In early 2023, I posted the tale of how my wife's friend seduced me with her deliciously-cooked Shepherd's Pie (not to mention her voluptuous body) while my wife was away on a European City Break with another friend. You may care to read that story (posted under “My wife likes short city breaks) to get the context of the situation.
At the time of writing, I was vaguely hoping this was the start of something totally new for me but, as the weeks went by and nothing more was said, I concluded it was just a silly wager between 2 mature ladies and nothing more would occur. I was, of course, aware that Di and Jill continued to attend weekly keep fit classes together and they would meet for a coffee fairly regularly.
We had already booked a week away in Crete during the September of that year, just Di and me, to catch some warm weather before the really cold weather arrived in the UK. Di came home from one of her keep fit classes during the summer and asked if I would mind if Jill joined us for that holiday. They had already spent some time away together for short breaks and Jill's adult children were pleased that, having been widowed for more than a decade, she had found a friend that she could enjoy holidays with. Needless to say, I said I had no objection, and Di announced they had already established there was a single room available at the same hotel and Jill would rush down to the same travel agents we use to book it. In reality, I suspect Jill had already made the booking and Di knew she would have no trouble persuading me to say yes.
Di was unwilling to share with me what the ladies had discussed, and I didn't think she would be prepared to share me in a threesome, much less watch me with another woman, even a close friend such as Jill. I thought my previous assignation with Jill happened because of the ladies' wager, which Di was slightly miffed that she lost, and there would be no chance of me being called upon to perform again.
So, third week in September, we flew out to Crete to enjoy our usual autumn break, accompanied by Jill this time. As always, Di's choice of hotel was impeccable – lovely setting, close to the beach and lots of tavernas nearby where we could eat. Unbeknown to me, Di had emailed the hotel as soon as she knew Jill was coming with us to ask whether we could be allocated adjacent rooms, so she was right next door to us.
On the first evening, we went for our evening meal at a local taverna and, as we walked back to the hotel, Di said to me that she didn't think she was quite ready to see me with another woman yet. I glanced over at Jill to see her smiling and raising her eyebrows. When we arrived at our room doors, Di said “off you pop then” and Jill murmured quietly. So it was that I found myself following Jill into her hotel room.
As soon as I closed the door behind us, Jill turned to me and said she had been looking forward to this so much and we were soon locked in a passionate embrace. She said she wanted to take the dominant role this time and was quickly pulling at my belt buckle as she knelt before me. I thought well Di has never done this to me before, so I decided to just stand there and enjoy the experience. Having slid my trousers and boxers down to my knees, she licked her lips and looked up into my face with a broad smile, before engulfing my cock in her soft mouth.
I combed my fingers through her hair and murmured to let her know she had hit the spot, and she seemed willing to carry on like that all night, but I wanted to get her naked, and explore her with my tongue too. I suggested that we should get naked and she readily stood up so I could unzip the back of her dress, and she willingly allowed the dress to fall off her arms. It was only then that I realised she had no knickers on, so I pushed Jill backwards onto the bed, standing to admire her curves while I discarded my clothes.
Jill willingly opened her legs so I could explore her pussy, which tasted just as sweet as I remembered it from more than a year ago. Having got her on her back with her legs spread wide, I slowly slid two fingers into her very wet pussy and sucked her clit between my lips, causing her to orgasm noisily. When I crawled up to kiss her again, she grabbed hold of my cock with one hand to guide me inside her very wet pussy, demanding that I cum inside her, as she orgasmed repeatedly,
I would like to say that I continued to fuck her for ages but, in reality I came fairly quickly, flooding her pussy with my seed. We continued to maul each other passionately though, before I eventually rolled off, gasping for breath. We lay there for some time, me gently stroking her nipples and kissing her lips as she sighed blissfully.
After a while, Jill said that , if we laid there for too long, she would start leaking on the bed. Knowing how much my wife likes another gentle orgasm, I rolled her over onto her back, positioning myself between her thighs, and began sliding my tongue into her pussy so I could collect her 'leakages'. It wasn't too long before she was orgasming again, thrusting her pussy against my face, gasping “oh yes – oh yes – oh fuck”.
After Jill had calmed down, we crawled under the covers, and we cuddled together and Jill licked my face clean of our combined juices that had leaked from her pussy. We then drifted off to sleep for several hours in each others arms. I was awoken in the early hours of the morning by Jill sucking my cock trying to coax me back to life. She said it was nearly 6 am and she was hoping I could manage another erection before I had to return next door.
I certainly managed the erection, and we fucked again, although I knew flooding her pussy again was probably unlikely, as my orgasm lasted barely a minute. This did not seem to make any difference to Jill as she gasped and groaned her way through several very enjoyable orgasms. I then dressed and returned to my wife, who woke as I slid into bed beside her. She said she assumed I would not be capable of servicing her just yet, so perhaps I should catch up on some sleep.
And so the holiday continued, me going next door to see to Jill's needs every couple of nights although, in reality, it was more a case of her gorging her desires, her favourite position was sitting on my face so I could thrust my tongue into her open pussy. Having been without sex since her husband died about 10 years ago, she had truly rediscovered her desires.
On the last night, Jill came into our room, my wife said she thought she was now ready to see me with another woman. Initially, Di simply sat in the chair watching us we stripped each other and becoming intimate. I noticed when Jill had got me on my back and started to suck my cock that Di had her hand down the front of her panties stimulating herself. By the time Jill climbed aboard and impaled herself on my cock, Di had discarded her clothes and was knelt beside us, kissing Jill and mauling her tits. Jill certainly seemed to enjoy mauling my wife's ample tits.
The sight of Di and Jill enjoying each other's ample bodies was too much for me, and I came inside Jill with a roar, triggering her orgasm too. When she realised I had stopped cumming, Jill climbed off me and the ladies adopted a 69, Jill on top, so they could enjoy stimulate each other. Watching my wife licking Jill's pussy clean was certainly a new experience for me, which they both seemed to enjoy, as they gasped and groaned their way through their own enjoyment.
By the time Jill returned to her own room in the early hours, we were all well and truly fucked. And so it was that my wife came to accept that I had a role to play in satisfying her friend's needs every few weeks. The ladies still did their keep fit classes once a week, and met for coffee too. I suspect they were also meeting for other purposes when I was out playing golf, but I decided not to ask as I did not want to rock the boat, in what was clearly a beneficial situation for us all.
