A fantasy shared with John
Whilst I can't say that I share any fantasies about my immediate family, one fantasy of John's is a particular favourite of mine-namely having my partner jack me off in front of her friend, even moreso if that friend spontaneously ends up participating herself!
Whilst I can say that I have had the pleasure of such an indulgence (and I can't get enough of it) sadly my experiences are more near-misses than not!
That first time my fantasy was realised is etched in my mind forever. I had an amicable break-up with my girlfriend, C, and we were still living together a few months later. One evening she had her friend K, staying over the night and they had talked me into giving them both an innocent back massage before we retired for the night. When I had finished them both I whispered to my ex that if she was ever feeling in a charitable mood and wanted to return the favour, then I was always up for a 'massage' myself-knowing full well that she knew what I meant!
Much to my shock but absolute delight she responded by reaching down to the growing bulge in my pants and started to rub my cock in plain view of her friend K! K wasn't quite sure whether or not she was expected to leave the room, but my ex reassured her that she was more than welcome to observe. Moments later C had pulled my boxers down around my ankles and carried on wanking me. K, still a little taken-aback, then asked me if I was comfortable with her being there. Of course I reassured her, and it wasn't long before she had moved next to me and was tentatively rubbing my thigh as C worked my hard cock. A minute or so later I turned to K and asked her if I could play with her tits-she immediately pulled her top over her head and tossed it aside, and resumed rubbing my thigh.
Here I was, getting a handjob from my ex whilst her best friend-someone I had fantasised about in the past-sat topless beside me. And let me tell you, she had *fantastic* tits! It wasn't long before things progressed way past what can be described in this forum-but I will never forget that particular moment!
Whilst that was only the first of several encounters with C & K over the ensuing months, there have been a few missed opportunities that have left me kicking myself for years! Mind you, the fact that these particular opportunities were very real, involving real people I know, make them doubling exciting fantasies and I will continue to masturbate thinking about them for years to come.
My next girlfriend, another C, afforded me a few opportunities over the ensuing years, none of which quite panned out.
I had been with C for only a few months when the subject of any um, out-of-the-ordinary sexual experiences came up. I confessed the earlier experiences with C & K. She was quite surprised, and told me that only a week beforehand, things almost got very interesting for us. I asked her to elaborate...
On the previous Saturday, we had spent the afternoon with her best friend S and her boyfriend at the time. I had only met her a few times and didn't know her very well, but she was quite attractive and combined with the fact that she was my partner's best friend-I had already fantasised about her. Anyway, that evening we bought takeaway and took it all back to S's place. We sat around the loungeroom all evening eating and talking but I couldn't recall anything special about the night.
Now according to S, her boyfriend had been nagging her about one of his fantasies-to have sex with her whilst another couple watched or, even better, had sex right next to them. She had talked to C about this before Saturday night, but had made no promises. C then told me that at one stage during the Saturday night, S dragged her into the kitchen and asked her if she was willing to go ahead with it. They had planned on coming out of the kitchen and first start kissing us and then start rubbing our cocks. They figured that once we saw what was going on, we'd 'get into it'.
Unfortunately for me, C ended up chickening out-only because she didn't know what my opinions were on matters like this, and didn't want to jepoardise the relationship so early on in the piece! She assured me that had she known what she knew about me now, on the night she would definitely have agreed to it!
Just my luck, S ended that relationship soon after and that particular opportunity was lost forever!
At one point later in the relationship, I had convinced C to try going topless at the beach. She absolutely loved it, really got off on other guys seeing her (DD) tits, and couldn't wait to tell S what she'd done! That night I half-listened to her on the phone to S, telling her about going topless. S sounded quite interested, asking her how it felt and saying that she had thought about doing it in the past but never got the nerve up to go though with it. What she asked next gave me an instant hard-on-could she join us next time we were going to the beach, and would *I* mind if she went topless too! (I have absolutely no doubt she was serious but also teasing me). I actually jacked off then and there thinking about it while C continued her conversation two feet away to S!
Of course, that was by no means the last time I jacked off thinking about it either!
But, that just never happened, because a few weeks later I got a call one Fri/Sat evening from C asking if I could drive half-way across the city and pick up herself and S from the pub. I reluctantly agreed, only to find when I arrived that S was nowhere near ready to leave. She was single and obviously horny. I hadn't eaten so I grabbed a meal from the bistro and kept the girls topped-up with champagne and wine. After a few hours of good conversation we headed back to my car.
On the way back it was jokingly suggested we go for a skinny-dip. We actually made it into the water but didn't get naked, so there's not much to write about there. However, I forbade anyone to get into my (relatively new) car in soaking wet clothes. C had some spare T-shirts so S wrapped a towel around her bottom half and removed her skirt (I didn't see what, if anything, she wore beneath that) and then replaced her top with a dry shirt-removing her wet bra in the process. After removing it, she tossed it at me (she made me stand on the other side of the car at this point) and it landed on my head! I didn't expect it and, quite stupidly, simply removed it and tossed it back! How I wish I had that moment over again!
Back at S's place, rather than simply crash S decided to put on some music and start dancing in front of us-still wearing a towel, T-shirt and, quite possibly, nothing else! When C joined in I urged S to put on the final track of 'The Full Monty'. I was quite surprised when she did and then both of the girls gyrated to the striptease theme in front of me! After a minute or so, C started undoing her top-and it wasn't long before she ripped it open to reveal her tits! I had never seen her in any state of undress in front of any of her friends! They continued to dance and S positioned herself directly behind C (so I couldn't see her) and then 'flashed'-opening and closing her towel. I sat there mouth agape on the couch with a very obvious bulge in my jeans!
C tried to get me up to dance with them, but I was only interested in sitting on the couch and watching S-hoping she would go further. This continued for perhaps 10 minutes, with C in various stages of undress (she even removed her panties at one stage) and S flashing behind her. Eventually it fizzled out as C at last started to feel the effects of the late hour.
When I realised that things weren't going much further, I tried to coax C back into action but she had well and truly tired out and didn't want to know about it. We made our way to the door with S still rather chirpy and, in hindsight, I suspect rather horny.
Things quickly deteriorated between C & S after that day-nothing at all to do with the night before-and to my utter dismay they severed all ties not long after that! I couldn't believe it!
Talking later about 'that night' C told me that she had tried to get me up to dance only so she could take off my jeans and start jacking me off in front of S!!! When I asked her how far she was willing to let things go that night, she said that she had no problem with whatever happened between S & I, as long as she was there to watch.
My final missed opportunity involves C again, this time with a different girl S. It was after C and I had (amicably) ended our relationship. S was a mutual friend, has the face of an angel, and this time I had done more than fantasised about her-I had asked her out. She said she was flattered, but declined the offer. None-the-less, we remained friends, although C & S became a lot closer as girls do. There were no secrets between them, and as it came to pass, no secrets between S & I. In fact, S had eventually read a few 'stories' I had written about her and another mutual friend so she knew-to the very last detail-how I fantasised about her.
One of those fantasies was watching her in the shower in the (deserted) gym one night after class. After reading that she joked (half-seriously) to C that it might just happen. Sadly, it never did.
Another fantasy that was originally actually C's that I had adopted was having her give me a handjob in an all-but-deserted cinema whilst her friend A (also known to S) watched! C told me about her fantasy with A one night and I absolutely loved it!!! She was telling A that I had been begging her to arrange it but, no surprise to me, A wasn't really interested. S then got wind of the conversation and told C that she'd *love* to watch if C went ahead with it! Of course this sent me over the edge (on many occasions) and I did my best to convince C to arrange it.
Of course, this was thwarted again when S began a relationship soon after. Eventually C went as far as asking S if she'd like to join us at the cinema one Sunday night but S declined, saying she didn't feel comfortable even though it was very early days with her new boyfriend.
There have been a few other more successful occasions since (even recently) but as far as 'jacking material' goes, nothing compares to thinking about these missed opportunities and wondering what could've been! Perhaps in some cases it's even a blessing in disguise-I've often heard that when fantasies finally do come true, they don't live up to expectations. So I guess I do have these fantasies to keep me going, with no real prospect of them ever coming true.
I'd love to hear of anyone else's 'near-misses'-in detail of course!