The Sissy Department Store Ch. 05

( Note to new readers of this series: This story is very sequential. It would be beneficial to the reader to start with chapter 1 to see if it suits your interests. Chapter 1 is a quick read )

The Sissy Department Store

Chapter 5

I awoke first the morning after our night with Kathy. I quietly got out of bed so as not to awaken Sandy. I started coffee and sat at the table leafing through the Christmas catalog while she slept in. I wore panties, as that's all I had now, and sweats and t-shirt. I sipped coffee and pondered the events of the last few days as I looked through the lingerie and women's shoe sections. As the coffee cleared my head, I became increasingly worried about the shaky ground I was on with Sandy. Breakfast in bed you idiot, and I whipped up an egg white omelet with toast and peach wedges and OJ. I fixed it on a tray and gently roused her while wafting the smell of breakfast over her.

"Um, that smells good. I gotta pee though. Take it out to the table, Lover," Sandy said.

I was still 'Lover' at least, I thought.

She came out to eat, having added the bottoms of the green satin sleeper. It was the first time I'd seen her wearing it in the daylight. It lit up her green eyes in a wonderful way. She started eating and leafing through the catalog as I sat across from her and semi-stared at her.

"What?," she looked up at me and said.

"Your eyes look so beautiful in that. They're so green in the daylight. You should wear that color more often."

She reached over and squeezed my hand. I might be a few moves behind on the relationship chess board but I wasn't totally clueless, I proudly thought to myself. I'd always loved her eyes ever since I first laid eyes on them in high school. She was extremely popular and I was a shy dweeb. We were assigned to be lab partners in jewelry class of our Senior year and I caught her on the rebound from a breakup with a 'big man on campus' type and never let go.

"Nice try," she said. "But you're not going to get off the hook with that 'beautiful eyes' stuff."

Damn, she was on to me. "Well they are, Babe. I love your eyes," I squeaked.

"Uh, huh. I'm surprised you didn't put your little maids outfit on to serve me breakfast. You really seemed to enjoy wearing it."

"Well, it's not mine to wear, and I, uh, I don't want to right now."

"Why's that."

"I'm not sure if you would like me to. I don't know if being Christina is what you want from me, and if it isn't, I won't do it anymore."

"Well that's nice, Babe. I appreciate that, but we both have to accept that that's a part of you. I read your books you know. I read some of the personal stories in one of them and I have to accept the fact that it will always be a part of you. I don't know if either one of us knows how big that part is just yet though."

"So what does that mean for us then?"

"We'll have to find out, I guess. For now, it means you're going to do everything I say and see if we can work this out between us. That's why I want to meet the person we borrowed the dress from and see how it works for them, or if it even does. You're not done with your punishment weekend either, you know."

"I'm sorry," I said.

"I know... That was good, thank you for breakfast. Now where were we? Oh, yea, punishment weekend. I'm going to get ready for my run while you clean up."

She came back into the kitchen dressed for a run and said, "You have a couple of turkey basters in your cooking stuff, right?"

"Yea, what do you want my turkey basters for?"

"Everything I say, remember? You're going to need to get used to that."

I went digging for basters.

"And if you think I don't, or won't, like it, you won't do it. I am your Queen now, your Princess and your new goal in life is to try and please me."

I realized I hadn't fully thought this through, as is so often the case. "You're my Princess. You always will be," I recited as I rummaged.

"Good. That means everything. We're in this rabbit hole together and I want to get us out of it somehow, if we can. I know I want out of it. And it's the little stuff too. No more farting in bed and thinking your funny. I hate that. No ogling other women in front of me. I hate that. You're new goal in life is to please me, make me happy, and think of me first. Do you think you can do that?"

She started her stretching routine. I loved watching her do her stretching routine.

"I'll try, Babe. I want to really try. Yes. I'm sorry about that stuff."

I found the basters in my kitchen tools. "What should I do with these, then?"

"While I'm out on my run you're going to freshen up by using them to clean yourself out."

"What? You mean you want me to give myself an enema, Princess?"

"You don't need to call me Princess. Just thinking of me as one is what I'm asking from you, and yes, that's exactly what I mean. Don't use more than a few drops of soap with warm water and get yourself all Palmolive fresh, rinse and repeat. Then you're going to pull the bulbs off them and put them on your nipples while you shave everywhere again. Squeeze all the air out and stick 'em on real good. I found your porn was full of helpful hints. If that doesn't work maybe we can get some snake bite kits."

"This sounds kinda weird, Babe. And then what would you like me to do?"

"That's funny coming from you. I want you to clean the toilet and rinse the tub real good. Then put on a pair of panties and your bra under your clothes. You're going to wear a bra all day to see how women feel in a bra all day. Change the sheets and do them with the clothes."

"But what about the bra I'm supposed to wear all day? I'll need to go down to the laundry."

"Don't stuff it and wear a jacket. It's cold outside. I'm going to run by my Mom's so I might be gone a while," and she was out the door.

I did as directed and cleaned myself out. I found it to be unpleasant and somewhat painful. Then I tried the bulbs on my nipples. They didn't stick real well and I had to keep pumping and sticking them. I did get some pretty good suction though, as they were quality utensils and I saw the effect it was having on my nipples. I found I liked this task, but wondered why she was having me do it. I ran some water in the tub and repeated the shaving I had done just a couple of days back. I was improving my technique in that regard and it was much easier this time. Shave down with the grain for cleanup said the hair remover bottle directions. I felt so smooth. I moisturized and used a little powder in my crotch and got dressed.

The bra felt amazing on my recently suctioned nipples. If this was punishment, I was all for it.

I wore a loose t-shirt and buttoned flannel shirt and managed to get the laundry going without any problem. It felt peculiar to be wearing a bra in public though, and my sensitive nipples rubbing in the cups provided frequent reminders that I was wearing a bra.

Sandy came in as I was setting the oven timer to go back for laundry. She carried a small brown paper bag that she immediately took to the bedroom.

"Hi, everything come out okay?" she teased.

"Yea, fine." I didn't know what that was about either, really, but I was afraid to ask.

"You smell nice. I kind of like that I think. I need to shower and shave myself today. You're going to come help me." She poured herself a tall glass of water, the sweat shining on her forehead.

"I am? Okay." This sounds like fun. Who doesn't like a soapy shaved woman. I wasn't getting the punishment aspect of this.

"How did the baster bulbs work," and she reached out and rubbed my left breast. I re-coiled a bit at the stimulation.

"Okay, I guess. They don't hold very well, so I had to keep doing it."

"Let me see."

I unbuttoned my top layer and raised the t-shirt and bra. She reached out and tweaked my left one. I re-coiled with a stab of pain."

"Mm, sensitive I see. Now you know how mine feel a little bit, so be more gentle with them from now on, unless I tell you otherwise."

She stripped and showered first, then ran a few inches of water in the tub and had me use a fresh razor on her legs. It was a piece of cake compared to doing myself and I was extra careful. Her toned, smooth legs felt absolutely wonderful. I kept trying to run my hands over her wet ass and sneak a feel between her legs and she kept pushing them away. "Stop that," she finally ordered. She rinsed off and wrapped her hair in a towel. I wanted to reach out and play with her perky tits so bad, but managed to restrain myself. "Another towel, please," and she put her perky tits under wraps.

"I think I need a trim today too, Babe. Get those good scissors out of my make-up bag."

She laid my used towel on the edge of the tub and I proceeded to trim her light golden pubic hair.

"Not to close, be careful, don't you dare finger me," she instructed, as she leaned back and monitored my efforts.

My cock was in pain from being denied a full erection. I kept reaching down and adjusting myself and she smirked at my discomfort. The bra cups rubbing my nipples added to the intense stimulation I was feeling.

The oven timer went off.

"Oh, better go load the dryer, Babe, before someone else takes them all,'" she remarked, as she pulled the shower curtain closed and turned the shower on; rinsing her now much more exposed pussy.

My dick was still trying to rise to erection and I tried to wish it away. I had to settle for putting a hand in my pants pocket and holding it to the side to leave the apartment.

When I returned, I set the oven timer to match the dryers. I found Sandy in the bathroom with a towel still wrapped around her as she dried her hair. She looked so hot. I wanted to lick and fuck that freshly trimmed pussy in the worst way.

She looked at me and smiled. "Lover, could you help me with my legs again?," she said, turning off the blow dryer and handing me the lotion. She sat on the edge of the tub and had me rub her legs down. My dick hurt as I worked the moisturizer in.

"This is nice," she said, as I worked. "I like you helping me like this. That feels good," as I worked some into the soles of her feet and between her toes. "I think it's making me horny, a little bit."

Now we're talking. I assumed my efforts were going to pay off for me. She headed for the bedroom, and I was just a step behind.

Sandy picked up the bag she had brought back from her run; reached in and pulled out a realistic pink dildo of about 6" in length. I was a little stunned.

"Be a dear and warm this up for me in the sink, would you, Lover," she said as she handed it to me.

"Where that did you get that from?" I said in disbelief.

"Oh, my sister and I had it stashed at home, so I ran by and picked it up. Do you like it?"

"I guess. I mean, I dunno."

"Hurry back. Wash it real good too," she said, shooing me to the bathroom. "I already changed the batteries."

I warmed it to what seemed like a good temperature and returned to find Sandy opening a lubed condom from her pre-birth control pill days. I held it out as she rolled the condom down the shaft. She undid the towel wrapped around her torso, leaned back and said "Do me."

I flipped the power switch on and was startled by the loud noise emanating from it. I placed my left hand on her inner thigh to hold her legs apart and started working the head over her exposed vaginal lips, spreading them open. Her trimmed pussy gave me a clear view. The tip entered her easily. I'd never used a dildo on her, or anyone before, so it was new to me. Sandy started coaching me, "Slower, yea, push it in a little more. That feels a little bigger than you, Babe. In and out now. Start slow. Yes, there it is," as I adjusted the angle. She reached down and started working her clearly visible clit in a circular motion.

She started moaning and a controlled humping as we both worked her slippery pussy. "I want your tongue in me," she cried out. I started to remove the dildo and she grabbed my hand and took it from me, "No, in my butt", and lifted her ass off the edge of the bed as high as she could to present it to me. "Make me cum. Make me cum," she grunted as I got down below her and spread her ass cheeks. I tongued her as well as I could from the positions we were in. Her juices had trickled down the crack of her ass and I licked them from her. I made a determined attempt to penetrate her anus with the tip of my tongue. "Yes. Yes," she cried out, all 'When Harry met Sally' like and erupted in a shaking orgasm. She pulled the dildo out and switched it off. She immediately brought her legs together.

I was happy with the results, but also disappointed that I was being left out of the fun.

"Umm, that was amazing," she finally said as she re-gained control and looked at me. "I think I like that. Go wash up and we'll do you now."

As soon as I entered the bathroom the oven timer went off.

"Can you go get those, Babe. I'm not dressed," she called out.

What is she doing, I wondered to myself as I retrieved the laundry. It was now plainly obvious what the enema and 'do you now' was leading up to. I hadn't planned for this turn of events, that's for sure.

Sandy was dressed when I returned with the laundry. After putting it away, she said, "Okay, your turn," and started undressing me. I helped her get me down to bra and panties and she pushed me onto the bed. "Be right back."

She returned from the bathroom with the dildo and started opening a new condom package.

"What are you doing, Sandy?"

"I'm going to fuck you with this, Babe," and she rolled the lubricated condom onto the dildo.

"You're not. I mean, you are?"

"Yea, Babe. Let's try it, just like in your books, you know. If you want to feel like a girl, you gotta get that cherry popped and today's the day, unless this won't be your first. This is your first, isn't it?"

"Yes, this will be a first all right. Trust me."

"Get on your back. I want to see your face."

I lay back and she worked the panties off of me with one hand, while waving the dildo around for effect with the other.

"Raise your legs to your chest. I'll be gentle. Try and relax," and I felt the cold moist dildo head probing for my anus. I had lost my erection for the first time in what seemed like hours. She found the spot and pressed it into me. "Relax now and let it come in. It's hard the first time, I know. She had a mean sense of humor lately, I noticed. She pressed it firmly against the entry and held it there, stroking my thigh. "Your little pee pee looks so cute all shaved and shrunk up like that. Where did that big hard-on go? Here, let's try this," and she switched the vibrator on.

That felt better. My cock started to stir. She maintained the pressure and I tried to relax my sphincter. She moved her free hand into a bra cup and started to gently rub my tender nipple. That felt incredibly good.

"I'm sorry, I forgot the foreplay. Maybe that will help."

It did, and I relaxed further as my cock responded to her nipple manipulation. She felt the resistance decreasing and pushed forward.

"Just relax and tell me to stop if I need to." She pushed it forward and penetrated me.

"Just get use to it there for a minute, Babe. You're not a virgin anymore though. It gets better after the first time. You'll see. You can play with your cock now, Baby. Go ahead. I want you to enjoy your first time," she said as she continuing working my tender nipple. "It's not in very far yet. I'm gonna push a little more now."

I felt the pressure and didn't think I was going to like this. It hurt as she moved it in further. She retracted just a bit, then pushed forward. The vibration inside my body was like nothing I'd ever felt before. My cock seemed to like it as my prostate responded to the stimulation.

"That's it, Lover. Relax and don't fight it," as she continued with the cliches.

She moved her hand to my other breast and gently twisted the nipple through the bra cup. That felt better. Great actually. I started working my cock faster. I tried to ignore the intruder inside me and focus on release.

"That's it. Make it squirt for me. I've never seen you squirt your juice like this. Show me how it squirts," and she pinched my nipple harder as she slowly worked the dildo back and forth. She had only inserted it a few inches. "Show me. This is so exciting to wait for your cum to shoot out. This is so cool, Lover. I want to see it shoot."

I worked my hand faster as she twisted my nipple. My balls tightened, my ass gripped the dildo and I came for her. The first shot nearly reached as far as my bra, followed by a few more in decreasing amounts. I was shaking and pulled her hand from my breast; stopping the post orgasmic over stimulation.

"Ooooohhh. Look at that. I'm impressed," and she slowly withdrew the dildo from my sore rectum. "I've never actually watched that, you know that? That's kind of crazy to see it happening."

"I'm glad you enjoyed the show."

I put my legs down on the bed and rested as she got up and dropped the dildo in the bathroom sink, returning with a towel and wiping the cum off my belly. "Oh, that was lots, sissy boy. Did I make you horny today?"

I grabbed her and pulled her to me on the bed. "A little bit, yea," I whispered in her ear as I hugged her tightly and rested.

"Did you like getting fucked, Babe?", Sandy asked.

"Not really, to be honest. We could skip that part next time, if it's okay with you. I liked the rest. Shaving you was just so hot. I wanted to fuck you so bad in the tub. I think you might have liked doing me with the dildo more than I did, actually."

"That's funny, now you know how we women feel sometimes."

We spent the rest of the day on domestic stuff. Sandy made me wear the bra all day like she said she would. It got uncomfortable, which she took great pleasure in knowing.

As we watched Sunday night TV we ran down the coming weeks schedule. It was going to be busy with Sandy's birthday on Wednesday, going out with friends Friday, etc..

The maids dress hung on my side of the closet, reminding me of it's presence daily.

On Tuesday, Sandy came home from a shift and said, "Don't make any plans for Saturday. We're going to a Halloween party with a few people from my store. I'm going as a cheerleader, and you're going as Christina, the sexy maid. Doesn't that sound great?"

"What? I can't do that."

"Why not? I think you look kinda cute as Christina. You look so sexy, Babe. I'm sure you can win best costume, if there's a contest anyway."

"One thing though, Babe. I think your B cup doesn't cut it for that dress. It doesn't fit right. It looks like it needs some big ones, so Kathy is going to help you find a bra with some D cups on Thursday. She works closing and is looking forward to helping you. Won't that be nice? Some big tits, just like you guys like 'em."

"I love your tits, Babe. There so firm and perky. They won't be getting all saggy and stuff when you get older, either." I was trying to get better at the compliments. "But, Kathy? I thought we were done with Kathy?"

"Yes, we are. I am anyway. We talked today and we agreed to be just friends. She's used to rejection, I guess. She said if I ever dump your ass to let her know though. She said my tight little butt will always be one of her fondest memories, so you better be good to me."

"It has my vote for the best butt in town, Hon."

We had her birthday party Wednesday and she was in a great mood. I made the cake. I got her the new compact cassette Walkman, which she seemed to really like. She put her green sleeper on when we got home. We'd been wearing our old stuff since the weekend at that point and hadn't had sex since Sunday. I took the green satin sleeper as a green light and stripped and jumped into bed with her.

"Aren't you going to put your baby doll on, Babe?," she asked, as I kissed and nibbled her ear.