their eye as they paw at the pajamas. Pretending their shopping for the wife or girlfriend. They are usually nervous as cats and say silly things like "she's about my size, I think" when I offer assistance. I have a few regulars that are pretty open about it and I treat them like any of my customers. I don't mind really. Some of them rack up pretty good sales. The young ones can be so cute sometimes, with their flushed cheeks and all."

"But they're fags though, right? I mean any guy wearing women's underwear has got to be a fairy, don't ya' think?" said Sandy. This was all so confusing to her.

"Well, not necessarily, Sweetie. Like I said, a lot of them are wearing wedding rings, and I even know some of their wives..., and they're not the same size, either." Kathy said with a laugh. "There is even a couple that come in once in a while and it's obvious who they're really shopping for. You know what they say - she wears the pants in the family. Sometimes they really mean it."

Sandy was really confused now. "So I should dump his ass though, right? I mean I didn't have any idea about this. I definitely don't like finding his jizz on my clothes, or having them all stretched out and ruined. I'm gonna let him know I know what he's been up to and put a stop to that at least."

"Well of course you'll need to do that, Sweetie," Kathy replied. "But you might want to do a little investigating first and see what else you can find...just for fun maybe? It's my guess he's got a secret stash of clothes, or porn, or who knows what. I know there are a lot of men in this town that do. He is kind of cute from what I've seen of him, and you seemed to be happy with him otherwise, right? You could just play him for a while to get even maybe?"

"Oh yea" said Sandy. "He's a great cook. He's going to school for it you know. He's pretty tidy and helps me keep the apartment up. Oh my God, why didn't I see all of this? Yup, I'm pretty sure he's a homo all right, but I'll do that. I'll see what else I can find the little perv's been up to after he leaves for school tomorrow morning."

Sandy quickly found the stash in the back of the closet the next morning, in an old gym bag of all places. She couldn't believe what she was seeing. Besides the common convenience store porn, there were these other paperbacks with odd titles. Men in Skirts! Sissified Male Digest! What the fuck is this? And my pantyhose. That's what happened to them. Oh, and there's my lip gloss that's been missing, too.

The Lee's Mardi Gras Boutique mailer was also there, as well as a couple of money order receipts. One of the receipts was just a few days back. It occurred to her that he must have ordered more of these things. She didn't see anything to tell her what it might be.

Sandy sat down and browsed the few magazines. How bizarre, she thought. Feminized men forced to service women in the frilliest of female clothing. The concept of feminized sissy males had never occurred to her before. After scanning through the pages it became apparent that control of the males sexual releases and submission to women was a consistent theme in the stories and illustrations. Worship of the women while attending to their sexual needs was a constant as well. That she could get used to, she thought. Sandy found herself getting moist while reading an excerpt of an extended pussy eating training session. But no! This is disgusting...

As Sandy showered for work, her fingers found their way to her pussy. Chris hadn't been attending to her needs lately, and now she new why. The thought of sitting on his face and training him to eat her pussy the way she had just read about had her aroused. She brought herself to a shaking orgasm as the warm water pelted her.

I'm gonna teach that little perv she thought, as she finished preparing for work.

"Well, you were right. He's a total perv...Totally! You won't believe what I found," Sandy whispered to Kathy as soon as she found her on the sales floor at the start of her shift.

"Oh, something interesting, Sweetie? Do tell." Kathy was proud of herself as her hunch had proven correct.