While waiting for Ben's turn in 'A 3-Part Fantasy,' here is Ben's version of News Lady's fantasy.
Leave your Jag at the dock, News Lady. My version occurs on a boat far from shore, in quiet seas on a beautiful summer day. We are free to indulge our fantasies and be completely naked in the warm sunlight on deck or in the cocoon-like privacy of the cabin. We have never met before but have carried on an email correspondence and are aware that we share certain interests and fantasies pertaining to masturbation.
Wearing only our bathing suits, we talk and play and tease a lot. We have a drink, take a swim overboard, make a snack, sunbathe-all the while talking and revealing more of the secret sexual part of ourselves; discovering more of what we have in common. Always knowing that when both are ready, we are going to strip off our bathing suits and let each other in on our private ritual of masturbation. Neither of us has ever masturbated in the presence of another person.
Still in our bathing suits, we begin walking the other through our respective masturbation rituals. We talk about our special places, preparation, props, foreplay, fantasies, feelings, positions. I say that one of my favorite fantasies is to imagine you bending over various things (the engine hatch, the high captain's chair, the galley table); able to see your bare ass and the backs of your thighs. You say you have a similar fantasy and are willing to try it if I am, as long as we're wearing our suits. After awhile, I confess that imagining but not being able to see your bare ass is making me crazy. You say that the bulge and the huge wet spot on my bathing suit is making you crazy. It is the sign that we are ready to masturbate. We just have to get over the last bit of trepidation. It has always been so private before.
We decide you will go first. I can see you blushing as you peel off your bathing suit and lay on your back on the padded engine hatch with your legs spread wide. I stand between your legs and flick my fingers across my sun-sensitized nipples as you roll your hard nipples between your thumbs and index fingers. I love standing between your legs where I can see your smooth thighs, your puffy wet lips, and that tempting little bit of ass that is visible from this position. Pussy is the most mysterious thing for me. The part that fascinates me is on the inside, hidden from view; darker and more mysterious for me than the 'pink' that is such a turn on for you. (For me, that dark, mysterious, raw sexuality is what the word 'cunt' is about. Not perjorative; much more erotic for me.)
I suppose there is nothing mysterious for you about my cock. I know you love looking at it and thinking about what you can do with it. But mysterious? I don't think so. It is long and hard, sticking straight out from my firm, muscular belly with a slight upward curve. Little drops of slippery fluid puddle around the slit-hole at the tip. I know you like seeing that. I know that your mind goes to all the things you could do with that tiny, almost tasteless drop of lubrication. You could flick it off with the tip of your tongue and roll it around your lips. You could gather it up with a fingertip and rub it into your nipples. You could massage it into your clit. But for now, I use my own fingertip to rub it around the head of my dick, anticipating what it will feel like when I beat off later, feeling totally naked and shamefully exposed while I pleasure myself in front of you. The anticipation of it makes me shiver.
The rule we have agreed upon is that before you can masturbate yourself to orgasm-in that delicious foreplay when you tease yourself but withhold full stimulation-you must confess all of your horniest masturbation fantasies and ways of pleasuring yourself. Because I know you love anal, you must confess to me, while naked and aroused, everything you have ever stuck into your slippery butt hole. Everything you have ever craved having deep inside you-I mean way up your ass where you can feel it pressing hard against your insides, so deep and hard that the pleasure-pain makes you shudder.
You insist that you have never penetrated yourself that deeply, but you tell a story that gives me a deep insight into your sexual mind-the one sexual organ that fascinates me even more than the invisible depths of your cunt. You tell me about a time when you were naked and spread open like you are now, touching your hard nipples while a guy teased your clit with feathery-light touches from the tip of his tongue. You recounted how your hips squirmed and you pushed your pussy ever so slightly in his direction to give your clit the harder, more satisfying touch it craved. But he pulled back by an equal amount, maintaining exactly the same teasing, tantalizing, FRUSTRATING pressure on your throbbing clit. Oh, how you wanted to take over and make yourself come right there in front of him! (Yes, I know you like control.) But masturbation had not been broached, so you fought off the urge and tried to enjoy the teasing stimulation.
As you settled in for a long ride, another urge began to develop in your mind. How good it would feel to have the same light, teasing touch of a warm fingertip around the rim of your anus, circling and then pausing to tap lightly right in the center of your hole. And how much of that teasing could you stand before you would be dying to have that warm finger penetrating your sphincter slightly, almost imperceptibly (but you know it's there and you crave it so badly). How long could you stand it before you would be begging him to stick his whole finger in your ass? Or would you try to hold back and ask him to 'push it in just a little bit more'? Would you dare to even show him mow much of a slut you are for things anal?
For awhile that erotic fantasy was making the clit teasing a little more bearable for you. Finally, though, the urge built to the point where you had to either act on it or stifle it. That delicious dilemma when you have to either expose yourself and take the consequences or deny yourself the pleasure that your sexual mind is screaming for. As you linger on the horns on that dilemma ('What would he think of me?' and 'Oh God, his finger would feel so good in my fucking ass!') the fantasy continues to build and change. You wonder what it would be like if you had your small anal dildo with you, and the nerve to pull it out and stick it in yourself without asking permission or saying a word. Or maybe a dildo shaped like a big, hard cock.
Listening to your story is making my dick throb and pump out more precum than I know what to do with. I could continue listening to this all night, enjoying our nakedness, my hard on, the sight of your pussy, and the intimacy of sharing our secrets. Finally, I decide to rescue you from your confession. The movement in your hips is telling me that you need to beat off until you cum in a shuddering orgasm, and you need it bad! I tell you that it's okay to start masturbating. You open your eyes slowly, almost reluctantly, as if you are not sure whether you want to be rescued or not. I think you enjoy confessing as much as I enjoy hearing. I watch as you begin a slow circular motion around the hard pearl that is pushing out between your lips. I get a mirror and position it so you can see a reflection of your pussy right next to my hard cock, and imagine what it would look like to see your pussy get fucked. I know that you want me to see the pink, but you also want to withhold it from me until you are ready. I am dying to see you push a long, slender finger into your cunt and move it slowly in and out. If and when that happens, I wonder if I will be able to restrain myself from frantically beating off until I come.
My thoughts return to your confession story. You never did tell me whether you asked for his finger that night. I would love to know exactly how you asked for it, and every thought and feeling that went with it. I wonder if you are having anal desires as you masturbate now. I wonder if you would like me to tease your anus lightly on the outside, using the precum from my cock to make it slippery, and then stick my curious finger all the way in. I would love the intimacy of having my finger in your ass and knowing that I am fulfilling your secret desire. I could rescue you right now and just do it. Just move my hand down beneath your pussy toward that little bit of bare ass I can see in this position, slip a finger between your buns and feel for your hole. Once I find that little pucker, I can press the pad of my finger against it until I feel your sphincter start to yield. With only the slightest bit more pressure, you would feel it moving inside you. But no, this is your show, News Lady. I'm going to wait until you ask for it.