The best place to start is with a brief introduction, my name is Ron, 35 years old, married to Courtney aged 32, for a very happy nine years. We have no kids, medical reasons, and are both in sufficiently well paid jobs. Quite usual considering nine years of marriage, our sex life remains adequate but is getting more of a routine pleasure rather than fantastic. We were very good friends and neither of us felt sex was a problem but one event led to better things.
Things started with a fancy dress function at the small members club we use about once a week. The cheese and wine party poster specified all members wear fancy dress, neither of us were keen, but we thought we had better support the function. A few nights before we were sitting watching the television and discussing what to wear, it ended up with me dressing as a pimp and Courtney as a whore. The only reason those characters were chosen is because we were watching a film which featured a hooker being murdered.
We had no idea what a pimp dressed like but I ended up in a black jumper, black trousers, and a black great coat Courtney picked up in a charity shop. The only other attempt at looking the part was taking a cheap gold medallion off an old belt of hers and fixing it to a necklace.
Courtney has a perfectly proportioned body, she is 5' 7" tall, most of it leg, with long straight natural blond hair. She wore a simple tan coloured crop top over a 'push up' bra – not necessary because she still had very firm breasts for her age but it created a superb cleavage. She wore her shortest denim mini, I am not sure she had worn it since she purchased it several years earlier. The sluttish final touch was a pair of clear plastic platform stilettos, real porn star stuff that she had worn for me in the bedroom occasionally.
It was a pleasant evening, we both had plenty to drink and eat, and most of our friends were there to chat too. Courtney always stands out at the club as being among the most attractive members but that night she was easily the best. Courtney enjoyed all the attention, and the comments her attire attracted, most of the men there jokingly asked how much she charged for some action.
When we got home, we were both all over each other as soon as we got inside; I stripped off on the way upstairs but told her to keep her gear on. She took my very rigid cock into her mouth as soon as we were on the bed and gave me some excellent attention. I pulled up her skirt and sunk a couple of my fingers into a very moist pussy. We sorted ourselves into a classic '69' position and I sucked her to a very good orgasm in a very short time.
Changing position, we then had a quite frantic 'missionary' fuck much to our mutual satisfaction. Snuggling up to go to sleep and she said, "You seemed to like using your whore." The sex was amongst the best for a long time although some action after a night out was usual we were both more enthusiastic that night.
Other than waking up to a nice kiss and mutual thanks we said nothing about the previous night's activity. We both got up late and did our usual Saturday chores including the weekly grocery shop. Things took an interesting turn at bedtime when she told me to wait downstairs until she called me. After a while, she called me up and the sight of Courtney dressed in her whore outfit greeted me. She smiled and said, "Hello sailor, how would you like to use your whores body this evening, most things are on my menu?"
I thought what a nice offer and replied," Can I afford to use your ass, I have not had the pleasure for ages."
"Of course you can, as its you I will even allow you in bareback, there is some lube on my bedside table, just leave fifty pounds behind, I have a special introductory offer on today." I still had my wallet in my trouser pocket so I counted out fifty in ten pound notes and put them on her bedside table. I applied plenty of lube to my suddenly aroused cock as she jumped onto the bed and laying on her back with her legs held apart. "Come on, get in here, time is money to us girls you know."
As she said that, her hand went down and she spread her pussy lips apart with her fingers, using the middle one to rub her clit. We were used to anal but did not partake very often, when we did it was usually at my request. While still working on her sex she used her other hand to guide my cock against her puckered hole. She pulled some of the lube from my cock and worked it in to her ass with a finger and said," In you come, as hard as you like, you are paying."
I gently pushed against her hole, which gave way without much effort, and I slipped a little way in. She lifted her legs, still wearing her slut shoes, up around my waist and pulled me in further. We soon had a lovely rhythm going with me giving long strokes as deep as I could go with her full cooperation pulling me in and yelling 'yes'. She did manage to orgasm some times when we had anal but this time she was well away, aided by her own finger action.
I all too quickly dumped my load well into her bowels and slumped down on top of her, we were both nicely shattered. I asked, "Is there any chance of an overnighter or must I leave now?"
She said, "Thank you that was good, lets cuddle up and go to sleep after I get out of my working gear."
In the morning I woke up to the extremely pleasant sensation of her lips and tongue working on my, obviously rigid cock. Not a first but a very rare way for her to wake me up, I said. "This is nice, but can I afford it?" Her answer was to sit astride me and sink my cock into her pussy and start humping away, I just grabbed a bouncing breast in each hand and matched her rhythm.
We both achieved very satisfactory climaxes as good as simultaneously and after regaining her breath, she jumped off and said, "Dressing up seems to have put some life into our sex drive, I think we should go shopping for some more gear later, I seem to have some spare cash here beside the bed. What do you fancy, sexy nurse or maybe school girl?"
"This has indeed turned out to be a fun weekend, as to how to dress your sexy body I am all in favour of the 'If it isn't broke don't fix it adage', lets see if we can find some more whore gear."
A very unusual experience for me, I actually enjoyed three hours wandering from shop to shop, we both maintained a sexual mood all the time. She spend considerably in excess of her 'earnings' but I told her it was no problem she had plenty of earning potential and would soon get her investment back.
Our purchases included a pair of shiny black stiletto boots with very pointed toes, and a pair of tarty slip on mules with even higher heels. Three skirts, a denim mini and two ridiculously short micro skirts, one blue denim and one white leather. As it was a Sunday not all the shops were open, so we had to forget a few ideas, mainly corsets and underwear, but we did find several revealing tops and a short denim jacket.
We also found a pair of very large gold hoop earrings and although she does not smoke, I insisted we bought her twenty long cigarettes and a cheap lighter, because all whores smoked. Courtney was even keen when we found a beauty salon open and I suggested she went in and had a full trim and waxing down below.
She was lucky, they could do her right away so we arranged to meet at a nearby café when she was finished. I struggled in with all the purchases and settled down to wait with a coffee and a couple of cigarettes. When she came in and found me, I bought her a coffee and she said, "I think it's time we went home, I am feeling all tingly down below and want you to fuck me." She was still dressed in her nice tight jeans, heels and a tight white jumper but I had an idea.
"How do you feel about the idea of going into the toilet and changing into some of your new gear now?" She agreed to do so if that is what I wanted but said she was not very keen on delaying some action. We selected the outfit and off she went to the toilets, I toyed with the idea of just leaving a note on the table for her to find on her return. I thought better of it and decided to propose my idea face to face, I did not want to upset her new mood.
She soon returned wearing the black boots, denim mini (not the micro), tight yellow top showing lots of cleavage, and the denim jacket. She had also applied heavier makeup and was wearing the new hoop earrings. I got her to sit down and light up a cigarette and said, "Would my sluttish whore like to find her own way home on the bus, it would give any fellow passengers a thrill?"
She smiled, "OK that sounds like it could be fun, I do feel very sexy."
I risked pushing a little further and said, "I expect you need to nip back into the toilet to take off your thong, unless you have already?"
Courtney blushed slightly and said, "Hey, that is going a bit far, I had that done for your eyes only – although why not, as I said I do feel randy – yes I will." She got up and I watched her sexy body sway off to the toilet again. While she was in there I sorted out the bill and we walked out into the street together. We had a kiss and cuddle although she pushed my hand away when I tried to get under her skirt to feel the new smoothness.
She said, "See you later darling." I stood and watched as the hooker walked off down the street, her hips and ass swinging.