The adventuress and the watchman
written by:
Drew Pleasance

Lesley was the office manager of a large regional accountancy practice, a relatively minor client of the design agency I own. Most of my dealings were with the company's marketing manager but, because I called in on them on a semi-regular basis, I would often also see Lesley going about her business. Our interactions were never more than friendly and professional, and yet from the moment I was introduced to her there was something about her that ensured that I would always scan the offices and corridors to see where she was. She was impossible to ignore. I guessed that she was around 45 years old, only a few years younger than me. She was attractive, and very curvy, with large breasts that swayed gently when she walked, and quite stunning legs. It was her smile, however, that first grabbed my attention. It was utterly infectious. When she smiled at me it completely lifted my spirits. On more than one occasion I also I detected a definite twinkle in her eye, as if she were concealing a more irreverent attitude than befitted her rather stuffy surroundings.

She stood out among her work colleagues, most of whom were either young professionals or crusty older men and women. Lesley somehow managed to slot in neatly between them; always immaculately turned out, yet with an undeniably sensual air about her. I'm just shy of six foot tall and she was about a head shorter than me, even in high heels, which she wore most days. She invariably favoured business suits, with fitted or wrap-around skirts and tailored jackets, but in warmer weather she swapped them for floaty summer dresses. If I couldn't resist searching for her whenever I visited, I also couldn't help but notice that she in turn always seemed to spot me, and smile.

On one occasion I turned up for a meeting at around lunchtime and, noting that the receptionist was busy elsewhere, she offered to make me a coffee. As she placed it down before me on the low coffee table she leaned forward, giving me a perfect look straight down her blouse. Suddenly I was staring at two large orbs enveloped in white lace. The sight of them hanging before me like ripe fruit, together with the intoxicating smell of her perfume, caused an immediate twitch in my lions. Out of politeness I quickly looked away. She would later tell me that her actions had been completely innocent, but that she'd realised what she'd exposed when I looked away, and had warmed to me further as a consequence.

A few weeks later I was sitting in my car in the visitors' car park, finishing off a phone call. It was again around lunchtime, and staff had to walk past me to get to the front door. It was a windy day and many of the women had to hold down their skirts to prevent them from blowing up. Just as I was finishing my call Lesley appeared from around the corner, dressed in a black wrap-around skirt and matching jacket. A sudden gust of wind took her completely by surprise and her skirt opened up to reveal a shapely stockinged leg, topped by a dark band and the clip of a garter belt. As she deftly smoothed her hand down to close it she looked up, as if to check whether anyone had seen her. I was parked right in front of her with a grandstand view, so there was little way of disguising it. As she saw me through the windscreen there was an immediate flicker of recognition, and then ...a wink. Five minutes later I'd followed her inside. By then she'd returned to her desk, but as I walked through the office to the meeting room I again caught her eye, and this time was rewarded with a knowing smile.

My life at the time was fairly - empty. I'd lost my wife in a riding accident nearly two years earlier. One minute she'd been there, the next she was gone. We'd been married for almost 20 years. My two teenage children and I had come to terms with our grief together and separately, and were now just getting on with our lives - in my case in a kind of empty bubble. The kids had boyfriends and girlfriends. I found myself as a middle-aged singleton, not yet ready for another relationship, but not wishing to put my love life on indefinite hold either.

The truth was, I was horny.

When news of my wife's accident broke I'd been astonished at the speed with which some local divorcees had made their availability plain. Some continued to quietly stalk me. Initially, of course, it had been the last thing on my mind. More recently I'd found myself questioning what the harm would be in enjoying what was so blatantly being offered - but I could do without the attendant complications. A one-night stand was one thing. What I didn't need was for a single night of fun to be the prelude to series of dates and expectations. So I continued on alone.

Until one day I stopped by the local Indian restaurant on my way home, to collect a take-out. The kids were out with friends and I didn't feel like cooking for myself. As I walked in I saw Lesley with a guy I knew called Chris, another local business owner whom I'd met on several occasions at networking dos. They were sitting together at a table in the restaurant section, chatting away animatedly. Lesley spotted me first and smiled broadly. Chris then looked up and, also recognising me, waved me over.

"Eddie, this is my husband Chris," Lesley said, before Chris revealed that we already knew each other. After exchanging a few pleasantries they asked me what I was doing and, upon hearing that I was planning to dine alone, immediately invited me to join them.

What might have been an awkward situation turned out to be anything but. My suspicions about Lesley's impish sense of humour were right on the money. The conversation flowed freely, and as more and more alcohol was consumed, so did the gossip. It helped that we knew many of the same people. We covered who was having trouble with whom, who was dating whom, and finally who was cheating on whom. Lesley and Chris were aware that I was widowed and, with inhibitions lowered and Lesley apparently in a playful mood, it seemed almost inevitable that the subject of my love life should eventually crop up. I shared with them my experiences of trying to keep a particularly persistent, and voluptuous, local divorcee at bay. Lesley practically shrieked with laughter, her own breasts jiggling enticingly. She pressed me for more and more details, including the names of all those who had propositioned me (not that long a list, but I hammed it up a little for effect). By this time she was flirting with me quite blatantly, while Chris smiled on indulgently. It was quite endearing to watch, as she'd regularly touch him on the sleeve or hand, as if to reassure him that she was still his. If he was irritated by the attention being lavished on me, however, he showed no signs of it. Instead, he seemed genuinely to be enjoying her obvious pleasure.

"So, is there anyone who's caught your eye, lately," Lesley asked, with a definite twinkle in her own.

Right then I was having trouble tearing my eyes away from the swell of her ample breasts, hidden beneath a sheer cotton blouse, and the fragments of a lacy bra I kept seeing between the button holes.

"No," I answered frankly, before adding recklessly, "I'm certainly up for a quick shag, but I'm not yet ready for another relationship."

Lesley and Chris both seemed to stiffen slightly, and I suddenly felt myself sobering up fast. I wondered whether I'd misjudged the mood, or the company. To my relief Lesley burst into fits of giggles. Chris returned to smiling contentedly.

"Well, perhaps we can do something about that," Lesley said, looking me straight in the eye.

Now I may have been out of the dating game for a while, but there was no mistaking that as a come-on. A handful of less-than-subtle divorcees may have reminded me how to spot the signals, but Lesley's look and tone left little doubt as to what she meant. Little - but still some.

"I ...don't know how to interpret that," I said hesitantly, looking from Lesley to Chris and back again.

Lesley leaned forward slightly and lowered her voice to a conspiratorial whisper.

"Well, how would you like to interpret it?" She answered slowly, with a mischievous grin.

I looked at Chris. To my surprise he raised his eyebrows as if to say, "Well? How?"

For a moment or two we sat in silence.

It was broken by Lesley who, still smiling, turned to Chris and announced, "I need to powder my nose". A little unsteadily, she got up to leave the table. As she did so I caught another glimpse of her cleavage and a waft of her perfume.

For a moment or two Chris and I continued to sit in silence. I didn't know what to say. He continued to smile enigmatically. Eventually he piped up, "Lesley likes to be adventurous." There was a short pause. "And I like to watch."

Well this was new territory. I continued to sit in silence, trying to comprehend the full significance of this sudden turn of events. Part of me was attempting to stay grounded and to convince myself that I'd misread the situation. The other half was in no doubt. I had just been invited to have sex with Lesley, while her husband watched. The prospect of him getting involved suddenly brought me up short.

"I'm not bi-sexual", I said simply.

"Nor am I," said Chris quietly. "Although I'll probably get naked." There was another pause. "I stay in the room, but it's your and Lesley's party."

Wow. That was clear enough.

Suddenly, the magnitude of what was being suggested hit me hard. Was this perhaps a set-up?

"No cameras," I insisted.

"Absolutely no cameras," confirmed Chris, in a tone that suggested it was the last thing he wanted either.

Minutes later Lesley returned from the bathroom. She was weaving slightly, and as she manoeuvred past me to her chair she put a steadying hand on my shoulder. I looked at her hard to work out whether she'd been too happy, too carried away, or just too plain drunk to be serious. But as she sat down she looked straight back at me, a little smile curling up at the edge of her mouth. I wondered whether we'd be heading home together that night or would get together when we were all a little more sober, and less little full of spicy food...

"We should probably meet again for dinner," she said simply, making it clear that she favoured the latter.

As we parted ways Lesley squeezed my arm and gave me a very gentle kiss on the cheek before linking arms with Chris and heading off into the night. I walked back to my place practically in daze. That night I didn't get much sleep. Images of Lesley in her business attire were replaced by images of Lesley dressed as she had been at the restaurant, of her unbuttoning the blouse she wore, of the lacy bra beneath. Of her taking it off...

The next morning Chris called me and suggested that we meet four days later at a local Italian restaurant.

To say that I found the wait distracting would an understatement. Thoughts of Lesley in various stages of undress were never far from my mind, day or night. Lesley in a lacy bra and panties, Lesley bending over in stockings and high heels, Lesley sucking my cock. I spent most of the time with a permanent erection.

Eventually, the hour of our meeting drew near and I walked round to the restaurant, only several blocks away from where I live. Chris and Lesley were already there. When I saw her I couldn't help but take a sharp intake of breath. She looked stunning. She'd gone for quite a demure outfit: a pencil skirt, silk blouse and the usual high heels. She'd tied her hair up, however, and was wearing clear lip gloss. The effect was unbelievably sexy. Two buttons opened at the top of her blouse revealed an inviting cleavage and the white lacy fringe of an undergarment. As I walked in she smiled coyly. Clearly, she was as nervous as I was. I sat down and the waiter came over to take our order. I wanted something light and so ordered pasta. I noted that she ordered a light pasta dish too.

Surprisingly, despite the obvious sexual tension, our mood soon picked up from where it had left off. Chris seemed perfectly happy in his role as chaperone, the conversation bounced easily from topic to topic, and when the voluptuous divorcee I'd mentioned earlier walked into the restaurant we all burst out laughing. Fortunately, she didn't see me and remained oblivious.

Lesley seemed a little preoccupied. Flatteringly, she never took her eyes off me. She occasionally still touched Chris' arm, as she had done in the Indian restaurant, but it was apparent that her attention was entirely focussed on me. I was sure that it wasn't coincidental that she kept licking her lips and lightly brushing her décolletage. The effect on me was electric, and in no time my dick was straining hard against my pants. I wondered how I was going to get out of the restaurant without attracting comment.

As the meal came to an end we again grew quieter. I offered to pay the bill, but Lesley and Chris insisted we split it. I'd somehow managed to get my cock to go limp - well, limp enough not to show too much - but once we were back out in the cool night air and Lesley took my arm on one side and Chris' on the other, the weight of expectation and waft of her wonderful perfume hit me again, and I had to do my very best to walk down the street while concealing a giant boner.

It wasn't far to their place: a lovely townhouse with high ceilings and large windows. Soft lighting had been left on, and as we walked in we were all silent. Chris turned and mumbled something about letting the dog or cat out. I guessed that he was giving Lesley and me a little space. I knew why we were here, but wasn't sure how clinical this was going to be. Should we kiss? Show one another affection? The last person I'd slept with had been my wife, and before that a girlfriend in college. As if reading my mind Lesley turned and gave me a long, lingering kiss on the mouth. We kissed again. Then she fell into my arms and we began kissing harder, her tongue playing with mine while she wrapped her arms around my neck. Standing this close to me there was no way she could miss my erection, and as she moved in closer still she began to grind gently against it. I was like a kid in a toy shop. I didn't know where to put my hands first. I ran them down her back and over her bottom. Then I remembered her magnificent breasts and gently brought one hand up to feel the weight of her left boob.

We came up for air just as Chris returned. There was no embarrassment. He smiled wryly before suggesting we go upstairs. Chris went up first while Lesley led me by the hand. Their bedroom was large, taking up half the top floor. It was dominated by a large king-size bed. Chris walked over to an armchair in the corner and sat down.

Lesley now faced me with both my hands in hers. She looked utterly entrancing. As she kissed me again she raised them to the buttons of her blouse and I willingly began to undo them. It opened to reveal a white lace basque that barely contained her breasts. Having imagined them for months I couldn't resist cupping them in both hands. Lowering my mouth to her creamy white flesh I kissed around the lacy tops before searching out a nipple beneath the fabric. Finding it was easy; both were rock hard. As I gently alternated sucking on each Lesley seemed to sway and let out a low moan. After a few moments she seemed to come round and began almost clawing at my shirt. I took it off in a flash before circling my arms around her back and finding the zip of her skirt. With a gentle shrug it dropped to the floor. Lesley stepped forward to stand in front of me in her underwear. It was very feminine and clearly expensive. Beneath a white underwired basque she wore white lace panties and stockings. She still had on her high heels.

By now my erection was bulging for all to see. Lesley flicked her tongue across her lips and advanced towards me. She quickly unbuckled my trousers and pulled them down. Pushing me backwards onto the bed she kneeled before me and removed my shoes and socks before looking up at me as she eased my boxers over my bottom and down. Her hand found me before her eyes did, but as she continued to look up she lowered her mouth until it enveloped the head of my cock. I'm neither under- nor over-endowed, but in the half-light my cock seemed enormous. Every nerve ending along its shaft was tingling. I rocked my head back as Lesley's mouth encased it in a warm and wet sheath. For a while she gently stroked it up and down with her mouth, before tracing her tongue around the rim of the glans. The only sounds were a slight squelching as she bobbed up and down, and my increasingly heavy breathing.

After a moment or two I realised that I had my eyes shut, which was crazy, as I'd been longing to feast them on her since I'd had that first glimpse down her blouse. Longer, if I was honest. I leaned forward into a crouch, so that I could run my hands up her arms and lift her face. We kissed again tenderly.

"Take your top off," I said softly. She smiled knowingly, before reaching behind and unhooking her basque. It fell lightly from her breasts before she pulled it away slowly, deliberately. Once more she was looking into my eyes, as if both searching for approval and delighting at the effect her body was having on me. My already rock-hard cock lurched upwards again involuntarily. It made her smile.

She was absolutely all woman. Her breasts were large and but still firm enough to be noticeably standing to attention. Her stomach was a little rounded, but showed clear signs of muscle tone. By any measure she was still slim for her age.

I traced my fingers lightly over her breasts before cupping them both in my hands. They felt wonderfully warm and heavy. She reached up and placed her hands over mine, before leaning forward so that my cock was nestling between them. Then she began slowly moving up and down. I watched mesmerised as the head of my cock disappeared and then reappeared as she tit-wanked me. Occasionally she'd bend forward and lick the tip of my cock as it emerged.

I suddenly remembered Chris and looked over to where he was sitting. He'd pulled his trousers half down and was slowly stroking his cock. Oddly, it seemed like the most natural thing in the world. I quickly turned my attention back to Lesley.

She now had my cock clamped firmly between her breasts and was enthusiastically pumping away.

"Do you like that?" She asked breathlessly.

"Yes," I croaked, now worrying that I might cum before getting the chance to see more of her.

I lifted her bodily towards me and backwards onto the bed. We both shuffled up so that our heads were on the pillows and we were lying side-by-side. Then we began kissing again: butterfly kisses at first, but soon hungrily chewing at each other's lips. Lesley was making little moaning noises and had grabbed my cock. As we were pressed together she pumped it vigorously. I was longing to fuck her, but I also wanted to finish unwrapping my present. Breaking away, I dived down to her panties and buried my face in her crotch. I ran my hands the entire length of her leg, up from her calves, before pulling aside the gusset and burying my tongue in her pussy. She cried out involuntarily and began breathing heavily. As I continued to explore her pussy I eased her panties down and out of the way. As I did so she ran her hands through my hair and pulled me further in towards her. She was sopping wet. I jabbed my tongue into her pussy before sucking gently on her clitoris. Lesley arched her back and cried out again in pleasure.

As she continued to ruffle my hair I moved my attention away from her pussy to the creamy white skin surrounding it and along her inner thigh. Her gasps indicated that she was reaching orgasm. I wanted to be inside her when she did.

Clearly she was on the same wavelength, because as I sat up slowly she gently took me by the shoulders and rolled me onto my back, before straddling me. As she perched above me I was again able to admire her breasts and instinctively raised my hands to cup them. She seemed a little more preoccupied with my cock, and wrapped her left hand around it before easing forward and pressing the tip of it against her pussy. As she did so her breasts swung before me, just as they had done that day in the office. Except this time I was able to crane forward and take an inviting nipple into my mouth. Lesley murmured appreciatively, and for while we stayed there, her swaying gently and me exploring her glorious breasts with my mouth and hands. Then she gently sank backwards onto my cock, and I felt the warmth of her pussy as she enveloped me completely.

Initially she just sat there, slowly grinding her hips in a circular motion, but as I cupped her boobs she picked up the pace and before long was bouncing energetically up and down.

"Oh yes, ...oh yes" she kept repeating, occasionally adding - almost to herself, "Fuck me, Eddie. Fuck me harder."

As my rod plunged in and out of her pussy I let my hands go wild all over her body. Occasionally she'd grab them and hold them against her bouncing tits, but the sheer excitement of the scene meant that I couldn't help but keep them on the move, running them across her creamy flesh, up her legs, across her stomach, and finally grabbing her hips as I thrust myself deep inside her. By now I was becoming aware of that the bed springs were creaking in a way that suggested we were being a little too energetic. Not wanting to stop I grabbed her round the waist and, while still inside her, eased her over onto her back. Despite my best efforts my cock slipped out, accompanied by a flattering, "Oh" of disappointment from Lesley. The way she looked up at me stopped me briefly in my tracks. She looked so beautiful. As I sat up slightly she lay before me, her legs wide apart and her hand on my chest. I shuffled forward until the tip of my cock found her entrance, before pushing my way in, slowly at first, but rapidly building up my thrusts until I was sliding all the way in and then pulling nearly all the way out. Lesley returned to a world of her own, panting hard, and moving in rhythm with me. A noise behind me caused me to turn. It was Chris, fully naked and with his cock in his hand, walking towards the bathroom. From his expression I guessed that he'd just cum.

I turned my attention back to Lesley.

"Fuck me, fuck me hard," she continued to plead, while her breasts swayed in unison with the pounding of my hips. I knew I couldn't last much longer. With one final thrust I emptied myself into her. I seemed to cum for ages as Lesley ground her hips against mine. Finally, I dropped down beside her.

For a while we lay in silence beside one another. Eventually, Chris emerged from the en suite bathroom and I was reminded of the familiar rituals that married couples go through after they've had sex - except that in this case it was Lesley and Chris who were smiling contentedly and chatting about bedclothes and setting the thermostat. I thought the time had come for me to leave so started to get out of bed, but Lesley restrained me - interestingly, by grabbing my cock - and in a soft voice asked me to stay.

"It's a big bed," she said, simply. "Chris will sleep this side of me and you can stay the other."

If that sounded unorthodox, I figured it was no more so than the rest of the evening, and so settled back down. While Chris went round switching off all the lights in the house Lesley hopped out bed and went to the bathroom, returning in a long T-shirt. She still looked mesmerizing.

Surprisingly, I slept well - we all seemed to. It was light when I felt Lesley stir beside me. Lying on my side, facing her back, I left her shift towards me. Then I felt her naked bottom push against my groin. I reached down and ran my hands over her hips, and was rewarded with contented purr. As she continued to push against me I became bolder, and reached up under her T-shirt to cup her breasts. They felt warm and heavy, and her nipples began to harder under my touch. I couldn't quite see Chris on Lesley's other side until I saw her take his hand in hers and hold it tightly. It seemed to be a signal. Rolling forward so that my now hard dick was between her butt cheeks, I parted them gently and probed to find her opening. Her other hand reached forward to find me and guide me in. We both seemed ready for a hard fuck.

As my cock entered her pussy she let out a yelp and squeezed Chris' hand harder. I began to pound her from behind mercilessly, shunting her up the bed as I did so. She continued to hold onto Chris for support but was breathing heavily, and moving in unison with me. I knew that neither of us would last long. It was what my wife and I used to refer to as a ‘pherapeutic phuck': driven more by need and lust than a sense of intimacy. With a final thrust I came inside her and was rewarded with a cry of, "Ohh yes - yesss!" from Lesley.

In the months ahead Lesley and I hooked up more than half a dozen times, always with Chris in attendance. The images I'd conjured up of her wearing, and then removing, various office outfits were gradually replaced by real memories, as she willingly worked her way through my favourites. I also got to know Chris quite well (although our physical intimacy never extended beyond a handshake), and I grew to like him immensely. He was a fascinating man: very clever and with a dry wit that could induce laughter with a single word or a raised eyebrow. I never asked him why he liked to watch his wife - because I didn't have to. After more than ten years of marriage it was plain that this was their way of keeping the excitement alive. Lesley craved adventure, but she needed Chris there as her safety net. There was something very touching - and very grown-up - about the way in which he accepted this as a sign of her devotion.

In time, our encounters ran their natural course. Lesley introduced me to a girlfriend of hers, and our threesomes ended. That is, until my new girlfriend expressed an interest in getting together with Lesley and me. But that's another story.