Happy Birthday to Me!

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Sam buys his first panties and the shop owner surprises him.
6.7k words
4.66
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Part 1 of the 2 part series

Updated 06/08/2023
Created 02/01/2018
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My stomach clenched, pulling in on itself. I had wanted to do this for years but fear and shame had held him back. This week had been my 18th birthday. It had passed with little fare. I didn't have a lot of friends, certainly not anyone I was truly close with. At just under 5 foot I certainly didn't have much 'luck with the ladies' as some would say. Oh, sure I could get them to talk just fine, but they always viewed me as 'cute'. Not the cute they used for the star quarterback, more like the cute reserved for children. I was slender, not much body hair to speak of, my face was soft in its lines but my chin was sharp. I wasn't quite feminine. I hated it. I didn't want to be a macho man, but I was still a guy damnit.

My parents hadn't made a big deal out of my birthday either. I was a senior this year and they behaved as if I should have my own life. They had purchased a new car for me and deposited a decent sum of money in my account. My father had made it clear however that I needed to find a job soon to start helping pay for the insurance and my own gas to get around. I had other ideas right now though.

It was Friday, my parents had left town for a few weeks, and spring break started next week. I could finally get my own underthings. I had always wanted to wear women's underthings. Boxers and men's briefs just seemed uncomfortable and often baggy. I had considered trying to steal some, but the only one I might access would be my mothers and even I would consider that wrong. With my bank card in hand I had left straight from school and headed to the mall.

There was a specialty lingerie store at one end. Not unlike Victoria's secret, but I knew this was privately owned. I had stared at it from a distance. I needed to be quick about it. I knew a few of the girls at school worked here on occasion, though I doubted they would give up a Friday night if they could help it, especially the Friday before spring break.

Crowds were already starting to gather but luckily the end I was headed for was still pretty sparse. I reached the last row and stopped, staring into the shop. She was there of course. The owner.

An older beautiful woman. She probably didn't top 5'5" without heels. Sleek pitch-black hair cut just above her shoulders in a straight line all around. Piercing pale brown eyes and an ample bosom. She was wearing a business-like suit. She rotated between more feminine appearances and business-like attire. Her facial features were a little angular, and dark makeup helped bring out even more contrast. She had a heart shaped ass that drove men wild. I got excited every time I saw her... except for today. Today I hoped she would take too much notice, or at least wouldn't say anything. I face was burning already. With a squint and a deep breath I gathered my courage and, well I didn't march, I slunk into the store.

Luckily with my short stature most people would be hard pressed to spot me behind racks of clothing. Unfortunately, she kept a watchful eye on her store with convex mirrors and the racks didn't exactly fill out when it was mostly panties, bras, and little lace teddies.

Ignoring the throbbing in my jeans I perused the store. Mentally grading everything I saw. Lace looked nice but when I felt it I found lace was stiff and had almost too much texture. Several silk pantie sets caught my attention. I didn't know how to categorize underwear really. But I liked the thongs and what I called near thongs. Finally I selected a few styles and chose an assortment of colors; black, beige, tan, and of course pink... With burning cheeks, I came to the register. Luckily it couldn't easily be seen from outside. For customer privacy no doubt.

The owner began sorting my collection, removing hangers and tiny magnetic tags. I refused to look up as she ruffled through them. My heart nearly stopped when she spoke.

"I don't believe you have ever been in here before sweetie."

"No maam"

"Oh honey, don't you maam me. I may be older than you but I'm not so old I don't remember my own high school days. I've seen you around before though."

My cheeks burned a little more fiercely and I glanced up to see a warm smile regarding him.

She reached out, cupping I jawline and gently stroked I cheek with her thumb. "There is no need to be embarrassed. I know it must have taken quite a bit of doing for you to finally come in here. Truthfully, I'm glad. Most men have trouble admitting to a want of finer clothing."

"Yes... ah?"

"Just call me Sharon sweetie."

"Sharon.. I feel like I'm gonna die from embarrassment really"

"Don't you worry. I'm plenty discreet. Now I know from a few of my girls you aren't seeing anyone. I've asked you see. You had me curious when you kept looking in here but refusing to visit little old me"

I gulped gently and stared back. I couldn't come to terms with the fact I was talking to her

"Now, since we both know you aren't dating anyone there is no need for games. We both know these are for you. Have you ever worn any dainty underwear like this.

"No, not really. I mean I've always wanted to. But I never had any access and it's not like I could ask for some."

"Not to worry. I'll take care of you. There is some self-care and etiquette involved and I'm more than happy to teach you. While I understand you may want discretion I'll tell you now there is no need to worry when you are here. Okay?"

"Well..."

"No but's young man" she giggled "Well, there are Butts of course but no... well you know what I mean. Now, what is your name?"

"But I thought you said you"

"Yes I know your name but it is still proper for you to introduce yourself.

"Sam, my name is Sam."

"Lovely to meet you Sam, you can just call me Sharon for now understand?

"Yes Sharon."

"Good now, One of the girls is going to come take over for me at six. Do you have plans? Actually it doesn't matter. You will come here at six. We, that is you and I, will go grab a light bite to eat and discuss proper underwear etiquette and care."

She bagged my things, and held them out. I took the bag before realizing I hadn't paid. I began reaching for my wallet when her hand gripped the side of my face and pulled my attention to her.

"None of that now. You will be here at six... Understand?"

"Yes maa... Sharon."

"Good now off you go. Get yourself cleaned up and finish anything you have to get done and I'll see you then"

With that dismissal Sharon walked off to the back room to take care of something I supposed. I was still shocked and walked out with the plain bag in a sort of trance. I didn't even think to be embarrassed walking out of a women's underwear store alone with a bag.

I drove home and let myself into the empty house. It wasn't until I had gotten into the shower to clean up that I even realized I was so hard it was hurting. I knew I had better take care of it before I met with her again.

Cleaning myself and using plenty of conditioner in my hair I reached down and gripped my hardon. Hand clasping around is shaft I worked it up and down slowly at first. I was hard as steel before even touching it. Hadn't really happened before. But as I suspected it didn't take but a few moments before I was painting the tile wall with my cum. While the erection did subside I still didn't feel satisfied. Something was missing.

With the talk of etiquette, I knew better than to put on my new panties before being told about whatever etiquette she had mentioned. I masturbated and cleaned up one more time before leaving to meet her. I was starving to be honest and hadn't eaten today at all, I nerves having gotten the best of him. Did this count as a date? Nah, I couldn't be that lucky.

I had arrived 15 minutes early and stopped by a restroom, made sure my breath was okay and checked my appearance in the mirror. As always, I felt a little disappointed in my sleight build and soft features. But felt I looked well enough. I had a button up shirt tucked in with a bit of play around the waist. My jeans were not loose and clung a bit to my legs and butt. Although not very masculine or muscular my legs were one of my good features. Both being very toned.

"Alright, you can do this!" I psyched myself up and headed out to our appointed meeting.

As I arrived I hoped I could wait outside for her but she spotted him, and upon realizing I didn't intend to come into the shop she placed both hands on her hips and began tapping a foot while looking at me pointedly. I curled in on myself in embarrassment but obeyed the unspoken demand and timidly entered. She smiled as I approached.

"There you are sweetie. And early to boot. I guess I shall have to reward you. Give me a moment to gather my things and we will be on our way." Her smile affected him easily and the pounding in my ears increased.

"Thank you, Sharon."

She walked off and I heard her call out in the back room as she gathered a few things.

"All right Kelley, you're closing up tonight I have plans for the rest of the night and won't be back in until tomorrow to check on things in the afternoon. Make sure Vanessa knows she is opening up!"

"Sure thing Miss Dorado! I'll give her a call in a moment." I heard footsteps on the carpet and was shocked, though I shouldn't have been, to see one of my classmates step out of the back room. My stance tightened and I glanced about for somewhere to hide.

"Oh!... You must be Miss Dorado's plans tonight!" I looked up to see a voluptuous teen grinning at me, one side of her mouth quirked higher than the other. Her eyes shining.

"Well... I, we, I mean yes. She planned to talk to me about some things and it's late so we were.."

"Don't be so silly in front of Kelley, Sam, I already told you no need to be embarrassed here. We are all quite understanding and discrete as I know you will find out in the future. Now we have to go. Tata Kelley"

Sharon took me arm in arm and with her sly smirk dragged me out of the store eagerly. She talked as we headed directly for the nearest exit.

"Now I have a few more things for you but we will get to those eventually do you have your... where are the things you came for this afternoon?"

"They are in my car... I didn't think tit would be appropriate to wear them since you said I had some things to learn and I didn't want to carry then through the mall so I thought we were"

"Quite right quite right sweetie, Now We will stop by your car to grab them and then we can order in so I can teach you what we ladies learn at a young age."

I nodded guiltily and followed her lead. She hadn't parked too far from the side entrance and I couldn't help but admire her car. It wasn't at all what I expected. It was an older luxury model car with tinted windows. I guessed I could probably lay out flat on the back seat and not be touching either door. With a few quick directions we stopped by my car and grabbed my bags.

The rest of the drive was filled with little chit chat, well at least Sharon spoke a lot. I paid attention and picked up on how cleanliness was extremely important, women's underwear was very expensive so extra care had to be taken in ensuring that certain types of stains and odors didn't soil the very best underwear they wore. When the subject came to be making sure I was properly cleaned I admitted I had taken a shower making sure to clean between my cheeks, and even when using the bathroom I always wiped thoroughly.

"Ahh my sweet Sam, but did you clean out?"

"Umm I'm not sure what you mean. I cleaned between my cheeks and I haven't had to go to the bathroom recently. I haven't even eaten today I was so nervous about coming into the store this afternoon that I skipped breakfast and couldn't eat anything at lunch."

"Really? Well now while that is convenient I can see you don't understand what I mean. I shall explain once we get home."

"Oh... okay"

Soon they arrived at a nice little house out in the woods. The driveway was relatively long and was closed in by trees on either side. The house itself was nice enough I could tell it wasn't some prefab, my parents always looked down on that sort of thing and I could guess she might as well. From the angle they approached at I could tell that the backyard was more of a pasture.

She parked and grabbed her bags before heading inside, with me right on her heels. She removed her shoes in the entryway and I follow suite. My guts were twisting again. I didn't really know how to behave. Before she mentioned ordering in I had assumed she would take him to some little café or the food court in the mall and explain things to him there. I had hoped for a little flirting. Never did I dream I would be in her home. She smiled warmly at my discomfort.

"Oh you poor dear, You're shaking like some frightened little fawn. I was hoping my feelings were a little more out in the open sweetie. I'm very much interested in you. Aren't you attracted to me?"

"Oh yes maam! But I.. well I didn't know what to expect I thought we were just going to have a bite and talk in a restaurant or a little cafe and that would be"

I was silenced when she reached around behind me and using the small of my back pulled me into her, my front to her side. Gentle fingers caressed my cheek and slipped behind my neck pulling me even further in. My heart hammered in my chest as her lips touched mine. It was a soft thing at first, but still insistent. Her tongue teased my lips open and she tasted my teeth before caressing my tongue with her own and withdrawing.

"Now now now, don't be so nervous my little fawn. Come with me and I'll teach you everything you need to know."

I nodded and swayed from the lack of oxygen before I remembered to start breathing again. I was entranced by her eyes and couldn't identify what lay behind them. I plodded after her swaying hips. She wandered through the house, past the kitchen and into the master suite with its large a joining restroom. A restroom that was as large as my bedroom back home. The bedroom door was closed behind us. I heard a click as it closed but didn't ask.

"Shoo shoo, in the bathroom my little fawn and strip. I entered the bathroom and she followed a moment later, she watched him with an interested smirk as I shook, slowly unbuttoning the shirt and folding it up. I placed that on the counter, then the pants followed. As soon as I was fully naked with my clothes stacked I turned back to her. She gasped and covered her mouth with a small hand.

"Oh my, I never would have guessed, not so little a fawn after all. I take it none of the girls have seen this?"

It was my turn to gasp as her hand wrapped around the rising shaft. She tugged on the skin a few times and then gave my testicles a firm squeeze before stepping up and moaning softly into my ear.

"I can tell you right now if any of the girls knew about this you wouldn't be spending many weekends alone."

I stuttered under her ministrations. "I.. I... I always thought I was normal or small. All of the guys as school make fun of me for being so scrawny all the time."

"My dear fawn. I can tell you right now you are quite gifted. Even disproportionate for you size. It is quite the contrast. But enough of that for now. We have other things to attend to first."

I withheld a whimper as she released my tender testicles. She walked over to the tub and started the shower. Seem started to build. She pulled out the waste basket and started pulling supplies out from under the sink. I recognized the electric clippers, a safety razor, and even a loofah and various bottles of shampoos, soaps and lotions.

"You might be disappointed at your lack of body hair but I can tell you now that it's actually a blessing. So, our shaving will be limited to your crotch and butt."

"My butt... We are going to shave my butt?"

Sharon giggled, "Of course you silly fawn, you don't want any butt hairs getting in the way of your new undies and it's SO much cleaner that way. Now stand directly over the basket."

I nodded and obeyed, finding over the next minute or two I needed to steady myself against the counter. Her movements were deft and somehow practiced and she quickly used the trimmer function of the electric razor to remove the bush and bunches of hair. Soon my cock was surrounded by nothing but stubble and scrotal hair was extremely short. Her hands felt like magic, feather soft until she had to pull my cock to the side. My knees almost buckled when she stretched the ball skin out to prevent wrinkles as she cut. She brushed me off last.

"Now I need you to face the mirror, hold onto the counter and lean over a bit for me."

I gulped but nodded as I did so. This was not at all like anything I had expected. The suspense was winding my chest up. She knelt behind him and I couldn't see her in the quickly fogging mirror. I tried not to jolt as her fingers gripped my cheeks and pull them apart. I had thought I was exposed before but this was a whole new level. I thought I heard a groan coming from behind me, but before I could ask the gentle stroke of a finger across my most private hole cause me to slip.

Managing to catch myself before falling, I asked "Is something the matter Sharon?"

"Oh.. no, not at all my little fawn. I won't be need the electric razor for trimming here. Butt" she giggled "We do need you to wash up a bit now. I'm going to get a few other things ready while you rinse off and wash. Use this body soap and my shampoos and conditioners. Okay sweetie?"

"Yes Sharon." I climbed into the tub with wobbly legs and she pulled the curtain shut. Holding back from playing with myself was more difficult than I thought it would be. The sensations caused by missing pubic hair cause me to shiver, but I managed to get past it. I got my back with the loofah and washed my hair.

I loved the scents of her care products. I couldn't identify what they were and the labels were very plain. They didn't smell like any fruit or flower. Instead they were almost like softness bottled. The closest comparison I had was getting a faint whiff of baby powder. But a bit of moisture due to their nature.

"Don't turn the shower off, just used the water saver. We still need that water sweetie."

"Got it."

I found the switch behind the shower head and the flow ceased, though I could still hear the water running behind the wall. The curtain was pulled back and she was still fully dressed. I was a little disappointed but knew better than to say anything. She caught the look anyhow.

"Oh, I'm so sorry Sam. I just got caught up in what we were doing it didn't even cross my mind I should reward my view by giving you one of your own." With a saucy little twist, she pulled off the over coat and started swaying to unheard music. She rans one hand down her side and used the other to release a single catch of her shirt at a time. Every morsel of cleavage heightened my arousal. The blouse fell to the ground in slow motion. I was focused on her bra. It was amazing how so little delicate cloth could contain such magnificent flesh. Her arms reached behind her which only served to accentuate her assets. With a snap I could see the tension in her bra release. It shrank even further to my surprise. She let that side down her arms to the floor.

I feasted my eyes on her breasts. Truly the first I had ever seen in person that I could remember. While her skin was tan her nipples were darker than I expected. Each larger than my own but they seemed like small little nubs compared to her breasts. They were hard. And since the bathroom was steamy I knew from watching and reading porn that she was definitely aroused. I was doing happy dances in my mind. But couldn't seem to move my body. Just staring in shock.

Smiling coyly and slowly dropped to her knees, I could feel my penis throb with my heartbeat. I thought I was already at full mast but I felt myself getting harder. With a little moan she eyed my member hungrily but said,

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