I was enjoying flirting with the waiter in the poolside bar. Since my sexual adventure with my bosses in ( Going Dogging) I had been enjoying my new found sexuality and with a better toned body, a new sexy wardrobe and a spray on tan. I had been determined to fully enjoy the break that Tom had booked for us in Malta. And that included possible fun with young guys like this.
Since my "adventure" with my "bosses" Tom had been pushing me for a threesome and indeed when he booked this holiday we had discussed the possibility of making it happen. The thought obviously excited him and we had some very good sessions fantasising on the basis of what could happen. He appeared to want me to go to bed with him and one or two "young studs." So I promised him that I would wear revealing clothes and if the situation arose where he wanted something to happen then I would most probably be "up for it."
I had worn white when I went down to breakfast as I thought it would show off my tan. I also went braless because while it is good to have a bit of support sometimes when you are as big on top as I am, I know Tom loves me to show my breasts off in public.
I am sure Tom was disappointed when he saw that there were few young single guys at breakfast just a few younger couples and a lot of couples our age -- probably like us taking advantage of the supposed "golden years" of retirement.
Certainly, at breakfast, while some of the younger guys with their wives were fanciable, there were no young single guys in evidence and while I don't mind flirting with hotel staff it's not very good for one's reputation to go any further if you want to return on holiday again.
Anyway to make up for Tom's disappointment of there being no potential young studs I thought I would give him a treat by wearing my most risqué bathing costume -- this basically consisted a tiny scrap of white material that barely covered my pussy mound and some golden braided string . It certainly had a "wow" factor for Tom because when I put it on he very roughly dry mounted me from behind while he groped my boobs. I think he would have taken me there and then if I hadn't persuaded him to wait.
To tease and please him more I wore a quite transparent wrap. It certainly had the desired effect when I went down to the pool as I noticed quite a few admiring glances from the guys at the pool and some rather disapproving looks from the wives. At one time this would have worried me but since I bedded the two guys I am quite confident about the attractiveness of my body and my sexuality. Hey -- although my breasts droop a bit more than they did and like quite a few supermodels I have a bit of cellulite -- I know that guys still find the overall package quite attractive.
While I had been swimming Tom had ordered some drinks from the pool bar and I had noticed the very handsome early twenties waiter's eyes fully take in my nude boobs and my rather prominent pussy lips straining against the wet and now fairly transparent tiny piece of material as I re-arranged it.
He knew I had caught him checking me out and we shared a smile when he realised this. He also smiled and looked back when I said to Tom " He's rather nice" as he walked away.
Actually he really was quite attractive being slim, about six feet tall and slightly dark skinned and he obviously had quite liked what he saw!
About half an hour later when Tom went for a dip, I said I would go and order more drinks and a couple of sandwiches and I knew from Tom's reaction he thought I was going to flirt with the waiter as I only pulled on the transparent wrap over my g-string.
The waiter smiled when he saw me come in and as I find it quite a turn on now to see guys admiring my breasts and I rather carelessly let the wrap slip open and it was gratifying to see his eyes go to my breasts as I perused the menu. He said the sandwiches would be about 10 minutes and in spite of his dark skin I swear he blushed when I asked him was he making them specially for me. He recovered well to say "for you madam they will be very special!"
He obviously wanted to keep me in the bar because he said " would madam like a drink while she is waiting?"
I was just relaxing with my drink and thinking how much fun I could have with this guy when I heard some people come into the bar and I was stunned to hear someone say "Mrs W -- it is you isn't it?" I turned round and was rather stunned to see the questioner was one of three young guys, and none other than Chris, the son of our golf club ladies captain who is a good friend of mine. Chris had caddied for Tom and me for several years before he went to University.
To say I was stunned was actually an understatement because although I am now more confident about my sexuality and body, I tend to dress more conservatively at home and certainly felt embarrassed to have everything on display for a boy I have known since he was a kid!
I am afraid it was my turn to blush and try to seek as much cover as I could from the thin gauze of my wrap. For their part he and the other two guys wanted to chat and explained that they had taken a short break before their Summer Uni examinations and they were just returning from a party in Bugibba! He seemed particularly keen to know whether I was "with the girls" or Mr. Wilson.
The conversation was a bit stilted and I was quite relieved when our waiter brought the sandwiches. Chris insisted on carrying them and the drinks for Tom and I out to the pool and the three guys ushered me out in front of them. I have to say I felt really exposed to have the three young guys and especially one of my best friend's son, see my largely exposed buttocks which I felt would be fairly obvious through my wrap.
Tom To celebrate Eileen getting the distributorships she sought and to be frank to try to take advantage of her newfound sexuality ( see Going Dogging) I booked a short
break to Malta last Easter. We like Malta at this time of the year because while it can be pleasantly warm during the day it is quite cool at night and Eileen can wear the short skirts and stockings that I love.
Since Eileen had told me about bedding the two guys I couldn't get the thought of sharing her with some young stud out of my mind. We fantasised about it and I decided to try to make it a reality by getting her away from our home locality to make it to happen.
I decided to on a good quality hotel we had been to before near the north of the island. It has a sophisticated cocktail bar ( where skirts and stockings would not be out of place), and indoor and outdoor pools where I could get Eileen to show off her ripe assets. When we had been there a couple of years previously, although Eileen was a lot more modest than she is now, she had allowed me to persuade her to go topless at the pool and it had turned me on a bit to see younger guys ogling my wife's exposed mature breasts. After her experiences with her bosses I was really looking forward to having a real no limits sexual adventure with her on this break.
We were up quite late the first morning as it had been a late evening flight that had got us in. When we went down to breakfast Eileen looked cool and sexy, with her spray on tan being emphasised by her white outfit. This outfit consisted of a tight white tee shirt with no bra - that not only showed off her heavy mature 39" breasts but also her thick nipples and dark aureoles. With this she wore tight white stretch knee length trousers that showed off her ripe thighs framing a sexy prominent pussy mound and her two big jutting buttocks.
I was a little disappointed to see that apart from a couple of young couples most of the people at breakfast were couples of around our own age although it was still quite a turn on to see a lot of the guys ogling Eileen.
It was a glorious day and we decided to spend some time at the outdoor pool. My spirits perked up considerably when I saw the miniscule white thong that Eileen was intending to wear at the pool. The scrap of white material in front barely covered the large pussy lips and one could see the top of the little line of hair that she keeps above her shaven pussy. The back of the garment was a simple row of gold beads which were completely lost in the deep valley between her jutting buttocks. When she put it on my cock sprung to attention as I moved up behind her to grope the weight of the heavy breasts and if she hadn't suggested we leave it to later I would have had her there and then.
Once again she had quite a few glances of approval from the guys and disapproval from the wives when she arrived at the pool about 11.30 in just a fairly transparent wrap and the g string. A few of the younger women were topless but none in quite a daring costume as Eileen and most of the women of her age were in more "sensible" one piece costumes.
About midday Eileen decided to have a swim while I went in to the pool bar to order some drinks and the barman said he would bring them out. As I came back down to pool Eileen was just getting out of the pool and to my delight and the fairly obvious interest of most of the guys round the pool the tiny scrap of material was now not only almost totally transparent but had worked its way between her pussy lips and the lot was virtually on display.
What I thought was quite magnificent was that she was now so utterly confident in her own sexuality that she was totally unconcerned at the stir she had created. She was settling back into her lounger and was quite unselfconsciously adjusting the triangle of material over her pussy mound when the young waiter, in his mid twenties, came with our drinks. In fact she flashed a dazzling smile when she saw his eyes go first to her crotch and then to her breasts.
As he turned to go away she rather loudly and deliberately said -- "he's rather nice, I could quite fancy him."
She really did mean it because when I went for a dip she came over to the pool and said that she was going in to get more drinks and a sandwich. As she put on her wrap and went in to the bar, I noticed that there were quite a few guys eyes going to her big bouncing buttocks and their jewelled divider quite clearly visible through the transparent material of the wrap.
I was just coming out of the pool when I saw Eileen and the three guys come out of the bar. I too was stunned to see one of them was Chris, a guy we have known since he was kid, and in a place where we thought we could relax without anyone knowing us.
When we all sat down the conversation was a little awkward but we found that the guys were in the last three days of a 10 day break before going back to Uni to sit exams. I expressed surprise at them staying in a resort other than the livelier Bugibba but they said they hadn't been to Malta before and had chosen this hotel due to it having a tennis court and its proximity to the golf course. When I asked them were they not a bit bored -- they said they were a bit during the day but they went into Bugibba at night. One guy, John, suggested we might like to go with them that night but we declined saying we were still a bit tired from the travelling. I did take Chris up on a game of tennis later that day and the guys on a game of golf the next day.
The guys excused themselves to go and get something to eat and Eileen said she was mortified through seeing Chris. I told her not to worry as she looked absolutely gorgeous and there wasn't much wrong with going topless on holiday.
Somewhat reassured by this and possibly by a couple of G&Ts she was happy to drop the wrap and sunbathe in just the g-string even when Chris came to collect me for our game of tennis.
I had been a little embarrassed when Chris and his friends had "caught" me wearing very little indeed however a few G&Ts later and Tom's reassurance allowed me to relax and enjoy my sun bathing. When Chris came to collect Tom for the game of tennis I was quite relaxed and even a little amused to see him check out my breasts and crotch.
I had settled back into my book when I was rather startled by Chris's mates John and Peter, flopping down beside me, with John asking did I fancy a dip. I declined and said maybe later but couldn't help admiring their hard young bodies as they dived into the pool. When they came out they offered a drink. A further couple of G&T's later I relaxed enough in their company to allow myself to be persuaded to join them in the pool. Initially they were quite reserved but when I bumped into one as I turned at the bottom of the pool a little "horseplay" developed and the ice was broken. And I realised that both guys were happy to take the opportunity to "cop a quick feel" of my breasts and rear as part of their play.
I felt it was getting slightly out of hand when they sandwiched me and I felt Peter's erection against my crotch and John's against my rear. I excused myself and turned to leave the pool. Things continued to get sexually charged because as I climbed out I felt John help me out by placing his hands on my virtually nude buttocks and when the guys joined me in the fresh water shower it was difficult not to see their large erections in the wet clinging shorts.
Peter saw me looking at his and smiled "sorry about this but we really do find you very attractive."
I said " Don't be silly I really am old enough to be your mother."
John smiled and said "We love older women and especially beautiful women. You are the best looking woman by far in this hotel."
When I asked him what Chris would think of his two friends trying it on with his mother's friend they smiled and said Chris had had the hots for me for many years.
I led them back to the loungers and to ease the sexual tension I suggested to Peter that I would love a large G&T. As he went to get drinks I dried off and took up John's offer to do my back with sun cream.
I turned over on to my tummy and have to say and whether it was the G&Ts or the fact that I knew these two hard bodied young guys in their late teens wanted me, I got quite turned on when he very gently started to rub the cream from my neck down my back and on to sides of my breasts. I was quite intrigued to see what he would do when he reached my waist but before he did so Peter came back and said " Can I help?"
I was about to say "no that's fine" when I felt another pair of hands join the massage as Peter had obviously decide to massage my rear. I decided to cut the massage short when I felt the cool drizzle of cream in the crack of my rear and I thought Peter's fingers might follow.
As I turned to say to him, that I could do my own rear and thighs. I was almost literally face to face with what looked like a massive erection. and he asked if I would like him to put some cream on my front! Although I was quite turned on, I wasn't drunk enough or turned on enough not to realise what it must look like to the other guests to see two young guys massaging a much more mature lady. I rather tongue in cheek said to the guys "Mmmmm that might be fun but -- if you want to put some on my front you had better do it up on our balcony."
John muttered "What are we waiting for!"
I replied " Ok guys lets go up to our room for a drink because we are creating a bit of a scene here - but a drink only."
As we went up in the lift John bent down and kissed me and as I responded I felt Peter take the weight of one of my breasts in his hand. I hadn't really time to think where what had started out as a harmless bit of flirting was going. By the time the lift had stopped the guys hands were everywhere and when the door opened a rather elderly couple looked disapprovingly on as I rather tumbled out of the lift in a clinch with the two guys.
This sort of brought me to my senses and I managed to get them to stop groping me long enough to open the door to our room but as I did my wrap was pulled off and I was immediately sandwiched between them. Once again their hands were everywhere and I have to admit that the thought of two very handsome young guys so obviously desiring my body really turned me on. Only the thought of Tom coming back and finding me in bed with the two of them prevented me from responding. I broke away and said " Hey guys, lets cool it and have a drink, Tom could be back any time. After all I only agreed to you putting some sun cream on me not grope the hell out of me or worse!"
To be fair to them, in spite of their very obvious arousal, this time they did take me seriously and allowed me to go to the fridge to get a bottle of wine. As I poured them a glass John once again bent down and kissed me and said "Sorry we got so heavy Eileen, but you really do turn us on."
I broke free and took my drink out on to the balcony and to my amusement Peter followed me out with the tube of cream. " Ok, Eileen have it your way for today but at least keep your promise to let me put cream your front."
I turned and pushed my chest out and said "Ok, but be quick because I don't want Tom to come back and see you fondling my boobs!"
It was quite erotic to be kissed and cuddled by the two young guys as they massaged the cream into my breasts and rapidly thickening nipples and I suppose I did respond. Before I knew what was happening cream covered fingers had pushed my bikini bottom aside and had entered my pussy. As I tried to push that hand away, fingers similarly pushed the string aside and probed for my anus. In spite of my protestations I was soon being finger fucked in both orifices and only the fear of Tom walking in us prevented me from enjoying it.
In fact John whispered in my ear "Listen Eileen both you and we know you've been gagging for so don't play the cock tease now." I was literally saved by the bell when my mobile rang and it was Tom to see where I was and did I wish to join Chris and he, in the bar for a drink. This time the guys did take "no" for an answer and I shooed them out of the room with a promise to see them the next day.
Tom I enjoyed my game of tennis with Chris -- although he is much younger and much fitter I still keep in shape and at my prime would have been a better player. After a couple of hard fought sets which we shared he suggested a welcome beer.
As we were chatting I called Eileen to see if she wanted to join us and this stimulated Chris to say -- "Mrs W is looking absolutely fantastic." When I told him she was a little embarrassed at his mates and him seeing her wearing so little.
He smiled and said "We certainly didn't mind!"
When I asked him did he and his mates find her attractive he said "very," and he admitted that he and most of the caddies had had a thing about her for years!
I noticed him checking her out when she arrived down in a white tee shirt and short white skirt and he readily accepted my invitation to dinner with us that night "if he didn't mind giving up a much wilder night in Bugibba."
When we went up Eileen appraised me of the fact that my call had been fortuitous as the two guys had just got quite heavy with her. When I asked would she have gone further my cock rose when she said - probably if they hadn't been mates of Chris's. When I asked her "what about Chris?" she smiled and said that she had never thought of him like that and hadn't really realised he was so good looking.
She smiled when I said that Chris had been talking about how attractive he found her all afternoon and she said the other guys had told her that he had "had the hots" for her for quite a few years. When I asked her was she up for it with him she grinned and said "Its up to you."
When I heard this I could hardly stop myself from jumping her there and then but satisfied myself by suggesting if anything was going to happen it would have to be that night as the next night was the guys last one.
That night when I saw what she was wearing for dinner I realised that while she was up for it she was playing it safe in case wasn't interested. She was dressed "smart sexy in a while low cut tee short that showed her cleavage off if she leaned forward and through which one could clearly see the nipples and outline of her unbraed breasts. She had teamed this up with a short black skirt, stockings and suspenders.