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One Night With Helen

"High heels, stockings and attitude, and quite the aptitude in the bedroom for a 'virgin.'"

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I had no doubt she was using a fake name on the website's profile, after all, how many people do use their real names on adult sites? But Helen Troy seemed a bit on the nose, she didn't really look Greek in any way to me when we met. Helen was not wearing much makeup, some subtle shade of red lipstick seemed to be about it, her hair was tied back but showed plenty of curls while she wore what might very well have been office attire. A crisp white shirt crossed with pinstripes, the top three buttons undone leaving a hint of cleavage that would only really catch your eyes if you were standing next to her.

Her choice of skirt, however, must have been quite the head-turner if she actually wore that to the office. Short, a good inch above her knees showing off the shiny gleam of her stockings. Like her jacket it was grey, and form-fitting, stretching to allow her to take long strides in her three-inch heels as she entered the cafe.

The effect left me wondering what field of work she was in and how I could get a job in her office. I quickly checked myself to make sure my tongue hadn't unrolled onto the floor and made sure my legs were crossed, then I raised my hand to get her attention. I felt very much out of her league dressed as I was in just blue jeans and a white T-shirt, my jacket over the seat I'd taken.

Helen smiled as she saw me and slinked her way over to me. I remembered my manners and stood up offering my hand for a shake, which she accepted as we introduced ourselves, then pulled me towards her for a quick peck on our lips. I could feel something left behind on mine as we pulled away, I could almost taste it but my nose picked up the faint scent of mint. Some sort of lip gloss maybe? Either way, my heart seemed to perk up a bit more.

"Please, take a seat," I said as I waved a hand at the chair opposite mine. To my surprise and delight, she took the chair to my immediate right, crossing one leg over the other. I could hear the sounds of her stockings gently rubbing against one another. "Can I get you something? Coffee? Tea?"

We had a long chat as we ate our sandwiches, never once about anything dull. Somehow I think she could have made talking about the weather... interesting. Helen had an interesting manner of making sure she only ever took a small amount of the sandwich between her lips, almost nibbling the corner before slowly closing her mouth around it.

"Have you had much luck on the site?" she asked. I shook my head.

"Not really, I've not been on long, maybe two weeks."

"No one else has sent you any messages?"

"Oh, there were messages, usually the same request to go to another site to prove who you are. You know, by providing your bank details."

"Oh god," she laughed daintily. "Are they still trying that one?"

"Then there were two women who seemed genuine, but they never showed up for the dates."

"Cold feet, it happens." She gave me a curious look, like she was reading my mind. "Any others?"

"Not on this site, there was another where I got chatting to this one woman who claimed...Yes? She claimed to be a shrink of all things."

"Doing some kind of study of online dating?"

"If she was, she never said so." I paused as I recalled some of the details. "But she did introduce me to some online friends of hers on that site."

"That sounds interesting," she gave me an inquisitive look. "Where did that go?"

"Well, I got suspicious. All the people seemed to be writing their messages in the same style."

"Ohhh, I see, she was using puppet accounts then?"

"Yeah, that's about as good a name for them as any. But they all seemed to close down, and then you'd get a new profile days later, with very similar pics and the same sort of stats and interests and whatnot."

"Well, sounds like she was a bit of a cock tease," Helen said matter-of-factly. "You wanna go for a walk? The park over the road is rather nice."

"Don't you need to get back to the office? Your lunch break must be nearly over."

"I took a half day, I had a good feeling when we got in touch," she said as she uncrossed her legs before she stood up, patting down her skirt to remove imaginary crumbs. I could hear the sound of her stockings rubbing gently against each other and wondered what it would be like to have those legs wrapped around my ears.

We'd already paid for our meal so we left and enjoyed a pleasant walk in the sun-filled park, a gentle breeze took the bite out of the heat. If Helen's profile was to be believed, she was thirty-five, five years my senior, but barely looked 30. She had a confession to make that I found almost impossible.

"I'm more or less a virgin," she admitted with a coy smile which made her eyes light up.

"What?" I was flabbergasted. "How?"

"What I mean is, I've only had sex once." I picked up on something in her demeanour.

"You mean with one guy?" She nodded, still looking coy.

"See, I spent years convinced I was a lesbian, so I did lesbian things. Or rather what my girlfriends told me were lesbian things." We turned a corner in the park, I could see we had the place more or less to ourselves, there were trees and bushes that towered over most of the pathways as well as hemming in the entire park itself. But I could just about see a row of terrace housing at the far end which Helen seemed to be almost guiding me towards. "Lots of kissing, rubbing, feeling, fingering, licking, that kind of stuff."

"When did that first start?"

"When I was eighteen, I've spent most of my life loving only women, thinking that was all I needed."

"So, something obviously changed?" she nodded. "Did you come home one day to find a used dildo left out where anyone could see it?"

"Not quite like that, no," she laughed a little, then took my hand in hers and patted it. "I was involved with two other girls, who I thought were the most beautiful women ever, three ways each night. Then I went off on a work do for a week, came home a day earlier than I expected, and found them in bed with two men."

"You don't sound upset?"

"Oh, not now I'm not, but back then, dear god, I just screamed. One of them had a cock in her arse! We'd never done anything back there! I just screamed and ran out of the room and sobbed in my bedroom. What was worse, they just kept going at it."

"Christ! They didn't check on you?"

"No, not until the next day. Then it all came out, they'd been seeing more than just me, there'd been other girls, more men, groups... I'd always thought before that day that the bed needed replacing."

"God... when did all that happen?"

"About a year back, I'm over it now, but it did get me thinking. What am I missing?"
"So..." I put two and two together. "You're technically a virgin because you've never had cock?"
"Well, I was, until about a month ago," she switched from holding hands with me to wrapping our arms together and pulling me closer, those naughty eyes of hers only lit up even more as her smile took on an almost wicked bent. "That was something I needed to try, to find out if I actually liked cock, and it turned out I do."
"What did you do with the lucky guy?"

"Well, I sucked him, didn't really know what I was doing there, but he didn't complain." She paused again, then smirked. "Then there was The Main Event. It was alright, but he was more the kind to just push it in, then hump away."

"Didn't try any other positions?" I realised we seemed to be heading towards the houses at the back of the park.

"No, just held my legs down on the bed, while he mauled my nipples and humped his end away. The sex wasn't good, but I did like the penetration." I got the feeling she was holding something back.

"Was that all that happened?"

"Well, he did lick me out, but he wasn't very good at it." She took a deep breath. "And the condom came off too."

"What? Did he slip it off?"

"No, never had a chance. His hands were always busy, holding my legs open, holding me down, and playing with my boobs. Speaking of which, is titty fucking normal?"

"If you have the boobs for it, and you both like it. Did he?"

"That's how I know the rubber came off."

"He probably pulled out of your pussy with that aim."

"Maybe. Either way, I'm not seeing him again. I want a younger model," she smirked, then pointed at a house in the middle of the row. "That's mine, you want to come in for another coffee? Or something stronger?"

"I was thinking of something wilder."

"What a coincidence, so was I!"

We made our way upstairs to her bedroom, having barely paused to close her front door or take our shoes off. She was clearly an expert in undressing her lovers as he had my shirt off over my head with a strong tug at the back of my collar before she was pressing her still-clothed body against my naked chest. Our hands roamed over each other's bodies as our lips played with one another. My hands claimed a spot on each of her incredibly tight butt cheeks, I'd barely had time to spot her bicycle downstairs, but as my fingers made their way over her back towards her neck I could trace the contours of her muscles on her very slender frame.

Her hands were already tugging my belt free from my jeans as our tongues started playing tonsil tennis, she pulled me towards her bed by the top of my trousers while my hands pulled her skirt up over her hips and waist, while she somehow pulled off her jacket top in one move, flinging off to one side while I stared at the sight of what lay between her rolled up skirt and the tops of her shiny black thigh high stockings.

The barest, most silky smooth-looking pussy I had ever seen—clearly, a waxing job given the lack of any bumps or nicks, or maybe a laser had been involved. I briefly glanced up at her, she still had that trademarked evil grin of hers plastered on her face, like she knew what I was thinking with the evidence before me. Which was about to be spread before me as she rested her perk buttocks against the frame at the foot of the bed, hands out to one side, lightly touching the pair of bed knobs that made up the framework.

I planted a kiss on those inviting lips, they tasted perfectly clean, like she'd had a shower beforehand. I heard her moan in appreciation as I planted another light kiss on them, then another and another. I looked up again, her mouth was slightly hanging open, as if she was close to orgasm already. If that was true, this was the fastest I'd ever known a woman cum from any ministrations like this. She was fiddling with her shirt, trying to unbutton it with one hand while the other was propping her up, grabbing onto one of the giant bed knobs at the foot of the bed.

"Ahhh!" she muttered, as I parted her lips and found her clit was large and swollen. "Ah!" she uttered, as my tongue teased it. "Uh!" I don't think she was expecting me to slip her pussy the tongue, or the feeling of the flat of my tongue against the length of her womanhood. But she had a very different taste to any lover I'd ever had before. There was something almost addictive about her taste even before her juices started to come into play. "Ugh! Ah! Oh! Just like that! Please! Oh God! Never knew... men could... lick!"
She actually gave up trying to hold herself upright, falling over onto the bed while I managed to keep my face planted on top of her mound, my lips almost forming an airlock around her pussy as if I were trying to French kiss it. I've never met a squirter. Or at least, if I have met any and not know they were it's only because I've not fucked them.

I had a feeling as Helen came from my tongue work that she might be one, I just hadn't found quite the right spot, but when she came, you knew about it. One second my tongue tip was pressed right on her magical little nub, the next, my entire face was covered with an explosion of lovely juices, dripping over my mouth and down my own throat, while Helen wailed like a banshee in heat, legs flailing around like an Octopus on crack cocaine!

"Gimme a taste!" she screamed, pulling herself back upright and planting her hands on either side of my head in a desperate bid to pull me to her other lips. I complied and felt her lips pressed against mine as her tongue slid past them, swirling around inside my mouth in an effort to taste the mix of her love juices and my saliva.

Once she broke free, after what felt like an hour of locked-lipped action, I noticed her breathing was so heavy her breasts were almost free of her bra, her shirt had come off at some point in the activities. It was a two-tone mix, dark black on the underside covering half of each of her breasts, a dark blue covered the rest of the cup, with a small bow of the same colour covering over where the nipples were probably meant to be.

"God... Christ Jesus... Mary and Joseph," she barely got the words out, and part of me wondered if she was Catholic. A different part of me thought a crucifix would have looked so naughty swinging between her bountiful breasts. I wondered if she was into dressing up.

If this went anywhere, we could get her a nun's outfit. And more of those thigh-high stockings. "You must have had lessons from some of my exes..." Helen fought to get the words out, the faintest hint of that almost Satanic smile was forming slowly on her glowing face. "That's some of the best pussy licking I've ever had."

"I was hungry," I jested, and leaned in for a kiss. She reciprocated, then slowly pushed me upwards.

"Starving would be my best guess," she said, then traced a pattern over my chest with her fingernails. She looked a bit further down. "You never took off your trousers?"

"You never took off your skirt, but I like it where it is. Looks naughty. But," my hands grabbed hold of each bra cup and gave them a sharp tug so her breasts were mostly free. Her tiny, taught nipples popped out over the top. They looked so small they could have been hidden behind a five-pence coin, and so tautI'd bet she'd heard every joke about using them to cut glass with. "Ahh, that's better. Now, tell you what, let's see you cavort around this place like you own it."

"I do own it," she giggled, standing up on top of her bed, squeezing both her breasts and doing a slow, rhythmic dance with mostly her hips and shoulders. The light coming in from her bedroom window seemed to get caught perfectly on the shiny blackness of her thigh-high stockings, while her slick pussy juices did much the same. "Time to get your kit off, handsome, I've got a cock to suck," she purred.
No sooner had I stood up beside her, sharing in the slow, sexy dance routine, her hands were already playing with the top button of my jeans, then reached below to continue, but stopped as she looked at me in mock surprise.

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"More buttons? Too good for a zipper?" she jested.

"Much too good for a zipper," I grinned as my own hands slipped off her bra straps. "But let's leave the rest of that bra on."

"Why?"

"Because it looks so much naughtier, and there's time to get the girls out later." She smiled, then pulled down at my jeans, taking them down to my knees and most of my boxers with them too, my hard cock sprang free, almost slapping her in the chin.

"Ha! That's a first. Never been beaten up by a cock before!" She pushed a hand down between my legs to force the rest out, and I stepped out of them and let her take in the full picture of my cock swaying around like a freed beast, pointing right at her with not so noble, but fun, intent.

"Okay, okay, okay..." she sounded impressed and worried at the same time. "You're a lot longer than he was, and about as wide..."

"If it makes you feel better, you get to call the shots here."

"You mean it?"

"Sure, this is a night I want to be all about you, your enjoyment, your... education."

"What about my stockings? Should I take them off?"

"When you look that hot in stockings you never take them off. They just add to the fun."

"Okay, so..." Much to my surprise, she lay down on her back, head propped up by her pillows before she looked back at me. "This is how I did it the last time. The cock sucking that is."

This was my turn to try something new, or rather a new position. All my previous blowjobs had either been with me standing up while the girl was on her knees, or even squatting as she sucked me, or with me on my back or some variation of a 69. I stroked my cock as I tried to figure out how I was meant to let Helen suck me while she lay like this. I grabbed my trousers and pulled out my wallet to buy me some time.
"What's the matter?"

"Something for later," I said, putting a condom on her bedside cabinet. Then climbed back onto the bed, and tried to kneel down on one leg with the other lunged by her side. She happily grabbed my cock and gave the foreskin a couple of slow, gentle pumps.

"How fast can I go with this?" she asked as she speeded up.

"Not too fast, and not too far back, the foreskin only goes so far."

"Okay, so this is good?" her hand was a nice tight sensation around the shaft.

"Oh, that is excellent."

"What about this?" She kissed the tip of my purple helmet, then flicked her tongue out over the little hole, then tried to tease it as if she wanted to get her tongue tip inside it.

"Ooohoooohhhhhhoho!" The sensations were driving me wild. "That's... great... better than great."

"And this?" she pursed her lips and blew cool air over the top of my swollen helmet.

"Ahhh, yessss...."

"Or this?" She put the entire helmet inside her mouth and locked her lips around it tightly. I have no way to describe what her tongue did to it inside the privacy of her own mouth but it made my vision blur, and when it returned, somehow she had half the length of my cock buried inside her mouth. I could feel her tongue pressing upwards along my shaft while the helmet was pressed against what had to be the entrance to her throat.

"Fuuuuuuck me..." I managed to barely whisper in delight as I looked down and saw her eyes were crunched up with the effort of trying to deep throat me straight off. "You..." I wanted to tell her she was a natural at this, but I wasn't sure if that was really a compliment, no matter how much evidence she was given me that she was born to do this. "You enjoying that?" Much to my delight, she nodded her head which had the effect of bringing her teeth lightly into play, gently adding some teasing which wasn't needed, but felt delightful.

Then she started humming.

Maybe she was really a repressed bisexual, maybe that story about the lesbian lovers had been a cock and bull tale, maybe it was all true, but right now, I didn't care. All I did know was that if she kept going like that, she'd have me cuming down her throat as if it was a fireman's hose.

I hated the position I was in, the awkward kneeling meant my lunging leg was basically getting a workout, I could feel the acid build up from having held that pose for so long. Really, I needed to switch the legs over, preferably, I wanted to be in a different position, one where I could do things like play with those beautiful nipples or tease her pussy, but I also didn't want to cum just yet.

Helen had ideas of her own. I felt her hand come back into play, wrapping around the shaft just above my balls and squeezing slowly around it. She pulled her mouth free, with a very audible POP as the head broke free from the seal of her lips, absolutely drenched in her saliva. I think she made the POP sound herself, she was certainly grinning as if she'd done something rather clever that she thought I didn't know about.

"Wow! You must have stamina!" she said, licking her lips as she pumped my cock slowly. "The last guy didn't last very long."

"Wait till I get my cock inside your pussy and we build up the speed." I took the opportunity to lay down beside her and let my fingers wander over to her still-wet pussy. "I can last in the pound town for maybe an hour or so."

"Promises promises," she joked as she slowly worked my shaft some more.

"One I aim to keep," I smiled as I stroked her hair with my other hand, letting my index finger trace a line over her cheek before moving on to her chin.

"If I keep doing this, will you cum?" she asked, "I mean quickly? Or should I stop?"

"No, that's too slow," I replied as I fingered her pussy deeper, finding her g-spot and making her gasp. "Besides, I'm not close to cumming right now. Are you?"

As if in response she started to pump my cock with faster, harder strokes. In turn, I stroked her g-spot with the same temp, each of us matching the other's speed and watching each other's eyes as we worked one another into breathless, sweaty messes.

"UGH!" she tried to hide the yell as she came, biting down on her lips as her head pushed back into the pillows. She let go of little me as she thrashed about on the bed while my fingers strummed away at her love box as if they were the strings to a guitar, while her voice provided an accompaniment that almost sounded like an exorcism gone wrong. She pulled my hand away from her and fought to get her breathing back under control. I could see beads of sweat on her brow dripping all over her, as if she was in a hot spa with a locked door.

"How you feeling?" I asked once her panting had settled down somewhat. "I've never seen anyone climax like that."

"Neither had my exes," Helen admitted. "And I've never seen any other women react like me either."

"Porn stars are more conservative in their orgasms," I joked. "And they are faking most of theirs."

"I guess I must be blessed. How's your hand?"

"Soaked," I said, looking at it for the first time since I'd decided to finger her.

"Nothing unusual there then," she smirked, then rolled herself on top of me. I could feel her pussy pressing down against my cock while her hard nipples teased my skin. "Think I'm ready to take that cock of yours?"

"Well, you are eager," I said, giving her a quick kiss.

"Well, you've not come yet, seems only fair." She reached over the side cabinet and grabbed the condom. "Ribbed?"

"Believe me, they feel great for both."

"Hmmm, seems kinky," she worked it free of the package, then grabbed my cock. "I wonder, can you get ribbed dildos?"

"Probably, never looked into it, never needed to." She'd rolled it onto my length with a little fumbling but then gave the entire length a fond stroke once it was fully covered.

"It looks odd, like it's from some sci-fi horror movie, or like it's clothing for a cock," she giggled. "But I like it."

"You'll like it even better when it's inside you."

"Promise?"

"Promise. You want to go on top and slide down on me, or do we…" Wordlessly, she slid her pussy lips along the length of my hardness a few times. "You are a fast learner." She smirked again, then leaned in to kiss me softly, then rolled onto her side of the bed and beckoned me to get on top.

"Probably be easier to let you take the lead this time," she winked at me. "Besides, I'm more used to being on my back." I resisted the urge to make a That's What She Said joke, and smiled as I rose up and over her.

"Well, here's some words I want to say to you a lot, spread 'em, darling." Helen giggled, complying by spreading those beautiful stocking-clad legs for me, as I placed my own between them and lined up my very ready cock to the entrance of what I was sure was going to feel like heaven. I slipped the head in first, making sure we kept eye contact. She looked happy to continue, but I wanted to be sure. "Remember, you're calling the shots, if anything feels wrong, tell me, you want me to do something, just say."

"Hmmm, I want your cock inside me," she replied with a happy look sparking in her eyes, so I pushed in a bit more and felt a slight resistance. Another push and the resistance got a little tighter, as if there was a gloved hand wrapped around my shaft, squeezing it as if to make me slow down. She just nodded at me to continue, so I pushed in a little more, making sure to stop at each sign of resistance. "Just push it in," she mumbled. I wrapped my arms under her back and held onto her shoulders as I pushed some more into her, when an idea came to mind."How much do you think is in?"

"Hhmmm, half?"

"Sure?" She nodded. "Take a look," I eased myself up off her body, essentially doing a press-up to let her look at the connection we had.

"Christ!" she uttered. "That's got to be about an inch left to go. Go on, do it, push that all in, one last big push! no, don't pull out!" But she was captivated as she kept watching between the gap between us as my cock almost left her pussy, bar the purple head. Then without a word, I thrust up inside her, sharply, deeply.

"God!" I said after I'd pushed the last of my length inside her. "That's the tightest pussy I've ever had!" Which was certainly true. A couple of years prior, I'd had the pleasure of meeting two, eighteen-year-old uni students, on separate occasions. Neither were virgins, but both had been impressively adventurous, nimble, and tight as vices! One of them had started doing Kegels while I was inside her, which had reminded me of the first time I'd ever sodomised a lover. I wondered if Helen would be into having her chocolate factory opened up for business.

"You think so?" Helen panted as she adjusted to the sensation of having only her second-ever cock. I looked over her stocking-clad legs, laid out on either side of me

"I know so," I said as I pulled out slightly before slowly pushing back into the hilt. Helen mumbled something unintelligible. "If you wrap your legs around me, it'd be even tighter."

"Ack, maybe later on. I want to enjoy this as is!" She mumbled a few things I couldn't make out, then looked me dead in the eyes. "It's just as well you lick pussy like a lesbian! If I hadn't cum already, I don't think I could have taken all of that!"

Then Helen utterly surprised me, she rolled up both over so she was on top and began riding me as if I were a stallion! Her hips slammed off mine before she seemed to find her own sweet spot and started doing little rotations with her hips while bouncing herself off me as if she was a piston in a powerful locomotive. I'm no stranger to being ridden, the sensation is always incredible, and getting to watch the expression on a woman's face while her breasts swing to and fro has always been a secret kink of mine.

Best yet, whether she was conscious of it or not, her stockings-clad legs were gripping against mine as she rode, either as support or to dominate me, I neither knew nor cared, I just enjoyed it. But there was something odd with the sensation as she picked up her speed and I felt the impossibly tight folds of her pussy clench ever harder around my shaft.

"Oh shit! Stop!" I told her as she bounced ever harder off me. "The condoms came off!" To my surprise, she just gave me a look I couldn't read, leaned in and kissed me, before breaking it off and lifting one of her legs off me as my cock fell out to one side and slapped off my hip. She slipped her fingers inside and played around inside as she looked for the condom, then threw it away, grabbed my cock again, slid it back inside her and went right back to riding me as if nothing had happened.

"Remember, I'm not on the pill," she said with a seductive look that made me think I was fucking with the devil. Somehow my cock seemed even harder than ever.
"So, where do you want me to cum?" She smirked. "In your mouth?" The smirk only got bigger. "Over your tits?" A bigger smirk. "Over your face?" The smirk was in danger of taking her head off. "Where?"

"In me!" came the reply as she upped her speed even more. That might have been just what the doctor ordered to send me over the edge and get my sperm shooting out of my cock like paratroopers on their way to secure an enemy encampment. Sure enough, the insides of her amazing pussy were soon plastered with my baby batter while Helen, oblivious to my own screams of pleasure as I shoot my load deep inside her, went back to wailing like a banshee as her pussy juices joined the show, flooding over my crotch like a dam had been broken.

I was vaguely aware of an angry thumping noise from what must have been the neighbour's side of the wall, but neither of us cared one bit. We just kept going till we were fucked out of our minds, drenched in our own sweat, each other's cum and our lungs feeling like we were a pair of deep-sea divers that had just come up for air.

"God," Helen managed to mutter after a while. "That was a hell of a lot better than the last guy... Very different to what I got up to with the girls." She turned and gave me another one of those inviting smirks of hers. "I wonder what else I can learn from you?"

"Tell me, have you ever tried fisting?"

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Written by TheTwistedMan
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