I started receiving anonymous ‘dares’. Normally these would have come from my husband but this time they were really anonymous and I knew it definitely wasn’t David, he’s had suggested it outright. As you will know by now he would give me little dares to do and as the sexual side of things had progressed; these dares were becoming more challenging. But we had a system of when and why I would have to do a forfeit or dare. So I knew it was somebody who knew us quite well, I have always thought it was either my sister or maybe my Brother-in-law, but in fact it could have been any one of about 5 guys, who knew about the situation I was now into.
David’s dares were mostly (at this time) about me showing off, such stuff as forfeiting my panties and/or bra to go into work; going out with him to maybe a dinner party in leather mini and see thru top; going to a summer barbeque in a sheer thin cotton summer dress, of course in high heels and without any underwear in both cases.
The first couple of notes (by e-mail) and relatively easy, so I complied for the fun of it; It was my lunch break at work and I went to the local shopping centre on foot to fulfil my dare. I had received the dare a few days earlier; this was the third one so it wasn’t too much of a shock. The note detailed what he wanted me to do! I had re read it a dozen times getting myself wet each time.
As instructed, I was wearing 4½” stiletto heeled black court shoes with black hold up stockings with wide lacy tops; black panties, with black matching bra both lacy see through items. The instructions said a mini skirt, and knowing I would have to be pantieless later on I wore a skirt that was mid-thigh length, a white silk blouse completed the basic outfit. I also had a coat jacket as it was now getting pretty cold out there at the end of November. I had only been at my job for maybe 6 months so I was still pretty conservative in my approach, especially with David’s dares.
As I walked the 600 yards or so to the shops, I did find I was getting sexually aroused at my task ahead and with butterflies in my stomach. The public toilets are always clean at this centre (Mall) which did make it a bit easier for my dare, on the other hand leading now to Christmas the centre was heaving with people, particularly like me on a lunch break. The toilets are off a corridor and you turn either left or right according to your sex.
Taking a deep breath I turned right into the men’s room, to my horror there were 2 men already peeing into the urinals, their backs to me. One of the three cubicles was already in use. I hurried inside the centre one and collected my breath and nerves. Per my dare instructions, I now stripped off my jacket and blouse, skirt, bra and panties, noticing that the cubicle walls finished a full foot or so from the floor. The next step was the most difficult; I was to leave the cubicle and move to another one, leaving my bra and panties behind, carrying my jacket; blouse and skirt in one hand and not using them to cover myself in any way. I could hear men coming and going outside, and it seemed a busy place. I was just about to move with my clothing in my arms to the next cubicle, when I heard the door go click; I was in the middle of three cubicles and all now occupied. I now hung my clothes on the large hook on the back of the door and sat back down on the toilet lid.
The noises all around me were both intimidating and exciting, here I was naked in a gent’s loo, if either guy looked underneath, they’d see my slim high heels. I sat on the toilet seat itself to await one of them to leave. It was only then that I became aware of several large holes in each cubicle wall about the same height as my head. In both cases they were behind the toilet roll holder, which is why although the holes were quite large I didn’t see them at first. The other reason why I noticed them now was that my right hand side one had about 5” of pink semi erect cock poking through it.
For about 7 or 8 seconds, I just looked at it a bit stunned. Then very gently I reached out, almost an involuntary action and touched the penis. It was uncut and the skin was still almost covering the head, as my fingers closed around it, I felt it stiffen. The owner now pushed himself fully against the hole, so that nearly all his cock was through and almost his hairy ball sack as well. He was now almost fully hard and his foreskin almost backed off his helmet, a small blob of juice formed at the tip of his cock.
My fingers skinned back his foreskin and as my mouth enveloped his cock, I realised I was sucking on a cock of a man I could not see or know, a true absolute stranger. I could presume that he had peered though the hole and seen me undress or at least already undressed as he was the guy who was already in there when I arrived. Had he seen my spiky heels? My own pussy was juicing up. I had almost settled in my mind that this man must be the one who sent me the dare, was one of my lovers wanting to test me out.
At this moment in my time, I’d never been taken to a ‘glory hole’ by anyone, but I knew about them and indeed I had confessed to having a fantasy of being in one like a video/DVD booth and I sucked off several strangers. Like then I had no idea of the age or looks of my stranger, but in nearly every way that made it more exciting. This man’s cock tasted reasonably clean, I could discern soap on its skin. I did wonder if he was a regular at this sort of thing, I also wondered if it was he who’d sent the dare in the first place.
I knew we had to be quiet and so I could just about tell about 2 minutes into sucking him, he was about to explode. When he came it was in a couple of quite heavy spurts, maybe I shouldn’t have, but I did swallow and I continued sucking till he pulled away, by then quite small.
I sat back, feeling a little smug and more than a little horny myself now. I heard him leave and suddenly I wondered if he would ‘grass me up’ to any other guys out there. I also wondered if he’d hang around to see ‘what I was like’, of course I had no idea what he’d look like, but for him I would be the only woman coming out of the Gent’s loo.
No one immediately replaced him and I looked over at the other side, there was no cock sticking through there, and indeed I could see a guy with his trousers down pissing into the bowl, presumable the urinals were fully used. A minute passed and my eyes were still drawn to the guy peeing and he must have sensed me. I couldn’t see above his waist line, but my second cock of the day almost poked my eye out. Moments later I was sucking away, just like the first cock. This guy hadn’t showered that morning there was a taste of pee and sweat upon him, he also had a meatier penis on him, he had more girth and length came up hard fast, but he held his cum off longer. I settled into a rhythm, which lasted us nearer 5 minutes, before he spewed his cum in my mouth. His taste had fired up my own libido even more and I felt myself give a little climax, although I hadn’t touched myself as he spewed into my mouth.
I still hadn’t done my orders, and I looked at my watch, I’d been in the gent’s almost 20 minutes so far. I only had about 20 minutes left of my lunch break to complete my task, although as I sat there after my second guy, I was wondering if my dare wasn’t already completed. Perhaps giving a ‘blow job’ to a stranger was the real dare but he hadn’t said that in case it put me off!
Taking hold of my clothes again, I slowly opened my door. There were three guys in the loo, two using the urinals and one guy drying his hands, all had their backs to me, but I couldn’t see the whole room. With my breath in my mouth, three steps and I was inside the other one. There were no shouts of alarm or anything. I sat down on the seat. Now taking out my dildo, I started on my next step, my pussy was as wet as it has ever been without any touching, and my dildo sank in, like it was a knife through melting butter. I tried to mute my voice as much as possible, I came pretty easily, whilst keeping an eye on ‘the hole’ if another one was poked though it would definitely get the same treatment as the others.
But nothing happened, and I could tell by the noises that the toilets were now virtually empty. I redressed in my skirt, blouse and jacket – as instructed I left my panties and bra hooked on the cistern knob, clearly for the next man in to see. I glanced at my watch I’d been in there nearly 35 minutes now and my lunch hour was rapidly disappearing.
I peeked out again this time there were only two men, I tried to walk as quietly and quickly as I could out the door, One guy turned and our eyes locked for a moment, before I hurried out the door. Outside in the corridor I was looking out to see if anyone was paying me special attention, well I couldn’t discern any.
Back at work, I pondered my adventure. It had been exciting; I was still very horny and pretty impressed with myself for doing the whole thing. Being at work without a bra and without panties on wasn’t entirely a new thing for me, as my husband had already dared me at least a dozen times to come to work here without underwear or just minus panties in especially short skirt, but this would be my first afternoon like that. The light blouse did reveal my nipple outline a bit, but nothing too obvious or so I thought. It was only three weeks later when my new boss made a successful pass at me, did he admit he’d noticed I’d ‘lost’ my bra and panties over lunch that day. Later on he admitted that during my interview with him for the job, I’d given him a real ‘Sharon Stone’ moment I hadn’t even realised, again that was a David dare.
Who sent me the dare? I wasn’t 100% sure – it would be almost 9 months before I found out.
Christmas
I worked as a PA to a director in a small insurance office. Our office is on one floor of a small modern office block 4 stories high, right on the high street and on a corner, so 3 sides of the office has windows (front; left side and rear). The other three floors are used by various companies; we share stairwells and lifts with them. On the ground floor with have a small office for dealing with the public. Around the rear of our office across a back alley, is a 3 story public car park where most of us park. Most of us use the rear stairwell to come and go. My Boss’s office is located at the rear and left so he has windows on those sides, not overlooking the high street, but the road that runs along it and the back alley way.
Although I’d been working there a few months; Tim had only been my Boss during that time, after his PA went off on pregnancy leave I was asked to take over. He was a slim, quite good looking chap in his early 50’s and usually quite shy. That seemed to change over the course of 2 days, due to 2 parts. First in the afternoon of my ‘Gents’ loo’ dare, I had been naked under my short skirt and also under my thin jersey top, as my panties were left behind in the toilet and my bra was in my bag. I know now that in the course of the afternoon, I had given him an eyeful of naked pussy at some point.
Then 2 days later was our office Christmas lunch, we have about 20 staff; of which 8 are guys, the girls dressed up a bit and we go to a lovely Italian restaurant for lunch and afterwards back to the office for coffee to sober up as most have to drive home, or like me were collected by husband. And that’s where he came in. You see my husband, David choose what I was to wear to the party. Black sling back 4½” high heels with diamante straps, black stockings hold-ups; a red and black sheathe dress off my left shoulder, the hem reaching my knees, but with a dramatic slash almost to the hip on my left leg, a diamante necklace – and that was it — no underwear.
During the past months I’d been into the office without panties and sometimes without any underwear several times; most times, all down to my husband’s dares, but not always. I wasn’t aware but my Boss had ‘seen’ me accidental flash on a couple of occasions.
I wouldn’t state that I was the best looking woman in our office, because there are a couple of young girls who are very attractive. But I got a definite increase in Tim’s looks since my accidental flash. Then after we returned to the office still fairly flush with drink, the others drifted off, it was getting towards Tim and I being the only ones left.
In the past year, as I have already confessed I had had sex with two of the guys working there, each on his own and each a married man, in both cases it had been very casual, in one case sex was instigated by me, in the other case by the guy. With one of those guys, Tony I had also engaged in a threesome firstly with my husband and at another time with his wife, this had been repeated on both counts about half a dozen times. The other guy, Matthew had been ‘seeing me’ a couple of times a month; when he found out about our sexual life style was keen to fuck me with David watching, which initially he did once a week with us then after about 2 months that reduced to about once a month, although on average like the other chap I was having sex with him once a week.
Before leaving, both Tony and Matthew had separately pulled me into a room for a good long kissing session, where each had felt me up and to save it from ruin, I had slipped out of my dress and blown each guy (and swallowed) whilst kneeling in front of him. Matthew, being what he is, and what he knew about me, had also done a long slow pee down my throat (I’d expected that, hence the removal of dress). Both guys had licked my pussy, but whilst I had achieved a small climax, it really only kept the fire burning.
Having done the servicing that I thought I’d do that day, I phoned David, my husband to find out where he was. He was still at home, he wanted to know who was left; I told him about 4 or 5 of us. David told me to ask Tim if I could use the phone from his office as my mobile had a bad connection; Of course he said yes. I went in shut the door, following my husband’s dare, I unhooked my dress, let it fall to the floor and stepped out of it, laying it on a chair, I phoned David back, standing beside my Boss’s desk wearing just my high heels and stocking and leaking juices. This was a typical David dare; I knew he would want me naked like this for several minutes. I didn’t think Tim would come back in too soon; he was busy talking to the others as I came in, I appreciated the excitement of my situation, and I was very hot.
David wanted to know about Matthew and Tony, so I told him in fullest detail, knowing he had his cock out. A couple of minutes or so passed and David was still talking to me, I was just asking David how long I was to stay naked, his reply was ‘10 minutes from now’, I was about to say that was too long to stay naked in his office, when I could hear people saying goodbye quite loudly and for a moment I feared one or both of them might stick their head around the door to bid me a good Christmas. There was only one place of refuge for me to bolt to and telling David my predicament, I put the phone down just as I saw two shapes outlined against the frosted glass of Tim’s office door.
Sure enough some 20 seconds later, the door opened and two of my colleagues a guy and a girl pushed their heads around, I was stood behind the largest filing cabinet, my head and shoulders in view pretending to talk on my mobile phone. I was leaning on my elbows on the top of the cabinet. My heart was racing, if either or both came in fully to the room, I was sunk, because they’d see my dress on the chair and halfway across the room, I’d be revealed. I pretended that I was speaking and waved and blew them a kiss and they both left. My heart was hammering away.
I wasn’t sure now if Tim and I were the only ones left in the building. As I walked back across the office to Tim’s desk, I heard a phone line ringing and the second light on the panel was flashing. I picked up the line I had been speaking to David on, it was dead, and the second line was still flashing and ringing outside, I pressed the button – I must have been a fraction of a second too late as I heard Tim’s voice answer the call, it was David my husband. They’d met a couple of times and I heard them exchange the usual pleasantries.
I wanted to hear whether my husband was going to drop me in it. Barely half of my 10 minutes had passed. Would he tell my Boss that I was standing naked in his office? I doubted that he could pass up the opportunity, but I wanted to hear him actually say it outright. Just then my mobile phone started ringing, I quickly pressed ‘mute’ on the line to David and Tim.
My cell phone call was from Sally the woman who’d just left. I knew as soon as she spoke that she’d not been taken in by my hiding antics. Not only had she seen my dress lying on the chair, but my reflection on the glass behind me. I knew that she was down in the lobby with Martin the man she’d left with, who was probably hearing this as well. Martin was the guy half the office knew she was sleeping with, in spite of her having a nice looking husband, and he was almost 8 years her junior at 22 years of age. Martin who’d made several passes at me, which I had turned down. Mostly because he was clumsy with them.
“Are you still naked?” She asked of me, I said I was.
“How long are you going to wait?” I looked at my watch, ‘another 4 minutes and 30 seconds’ I said, which confused her for a moment or two.
“Oh gosh, you’re on dare or a bet? She asked “A dare!”
“Oh wow, lovely” she exclaimed, “from David?” She sounded as excited as I was feeling, especially when I said yes. Somehow talking to Sally had if anything turned me on more, knowing that she knew my predicament had added another element to the situation. I had tried not to, but now I was using my fingers on my pussy.
“Was Tim on his own when you left” I asked.
“I’ll tell you if you walk to the window facing the car park” I did so, knowing exactly what she had in mind. I stood right up at the window, Sally and Martin standing on the pavement outside the car park were looking up at me on the second floor. They could see my nakedness from my hips to my head. There weren’t that many people about, but it was now dark outside and I had a light on behind me so I was framed. Both of them looking up would or should make a few others look up, certainly anyone leaving our office block, those passing by on the road didn’t pose much of a threat.
“Well” I asked, “wait a moment” she replied, letting a guy walk past her. Then she parted her coat, she was naked but for her boots underneath. The dress she been wearing to the party was gone, I realised that she hadn’t had enough time to slip out of her clothes as we’d been speaking, so it wasn’t planned for me. She was just showing me, that she was up to no good as well.
“You like?” she asked “Yes “I said, my mouth was dry, she did have a good body on her, my voice was giving away my reaction and she caught on.
“Is your husband going to tell Tim to go into his office and catch you”? She asked of me, I explained that it was highly likely. It occurred to me that Matthew or Tony might have been poking Sally as well, in which case she’d likely know most of the stuff about me. After all she didn’t seem that surprised.
“Is he (my husband) going to get a kick out of Tim seeing you naked or Tim fucking you? She asked,
‘A bit of both’ I said.
“Are you very aroused” she asked,
“Yes, I’m quite wet” I admitted.
“Are you turned on by the idea of Tim fucking you in his office”? —
“No, more the situation, the dare, you finding out, rather than the actual sex”.
“So it could be any guy out there in the outer office, right now, the excitement for you is that there is a man there and you are one unlocked door away and naked” She was 100% right.
“Okay, you did my first dare – Tim was still there with Robin, when we left, I think he is going to give Robin a lift to the station. I’d completely forgotten about Robin, he was our teenage office boy ‘so to speak’ taken on in the holidays for work experience, spotty, unsure of himself; and about 15 years old. He worked a few weeks in the summer and then these two weeks before Christmas.
“Will you accept a second dare from me Sally asked?
“Maybe, — what would it be”
“Walk to the door of Tim’s office and opened it and leave it open, then come back to where you are now” she said.
Tim’s office opened right into the main open plan office where most of us worked. Most of the people had been gathering over on the far side of the office where the coffee and cakes were, and even with the door open, they couldn’t see much inside his office, but Tim had walked to a phone on a desk and maybe still talking to David. About another 4 minutes had passed.
“Okay, but you must do a dare as well at the same time”. I said.
I tried to think of something imaginative. I couldn’t so “take your coat right off and give it to Martin to hold” it was the best I could think of.
There wasn’t any hesitation, no furtive look around or anything, she just did it.
So I did my part, luckily for me the door opened inwards. I knew, as did Sally that the odds of Tim coming in now were greatly increased. I walked back to the window, she was still standing there naked but for her boots, in exactly the same position, she hadn’t even stepped back into the shadows, like I would have done.
Sally and I faced each other. I picked up my cell phone “Now what” I asked. David’s 10 minutes would be up in about 90 seconds, I was honour bound to stay naked until then, beyond that was up to me. I looked at the phone console, there were no lights glowing, so David had just finished his conversation, because when I walked to open the door it was lit up.
Sally was just about to suggest she phone in the office, when I became aware of a presence behind me. It was my Boss Tim.
“I’ve just been speaking to your husband” He said behind his arms coming around and cupped my breasts. “He said you were in here with my Christmas Present”.
Sally had seen what was developing and gave me a big wink as she turned to Martin to get her coat back. So enwrapped in what was happening in the office she had failed to notice Robin emerge from the rear doorway. Before I turned to face Tim, I saw Robin do a double take on Sally’s naked body.
I turned and offered my lips to Tim and he embraced me in a long tongue kiss. When we broke from the kiss, I asked
“What else did he say?”
“Well, I thought he’d been drinking, but he told me you’d be in here just like this, ready, willing and eager”
And so starting with as a prolonged oral job on his quite delightfully uncut prick; which took 20 minutes before I let him spew into my mouth and swallowed it down. He admitted that it was his best blow job ever and the first in almost 25 years that was swallowed.
After that he fucked me in several positions and in several places around the office for the next three hours. I got home full and horny for David about 9pm.
****
I had never intended to keep a score of the number of my lovers; my sister had almost correctly guess that my pre wedding gang bang would double my tally, but she was a few short – It should have been 22 to double, but after the few affairs and that dinner-dance and attention from my husband’s former work colleagues, I was near 100 at Christmas 2009. More over in 2009 I had been sexually active with over 60 lovers. Whilst I wasn’t getting bored by this, I was getting bored by the more straight forward sexual encounters I was having. The excitement was in a new lover or trying something kinky.