Written by Shirley

19 Apr 2012

Well, that evening the three of us had a meal together in another restaurant Don and I liked, then it was back to the villa. As before, except that Don and I changed into something 'more comfortable', as they say. Don into just a pair of shorts, old football ones and well worn with nothing underneath, so that his bits are well outlined, I like that when we're home. Me? Just in a very thin shift dress, just right for these occasions, also with nothing underneath of course. I persuaded Jack to strip to his briefs, talk about embarrassed, he was as red as a beetroot. It became obvious why, in his swim shorts his package was rather obscured, now he couldn't hide the fact that his cock alone was held sideways because it was so large it would have come out one way or another!

We had drinks, again after a drink and a bottle of wine with our meal and Jack was surely not used to drinking any great amount. Not that he was drunk but more lively. Anyway Don said, 'I gather Shirley's going to teach you what it's all about, Jack?' He coloured up again but sort of giggled, 'Yeah!', he admitted. 'You couldn't have a better teacher,' Don told him, 'don't mind me, I'm just a bit of the furniture, once you're sorted we'll all have fun together.'

Jack and I were once more sitting together on the sort of garden sofa we had on the sundeck, I turned and kissed him. It was obvious that he wasn't used to a really passionate kiss, I said, 'Come on, Jack, let yourself go. Look these are already for you!' And I bared my breasts, 'Do you like them?' Jack's eyes were like doorstops, I put an arm round his shoulders and pulled him down and round so that his face was buried in my breasts. 'I like them kissed and my nipples sucked, Jack.' He sort of gasped and began kissing them, 'That's a good boy,' I held a breast, 'now suck this,' and I offered him a nipple. He was good, he could suck for England I thought as I transferred him to the other one. My nipples erected instantly and my fanny began to engorge. I felt for his cock, it was erect and very hard, I pulled his briefs aside and started caressing it.

I was enjoying the attention I was getting and I said, 'Take my dress off.' He sat up, I lifted my bottom, and he pulled the dress over my head letting him see my mound and the little bit of my slit that was visible. He gasped, 'Never seen a fanny, darling? Look at mine!' I lounged back and spread my legs, my lips were already parting as the inner lips engorged and erected, 'There.' I took his hand and placed it over my mound and the open lips. Then I pressed his middle finger into the soft flesh, 'Just do what comes naturally,' I told him. He was much gentler than I thought he'd be considering that he'd never even seen a cunt, let alone played with one. 'Push your finger in.' He obeyed. By now I was getting really wet, Don could tell you how wet I get once I'm aroused. Jack's gentle probing and caressing was excellent and I was soon thoroughly aroused and wanting a good fucking and I hadn't yet taught him what a clit was!

I took his hand again and gently pulled it out of my cunt before placing the finger on my erect clit, 'This bit, Jack.... can you feel it? It's sort of like a piece of gristle, it's called a clitoris, clit for short, and it is the one organ of the human body that is there purely for the pleasure of the woman. Every girl has one, get to touch that and it's almost guaranteed that she'll let you do anything.' I showed him how best to caress it and just lay back and let him get on with it. We were kissing passionately every now and again and I was really up for it.

I moved to look at his cock, it must have been over eight inches and as thick as a big cucumber, my heart jumped at the thought of it thrusting up me. The knob was huge, the purple skin stretched so tight it looked as if it would burst and it was already slick with his juice. I could smell the musky, spunky, scent of it. I moved us around so that I could kiss it, he continued playing with my cunt, now pouring juice. So I lowered my head and took the knob in my mouth. Jack gasped, 'Oh God!' I sucked and went down on him as far as I could, which wasn't long as it was so thick.

Jack was groaning and clearly becoming more aroused than he'd ever been, so I thought the time had come. I eased Jack off, 'Come on darling,' I pulled him over to the big double sunbed and lay on it with my legs wide open, 'Fuck me,' I ordered. His cock was swaying from side to side and up and down as he moved, I loved it. 'Gently now,' I told him, 'I've never had a cock as big as yours in my cunt!' He covered me and I took that beautiful thing in hand and rubbed it the mouth of my cunt, all round and hard on my clit, then I put it in the right place, 'Now!' I said. Jack began pushing gently, he couldn't get it in at first, 'It's alright, darling, just keep pushing gently and you'll stretch me until it goes in.' A couple of minutes later it was sliding into my tight cunt, I couldn't believe how much it stretched me and was glad that I was so wet.

Now came the ultimate of my fantasies that I'd ever thought would come true as Jack eased his massive cock up me. I wondered whether it would all go in, but it did and his balls were trapped against my bottom, 'Now fuck!' I told him. Somehow I knew that he'd take it gently at first and he did, my senses swam, it rubbed my clit all the time, going in or sliding back. As Jack got used to it he panted, 'You're so hot inside, like a furnace!', then he began to speed up. I came almost instantly, my thrashing around and moaning must have frightened him for he stopped. 'It's alright, boy,' Don said, 'you've made her cum, that's all.' 'Oh,' Jack said and started fucking me again.

I soon began to want him to be more vigorous and urged him on, but I had forgotten that he'd never fucked before and he suddenly came. He groaned, rammed his cock in, then spurted heavily as he drew back, he did it several times. I cried out, I thought that Don and the stripper, Paul, spunked hard, but they had nothing on this boy as he fired his spunk into me like cannon shots, filling me instantly with hot spunk. I came, I came so intensely that I fainted, or something, it frightened Jack until I came-to a second or so later, I told him that it was alright. Then he flopped on me.

I realised that he'd seemed to last sometime but in fact it was only about two minutes tops. When we had recovered I asked him how he felt, 'Oh God, I never realised it would be like that!' he said. I felt his cock softening and he started to take it out but I stopped him, 'Leave it in, darling, I'll get it hard again for you in a minute, then you can take your time and give me a lot more pleasure!' 'Oh!' he panted and flopped on me again.

I looked across at Don, he gave me the thumbs-up. I grinned, I felt good, I had no idea that I would be so well 'pleasured', being fucked by a virgin who had only lasted such a short time. I was eager to have another go, so only about five minutes later I started squeezing his cock rhythmically with my internal muscles. I was was well practiced at this having done it virtually all my life, so it wasn't long before I felt his cock begin to grow again. As soon as Jack felt himself hard enough, he started fucking me again. This time I persuaded him to take a rest as soon as he felt the sap rising and advised him that he could do this as often as he liked and he'd enjoy a really good, long, fucking. Women know, only too well, that most men can't last more than about two minutes and that they remain unsatisfied, very frustrating and the reason why I try to train all my lovers how to last. This time Jack lasted about five minutes, which I thought a good start. I reckoned by the end of the holiday that I would have him trained to last for at least fifteen.

Once again, a thrilling ejaculation and a much more satisfying fucking as I had cum several times, how could I not when his giant cock rubbed my clit all the time? Eventually Jack rolled off and a very aroused Don took his place to give me a long, very messy, fuck. All that spunk has to go somewhere! Later Jack was able to fuck me again and Don also, of course. Great evening for me, including the satisfaction of introducing a virgin to the joys of sex!

Jack didn't go back to his hotel that night but slept in our spare room. He didn't wake but Don had me again from behind sometime in the night, which I enjoyed. This sort of scenario continued all the holiday, I introduced Jack to the joys of oral sex and to several different positions and ways of playing around. With two men to use me I had a thoroughly enjoyable sexual holiday and went on to do it again quite a few times, a woman can always take more sex than one man, so it is an ideal arrangement.

So that was it then, nearly all my fantasies catered for, with Don enjoying seeing me with another woman and fucking several other men, to his great pleasure. The only one that has not happened so far is, as Don pointed out, me being gang-banged. Will it ever happen? Who knows, I'm still keen, but this really does involved a really special set of circumsances so I don't know. Just keep looking, maybe some month or year in the future you will read of me happily fulfilling the last of my fantasies!