continued...

My experience with cumslut 'S' convinced me that mature ladies were dirty ladies (I have not been proved wrong yet!). On one occasion she asked if 'M' and I would double penetrate her cunt, something she had never experienced before. 'M' laid on the bed face up and 'S' climbed on top in the cowgirl position. Once 'M's cock was inside her, I approached from behind and eased my cock in above his. 'M' had a shorter cock than me, but it had a wider girth, so by the time I was fully inside, 'S's cunt was quite widely stretched. It took a while to figure out a workable rhythm, with 'M's shorter cock falling out a couple of times, but we soon found a good pace. The feeling of such a tight cunt, and another man's cock rubbing against mine was a new, and not entirely unpleasant experience. With some negotiation 'M' and I managed to cum within a few strokes of each other, filling 'S's cunt to the brim with our sperm.

This meeting had ticked a box on my mental bucket list, and I resolved to try as many new experiences as I could in future.

Sometimes meeting other swingers involved negotiating desires, boundaries and limits during play. I considered that visiting someone who had specified all these things clearly before arrival would remove the clumsiness, so I decided it was time that I took advantage of some of the 'professional' ladies who advertised their services on the internet. I have no problem with prostitution, but refuse to be involved with anyone who may have been the victim of trafficking. For this reason I found an independent mature lady who was offering a good range of services including anal and cum in mouth (cim). She also had the initial 'S' (as will the next two ladies I refer to - many sexy ladies have names starting with S!).

I booked an hour visit, and after the financial preliminaries we got down to business. 'S' started with a nice massage to put me at ease, followed by a soft blowjob and then penetration. I was told I could cum as many times as I wished in the allotted time, so after twenty minutes or so I blew my load into face. I felt this would allow me time to recover before the main event.

After a few minutes I began to finger 'S's cunt, and then licking her cunt out while fingering her arse. This always has the desired effect and I was soon semi-hard; good enough to go again. 'S' took my full length in her arse easily, and after a while I was fully hard and enjoying the ride. Every now and then I stopped fucking for some more cunt licking so I would last longer, but eventually I started to pump hard and finished in her arse powerfully. 'S' was surprised at how full the condom was, but I had been going without for a few weeks and my balls were full to bursting! A very enjoyable first time.

Shortly after this meeting I was working in Eastbourne and felt the urge rising again. After work I contacted a brothel I had been told about and asked who was working that evening. I was informed that a lady, another 'S' was available, and I agreed a half hour visit. When I arrived I was pleasantly surprised to see a very attractive lady in stockings and a basque waiting for me. She looked very similar to Cat Deely, a well known British television presenter. Half an hour does not leave a lot of time for creativity, so a quick blowjob and cunt licking was followed by some sensual fucking to completion.

I decided that going to a professional lady would be an ideal way to relieve my aching balls when no other opportunities were available, and to tick off even more items on my bucket list. Although I was still married to 'A' at this time, we did not find time for much bedroom fun, and as my sex drive was much higher, I was often sexually frustrated.

Later that same month I was contacted by a couple on a swinging site. The husband 'D' said he had a very submissive wife 'S', and he'd like to arrange for a man to come and seduce her while he was out walking the dog, and then catch them together when he got home. I arrived at the house early evening and was briefly welcomed by 'D' before he left the house. I got chatting to 'S' who was very pleasant and welcoming; she offered me a drink then we settled down on the settee.

I had worked out a scenario where I would order her to take up a submissive position, and then tell her my rules, and what to expect in the way of punishment for misbehaviour. Before I could put my plan to action, I heard the front door opening.

'D' must have run around the block because he was home before I'd even got started on the seduction. Nevertheless, I started to brush my hand on 'S's leg when 'D' went to the kitchen to get himself a drink. Almost immediately 'S' changed. She became completely trance like. Gone was the chatty, fun woman I had first met. 'S' stared blankly while I fondled and groped her. After a few minutes 'D' suggested we move to the bedroom and guided his zombie like wife upstairs. All through the foreplay, oral, and even when I started fucking her arse, 'S' remained completely detached from reality. I had never experienced anything like it before. 'D and I took turns fucking his unresponsive wife before finally cumming on her chest and face. 

I drove home wondering what had just happened. Later that week I was invited back, and once again was greeted by the happy-go-lucky lady, but as soon as I touched her she went into her trance again. The whole thing was a bit weird and this time I made my excuses and left after a short period of foreplay. I had to wank myself off whilst driving home to get some relief.

After the very strange encounter with 'S' and 'D', I had six months without any swinging action arranged. I decided it was time for another sex worker visit and that I would like to try age play. It had been many years since I had fucked my first girlfriend who was seventeen at the time, and I wondered what a young body would feel like now. By this time I was well into middle age and so selected someone listed as young and playful who enjoyed the company of much older men. When I arrived it was clear that 'J' was still a teenager herself. She had a daddy complex which wasn't what I expected, and said that she was nearly nineteen and had been working only four months. Her lack of experience as a prostitute didn't quell her enthusiasm, and she seemed to really enjoy playing out the role as a naughty little girl. After this I had two nice but unremarkable visits to other young prostitutes, both in their twenties. As a middle aged man, the attention of three such young women was a big turn on visually, but the sex itself wasn't anything special. It was not long before I was back searching the swinging websites again.

Eventually I hooked up with another man 'B' who's girlfriend 'G' liked to be tied to the bed and fucked. We arranged that I would arrive quietly and creep upstairs to join them with 'G' tied up and blindfolded ready. 'G' had no idea I was coming, and jumped with surprise when a second pair of hands started fondling her. 'B' and I had agreed that no words were to be spoken and I would leave at the end with 'G' completely unaware who I was. For most of the evening 'B' sat on the bed and watched me fucking his girlfriend. At one point he signalled to me that her arse was available and when I started to finger it she started begging "please fuck my arse!" over and over. I didn't need asking twice. Eventually, after a couple of hours of action, I sprayed her face and blindfold with my cum before creeping back out, leaving the two of them alone together again. Another bucket list tick!

After another eight months of inactivity I needed another release, so I found a prostitute called 'T' who offered anal and rimming. I had to try that, so I arranged an hour with her. The feeling of a lady having her tongue up my arse was amazing! I spent a happy hour being treated to oral, anal and fucking, interspersed with sessions of arse licking which kept me hard as diamonds.

I promised myself that in future, if there was no other opportunities pending, I would continue to seek professional services to broaden my experience, tick off more items on my bucket list, and release my pent up lust.

To be continued...