Thread: [Non Fiction Stories - Voyeur] Upskirt stories
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Old 05-19-2024, 10:56 PM
Lucky_doug Lucky_doug is offline
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Default Teasing the Boss

I am a 100% confirmed lover of upskirts, seeing up women’s dresses, and catching an impromptu or candid glimpse up their regions. I also like watching my wife perform in public when we go out for a night, to a restaurant, bar, or to catch a show. She will doll herself up, apply makeup to really look the part, and wear a sexy short dress or skirt to turn men’s head’, and even a few women. I always encourage her to dress really sexily and raunchy so that she will attract attention. Not like a sl*t but with class and style. If she’s in the mood I’ll even suggest she forget to put on panties, or at least wear a minimalist thong, to ‘keep them interested.’

To her credit, she loves to play along, and does not feel in the least bit taken advantage of. She has retained her figure despite having three children, her legs a well-toned, she has a smooth stomach, and a butt many women ten or more years younger would kill for. As such she has always enjoyed wearing short skirts, dresses with a long slit up the side and provocative tops that enhance her cleavage and invite looks. She is a natural brunette and has lustrous hair, which she does up beautifully when we go out. In total, she is still a knockout!

We try to go out at least once a week, the kids are old enough to look after themselves, so this is not an issue. I don’t really need to encourage her as her playful spirit automatically gets her to accommodate my wishes. We like to choose restaurants, parties, and similar venues where there are always lots of other guys looking. It's by far one of my and her biggest turn-ons. She is fully aware she turns heads and is OK with being stared at and the object of lustful looks. When wearing such short or sexy dresses it’s hardly surprising that she will inadvertently be occasionally indiscrete and allow her legs to spread just a little too far so that some lucky gent will get an eyeful. She also likes to tease me my deliberately parting her sexy pegs for me to inspect her, especially on those nights she goes ‘commando’.

As a side note, I know she likes to keep her pussy totally 'shaved' and smooth, which, I think makes it all that much naughtier, if not 'exciting' when someone catches a glimpse. Not to mention I enjoy eating her out much more when she is freshly shaved, and she says the feeling and sensation she gets is out of this world!

A few years ago, I began encouraging her dress this way, within acceptable limits, even at her work. She works in a small office where there are just a few girls and all the rest of the staff are men, her boss included. Ironically, he's the biggest perve of them all, and I think he has deliberately relaxed the dress code so she and the other girls can follow suit. Let's just say she has never been called into his office for wearing a skirt that was too short! He regularly compliments her on what she wears, even though, in today’s PC environment that could be considered sexual harassment. This is certainly the case if it's really 'short', making it all too clear what he likes. And though she's told me he can’t help himself, always looking at her legs and stealing glances up her skirt as she moves around the office, he's otherwise actually totally harmless, being a committed family man with genuine loyalty to his wife. But his personality makes for a fun atmosphere to work in, which fortunately pleases my wife no end. I have to admit I rather enjoy that setup as she frequently comes home so horny and worked-up we often have to have a ‘quicky’ before she starts preparing dinner. It goes without saying, that what follows has also enhanced our sex life.

A specific occasion comes to mind. I had been encouraging my wife to tempt and tantalise him in the office, giving him plenty of opportunities to ogle and perve on her. I knew shew would not let things get out of hand, and having met him, myself, I felt sure he was just in it ‘view and not touch’.

She was a real dear, not to mention a tease. She was as eager to play along as I was to hear a running report of how things had gone. I also knew her boss would appreciate it too, so it was a win-win situation.


I also like to ‘help’ her get dressed in the mornings, making small suggestion to tweak her sexiness, when I know she is in the mood for a tease. I love watching her choose and put on her sexy lingerie, her panties, thongs, or bikini briefs in a variety of colours and styles, not to mention the ridiculously erotic bras she has. Stockings, stay -ups or with suspenders add another dimension to the eroticism. Of course, when she slips on her f*ck-me heels, that is the icing on the cake. This really gets me going, and there has been a string of days she has turned up late, simply because we had to have a quick f*ck before she left, both for her benefit and mine.

The thought that she is doing this for someone else adds an edge to the whole scenario, makes the sex all the better, sharper, and fresher. I believe that my wife is so sold on this play-acting, not only because by nature she is a bit of an exhibitionist and likes to deliberately tease other, but she also realises how much I get turned on by it. In fact, I think her acting out this role at work has added a bit more excitement to our sex life. I just love knowing she is sitting at her desk with my horny boss hanging around it while she’s not wearing a thing under her short skirt, which he knows creates all kinds of possibilities and it's all too easy for her to be naughty which she frequently is!

As for her 'boss', the first time he noticed, I almost had a coronary! I know she gets along with him better than ever now, as they both know what this is about, and know their boundaries. He knows it's quite okay to 'look', as I admittedly find it all rather 'exciting' when she regales me of what happened that day, when she gets home. He also realises that it's not okay to get carried away with his 'hands'. As I now work nearby, he and I now carpool together, with him picking me up in the mornings, dropping me off at my workplace about three days a week. We also go out to lunch every Friday. On these days I'll pick out what she’ll wear, and of course, as you can imagine, I always pick out something that’s super short!

She tells me there are days when she’s feeling especially horny, she’ll be really naughty and behave or sit in a very unladylike manner at her desk when he wanders past, as he does quite frequently, in the hope of a clandestine glimpse of her legs or more. He will also take her out to lunch, hoping to see ‘more’ of her. He’s always the gentleman, opening the car door for her, of course, there is an ulterior motive here. Any woman in a short skirt is at a definite disadvantage when exiting a car, especially if it is a low-down sports-car like his Lamborghini. Naturally, I am eager to hear all about her exploits when she gets home, and if she’s been really 'bad', she’ll be so aroused and already wet that she virtually jumps me as soon as she gets through the front door. I love it, and it goes without saying her boss can't get enough of it either! I hear his wife is pregnant again with their third. I wonder how that happened?
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