There I was your typical broke student.  I was struggling to pay my rent, food, clothing and beer bills.  Then I got a lucky break.  Besides the two bar sessions that I was doing I was told that a shoe company wanted assistants.  I was straight down the high street applying for it.  Although it was in the poorer end of town it was a high-class shoe company that specialised in not just selling shoes but also making them made to measure.  I did my best at the interview and was glad to hear a few days later that I had shifts on both Saturdays and on Sunday mornings. 

My first shift in the shop was a bit of an eye opener.  One of the girls took me under her wing and soon I was on my own helping the customers.  The company paid fairly good money and had a good bonus scheme depending on how many and how expensive shoes one sells.  I was soon doing pretty well and was soon on top of my bills.  Then on my third weekend I got more than I bargained for as I knelt to help this middle-aged woman try a pair of shoes.  The moment the shoe was on her foot she held her foot up as if to look at it on her foot.  I had an unfettered view right up her skirt to her naked pussy.  As she wiggled her foot around, she whispered to me, “Does it look ok from down there?”  I told her it certainly did.  Then she decided that she didn’t like them for some reason, and I was helping her back into her own shoes.

I still had a good view of her moist looking pussy as I helped her on with them.  Then she stood and walked to the front of the store where she met up with her boyfriend or husband who had a big grim on his as he watched me watching her.  I had been set up.  I didn’t care as I had enjoyed the show anyway.  As I packed up the shoes she didn’t want and return them to the warehouse one of the girl assistants asked had I enjoyed the show.  I must have looked confused as she added the view up the woman’s skirt.  I went a little red as she added that the woman did it to all the male assistants and to just enjoy it if it happens again.  I asked did it happen very often, and she said that I would get a flasher about every three or four shifts.

She wasn’t wrong.  Over the next six months I got flashed fairly regularly.  Most of the flashers were late teenagers doing it as a bet, but then there would be the occasional older woman who was doing it because she enjoyed showing herself off.  It was fun but a waste of my time as I could have been making sales towards my bonus.  Then late one Saturday afternoon it happened again.  Only this time it was much different.

The woman was probably in her forties and straight away she made a bee line to me and asked if I could help her.  I could see that the fairly good-looking woman was wearing quite a lot of jewellery and a very expensive set of rings on her wedding finger.  Her clothes looked immaculate and very expensive.   I asked what I could do to help, and she immediately said that she wanted some shoes made and would need a full fitting.  I quickly said yes and went to grab the foot gauges to measure her feet.  Bespoke made shoes, rather than off the shelf shoes, provided much better bonuses and more likely to result in a sale.  By the time I had returned to her she was seated on a chair waiting for me and as I knelt, I could see her nicely painted toenails through her strappy shoes. 

I asked her which foot she usually had measured, and she told me her feet were both different and liked both being measured.  I eased both shoes off and she raised the first foot to be measured.  It was now that I saw that she wasn’t wearing any panties.  I don’t know why an older woman should get my cock swelling, but she did.  I took all the measurements for her first foot and as she removed it from the foot gauge, she rubbed it across my cock.  Then she bent her knee on the other leg giving me an even better look at her pussy.  My poor cock twitched at the sight.  Then she put her foot on the gauge.  I was struggling to take the measurement as my cock was screaming at me.  I tried to rearrange my trousers without her or anyone else seeing, but she had and said, “Oh you poor boy.  I wish I could do something to help you.” 

I had just about got all the measurements I needed and then asked what type of shoes did she want made, and she said she wanted shoes and boots. Boots meant that I needed several calf measurements and I got out my tape measure and with shaking hands took measurements on both legs.  As I did, the foot of the leg not being measured rubbed my cock and stayed on my crutch.  By the time I had all measurement I needed I was in quite a state and had to rearrange my trousers again.  This time as it was her fault, I made no attempt to hide from her me rearranging my clothing.  She smiled as I did it and then went to get the style books for shoes and boots.

As I got them, I wondered if she was another prick teaser and would leave me in a state and with no orders as had happened several times before.  She flicked through the shoes and said which ones she liked, she had picked out four pairs, and then started to look at the boots.  She picked two pairs and then asked did we do any strappy boots.  I had to aske one of the more experienced assistants and she looked at my hard cock as she said we did and told me where I could find the books.  On returning to her she picked out three pairs and said could she order them.  I enquired, “The strappy boots.”  She answered yes and the other boots and shoes.

I must have been stood there with my mouth open as she told me to shut my mouth and get my pad and write the styles and colours down.  It was the biggest order I had ever taken and as we got to the tills, I totalled up the costs and told her that we took a twenty five percent deposit on all orders.  She just smiled at me as the manager joined me at the tills.  He quickly said, “Hello Mrs. T………   Sorry the lad didn’t know you are the owner of the shop.   They should be ready in four to five weeks.  We will let you know when they are ready.”

“You can send the lad round when they are ready so I can have a fitting,” she told the manager.  He just said yes as she walked out the shop.  The manager grinned and said that the lady had taken a shine to me as he looked down at my still stiff cock.  It was five weeks later when I turned up for my shift that I was told not to take my coat off as I was on a delivery.  I looked confused as he grinned at me and told me that Mrs. T……..’s shoes were in and I was to deliver them for her to try them out.  I loaded the boxes into my beat up mini and set off for the address I had been given.

A man I presumed was a butler let me in and showed me through to a lounge with my boxes of shoes.  He told me that the lady of the house would be with me shortly.  It was almost twenty minutes when she breezed in dressed in a tight white blouse and even tighter short blue shirt.  She had a huge smile on her face when she saw me and said to unpack the first pair as she took to sitting on a fairly low chair.  She kicked off her slippers as she waited for me and then held her first foot up ready for me to put the shoe on.  Already my cock has started to grow as I knelt and took hold of her foot to put the shoe on.  It was impossible not to look up her skirt at her freshly shaved pussy.  I could see all the way to her clit ring.  I hadn’t seen one before and wondered if it hurt when it was inserted.  Then as I put the second shoe on, she ran her other foot over my bulging cock.

Then she was stood and walking up and down the room several times.  “They’ll do.  Now the next pair she insisted.  As I removed the first pair and put the second pair on her feet, she again teased my cock by rubbing her feet across it.  By the fourth pair I was almost ready to come.  I got some respite as she called for the butler and told him to put the shoes away for her and she would be busy for some while and not to disturb her.  As he took the four boxes he gave me a sideways look, then he was gone.

She waited several moments and then said,” we had better take care of this before you get into real trouble,” as she rubbed her hand across my bulge.  With that she unzipped my stiff cock and it sprung out pushing my underpants out the way.  “My we are excited aren’t we,” she declared as she wrapped her hand around my cock and started to wank me off.  It didn’t take long, and she quickly had tissues ready to capture my load.  Then with my cock still dangling and my offering thrown into a bin, in the tissues, she sat back down and told me to try one of the pairs of boots.  I picked a pair and had to wrestle it up her leg and then zip it up.  As I pulled the second one on, I was looking straight at her glistening pussy.  I could feel my cock showing interest again already.

Then as she walked up and down, she asked what I thought, and I genuinely told her that they looked bloody sexy on her.  She sat again and I pulled the first one off and reached for the zip on the second one.  The thought passed my mind that reaching just a little further I could touch her pussy.  The thought had my cock beginning to throb again.  I was glad that it was soon off without any embarrassment.  Then the next pair were even longer and came right to her knees.  As I pulled the first zip up, she caught my hand and led it up her thigh to her pussy.  It was not only glistening but also very hot and wet as my fingers brushed against her pussy lips.  She just groaned and after a few more strokes told me to put her other boot on. 

I wasn’t sure what to expect as I pulled the second zip up.  She stood up and stepped away and walked up and down.  She declared them to be good and as she returned to her chair, she grabbed me by my blond hair and rubbed my face into her pussy as she stood there.  It was a spontaneous reaction as my tongue shot out and ran across her pussy.  She squealed on contact and then moaned as my tongue went to work and rolled her clit ring around as I worked on her pussy.

“Oh, you are a randy young man. Yeeees,” she groaned as I sucked her clit ring and clitty into my mouth.  She told me to keep going as she shook and then dropped back onto her chair breaking contact.  I wondered if she had come to her senses as she told me to get the next pair of boots.  It was a strappy pair and as I removed the previous pair, I reversed the teasing as my fingers stroked her pussy between removing boots.  She just groaned and then again as I put the next pair on, her pussy took some more fingering.  She staggered unsteadily to her feet and walked up and down a few times and then returned to the chair only this time she faced away from me and knelt on it giving me a fantastic view from behind of her smooth wet pussy.

My cock was rock hard again and with one quick lunge I was in her and up to my nuts in guts.  She was groaning as she thrust her pussy back to accommodate my cock.  Then we were pumping each other to see who would reach orgasm first.   Mrs. T……… did, she shuddered and shook as she squealed her way through her orgasm and her pussy squeezed my cock into coming just seconds later.  It was by far the best sex I had ever had.  I had fallen away from her and was now back on the floor looking at my cum dripping from her gaping pussy.

As she finally regained control, she informed me that I had now served my purpose and my services were no longer required.  As I straightened my clothing, she straightened hers.  Then she summoned the butler to see me out.  With the speed that he suddenly appeared I was pretty sure he had been stood listening at the door.  As I made my way back to the shop, I couldn’t believe that I had just fucked and older woman.  Back at the shop the manager took me to one side and told me that he had a call from Mrs. T……… and she was quite happy with my service and that she had authorised an extra bonus for me.  I felt used and dirty as I had just prostituted myself with this older woman.  The extra bonus helped me to forget that at the end of the month.

It was about six weeks later, and I was again struggling with my bills when the manager summoned me to his office.  I wondered what I had done wrong and was I about to be let go.  Instead, as he closed the door he informed me that Mrs. T…….. wanted some more shoes made for a holiday and this time I was to take the books to her home.  I could feel my cock stirring as he told me to go as she wanted me there as soon as possible.  As I drove to the house I wondered if I was to shag her again.  When I arrived, the same man let me in but this time he was dressed as a chauffeur.  I guessed he might be her husband.

It wasn’t long before I had at least one answer as I knelt on the floor taking measurements, that I really didn’t need as they were all stored on the company’s roller-file.  As before I had a clear view of her pussy.  This time there was just a hint of stubble as she hadn’t shaved for a few days.  That didn’t detract from my enjoyment or excitement at looking up an older woman’s skirt.  Then like before she pulled me into her pussy and my tongue took over as I explored her pussy and clitty again.  This time after she had enough licking, she had me hold her feet up by her stiletto heels as I slowly slipped my cock into her hot tight pussy.  I fucked her twice.  Once on her back on the chair as I held her feet out, and a second time in the doggy position as I had the previous time I was there.  Afterwards she selected two pairs that she insisted needed to be ready in four weeks for her holiday.

Then what I still guessed was her husband see me out in his chauffeur’s outfit.  He was red faced and I wondered had he wanked while I fucked her.  The manager was pleased with the order, and I was put back to work.  Four weeks later I was back at her house and this time her husband was dressed as a chief.  This time I was taken to her bedroom.  It looked clear that they had separate rooms as there was no male things in the room. 

Again, I was treated to the view up her skirt at her naked pussy as I tried the first pair on her.  I was soon buried in it, licking and sucking for all I was worth.  This time as I fucked her doggy style, I slipped a finger into her arse.  She squealed and groaned and then settled into a steady rhythm fucking herself on my stiff cock and finger.  Then to my utter surprise she groaned for me to put it in her arse.  I had fingered several girls’ arses but never actually fucked one.  I was surprised just how easy my cock slipped into her tight sphincter.  Then slowly I worked my cock all the way in.  Before I even started to fuck her to get to my own climax, she came loudly shouting, “Yeees, fuck my arse. Harder.”

Then she was gone into her own world as she shuddered and came.  Before she came out of her orgasm, I took my cock from her arse and fed it into her mouth, and to my surprise she was greedily sucking on it even though it had just come out of her arse.  Then as she recovered from her orgasm, she told me that I was a bad boy and to put it back in her pussy.  I started to slide in and out and then took it out and rammed it deep in her arse again.  Then I was taking turns between her pussy and her arse.  She was groaning constantly, wherever my cock was.  Then she was building up to another orgasm.  She insisted that she wanted me to stay in her pussy as she and I came.

Like before when she had fully recovered, I was told my services were no longer required and I was dismissed.  Her husband saw me off the premises.  Another good bonus arrived that month.  It was almost ten weeks later when I was again instructed to attend the house as she wanted shoes for a party.  This time her husband was in a schoolboy outfit and again I was taken to her bedroom. 

It was much like before, measuring then licking and sucking before getting down to fucking her.  This time she wanted to ride me, and she had me on my back and as she rode, I took her tits out of her top.  It was the first time that I had seen her tits and discovered they were a little bit floppy, but still enjoyed sucking on them as she took us into our first climax of that day.  Then after a bit of a rest she wanted me to fuck her doggy style.  She said that she didn’t want her arse touched as last time it had taken almost a week for her arse to fully recover.  I fucked her long and hard from behind until we both came. 

She called for her husband, who I will say looked ridiculous in his outfit.  I could see his eyes light up as he looked at his wife that had not bothered to cover herself.  He had a good view of her gaping pussy with my cum in it.  Then I was led from the house as she again dispensed with me.  Yet another good bonus.

A few weeks later we had another lad join us when one of the girls left.  He was like me a poor hard-up student.  Then I saw Mrs. T……… entering the shop and instead of making a bee line to me she went straight to the new lad.  I could see his hands shaking as he took measurement and looked up her skirt.  I suddenly realised that I was envying the lad knowing what he was seeing, and where I had been on several occasions, as had the manager and probably several other young assistants.  A few weeks later he was summoned to her home.  He was back fairly quickly looking quite upset.  I was upset as I had wanted to be there and not him.  I later overheard a conversation between the manager and the lad.  I had to laugh when I heard the lad come out to the manager and tell him he was gay and that he never wanted to see that woman again.  I heard that she had pulled his face into her pussy, and he had to fight his way back out and tell her that he didn’t like pussies.  Then he told her he was gay.  That ended her fun.

Two days later I was summoned to the house where I enjoyed every second of licking and sucking her pussy before fucking the daylights out of it.  Sadly, that was my last time as just a few weeks later I had my graduation from Uni and returned home shortly afterwards.  I often wonder what became of Mrs. T……… and did the lads taste of her pussy have a long-lasting effect on the poor lad.  As for me I had got a taste for older ladies and especially ones that didn’t wear any panties.  Besides marrying one, also with my wife’s permission, I service another friend of my wife’s who also went native most of the time.

I am now almost seventy and although the mind still wanders and enjoys looking, my cock no longer functions, but I cherish the memories of those days and the three older women that made my life such a pleasure.