'Hello, Friday Night Girl,' I say, deep, low, and sexual. Jane plays along, 'Hello, Friday Night Guy,' she replies, her musical Southern accent lilting, flirty. I forget how long we've called each other these pet names, and Jane probably thinks it's all a game. But she's starred in my favorite sex fantasies for years, and every time I dial her up I am pumping and stroking my big dick for her and shooting cum everywhere by the end of the chat.
Jane, 48 at the time of this writing, lives in the midwest and is a family friend of mine. I'm 35. She was, briefly, my babysitter, so that's sort of where the fixation comes from. But I've always had a thing for older women and Jane-single, attractive, confident, smart, and a good girl with whom I very much want to be bad-is my number one crush.
'What are you up to, Friday Night Guy?' she asks. Well, Jane, if you must know, I am completely nude, and I've poured olive oil all over my throbbing cock, and I'm wondering if you hear any slick, slapping, smacking sounds-because that's my dick slithering liquidly in and out of my left hand while I fantasize about spreading your legs, one ankle in each hand, and rubbing my dick all up and down your slippery pink pussy.
'Oh, not much,' I say, 'just calling to chat.' And we talk about her day, and mine. I'll usually have some flirty thing in mind before I call, or some anecdote about my sex life that I share with Jane, discreetly, of course. But when I'm being flirty or talking about girls or sex, that's a good indication that I am nearing my orgasm. And let me tell you, it is hot, and wonderful, and feels so good.
'You're so crazy,' she says at the end of my funny, sexy story, while I shoot my cum for her. This is the only time when I masturbate that I do not moan Jane's name and say she's making me cum, even though she's finally there to hear it. My chest is pounding, from trying to control my ragged breathing and stifling moans of pleasure, and my pelvis is swiveling, rising up off the bed, back arching, my spasms spouting and spurting and streaming steaming hot cum all over my hand, stomach and chest. I usually see stars when it's all over.
'Goodnight, Friday Night Guy,' Jane purrs.
'Sweet dreams, Friday Night Girl.' I say, still throbbing, still thick, slick and sticky.
For reasons I can't really get into, let's just say it would be too great a risk to proposition Jane and have her refuse. I could handle the rejection, but I wouldn't want to damage our friendship, which I value and I know she values, and I definitely wouldn't want to make her relationship with my family irrevocably awkward.
But she'll be my number one sex fantasy until I can't cum or get hard anymore and even then I'll still dream about her. This summer Jane was my 'date' to a pretty high society affair in our hometown, and when I drove over to pick her up, she asked me to clasp the top of her dress in the back. What I really wanted to do was unzip her dress, fondle her boobs, bend my sexy Friday Night Girl over the couch ... mmmmmm ... her warm, girly scent filling my nostrils as I put my hands on her hips ...
This summer I visited Jane on a drive West, staying in her guest room for a couple of nights. She had to work, so I had her place all to myself, and I engaged in some wickedly premeditated masturbation. I had been planning it for two weeks, which is how long I went without getting off, just because I wanted to have a spectacular cum-shooting orgasm in Jane's bed.
After Jane left for work that first morning, I stripped naked and went into her bedroom. My dick is always its biggest and thickest and I am always my horniest first thing in the morning. I was musky and looked very male walking into her bedroom with my semi-hard dick dangling and my big bouncy balls swaying, heavy and full of cum. Like a horny teenager, I was on the hunt for her panties, hopefully an exciting pair. Bingo, in a basket was a cheetah-print pair, I guess matching the slippers on her bedroom floor. Then I went back to the bed, roughly flinging the bedspread aside. It was going to get nasty, and I didn't want that in the way. The plastic soda bottle that I use on trips to carry olive oil as a masturbation lube was on her night stand. I was ready to go.
I started rubbing myself all over her mattress, humping and sliding over the side of the bed where she lay every night. I lay her pillows underneath my chest, pretending they were her, while I rolled my hips and pantomime fucked the mattress. I wanted the scent of my body all over that bed.
'Oh yeah, Friday Night Girl,' I said, breathy, detached, rubbing my body against Jane's bed. If Jane could have watched me, she would have seen me acting out just how I would fuck her, me on top, back arched, head thrown back, smiling, rolling my hips, long strokes, then short pumping fast ones, both of us looking down to watch me pump her, loving the feeling of our bodies.
I looked down; the pre-cum from my cock had left a faint trail down the mattress. I rolled over on my back and started stroking myself, moaning Jane's name, trying to make the sexiest sounds of pleasure I could, wanting her to walk in the door by surprise and hear me and know immediately what I was doing. I took deep breaths, to enjoy the moment and to relax my instinct to tighten up and orgasm. My smooth, shaven balls nuzzled and bounced against her fabric, slowly, then faster, as my right hand pistoned up and down my shaft.
After a few good minutes of that, I reached for Jane's panties and wrapped them around my cock. first winding the crotch around my shaft, then the rear, the smooth satiny fabric sending a slight naughty chill up my spine when it rubbed my cockhead. I found my zone, that stroke where I felt the hardest and most pleasurable yet always in control and not about to cum. Fucking Jane's panties, I lay on her bed for I don't know how long, my vocalizations getting louder and more brave, my movements more pronounced and sexual. Maybe Jane had a security camera on the bedroom? Maybe she had an audio recorder? I pretended she did and gave her a show.
But soon I was just overcome with an incredibly vivid image of Jane masturbating in her bed, giving me a show. In my mind's eye she had a pillow under the small of her back, and her panties were down at her ankles and a night shirt pulled up over her jiggling boobs, nipples pointing straight up like pencil erasers. Jane was spreading her pussy, exposing her clit, which she strummed rhythmically. Her eyes were closed and her mouth hung open in a sexy pout, soft moans escaping as she rocked gently.
I wanted to be there with Jane, to coo to her softly, sweetly, and say dirty things to push her fantasy and libido further than she'd taken it before. I wanted to nibble, lick and suck her nipples, feeling them get hard in my mouth and Jane's breath get shorter, higher, softly in my ear. I wanted to tell Jane how sexy she was to me, how beautiful she is when she's masturbating, how fascinating it is, watching her cum, and how she looks like the definition of sex to me. I wanted to lick my two fingers and slide them inside Jane's slippery pussy, locking her gaze, pure lust in her eyes, both of us nodding open-mouth uh-huhs and yeah babys at each other as she grinds and gyrates into my hand, reaching up to her G-spot and plunging harder and faster and making Jane, Miss Pussy Princess Triple X-Rated Friday Night Fantasy Girl explode and spasm and buck and hump and rub and cum (give me your pussy, Jane babe) and cum (yeah, grind it into me honey) and cum (oh fuck yeah just like that babydoll) and cum her hot (yes!) wet (yes baby! go for it!) steamy (ohh Jane!) pretty (cum baby!) pouty (cum for me!) pink pussy off.
I took Jane's panties off of my dick and caught my breath. I got up, went to her bathroom and took a drink of water. Over at her vanity, I took a bottle of her perfume, lightly dabbed my index finger on the tip and then under my nose, so I could smell her cute, sexy aroma. Of course I sprayed my dick, just like a teenager doing the same thing with cologne. Standing in her mirror, I stroked myself back to full hardness, and then took a tube of her lipstick. Gently, so as not to crush the tip, I wrote JANE on my dick. And then I circled my cockhead, and touched the tip of the lipstick to its slit.
Back to the bed. Things were going to get messy. I've seen the damage olive oil can do, and I didn't want to get too much on Jane's linens. So I took my guest washcloth and laid it underneath my crotch as I leaned back on her bed again, cock pointing straight up, arcing pleasantly. The red lipstick JANE swayed to and fro as I uncapped the olive oil, carefully, so as not to spill it, and poured a little in my left hand. Then I recapped the bottle, and began working the oil into my dick.
'Ohhhh, yes, Jane, my hot sexy Friday Night Girl!' I moaned, arching my back and fucking my hand. I imagined the slick stroking and sloshing noises to be the sound of Jane's pussy, her mouth, her lubricated hand pleasuring my cock. 'Fuck, Jane babe, you make me feel so good baby,' I sighed, rolling my wrist, pumping and stroking in her bed. Never have I felt such a raw lust for a woman as I did masturbating and moaning and writhing in Jane's bed. My balls had tightened up, no longer jangling and bouncing, primed, ready to shoot ecstasy all over Jane's bedroom. I moaned her name, loudly, wanting to be heard; I told my sexy Friday Night Girl she was going to make me cum.
And suddenly I was there. 'No!' I cried. I felt my climax begin to move up my shaft. Not wanting to cum yet, I took my hand off my cock as a last resort. But I was already past the edge. A small pearl of cum pooled in the slit. My cockhead bulged. The lipstick 'JANE' had long been smeared off. Breathing deeply and trying to relax my PC muscle, I managed to raise up, and lay Jane's cheetah panties on her pillow. A few drops of cum fell as I took my dick in my hand to end the session.
'OH YEAH JANE!' I wailed, 'AHHH!!! OH JANE!! OH BABY, YEAH! CUMMIN' FOR YOU!'
Roaring my desire for her, I pumped huge, pearly streams all over Jane's panties and pillow and bed. Each spurt was a confession; each drop the chance to be caught; each stroke a soul-baring expression of years of lust. Everything came rushing out in four ... five ... six ... SEVEN spasms, an unbelievable, pent up orgasm that beat all expectations I had in the two weeks I'd abstained. I'd cum for Jane like no other woman ever made me cum before.
Jane's panties were streaked with cum. Huge, hot, pearly blobs of it all over the crotch, from where the last of my orgasm had trickled out. The pillow and mattress showed the force of my ejaculation, amazing rope trails from my first two spurts, which landed some two and a half feet away, nearly hitting the headboard. The unmistakable scent of cum hung in the air. I spread it over her panties with the tip of my dick, enjoying the come-down from my orgasm before making plans to cover up this mess.
Later that day, Jane called to make plans for dinner. She asked what I did all day, and I told her I decided to get a work out and relax instead of hustle around town seeing touristy things. 'Oh and another thing, I hope you don't mind,' I said, 'but I did a laundry.'
That night I stroked, deliberately loud, hoping to produce enough noise that Jane could hear me, but immediately know I was jacking off so she wouldn't rush into the room to see if I was in pain or something. I'm not sure if she did hear me. But I had a great cum in her guest bed. This time I left my cum on her linens for her to find, if she really wanted to look for the evidence.
The next morning I had to get on the road early. We hugged and said our goodbyes.
'Don't forget to call me when you get there!' Jane said.
'On Friday night, girl. Right?' I said, winking.