Sexual orientation :
The first time with Helen
The first time with Helen
This story, to my shame, is absolutely true. To save embarrassment to Helen, I have changed her name and some of the smaller details that might give a clue to her real identity. I don’t know who will read this and would hate for it to get back to her and cause any difficulties.
I met Helen on line. Her handle was “Lady of Kent”. The chat line was a free forum, I can’t remember which one it was now and it doesn’t really matter. Just that it was the vehicle that brought us together. We chatted over several months, slowly discovering little snippets about each other, developing an on-line friendship and enjoying each other’s point of view.
However, in the nature of these chat-lines, we got onto things sexual. It was light hearted banter or flights of fancy only.
Helen’s sexual experience was limited to say the least. She had married her first lover and apart from a one off with someone she had fallen for several years before, had never stepped out of her marriage. The one off was something she regretted deeply and realised that he had groomed her for his own gratification. It was only the one time.
Sex for her, was the once weekly missionary position, no variety, no excitement and very likely, nothing more than something functional. Her marriage had lasted for eighteen years and, apart from the initial setting up home and having children, had become stale and boring. I guess Helen was at the point in her life when she looked critically at herself and realised that time had passed her by and if she didn’t do something quickly, she would be too old to find that spark of excitement she read about in magazines. I suppose she might have also thought that her girls, three of them, were holding her back from her desire. Helen wanted to learn, go to college and become self employed as an accountant. A dilemma to any woman, the pull of self development and opposite draw of motherhood, something Helen felt acutely.
I, on the other hand, could be considered something of a slut. My dick pointed the way and I invariably followed. I rarely, if ever, refused the opportunity to fuck an available woman. My thirty year marriage had survived by some miracle, mostly because I had managed to keep the two sides of my persona separate and also, I loved my wife. Loving her though wasn’t enough for me. I liked the thrill of the hunt. I liked the conquering and submission of will. I had had many lovers over the thirty years, but always came home to a wife who loved me totally, with a blind faith that I really didn’t deserve. Sex between my wife and I was anything but boring. Jen had discovered her liking for bondage, light sadism and masochistic sex. It made for interesting nights and repeated washing of bedding.
Lucky man you might think. I would have to agree, but I had a greed and hunger and as I said, loved the thrill of the hunt, chase and submission. Helen was, initially, the next subject of my attention. Chatting with her on-line was part of that hunt where, by stealth I gradually broke down her defences until we met one fateful day.
Neither of us could be called perfect specimens of the human race or particularly beautiful, but, in that short meeting on a sunny day at a Kentish zoo, physical attraction had been added to the on-line fancy we had developed. We didn’t make love on that first meeting, but subsequent chats on-line took on a whole new direction. Gradually, Helen was persuaded that she really wanted to fuck my brains out and vice versa. I could be a calculating bastard, but that is just one of the weapons in the arsenal of a serial sex predator. Helen really had become enmeshed in a web of my making, my trap if you like. All that was needed now was the opportunity to spring it, then, once sprung, have my way and notch her as another conquest. (I will offer no defence to any accusation that I was a complete shit).
Helen provided the perfect opportunity. She was to travel to London with the company she worked for and be the representative on their stand at a wine exhibition in Olympia. Although she only lived approximately two hours travel away, she decided to stay in town. Now, I am sure that in the back of her mind, the chance to spend a night or two, away from home and in the arms of a lover, had more than a little to do with her planning.
I visited her while she was on the stand selling the wines her boss had brought up from Kent. Of course, she had dressed for the occasion and looked fabulous. Wickedly, I goosed her and was pleased to see her blush scarlet while offering tasters to prospective customers. How she kept a straight face and level voice as she spoke to them with my hand up her skirt from behind beats me, but she did.
Helen had to be careful. Her boss was around and he knew her husband very well. I suppose the danger of discovery added to the thrill. She had been booked into a bed and breakfast locally to Olympia for the two nights she was to be away. I had other ideas though and had booked a suit in Selsdon Park Hotel just outside of Croydon. The cost I though, was worth it and would of course, impress her. Looking back, that might have been a mistake. It led to all kinds of troubles and recrimination, eventually to disastrous consequences to her marriage.
The show finished for the day. Helen went to the B&B with her boss, which complicated things a little and meant some frantic text messages asking me to wait and then having to change plans so that we arranged to meet at Victoria Station.
Feigning tiredness, Helen retired early, leaving her boss at the bar to go to her room. Carefully, she left the cheap hotel and made her way to Victoria Station and me.
We picked up my car and drove out to Croydon. Selsdon Park is a five star hotel. An old building covered in ivy. It sat in extensive formal gardens with a terraced lawn and has a championship golf course all around it. A night there is a small fortune in a suite but as I said, worth the expense.
Neither of us wanted to eat when we arrived and checked in. The food looked sumptuous, but our appetites were squashed by a mixture of excitement and nerves. The suite was all it could be, on-suite shower and bathroom, huge bed and a well-stocked mini-bar. The décor was a little dark for my tastes, but the carpet was so lush, it felt like you sunk into it.
Helen looked at me, silent and looking scared, like a rabbit in the head lamps of an on-rushing car. I asked if she was okay and if she wanted to back out of what we had planned. Somehow, she answered in the negative, despite the croak of a dry throat. I went for a shower, leaving her to prepare herself, make whatever calls she needed to and try to calm down a bit.
She was under the bed covers when I came back into the room. They had been pulled up to her chin, her clothes dumped over the armchair in an untidy heap, suggesting that she had hurried so that I didn’t watch her get undressed. I could understand that, could understand her nervousness and trepidation. It was after all, her first real elicit experience, her first time of a planned sexual encounter outside of her marriage and also, the realisation of a shared fantasy between us, evolved from so many on-line conversations. I thought it best to just take things easily. It was just as well I had put on the bathrobe hung in the shower room because I think she might have bolted if I were naked, such was her nervous condition.
We shared a scotch and soda, with me sitting on the edge of the bed while she trembled under the covers. I stroked her cheek and smoothed her hair, trying to get her to settle. Gradually, the trembling subsided as the scotch and gentle stroking soothed her.
Inch by inch, the bed covers slipped from her as she sat and sipped her scotch. We spoke about anything that came to mind in a random order of inconsequence, delaying the moment that would be the first step to an adulterous coupling and something beyond where she thought she would ever go.
Gradually, I stoked her neck and shoulder, working my way down until I could release the sheet from where she had it trapped under her arm pits. I wanted to see her breasts. I wanted to fondle them and get to know her body more intimately.
She put up a token resistance to my hand tugging the sheet. It was not a serious attempt to keep covered. The sheet slipped down to around her waist and revealed her tits. They were small with inverted nipples and looked out of proportion with the rest of her. Helen was quite tall, had quite wide hips, but her tits were very small for her body size. I cupped one, which fitted in the palm of my hand quite comfortably.
“They are too small.” She said and looked apologetically at me. “I don’t wear a bra most of the time.” I could see that she was embarrassed by their relative size.
“They are perfect. Any bigger would be a waste.” It was an old line and not very original, but I hoped it would make her feel better. “Helen, you should never feel embarrassed about your body. It is an amazing thing and can do so much more than you know.” Her inverted nipple had now become pronounced as it grew hard under my fingers. “You see how it responds? It truly is a remarkable thing.”
I took her glass from her trembling fingers and placed it, with mine on the bedside cabinet.
Having brought one nipple to the surface, I thought to do the same with the other and then with both at the same time, using both hands.
“That’s nice.” She said, visibly getting into the feel of her tits being treated to a first class massage. Both nipples were now standing proud, not very big, but the complete opposite of inverted.
I pushed her back gently until the pillows were supporting her in a supine position. It allowed her to watch as her teats became even harder. Little buds sticking up from small areoles of a darker skin tone than the whiteness of her body.
“I love your freckles.” I told her as the dark spots became apparent. They covered her shoulders and chest and I truly enjoyed seeing them. I slowly bent at the waist to kiss the nipple nearest to me, drawing the small nub between my lips and teeth. Helen thrust her chest forward, offering herself to me, to my mouth and the warmth of my tongue. Lightly, I gripped with teeth and flicked the tip of my tongue over the infused tip of her teat. My reward was to feel it harden even more and a moan of pleasure escape from her mouth.
I realised that I hadn’t kissed her yet. In my haste, I had just gone for the tits and had forgotten to start at the beginning. It was a bit late now, but I thought important to do. After all, I intended to fuck this woman, but for it to be the way I wanted it to be, needed to get the fundamentals right so that it was the best for both of us.
I wriggled onto the bed proper to lie alongside her. My bathrobe had hit the floor leaving me in boxers. My left arm scooted under her head and I drew her into a passionate kiss. Our breath and tongues mingled while I caressed her breast. It seemed I had done the right thing. Almost immediately, Helen’s breath became ragged, her body arched and her legs opened wide, ready for my entry. I was in no hurry though, we had all night and I desperately wanted her to get the fuck of her life. I wanted her to experience an orgasm, something she had admitted to never having had before or thought she hadn’t. It was my goal to provide her with her first and hopefully, the best she would ever have.
The kiss grew frantic as her need rose. I let go of her breast and touched her quim, pleasantly surprised that she had not shaved her hair off. I love a naked quim, but sometimes, eau-naturale is just as good. I hit upon her clit and gave it the slightest of strokes with a fingertip. Helen gasped into my mouth and drew her knees up, making access to her sex easier. She was soaking already. Her lubrication had seeped into her hair. I had never known a woman get so wet so quickly.
My forefinger slipped into her easily. I imagined what it would look like, buried deep inside her while her hair closed around my knuckle. She gasped again and then made throaty noises as I finger fucked her. I slide a second finger inside. It is a much stronger ministration where support is given to the hooking massage of my fingers to her G spot and makes for a more powerful, less strenuous action, giving greater pleasure.
Without too much thought, I added my little finger and then all four fingers were inside her. Helen was bucking her hips, driving my hand deeper inside. We had stopped kissing, concentrating on just the contact of my hand. I had not met too many women who could accommodate a whole hand, but it seemed that the more I crammed inside her, the more she liked it. I briefly thought about fisting her, but decided to get my thumb pad on her clit instead. I believe she could have taken my whole hand without too much trouble. This was something new for me.
Helen’s was thrashing about now, her legs straightening and then bending rapidly. Her breathing came in gasps and her back arched. Her climax was very close and I found that it pleased me to have her in such a state so soon.
“Stop!” she shouted. “Stop!” This was something else that was new for me. None of my previous lovers had ever cried for me to stop. I hoped I hadn’t hurt her. “I need to rest for a moment.” She said, again apologetically.
“Are you okay?” I asked, concerned that I had done something she didn’t like.
“I’m fine, it’s just… well it was all too much for me. I have never felt quite so… I don’t know.” I thought that her reticence in saying the words that described her getting close to orgasm was perhaps a hangover from her upbringing where sex and all the parts that go with it are a dirty word and something to be ashamed of.
And then, I knew, Helen was afraid of experiencing a full on climax, as if it were some hidden line in the sand that she dared not cross. Perhaps she thought it would be the ultimate betrayal of her marriage, as if being in bed with me wasn’t. Perhaps it was the fear of a grown woman, going to some place she had never been to before.
“Helen, it is okay. You are allowed to enjoy yourself. I want you to cum.”
“It just… well no one has ever got me so close. I didn’t… I don’t… I have never got there before and it felt like everything was going crazy. It scared me a bit.
There it was, this woman who was a year or two short of being forty, was frightened of the power of her body. Had never experienced the beauty of a full blown orgasm and likely thought she never would. Faced with the prospect, in a liaison with someone other than her husband, the enormity had hit her and put her in unfamiliar territory. I suppose it would be daunting, but with no reference point, I didn’t know what to say.
Still with her head on my arm, I lay back beside her and began to just stroke her, hoping that, if I started again, she would fall into the natural scheme of things.
“That was powerful.” She murmured. I’ve never had that happen before.”
“But did you like the feeling?” My hand was cupping her breast with my thumb rubbing over her erect nipple, squeezing it gently, between pad and the side of my finger. “Helen, I can take you further if you want. It would be my pleasure, but only if you can give in to the joy of it.”
“It’s just… Oh, I don’t know. Let’s take it slowly eh? See what happens from there.”
I could have taken that as a finale, an, I don’t want to go there again, but I had my own agenda and filling her belly, with my spend, was top of that list.
I started back at the beginning, kneading her tit and kissing her mouth, exploring with my tongue. Gradually, in small steps, I was working her back to readiness. inexorably ramping up her desire, notch by notch. In careful increments, I had her creaming again around two fingers that entered her, but took things a lot more slowly. I thought perhaps that getting her to the brink last time, had all been too quick for her. After all was said and done, we had only been here for a short while. I was hoping that, by doing things a little more slowly, she would have time to savour the delicious feelings her body could provide.
Helen was bucking her hips again. At first, she followed the rhythm I set as my fingers massaged her G spot, but then, as the sensations built, she took over the pace, thrusting her hips up in ever increasing tempo and urgency. Four fingers were spreading her sex and her clit was being mercilessly rubbed by my thumb. I could feel her closeness, could feel her inner walls clamping and then, her legs straightened out and her arse lifted off the bed. Helen crammed her fist into her mouth to stop from screaming as her first climax smashed through her. It lasted for several seconds while her legs trembled and her body shook uncontrollably.
I rolled her towards me so that she was lying on her side, facing me while she came down from the pinnacle she had just climbed. It allowed me to stroke her lower back in soothing circles of fingertip contact.
“Alan has never done that to me.” She admitted. “I have never felt anything like that before. It was fantastic. Thank you. It was beyond fantastic. Oh wow.”
I have never been a selfish lover; deriving as much pleasure from taking my partner to the highest heights I can possible reach as having my own orgasm.
“Alan doesn’t know what he has missed then.” I suddenly knew that he had missed out on one of the most accommodating and wonderful sex partners I had ever had the privilege to have met. Helen’s capacity for sex was without bounds. If only he had taken the trouble to find out.
I realised she was crying, tears trickled over her little nose and I knew that she had realised the same as me, her husband couldn’t care less. All he wanted was a quick fuck on a Saturday night with no regard for her wants and needs. It made me sad to think that she had had to wait for so long to experience the overwhelming crescendo of an all-consuming orgasm. But, at the same time, I was pleased that it had been me that had taken her there.
Eventually, Helen calmed and we began to kiss again, her heat radiated out from her as she began to become aroused. I fondled her tits which now had hardened nipples, puckering the skin of her areoles in little peeks of need. I suckled on them and teased with my tongue. She clung to me, forcing my mouth harder against her breast.
I lightly ran a finger across her stomach which produced a tremor from her. I was finding areas of her body that responded to touch and stimulus. I loved the exploration and delighted at each new place. The inside of her elbow had her gasping as I gently nibbled and pinched her skin with my teeth. That and cupping her sex, rather than entering her, soon had Helen writhing, her hips gyrating in pelvic thrusts as she rubbed her sex against my hand. She was soaked again. Her secretions coated my hand and her hair and I marvelled at her ability to be so ready for me.
Without breaking contact, I rolled her onto her back and threw my leg over hers until I was between her thighs. I waited for a short while, staring into her eyes that looked back at me, wanting and pleading. Slowly, I entered her body, pushing my cock into her, inch by inch. It was divine and her heat enveloped me in a warm cocoon. Starting really slowly, I pushed into her willing sex, keeping eye contact, my hands kneading her tits. Helens knees came up as my full length slipped inside and then withdrew, only to be pushed back again until I bottomed out.
Gradually, the pace increased. As much as I wanted to come, I intended this to last as long as possible and for her to get the maximum out of it. She deserved the very best of me and I intended to give her that. I was acutely aware that she had been extremely brave to be here in the first place. Had entered into something she had no fore knowledge of and was in a world of the very different. That bravery deserved to be recognised and rewarded.
I settled into a comfortable pace. One that meant I would last for a reasonable while and would allow me to concentrate on her body in the quest to find all of her erogenous zones one by one. I found that her tits were possibly the most responsive, but so was her stomach when a finger lightly grazed over the taught skin. It was a delight, discovering her elbows liked attention and that her neck, just below her ear would make her thrust up to meet me.
I decided to try a new position. Eventually, with some awkwardness and a bit of giggling, she got the idea and straddled my prone body. I had to guide myself inside her until she got the hang of gyrating her hips and grinding her sex into mine. She knelt up, supporting herself with her hands on my chest. Running my fingers lightly down her back made her shudder as she set the pace. Her eyes were closed as she revelled in the sensations our bodies were giving her. She took the time to experience each new delight while keeping up the steady tempo of our coupling.
With some difficulty, I managed to slip a finger between our bodies to rub on her clit. The added pressure tipped her over the edge. Helen came again. She stuffed a fist into her mouth to stifle her scream. She probably would have stopped there and been quite satisfied, but I had other ideas and maintained the thrusting, keeping her on a high until she came again, soaking my cock with her cum.
I wriggled out from under her parted thighs and laid her down, facing away from me, her arse in my lap and her knees bent. I entered her once more and began to fuck her deeply while cradling her head in the crook of one arm and stroking her tits with the other. Helen began to thrust back at me, meeting my forward presses, driving me deep inside her. The pace quickened as my need to cum increased. I gripped her hip to gain purchase and began to ram into her, much harder than before. She managed to keep pace with me, forcing my entry to her inner depths, squashing my balls between us, but I didn’t care. The build-up to release was deliciously close. My cock was completely rigid as it plunged inside her like a stiff shaft of over enthused nerve endings. Suddenly, the moment arrived. I sunk as deeply as I could, grasping her hip in a tight grip and shot my seed into her, my body stiffened with the effort of ejaculation and Helen, realising that my moment was here, shoved back on me to make sure she received every last morsel.
She turned over after a few minutes and clasped me to her, her head with its tousled hair rested on my chest.
“I had no idea sex could be like that.” She said in something like a whisper.
We slept until the alarm clock buzzed in the morning. Neither one of us felt like food after we had showered. Helen had to get back to the B&B before she was missed, so an early start was needed.
We may as well not have bothered rushing, it turned out. Alan, her husband had been calling the B&B all night, wondering where his wife was. Her boss was frantic with worry and probably a little guilt that he hadn’t looked after her as well as he might. Helen had to face the music, worse, she had to do it on her own and I felt guilty for that.
It was the beginning of the end of her marriage. Alan said he couldn’t trust her anymore, even though he didn’t find out about us until very much later. She and her boss fell out eventually and things became so bad for Helen that she contemplated suicide. Fortunately, I talked her out of that, but there were desperate times. Helen realised that she was married purely out of habit. She didn’t like Alan and told him so. After a few months, they split. Helen had the three girls in the house they owned, he moved in with a relative down the coast.
We met several times over those months of her break up. Sometimes we made love, but most times not where she was in such an emotional mess. She didn’t want me to move in with her, preferring to keep me at a distance until she sorted her mind out. I would have made that break from my Marriage, I would not have liked it, but I felt as if I owed it to her. In truth, I was as much an emotional wreck as she was. I had fallen in love with this woman and was now enmeshed in a triangle between my wife and her. It wasn’t how it was supposed to be and I was completely confused.
Eventually, Helen got her life back on an even keel. Had begun classes for bookkeeping, something she had been doing for a number of years for local businesses, but without the qualification. She moved home and gradually settled down. She also made it clear that I was not required. She might call me to come and visit if the girls were away, but those times were purely on her own terms and that was fine with me. I have to say that, each visit was as satisfying as our first time and well worth the two hour drive. Helen had never had a cock in her mouth. I promised not to cum unless she wanted me to. She didn’t. Neither had she ever been fucked in the arse. Between me and a vibrator, Helen was soon screaming the place down as I unloaded in her beautiful arse.
And then she began to experiment. She sent me a couple of photographs of her, in a leather bondage suit, being serviced by two men she had met online. Helen was entering into a period of her life where her new found freedom was to be explored to the maximum. I worried somewhat, that I had woken the Kraken and advised caution. She laughed it off, but I felt responsible and more than guilty for my part in her current situation.
Our contacts became fewer and further between. Helen didn’t answer many of my emails and blanked my calls quite often. That was okay with me, but it didn’t stop me worrying about her. I doubt I would have forgiven myself if I read she had had some kind of tragic end.
The last I heard from Helen was to advise me she had found a new love and was to be married soon. She was happy and the guy knew how to keep her happy in all ways. Conscience absolved, I was happy for her and wished her all the love in the world. She deserved it and I believe, had at last found it.
Actually, it wasn’t the last time I heard from her. She let me know that she is a grandmother now and that she hoped I was okay and that, yes, she was happy and settled and complete, for the first time in her life. The thank you was most poignant.
Without doubt, Helen’s receptive body and her capacity for love have found no equal on my part. I am delighted that she has now found the joy that sex can bring and with a partner who provides her every need. It is my privilege to have helped her discover that.