The Winsome Widow

When he parked the car beneath our building, I left my dress around my waist and kept hold of his erection while we caught the lift up; I briefly wondered if anyone was monitoring the security camera. We got into the apartment without being seen, which was almost disappointing, and then went on with the role-play; I pretended reluctance again and he tried to bring me around, stroking my nipples, raising the price and edging me slowly into the bedroom.

Ultimately, the sex was once again amazing. He fucked my mouth, my breasts, my pussy and even between my closed thighs, deliciously grazing my clitoris and making me come for the third time. He also came twice, once in my mouth and once in my pussy; but like last time he didn't get soft in between. In fact, he just seemed to get bigger and harder and when he finally entered my pussy, I had that first-time feeling of being opened up like a ripe virgin again, my pussy clinging and gripping at his thick manhood as he plunged all the way into my steaming core.

Evan's club night became a little tradition with us; one night I texted him an address and let him seduce me at a bar; on another I had my car 'break down' so he could help me; I even pretended to be a slutty cop one night, stopping him, strip searching him and then making him perform a ridiculous and sexy sobriety test on the side of the road. Every time we fucked like wild animals, and every time I came at least twice; five times on one occasion.

After the first couple of adventures, I thought that my recollections of the size and hardness of his cock were being influenced by the intensity of the sex; but more and more I came to believe that on club night he really was thicker, longer and harder than normal. My pussy agreed with me too; although I fully expected to have tender lips from his pounding cock, I also felt sore and stretched on the inside, and probing around with a dildo the morning after, there were indeed a few tender patches in there that suggested a bigger-than-usual cock.

After that first month, we didn't try again to recapture the magic mid-month; we just had regular, satisfying, loving sex and saved the raw, animal sex for that last Thursday night.

One club night I had to work late and I had already warned Evan that I had nothing planned; in fact he would probably beat me home. As it turned out I did get home first, but I was so tired that I just undressed and crawled into bed. Evan came home after I fell asleep and crawled in behind me, snuggling up close with one hand cupping my breast while his hard cock pressed uncomfortably against my bottom. I was so tired that I was initially prepared to warn him off, but then surprised myself when I started to get horny and wet.

I opened my thighs a little and Evan slipped his cock between them, fucking that little triangular gap where my pussy meets my legs, while I crossed my ankles and squeezed him tight between my thighs until he came. Did I think that would be the end of it? Oh, so wrong! He was still hard and he just flipped me over, ripped off my panties and plunged his cum-dripping cock into my soaking cunt, pounding me with a dozen quick strokes until he had me screaming and writhing, grinding his knob against my cervix while star-bursts of ecstasy exploded in my womanhood.

Evan went on fucking me to two more climaxes, the third one exploding while I was still coming down from the second; and then he came again, pumping jet after jet of thick cum into me while he stirred it with his cock, working his hot seed into every corner of my molten pussy.

That was the night that sparked my interest in Evan's club. Prior to that, I was prepared to believe that our wonderful lovemaking was a fortuitous product of my creative role-playing and an evening of lascivious guy-talk over a few lubricating drinks. But this time the role-playing was removed from the equation and the sex was still every bit as good – or better if you consider that I didn't even want sex that night – I had to question exactly what went on at that club to get my boyfriend into a pussy-pounding, animal-fucking, twice-cumming kind of mood.

I tried asking Evan, of course, but he said it was very secretive; like Fight Club, the first rule of The Winsome Widow is that there is no Winsome Widow. Of course, he didn't say that; I didn't even know the name of the club until I hired a private investigator. But that was later; after I had run out of options.

Our routine went back to normal, or so Evan thought; every month he would go to his club and when he returned we would fuck like walruses in heat. Even in my suspicion I couldn't deny the raw sexuality; it wasn't like I was just playing along, he really did make me indescribably horny when he came home and he really did bring me to two, three and even four consecutive orgasms; always having two of his own and never softening in between ejaculations.

Wondering whether they had hookers at the club, I checked for the obvious signs like lipstick and perfume and cum stains in his underwear, but never found anything amiss. Taking my investigation to the next level, I waited outside his work and followed him one night, learning The Widow's location, though not her name. Parked down the street, I watched men come as the light bled out of the day; usually alone although some in pairs; and at the end of the night about eight of them – including Evan – came out as a group and with quiet nods of farewell they made their way to their own cars or walked up towards Macleay St and Kings Cross.

I pulled out quietly and drove away to keep ahead of Evan but stopped near home and got out, dressed in a sheer body stocking and waited for his car so that we could engage in a streetwalker fantasy, something we had tried before. He would ask for all kinds of outrageous sex acts and I would quote equally outrageous prices or quiz him over details, like would he bite my nipples, or did he expect me to swallow his cock, or could I use his cum to rub into my tits as a skin conditioner.

And even though I was suspicious of what he was doing at the club, even though I had just spent a few hours sitting in my car secretly monitoring his activities; still from the moment I leaned in his window, I was soaking wet and breathlessly desperate to have his cock inside me. I recognised how bizarre this was but I couldn't help myself; I had tried brushing him off on club night and ended up fucking even more frantically to four powerful climaxes. I considered the possibility that the club was dispensing pheromones or a powerful aphrodisiac, such was my bafflement at the bizarre horniness that club-night brought out in us both.

Once a month I got the best sex of my life; hell, I'm betting I got the best sex of almost any woman's life; and between times I had a faithful, attentive and sensitive lover. The right thing to do would have been to thank my lucky stars; that would have been the right thing ... but it wasn't my thing.

The curiosity consumed me. I had tried asking Evan a hundred different ways what happened at the club, what they drank, what they talked about; hell, he wouldn't even tell me the damned thing's name or the names of any of his friends there.

On the last night we were together, I played my final card and tried to withhold sex, pleading with him to tell me, but he just picked me up and carried me to the bedroom, tearing my clothes off my body as I kicked and fought. Naked and pinned to the bed, I had our safe word on the tip of my tongue but I couldn't utter it; the awful truth was at that I longed for him to take me like this. When he pressed his knob against my entrance I was barely surprised to feel him sliding around in my freely flowing juices; and even though I was crying and still weakly fighting him, he still entered me in single stroke and both of us came with intensity of the moment.

The following morning, with my perspective restored, I delivered the ultimatum that I have regretted ever since: tell me about the club or I leave.

I left.

The months that followed were a misery for me; I loved Evan – and I was sure he loved me – but I couldn't reconcile that against the secrecy of his God-damned club. There was something going on at that terrace in Potts Point – something sexual, I was sure – and I felt that Evan had in some way been cheating on me, all the while giving me the best sex I would ever experience. I felt jilted and wronged and completely justified in my actions; but I also felt petty and small and ashamed of myself. Secret men's business; what's the big fucking deal?

If it was just about what I thought of as cheating, then dumping him should have been the end of it; but of course it wasn't. Hell, under the right conditions I probably would have considered swinging to spice up our sex life, so I couldn't afford to get too holy on the idea of cheating; not that I had any evidence anyway.

The problem was a simple one: curiosity. It wasn't so much that I didn't know his secret; it was that I wasn't allowed to know his secret, and that just wasn't acceptable.

After months of self-recriminations and soul searching, I resolved to continue my pursuit of the mysterious men's club by engaging a private investigator. I told him everything I knew about the club; its location and the night that it operated being the sum total of my knowledge, and one week and $2000 later he presented to me the following information, some of which I outlined earlier: it is called The Winsome Widow; it is not a registered business, nor does it appear to collect dues from members; bank searches of Evan and other members reveal no payments to a common and suspicious vendor; and the building is owned by something called The Adley Family Trust, although it is not the listed residence of any person.

He took photographs of several members and managed to trace the names of most of them; he surreptitiously interviewed their spouses and friends but came up dry; no new information. And that was it! I thought it was going to be a complete waste of $2000 until he went through the photographs with me; they were all unfamiliar – even with the names supplied – until the second last one: Riley Campbell, a senior partner at my very own firm.

Jackpot!

I wasn't immediately sure how this helped; I already knew the identity of one member – Evan – and that was no help to me. What I needed with Riley was some leverage; something I couldn't get from Evan ... a sex scandal with a junior associate perhaps. Most men wouldn't care, but a powerful man? A married man? Such a man might be prepared to part with one secret to keep another one.

My chance came barely a month later when the partners funded a celebration for landing a big new client at work. I had arranged several opportunities to bump into Riley in the office, smiling and flirting with him, making sure he knew my name and knew I was single. It wasn't actually that difficult; I found him attractive for an older man, and he was smart and witty and a good conversationalist. On one of our 'chance encounters' in the kitchen, I actually found myself giggling behind my hand and flashing my eyes at him, not because I was trying to seduce him, but because I was genuinely flattered and entertained by his attention.

On the night of the celebration, the partners had booked out the function area of a local venue that served nice beer and wine in quantities that spoke of their intentions to entice their clients in their range of cigars and premium scotches. I was one of the first to arrive and approached the barman on my own.

"A bottle of vodka, please," I requested.

"Sorry Ma'am," he smiled, "I can only serve drinks in glasses."

"I don't want you to serve it to me," I parried, flashing my eyes at him flirtatiously and placing a $100 note on the bar. "I want you to pour it down the sink, fill it up with water and then make me Bloody Marys with it."

A quick study, he understood immediately that I wanted to appear to drink all night without getting drunk. "I could save you some money by filling an empty bottle with water," he grinned.

"What's your name?" I leaned forward, smiling and giving him a superior view down my dress.

"Dan," he responded simply.

"Dan," I said. "I'm Alex. Come closer; I want to give my new best friend a kiss."

Dan leaned over the bar and I gave him a chaste kiss on the corner of his mouth.

"Now, Dan," I said in conspiratorial tones. "I would like a Bloody Mary, made with your finest vodka, please."

"Bloody Mary, coming right up, Alex," he replied in his efficient bar-tenderly voice.

I watched as he retrieved an almost empty bottle of vodka, tipped it out and filled it with water, and then made my Bloody Mary with it.

"My friends will be ordering me the same drink," I said, "and ..."

"And you'd like me to make it with your personal vodka?" he asked.

"Dan," I smiled, "you are man of astute vision." I pushed the money towards him.

"You can hold onto that for the price of another kiss," he said, perhaps not feeling he had earned the money, having poured out only about five dollars worth of vodka.

Knowing a good deal when I see one, I leaned forwards again and gave him a softer, longer kiss; full on the lips with a little "Mmmm" at the end. Dan looked pretty pleased with it and I wasn't complaining either. I took my Virgin Mary and staked out a nearby cluster of armchairs and sofas around a low table from which I could watch for Riley.

It was easier than I expected; Riley arrived with one of the other partners and saw me sitting alone; I waved and smiled and they both came to sit with me, bringing me another not-so-Bloody Mary. They were possibly just being polite by not leaving a colleague to sit on her own, but I don't think the combination of the low chair, my short skirt and crossed legs revealing the embroidered tops of my stockings did any harm.

The place soon filled up with people and noise and between my skirt and Riley's charisma, we had a regular progression of visitors to our table, obviating the need for him to mingle in a more partnery fashion. I took many opportunities to cross and recross my legs, providing little glimpses of my red lace panties to keen observers, while also tugging at my hem in mock outrage at its inexcusable affront to my modesty as it continually rode up over the tops of my stockings.

As the evening wore on, I consumed six or more of my special Bloody Marys; adjusting my perceived level of drunkenness with each one. In one inspired move, I leaned over the table to pick up my glass – providing a long, sexy look down my cleavage – and then juggled the glass as I sat back, slopped a little over the edge and cried out as I spread my legs to avoid staining my stockings; holding them open for a few moments with my bare thighs and tiny panties on show while I laughed at myself and licked tomato juice off my fingers. Between the red lace knickers and my red lips licking the red tomato juice from my red-tipped fingers ... well if there was any guy there NOT thinking about sinking their purple prick into my pink pussy, then they're either blind or gay.

Finally at around 11pm, I caught Riley looking at his watch and then he drained his glass in what appeared to be obvious moves preparatory to leaving. Now was the time to make my play. I looked at my own watch and said "Oh goodness, is that the time?" and fished my car keys out of my bag.

"Early start for me tomorrow," I said, standing up. As I edged past Riley, I pretended to overbalance towards the table and then, overcorrecting, I tipped backwards, waving my arms and then fell directly into his lap to the raucous amusement of everyone at the table.

"Oh, my hero," I laughed, leaning sideways and kissing him on the cheek; making sure he had an excellent view down my top. "I think I'm falling for you, Riley."

Everyone dutifully giggled at my wit as I struggled out of his lap, allowing my car keys to jingle so that there could be no mistake that I intended to drive in my drunken state.

"You're not driving home, are you Alex?" Riley asked with a frown.

"I'm fine," I dismissed him with felt like a carefree, inebriated wave. "You can't get drunk on Bloody Marys," I smiled lopsidedly with sage wisdom. "The Worcestershire Sauce neutralises the alcohol." I winked at him.

"Well, I don't think the science on that one is quite final," Riley smiled. "I was just about to leave anyway; I'll give you a ride."

Bingo! "Don't be ridiculous!" I said with an over-expressive wave, which had me wobbling on my heels again. "I'm fine."

"It wasn't an offer, Alex," he said. "As of now it's a condition of your employment."

"Oh, well," I smiled. "Since you put it that way..." I held out a hand for him and although he took it politely, he didn't use it to help himself up; probably figuring I would finish up in his lap again. That was wise on his part; I felt a little electric pulse of excitement at his touch and dropping back into his lap felt like a distinct possibility.

"Bye, everyone," I waved with my free hand. I wondered if I was overdoing it; I didn't actually want everyone to think I was fucking Riley, I just wanted him to realise that they would believe my story when I blackmailed him into telling me The Winsome Widow's secrets.

When we got to Riley's car – something sleek and dark and German – he held the door open for me and I felt a little pang of guilt. He was a wonderful man; I could tell by the way he made me feel that fucking him would actually be my pleasure, but then I would have to use that against him. I didn't feel very proud of my actions at that moment, but I was still driven by my insatiable curiosity and couldn't help myself.

I was prepared to go through with my blackmail even if we didn't fuck by threatening to lie about it; but I kept up the seduction by chatting and laughing as he drove because I wanted the extra insurance and – I was realising more and more – I also wanted his cock. Why do these Winsome Widow men get me so wet?

When we got to my apartment, Riley stopped but didn't shut off the engine; it looked like he was going to be a gentleman after all. This was going to take some more creativity. I had considered this possibility and planned a few contingencies; a kiss goodbye in the car that gets out of control; or "I'm afraid, walk me to my door"; but the drunken damsel was working for me and I thought I could milk it a bit longer.

As I got out of the car, I leaned back down to flash some cleavage and say goodbye, and then stepped back and tripped on the curb, falling to the concrete on my bottom with a yelp. Instantly the engine was switched off and Riley was running around the front of the car to help me up. I gave him another flash of panties and stockings as he helped me up and then fell into his chest, running my fingertips beneath the lapels of his jacket and checking out his muscles. He was in really great shape for his age and I could feel my nipples tingling with excitement.

"I don't think that barman was using enough Worcestershire," I said, looking up at him through my eyelashes.

"Are you okay to get inside on your own?" he asked with genuine concern.

"Um?" I started to release him and looked down at my wobbling heels. "Maybe. I don't know," I looked back up sheepishly.

"Come on, then," he took my arm and beeped his car locked.

We got into the lift lobby without too much tripping. "What floor am I on?" I asked drunkenly.

He raised a speculative eyebrow at me, waiting to see if I would work out what was wrong with that question.