Helping Hand

This story was written for Jordan, my first patron. He loved this story and decided to share it with you all. I appreciate you Jordan and all my readers.

I smiled walking through the store waving at a few of my co-workers as I made my way to my department. I always loved how my heels sounded on the linoleum floor, I sounded powerful, I sounded sexy and all day I helped other women feel the same way. I worked as the manager for a department store that sold all kinds of high class clothes and I happened to be the manager of all things lingerie.

I looked at the picture of me on the wall "manager of the month." I was proud of the achievement, some of the other managers didn't care but I loved my job. I had a real job wearing designer clothes and got to help people feel beautiful everyday. This was far from where I was five years ago so I appreciated every moment I had.

I spent hours happily doing idle tasks and greeting customers, we had all types that wandered through the store. Suburban moms taking a break from their kids and trying to feel sexy again, the social elite looking for their casual night time attire and the occasional man looking for something for his wife or girlfriend or mistress depending on the day. I didn't mind people's motivations to look and feel sexy , my job was to get them there and I did so with pride.

Today however was a slow day, as autumn falls on us and people spend more time cuddled up you would assume sales would go up but in all reality they slip the other direction. I kept myself busy with idle tasks of tagging new items and deciding what got folded and what went on display. I barely noticed the man who had wandered into the racks behind me. I just smiled at him and continued on trying only to pester people once they have asked for help.

I decided a change of a mannequin was necessary for the flow of my little space and wondered what outfit it should wear. I wandered through the racks looking for what I wanted to dress the alabaster doll in when I crossed paths with the man again running his hands over lace panties.

"Can I help you?" I asked as politely as I could watching him jump in my presence.

"Uhm no I am ok thanks."

"OK well I am right over there if you need me!" I smiled at him unsure of why he was so nervous but some people acted that way around fancy underpants.

I continued putting together an outfit and performing the arduous tasks of stripping the doll and refitting it with new clothes. The display outfit would have to be tagged and sent back as we could not sell it now. The man stared absentmindedly at a size chart I put up, I felt a source of pride knowing it was getting used! So many women did not know their size correctly and just bought things, I was out to change that.

I resisted the urge to press him again when he turned to me. I smiled and made my way to him taking his eye contact as a subtle summon.

"How can I help you Sir?"

"Yeah uhm, I am having a hard time figuring out sizes for someone uhm bigger."

I was beaming, loving the opportunity to help and enjoying how nervous he was. It was cute for such a handsome man.

"Well the size chart here is your more standard sizes but if we can nail down a height and approximate weight I can give you some ideas of where you should be looking."

He looked at the ground and then back at me his face was getting redder by the second. He swallowed hard and tried to say something but couldn't get it out. He snapped his mouth shut turned and walked away without a word.

I watched him go confused about the interaction we just had.

Had I offended him? Why didn't he buy anything? Did he like my size chart?

I do not know why he occupied my brain so vividly but I had him on my mind the entire time he was away from me wondering if I would ever see him again. I glanced up from time to time hoping it was him at my size chart ready to let me help him find the size he needed but a week passed and nothing.

I gave up on the man, I assumed he loved my size chart and just was having a hard time deciding what to buy and got flustered. I let my brain create the scenario that best fit my needs and went with it. It wasn't much longer that I had a very interesting conversation with a young woman. She was looking for a bra and panty set, I assumed for her and was getting things I thought would fit when she stopped me.

"I know this is a little weird but its not for me it's for my boyfriend and he's just a little bigger than me, maybe 40 lbs or so and almost six feet tall."

"Your boyfriend... wow this is a first. Of course I will size up!"

She was far more at ease with me after that interaction and I was fascinated with the idea that she was buying things to dress up her boyfriend. She explained he liked to be feminine with her and she supported his sexual desires. My mouth was agape as she pulled nail polish, a wig and a dress out of her bag she planned to surprise him with.

"I know this is a bit much but I want to hug you! You are doing such a great job helping him feel sexy. Its what I do here all day and I am always supportive of it!"

She laughed at me in full. Before opening her arms and letting me give her a hug.

"You are alright lady, I figured in a store like this you might be a bit stuck up."

"Oh please call me Cassandra! Never, in my little slice of the store we show support!"

I was getting excited and loud, I covered my mouth and giggled with my new friend. We picked out a few outfits and sent her on her way. I felt so proud to be able to help that couple out and I hoped she would come back and tell me how much they liked it, nobody ever did but a girl can dream.

I was riding the high of helping the couple while I continued straightening up the store when I looked up at the size chart and it hit me like a ton of bricks.

HE WANTED SOMETHING FOR HIM!!!!!

My inner voice chided me for being so stupid and not seeing it ahead of time, but how was I to know? I felt dumb regardless and swore I would help him if he ever came back. I was disappointed closing up at the end of the day when he hadn't, I had no idea why I was so invested in seeing him again.

When I got home I did some internet searching and found that there were LOTS of men looking to wear panties and bras, some even liked it when their girlfriends used a strap-on with them. It was far beyond my very vanilla sexual tastes but I was fascinated by it and also a little disappointed in the ill fitting lingerie some of these men were wearing. Eventually it was too much for me to bear and I made an account so I could start posting comments.

I spent two hours offering unsolicited sizing advice.

"This color is perfect on you but go one size up on the panties next time."

"This corset does not fit your frame, you need something that has a bigger bust."

"Thigh highs are cute but without a corset they end up sloppy, and if you try pink with your skin tone you will look fabulous."

I was addicted to helping. I made over 50 comments my first night. It wasn't long before I started to get messages from people wondering if I was a troll or the real deal. I assured them I only wanted to help and with that spurred up some friendships. I had never considered dating a man who dressed up, but I will admit the thought was growing on me so much that during the day I pictured men I saw in various pieces.

It had been three weeks since I last saw that man and I was more into his assumed lifestyle than most would expect from me. It was my dirty secret, vanilla department manager by day, dirty lingerie fit consultant at night. I had even gone so far as to start fantasizing about some of these very attractive men. My inbox was filled with men asking advice on what would fit them and sometimes the pictures were explicit and arousing. I found myself touching these random images and thinking about them in bed. I couldn't stop.

I never hated my job but this new found niche renewed my passion for it if that was even possible. I spent my days looking at pieces and taking quick pictures to send to people letting them see an example of what they should have. I was snapping a picture of a baby blue lace boy short bra combination when I saw him. I almost dropped my phone. I was so excited. I had to remember that I really didn't know if he was looking for himself. I had to play it cool.

"Hi, great to see you again. How can I help you?"

"Uh hi, sorry about last time you know I uh, get nervous." He said obviously running out of the confidence he built up to come say these things to me.

"No problem at all, now what can I help you find? I have a wonderful burgundy set I think would look great on you."

I slammed my hands over my mouth, I couldn't believe I just said that to him. His face turned burgundy and he turned to flee once again. I reached out and gently grabbed his elbow.

"Wait! I am sorry if I assumed incorrectly. I just want to help you find whatever fits you or anyone else I promise. I just want to help you look good or buy something that will make someone else look good." I was grasping at straws hoping he wouldn't just storm out again.

He turned, looking at me in full from my pumps to my black hair he looked me up and down. I awkwardly smiled at him trying to hide my own nervousness.

"How did you know?" He whispered.

I exhaled deeply holding my chest. "I didn't at first but I pieced it together after a young woman came looking for something for her boyfriend. I had no idea about men in panties until about two weeks ago."

"I am ashamed of it, I don't know why I like it but I shouldn't." He looked downcast.

I held out my hand to him and tried to offer a warm smile. "Come with me, like I said I have a burgundy set that would look great on you. You should never be ashamed of what makes you feel beautiful."

He followed me to the other side of the store where I had already pulled the items just in case I ever saw him again. I put them in his hands and let him feel the fabric.

"Now when you get home, you are going to want to wash up before you get started trying it on. You dont want it to cling to you, you want it to hug not suffocate."

"Thank you, you have no idea.." He trailed off.

"What's your name? Mines Cassandra." I said pointing at my name tag.

"Jason."

"Well Jason, try it out and tell me how it fits." I smiled, handing him one of my cards.

He smiled, taking it from me. I bagged his clothes in a plain bag vs the loud pink one so he could walk out in peace without feeling the eyes on him. I never did any drugs in my 35 years but I drank a cosmo once and the feeling I had right now was much the same. I was swimming in euphoria. I floated through the rest of my day excited to get home and to satisfy this lust I felt for this stranger I helped.

I watched videos of women "pegging" men, the power they held was beyond exciting. From the women that pounded away to the women who sensually stroked it was all a turn on for me. I let my fingers twist and turn, penetrate and slap my mound while I watched climbing to my mountaintop.

My phone chimed, I ignored it, I chimed again, I slowed down catching my breath trying to compose myself just in case it was my boss but instead I had two text messages.

"Hey it's Jason, does this fit right?"

What followed was a picture of his completely shaven fit yet slender body in the burgundy set I picked out for him. I gasped and rolled my nub holding my phone in one hand staring until I came all over my fingers. It took me a moment to compose myself to respond.

"You look absolutely amazing, that is your color!"

I was proud of myself and feeling ready to go again. When he surprised me with a phone call.

"Thank you so much...sniff.. I f-feel amazing." He said through what sounded like tears.

"You're welcome, are you crying Jason?"

"I just am so happy I, I just- thank you."

"You are so welcome."

I bit my lip taking my hand off my pussy so I could muster the courage I needed.

"Hey um I know we don't know each other well but if you are not seeing anyone or anything, maybe we could like, you know, get a coffee or something?'

I mentally kicked myself for rambling, I was suddenly ashamed myself asking out a perfect stranger.

"Really? Like..a Date?"

"I mean if that's too much we can call it...something else."

Again I cringed.

"No, a date is fine, yes let's do it!"

I felt relieved with the excitement in his voice and we set up for the following weekend. We exchanged texts back and forth over the course of the next several days and my anticipation for our date grew. He was nervous about it but agreed to wear his new outfit under his clothes on our date. I learned from the internet that some men liked to dress up like women to be dominant so I was trying my hand at it.

I was so far out of my lane, the last time I had sex was years ago with a guy that ditched me right after. It not only damaged my self esteem but kept me clear of most casual encounters ever since. The difference here is he already put himself out there so I tried to match him. He was all I thought about, at work I had so many sets ready for whenever he wanted more ready for him I had almost a whole catalog set aside. I ended up having to sell one as a woman needed his size but I managed to get over the disappointment.

The day finally came when we would meet and I sat down arriving early sipping tea with honey and lemon. I was worried he wouldn't show, I was worried he would see through my dominant disguise, I was worried up until the moment I saw him red faced and walking towards me. He offered me a shy smile and sat.

"Well hello, I was nervous you wouldn't show."

"I almost didn't to be honest, this is the first time I have left the house dressed like this."

I looked at him in his khakis and cardigan and was confused until I remembered he was to wear his panties.

"Oh! Well I am honored you decided to show up dressed like this after all. You know nobody can tell right?"

I took another leap of faith from my internet masterclass on "how to be dominant" and put my hand on his as I said it, relaying some affection and hopefully power.

He somehow got redder and smiled.

"Thank you for this. I've never had anyone encourage me like this."

"Thank you for being open to it. I will admit I am new to this as well. How about we learn about this together?"

Again he smiled. I got him to go get some coffee and we chatted about everything outside of the fact that we had a mutual interest in panties. He was a sweet man and opened up slowly to me as the minutes turned into an hour, turned into two.

"How do you feel now that we have had time to settle in?"

"Strangely comfortable but I think that's your fault more than what I am wearing."

I giggled, "you are comfortable because you are being yourself not hiding."

It was his turn to laugh, "I am way hiding, if I was myself I would be completely dressed up as a woman."

"Well why don't you?"

His laugh this time wasn't as confident as "I couldn't take that chance at ridicule, people would laugh."

I frowned but he had a point about our conservative town, only the younger generation was forgiving about such things. Then an idea hit me.

"What if we went somewhere where it wasn't odd or out of place?"

"We?"

I placed my hand on his again.

"Of course, you and me, we can dress you up and take you to a Halloween party!"

"A what!"

"Think about it! Everyone will be dressed up, we can dress you up as a princess or something, people will think it's ironic and we could even put a mask on you so nobody knows who you are! Hiding in plain sight just like right now!"

He shook his head furiously, "there is no way I could do that."

I rubbed his thumb, "You can, and I will be with you every step of the way."

I steered the conversation to safer waters for a while letting him once again get comfortable when I looked at my watch and mentioned the time feeling like it was time for another bold move.

"Would you like to see some of the people I have helped find the right lingerie for them?"

"What do you mean?"

"I talk to people on the internet and they send me pictures if you want to see. I think you might enjoy it."

He nervously looked around. "Here?"

"Sure, or we can go sit in my car if you like?"

I was liking this dominant streak in me, he nodded his head and followed me to my car. I was glad I parked where we would have low visibility to the front of the shop. I was feeling a rush and wanted to push my own boundaries as well as his. We sat in the car and I opened my phone swiping through various photos talking about what was wrong with each and how we fixed the issue. I could see his pulse quickening and could hear him getting excited with the questions he was asking.

I bit my lip and casually started scrolling through some of the more explicit photos, ones that showed a hard cock or a dildo penetrating. I handed him my phone.

"Here take a look, see anything you like?"

"I can't believe people just send these to you."

I let my hand travel over the center console and into his lap.

"They send them because I help them, I love helping people."

He looked down at my hand and gulped while I made my way to his belt.

"I-I wanted to talk to you about that actually."

I unclasped the belt with one hand and went for the top button staring down at the bulge in his khakis.

"About what?"

I was half listening with all the stimulation, his pending reveal, my phone showing a man sitting on a strapon in full lingerie, the depravity of it all, it was almost too much to hear his words. I unzipped and looked up at him before I exposed him.

"You should open a store!" He blurted.

It caught me off guard and snapped my focus away from his pants.

"Wait what?"

He exhaled looking down at my hand gripping the inside of his zipper ready to pull.

"A store, so you can have a private place to help people. You obviously have an audience you could offer discreet shipping."

I pulled my hand away, shocked at his thoughtfulness to even mention that I could do such a thing. I almost didn't even register his look of disappointment now that my hand was gone. I immediately put it back but held still.

"I don't know if I could do something like that."

His smile almost broke his face. It was so wide.

"You can, and I will be with you every step of the way."

I shook my head smiling at my own words being used against me. I looked up at him.

"I am going to open your pants and if your dick is hard I am going to suck it right here right now."

His eyes went wide and I smiled, opening his pants revealing his hard cock and a wet spot on the front of the burgundy panties where his precum had leaked. I pulled the band down and within seconds I made it disappear down my throat.

"Oh god!" He moaned.

I sucked furiously enjoying my first cock in years dripping my saliva all over his panties. I struggled to reach my own button in this position, I needed to be touched, anywhere. I grabbed his hand and placed it on my breasts, he immediately got the picture and went under my shirt to search for my nipples. He wouldn't get a chance to find them before he tensed and came in my mouth. I was caught completely by surprise and choked on the first rope hitting my throat and subsequently let each one following hit the roof of my mouth and drip out past my lips. I looked down at the mess in his pants and the front of his panties.

I leaned back looking at him catching his breath.

"I am sorry I made a mess, you kinda caught me by surprise."

"That-was-the-best-thing-to-ever-happen to me." He breathed in staccato.

I smiled and opened the glove box pulling out some napkins for him to clean up.

"Not bad for a first date, maybe next time I will get a strap on for you." I poked to see what he would say.