The Sissy Department Store Ch. 05

"No thanks," I whispered. "I still wonder what it would feel like if we were both in satin though."

I took it slow, as I had been shown by Kathy, of all people, making sure I brought her to a quivering orgasm with my tongue first. She pulled me up, grabbed me by the cock and half grunted under her breath, "fuck me". I was happy to oblige and pounded her juicy pussy until I exploded inside her. We fell asleep in each others arms just the way we always had before.

The next day was my first return to the store in a week. I arrived around 8:15 to make sure there wouldn't be much time available with Kathy. She was helping another customer so I pretended I was looking for pajamas for my girlfriend. She'd seen it a thousand times, and smiled in my direction as she finished up.

"Christopher, it's so nice to see you again. How are you, Sweetie?"

"I'm good. Nice to see you too."

"Sandy tells me I'll be seeing Christina again Saturday, too. I can't wait."

"She did. You're going to the party?"

"Of course. I wouldn't miss it for the world. I hear your going with jumbo size. You know how I feel about that, but you do need to fill out that cute dress, don't you."

We stepped over to the bra and foundations racks and she pulled out a black, long line support bra. "38-D, that'll hold some big boobs I think." She held it up to my chest to size it up on me. It had full padded cups with lace overlay and intricate embroidery all over the Lycra-spandex that extended about 4" below the cups. I liked it. The more spandex and lace the better, I thought.

"That should be okay, I guess." I saw a guy in men's wear watching us from over Kathy's shoulder. My stomach did somersaults. That guys watching us, Kathy."

"Oh, don't worry about him. He's probably just jealous. You should get a nice chemise too, Hon. It will make the outfit, and you know how us girls like to feel good underneath."

She picked one out that would probably hit me just below my butt cheeks in thin black satin, again holding it up to size me. I could feel myself blushing, but the satin looked like it would feel great. Sold. I paid in cash as an older female waited in line behind me, making me nervous. Kathy acted like it was a typical transaction with a "See you, Saturday, Sweetie", and I made my way home.

Sandy seemed pleased with the choices as she examined them. "This feels nice," she said, as she admired the chemise. You could sleep in this, maybe.

We went out Friday night to the local beer joint for Sandy's second birthday party, with friends this time. The drinking age would soon be raised to 21 and it was a crowded Friday night. I had to try and use the stalls as I was still without male underwear, but managed to get by. I drank too much, Sandy had to drive us home and I threw up shortly thereafter. She went to bed as I hugged the toilet. It wasn't the first time.

She had her fun with me Saturday morning. "Am I being too loud? You'd better drink some water, you have a big day today."

Sandy showered and got dressed as I recovered. After a light brunch, Sandy said "We need to bring something to the party tonight, Babe. How about your artichoke dip? Everyone loves that."

On our way to the store, Sandy loudly said "Pull in here" as we passed the Rex-all drug.

"Run in and get some pink nail polish to match your dress, Babe. You're going all out tonight, and a bottle of remover, and a package of big water balloons, too."

I was becoming accustomed to embarrassment and the guise of Halloween the next day, so I picked out the items as instructed without any issues.

We arrived back at the apartment after noon.

Once we had put the groceries away, Sandy looked at the water balloons. "I threw some gelatin in the cart today. Can you fill these with gelatin? I read where someone made jello-mold falsies in one of those books of yours. Sounds yummy."

I mixed up a couple of boxes and measured out equal amounts and filled two of the heavy balloons using one of the basters I retrieved from the bathroom trash. Sandy thought they would work fine.

"Time to get girly, Babe," Sandy said. "In the shower and shave real good. You know the drill. Lot's of Lavender, too." She helped with some hard to reach spots as I soaked in the tub. She plucked a few of my eyebrows that were bothering her and I got out and dried off.

"I'm going to have to go out like this, Sandy," I said. I had known this of course, but it was now getting close to becoming very real.

"Yea, you're taking your costume pretty seriously, that's for sure."

"I don't know if I want to do that. I'm not sure I can."

"Of course you can, it's Halloween," she said dismissively.

Sandy had placed everything out on the bed. She had chosen a garter belt and pink panties, sheer hose, the new bra and chemise for me. The dress was still hanging up. Once again, the feeling of such feminine attire on my smooth skin was terribly exciting for me. Sandy threw on a cheerleader's outfit, with an extremely short skirt and tank top before I was halfway dressed. She looked very sexy. She warmed up my new tits in the sink as I finished working the lingerie on. Once the bra was on, she helped me insert the balloons. It was a strange feeling having so much weight on my chest, but the results were better than I had expected. I had tits. Big tits. Yes, I loved them. Sandy helped me slide the chemise over my head and fit it over my body. It felt wonderful. I couldn't deny myself that.

She helped me get into the dress, as well. I filled it out much better with my new bust size and we were both pleased with the results.

"What about make-up, Sandy?," in realization that we had skipped a very important step.

"We're going to do that later. Let's do your nails now."

She painted my nails for me in order to get it done without making a mess of things. She rarely wore polish herself, but was quick about it regardless.

"You blow on those while I pack up," so I sat there looking at the strange appearance of my painted nails. I was thinking this was way past going too far. I just liked the feeling of Sandy's underwear, didn't I?

She went to the bedroom and got my skirt and blouse, and the shoes that needed to be returned to their owner. She also brought my own black heels out and slid them on my feet as she didn't want me to ruin my nails.

"You sure are high maintenance," she joked. "Practice some more in those. You gotta walk the walk, you know."

I walked around the apartment, re-acquainting myself with the feeling of being on what felt like stilts to me.

After a few minutes of heel practice, she brought me into the bathroom and sat me down on the toilet and stretched an elastic choker over my head and around my neck. It had been hers from the 70's choker fad. I could see why it was only a fad as it was quite distracting on my neck. She placed the wig on me and brushed it out to frame my face as best she could and said "Finished".

"Finished?" We're not finished. I don't have any make-up on."

"I have a big surprise for you, Babe. You're getting it professionally done."

"You can't be serious, Sandy. Where am I going to do that? Do you tell everyone about me?"

"No, silly. So, she's not a professional yet, but you remember my friend Cheryl, that went into the Cosmetology program at your school. I asked her to do it for us. She said she'd love to. And your not her first boy either, she told me. I keep learning your not the only guy into this. She's not licensed, but she's gonna do your make-up for you at her place. It's time to get going."

"So you told her it's just for Halloween, right? I see her at school sometimes."

"Yea sure, Babe."

Sandy threw my wallet in and old purse of hers.

We packed up the clothes and dip and picked out the only coat I had that would cover me. It was black wool and only half way covered the skirt of my dress. Sandy wore her old powder blue Goose Down stadium coat as it was cold outside and she wasn't wearing much else.

"Don't forget your purse," she said, as we prepared to leave.

"You better drive," I said. "I can't drive in heels."

I was shaking with nerves as we stepped out the door of our ground level apartment. I'd never been more thankful that there weren't stairs for me to navigate as I was still very much a novice in high heels. The cold hit my nylon covered legs and ran up under the skirt of my dress, chilling me instantly. I walked to the car as quickly as I could. My fake tits bounced around on my chest in a funny sort of way, but we didn't run into any neighbors, thankfully. Sandy seemed to be taking her time unlocking the car, but it was my nerves, I'm sure. I kept my head down as I waited.

I thought everyone was looking at us as we drove and kept my eyes forward at all times. We drove through the drive-through for burgers and ate in the car. My heavy tits got in the way as I ate, reminding me of there presence constantly. I sort of had to reach around them to put food in my mouth. Big tits were a pain, I was beginning to learn.

The B cups were so much easier to deal with.

We headed for Cheryl's.

We pulled up at the address in a neighborhood of post war cracker box homes Cheryl shared with one of her classmates. I'd seen Cheryl on campus now and then, so my secret wasn't going to stay here tonight. It's just Halloween, I said to myself.

"Don't forget your purse," Sandy said, as we got out of the car.

"Hi, come in. How are you guys? We should get together sometime... We're going to do you over here at the table. Take your coats off."

The house smelled like a beauty parlor and there was all sorts of make-up and wigs on Styrofoam heads and tools of the trade scattered about. It was quite expensive to be a cosmetologist it appeared.

"Oh, my. You look so cute in that!" Cheryl cried out, as she took in my appearance. "How did you do all of this? I haven't seen a choker in years. I'm going to be able to make you look so hot, Chris. Not bad bones to work with, for a guy anyway. I love that cheerleader outfit, Sandy. Go Tigers!"

Cheryl went on about this and that. She was a real chatter box. I didn't have to say a word and couldn't slip one in anyway, as she sat me at the kitchen table. I was happy with that.

"I need a before and after picture for my class portfolio. Is that okay?", and she took my picture. She set out a bright vanity light and started in on me. She removed the cheap wig, placed a towel around my neck, and went to work. She wanted to do my brows, but Sandy and I both said no, so she did just a little bit of shaping and said she would cover them as best she could. The little she did hurt like hell. She applied some spirit gum to my forehead to lift them and continued on.

Sandy and Cheryl chatted throughout the process about what she was doing to me, how I looked, old classmates, and on and on. For me it was like a trip to the dentist and I didn't say much. I couldn't read Sandy's face on how I might be looking.

Concealer, foundation, blush it went on and on. It was quite a process. Especially the false eye lashes and eye make-up. There was a lot of close your eye, open your eye, look up, look down, etc.. Finally my lips. She went on about lip liner and making them fuller, but not to full, it looks bad, yadda, yadda. I needed to pee, but they wouldn't let me see myself until she was finished. "You're going to have to wait. No peeking in the bathroom mirror."

"You know, I have a Jaclyn Smith wig I'm supposed to be working on for next week. Would you like to borrow it for tonight?, you can bring it back tomorrow," and she ran over and picked up a gorgeous head of brown hair from the shelf. My cock stirred for the first time since we entered her home. I thought I'd look hot in it. Jaclyn was one of my pubescent favorites after all, and still was.

She placed the wig on me and brushed it out over my forehead and around my face.

Sandy finally said, "You're making me jealous, Babe. You're going to love this. No dark alleys for you tonight."

"I need a picture," and Cheryl took a few shots at various angles. She finally handed me a mirror.

I was shocked. I didn't look like me. I was still a guy, but in bad light I could have fooled some people. I looked beautiful. It was an incredible feeling to see myself this way.

"I can't believe what you did. This is amazing. Thank you, so much, Cheryl. You get an 'A' from me."

I think I may have revealed this was about more than Halloween for me, which she had probably already guessed.

She reached out and squeezed my hand. "You're welcome. I'm glad you like it."

"I need to use the bathroom." I kept stealing looks of myself in the mirror as I got ready to piss. I tossed my hair, stuck my chest out, turned my shoulder. I couldn't get over how I looked. I realized I better pee sitting down in case I missed looking over my tits.

Sandy had her coat on when I came out of the bathroom, and was holding mine. "I cleaned out your wallet, Babe. You need to pay the stylist, you know."

"Sure thing," I said, trying to use a more delicate voice. I realized how feminine I now appeared.

Cheryl hugged me, saying "Have fun at the party." It felt weird being hugged.

"Thank you," I said, as I put my coat on and headed for the door. Sandy handed me my purse.

I still felt terribly self conscious outdoors, but felt better not looking like a guy so much. I tried to walk naturally in the heels. It was a work in progress.

As we drove to Linda's house, having learned of our final destination, Sandy asked me how I felt.

"It's hard to describe, really. I feel beautiful. Thank you for doing that for me. I never dreamed of actually looking like this."

"Are you sure, Babe?", Sandy asked.

"Oh, yea. I see your point. I guess I kinda did dream of this sometimes. You know me to well now, I guess. Thank you, though, really."

We arrived at Linda and James house. It was located in a newer subdivision of large, expensive homes. I saw that Kathy's car was already parked in front of the double car garage. That gave me anxiety. Sandy parked beside hers.

We knocked on the door and Kathy, in an Elvira costume, greeted us. Her prominent cleavage greeted us, to be more precise. "Hi, welcome, come in. I can't believe this! You look amazing, Chris..."

"Christina," Sandy said.

"Christina, of course. Let me take that" as she took the dip dish from me. "Take off your coats. There's hooks behind the door. Oh, wow. Jamie's going to be jealous," as she took in my appearance. "Aren't you the cutest cheerleader" she said to Sandy. "Did you do all of this? That's really incredible."

"We had help, actually. I can't even do that to myself. A cosmologist friend of mine helped us out."

"She does nice work. Jamie is going to want her number I think. Follow me, the party's in the family room." We followed her through the kitchen, as she set the dish on the counter along the way. The kitchen led to the large sunken family room, where Kathy, her date, and Jamie sat watching us come in. I recognized Rumors was playing on the stereo.

There was quite a fuss of "You two look yummy. The boys are gonna wanna to get into your panties," and such.

Jamie got up, dressed in a classic black satin fetish French maids uniform with a flaring skirt, white apron, and 4" black heels, big tits and a platinum blonde wig. He looked very sexy, I thought. I saw why I needed to wear the big tits to fill his dress, as his were very pronounced. He was obviously more comfortable in heels than I was, as he displayed a practiced feminine wiggle as he approached. Jamie was reasonably feminine in his facial appearance and wore a lot of make-up. He was quite tall in his heels and had a couple of inches on me, at least. He towered over Sandy.

"It's so nice to meet you, both. I've heard so much about you. Thank you for coming. You both look amazing. Aren't you just the cutest couple. Linda and Kathy told me you were a beauty," he said to Sandy, extending his manicured hand. "They didn't lie. Aren't you a lucky boy," he said in my direction. This was all said in a feminine sort of funny way. I smelled weed, make-up and perfume over my own. "And, Christina, is it? You look absolutely fabulous. I'm so jealous. Who does your make-up?"

"Told you," Linda said, bursting out laughing.

"Thank you. It's so nice to meet you, as well," I tried to say in a demure voice. The voice was going to be tough for me, I knew. "Sandy's friend did my make-over. I'm very happy with it."

"Sandy's friend. So, does she do girls like us often then? I'd love that, wouldn't I, Dear?"

"I'm sure you would," Linda replied.

"Where are my manors," Jamie said. "I'm just so distracted, I guess." Jamie and Linda led us across the room to where Kathy and her date were seated on the large sectional. An expensive looking pool table took up the end of the room.

"Sandy and Christina, this is Susan, and you know Kathy of course." Susan extender her hand to shake ours. Susan was about Kathy's size and was wearing a kitty kat costume with the end of her nose colored black and whiskers painted on her cheeks. Kathy wore a meter maid type outfit, complete with badge on her jacket. They were both in evening type make-up.

We exchanged pleasantries and they repeated extravagant compliments.

"Sit down, sit down," Jamie said, motioning to the couch next to Kathy. "What can I get you two. Beer, wine, a wine cooler perhaps?" I went with a beer and Sandy a cooler. Jamie swished his way to the kitchen with exaggerated effect, quickly returning with drinks and sitting opposite us, with Linda. He sat very stiff and upright and was obviously cinched very tight at the waist. His legs were long and he crossed them gracefully.

"Tell us about your make-over, Christina. I want details."

Sandy helped me tell the story of the make-over while Linda rolled a couple of joints from the stash box. Rumors, side 2 ended and Jamie got up to make a new selection. "What sounds good for you guys. Wait, I got it," and he put Boston's debut album on and we passed a couple of joints around. I began to get comfortable as "Foreplay" played. It was old, but fit the room.

We did the usual chit chat, how did you two meet, etc..

"I hear you're studying to be a Chef, Linda," said. "Is that your dip, then?"

"Yes, it is."

"Jamie, can you two girls get it warming, please," Linda asked Jamie.

"Of course. Follow me, Hon." Jamie got up and extended his hand to help me up. I was thankful for the assistance. "Give Christina a tour of the house too, Dear." I followed Jamie, unable to match his gate.

We set the oven on pre-heat and Jamie led me around their impressive home. "And this is Jamie's room. Linda calls it my play room, as we entered a back bedroom. "I keep Jamie in here." It was femininely decorated with lots of pink and an expansive make-up desk. The closet was quite full of clothes and heels lining the floor.

I admired the corsets and shoes. Well, everything. It was impressive.

"Your quite the lucky guy, you know that right?", Jamie said, as I marveled at his play room.

"Yes, I am I think," I said.

"No, you don't understand if you just 'think' your lucky. She's a beautiful girl and she's playing along with you on this. Your more than lucky, Chris. You hit the cross dresser lottery. Don't ever forget that. You have no idea how rare a find someone like Linda is for someone like me, or you. Most cross dressers would be happy if the women in their life just tolerated some pantie wearing, let alone anything like this. You have no idea."

I tried to agree with him, but that didn't stop him from continuing the lecture. He was most emphatic on a few points - Never forget they're a woman, we're not. Never, ever, cheat on her. Don't go any further with it than she's comfortable with. Worship her. Be a man for her when she needs one.