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.
He rolled his head on the head rest to face me with his hand full of napkins he had yet to use.
“Ill do the party if you make sure I look nice.”
I blinked, this was a lot for him I could tell. He began to clean himself as we sat in silence for a moment.
“I will make you beautiful.”
Our date ended and I kissed him for the first time, I had to point out I kissed his dick before I kissed his lips and we both had a decent laugh at that. I wasn’t even out of the parking lot before he was texting me looking for another date. I loved his eagerness. I considered his idea of driving to our town’s shop for sexual accessories.
My own shop, how would I even begin?
I ended up making a purchase of a harness and a six inch cock, thinking it would make the most sense for his first time and mine. I was eager to try it on my whole drive home telling Jason I had a surprise for him. I stood in my living room wearing the harness humping the air feeling silly. I took it off and put on my own lingerie before putting it back on, I looked at myself in the mirror and that’s the moment I felt like a sexy dominant. I took a quick picture and sent it to him.
I waited longer than I thought I would have too before he responded by sending me a picture of himself in his burgundy with a hard cock. I smiled like a teenager, I replied with comments on how he owed me one. Playtime was nearing its end as I still had to go to work. I rebuffed his request to come over and give me what he owed, as much as I wanted it, today had been a day and I needed a night’s rest.
I woke up to a good morning text, it started my day with a smile. At work we text back and forth like love struck teens. I picked out a few items and paid for them to go with the halloween costume. I settled on the classic playboy bunny look, a bikini corset, nylons, and the head of a separate bunny costume. So he could feel sexy and be hidden. He was still nervous about the idea but agreed so went with it. The party was in just a few days and we didn’t have long to prepare.
The end of my day took to long to reach me, I packed up shop wondering how things would go if I owned my own store, the things I would change. One thing I did know, I was keeping my size chart!
We agreed to meet the following day giving me more time to sew a bunny tail on the back of the corset but once I had the entire outfit laid on the bed I couldn’t wait. I picked up my phone and called.
“Hey! Didn’t think I would hear from you today. I am excited about tomorrow.”
“Yeah that’s what I am calling about I can’t wait, I am sending you my address, shave everything from your ankles to your eyebrows and meet me at my house!”
I had to wait a whole hour and a half before my doorbell rang. I sprung to get the door wearing the same lingerie from the night prior under my robe. I opened the door and jumped into his arms planting a long kiss on his lips. I felt his unease melt in my mouth as I broke the kiss and led him in.
“How did shaving go?”
“It was more difficult to reach certain areas than I thought it would be.”
I laughed, it sure is. “Maybe next time I can help.” I led him to my bedroom, smiling back at him already seeing the bulge in his khakis.
“Yeah I would like that.”
“Good now, close your eyes!”
His hands went to his face and I led him the final few feet and closed the door behind him. I led him to the foot of the bed and told him to open his eyes. I watched as he excitedly ran his fingers over everything.
“You like?”
“I love it!”
“Well put it on! I will grab us a few drinks and let you get acquainted.”
I landed a playful pat on his backside and walked out the room grabbing some glasses pouring some tequila. I walked into the living room and placed the glasses down pulling out the strap on and putting it on, opening the robe posturing myself so that as soon as he walked out he would see me lounging wearing the fake cock and lingerie.
I nervously took a sip and adjusted my bra, ran my finger through my hair and tried to put on my most seductive face. I waited a moment, re adjusted, went for my glass again and finished it to calm my nerves.
“Almost done there?” I called out.
“Uhm yes, I am coming.”
I grabbed his drink and took it down in two gulps. I felt like I was about to start sweating. I got my pose just right once more when the doorknob turned and he opened the door. We both froze, our eyes wide taking each other in. I was the first to move curling my finger at him and he followed wordlessly his outfit betraying his arousal.
I waited until he stood right in front of me, I reached out running my hand over his smooth nylon covered thigh.
“You look great.”
“Y-You look amazing.”
I stood, rising to my tip toes. I kissed him. We let our tongues dance for a moment as my fake cock poked his real one.
“On my bed.”
He obeyed without hesitation and was on his back on my bed in moments. I undid his corset but left the nylons on him.
“Have you played with your ass before Jason?”
I pulled the vial of lube I got with the cock out and began lubricating the cock.
“Yes, I have a dildo I practice with…mistress.”
I arched an eyebrow at this new word he was trying, I liked it and wanted to explore it late but now I wanted to try this.
“Good so this shouldn’t be an issue, but let me know if you are uncomfortable.”
He hooked his hands behind his knees and pulled his legs back.
“Yes Mistress.”
I was nervous, yet excited as I walked up to the edge of the bed and ripped a hole in the crotch of the nylons. I lined up and slowly pushed. He didn’t flinch and moaned for me as I sunk it in. I was more shocked than he was.
“You like that?”
“Yes! Mistress please fuck me!”
I wished I would have practiced more, I began to thrust slowly unsure of how rough I could be. It took me a minute to catch my rhythm but when I got the stroke we were both comfortable with it was beyond apparent. His moans echoed in my room and his cock strained under the nylons. I reached out and stroked him through the fabric allowing him to feel it.
“That’s a good girl.” I whispered to him.
Again it didn’t take long until he finished all over himself. I leaned forward and licked the head of his cock through the nylons making him jump as he was still sensitive. I kissed his shrinking shaft as I pulled out of him forcing him to moan more. I sucked his balls while I unstrapped myself and then let the cock hit the floor.
I stood watching him look up at me. “Come take these off sweetheart.”
He quickly scooted to the edge of the bed and to his knees taking his hands and slowly peeling my panties off of me revealing my wet mound. I pointed to the bed and he climbed back on, staying on his back. Climbing on top of him I stopped to kiss his cock and then his lips before putting my thighs on either side of his head.
“Eat me slowly.”
He mumbled what I assume was yes mistress while his tongue danced in my pussy. I moaned and rode his face. It had been so long a man had tasted me I felt the wave grow quickly before coming crashing down on my body leaving me a quivering mess. I laid down next to him kissing him, tasting myself on his lips and feeling his wet nylons in my leg.
“You are an amazing mistress.” He moaned into my mouth.
“No you are amazing.” I giggled in return.
We spent the rest of the night rolling in bed kissing and giving me one more orgasm before drifting off and making me late for the first time in a year, it was worth it.
Having Jason distract me I had gotten behind on my messages from people on the internet. I spent most of my day replying to people and taking photos seriously considering the idea of opening my own shop. I began to google how to start my own business and saw how much I needed. I had about half, so I started a savings goal and smiled. I was going to do this. The next day was all planning as I worked out a business plan and talked to the bank about my options. I needed to find a location but otherwise the bank was willing to lend me the money.
I took Jason with me every step of the way, we spent the entire day together and were both just as excited about “Cassandras” as we were excited about his first outing as a woman. Hours before we got him dressed again having to buy new nylons so we didn’t have him out in ones we ripped and came in. I felt his nerves coming back walking him out the house with the mask on. It was obnoxious in the car but I knew it made him feel comfortable. I placed my hand on his thigh as we drove talking about ways to design the shop to take his mind off what we were about to do.
When we pulled up we saw several anonymous people funneling into this nightclub Halloween party. Scandalous was not even the word to describe today’s “costumes” they were down right slutty and my witch costume made me look like a hag.
“Are you ready for this?”
“No I am not.”
“Do you want to stay here?” I asked, squeezing his thigh watching the head tilt down.
“No, let’s do this, mistress.”
That night Jason and I had an amazing time and it was truly the day my business partner and wife came into the world. That was five years ago and today Jordyn and I fell in love on a dance floor with a bunny head piece between us. We still have that very head in our store, just to be able to tell the story. If you ever need a helping hand feeling pretty and getting your sizing right feel free to call on us at “The right touch” lingerie.
xx
Belle