Chats with Anna 01

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Intro, chat and webcam transcript.
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We're quite possibly never going to meet IRL, that's one of the reasons why we've been able to be so candid with each other, why we've never felt any need to hold back. No shame, no hypocrisy. The geographic distance is not the true reason, a mere two-hour drive wouldn't have kept us apart, but the social pressures would make impossible anything but, at most, the very occasional tryst.

It was she who contacted me, complimenting me on some novels of mine that she'd read (published under another nickname on another site) and asking for critique on a novel she'd written herself. Literary advice quickly turned into personal questions about me, I told her about my dead marriage and how my writing was actually my escape into fantasies where I could live out what I wasn't getting in real life. She, in turn, freely gave insights into her life, sharing thoughts, asking for advice. Still, we both know it can't be. The age difference is too great. Had she contacted me a mere couple months earlier, I would have been three times her age. As it happened, she turned 19 first and that gives you a bracket on how old I am as well. So not only am I married with children her age, but I'm also older than her father. More like her father's boss, in fact; both in age and in profession. Which, in a fantasy relation like ours, can be a thrill but would just bring too many problems to the table in real life.

Nevertheless, we've become cyber-lovers. The worry that she'd be some guy masquerading as a girl, was quickly quashed by a candid photo of a slender topless girl holding a handwritten note with my nickname on it. Her concerns that friends had had their nude pictures leaked all over the 'net, were assuaged when I sent her pictures of myself. Yes, who would be interested in nudies of a middle-aged guy like me? Answer: Anna! That's not her real name, of course, but it's the nick she used when she first contacted me and it's stuck, both in my mind and in my mail app which still tags her letters with that name.

Body pictures grew to voice calls over Skype (still using anonymous accounts), sharing our real first names and finally full names. The day when I sent her a full-body fully dressed picture of myself in front of the BBQ, she replied with a full mirror self-portrait with her skirt lifted and panty pulled aside to show her shaven pussy. The contrast between her youthful face with careful makeup and the brazen flashing of her cunt, was thrilling, to say the least.

She has an exhibitionistic streak that I find has brought out something similar in me. She also gets excited by embarrassing or humiliating situations, which has led to some thrilling games between us as well to my sending her pictures I would previously never have even considered taking. We've shared fantasies, discussed turnons and -offs, worries about impotence (me) and about contracting some STD (her!). I've told her about past lovers, bi experiments and threesomes back in the 70's and 80's, she has asked me for advice about potential new boyfriends, then rejected them (the boyfriends, not my advice) on the grounds that they weren't "dirty" enough, but she still carefully maintains a wholesome façade, keeping her "secret slut" side under check to avoid any bad reputation in the small mining town where she still lives. She wants to move away from there and go to university soon, but it's a big step and the cost is a worry. And, since she'd be going to one of the college towns and not to the state capital where I live, it wouldn't make our relationship any easier. I've become her "porn mentor," her "smutfather," she my "dirty goddaughter". We're a pair of attention-whores egging each other on and enjoying it immensely. My one regret is that I'm not 30 years younger. Or even 20. Then I would have swept her up and away without a look back. But on the other hand, 30 years ago I wasn't the man I am today and if me-then had met her-now, I would probably have been one of the "not dirty enough" rejects, IF I'd even made it to the tryouts.

So, that will have to do as introduction. There's more, lots more, but re-counting it here in this intro would get tedious and, who knows, might spoil some future installments in the saga. I understand if you're now shaking your head and smirking over what a fraud you believe me to be. That's all right. I wouldn't believe this story myself if I'd read it on the net and I don't know if I'll ever be able to prove it to anybody. Believe what you will. I hope you will enjoy it anyway. Oh, and one more thing. I'm not posting this under "age play," despite our difference in age. This is my choice, based on how the age gap is more of an obstacle to us than a thrill. Sure, we can play on it at times but that's secondary. Our strong connection, having become "soulmates" despite the distances between us, is the key. And since it's all cyber; mail, chats, phone and video, I've chosen "Letters and transcripts" as more appropriate.

And one more thing. A while back, i sent her two "Clone-a-Willy" casts of my cock. Look them up on the net if you don't know what they are.

That, then, brings us up to last week. I was sitting at work, bored, with a half-hour until next meeting leaving too little time to do anything useful and not even any company email to deal with, so I turned on my personal tablet and logged on to our chat. She was already online and pounced immediately.

Anna: "I read that new story of yours. It was long but really good. I'd planned on reading it in chunks since I was tired but I just couldn't stop."

Me: "I guess 'impossible to put down' is just about the best praise an author can get. :-) "

Anna: "Yes, exactly. You have such a wonderful dirty imagination."

Me: "Dirty imagination is my middle name!"

Anna: "Yes, I've noticed. I like it! :-D "

Anna: "I'm horny."

Anna: "From reading"

Anna: "It's your fault."

Anna: "I'm in bed right now, playing with my nipples. They're stiff."

Anna: "I need cock!"

Me: "I can't GIVE you any real cock."

Me: "I might be able to SHOW you one."

Anna: "Ooh, I like that."

Me: "But I can't run video and chat at the same time on my tablet so you will have to talk to me instead."

Anna: "Of course. You mean there's a chance later?"

Me: "Handicap toilet."

Anna: "You're insane! Is your meeting at 2?"

Anna: "My Mom is still at home."

Me: "Oops, that complicates things."

Anna: "She's getting ready to leave in a few minutes, though."

Me: "OK. Date?"

Anna: "YES!!"

Me: "Can you 'warm me up' while we wait? Those stiff nipples, for example. I've never seen any closeups of them. Before, while you're pinching one (hard!), after..."

Anna: "You want me to try and show later? On video?"

Me: "No, now! Pictures."

Anna: "Sending two now. Very little difference, though.

(I received two closeups of a nipple. Quite stiff in both pictures. She'd been telling the truth about them already being stiff.)

Me: "Mmm, there is some difference. Looks good. Can I taste?"

Anna: "I'd love you to."

Me: "I think I will find it hard to resist biting. Or at least nibbling."

Anna: "Which dildo do you want me to use? You have a choice of five."

Anna: "1 Largest yellow with weaker vibration. 2 Smallest white, hard, without vibration. 3 White with jelly tip. 4 Perfectly shaped cock in latex, but no battery for the vibrator, or 5 his darker brother, slightly softer and no vibration."

Me: "I want to see Willy1. In your ass!" (Note: Willy1 is the first cast of my cock, by-the-book with a simple "bullet" vibrator inside, but she'd forgotten to get any battery for it. Willy2 is a darker dildo made from the same mold but without vibrator so instead I'd endowed him with a 6ga curved barbell stainless steel piercing which I'd originally worn in my own PA piercing until the weight of it caused the piercing to migrate so I'd had to give it up. Since there was no hard vibrator core, Willy2 never quite hardened all through and was slightly soft, somewhat like a cock after you've come but before it has shrunk.)

Me: "Do you have time to soften up and prepare for that?"

Anna: "Doubtful. How much time do you have?"

Me: "Not much. In that case I'd rather focus on showing off for you and you telling me what you want to see. Maybe I can get to see your face as you come. That's a dream of mine."

Anna: "OK, I promise to show you."

Me: "Am I weird for getting as turned on by your face as by your pussy?"

Anna: "Haha, no. It makes me a little embarrassed, actually. And you know what that feeling does to me!"

Anna: "Will you be wearing your headphones?"

Me: "Yes, I'll listen but I won't be able to speak. That might attract attention."

Anna: "No, I understand that. I'll ask yes/no questions at most."

Me: "I can't show my face and cock at the same time so I'll make thumb-up or -down signs to reply."

Anna: "Yes, that will work. How dirty do you want to be?"

Me: "What do you want? I can hardly undress completely so it will at most be pants around my ankles and shirt unbuttoned."

Anna: "I want to be as dirty as possible."

Me: "Let me know when you're alone."

Anna: "She's about to leave right now."

Anna: "Do you want to see all of me? I can, like, put my computer on my chest of drawers.

Me: "Hard for me to see details on my tablet. But do whatever is most exciting for you. I want to seen you HORNY!"

Anna: "Call me now!"

At this point in time, the chat transcript ends. I went to the bathroom, locked myself in and turned on the video call. The handicapped toilet has a washbasin, real walls floor-to-ceiling and a proper, lockable, door so the risk of anyone seeing me was minimal. As I dropped my pants to the floor and started unbuttoning my shirt, in was met by the sight of Anna nude on her bed, lying on her side, knees pulled up and her ass towards me. Her hand was moving something dark brown in and out of her ass. Willy2! My cock started swelling in my hand as I held it and played with it. Anna turned to her back, legs spread to show one hand holding the other cast of me, Willy1, moving in and out of her pussy while her first hand was still reaching behind her, ass-fucking herself with Willy2. Before my eyes, she threw her head back in total abandon, moaning loudly with each breath and double-fucking herself violently with the two replicas of my cock.

I, for my part, stroked my real cock in front of the tablet's camera where I'd propped it on the washbasin, but I wasn't sure if she actually saw me. What I saw of her face was contorted, eyes closed, as she pounded her cunt and ass with my cocks. As her moans increased in speed and strength, she moved the hand from her ass to play with her clit while leaving the one dildo still buried in her ass and hammering her pussy ever harder with the other.

Her moans increased further as I saw her rapidly approaching her orgasm. I, too, sped up my hand and as she thrashed on her bed in a powerful orgasm, I shot my seed into my cupped left hand, holding it close to the camera for her to see. As her spasms subsided and she fell back on the bed, she took a couple quick breaths and then sat up to grab her computer, bringing her face into full view of the camera. Whispering, she said something I couldn't hear (why did she whisper when she was alone and I was wearing headphones? I will have to explain to her that a proper Domme gives her orders in a firm and clear voice!) but I knew from her glance at my hand and the hungry look in her face what she wanted.

Picking up the tablet with my right hand so I could move my sperm-covered left hand into view and raise them both close to my face, I looked at her and then I bent to dip my tongue in the collected semen. Her angelic smile when she saw me lick at my own sperm, was incredibly satisfying to me and I smiled back as I put the tablet down to give her a brief glimpse of the amount of sperm I washed into the sink, before disconnecting the video call, returning to the chat.

Anna: "You're the best."

Anna: "Thanks!"

Me: "No, YOU'RE the best. I don't think you understand what you do to me. FOR me!"

Me: "I have to go to my meeting now. Snowball-kiss and creampie-licks. We'll hook up again tonight."

As you probably have seen by now, dear reader, Anna has re-awakened desires in me from my own experimental youth in the 70's and 80's where I tasted cock, swallowed sperm and licked my own cum out of my then-girlfriend's pussy. This excites Anna immensely. If we ever do meet IRL, against all odds, we have woved to share my sperm in every conceivable way; snowball kisses after I've come in her mouth or me licking it out of her cunt or ass to share with her in deep kisses. The mere thought makes my cock stiffen in my pants as I write this.

The epilogue came the same evening, when I came online to be met by this email from Anna.

"Hey, you. I have to confess something quite funny (I hope you agree) and embarrassing that happened. I believe and hope that you heard clearly when I came, with both your dildoes in me. It was the strongest kind of orgasm I can have. (Note: She has told me how she can have orgasms of different intensity, where after the weaker kind she can come again in just a few minutes but the stronger type leaves her drained for much longer.) I would not have been able to come again afterwards. My entire body tensed and I didn't notice anything at first. I was completely lost in the rush and at the same time I saw you come. After we had disconnected, I saw that Willy2 was half. I had tensed so much that it had been cut off... Talk about a combination of a tight ass, soft dildo and possibly a strong sphincter, that gave me a bit of a chock. So I had to use two fingers to get the other part out.

(Accompanying this is a photo of the two halves of my cloned Willy, looking to the world very much like two turds, the part that had been trapped inside her all flattened out, possibly in a cast of the inside of her colon. The two balls at the end of the curved barbell barely showing in the mass of crunched-up latex. With the photo a caption says: "Oops, what if it had been your cock in my butt instead of the dildo? :-) ")

The good part in it all is that at least you got to see when it happened. Otherwise you might have wondered what had been going on, if I'd just written to you about it some day. I'm afraid he's beyond repair. The shape is completely gone so all that can be salvaged is the piercing. I would, of course, have preferred to keep Willy2 around, but it was a tiiiny bit comical. Hope you find this a little entertaining.

I wrote back: I have in some fantasy (loosely based on my few real-life experiences in the area) written about anal fucks where "her sphincter squeezed my cock so hard, my glans swelled up inside her and felt like it would explode." Talk about prophetic! :-D

Would I like to try that out for real with her? Are you kidding? Who do I have to kill?

The next step is for me to figure a way to remote-guide Anna to drill (yes, drill!) a PA hole for the curved barbell in Willy1. She's adamant that she wants it and thrilled that it's a piece of jewellery that I've actually worn for real in my cock. She certainly knows how to make a man feel good.

I hope to have many more exciting transcripts and calls to share with y'all.

Bye for now,

/Smutfather

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