About two years ago I decided, for a number of reasons, to stray from my marriage. Not least because with my husband, who is more than thirty years my senior and whom I love dearly, there had been no physical relationship whatsoever for somewhere around twelve years. After such a long period of time of living in a relationship more akin to one like father-daughter, I realised that I didn’t want to lose out on what possibly might be left of just a few years of sensual pleasure life might still hold in store for me. It was not an easy step to take – indeed, it was against all the principles I had held up in the past.

By that time I had already made some contacts on-line, interestingly on a word-game site which apart from the game itself also had a chat facility. This in turn was used by some players for the exchange of saucy messages, and for some more steamy chats. (More about this perhaps in another story) One of my friends from there pointed me to another app specifically designed for flirting, chatting and the exchange of (sometimes very explicit) photographs.

Once I had signed up and found my way round that app, it didn’t take long to find myself engaged in a number of conversations with men from various parts of the UK (and potentially other parts of the world). Those conversations were to a great extent conducted in the form of tags to the uploaded photograph(s). One man soon caught my attention with his customised statements (as opposed to standardised tags provided by the app) and comments on my photograph. What struck me most about his photos were his piercing blue eyes and cheeky smile. He was ruggedly handsome, in his mid-forties, and as he told me, about 5’8 tall. After a few weeks of chatting on an almost daily basis, we were discussing the possibilities of meeting up, and soon an opportunity arose for me to get away from home for a night.

Once we had agreed on the date, we played through some scenarios on what would happen when we met. He used quite explicit language, and the scenarios he painted were exceedingly exciting. Closer to the day we exchanged phone-numbers, just to be able to stay in touch if necessary. And then, the last few days before our planned meeting, he did not come on-line. I was confused, and not quite certain what to do. On the train I decided a last ditch attempt and with trembling fingers I sent him a text-message, without much hope for getting a reply: “Last chance! Are you still interested in meeting up?” Oh yes ! He was interested and would shortly be on his way to the big city. I got exact instructions what to do: After checking in (and texting him the name of my hotel and my room number) I was to take a shower, change into some sexy lingerie, and then wait for his arrival. I should be prepared to be taken immediately on opening the door. The rest of my journey passed in a haze of excited anticipation – but also worry. Had I gone totally mad? Meeting up with a virtual stranger with whom I had not even exchanged a word in person in a hotel-room was perhaps not the safest thing to do. The situation could so easily get out of hand – what kind of person would he be?

Pushing all negative thoughts aside (although they always lingered somewhere in the back of my mind), I decided that it was a delicious adventure and well worth the risk. I did as instructed and waited, giddy with excitement and anticipation, my juices starting to flow just at the thought of things to come. Finally a text message announced his arrival within the next five minutes, my heart-rate going up, my breathing becoming heavier. A knock on the door, a flash of those piercing blue eyes, a smile, a barely whispered “hello” – and being pinned against the wall, hands and tongue exploring my body, fingers in my secret places. After a few minutes and a few steps further into the room, he took off his top, revealing a number of tattoos (well, I had seen some of them on his photographs), ordering me to get on my knees, feeding me his cock, making me gag and choke. Oh, this was so much better than all the fantasies we had spun! It almost felt like an out-of-body experience – this can’t be me, the conservative, insecure, shy me! And yet, it was so real! Well, not least because the sharp slaps on my bottom while being taken from behind, kneeling on the edge of the bed, kept me firmly within the real world.

I don’t remember how often I climaxed– the whole situation was so erotic, exciting, a totally new kind of experience for me – not only had I been starved of physical attention of any kind for many years, but never in my life had I been dominated in this way before. After around forty minutes, and a shared orgasm, we finally managed to introduce ourselves properly, albeit somewhat breathlessly.

While cuddling, we chatted about our lives and various experiences in general. He was quite easy to talk to, although at times I struggled with his northern accent. Quite openly he told me that he had been quite a bad boy in his youth. Some of his stories I found rather intriguing, giving me an insight into a world very different from my sheltered upbringing. Possibly this totally different background was part of the attraction, and certainly the strong erotic energy I felt emanating from him. After a while we were ready for an encore.

During our on-line conversations the subject of anal intercourse had come up. Had I tried it? Did I like it? Was I up for it? Previously I had never liked my bottom being fingered, but I was curious nevertheless, and I had told him that I was prepared to try it. Now, with passion running high, that moment had come. He made me kneel at the edge of the bed, with one hand pushing my head down, grabbing my hair. He fingered my bottom, sticking up high in this position, using spittle as lubricant. Never before had I been treated like that. It was exciting and a bit scary at the same time. When he tried to enter me I flinched, tried to get away. But there was no escaping his grip, and I will never forget his words: “Stay there! You can stand a bit of pain!” What followed was an intense combination of excitement, pain, and, once I relaxed, lust. This mixture of sensations was truly mind-boggling. Although I didn’t climax in this way, it was a highly sensually charged experience.

Once we had recovered our breath and cleaned up we dressed and went for dinner to a Chinese place nearby, followed by a stroll around the area and a brief stop for coffee. There were still a couple of hours left before he had to catch his train, so we went back to my room for some more cuddles and sensual play. In the lift – my room was on the 8th floor – he slid his hand between my legs, pushed me against the wall, and we kissed until the door opened on my floor. With a twinkle in his eyes he told me that he had always fancied playing in a lift.

I was well and truly fascinated by this man. Never had I met someone like him before; rough and sensual, playful and serious, and very gentle and tender when we parted at the end of the evening.

About six weeks later we met again. This time we had decided that he would stay for the night, since it was a weekend. My excuse to stay away from home was that I was attending a friend’s graduation party, which would surely last too long to travel all the way back late at night. Of course I did attend part of the celebration, but left early in the evening. Unfortunately, after I had booked my room a couple of days earlier, I skipped down the garden path in joyful anticipation, tripped, and holding a bunch of keys in my right hand, crashed against the frame of my back-door. My hand swelled up immediately, but I could still move all my fingers. I wasn’t sure whether anything was broken (possibly I did break a bone or two) but I decided not to have it checked, with the argument that there was not much doctors could do in such a case. And, of course, I feared that I would have to give up on my plans for the weekend.

By the weekend, my hand was not exactly a pretty sight, swollen and bruised in dark blue hues, and quite painful. Also, of course, I could not use it properly, each movement of the little and the ring-finger causing a wave of pain, but all bearable. I was determined not to let this spoil my fun. Again, I texted him the number of my room where he joined me sometime in the early evening. His concern about my hand was almost touching. He gingerly helped me to undress (and later on, dress again), the sex we had was much more tender – but no less exciting than the first time. For dinner we went to an Indian restaurant this time. I remember that I was wearing a black, knee-length shift dress, lace-top stockings, a necklace with chunky red beads, golden ball earrings, and a red leather-jacket. When we selected from the buffet, he stood close to me, and at one point slightly brushed his hand over my hips and bottom – naughty, but a very gentle gesture. I acknowledged that gesture wordlessly with a smile on my lips and a look into his blue eyes. After dinner we went for a stroll – he offered me his arm, and I could see the pride in his eyes to be walking with me arm in arm. Back in our room I told him how nice I found that moment in the restaurant, and his answer was: “You looked so sexy in that dress with your baubles – I couldn’t help it”.

At one point later that evening, I stood at the foot-end of the bed, undressing while he looked on, playing with himself. Again, this was a totally new situation for me, and I threw him a questioning look. When I heard his words: “Woman! You have no idea how much you turn me on!” I was flattered, amazed that I could even have such a reaction from a man. I really felt special.

At the same time, I sensed some vulnerability in him and I realised that he was fighting his own demons in regard to body insecurities and stamina – I assured him that there was need for him to worry, that he was the sexiest guy I had ever met.

The rest of the evening we spent cuddling, chatting, stroking, drifting off to sleep, waking up in each other’s embrace, falling asleep again. In the morning we found ourselves spooning; I felt his hard cock between my bottom cheeks, while he reached across my body to rub my clit – gently, slowly, taking his time. Only after he had made sure that I had climaxed, he took his turn – more akin to making love rather than just sex.

We parted company soon after breakfast, but agreed that next time I would come to his place. I already had a date about four weeks later in mind when my stay in the big city was required for a few days, a Sunday evening included, when we could meet. Over the next weeks we chatted almost daily on-line, made plans of how to arrange travel for our next meeting, what we would do, etc. Once I asked him what really turned him on- he said that he would like me in a fish-net body-suit, a collar, high heels. Well, I couldn’t quite imagine myself in that kind of outfit, but I went shopping for fishnet tights, and just to be on the safe side, some crotchless fishnet tights (and another pair in a different design). A collar I made myself – with satin and velvet ribbons to which I fixed a brooch of glass crystals. I was rather pleased with the result, having created a quite elegant piece of adornment. Also, I bought myself a new body-hugging skirt and studded sandals for that weekend. I could hardly wait for the time to pass.

We continued with our flirty, sexy and naughty, but also at times serious chats, and the closer the time of the next meeting came, the higher the anticipation rose. For some reason, on the Thursday before our meeting, the atmosphere changed. He came over as aggressive and argumentative. I do not remember how we ended up on the subject about chatting with other people on the site and looking at their private pictures. Yes, I was chatting with a few other people as well, and yes, I had looked at some of the naughty pictures, too – after all I got quite a lot of them offered to me, many more than I cared to look at. But that was what the site was for – and since there were people from all over the world on there, the chances of meeting anyone else were more than remote. I must have said something that displeased him greatly, because the last message I got from him was “I don’t want to see you”. In an instant, totally unexpected, all our conversations disappeared before my eyes – he had blocked me! I couldn’t understand what had happened – thought it was a poor joke he was playing at me. Frantically I sent him a text message, asking for clarification. No reply! I was devastated, couldn’t comprehend what just had happened. I felt as if I were in free fall off a cliff, about to shatter on the ground. I was dumb-struck, totally lost, close to tears. Of course I could not allow myself to cry – the reason would have been very difficult to explain to my husband.

The next couple of days passed in a haze. I hoped he would get in touch with me, telling me it had all been a mistake. Not only did I wonder what happened, but the bigger question was even the “Why?” Surely there must have been another reason than petty jealousy for his change of mind. I could accept that our affair, brief as it was, had come to an end, but I so desperately needed to understand what had led to that end. I came up with lots of theories, asked some of my on-line friends what they thought about this matter. But of course, it was all speculation and none of the solutions seemed satisfactory.

I never heard from him again. Needless to say, that Sunday evening in the big city, which I have always loved for many reason, I felt absolutely miserable. Everything in my hotel reminded me of the time we spent together, each ride in the lift reminded me of that little interlude; walking through the streets we had taken together, seeing the happy people in the restaurants we had visited together, all choked me up with tears I could not shed. Even some of my colleagues who attended the same event as I asked whether I was alright, because I looked so sad.

He continued to use the site we met on, and sometimes his picture would come up – I could look at it but not communicate with him; memories flooding my mind causing utter devastation because I could not understand what had happened. It took me a long time to accept that I will never entirely understand what went on in his mind, and it took me a good year before I could look at his photograph – when it popped up – without becoming emotional. Call me silly (and yes, I did scold myself more than once), but I could not help my feelings.

By now, almost exactly two years have passed since our last conversation, and looking back, I still wonder, but I also can cherish the wonderful (bitter-sweet) memories of those two meetings. My first affair will always have a special place in my heart. The occasional twinge of pain in my hand inevitably brings back to my mind some of the details I just described. Our first encounter was one of the craziest things I have ever done; he still was one of the sexiest guys I ever met. But I am aware that on so many levels he would not have been the right person for me for a long-term affair. Occasionally a newer photo of him pops up on my screen, and I even start to question what I really saw in him. Obviously, in the meantime I have far more experience in conducting (an) affair(s), and probably I am more laid back about such matters. Lovers come and go, some relationships last longer than others – this is just a fact of this kind of life-style.

As a consequence, I decided never again to focus on only one single person. Having more than one affair at a time should protect me from too strong an emotional attachment to any single person. But life is full of surprises and protective measures don’t always work – in recent weeks I had a sense of déjà vue.

… because this week, on my usual visit to the big city, I met up with a new man.

We spent a lovely evening together, and my world looks a bit brighter again.
As my next blog entry I had planned – and started to write – a piece about heart-ache and emotional attachment, a danger lurking on the path of illicit affairs and encounters. I had fallen into this trap a couple of years ago (not entirely surprising with a first affair), which I subsequently tried to avoid by a life-style including multiple relationships. And still, very recently I had a sense of déjà vue, got hurt in very similar ways. But enough of this at the moment– that’s the subject of the next post.

With nicer memories and thoughts on my mind, Leo suggested to write them up while they are still fresh. So here it goes …

About two weeks ago I started to chat with Jerry on MaritalAffairs. He fit my parameters quite well in terms of age group (he gave 48), physical description (around 6’), and he looked quite nice on his photograph, although photos on sites like this are rarely very flattering. Soon we exchanged e-mail addresses and continued our conversations on and off in this way. We told each other about our backgrounds and agreed that we would like to meet. We just had to find a suitable date.

Unfortunately, my time in the big city is fairly limited, and often the one evening per week I have there on my own is taken up with all kinds of engagements, or “play-dates” with one of my friends for that matter. Now for this week I had already a “date” planned (with Carl, whom I have not yet met in person, but we have been chatting for a few months, at times quite extensively on skype – once for almost three hours!), but Carl had already indicated at the end of last week that due to business matters he might not make it after all. So we left the final decision until midday of the day in question, and I told Jerry that if he is free on very short notice, we might be able to meet. As it turned out, Jerry’s wife had left that day for a business trip abroad, which left him open to spontaneous planning (talk about fate!), and Carl was quite happy to re-schedule our meeting (knowing that I could make alternative arrangements left him relieved of guilt for “letting me down”).

During the afternoon Jerry and I exchanged a few messages. He admitted to being quite nervous because he had never met up with anyone from the site before (having joined only a few weeks earlier), and not quite sure of how to go about it. He enquired whether I wanted to meet for drinks or dinner, which type of restaurant I preferred, etc. We agreed on a casual meal, in a place not far from my hotel with a laid-back atmosphere and leaving us all options open depending on how the evening would develop.

We took an instant liking to each other when we met (according to science, apparently subconsciously we decide within the first five seconds of meeting someone whether we like a person or not), and sauntered to our restaurant of choice. Over dinner and a bottle of wine, conversation flowed easily, first about our backgrounds, then about the more delicate subject of conducting affairs. When it came to more intimate details, Jerry sometimes blushed, which I found charming and endearing. Fortunately, for most of the time our table was out of earshot of others, so we could talk freely. At one point, after we had finished our meals, he took my hand and caressed it gently, the first physical contact, after a fleeting kiss when we met. It felt good, it felt right – and it felt natural to walk back together to my hotel.

However, there was a minor hurdle to overcome. Because I am a regular customer at my hotel I am quite well known to staff. Since I do have varying partners, even stay there on rare occasions with my husband, I have to be very discreet and avoid being seen with anyone in the public parts of the hotel. I always explain this to my companions, tell them my room number, and ask them to give me a few minutes to get to my room first before they join me. At the same time, at least for me, this adds to the excitement, brings home the forbidden character of what is to follow.

Following this procedure, Jerry joined me within minutes, and immediately we found ourselves in a tight embrace, kissing – hesitantly at first, but getting more passionate quickly. He explored my body with his hands, taking off my top, unfastening my bra, my jeans soon to follow the accumulating heap of clothes on the floor. While he licked and sucked my nipples, teasing and circling them with the tip of his tongue, I slid my hands under his top, feeling the warmth of his body. By now I was lying on my bed, Jerry kneeling beside me, caressing, exploring, stroking me, while I undid his belt and zip, to release him, and reciprocate his tender attention. With our excitement heating up, and having got rid of all remaining clothing, he set out to work the magic of his tongue on my sweet spot. With the help of a finger or two, delicious ripples of pleasure became waves of pure lust and he let me ride the crest of these waves, finally driving me over the edge. Now I was ready for his rock-hard member, not too big, not too small, to enter me and take me to new heights. It did not take long for him to climax, too – although he tried to hold back. His attempts to do so were not very successful, clearly due to a lengthy period of abstinence, as he apologetically explained to me later while we were cuddling up.

Once we had recovered our breath, our conversation again flowed easily from topic to topic, but this time more centred on sexual matters, covering likes and dislikes, positions, previous experiences. All the while we were caressing and stroking each other. Because of our physical closeness and our animated and animating conversation, it did not take long to feel our desires rise again. This time it was me on top, something I rarely enjoy (which I had mentioned to Jerry) but I clearly did this time, very much to his pleasure. Nevertheless, I cannot hold that position for long (too much work for my taste) and soon I found myself under him again. Between thrusts, Jerry asked for my “real age”, and I confirmed that I really was 52, as my profile states. With a grin he admitted that he had taken a few years off his own age, and that he was in fact 58 (which makes a difference of 10 years!) Well, all I can say is that he did the right thing. Not only does he appear younger than his years, but also I would possibly (probably?) not have considered his initial contact message on the site (even if my filters are set to a slightly wider margin than what I consider as my ideal age-group).

After another round of sticky and sweaty exercise on the bed, the time to part company had come. While waiting for him to finish his shower, I threw on a light kimono and lay on the bed, enjoying the afterglow of the evening. On saying our good-byes we agreed to meet again when an opportunity arises, even if it might be a few months before he has a chance to get away again. When he bent down to me, for a final tight embrace, he cheekily slid his finger between my legs which prompted me to threaten not to let him go as yet. Eventually I had to release him, though, and once he was upright, he licked his finger with a grin and twinkle in his eyes – and off he went, accompanied by my giggles until the door closed behind him.

… I paid another visit to “my” swingers’ club. For the last two years, whenever I am in my home-town (which is between two and four times a year), I try to go to the club for one or two evenings during the week I stay there.

The idea of exploring clubs of that kind as a safe alternative to meeting up with men met on-line (at the time I was still fairly green in that respect, although now, after having met a fair number of lovely men I am less worried about my safety) originated in a chat with one of my female friends. She, a lady of considerably proportions, told me in confidence that with one of her former partners she used to frequent clubs. I, never very confident about my looks and generally quite insecure about myself, thought “Wow, if she can do it, why shouldn’t I try this option?” The longer I thought about this idea, the more it grew on me, and I started to research the various clubs and their etiquette on-line. To cut a long story short, during my next visit “home” a visit to one of the clubs in town was on my itinerary.

Of course, the first time is rather nerve-wrecking, not knowing what to expect, how to behave, what to wear. Just to be on the safe side I had a male “chaperone” with me, strictly hands off, but to make sure that I felt comfortable in the club, to avert undesired approaches, and to have a quick escape if necessary. I was pleasantly surprised to find not only the “young and beautiful” there, but mostly people around my own age group (i.e. middle aged), of all shapes and sizes. Many of the people present spotted us as newcomers and were incredibly helpful in showing us around, explaining some of the rules, and generally making us feel welcome. Dressed in a black lace slip, black lace-top holdups, heels and nothing else, I blended well into the crowd at the bar. Soon I started chatting, and my companion, assured that I was in good company, left the club. Within a short while I had the most attractive man of the evening to myself, and we had amazing sex in one of the lockable rooms. I greatly enjoyed this first visit, knew that I had nothing to fear or to be insecure about, and ever since I went there on my own. Nowadays, two years later, I know that there is a good chance that I will see familiar faces, meet people I would even call “friends” of some kind, especially a couple with whom I have an interesting bond. (In brief: she is slightly bi and gets a kick from selecting women for her husband – a lovely man who is a bit shy and reluctant to approach women in the club – to play with and getting a description of events afterwards. However, she rarely joins in, nor does she usually watch.)

So far so good. But what about last weekend?

As it happened, I went to the club on two consecutive nights, Saturday and Sunday. The first night was not spectacularly exciting, although still nice. Quite unexpectedly I met a few people from the usual Friday crowd, which is rather unusual for a Saturday. I spent most of the time chatting with “friends” – some male but most were female – and was told that I should be honoured that the couple I was meeting, my friends mentioned above, were coming out on a Saturday, because apparently that’s their “stay at home” night (in reality they sometimes go to a different club, but not everybody knows that). When they finally arrived it didn’t take long before I was in a lockable play-room with him (selected by her!) and the window was covered – he is not keen on spectators. For some reason his performance wasn’t all that impressive, but then that’s how things go sometimes. After a while she joined us – stroking and caressing me, and she made me climax much better than he did on that occasion. Still, it’s not something I would go for by inclination – it was more a matter of curiosity.

I did not stay on all that much longer after they left, because there just were no interesting men present on that evening. Me leaving an hour before closing time is telling!

Since I had no other plans on Sunday night, I went to the club again. Sundays are usually much quieter – there were a few single men, two single ladies, one or two couples. I got to sit next to a Kurdish man at the bar, and we started chatting, and eventually ended up in a play-room. He was okay, but a little possessive, which is a turn-off for me in such a situation. He also covered the window (which I’m not so keen on with a stranger).

When I returned to the bar, I met another couple I knew from a previous visit (he is 70, takes heart-medication and thus cannot always perform properly. But he has a really dirty mind! She is in her early 60s, but nobody would believe that, seeing her long hair and nice figure).When we said hello, he pulled me towards him, took one of my tits out from my slip and licked and sucked it “to say hello properly”.

I had already assessed the little crowd with some naughty thoughts in mind, but wasn’t sure how to start off something – and my Kurdish friend was definitely not the right partner. I whispered to the older man to “set me up” which was a task right to his liking. So he said something along the lines “Come on, lass” and off we went to the play area. Still in the common parts he pinned me against a pillar, in plain sight of the trail of men that followed us, kissing, caressing, fondling and fingering me – my thong around my ankles – all the while encouraging the on-lookers to participate. Soon I had one guy kneeling before me, licking me, another one fondling my breasts from behind and him kissing and groping, too. It didn’t take long before we all went to a play area – not too big, but still with room enough for 4 to 5 people. By that time my “old” friend was in the background (he might even have got some more guys from the bar, but I’m not sure), although he kept on coming to ask whether I was fine and enjoying myself. At one point I leant forward from my little “cave” to briefly lick and suck him (not with much success, though), but at any time there were four guys around me. Once they had finished with me, a young man of 32 (as I learned later) spoiled me with his tongue – he was amazing!

Later on, in the shower, I chatted with three guys, all very interested in who I was, etc. and we exchanged a few details about our personal backgrounds. I think by the time I returned to the bar, the single ladies had left, and soon the “older couple” also made their way, so I was left with three men and the boss (who had actually let me in free that evening – which he has done on a few previous occasions. Well, I think I did my bit to keep business going!) While we chatted, the young man gave me a fabulous neck and shoulder massage, another one started to stroke me too, and soon I had one again kneeling at my feet, licking me, while I was wanking the two other guys. I am not usually keen on playing in the bar area, but since we were the only ones left, and the boss has seen lots of things anyway, I could relax and really enjoy myself again.

The memories of that evening still made me chuckle while writing this. Not only was it very erotic, but also quite naughty, asking my “old” friend to help me start the fun. At the same time, the process of writing reminded me how far I have come in the last 2 ½ years. Then, I was a sexually frustrated, insecure person, desperate for a little bit of physical attention, and in my mind past my prime – after all I was approaching the big 5 and worried that, if not life as such but at least the sexual aspect of it would finally be over. My situation seemed hopeless, but how wrong was I! During that period – sometimes a bit of an emotional roller-coaster – I turned myself around into a sexually adventurous person, far more open-minded than when I was younger. From strictly monogamous I became polyamorous (more out of necessity rather than by initial choice). I have met many people, obviously mostly men, in cyber-space and in real life. Some of them accompanied me only part of the way while others have become close and intimate (in every sense of the word) friends. They all contributed (and hopefully will continue in future) towards my becoming a sexually liberated and happy woman, with many exciting and wonderful stories to share.