Ladyboys Moving to Thailand and my first Ladyboy
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It had taken some time to get over my divorce, not that it had been particularly messy or sordid, quite the contrary as we had settled everything in a business-like and polite manner. It was simply that after 15 years of marriage, I found the transition back to bachelorhood to be difficult.
I had always thought myself to be fairly open and friendly and enjoyed meeting people and good conversation, but now I was conscious of the fact that I was treated with some degree of scepticism. I could almost hear people questioning my motives if I started to chat to their wives and girlfriends and finding somebody outside my small number of friends or work colleagues was also difficult. I soon learned that a 40 year old man could not simply go up to an attractive lady and start chatting as I had done in my youth.
I tried a couple of dating agencies and met a number of women but most wanted long term relationships while I simply wanted good company and yes, I admit it, some good sex as well! I was just not ready to get involved on a full-time basis just yet.
However, one night I found an online agency which operated a chat room and I became hooked. I had found a place where I could converse with others from all over the world and have some fun at the same time. That is how I found Heather or “Professional Lady” as I first knew her. Soon we were chatting two or three times a week, sometimes for an hour or more. As our on-line relationship developed I started to find out more and more about her. She was also divorced and 42, ran her own small travel agency employing about 20 people in their two offices. Although she travelled widely and met lots of people, most of her friends were business related and she also had trouble meeting people outside of her normal sphere. She once said she just wanted somebody who cared not what she did for a living or how much money and influence she had – she just wanted a total change in her life away from work.
Although we chatted frequently about sex, we never went for cyber-sex, although we both admitted later that we had used the chat rooms for that as well. It just did not seem appropriate or necessary. Our relationship developed from a shared feeling of loneliness and a willingness to share problems and thoughts.
After a couple of months I had the opportunity to go to Scotland for work and, as luck would have it, to Edinburgh itself where Heather was based. The next time we chatted I told her I would be in her city and she recommended a small but good hotel and booked it for me through her contacts. The opportunity to meet was too good to waste so I asked her if she would like to meet for dinner and she accepted, all of which lead me to be sitting in the corner of my hotel bar just before our agreed meeting at 7 o’clock.
We had not even swapped photos but I knew as soon as Heather walked in whom she was. Her slim petite frame was clothed in a dark blue pin-striped business suit, the skirt tailored to knee length displaying well shaped legs and modest heels beneath. Soft red wavy hair framed her face which gave no hint to her true age. If anything, she would have passed for somebody ten years her junior. I got down from my stool and greeted her – an awkward moment as I felt that I knew her so well that I should kiss her, but my restraint saw me simply proffer a hand which she took into hers.
The initial clumsiness soon passed as I ordered drinks and we started to chat as if all our other conversations had been person-to-person instead of over the faceless internet.
As we finished our drinks Heather asked me where I would like to go? What sort of food did I like?
“Well” I said remembering the conversation indicating that she was looking for somebody who would make decisions for her “I have booked us into an Italian just around the corner. It was recommended by a colleague who said it was quiet with great food and a wonderful wine list.”
Heather smiled “Well let’s go then and see what a stranger in my City has found.”
We walked the short distance to the restaurant, took our table and enjoyed one of the best Italian meals that I had eaten outside of Italy. The waiters were attentive, but kept in the background enabling us to enjoy the food and wine and each others company. Time passed all to quickly and soon I realised that we were the only people left in the restaurant. It was time to go, but neither of wanted the evening to end.
It was Heather who suggested a nightcap and countered my suggestion of a return to the hotel’s bar by saying that her apartment was only a short way away so why didn’t we go there?
A five minute cab ride took us to her home, a top floor flat in a refurbished Victorian townhouse just outside the city centre. Heather showed me into the lounge, a huge high-ceilinged room tastefully furnished with a mixture of antiques and soft modern lounge chairs and sofa. She moved across to the stereo and selected a jazz CD before turning to me and indicating to the sofa.
“Sit down while I get us something” she was already moving towards the door “Coffee? Scotch?”
“Both would be nice, thank you” I replied
“Well the Scotch is in the small cabinet, pour us both one and I will make some coffee. Back soon.”
She disappeared out of the door while I went over to fix the drinks. I found a bottle of expensive malt whisky and poured a moderate measure into two small cut glass tumblers, before returning to my seat and placing them on the coffee table.
As I surveyed the room it became clear that Heather was either independently wealthy or that her business was flourishing. The antiques and other ornaments were both tasteful and expensive and would be way beyond my means (and I thought of myself as comfortably well off). As my eyes continued to look around the room, I was aware that Heather was moving around the flat before the unmistakable smell of freshly brewed coffee heralded her return. As she re-entered I was surprised and delighted to see that she had changed.
Gone was the formal business suit and shoes to be replaced by a loose fitting blouse and slacks. The transformation was complete; the business woman was gone to be replaced by an elegant woman who seemed to ooze a modest sexuality.
“I hope you don’t mind me changing,” her voice light, almost smiling “I hate suits, but they are expected by many of my clients.”
“Not one bit” I replied meekly “I think the casual “you” suits you very well”
Heather placed the tray of coffee down on the table and picked up her glass “Well thanks for a lovely meal and the chance to meet after all these weeks,” we clinked glasses and both sipped the mellow pale yellow whiskey.
“Yes, I have had a wonderful evening and I hope that this is just the beginning of a new part of our relationship.” My reply was said with sincerity which I hoped was conveyed with honesty; it certainly seemed to have that result as she leaned forward again and we clinked glasses again. “Yes I hope so as well” she replied “ it would a shame if this was to be the only time.” She looked down at the point, perhaps a moment of too much honesty?
I placed my glass on the table and move slightly in my seat before looking towards her. I held her gaze as my right hand came up to take the glass from hers and placed it on the table alongside mine.
We looked at each other both knowing I think that this was the point at which the relationship would take that further step.
I simply slowly leaned towards her until my lips were but a millimetre away from hers. I watched her eyes close as I leaned into that first kiss; a long soft kiss. Just light pressure from our lips at first, then both opening in unison as our tongues made that first tentative exploration. My hands moved up her arms as the kiss deepened, holding her shoulders in a firm grip as my tongue entered between her teeth to explore her own moist tongue and the warm wet cavern of her mouth.
Her eyes opened then, briefly, looking into the back of my own before closing again as I pressed my self lightly against her. That first kiss was truly memorable, I do not remember enjoying something so simple before, but eventually we broke apart. Slowly, neither wanting that first intimate contact to end.
“Heather?” I started to ask, but her finger stole into the gap and sealed my lips.
“No questions” she looked deep into my eyes “you know me well enough not to ask.” She paused, then added “I believe you know what I want. What I need. I trust you to give that to me without asking any more questions.”
Her eyes burned into mine. Memories of all those chat-room conversations flashed through my mind. Decisions were primarily to be left in her work; she wanted me to take control.
I returned her look as my eyes looked back into her deep green pupils. Without loosing her gaze my hands moved slowly down her upper arms before moving lightly across the front of her blouse. They easily found the large buttons which held this silk garment together, moving quietly to undo each button. I held her gaze still while my hands moved inside the fine material, barely touching her skin as they moved upwards again to ease the garment off of her shoulders, enabling it to slide down her arms. She moved slightly, enabling the garment to fall away completely.
Only then did my eyes move lower, tracing an imaginary line down from her chin into the valley between her small firm globes. Her breasts stood firm, encased in a simple dark blue lace bra with sheer cups that showed the outline of her hard nipples and dark brown aureoles to perfection. I was almost transfixed, but tore my eyes away to return to look back into hers. I saw a hidden question which needed an answer “Beautiful. Perfect” simple statements which emphasised that here was a beautiful woman with an outstanding body. In emphasis, my hands came back to cup them, each fitting wonderfully into the palms of my hands.
“Too small” she smiled “but thank you.” Now it was my turn to silence her which I did with a finger to her lips; pressing against them lightly.
Then still looking into her face my hands returned, first to her back to release the simple clasp, then to the front to pull the flimsy garment away and down over her arms. Now my eyes returned to her breasts, still standing firm despite the lack of support. I was drawn to them, and I bowed my head to each in turn running the tip of my tongue over each hard nipple, leaving a small trail of saliva over each as I tasted her soft flesh. I heard her moan – more like a soft whimper as my tongue traced over each breast again, my hands holding them up for my oral caress.
Gently at first then with more power, I sucked each nipple in turn into my mouth, letting my teeth caress the base of each hard nub as my tongue flicked easily over their ends. Heather moaned, louder this time; had I used too much pressure? Had I been too rough? I eased the pressure but a whimper and a hand told me that my attentions to her breast were Ok – needed even. I bit down firmly, feeling her left nipple grow further in my mouth as I did so, the tip pulsing against my tongue. I moved to the right one and applied the same degree of pressure and was equally rewarded. My hands reached up to squeeze her small globes, my fingers squeezing the blood from her breast flesh as I sucked more of her breasts into my mouth.
Heather was squirming on her seat now, her quiet, erotic moans filling the room. I raised my head from her breasts and released the pressure of my fingers and watched the pink return to the white areas where my finger tips had been.
My hands moved to the waistband of her slacks, easily releasing the string cord before easing under the material to pull them down her legs. Heather eased up slightly from the seat, enabling me to draw them over her hips. No panties gave me an unobstructed view of her soft red pubic bush as the material fell away. The lady was clearly prepared!
As Heather kicked off her slacks, my hands returned to her hips, my fingers tracing a line from each, down the valley above her thighs to rest each side of her mound. I slipped from the couch and moved quickly between her thighs which opened to receive me.
My first glance at her pussy showed me just how much this lovely woman had enjoyed my initial caresses. Traces of wetness glistened on her fine re hair as my fingers moved further to slowly caress each side of her opening. This simple touch was enough to stimulate their opening, revealing the soft pink inner lips which to my surprise and delight were large, much larger in fact than any I had seen or touched before. I bent my head; my tongue moving over each one, tasting her sweet musky juices for the first time.
As my tongue circled them, the lips seemed to grow, opening like a flower to reveal her hot moist centre and the little hood at the top. I blew my warm breath over them, she moaned, her head now thrown back as she revelled in her own erotic dreamlike state. I moved closer and drew a pussy lip between my own lips, sucking the juice from her. Those incredible lips grew more, the rush of blood turning them a darker shade of pink than her portal. My mouth moved to the other, sucking a little harder this time so that I could draw the soft flesh between my teeth.
“God help me Yessssssssss …..” the voice from above trailed off as she tried to ease herself off the couch to press herself against my mouth. I nibbled her flesh before moving upwards. A flick of my tongue was enough to spring her clit from its hiding place. What a clitoris it was; Heather was adorned with a clit of generous proportions, matching those wonderful pussy lips to perfection. I was in heaven as my tongue pressed against this beautiful appendage, before flicking upwards to leave it standing proud. As my lips bent to capture it, my fingers moved to hold her ample lips apart, easing into her body to release a generous amount of juice which ran over my fingers and down between her rear cheeks.
“Oh please, please, please don’t stop” again her voice faded away into a long ecstatic moan as my mouth drew her clit inside and my tongue started to flick easily over her. Heather was squirming now and only the pressure from my arms pushing down on her thighs kept me in contact with her succulent pussy. My tongue now started to move quickly over the end of her clit, strumming her flesh as she started to writhe beneath my face. I knew she was close to cumming but the speed and force with which it came surprised me.
Suddenly she arched herself upwards, forcing her pussy against my face, her hands clenching the fabric of the couch. “Ahhhhhhhhhh…” the moan now near a scream as her whole body went rigid. I felt something splash against my chin, then again. Surprised at first, I realised that Heather was ejaculating her pussy juice as she came. Another new experience for me, but one I delightfully received as I moved my mouth lower to catch her third and final offering. Her hot sweet nectar splashed into my mouth as her body, as quickly as she had cum, went limp falling back against the soft fabric of the couch.
My tongue moved slowly and gently to lap up more of her juice, but as it flicked over her engorged clit, I felt her wince. I moved lower then, concentrating on a lighter, feather-like touch on each pussy lip as she struggled for composure. “Mmmmmm Oh that was so good”. Heather’s voice was soft and low “It has been a long time” she added simply, as if she needed an excuse.
Slowly I moved up her naked body, planting small kisses as I edged upwards, lingering over each long nipple before reaching her face and planting a long languid kiss on her mouth. Her eyes opened briefly as I kissed her again, letting her taste herself on my lips as I settled down once again beside her on the couch. I looked down at her perfect body; it was hard to believe her age, such was the flawlessness of skin and the fine skin tone. Her thighs were still open and I could see those fabulous pussy lips, which I had not long ago held between my lips, displayed against her full bush.
Slowly she turned to me and kissed me. “My turn” she said breaking her kiss for a moment before moving to kiss my neck at the opening of my shirt. Unhurriedly she started to open my shirt, planting soft little kisses to my chest as she moved down. When she reached the waistband of my trousers she unhooked the belt before drawing the zip down. My hard cock was aching for release which, with a little help from me, was soon accomplished as she tugged my trousers and boxers down over my thighs. At this point I was concerned – nature had endowed me with a cock which, when fully erect, grew to eight inches and was three around. Many partners had been apprehensive or even put off completely at the thought of this entering their bodies, but Heather seemed unconcerned as she seemed to drift to the floor between my legs, taking my clothing away in the process.
Heather looked upwards into my face as she took my hard shaft between her soft warm fingers. She said nothing as her fingers played up the sides of my cock before reaching around its girth. Slowly she pulled my foreskin down to reveal my purple head, shining with pre-cum which oozed slowly from the tip. Keeping the head exposed, the fingers of one hand started to spread the viscous liquid over the head. She repeated my trick and breathed softly over the head, drying the cum before it was replaced with new. Then I watched as she bent her head, her tongue moving outwards to flick my taught flesh as she pressed kisses down my shaft, licking the valley between my balls, before kissing her way back to the tip. She ran her tongue around the crown, pressing it against the sensitive area at the ridge before forming her lips into a perfect O to take the very tip into her mouth.
Now it was my turn to throw my head back as she slowly pressed her mouth down onto my shaft, taking the first few inches into her mouth to let her tongue run over and around the head inside her. Her hands cupped my balls, the fingers of one hand playing in the sensitive area behind my ball sack while the other moved up and down my shaft, keeping the head fully exposed inside her mouth. Her technique was incredible and within a minute I was fighting the urge to unload into her mouth. I was meant to be in charge, she wanted me to take charge, but I had to summon all my reserves to do it.
My hands grasped her head, my fingers entwining her hair as I decided to enjoy her mouth. Slowly at first, I started to pump my cock into her mouth; I did not want to ruin things, but something inside me told me that this was what we both needed. On my seventh or eighth thrust, I felt my cock hit the back of her throat and I looked down to check if Heather was OK. My eyes were met by hers, big, beautiful and full of sexual desire. Then she looked down, at the same time forcing her head down again until my cock went to the back of her throat. That look will live me for a long time. It was then that I decided to go for broke and thrust harder. This time my cock entered the top of her throat. Heather spluttered around my flesh but did not look up or try to pull away. I thrust again, pressing further; I felt her gag slightly and then try to swallow. I pulled back and then thrust again, this time a little more of me penetrated. I moved my right hand to hold her under her chin at the top of her neck while my left held the top of her head.
With the next thrust I felt her swallow and suddenly my cock slide into her until my balls slapped against her chin. I saw her gag and felt her throat contract around me. I withdrew, letting her catch her breath before pressing back again. This time my cock seemed to move more easily and soon, for the first time in my life, I discovered the sensation of being deep throated. The tightness of the grip around my cock and the feel of Heather’s tongue as I withdrew between each gentle thrust was truly out of this world and in only a few thrusts I could feel my balls tighten and the urge to explode was upon me.
I told Heather that I was about to cum, but she took no heed. As she felt me tense, she impaled herself onto my member, letting the first spurt enter her throat directly from the tip lodged within it. She pulled back coughing slightly to take my second and third in her mouth. Then, as I looked down at her, she looked up at me and literally sucked my final discharge from my cock. I saw her swallow before letting her tongue bathe my sensitive engorged cock, taking away the final traces of my sperm.
Still holding my cock in her soft hands, Heather moved back to sit alongside me on the couch. Our lips touched in a kiss, then our tongues moved to find the other, enabling me to taste the heady cocktail of my own cum and her saliva.
“That was incred…” again her finger silenced me.
“Let me tell you a secret.” Heather looked at me. “You are only the second man who has ever cum in my mouth and the first who has cum in my throat.”
I could not believe it, apparently I was not the only one to experience deep throat for the first time that evening!
“II never thought or wanted to try and do it before. In fact I didn’t believe I could. But I thought that with you it would be good.” She looked into my eyes, a sincere, loving look. “I trusted that you would not hurt me despite your prize winning cock.” She smiled and gently fondled me again in her hands.
“How soon before this monster is ready again?” she squeezed my cock gently, effectively stopping it from going down beyond the half-way mark.
“Just as soon as I have prepared you to receive it” I smiled in reply, moving my hands down to her pussy once again to open those wonderful lips. This time my fingers separated her slick folds freely, a single finger gently entering her to the first knuckle with ease. “You have a beautiful pussy Heather” I added, “one that I plan to enjoy to the fullest.”
“Thank you kind sir “ she beamed back “Oh yes please more of that to start with.” While she spoke I had turned my finger inside her to stroke the inner wall of her pussy, enabling my thumb to stroke her clit which was still erect and very available.
I pulled her towards me kissing her deeply as my fingers played in my moist folds. The initial finger soon joined by a second, stretching her slightly, making her move around to better accommodate the twin digits. Her own hand started to softly pump my cock which now began to regain its strength. Rarely had I enjoyed two climaxes close together but the sheer eroticism of this evening provided all the strength I needed to pump blood back into my member.
The action of my fingers were now more urgent, alternating between caresses to Heather’s clit and inner walls, and jabbing thrusts as I finger fucked her. I could feel her building towards another climax as her face fell away from the kiss; her breathing coming in increasingly shorter breaths. I bent my head to capture one of her nipples, sucking and then practically chewing on the delightful flesh as my fingers worked their magic inside her. I felt her start to tense as she had a small orgasm, then another a few seconds later. I decided now was the time and moved quickly between her open thighs.
Those pouting pussy lips, now fully distended and open, hung to each side of the hot centre which awaited my now bloated cock.
I edged forward, my cock slipping over those lovely lips, twitching as it grazed her clit, before I plunged deep inside her in one single fluid motion. Her pussy seemed to suck me in as I pressed forward, I could feel her hot juice almost boiling around my cock, lubricating its advance into her.
I looked down to where our bodies joined, no more than a couple of inches still remained outside her as I savoured that first penetration.
“Ohhhhh please love me don’t make me wait” Heather was barely audible, her head once again thrown back against the couch as she sought to engulf more of me inside her.
I pulled back until the head nestled between her soft folds before thrusting back into her, my cock pressing against the tip of her clit as it stroked into her inner depths. The heat was incredible and I started to move faster and more powerfully, on each stroke attempting to reach new depths and corners of her pussy. I started to alter my angles as I sawed in and out of her, the sweat pouring off of me as I sought to drive her to new heights. Her sounds were now almost incoherent mumbles and cries as the tip of my cock started to batter her insides. I looked down to see that now, as she stretched to accommodate me, she was taking virtually all of my hard flesh into her tight body.
Feeling her climax start to build once again, I reached up with one hand to tweak her nipples, while the other delved beneath us, holding her up by her soft ass cheeks. As I thrust into her again from this new angle, her cheeks parted and my fingers stole beneath her to tease her anus. This was enough to start pushing her over the edge. As my fingers played with her nipples and ass, my cock reared itself inside her, pressing against her clit once again as I hammered into her. Her breathing became short pants and she uttered little moans. I could feel my own cock start to swell inside her as her pussy contracted around me. I pulled back once again before driving hard into her. I felt my balls against the cheeks of her ass as she fell over the edge into orgasm. Her inner muscles clenched me as I shot my sperm deep inside her. She trembled and went rigid as I shot into her again, feeling her own juices shoot over my cock as I flooded her insides.
A short sharp scream and her muscles tightened further, almost painfully so as she milked another spurt of juice from me, before she fell limp in the seat. I could feel my own blood coursing through my body, as the sheer effort of my cumming left me drained. I fell forward onto her heaving chest as I relaxed my grip on her body, my cock slipping partially out of her, enabling our combined juices to simply pour out of her.
I am not sure to this day how long we lay like that. When my senses recovered my prick was limp and I could feel cramp building in my legs. I moved to a more comfortable position and slowly looked over the sleeping Heather. Her breasts moved easily with her still heavy breathing, her pussy still gaped open between her pussy lips, enabling even more of our juices to escape through the open hole.
Slowly I stood up then bent to take her into my arms and carry her to her bedroom. I pulled back the quilt and laid her quietly onto the white sheets before creeping around to the other side of the bed. As I got beneath the quilt I felt her stir. sleepy eyes looked deep into mine “I guess it will be a little while before my monster is ready again?” She smiled a sleepy smile.
“I think it will take several hours” I grinned back at her.
“See you in the morning then” and she drifted back into sleep
I had always thought myself to be fairly open and friendly and enjoyed meeting people and good conversation, but now I was conscious of the fact that I was treated with some degree of scepticism. I could almost hear people questioning my motives if I started to chat to their wives and girlfriends and finding somebody outside my small number of friends or work colleagues was also difficult. I soon learned that a 40 year old man could not simply go up to an attractive lady and start chatting as I had done in my youth.
I tried a couple of dating agencies and met a number of women but most wanted long term relationships while I simply wanted good company and yes, I admit it, some good sex as well! I was just not ready to get involved on a full-time basis just yet.
However, one night I found an online agency which operated a chat room and I became hooked. I had found a place where I could converse with others from all over the world and have some fun at the same time. That is how I found Heather or “Professional Lady” as I first knew her. Soon we were chatting two or three times a week, sometimes for an hour or more. As our on-line relationship developed I started to find out more and more about her. She was also divorced and 42, ran her own small travel agency employing about 20 people in their two offices. Although she travelled widely and met lots of people, most of her friends were business related and she also had trouble meeting people outside of her normal sphere. She once said she just wanted somebody who cared not what she did for a living or how much money and influence she had – she just wanted a total change in her life away from work.
Although we chatted frequently about sex, we never went for cyber-sex, although we both admitted later that we had used the chat rooms for that as well. It just did not seem appropriate or necessary. Our relationship developed from a shared feeling of loneliness and a willingness to share problems and thoughts.
After a couple of months I had the opportunity to go to Scotland for work and, as luck would have it, to Edinburgh itself where Heather was based. The next time we chatted I told her I would be in her city and she recommended a small but good hotel and booked it for me through her contacts. The opportunity to meet was too good to waste so I asked her if she would like to meet for dinner and she accepted, all of which lead me to be sitting in the corner of my hotel bar just before our agreed meeting at 7 o’clock.
We had not even swapped photos but I knew as soon as Heather walked in whom she was. Her slim petite frame was clothed in a dark blue pin-striped business suit, the skirt tailored to knee length displaying well shaped legs and modest heels beneath. Soft red wavy hair framed her face which gave no hint to her true age. If anything, she would have passed for somebody ten years her junior. I got down from my stool and greeted her – an awkward moment as I felt that I knew her so well that I should kiss her, but my restraint saw me simply proffer a hand which she took into hers.
The initial clumsiness soon passed as I ordered drinks and we started to chat as if all our other conversations had been person-to-person instead of over the faceless internet.
As we finished our drinks Heather asked me where I would like to go? What sort of food did I like?
“Well” I said remembering the conversation indicating that she was looking for somebody who would make decisions for her “I have booked us into an Italian just around the corner. It was recommended by a colleague who said it was quiet with great food and a wonderful wine list.”
Heather smiled “Well let’s go then and see what a stranger in my City has found.”
We walked the short distance to the restaurant, took our table and enjoyed one of the best Italian meals that I had eaten outside of Italy. The waiters were attentive, but kept in the background enabling us to enjoy the food and wine and each others company. Time passed all to quickly and soon I realised that we were the only people left in the restaurant. It was time to go, but neither of wanted the evening to end.
It was Heather who suggested a nightcap and countered my suggestion of a return to the hotel’s bar by saying that her apartment was only a short way away so why didn’t we go there?
A five minute cab ride took us to her home, a top floor flat in a refurbished Victorian townhouse just outside the city centre. Heather showed me into the lounge, a huge high-ceilinged room tastefully furnished with a mixture of antiques and soft modern lounge chairs and sofa. She moved across to the stereo and selected a jazz CD before turning to me and indicating to the sofa.
“Sit down while I get us something” she was already moving towards the door “Coffee? Scotch?”
“Both would be nice, thank you” I replied
“Well the Scotch is in the small cabinet, pour us both one and I will make some coffee. Back soon.”
She disappeared out of the door while I went over to fix the drinks. I found a bottle of expensive malt whisky and poured a moderate measure into two small cut glass tumblers, before returning to my seat and placing them on the coffee table.
As I surveyed the room it became clear that Heather was either independently wealthy or that her business was flourishing. The antiques and other ornaments were both tasteful and expensive and would be way beyond my means (and I thought of myself as comfortably well off). As my eyes continued to look around the room, I was aware that Heather was moving around the flat before the unmistakable smell of freshly brewed coffee heralded her return. As she re-entered I was surprised and delighted to see that she had changed.
Gone was the formal business suit and shoes to be replaced by a loose fitting blouse and slacks. The transformation was complete; the business woman was gone to be replaced by an elegant woman who seemed to ooze a modest sexuality.
“I hope you don’t mind me changing,” her voice light, almost smiling “I hate suits, but they are expected by many of my clients.”
“Not one bit” I replied meekly “I think the casual “you” suits you very well”
Heather placed the tray of coffee down on the table and picked up her glass “Well thanks for a lovely meal and the chance to meet after all these weeks,” we clinked glasses and both sipped the mellow pale yellow whiskey.
“Yes, I have had a wonderful evening and I hope that this is just the beginning of a new part of our relationship.” My reply was said with sincerity which I hoped was conveyed with honesty; it certainly seemed to have that result as she leaned forward again and we clinked glasses again. “Yes I hope so as well” she replied “ it would a shame if this was to be the only time.” She looked down at the point, perhaps a moment of too much honesty?
I placed my glass on the table and move slightly in my seat before looking towards her. I held her gaze as my right hand came up to take the glass from hers and placed it on the table alongside mine.
We looked at each other both knowing I think that this was the point at which the relationship would take that further step.
I simply slowly leaned towards her until my lips were but a millimetre away from hers. I watched her eyes close as I leaned into that first kiss; a long soft kiss. Just light pressure from our lips at first, then both opening in unison as our tongues made that first tentative exploration. My hands moved up her arms as the kiss deepened, holding her shoulders in a firm grip as my tongue entered between her teeth to explore her own moist tongue and the warm wet cavern of her mouth.
Her eyes opened then, briefly, looking into the back of my own before closing again as I pressed my self lightly against her. That first kiss was truly memorable, I do not remember enjoying something so simple before, but eventually we broke apart. Slowly, neither wanting that first intimate contact to end.
“Heather?” I started to ask, but her finger stole into the gap and sealed my lips.
“No questions” she looked deep into my eyes “you know me well enough not to ask.” She paused, then added “I believe you know what I want. What I need. I trust you to give that to me without asking any more questions.”
Her eyes burned into mine. Memories of all those chat-room conversations flashed through my mind. Decisions were primarily to be left in her work; she wanted me to take control.
I returned her look as my eyes looked back into her deep green pupils. Without loosing her gaze my hands moved slowly down her upper arms before moving lightly across the front of her blouse. They easily found the large buttons which held this silk garment together, moving quietly to undo each button. I held her gaze still while my hands moved inside the fine material, barely touching her skin as they moved upwards again to ease the garment off of her shoulders, enabling it to slide down her arms. She moved slightly, enabling the garment to fall away completely.
Only then did my eyes move lower, tracing an imaginary line down from her chin into the valley between her small firm globes. Her breasts stood firm, encased in a simple dark blue lace bra with sheer cups that showed the outline of her hard nipples and dark brown aureoles to perfection. I was almost transfixed, but tore my eyes away to return to look back into hers. I saw a hidden question which needed an answer “Beautiful. Perfect” simple statements which emphasised that here was a beautiful woman with an outstanding body. In emphasis, my hands came back to cup them, each fitting wonderfully into the palms of my hands.
“Too small” she smiled “but thank you.” Now it was my turn to silence her which I did with a finger to her lips; pressing against them lightly.
Then still looking into her face my hands returned, first to her back to release the simple clasp, then to the front to pull the flimsy garment away and down over her arms. Now my eyes returned to her breasts, still standing firm despite the lack of support. I was drawn to them, and I bowed my head to each in turn running the tip of my tongue over each hard nipple, leaving a small trail of saliva over each as I tasted her soft flesh. I heard her moan – more like a soft whimper as my tongue traced over each breast again, my hands holding them up for my oral caress.
Gently at first then with more power, I sucked each nipple in turn into my mouth, letting my teeth caress the base of each hard nub as my tongue flicked easily over their ends. Heather moaned, louder this time; had I used too much pressure? Had I been too rough? I eased the pressure but a whimper and a hand told me that my attentions to her breast were Ok – needed even. I bit down firmly, feeling her left nipple grow further in my mouth as I did so, the tip pulsing against my tongue. I moved to the right one and applied the same degree of pressure and was equally rewarded. My hands reached up to squeeze her small globes, my fingers squeezing the blood from her breast flesh as I sucked more of her breasts into my mouth.
Heather was squirming on her seat now, her quiet, erotic moans filling the room. I raised my head from her breasts and released the pressure of my fingers and watched the pink return to the white areas where my finger tips had been.
My hands moved to the waistband of her slacks, easily releasing the string cord before easing under the material to pull them down her legs. Heather eased up slightly from the seat, enabling me to draw them over her hips. No panties gave me an unobstructed view of her soft red pubic bush as the material fell away. The lady was clearly prepared!
As Heather kicked off her slacks, my hands returned to her hips, my fingers tracing a line from each, down the valley above her thighs to rest each side of her mound. I slipped from the couch and moved quickly between her thighs which opened to receive me.
My first glance at her pussy showed me just how much this lovely woman had enjoyed my initial caresses. Traces of wetness glistened on her fine re hair as my fingers moved further to slowly caress each side of her opening. This simple touch was enough to stimulate their opening, revealing the soft pink inner lips which to my surprise and delight were large, much larger in fact than any I had seen or touched before. I bent my head; my tongue moving over each one, tasting her sweet musky juices for the first time.
As my tongue circled them, the lips seemed to grow, opening like a flower to reveal her hot moist centre and the little hood at the top. I blew my warm breath over them, she moaned, her head now thrown back as she revelled in her own erotic dreamlike state. I moved closer and drew a pussy lip between my own lips, sucking the juice from her. Those incredible lips grew more, the rush of blood turning them a darker shade of pink than her portal. My mouth moved to the other, sucking a little harder this time so that I could draw the soft flesh between my teeth.
“God help me Yessssssssss …..” the voice from above trailed off as she tried to ease herself off the couch to press herself against my mouth. I nibbled her flesh before moving upwards. A flick of my tongue was enough to spring her clit from its hiding place. What a clitoris it was; Heather was adorned with a clit of generous proportions, matching those wonderful pussy lips to perfection. I was in heaven as my tongue pressed against this beautiful appendage, before flicking upwards to leave it standing proud. As my lips bent to capture it, my fingers moved to hold her ample lips apart, easing into her body to release a generous amount of juice which ran over my fingers and down between her rear cheeks.
“Oh please, please, please don’t stop” again her voice faded away into a long ecstatic moan as my mouth drew her clit inside and my tongue started to flick easily over her. Heather was squirming now and only the pressure from my arms pushing down on her thighs kept me in contact with her succulent pussy. My tongue now started to move quickly over the end of her clit, strumming her flesh as she started to writhe beneath my face. I knew she was close to cumming but the speed and force with which it came surprised me.
Suddenly she arched herself upwards, forcing her pussy against my face, her hands clenching the fabric of the couch. “Ahhhhhhhhhh…” the moan now near a scream as her whole body went rigid. I felt something splash against my chin, then again. Surprised at first, I realised that Heather was ejaculating her pussy juice as she came. Another new experience for me, but one I delightfully received as I moved my mouth lower to catch her third and final offering. Her hot sweet nectar splashed into my mouth as her body, as quickly as she had cum, went limp falling back against the soft fabric of the couch.
My tongue moved slowly and gently to lap up more of her juice, but as it flicked over her engorged clit, I felt her wince. I moved lower then, concentrating on a lighter, feather-like touch on each pussy lip as she struggled for composure. “Mmmmmm Oh that was so good”. Heather’s voice was soft and low “It has been a long time” she added simply, as if she needed an excuse.
Slowly I moved up her naked body, planting small kisses as I edged upwards, lingering over each long nipple before reaching her face and planting a long languid kiss on her mouth. Her eyes opened briefly as I kissed her again, letting her taste herself on my lips as I settled down once again beside her on the couch. I looked down at her perfect body; it was hard to believe her age, such was the flawlessness of skin and the fine skin tone. Her thighs were still open and I could see those fabulous pussy lips, which I had not long ago held between my lips, displayed against her full bush.
Slowly she turned to me and kissed me. “My turn” she said breaking her kiss for a moment before moving to kiss my neck at the opening of my shirt. Unhurriedly she started to open my shirt, planting soft little kisses to my chest as she moved down. When she reached the waistband of my trousers she unhooked the belt before drawing the zip down. My hard cock was aching for release which, with a little help from me, was soon accomplished as she tugged my trousers and boxers down over my thighs. At this point I was concerned – nature had endowed me with a cock which, when fully erect, grew to eight inches and was three around. Many partners had been apprehensive or even put off completely at the thought of this entering their bodies, but Heather seemed unconcerned as she seemed to drift to the floor between my legs, taking my clothing away in the process.
Heather looked upwards into my face as she took my hard shaft between her soft warm fingers. She said nothing as her fingers played up the sides of my cock before reaching around its girth. Slowly she pulled my foreskin down to reveal my purple head, shining with pre-cum which oozed slowly from the tip. Keeping the head exposed, the fingers of one hand started to spread the viscous liquid over the head. She repeated my trick and breathed softly over the head, drying the cum before it was replaced with new. Then I watched as she bent her head, her tongue moving outwards to flick my taught flesh as she pressed kisses down my shaft, licking the valley between my balls, before kissing her way back to the tip. She ran her tongue around the crown, pressing it against the sensitive area at the ridge before forming her lips into a perfect O to take the very tip into her mouth.
Now it was my turn to throw my head back as she slowly pressed her mouth down onto my shaft, taking the first few inches into her mouth to let her tongue run over and around the head inside her. Her hands cupped my balls, the fingers of one hand playing in the sensitive area behind my ball sack while the other moved up and down my shaft, keeping the head fully exposed inside her mouth. Her technique was incredible and within a minute I was fighting the urge to unload into her mouth. I was meant to be in charge, she wanted me to take charge, but I had to summon all my reserves to do it.
My hands grasped her head, my fingers entwining her hair as I decided to enjoy her mouth. Slowly at first, I started to pump my cock into her mouth; I did not want to ruin things, but something inside me told me that this was what we both needed. On my seventh or eighth thrust, I felt my cock hit the back of her throat and I looked down to check if Heather was OK. My eyes were met by hers, big, beautiful and full of sexual desire. Then she looked down, at the same time forcing her head down again until my cock went to the back of her throat. That look will live me for a long time. It was then that I decided to go for broke and thrust harder. This time my cock entered the top of her throat. Heather spluttered around my flesh but did not look up or try to pull away. I thrust again, pressing further; I felt her gag slightly and then try to swallow. I pulled back and then thrust again, this time a little more of me penetrated. I moved my right hand to hold her under her chin at the top of her neck while my left held the top of her head.
With the next thrust I felt her swallow and suddenly my cock slide into her until my balls slapped against her chin. I saw her gag and felt her throat contract around me. I withdrew, letting her catch her breath before pressing back again. This time my cock seemed to move more easily and soon, for the first time in my life, I discovered the sensation of being deep throated. The tightness of the grip around my cock and the feel of Heather’s tongue as I withdrew between each gentle thrust was truly out of this world and in only a few thrusts I could feel my balls tighten and the urge to explode was upon me.
I told Heather that I was about to cum, but she took no heed. As she felt me tense, she impaled herself onto my member, letting the first spurt enter her throat directly from the tip lodged within it. She pulled back coughing slightly to take my second and third in her mouth. Then, as I looked down at her, she looked up at me and literally sucked my final discharge from my cock. I saw her swallow before letting her tongue bathe my sensitive engorged cock, taking away the final traces of my sperm.
Still holding my cock in her soft hands, Heather moved back to sit alongside me on the couch. Our lips touched in a kiss, then our tongues moved to find the other, enabling me to taste the heady cocktail of my own cum and her saliva.
“That was incred…” again her finger silenced me.
“Let me tell you a secret.” Heather looked at me. “You are only the second man who has ever cum in my mouth and the first who has cum in my throat.”
I could not believe it, apparently I was not the only one to experience deep throat for the first time that evening!
“II never thought or wanted to try and do it before. In fact I didn’t believe I could. But I thought that with you it would be good.” She looked into my eyes, a sincere, loving look. “I trusted that you would not hurt me despite your prize winning cock.” She smiled and gently fondled me again in her hands.
“How soon before this monster is ready again?” she squeezed my cock gently, effectively stopping it from going down beyond the half-way mark.
“Just as soon as I have prepared you to receive it” I smiled in reply, moving my hands down to her pussy once again to open those wonderful lips. This time my fingers separated her slick folds freely, a single finger gently entering her to the first knuckle with ease. “You have a beautiful pussy Heather” I added, “one that I plan to enjoy to the fullest.”
“Thank you kind sir “ she beamed back “Oh yes please more of that to start with.” While she spoke I had turned my finger inside her to stroke the inner wall of her pussy, enabling my thumb to stroke her clit which was still erect and very available.
I pulled her towards me kissing her deeply as my fingers played in my moist folds. The initial finger soon joined by a second, stretching her slightly, making her move around to better accommodate the twin digits. Her own hand started to softly pump my cock which now began to regain its strength. Rarely had I enjoyed two climaxes close together but the sheer eroticism of this evening provided all the strength I needed to pump blood back into my member.
The action of my fingers were now more urgent, alternating between caresses to Heather’s clit and inner walls, and jabbing thrusts as I finger fucked her. I could feel her building towards another climax as her face fell away from the kiss; her breathing coming in increasingly shorter breaths. I bent my head to capture one of her nipples, sucking and then practically chewing on the delightful flesh as my fingers worked their magic inside her. I felt her start to tense as she had a small orgasm, then another a few seconds later. I decided now was the time and moved quickly between her open thighs.
Those pouting pussy lips, now fully distended and open, hung to each side of the hot centre which awaited my now bloated cock.
I edged forward, my cock slipping over those lovely lips, twitching as it grazed her clit, before I plunged deep inside her in one single fluid motion. Her pussy seemed to suck me in as I pressed forward, I could feel her hot juice almost boiling around my cock, lubricating its advance into her.
I looked down to where our bodies joined, no more than a couple of inches still remained outside her as I savoured that first penetration.
“Ohhhhh please love me don’t make me wait” Heather was barely audible, her head once again thrown back against the couch as she sought to engulf more of me inside her.
I pulled back until the head nestled between her soft folds before thrusting back into her, my cock pressing against the tip of her clit as it stroked into her inner depths. The heat was incredible and I started to move faster and more powerfully, on each stroke attempting to reach new depths and corners of her pussy. I started to alter my angles as I sawed in and out of her, the sweat pouring off of me as I sought to drive her to new heights. Her sounds were now almost incoherent mumbles and cries as the tip of my cock started to batter her insides. I looked down to see that now, as she stretched to accommodate me, she was taking virtually all of my hard flesh into her tight body.
Feeling her climax start to build once again, I reached up with one hand to tweak her nipples, while the other delved beneath us, holding her up by her soft ass cheeks. As I thrust into her again from this new angle, her cheeks parted and my fingers stole beneath her to tease her anus. This was enough to start pushing her over the edge. As my fingers played with her nipples and ass, my cock reared itself inside her, pressing against her clit once again as I hammered into her. Her breathing became short pants and she uttered little moans. I could feel my own cock start to swell inside her as her pussy contracted around me. I pulled back once again before driving hard into her. I felt my balls against the cheeks of her ass as she fell over the edge into orgasm. Her inner muscles clenched me as I shot my sperm deep inside her. She trembled and went rigid as I shot into her again, feeling her own juices shoot over my cock as I flooded her insides.
A short sharp scream and her muscles tightened further, almost painfully so as she milked another spurt of juice from me, before she fell limp in the seat. I could feel my own blood coursing through my body, as the sheer effort of my cumming left me drained. I fell forward onto her heaving chest as I relaxed my grip on her body, my cock slipping partially out of her, enabling our combined juices to simply pour out of her.
I am not sure to this day how long we lay like that. When my senses recovered my prick was limp and I could feel cramp building in my legs. I moved to a more comfortable position and slowly looked over the sleeping Heather. Her breasts moved easily with her still heavy breathing, her pussy still gaped open between her pussy lips, enabling even more of our juices to escape through the open hole.
Slowly I stood up then bent to take her into my arms and carry her to her bedroom. I pulled back the quilt and laid her quietly onto the white sheets before creeping around to the other side of the bed. As I got beneath the quilt I felt her stir. sleepy eyes looked deep into mine “I guess it will be a little while before my monster is ready again?” She smiled a sleepy smile.
“I think it will take several hours” I grinned back at her.
“See you in the morning then” and she drifted back into sleep
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