The Sissy Department Store Ch. 06

(For previous readers of this series, I intended to end it on Chapter 5, but felt it lacked sufficient closure. To be more accurate, this whole exercise has been a random, by the seat of my panties, serial piece. I am not a writer, but enjoy the distraction the effort provides for me. My grandest hope is that by reading my work, your mind wanders to your own fanciful memories of your first pair of high heels, your first real lover, etc..

If you've come this far, the above is probably apparent at this point. That being the case, if you would like to suggest a theme or progression for this cast of characters, please reach out to me. We'll see what happens. Thank you for your time.

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 6

As I sat at the table in our small apartment, spent pink-hued cotton balls and nail polish remover spread out before me, I reflected on the past few weeks. My cock stirred in my cotton panties as I flipped through the memories. Though there had been several significant events, the few that kept coming to the fore of the mental Rolodex were Jamie's cock in my mouth, seeing Jamie in his maids outfit for the first time, and sucking my cum from Sandy's pussy last night.

This last item may be taking precedence as I still felt a slight stuffiness in my nose from the experience. I had cum buggers, if you will. I had experienced her face-fucking me in the past, but it paled in comparison to last night. After hours and hours of stimulation through-out the day, I had cum quickly after entering her. She said "uh, uh, uh, you know what that means," and pushed me down to her wet sticky mess in order to finish the job. She must have been feeling over-stimulated from the day's events as well, as she grabbed me by the sides of my head and forcefully pressed my face into her.

She showed surprising strength when she was in such moods. If you now said to me a woman couldn't fuck something, I will argue the point vehemently. I was still trying to expel the results of the event. She fucked my face with a passion I don't recall her ever displaying, and we'd had some crazy sex lately. If she had verbalized anything, I don't know what it might have been. I wish I did. My hearing was cut off by her strong thighs gripping my head as her hands on the back of my head pressed me into her bucking torso. Her pussy was hot and juicy from our co-mingled bodily fluids and she squeezed them into my face with abandon. I didn't lick them from her, or suck them from her, she forced them into me.

She did say "That's some big cock Jamie has, isn't it?" as we settled into bed last night. I thought it was just teasing on her part, but I did find her very wet and ready to go as soon as I tested the waters.

Oh. It was Jamie's huge cock! She was right up close and personal with it herself. She wanted what I was having. That's what had made her so horny. It must have been. She had never let on that she was the kind of woman that found a huge penis desirable, but that's not something women usually shared with their boyfriends, now was it. Maybe she didn't know herself up until that point. Linda was more than forthcoming on her attachment to it, that was for sure. Damn, I had opened Pandora's box in the way of Jamie's panties, and found it had a huge dick inside. Was it in fact a problem? So many questions lately.

And she seemed to like the dildo, which she did say felt larger than me. Maybe I should keep my eye on it in order to confirm or alleviate my suspicion.

I wondered if Sandy's thinking Linda might invite her to have a crack at Jamie. Linda let me, after all. But that's different, isn't it? Or would it be like a guy offering his buddy to drive his car? You want to drive it? Just around the block to feel this V-8 get up and go. But she had that tight sweet pussy. She couldn't possibly want something that big stretching her out, or does she? I know she could make me feel her pussy squeeze my cock when she bore down on it. Imagine what she could do with something twice my size to work with.

As I considered this, I concocted a mental image of Sandy naked and straddling Jamie's cock as I held it in my hand, lining it up for her. Her back arched and her chest projecting outward. Her hard pointy nipples extended little buttons. Jamie is on his back wearing his black satin French maids outfit with the skirt flipped up to show his little heart shaved pubic patch and his large ball sack encased in black satin panties down below. A trail of oozing pre-cum runs down from the urethra as I grip him. My hand just barely wraps around the shaft and I see my pink nails reflecting the light. I help spread her pussy lips apart with my other hand. She slowly impales herself on it and I see her outer lips spread wide and the head disappear inside of her. Her scent wafts towards me as her juices run down the thick shaft and over my fingers. I release his cock as she lowers herself and my hand is pushed away. I put my fingers to my lipstick coated lips...

I was brought out of my mental exercise when I heard Sandy stirring in the bathroom. I wiped the nail I was cleaning to free my hand to push my hard cock to the side and tuck it down in my panties. My eyes were bleary and sore from scrubbing off make-up from last night and I was finding it hard to focus anyway. I was happy to take my eyes off the task to greet her as she came into the main room.

"Morning Lover, sleep good?" she said in a morning after sort of raspy whisper and kissed me on the forehead as she went for the coffee pot. She had quite the bedroom hair and was wearing a flannel pajama set. We had made a mess of her now well used satin sleeper. My new chemise wasn't new any longer either, but it was worth all of that. We both needed a shower.

"I was out like a light. That was a long day," I replied casually, attempting to hide my aroused state.

"Yes it was. How's it going? Nail polish is a pain, isn't it. Now you see why I don't bother with it."

"That it is, and the remover is making me nauseous."

"God, I'm tired. I wish I didn't have to go to work today... You know I meant what I said last night; about wanting to get out of that store, I mean."

How did women change gears like that, I wondered. The last thing I was going to be thinking about from last night was the fact that she wants to find a new job. I was imagining myself help her get her pussy stuffed with an 8" cock.

"Yea, I know. You should do it, I think. Doesn't seem like a bright future spending your life there with a bunch of old ladies."

"Would you run down to the corner and grab us the Sunday paper then, Babe? I want to check the help wanted ads. Denise told me that gym wanted to be open by New Years and they might be advertising for jobs already."

"Sure. It looks like I'm all finished up. Do you see any?" as I held my fingers up for inspection.

"Looks good. No more pink that I can see."

I changed into street clothes and headed for the door. "Sandy, where's my wallet at?... Oh, no. Did you grab my purse for me?"

"No, I thought you had it. You didn't leave it at Linda's did you? You did. Shit! Oh well, I'll have Linda bring it in with her. She said she had the Sunday shift with me today."

Yes, I did know that. I had heard them talking about it last night as a matter of fact.

"That won't work. I need to drop that wig off to Cheryl's this morning. I don't want to be driving all over town without my wallet and I don't want Cheryl waiting on me. We don't want to be assholes. She said it was for a school project."

That's a nice thick layer of bullshit. I impressed myself.

"I'll call her." Sandy looked up the number and Linda picked up. "Hi Linda. Hey, can you check on the hook behind your door for Chris' purse? It is. Yea, I know. Rookie mistake." Sandy covered the receiver and confirmed what I already new... "Yea, he needs it today. Uh huh. So James will be expecting him, around... 10:30", looking at me to confirm. "Thank you. See you soon."

"I guess your not used to carrying a purse, huh. James will have it for you."

James will have it, or will it be Jamie cleaning up after the party. Sandy was looking at me as she considered my reaction. Her expression told me she knew that I was thinking more about James and less about the purse.

"I bet you didn't think you'd be seeing him so soon. That might be a little awkward, Babe."

"No, I didn't. Damn. Yea, I'll just be quick about it. Now I know what it feels like to be a slut," I tried to joke.

"You were just a little slutty, but that's going to be interesting for the both of you, I bet. Such is the price for being a slut. Can you get me the paper? Just grab some change out of the jar."

There's that shifting gears without using the clutch again. Damn, how does she do that.

I ran down and got a paper. Sandy showered and dressed as I made us breakfast. We shared the paper over breakfast and Sandy looked through the want-ads as she ate.

She thanked me for breakfast and finished getting ready for work. I wondered if she was suspicious of the whole forgetting the purse thing as I cleaned up.

"I gotta run, Lover. You remember where Cheryl's was, right?"

"Oh yea. What do you think I should do about the dress? I think I should take it back when I pick up my wallet. It must have been expensive."

"You probably should offer it back at least. It does look pricey and Linda wasn't in a decision making condition when she told you to keep it. Okay, gotta run. Don't do anything I wouldn't do," and she gave me a quick kiss and hurried out the door to work.

Don't do anything I wouldn't do...

What does that even mean anyway, I thought. People say that but do they mean they want to do something your going to do, or I know your going to do something and you better not do it? Humm, I think in this context it means 'I think you're up to something'.

I showered and dressed real quick, bagged up the Jaclyn and dress and headed out. I had changed into yellow Lycra full cut panties with a little flower at top center under my jeans. I hadn't worn this pair of panties yet, and I again enjoyed the feeling of new panties. Besides, I wanted to be wearing new panties today. I was just so horny all the time lately.

I drove over to Cheryl's as carefully as I could under the circumstances. My palms were sweating and I felt my heart beating in my chest at the thought of my final destination this morning. It was hard to keep my thoughts on the light Sunday morning traffic.

"Hi Chris, come on in," Cheryl said with great enthusiasm, as I handed her the bag holding the Jaclyn. Bubbly seemed to be her natural state. She was dressed in a t-shirt, obviously bra-less and appeared to be doing something to her own hair when I arrived. She had full, sort of low hanging tits, I noted.

"So how was the party? Did you guys have fun? Did they like the look I gave you?"

Yea, it was great. Everyone was very impressed with your work. Someone wanted to know if you're available."

"Someone. Male or female?"

"Male actually."

"I don't know. I have to be careful about not being licensed, but I'd love to probably, yea."

That nails it down, I thought. "You're okay with that then? Doing another guy I mean."

"Sure, I like the challenge. My roommate and I would both be up for that. We could do doubles maybe? My instructors even use pictures of Drag Queens for examples in class sometimes. They do some amazing work you know. They say their good clients too. They spend tons of money and their better tippers than women are."

"Interesting. I'll be in touch then, maybe. I gotta run."

"Okay. I'm glad you had fun. I'd love to try another look on you sometime, sexy. Bye, bye."

I drove out to the edge of town to Jamie's and Linda's. Different scenarios were racing through my head. Would he be cleaning house in his maids outfit? Would I be finishing what I started last night? Did he even want me to? Did he want to see my small cock? I wanted to spend some more time in the play room. It was a transvestite's dream, that's for sure.

I pulled up in the driveway, grabbed the dress bag and rang the bell. The door opened with no one plainly visible. I heard James say "Come in, come in. Welcome," as he stood behind the open door somewhat.

"Good morning. Sorry for the trouble," I said as I entered.

Jamie was indeed behind the door. He wore a tight mid-thigh length skirt and sheer white blouse with a low neck line. He was actually wearing a string of pearls. They looked genuine. He had a short dishwater blonde wig on and very light make-up, with a pair of low heels. But he had no breasts. I could see a luxurious bra with A cups through the semi-transparent blouse he was wearing. I had expected the D cups he wore last night. It was a classic 60's TV housewife look, with no tits.

"Oh, it's no trouble. How are you today? I'm a little tired myself, but we both had a fun night. How about you two lovers?"

"Yes, I'm wiped out, but we had fun. It was... amazing actually."

"Amazing was it? I'll hang your purse right here so you can't forget it this time," as he hung the purse on the front door knob, closing it behind me.

"Would you like some coffee then? I know I needed an extra cup this morning. Come out to the kitchen with me."

"No, thank you. I don't drink a lot of coffee," I replied, following him into the kitchen. "I'm sorry about interrupting you today. I don't want to intrude."

He ran a glass of water from the tap and handed it to me. "Oh it's fine. Linda was hoping we could be friends with you two actually."

"She is? Yea... Sandy might be too. I'm not sure exactly."

"What makes you say that?"

"She said don't do anything I wouldn't do when she left this morning."

"Interesting. Was it a ha, ha, don't do anything I wouldn't do, or a you better not do anything I wouldn't do?"

"I couldn't tell really."

"Well, let's not do anything she wouldn't do then."

"But what about Linda?"

"We've talked about me having a special friend for a long time now. She knows the nature of the beast she's living with. Transvestite's are notoriously gay or bi-sexual. She is well aware of that. So is your sweet Sandy now, you know. Linda would rather know about it than have me lurking in the park or the adult bookstore to satisfy that side of me. I think Linda is more concerned about Sandy, really."

"Why do you say that? What does that mean?"

"Oh, you couldn't see her, since you were busy with Mr. Pantyhose yourself, but she actually licked her lips when she gazed upon Mr. Pantyhose. Linda saw it too."

"I knew it! I fucking knew it! She didn't say anything, but she was crazy last night when we got home. She, uh, yea... she was crazy horny."

"She what? I smell a story you're not telling me here."

"Yea, well. I was kind of quick on the draw when we got home, and.. she fucked my face... after... you know."

"Aah, cream pie dessert for you then, Chris?"

"Yes, up my nose even. I think she's starting to like doing it that way too."

"The more I know about her, the more I like her. So this wasn't the first time then?"

"No, it wasn't."

"Well it seems to me that you're not very upset with her interest in Mr. Pantyhose. You're okay with that, are you?"

"Um, I."

"You are. You're such a sissy."

"Can I ask you a question?"

"Sure, anything. What else is on your mind."

"You don't have very big tits today. Why is that?"

"Oh, it's a lot easier to do the housework without carrying them around. It's fun to have big tits for looks, but my bra feels so much better this way. Besides, it's 'Nipple Magic' day for me."

"Nipple Magic?"

"Yes, that's what I call it. It's a topical ointment I developed in my spare time at work. Linda calls it Pixie Dust for trannies . Follow me to my office," and Jamie led the way to play land.

I followed Jamie's wiggling butt down the hall and in to play land. He picked up a small opaque glass jar with a pinkish hue. "This is it. Doesn't look like much, but it's powerful stuff."

"What does it do?"

"It's probably easier to just show you," and he handed me the jar and unbuttoned the top buttons of his blouse and lifted a bra cup.

I was speechless. His areola was exceptionally large and feminine in appearance, with a bumpy texture, like a woman's, and somewhat swollen. It was an inch across, at least. The nipple itself was raised about an eighth of an inch and the size of a pencil eraser. If he had had more breast tissue, it would be a wonderful tit. It was intoxicating. My cock tingled in my panties and I fought off the compulsion to reach out and touch it.

"There not always like this. I put some on them this morning and it enlarges them for most of the day. It feels like a kitten is licking your nipple at first. I use it on Sunday usually, so the swelling goes down before the work week," and he lowered his bra cup and buttoned back up. "I wasn't expecting company, or I probably would have skipped today."

My cock was straining in my yellow panties and I felt my own nipples tingling without any additional stimulation. I was having a hard time getting over what I had just seen.

"Would you like to try some?" Jamie looked at me and said.

"Umm, I don't know. Don't they show through your clothes and stuff?"

"Well, a little bit, especially if I'm cold, but they won't be so puffy by tonight, so I just have big male nipples for the most part. Lot's of men have large nipples."

"Not like that," I said quickly. "How long have you been using that?"

"Oh, a few years now. You know what really feels divine is wearing a demi-corset after an application. I have an old one that will probably fit you well, if your interested."

"A demi-corset?"

"Yes, let me see if I can find it."

After some searching through a large chest of drawers he presented what I always called a bridal corset. It was a gorgeous piece of feminine apparel with sculpted half cups, size A, and made of sturdy cotton with silk or satin lining and overlay, all in white. It had what looked like yards of heavy laces and looked very expensive.

"I've never been corseted," I said with a short breath. It was a dream I'd always had.

"You've got to try it then," Jamie said excitedly, as if there were no other answer but yes. "Get out of those boy clothes and lets get busy. We don't have all day."

I quickly stripped and was handed a short silk chemise. "Put this on first. The corset never goes on first. Not a real one anyway." My nearly fully erect cock was evident in my panties, but Jamie paid no attention to my condition. I slipped the chemise over my head.

"Oh wait, we forgot the nipple magic," and he opened the jar and found a swab on his make-up table. He turned to me and lifted the hem of the chemise and dabbed each of my nipples with a small amount of the cold ointment. I could feel some warmth building almost immediately as the chemise fell down to my waist again. The silk chemise was enough to cause a full erection on it's own, let alone the sensation now emanating from my nipples. He then placed the open corset around me from the rear and told me to fasten the metal closures. I had some difficulty, but managed to get them closed.

Jamie pulled the corset in position at my chest. The effect of rubbing my nipples with the demi cup almost had me cumming right then. "Now, we're not going to lace you tightly today. Just to get the feel of it for your first time. This is a special order corset built for the slimmer hips of males. A woman's corset is built differently for wider hips," he recited as if giving a tutorial as he started pulling the laces from the center.