A Helping Hand (a Fantasy)

A Helping Hand, a fantasy

Kat: "Heyo"

Jim: "Hey there Babygirl! What are you up to tonight?"

Jim: "Your usual mischief?"

Kat: "Heh. You know me too well!"

Kat: "Not much, hbu?"

Jim: "I was trying to relax, maybe get a quick nap before work later, but it's not going so well"

Kat: "Why? What's the problem?"

Jim: "Well, I seem to have a not-so-little problem, that's keeping me *up*"

Jim: "Have you been able to get any relaxation in, or are you still all frustrated, too?"

Kat: "Grrrr! Not really! Been too busy! Why do you ask?"

Jim: "Well, I had an idea..."

Kat: "Really? What are you thinking?"

Jim: "We're pretty good friends, right? I mean, even though we've only known each other a few months, right?"

Kat: "yeeeeaaahhhhh?"

Jim: "And, we've had some *interesting* conversations, but we always seem to get interrupted..."

Kat: "That's soooo frustrating!"

Kat: "What are you thinking?"

Jim: "Well, tell me if I'm over the line, but maybe we can help each other out"

Kat: "wdym?"

Jim: "Weeeellll...we both seem to have the same problem, and no great way to resolve it."

Jim: "And, you know I'd offer to *lend you a hand* (or any other appendage you desired) if we weren't so far away from each other..."

Jim: "So, maybe we go out on a limb here, and use this technology to help us *scratch the itch*"

Kat: "Ugh! I'm climbing the walls here some days. It's been soooo long!"'

There's a pause of a few minutes, and I'm wondering if I scared her off, if it was too much. And then...

Kat: "Are you serious? Are you suggesting what I think you are?"

Jim: "Can I show you something?"

Kat: "Suuuure?"

Jim: "Hold on a sec..."

I quickly switch to camera mode, and try to line up a shot, but my hand is shaking, so I stop, and take a deep breath. This is either going to be a great experience or make a huge dent in whatever this thing is that's been building between us. But I can't take the tease, the uncertainty anymore. So, I get my hands steady, find a good angle, that shows me in the best light, and snap a picture. Not bad. Before I lose my nerve, I send it to her.

Kat: "OMG!!!!"

She's then silent for another couple of minutes, and I'm getting worried. Did I just fuck up?

Jim: "Kat? Say something, please!"

Kat: "Is that you?"

Jim: "I told you I had a not-so-little problem on my hands..."

Kat: "I can't believe you sent that!"

Kat: "But, it's soooo hard!"

Jim: "So, you liked it?"

Jim: "And you're not mad?"

Kat: "OMG! No!"

Jim: "Would you like to see more?"

Kat: "Really?"

Jim: "I mean, if you wanted to..."

Kat: "Can I?"

Jim: "Anything for you babygirl!"

And, once again, I go to the camera. This time, I wrap my hand around the shaft, stretching the skin tight. Making myself throb, as hard as I've ever been. I look at the pic, and it looks great. So, I send it quickly.

Kat: "Ooooohhh! I like that! Is it always like that?"

Jim: "Like what?"

Kat: "Hard, and red...that vein up the side..."

Jim: "No. Only when I'm inspired."

Kat: "Wdym?"

Jim: "You, babygirl. It's like that because I was thinking about you..."

Kat: "Really? That's kinda hot... I love that curve"

Jim: "You're hot."

Jim: "And you've been driving me crazy for months, all these times we started something & were interrupted... All the flirtations, the sexual innuendo"

Kat: "You're so sweet! And, yeah, it's been kinda getting to me too."

Kat: "*Knowing* that I turn you on, and seeing proof, I hafta say...it's made me horny!"

Jim: "You're always horny! Not that that's a bad thing!"

Jim: "And, proof or it didn't happen!"

Again, there's a couple minutes of silence. Enough to make me worry that I've gone too far.

Jim: "Babygirl?"

And, then it happens... "Incoming pic" I quickly click on the icon to expand it, and there in full color, in all their unclothed glory, is a set of breasts. Magnificent. Round, and so soft and pillowy-looking. A faint tracery of veins under the surface of the creamy, milky white skin. Medium-dark areola, pebbled in reaction to cold or arousal. And a set of lovely reddish-brown nipples, standing out fully engorged. So kissable, so suckable... I would love to nibble on them, and hear her moans...

Jim: "Wow!"

Kat: "That's all you have to say?"

Jim: "Wait...first I have to put my eyes back in my head, then roll my tongue back into my mouth, and clean up all the drool..."

Kat: "Harhar! So funny!"

Jim: "Seriously, they're gorgeous! Just like I pictured them!"

Jim: "And, honestly, something that I wasn't sure I'd ever be lucky enough to see!"

Kat: "Well, after those pics you sent me, I had to show *some* appreciation!"

In for a penny, in for a pound...

Jim: "So, what do you think of my idea?"

Kat: "What idea?"

Jim: "Us, helping each other out..."

Kat: "Oh, that!"

Jim: "Yes, that!"

Kat: "Are you serious?"

Jim: "Uh...yeah! I wouldn't have sent you the pic otherwise!"

Kat: "Um...maybe?"

Kat: "What did you have in mind?"

Jim: "Well, we could do this a couple of ways. We could tell each other a story, describing what we're doing, or doing to each other, and send pictures as we go."

Jim: "We could have a voice chat, telling each other what we're doing, maybe talking dirty as we go"

Jim: "Or....we could do a video chat, and watch each other as we undress...and then as we relieve our frustrations. Maybe tell each other what we'd like the other to do?"

Kat: "ooooooooooooooo"

Kat: "You have such a dirty mind daddy!"

Jim: "You have no idea babygirl!"

Jim: "So, what do you think? Are you game?"

Jim: "And, which way do you wanna do it?"

Kat: "I dunno! I've never done something like this before, but those pics got me so hot! And I wanna see more!"

Jim: "Really? You've never touched yourself for someone else before?"

Kat: "No, not really. Maybe a little tease while undressing, but not really!"

Jim: "This should be fun! And hot! I've never done it this way before, long distance..."

Kat: "Is that what you want to do?"

Jim: "If you're comfortable with it...yes. Oh my god, yes!"

Kat: "Well, then, how do we do this?"

I had to stop and pause. Except for my first serious gf, I had never touched myself in front of someone before. We had touched each other, but never masturbated in front of each other. My last ex wouldn't even admit if she masturbated or not! She claimed that she never did.

So, how to do this? If we're going to type, it's going to get awkward, trying to keep the camera focused, and then type, then place the camera back. And trying to use two devices, one for text and one for video, would become awkward as things progressed. The best option was also the most intimate: tell each other verbally what we wanted to do, how what we were seeing was making us feel. Then, we could keep the camera focused on what we were doing. I wonder how she would react to this suggestion?

Kat: "That sounds so hot! I can't believe I'm seriously thinking about doing this..."

Jim: "Do I have to send more pics to convince you further?"

As I finished typing that, I used the camera to get a shot down my body, wearing nothing but the tablet propped up in my lap, and sent it to her, before she talked herself out of this. I captioned it "so you say you like dad bods..."

Next thing I knew, I was getting a video chat request...which I quickly accepted (my mama didn't raise no fools!)

Jim: "Hey there sexy!"

Kat: "Hey...you play dirty, old man!"

Jim: "What do you mean?"

Acting all innocent...

Kat: "That pic! You know I like dad bods! That was so not fair!"

Jim: "What's not fair is all those clothes you still have on, and the fact that you're still only showing your face!"

Grumbling, she backed her iPad up so I could see her upper body, and those glorious breasts!

I must have let out a noise...

Kat: "Like that, do ya?"

Jim: "Of course! How often do I hafta tell you that you're gorgeous! And, now you'll be able to see that I really mean it!"

She began blushing a bit at the compliment.

Jim: "As you can see, I am so ready, but we can stop if you're not sure..."

As I panned the camera to show myself hard and throbbing. I'm wondering if I scared her off, if it was too much. And then...

She bit her lip for a moment, obviously thinking. Then, she stepped back from the iPad, so I could see her fully. She was wearing a pair of sweatpants that molded to her curves, and almost nothing else that I could see.

Jim: "That expression, the lip bite...that is soo hot!"

She chuckled. Followed by swiping her tongue seductively across her upper lip.

Jim: "Now you're just playing dirty, babygirl!"

She just chuckles and gives me a sassy wink. Her shirt is pulled off her shoulders, leaving her breasts and shoulders bare. She pulls the shirt up on one side, covering a breast, but doesn't really place it on her shoulder, so as soon as she releases it and lets her arms drop, it slides off her shoulder, catches momentarily on her nipple, then slides back down to her waist, basically doing a slow-motion striptease.

I groan again.

Jim: "You're sure you haven't done this before? You're a natural seductress!"

She gives me another saucy wink. But then she gets a slight frown.

Kat: "I'm not sure what to do next. I mean, I know what I do when I'm by myself, but..."

Jim: "You mean with the mirror?"

Kat: "I told you about that?" She blushes, a faint pink visible all the way down to the top swell of her breasts.

Jim: "Yes! You don't know the images that put in my mind babygirl! How hard I was after that conversation!"

Jim: "How hard it is making me right now, thinking about it."

As I pan the camera down from my face, to show me still rock hard and visibly throbbing.

Kat: "Oh my god! You're still so hard!"

Jim: "Of course I am! Those gorgeous breasts showing..."

Jim: "Thinking about what we are about to do, if you're still game?"

Kat: "You really want to watch me?"

I just gesture at my hard length, pulsing in time to my heartbeat.

Kat: "Ok! I guess I have to believe the evidence in front of me..."

Jim: "If only it was right in front of you! I so want to taste those sweet lips, caress those magnificent breasts, pull your hips against mine, and feel your belly and mound pressed up against the length of me..."

She lets out a low groan.

Kat: "That is so hot! I wish we could do that too! I need some relief now though, and you look like you're about to burst. So, how do we...?"

Jim: "There's something I've been dying to know, to see, ever since we talked about your surgery a couple of months ago..."

She arches her eyebrow, a slight smirk on her lips, already guessing the direction of my thoughts.

Kat: "And that would be?"

I'm just about to say what I want to see, when I get an idea.

Jim: "You know, I've only ever seen your ass once, in that bathing suit. And you claimed that the picture was heavily edited. I want to see it in all its natural glory!"

Jim: "Turn around and bend over!"

I suddenly put just a bit of authority in my voice. She jumps, just a slight bit, but I notice her nipples tighten just a little bit. I had remembered that she said she was a submissive. And, we had played a little bit with casual daddy/dom themes in conversations before. Something that was an immense turn on with her, the way she could switch from casually wanton to little girl submissive from one moment to the next.

She obeys, looking at me, at the camera, over her shoulder.

Jim: "Now, slowly bend over, and slide those sweatpants down off your ass as you do so! I see a naughty girl who needs some punishment!"

She groans again, louder. Then she puts her hands to the waistband of her sweats and bends forward slowly. As she does so, she starts to slide the waistband lower, first revealing the top of her panties, then the dimples above her ass. As she slides the sweats lower, the top of the cleft between those round cheeks peeks over the waistband. She inches the material a few inches lower, now baring half of her ass cheeks to view, and gives a little shimmy, causing those glorious globes to shake tantalizingly.

Jim: "You are such a bad girl, teasing daddy like that! What do we do with bad girls, babygirl?"

Her head comes up a bit at that, and a fierce look comes into her eyes, quite at odds with the tone of voice of her reply, "They get punished daddy."

Jim: "That's right babygirl! Now, finish sliding those sweats down off your ass, and put your hands on the bed, assuming the position!"

She slides the sweats the rest of the way down to the tops of her thighs, exposing that luscious ass, now clad in only a lacy, yellow thong. Then, she bends forward just a bit more, and puts her hands on the edge of the bed.

Jim: "Arch your back some more for daddy! And place your feet shoulder width apart."

She obediently obeys, arching her back, stepping into position. This shows her ass off, slightly parting the cheeks, making me groan at the sight.

Jim: "Imagine my hand on the small of your back, holding you in place. Are you ready, babygirl?"

That fierce look is still in her eyes, and she has her lip between the edge of her teeth. "Yes daddy," she says meekly.

Jim: "I'm not there, so you're going to have to spank yourself. I better not catch you going easy on yourself"

Kat: "No daddy, I wouldn't!"

Jim: "Count out the spanking, and remember, if you miss any, we start over!"

She nods, "Yes, daddy."

Jim: "Begin!"

She brings her hand down on her right ass cheek, and a load smack sounds out.

Kat: "One, daddy!"

Jim: "Again!"

Kat: "Two, daddy!"

Jim: "Harder, two times!"

Kat: "Three, oooh, four"

Jim: "Other side, again!"

Kat: "Five, daddy"

The light in her eyes has grown a bit wilder, and her breasts are swaying with each swat of her hand. Her hips jump slightly forward and back at each spank. I am leaning forward, watching her intently.

Jim: "Again, babygirl!"

Kat: "Six, daddy"

Jim: "Is my babygirl sorry for being such a tease? Again!"

Kat: "Oooh, yes, daddy." There's a brief pause, and I think I'm about to have to call her on it, and tell her to start over, when she remembers "Seven, daddy! Seven!"

Jim: "Very good babygirl! Again, harder!"

Kat: "Eight, daddy!"

Her hand comes down with a sharp crack, and a handprint shows lightly across her left cheek, which is starting to turn a nice shade of pink.

Jim: "Much better babygirl, but I want to see a full handprint! Again!"

Kat: "Nine, daddy"

Jim: "Has babygirl learned her lesson? I want you to switch hands again, and give me a REAL spank!"

Her right hand comes down with a loud smack, and immediately a handprint starts to form, white in the center, and red outlining each of the fingers.

Kat: "Ten, daddy!" Then mumbled mostly under her breath "ouch!"

Jim: "Did that hurt babygirl? Have you learned your lesson about teasing daddy?"

Kat: "Yes, daddy, yes, I will be a good girl!"

Jim: "Ok, I believe you. That was very good babygirl!"

Jim: "Now, get some soothing lotion, and kneel on the edge of the bed. And I think we can take those sweatpants all the way off now"

She hurries to strip the sweats the rest of the way off and tosses them off to the side. The shirt comes quickly over her head as well, leaving her in just the lacy thong. She tosses the shirt off camera, too. Then she scampers off screen for a second, breasts bouncing and swaying enticingly, and comes back with a bottle of lotion. She climbs up onto the foot of the bed, and kneels down, facing away from the camera, with her ass up in the air, and her elbows down on the bed. Then she turns to look at the camera. "Like this daddy?"

I groan at the sight of her, with the two handprints, one on each cheek, now glowing red, ass uptilted, thighs slightly spread, back arched. It is a glorious sight, absolutely perfect.

Jim: "Yes, babygirl, that is perfect!"

Jim: "Now, rub some lotion in, soothing your ass after the spanking."

Kat: "Yes, daddy!"

She squirts a small blob of lotion in her hand, and starts rubbing it into her left cheek. When she realizes it isn't too bad, she takes a little bit more of the lotion and coats her ass cheek liberally. Then, she switches hands, and repeats the process on the other side, all the while looking cheekily back at the camera, watching the expression on my face.

"Does daddy like that?" She asks, as she takes both hands and rubs her ass, grabbing the cheeks and spreading them slightly, revealing the line of her thong running down between her legs.

I groan again, more loudly, and angle the camera once again so she can see my long, hard length, still throbbing and red, and as she watches, a small drop of precum forms at the end, and drips down my shaft.

Jim: "I think you can see how I liked that!"

She is mesmerized, watching the drop roll down my shaft, and her tongue comes out again, licking her upper lip. Then, almost like she does it without thinking, one hand grabs her breast briefly, lightly squeezing the nipple, before sliding down to stroke her inner thigh, before coming to rest on her pussy, slowly squeezing and moving in slow circles.

I groan again, more loudly, and another drop of precum oozes out. Her fingers circle a bit faster, and a low moan can be heard from her end.

Jim: "You like watching that, don't you?"

She startles, briefly, realizing where her hand is, and blushes again, flushing a darker pink this time, all the way down to the top of her cleavage.

Jim: "How about we do something about that, before one of us explodes?"

She looks up at me, briefly, before she nods.

Jim: "Why don't you put some pillows against the end of your bed and lean back. This way, you can get comfortable, and see your mirror. You can place your iPad at your feet, but off to one side slightly, giving me the same view you have, but so I can also see your beautiful face."

Jim: "I want to be able to watch you when you come."

At that she lets out a longer moan, and her hand, which was just cupping her pussy starts circling again, more rapidly. Then, she grabs her breasts, one in each hand, mounding them up on her chest, presenting a lovely cleavage, before squeezing them lightly, and pinching her nipples. She then gets up, grabs a couple of pillows, and her iPad, and we spend the next couple of minutes arranging everything to each other's liking. First, she had me place the iPad between my legs, getting an up close view, but it is too close, and she can't see my face. Then, I tried a side view, a little closer to my hip than hers, and aimed more across my body, which gave a nice view of my length, and the slight up curve, but she decided it was still too focused. Finally, she settled for a view from my point of view, down across my body. She pulled my profile pic up on her phone, off to the side, so she could view my face at the same time, and we were ready.

Jim: "What do you normally do, babygirl? I want you to feel your best, not try to tell you what to do, and have it only end up being mediocre. I know every woman is different, and normally I would love to spend hours exploring you, but that would be really awkward, trying to tell you how I would like you to touch yourself!"

Jim: "And I don't think either of us has the patience right now for hours of play, am I right babygirl?"

Kat: "Hah! You've got that right! Watching you throb like that, spanking myself for you has me sooo worked up!"

Jim: "Why don't you show me then? How wet are you? I don't think you need those panties anymore, do you?"

Kat: "Omg, they are soaked right now! That spanking really got to me, especially the way you got so direct! I was so turned on putting that lotion on, I didn't even realize I was touching myself after! I've never done that before for someone!"