My Threesome Curse

Why are my threesome bookings linked with disasters?

Seven Stories of Woe!

I have a curse when it comes to doubles bookings (threesomes). Sure, I may be reading too much into these experiences, I often do, but you be the judge. Read about my seven doubles experiences, not all that bad to be honest, but at the end you decide – should I risk another doubles booking?

The numbers speak for themselves, seven attempts, fourteen wonderful escorts, and from the ashes nine that I have never seen again and maybe only five that I am still seeing. That is not good results in anyone’s books – and the common point of failure is me. I am cursed when it comes to doubles bookings – see for yourself.

ThreePillows

Doubles encounter one.

I had been seeing escorts for several months by this stage, and I had mentioned to a few escorts that eventually I would like to try a doubles booking. Two escorts plus me, lesbian or straight, it didn’t really matter. My first experience was largely unplanned.

I had a dinner booking with an escort that I like and completely trust, and we had already seen each other on many occasions. Not long before the booking, she contacted me to tell me that an overseas escort that she admired (and had been in long-term contact with), was going to be in the country and would I consider changing the booking to my first double. With a lot of nerves and messages exchanged, I excitedly agreed that after dinner, we would be joined by this ‘mystery guest’.

In many ways it was a great evening, lots of conversation and a great feeling of fun. The sexual intimacy was a little strange. For one thing, at around that time last year, and as a result of stress and other issues, I was not always a great performer. OK, I’ll spit it out, I didn’t always achieve an orgasm. My companion knew this, and was probably a little nervous on my behalf, and protective of me. I also felt that she was also a little in awe of our international guest. Our guest picking up on these clues, was also a little reluctant to ‘step in’, and I felt that she was holding back.

In the end, the guest took charge and it was a very erotic experience. We never spoke about the elements of awkwardness and restraint, and we probably should have, but both of us had other things and issues going on in our lives, and we never really mentioned that booking again.

After a few more bookings, we had some other communication drama over some other issues, and we haven’t seen each other since. Her last message to me stated clearly that she would not take any future bookings from me. The double wasn’t the end of our long connection, but it did mark the start of a slide in the quality of our connection and probably didn’t help. I don’t blame the double for not seeing either of these two lovely escorts anymore, but then I didn’t know that I was cursed yet. For the record, I miss my companion from these experiences, she is a wonderful person and a wonderful escort and our ‘international guest’ was also a very lovely companion.

Doubles encounter two.

This story has an element of déjà vu already. Once again a long-standing regular, who knew of my desire to experience a doubles-booking, and knew a lot of other things about me as well. We had shared many experiences, much of the story of our lives and our hopes and dreams. I never disrespected our business arrangement, but felt that we were also friends and I trusted her to navigate me through any experiences.

Another ‘late notice’ experience, I had a big function on, and due to the nature of it, knew that I would be pretty drunk that evening. So although we were in the same city, we had said that we wouldn’t ‘catch-up’ that day. In post-event contact later that evening, we convinced each other to change plans and meet. We ended up together and in the process invited another escort into a booking for a double. This experience had lots of twists and turns that simply can’t be told. My alcohol fueled state meant that I was useless physically, but despite that, it was a weird, surreal and in most ways an enjoyable evening. After a long session, my regular was asleep, and I was finally able to ‘get hard’ and have sex with the companion that had joined us. I don’t think that went down too well with my regular companion.

In the days that followed we exchanged messages. Some issues from that night, as well as some that had perhaps been lurking beneath the surface, from the lengthy history we had together, played out. Apparently I had asked the companion that had joined us for her details – I don’t remember that, but I do believe that in my state, that was likely. I also felt hurt by what was said, and in the end, we stopped communicating and haven’t seen each other since that night. This really was a disaster. I miss her and how we were together, and I think I lost the start of a friendship in the process. Client-escort relations and friendships under these sort of circumstances are fragile things. She is probably glad to have seen the back of me!

Doubles encounter three.

This time I felt I had learned a lesson (or two). My double number three was different in many ways. This time it was with two escorts that I had only seen once before, each of them separately. So we had ‘good connections’, but no long-standing ‘regular-client’ relationship on the line this time. It was also planned, as one escort was finishing a tour of the selected city and the other escort was commencing theirs. Finally, it was also a pair of escorts that had doubled many times and in fact are quite renown for their doubles.

I may be using a bit of artistic license to call this a ‘tale of woe’ or ‘disaster’, as it was actually a wonderful booking. I can however claim that it was cursed – well sort of. One escort met me earlier, for us to have day-spa massages at the hotel. Once we had finished and were getting ready for dinner, she realized part of her outfit was back at her hotel. The doubles partner had to turn around, mid-travel, and go and pick it up (in extremely heavy traffic). To my benefit, I got to spend an unexpected extra hour talking to my first companion, in only her very sexy lingerie, while we waited for the rest of her outfit to arrive.

This was a ‘double dinner-date’, and after our hour-delay ‘fashion incident’, we had a great dinner and then retired to the hotel room. It was a wonderful evening, and not cursed beyond the fashion and traffic gods, other than one point, that is a comment on double bookings in general. As a ‘talkative client’, the sexual aspect of doubles is highly appealing, while at the same time the one-on-one intimacy is reduced – it is a weird effect for someone who is there for more than just the sex.

I had a great time, although I doubt that my ‘best contribution’ did anything more than get this amazing pair of women into ‘first gear’, if you can understand my meaning. They were very kind and attentive, but this was hardly the reenactment of a three-way porn scene, and that is all down to me – they are proven performers, I was the weakest link. That isn’t to say I wanted anything more, I was very happy with the sexual aspects of the evening – I’m just saying that it was all probably pretty ‘vanilla’ for my experienced guests.

I was left thinking that two separate dinner dates with these wonderful women, would perhaps have been a better outcome and fit, with the type of client that I am. My last meeting with one of these amazing escorts was that night, and I have seen the other escort on one occasion since. That is mostly a function of geography (I hope) and I believe that I am still a welcome client of both of these amazing escorts – but that wouldn’t support my story of woe. So let’s just say for now, the pathways with each escort are separate, and I am still to see one of my amazing companions from that night again, yet!

Doubles encounter four.

My journey returns to an adored regular. Another extended double, this time a lunch-date and then an afternoon together. We had been floating the idea of a double around for a while, it was to be with the preferred doubles partner of my long-standing companion. I arranged a ‘coffee-date’ for an initial meeting, and that went amazingly well, we got along famously as I knew we would. How could we not, given the shared connection, and how well I’m sure this escort ‘chooses’ all of her contacts and friends.

The lunch-date came, and lunch was magnificent. It was natural, fun, great food, company and ambiance – just an absolutely perfect start. We retired to the room and everything felt great, my escort companions started to undress – this was going to be the perfect day!

Just as I put my phone down and switched it to silent, starting to get undressed myself, a call came in. In the next half-an-hour, a complete melt-down at work occurred, this external disaster included the loss of my biggest ever work contract. I returned to my companions, with half-an-hour of the booking lost, and I struggled as valiantly as I could to maintain a mood of celebration and keep the terrible ‘work news’ out of my mind. My partners for the day did a great job, and it was still a wonderful booking, it just had the edge taken away from it by external events. So the curse is about more than the booking, in this case, it felt like the universe was conspiring against me as well – of course I’m joking, but the timing could not have been worse.

There is a real potential ‘curse’ element to doubles bookings however, one that is worth considering, if as nothing more than a tale of caution. Some of my Twitter contacts, knowing that I was about to write this article, suggested that I include, “what happens if you like the third-person more than your original escort companion?” Well that would be a problem, but it is not one that I can talk too from personal experience – that dynamic hasn’t happened to me yet.

What I can say however, is that I really, really, really like the companion who joined us that day – she is smart, beautiful, fun and lovely in every way. I would love to see her again, separately and in doubles, however so far, other than the coffee date, that is the only time that I have seen her. The partner that joined us for the day is one of the escorts that I think about when I’m in the mood I describe in ‘Single Booking Sadness’. There is a trap, curse, or consequence of a doubles booking that opens up this conundrum of ‘when is the right time’ to see someone introduced to you as part of a doubles booking. I still see my regular companion as often as I can, I would like to re-live this double experience again without the world outside collapsing, but I would also like to see the companion that joined us – unfortunately, you can’t have it all. This is another different curse, the curse of the spoilt client!

Doubles encounter five.

This encounter is still pretty fresh and painful. My fifth double was at the suggestion of another regular, who had previously recommended the other escort to me as a ‘stand-alone’ companion, when I was visiting another distant city. I had seen both escorts on a number of occasions, and I was very close to both of them, perhaps ‘too close’ in many ways.

We ended up in the same city for the first time, and my original companion made the doubles suggestion. This was to be a lesbian-double and they had long history and experience together. It was also going to be a chance for them to ‘teach me’ some new skills in the bedroom – something I was looking forward too. I don’t think of myself as a good lover, but part of my journey is trying to learn more and become a better sexual companion.

The plan was to see one of these wonderful women for a dinner booking one night, and then the other companion for an overnight the following evening. During the overnight on the second evening, after dinner, the companion from the first evening was to join us for a couple of hours in a lesbian double. I know complicated, still with me?

It was great, but even at the time something didn’t feel quite right. I still don’t know exactly what happened, but after the double, for the rest of the overnight, my companion was distant and we had no further sexual connection. We had a long history, a lot of past bookings and a very open dialogue. Since that evening, our conversation quickly moved to a ‘separation’ as client and escort and an ending of communication. Although there are real reasons and no doubt she is as upset with me as I am with her, I don’t think either of us understands exactly what happened, and why the wedge grew so quickly. As a result, I have not seen either companion since, although I hope that in the other case, it is purely a result of geography. In fact since the first publishing of this article, we have made arrangements to catch up again soon.

I have very strong feelings for my companions in this instance. I hope that in the case of the ‘ended’ connection, that her journey from here is wonderful. I hope that being on that journey without any connection to me is what she wants and what is best for her. I don’t feel that it is best for me, and I am still hurting about the conclusion of our long journey together. However if you care for someone, you want the best for them, even if you are not part of their story anymore. I don’t blame any aspect of the double for this, but it was a catalyst and it was also coincidentally the last time that we met. So I believe as I have stated already, that when it comes to doubles, I may very well be cursed by coincidence if not by the bookings themselves!

Doubles encounter six.

Since I wrote the first version of this article, I have two more threesome booking stories to tell. This story, ‘double encounter six’ is a very, very big (and involved) story and I will no doubt be mentioning aspects of it in articles for a long time to come. In fact I already have a name for a future story about the booking itself – ‘Once In a Blue Moon’ – but you will have to wait for that article, I am not emotionally prepared or able to write about it in detail just yet.

I can’t even bring myself to write much about this at all right now. The simplest description is that it was my last booking with my longest standing regular. It was our twenty-first booking together. I love this person, you will know this if you have read ‘Loving an Escort’ and the stories, themes and feelings from our almost 100-hours spent together are spread everywhere throughout my blog articles. I know that I shouldn’t be in love with her, but I am, and these are some of the hardest paragraphs I have written yet since I started this blog. My longest standing escort connection has come to a close and this doubles booking, our twenty-first booking is also very likely to be our last booking together.

We didn’t end our journey because of the booking, nothing bad happened in the booking at all. My lovely companion had already told me that she was retiring. So unless my adored companion returns at some point in the future, this was coincidentally our last meeting. I am so very happy for her, I hope that the future is everything that she wants it to be, she deserves every great and wonderful thing! But I am heart-broken. The double wasn’t cursed, but it feels right now as though I am doubly cursed! It was a great, emotionally charged, long and wonderful double-booking, that also happened to mark the end of such a wonderful and treasured relationship. It is so hard not to feel, that in some way, this isn’t still a curse of sorts. I cannot begin to describe how much I am going to miss this amazing person.

Doubles encounter seven.

Changing the mood I hope, my final doubles encounter (for now) was wonderful. Another escort that I adore and I am seeing as frequently as I can, invited me to participate in a booking with one of her doubles partners. I think, it may have been in part, for her to prove to me that doubles are amazing bookings. Of course you can see that already, I am not cursed, all of these seven bookings have been amazing. I am just a spoilt, emotional and over-thinking person. It was just that they connect to strange events, coincidences and unfortunately, a little bit too often, the end of the line on escort connections – especially with some adored regulars. These bookings are connected to both joy and sadness, rather than any ‘curse’ – but of course I needed a title for the article, and I have had more ‘shit-go-down’ (it would seem), when it is connected to double’s bookings than with any other form of booking.

Back to this booking. Simply put it was great fun. I was surprisingly nervous, not sure why, but I eventually relaxed into a couple of hours of fun, some great sex, and time spent with two lovely, beautiful and engaging escorts. Since it was relatively recent, I can also say that I haven’t seen either of these escorts since. That suits the ‘numbers’ that I used at the start of this article for emphasis, but I hope that it both cases, there is a road ahead – I certainly enjoy the company of both of these wonderful women.

So what about the future? Doubles encounter number eight!

If you are wondering, yes, these stories are all completely true – from my perspective at least. Obviously details are left out, as this is meant as a journey and thought starter, not a ‘tell-all’ revelation – as that is something that I would never do. Please be kind to me and the honesty I have shown, I know I am flawed, and I know that I am the one common connection – so without doubt, this is all my doing, where there are negatives in these stories, they are all entirely my fault.

There are fourteen wonderful escorts in these stories, and they really are all wonderful. Please don’t infer anything about them – they are all professional, all lovely, and any client would be privileged to meet any single one of them. I am so glad that I got to meet them, and despite anything you may read into this article, I would not give one of those bookings back – I am so humbled and privileged to have met them. That they allowed me to be a client when they did was a gift. Those that still see me as a client – well that is a gift beyond words.

As for the future, I am still just a little ‘gun shy’. I have had a booking with a wonderful escort who is a doubles-partner with another regular of mine, I like them both enormously and of course I adore the regular in question. So far, I have been reluctant to put that ‘preparation’ into an actual doubles booking. Why? I am so concerned now that it could end another pathway with a regular who is extremely important too me – that I don’t know if I can take that risk. I am angry at myself for being ‘risk averse’, as that is not normally me, and I know if I stop taking risks, that may have its own negative consequence.

I guess that makes this a great place to stop this article. Do you think I’m cursed? Do you think I’m an asshole? Do you think I should book this double and stop acting like a coward? Most of all, what do you think about doubles, and what stories would you like to add or tell? We all know that I am not cursed – I am a very, very lucky client.

Right now however, I am struggling with the end of my longest and deepest escort connection. I wish her all the best and thank the other people who continue to support me, see me and care for me.

Thank you for your readership. Please respect my anonymous companions for this (at times) very difficult and emotional story to write. Please also comment, share and discuss if you feel inclined. Thanks also to Carla, Amber, Marco and Debauched for their comments on the initial version of this article.

Xx SP 5 May 2017 (article updated 4 June 2017).

What Went Wrong?

Escort bookings have plenty of chances to go wrong!

Escort bookings make speed-dating look simple!

The first five minutes of a first escort booking are intense by any standard. Even if there has been plenty of preliminaries – screening, communication and deposits, it is still two people meeting each other for the first time – meeting to have sex.

There is so much that can go wrong. Even if the first booking is a huge success, every subsequent encounter is still intense, and the chance of something negative happening is greater than in most other human interactions. Often one of the people is left wondering – what the hell happened, what went wrong?

The pathway to rapid intimacy – stage one.

In those first five minutes you could fill an entire novel. The client is appraising his booking for the first time in real life, and if they are a decent client, they are trying to complete all the preliminaries and make the Escort feel at ease.

I assume at the same moment, the Escort is assessing safety, payment, venue (if an outcall), as well as the same human appraisal summations as the client – all in rapid time. Adrenaline and heart rates are high, time slows, nerves show through and not everything is taken in and absorbed – at least by me. Yet despite this, I think I know how it is going to go – good or bad – within the first 30-seconds. Humans are amazing at this early assessment stuff really.

I try and handle the payment immediately, with a hotel room tour, drink offer and light chat, all within the first minute. Then I try and give the Escort some space for her booking process, counting the money, texting security and whatever else she needs in her own process of getting organised. Then I (we) try to slow the pace down to get relaxed. It is amazing when this feels in-sync and the early chat is light, funny and pleasant. That is always a good sign.

First bookings with a chatty and open client.

I am a largely open book, within reason. I try and share personal material and insights into ‘who I am’ as part of a rapid journey to personal intimacy. This has risks, and if it is not reciprocated (at least in part) when I encounter an Escort who is very closed, or ‘mechanical’, then I know we are probably not going to meet again. Even if the sex is good, as I have explained in other blog articles, I’m here for physical and mental intimacy.

For a client and escort who are both talkative, and sharing, even at a relatively safe and superficial level, the pathway to intimacy is faster than in any other meeting of two human beings (this is only my opinion of course). That is part of the appeal, part of the addiction, part of what makes this a different experience to the rest of the slower, darker, more boring regular world. It also brings a supercharged environment for things to go wrong.

The pathway to rapid intimacy – stage two.

Both the client and escort build a connection. A lot of this is based on personal experience, short-cuts and assumptions. In showing each other our ‘good-sides’ and then both building an intimate portrait of each other, neither party has really learned those long, hard, lessons of what the ‘red-flags’ are, the danger areas, the no-go zones, or where those ‘crazy’ little parts we all hide inside are lurking.

There is a minefield lurking between the unicorns and rainbows we show each other – ready to be triggered at any time. When the client’s bomb goes off, or the escort’s bomb goes off, the other one is probably going to say to themselves – what the fcuk just happened!

What traps are being set for destruction?

Is the connection too intimate or not intimate enough? Did something get said that triggered an old wound? Is the level of ‘neediness’ building a feeling of care or pity? Is the conversation connecting, repelling or too invasive? Is the physical side clumsy or cute, rough or effeminate? Are the areas being focused on erogenous or irritating? Are the aromas a turn-off or turn-on? There are just so many approaches, things, beliefs and behaviours that can build a connection or destroy it. In this fast race to intimacy, the number of traps left hidden, ready to destroy any building interpersonal connection are huge.

When a deal-breaker happens?

Whether it is one critical ‘deal-breaker’, or the build up of lots of small negatives, when either the Escort or the client decides ‘the bomb has gone off’, they are unlikely to tell the other person due to the ‘transactional’ and ‘momentary’ nature of client-escort connections. They are just going to decide that this booking is the last booking (unless it is a ‘red card’ walk-out-on-the-booking offence).

In many of these cases, the other person, client or escort, is unlikely to know any of the detail of what happened. Why, when a connection was being made (in their view) did the other person pull the pin? This is unfortunately very likely to happen in client-escort connections, because in the rapid race to intimacy, the speed of advancement skips a lot of these discussions and discoveries.

Once again, I don’t have any answers, I just want to get people thinking. If anything, my only suggestion is to be aware that this is a common thing, and also maybe consider sharing any feedback with someone you are feeling close to, or think may be feeling close to you. Rejection is hard, but unclear rejection can be worse.

Since the first version of this article, I have seen polls showing that honest criticism between clients and escorts is rare. This isn’t surprising, no one wants to hear that their ‘best representation’ in a booking has shortcomings. Often the client or escort just moves on, or more accurately away.

If your connection is something that you want to maintain, deciding if issues are worth exposing and attempting to resolve, is a hard decision. I have tried now, mentioning some issues that have arisen, on a couple of occasions. I feel bad mentioning anything, I am not sure I am entitled to do so, and I am fearful of the risks. The result is often complex, feeling like a step forward and backward at the same time. The reality of two people resolving an issue seems to diminish the fantasy of perfect escort-client relations. I still can’t say what the better approach is – honesty or fantasy?

Thank you for your readership. Your comments and feedback is greatly appreciated as is any promotion of my articles.

Xx SP 10 April 2017 (article updated 21 May 2017).