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! “
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?”
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.”
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!
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,
It was the Thursday before Spring Break, and the dorm was mostly empty. Just a few hours earlier, the halls were filled with college students getting ready to leave for their week of binge drinking and uninhibited sexual encounters.
But I wasn’t so lucky.
It didn’t start out that way though. My best friend Tara and I had planned on driving a few hours south to Panama City, Florida and spend the week in her parent’s beach house. We had been friends since high school, and were even being lucky enough to get accepted into the same college and become roommates.
But that all changed when Tara and her boyfriend Steven got serious. A few weeks ago, Tara decided to move off campus and into an apartment with Steven, which I couldn’t blame her at all for doing. Our dorm was always busy, filled with students looking for a party or a one-night stand. If you weren’t in line for a shower by 8AM, it felt like you were waiting all day long.
Instead of spending the week at her parent’s beach house, Tara and Steven went to Pennsylvania to meet his parents. She told me that i could still drive down to the beach house for a relaxing weekend alone, but i really didn’t want to spend the week all by myself in an empty condo.
I elected instead to spend the week in my dorm room, catching up on TV shows and relaxing. I had spent most of the semester in the library studying overnight or in the gym trying to get a jog in on the treadmill. I took on an extra workload, trying to get as many credits out of the way as I could.
So it was Thursday night and I was in my pajamas watching a movie in bed. I had found some margarita mix in our mini fridge, and before long, I had a good buzz going. By my third drink, I could feel my pussy getting a little wet. This always happens when I drink margaritas!
It wasn’t long before I was scouring around the dorm trying to find a dildo that Tara had given me as a present when she moved out.
“It isn’t the real thing,” she said, “but it will get the job done.”
I eventually found it and quickly stripped out of the tank top and shorts I was wearing. I turned on my laptop and found a free website with video clips on it, offering all kinds of categories for those in need.
My favorite videos have always been lesbian clips, but on this night, I found a bunch of clips from a girl on her webcam. She was sitting at her desk in just a towel, flashing her viewers for tips. I was so infatuated by this that I completely forget about my dildo, instead, I sat there for hours watching these clips.
By the end of the night, i had found my way onto a cam website, watching several girls flashing their bodies for money. I sat there wondering if I could do it, but eventually came to the realization that I would be far too shy.
That was until i saw a banner on the website promising hundreds of dollars a week to new models. The ad said that registration was easy and you could be approved and online in only a few short hours. I finished up my margarita and clicked Register.
I knew it would be too late for me to do it tonight, besides, I was supposed to be catching up on my rest this week. I woke up at 10AM and stumbled my way out of bed. By now, the dorms were completely deserted, there wasn’t even a sole in the showers. I spent time shaving my legs, and even shaved a landing strip above my pussy. Later in the afternoon, I stopped by a liquor store for more tequila and margarita mix. If I was going to do this, I knew I would need some liquid courage.
On the way back to my dorm, I pulled into a lingerie store. I hadn’t planned on doing so, it just seemed like my car had a mind of it’s own. I spent twenty minutes browsing through all kinds of sexy outfits before settling on a pink see-through teddy.
I settled back into my dorm, and immediately opened the bottle of tequila. My nerves were running wild, my hands were shaking like crazy, and I had butterflies in my stomach. Three shots of Patron later and I was feeling a little better, starting to get excited at the thought of hundreds of guys watching me. The next few hours consisted of me setting up my camera, trying to find perfect lighting, and a few more shots of tequila.
I opened up the bag from the lingerie store and pulled out my outfit. I wasn’t able to try it on at the store, there were too many people in the store and i got nervous. I opened the plastic wrapping and found a cute little see-through g-string included with the teddy. I stripped out of my clothes and into the panties, which allowed my landing strip to peek through oh so slightly. I slipped into the teddy and admired my outfit in front of my mirror.
It was 7PM and I finally logged onto the website. I had settled on having the laptop on a chair while I laid on the bed, figuring that was the best position. I began laying on my stomach with just a small peek of my ass. The room started out slow, but after 30 minutes or so, I had 98 people in my chat. It wasn’t long after that I had received my first tip from “ShyGuy25″.
The tip was for 100 tokens and he included a message asking if I could flash him my breasts. I was nervous. This was the first time I was going to bare my body for these guys. I sat up and could feel my heart racing. I reached up and slowly slid down one of the shoulder straps, and then the other. I put an arm in front of my nipples, just to give the guys a little bit more of a tease. ShyGuy25 tipped me another 25 tokens, and I knew it was time to be a brave girl. I lowered my arm and showed off my hard nipples. I could tell that my face was beet red!!
All of a sudden, there was a strange beeping noise coming from my laptop’s speaker. I didn’t know what it was and, to be honest, sort of freaked out trying to find it. I felt like such a klutz when I realized it was a private message from ShyGuy25.
“You are very beautiful” he said.
“Hehe thanks,” I replied, “I’m so nervous. This is my first time ever on this site”.
“I don’t believe you”
“I’m serious! I’ve never done anything like this before”
“Well,” he replied, “I would love to pop your private cherry”
“Hmmm, that sounds like fun.”
“When will you be ready?”
I sat there and thought about it for a second. I went and took another shot of tequila. As I was walking back to my bed, I passed by my mirror. I stood there for a second, admiring my body.
“You can do this Casey,” I thought to myself, “you’re gorgeous”
I laid back down in bed, took a deep breath, “I’m ready now sweetheart.”
It felt like hours until the notification popped up onto my computer screen. I clicked accept and before long, there was in a private chatroom with ShyGuy25.
“I’m so nervous,” I admitted, “how does this work?”
“Well, I can turn my webcam on,” he suggested, “and then we can just let loose and have some fun?”
“OK, that sounds great”
I expected to see a 40-year old heavyset man in front of me. I imagined that he was probably home from work, his wife and kids away for the day. I figured that his wife hadn’t pleased him in months, so he was on here to find an online companion.
But this wasn’t so. Not by any means. Sitting in front of me was an early 20′s man, with dark hair and green eyes. He had a defined chin and a five o’clock shadow. He was sitting at his desk without his shirt on, only blue gym shorts on. He wasn’t overly ripped, but I could tell that he was an active person.
“Oh, you are cute,” I said, trying to play it cool, “I guess it’s time for me to get naughty.”
I reached over to my bedside table and grabbed my dildo. It was bigger than any guy I had been with, and I wasn’t sure if i could actually take all of it. I sat it upright on the bed in front of me. I was on all fours, ready to start teasing ShyGuy25.
I started by running my tongue up and down the side of the shaft, keeping my eyes on the camera. When I reached the tip of the cock, I slowly ran my tongue all the way around it before taking the tip into my mouth. I gagged a little when I tried to take more of it into my mouth, laughing a little inside.
“Are you OK?” he asked.
“Ha Ha, yes. It’s just a little bigger than I used to.”
I sat up and spit onto the cock, getting it nice and lubed. I began to slowly stroke the dildo while making eye contact with the camera. I peeked down and saw that the bulge in ShyGuy25′s shorts was growing. I knew I was getting to him. I got back down onto all fours and put the cock into my mouth. This time, I was able to put most of the eight inches deep into my throat. I had never been able to deep throat a cock before, but my nerves were taking over at this point. I started to let out soft moans while taking more and more of my dildo into my mouth. I looked up and saw ShyGuy25 start to rub his shorts. I knew by now that his cock was craving to be freed. I reached behind me and slowly unhooked the clasp to my teddy. I slowly slid the straps down my shoulders, all this while still deep throating my dildo.
Out of the corner of my eye, I saw him start to slowly remove his shorts. His cock was just as big as my toy, if not bigger. He was at full mast now, his cock craving some much needed attention. I started to stroke my dildo while penetrating my mouth, this time with much more force. I watched as he started to play with his cock. He started out by just lightly rubbing against it, and then finally grasping his cock and slowly starting to stroke it. I wanted his cock in my mouth. I wanted his cock deep inside of me.
I turned around, still on all fours, and put my ass right in front of the camera. I knew that my g-string wasn’t covering much, but I didn’t care. Watching him stroke his cock while watching me was such a turn on. I didn’t have to put my hand in my panties to know that my pussy was wet, but I did anyways. I started out by grazing my sensitive clit, the panties blocking the view. I moved my hand even further down and slowly inserted a finger into my pussy. This was the most wet that I had ever been. I reached behind me and slid the panties to one side, baring all of my body for him to see. Looking back, I saw the head of his cock was covered in precum. He was turned on just as much as I was.
“Oh baby,” I said, “Are you ready to watch me get fucked?”
“Fuck yes I am”
I slid my panties down my waist, past my knees, and then completely off. I was completely nude for him now. I straddled my dildo and took a deep breath. I slowly lowered onto it. I thought that it would hurt when it first penetrated me, but it didn’t. It slid right in pussy. I bounced up and down the shaft, slowly at first and then picking up the pace. I started to moan louder now, fantasizing about him fucking me. My moans started to get louder as I fucked the dildo harder. I bent forward for him and spread my cheeks apart, showing him my tight little asshole. I raised a hand, looked back at the camera, and smacked my ass as hard as I could. I loved to be spanked.
“I love your ass baby,” he said, “Can you put a finger inside of it?”
I looked back at him and smiled, “I love fingers in my ass babe. Of course I will.”
I had never had so much as a finger in my ass before, but I didn’t want to tell him that. I raised my ass up into the air while laying my head and shoulders flat along my bed. I had one hand in between my legs holding my dildo, which was still deep inside of my wet pussy. I inserted a finger into my mouth and covered it with saliva. It went in easier than I thought it would, but I still grimaced as my finger went deep into my ass.
He was stroking his cock much faster now while arching his back, he was going to cum. I was fucking my dildo harder and faster than I had ever been fucked before. I could feel the wave coming over me, I was going to cum too.
“I’m about to cum baby,” I confessed, “I want your cum all over my ass.”
I heard him start to moan, and knew this his cock was about to blow.
“Yeah baby, cum for me,” I encouraged him.
I let out a loud moan as I felt the rush overcome me. I was cumming all over my dildo. My knees weakened and I fell forward, collapsing onto my stomach. I took a few seconds to collect myself and looked back at the computer screen. He had came as well, his chest covered in his creamy juices.
“That was amazing,” I said.
“I totally agree,” he said, “I may need a few minutes though.”
“A few minutes?” I asked.
“Yes,” he said, “Until round two.”
“Well,” I said smiling, “I’m ready when you are.”
“Hey gorgeous, I’m at the airport and on my way home. I should be there in about an hour,” I said into my cell phone as I flagged down a cab in front of the main terminal.
There was a soft laugh and then my girlfriend said, “Then look over your left shoulder. I’m on the second plane to the left and on my way to China.”
“You’re kidding me! I bust my ass to get home and they send you out? I’m not sure whose company is the worse, yours or mine.”
“Poor baby,” my girlfriend Shellie said. “I’ll have to see what I can do to make it up to you when I get back.” She paused a second and then added, “Or maybe I can make it up to you even sooner, since I left you a Christmas present at my apartment.”
“You know it’s always more fun to unwrap our gifts together,” I said as I got into the cab.
“That’s good since I’ve already partially unwrapped this present and left it tied to the wingback chair in my bedroom,” Shellie whispered. “You remember Casey, don’t you?”
“Casey? Redheaded Casey, as in your assistant, Casey?” I said with amazement in my voice.
“The one and the only,” Shellie replied with a laugh and then added, “You do know she’s a virgin, right?”
“Uh, no, I didn’t know that.”
“It’s oral only, I’m afraid. That is, unless you wouldn’t mind fucking that luscious ass of hers,” Shellie said and then made a soft whimpering sound. “Remember the first time you tied me up?”
I chuckled and said, “That is something I will never forget. You naked with nothing but a blindfold on tied to that old wooden chair. I’m not sure who was driving whom crazier. You with your arms tied behind the chair so your breasts stuck out. Your knees wide apart with that beautiful pussy of yours on perfect display. Your ankles tied to the outside of the chair legs.” I paused to sigh.
Shellie was silent for a few second and then whimpered softly. “I want to touch myself so bad.”
“What would you do if I set up the web cam so you could see what happens to Casey?”
There was a soft moan and then Shellie said, “I won’t be in Peking until tomorrow. It’s thirteen hours at the very least.”
“Then I’ll capture it to a file and send it along.”
Shellie laughed softly. “You were going to save it to a file anyway. You always do and did even that first time. I still get off watching myself.”
“No touching until the file gets to you and you had better start the web cam before you open it so I can watch you as you watch Casey.”
Shellie moaned and whispered, “Yes, Master.”
“Does Casey have any idea of what is going on and why isn’t she with you?” I asked sharply.
“She dyed her red hair with green streaks for Christmas and that wouldn’t go over too big in Peking, I’m afraid,” Shellie said and then was quiet.
“And?” I asked.
She whimpered softly and I could mentally see her squirming in her seat. “Well…. Uh…. You see…. She….”
“Out with it,” I commanded.
Shellie groaned and then whispered, “She found a couple of our home movies on my laptop a while back. Since then, she has been asking all kind of questions about the lifestyle and how things work. I always thought she was a submissive but now I know for sure. She got all excited when I told her she had to be punished for missing this trip and making more work for me.”
“Then you should wait until you get back and Top your own sub,” I told her.
There was soft whimpering moan on the other end of the call. “I wanted to but I didn’t have the time. Plus I was kind of testing her out to see if she really wanted what she thought she wanted. I had her strip and then put her in my dark green corset and laced it up. She got so wet.”
“And you got even wetter,” I said.
“Yes, Master. Wet enough that I had to change panties before I left for the airport. Tying her to the chair was very exciting for both of us. That was as far as I was going to go and started to untie her. She looked so disappointed and unhappy, so I retied her and told her you would be home soon.”
“And what did she say to that?”
Totally out of character, Shellie giggled. “Not much, I had the stick gag in her mouth. Her eyes got big but she didn’t shake her head or fight the ropes.”
“What if I hadn’t come home tonight?” I asked.
“I called your office to see when you would be home. They said you were in the air as we spoke.”
“I definitely see a spanking in your near future when you get home,” I said softly.
“Yes, Master. If you please, Master,” Shellie whispered demurely.
“So, lets see if I have this straight. You’ve left an untested, unknown sub, naked except for a corset, bound and gagged in a chair in your apartment while you fly to China. And now you expect me to give her what she wants, without so much as talking to her.”
“Yes, Master,” Shellie, whispered.
“This should be very interesting and could go very well or very bad. Maybe I should just untie her and postpone things until you get back. That way I could start her off by letting her watch you get a spanking.”
Shellie whimpered softly and said, “Yes, Master. Please.”
I had to take the phone away from my ear as I tried to hold back a chuckle. Shellie came hard from being spanked over my knee and she would come even harder with Casey watching. She had strong exhibitionist tendencies but was afraid to let them out except when we were out of town together, which was seldom.
Putting the phone back to my ear, I said, “We will see how things go when I get to your place. I’ll have to play it by ear. Either way, I will call you later.”
“Yes, Master, I love you.”
I grinned as I replied, “I love you also. So be careful over there.”
“I will,” Shellie whispered and broke the connection.
I dropped my phone in my coat pocket and tapped on the glass between the front seat and the back. A few seconds later the cabbie asked on the intercom, “Yes, sir?”
“A slight change in plans,” I said and gave him the address of Shellie’s apartment building.
I went over what I knew of Casey in my mind as I rode the elevator up to the twenty second floor. Petite and slender with small breasts and a nice ass from what I had gathered from Shellie and from what I had seen of her in business suits. She was shy and retiring for the most part, blending in with the background except when she was needed.
She had to be in her mid to late twenties. She was a college graduate in business and stayed on top of things where her work was concerned. I knew little about her other than that. That she was a virgin was interesting but not unheard of in these days. Shellie had mentioned anal, which made me wonder.
I took out my cell phone and called Shellie. She answered on the second ring and I asked, “Which of our movies did she watch and did she just watch and nothing else.”
“She watched the one of my first time and she was masturbating as she did,” Shellie whispered. “I caught her in the middle of things and that pushed her over the edge into a monster of an orgasm.”
“What do you know about her and anal, since you mentioned my fucking her ass.”
Shellie whimpered softly. She loved a dick up her ass after a spanking while her ass was all hot and red. “She had a finger fucking her ass while she rubbed her clit like mad and she jammed the finger deeper when she came,” Shellie reported.
“I’m in the elevator and I should be at your apartment in a few minutes,” I told her. “I’ll call you later.”
“I’m so horny,” Shellie whispered.
“It serves you right for making this mess and not being around to fix it,” I said and then added, “Anticipation makes all things better. Just think how hard you will come on cam for me when you get to the hotel.”
Shellie groaned with a mixed note of frustration and anticipation in her voice. I closed the call with a smile on my face as I pictured her squirming in her seat. I wondered who was sitting next to her and if they had heard any of the conversation. That also would keep Shellie on a razor edge.
The elevator stopped and the door opened. I rolled my suitcase out and headed down the hall toward Shellie’s apartment. The hard-on in the front of my pants showed I was anticipating things to come myself.
I walked across the living room and down the hall with slow measured steps. As I passed Shellie’s bedroom I glanced to my left, took two more steps, and stopped. Casey was magnificent the way she was tied to that old wingback chair. I straightened my suitcase and stood it up before I removed my laptop.
Taking two steps back, I stopped centered in the bedroom door, my eyes exploring Casey’s lush little body with leisure. Her hands were tied high over the back of the chair which lifted her small cones shaped breasts even more than the corset and thrust them forward. Her knees were over each arm of the chair, her ankles tied to the back and the front leg. Shellie had done a masterful job.
Casey shiver as I looked at her breasts and then try to close her knees as my eyes centered on her sex and the little puff of fine carrot red hair on her mound. I licked my lips and asked, “Now what do we have here? A snack after a long flight or maybe a Christmas present from Shellie.”
Casey’s eyes got big and she squirmed in the chair, not pulling at the ropes as much as moving from uncertainty and anxiety. I smiled as I moved to Shellie’s makeup table and placed my laptop on it. I spent several minutes getting it set up and recording.
When I turned around and walked back over to the door, Casey’s eyes were flicking back and forth between the laptop and me. “Yes, it is on and yes, you are being recorded in all your glory. And yes, I will send it to Shellie as soon as she lands in China.”
Casey made a soft muffled whimpering moaning sound and squirmed even more than before. “Do you like that idea?” I asked.
She looked at me for a moment and then shook her head slightly and then nodded quickly.
“Nod your head for yes, shake your head for no, and shrug your shoulders if you don’t know. Nodding your head and then shaking it means yes and no.” I told her. She nodded and then shook her head.
“You watched the movie of her first time tied up, why shouldn’t she see yours. Maybe she will masturbate to it like you did hers.” Casey’s eyes got big at my last statement.
“Ok, you think about it while I go change clothes and mix myself a drink. Then we will see what we have here.”
She made the whimpering moaning sound again as I walked out the door.
I returned to the bedroom wearing a pair of soft cotton shorts and a t-shirt. I had a glass with three fingers of bourbon over ice in one hand and a glass of water with a straw in the other. I sipped my bourbon as I let my eyes wander over her exposed body again. She did not shiver or squirm, her eyes were on the glass of water.
I sat my drink down and walked over to stand in front of her. I held the glass out in front of her as though she should take it from me. She looked up at me and then back down at the glass of water.
“Power and control, that is the name of this game,” I said softly. “I have the power and control, you have none. I am the master and you are the submissive.” I paused a second and asked, “Are you a submissive? Shellie said she explained the term.”
Casey shrugged her shoulders a few seconds later. “I think you are and Shellie said she knew you were, so the only one who doesn’t know is you. In any case, I don’t know of many dominate types that would allow someone to strip them naked, put them in a corset, and then allow themselves to be tied up like you are.”
Casey’s eyes kept going to the water. “Yes, I know, you’re thirsty but there are a few rules you must learn first. I am to be called Master or Sir; Shellie is to be called Mistress, if she decides she wants to Top. You remain silent unless asked a direct question or you feel the need to use your safe word.” I paused a moment and asked, “Do you have a safe word?”
Casey shook her head and I sighed deeply. “That’s two spankings Shellie has coming. The first for leaving you here alone and the second for not giving you a safe word.”
I sat the glass of water on the side table and reached forward with both hands to remove the dog bone shaped gag. “Hold you head in place while I remove this.” I told her. She pulled her head back and the gag came free enough for me to slip it down around her neck.
Casey worked her mouth for a moment as I noted the thin lines of drool at each corner of her mouth running down on each side of her chin. “Shellie choose an interesting gag for your first time. Normally a ball gag is better on first timers, it doesn’t strain the jaw as much.”
When Casey licked her lips, I retrieved the water and stuck the straw in her mouth. Her eyes were on mine as she sucked the water down. After the third long pull, I took the straw away from her. “Too much water and you will have to pee. Peeing in the position you are in is tricky and very messy.”
“I…. Uh…. I….” She stammered for a moment and then leaned her head back and closed her eyes. “I think I’ve made a big mistake.”
“The only mistakes were made by Shellie and she will be punished for both of them.” I paused a moment and looked at Casey. If she was having doubts then…. “Ok, I’m calling a time out.”
Casey opened her eyes and looked at me as a grin slowly spread across her lips. “I’ve heard of standing in a corner or sitting in a corner for a time out but this position leaves something to be desired.”
“Left to yourself you can’t get in any trouble like you are, as you found out when Shellie left,” I reminded her.
She shivered and then whimpered softly. “When she was tying my feet, her head was only a few inches from my sex several times. I’ve never been with another woman but….” She left the sentence hanging as she whimpered softly.
I went and got the chair from the vanity table and sat down in it in front of Casey but over enough so I did not block the camera. I let my eyes wander over her lovely body openly. After a minute or so, she squirmed and whimpered.
“Do you like to be looked at?” I asked.
“I…. Uh…. I….” She stammered and then she nodded her head. “I like the way you look at me and the way Shellie looked at me. Both make me wet and horny. I feel so helpless the way I’m sitting and I can’t cover up. Normally, I don’t like to be looked at even when I have my clothes on. I’ve always been shy.”
“It is the same reason why Shellie being so close to your pussy made you want her to lick you. You were not in control and could not stop her if she did. Giving up control means you can do things and have things done to you without the normal guilt associated with those things. All you have to worry about is enjoying what you do and what is done to you.”
Casey squirmed and flexed her hips. “I…. Uh…. I….” She stammered and then moaned softly as her hips flexed even harder.
“Are you on the edge of an orgasm?” I asked sharply. Casey moaned loudly and nodded hard and fast. I leaned forward and ran my tongue along her inner thigh. Halfway to her pussy, she gave a soft yell and bucked her hips up hard several times. I could see the opening to her vagina opening and closing as a few drops of lubricant rolled down into the crack of her ass.
I chuckled and sat back in my chair. “Your first orgasm tied to a chair,” I whispered. “When you get your breath back, tell me how it was to come with no one touching your pussy.”
Casey groaned and flexed her hips hard several times. “Is that a second or is the first one still going on?”
“I…. I…. I can’t…. stop,” she said loudly as her hips continued to flex and jerk.
A smile was on my face as I sat there watching her. It was several minutes before her hips stopped moving. “I take it you have never come that hard or long before,” I said as Casey got her breathing under control somewhat.
“Never. Nothing like that, before,” she said and groaned softly.
“The brain is the biggest sex organ in the body and if you feed it little tidbits like I was doing to you then wonderful things can happen.” I told her.
“You sure hit the right buttons,” she whispered a moment later.
“That’s my job as the dominant one or at least one of them. Normally, I would have told you to hold it back for as long as possible but in this case, letting it go was best for you. I have to know you and your limits as deeply as you know them and sometimes I have to know even more than you do.”
“Hold it back?” Casey asked.
“If you hold it back, it builds in strength and intensity. If you can get to the point where you are right on the ragged edge and can stay there, some say it is even better than having an orgasm.”
Casey moaned and flexed her hips. “If that orgasm had been anymore intense, I would have exploded.”
I chuckled and stood up. “Little One, you haven’t felt anything yet.”
Casey’s eyes were on mine and then they grew wide as they dropped down to the tent in the front of my shorts. “I…. I…. I….” She stammered.
“That is something you need to stop. You can say anything to me or Shellie that you can think of. Is that understood?”
She nodded and then whispered, “I was going to remind you I am a virgin.”
“I know you are a virgin and that you want to stay that way but that doesn’t mean I can’t stick my dick down your throat or up that beautiful virgin ass of yours.”
Casey’s eyes got wide and her mouth worked but nothing came out. I grinned and said, “I take it those ideas hadn’t crossed your mind yet.”
Casey shook her head quickly and whispered, “No, they hadn’t and the fact that I can’t do anything to prevent either just hit me.”
“Do you remember that red butt plug I put up Shellie’s marvelous ass her first time tied to a chair?”
Casey nodded sharply and then moaned long and loud.
“Are you coming again?” I asked sharply.
She shook her head. “Not yet but it’s getting close. That’s the part Shellie caught me watching.”
“You mean, she caught you masturbating to that part,” I corrected.
Casey moaned and flexed her hips. When I gave her a light slap on the inside of her left thigh, her hips flexed even harder. A slightly harder slap to the inside of her right thigh had her hips jerking and bucking as she gave a soft yell and pulled her butt off the towel she was sitting on, with her arms.
“How long has it been since you’ve had sex with someone else?” I asked a few moments later. Casey yelled again and then went limp.
“I think you’ve had too much of a good thing,” I whispered as I set about untying the unconscious woman in the chair.
I carried Casey over to Shellie’s bed and laid her down on her stomach. Her breathing was still a little fast, as was her heart rate. I went over to the vanity and opened the lower left hand drawer. I took out a set of padded handcuffs and a small black butt plug. I moved the laptop so the camera now covered the bed.
The cuffs went on Casey’s wrists with them behind her. The small butt plug was in my mouth. Casey moaned as I slipped my left arm under her hips and lifted her ass up in the air. Her anus was a dark shade of pink. Not a good sign for anal play in my experience. The darker brown the better, is what I had found over the years, although there are exceptions to every rule.
Shellie had said Casey was fingering her ass so now was the time to test the waters, so to speak. The butt plug was slick with my spit as I pressed it to her asshole. It slipped in half way with ease and then moved slowly a little more. Casey whimpered loudly and flexed her hips. The butt plug went home suddenly.
Casey kept flexing her hips slowly as I lowered her back to the bed. I checked her breathing and heart rate, they were almost normal. I pulled the comforter up over her, got my drink, switched off the camera in the laptop, and went to the living room.
I was dozing in the recliner when Casey came in the room. I woke up to her loudly asking, “What the hell did you stick up my ass and why won’t it come out?”
It took me a moment to focus and then I grinned. “It’s a butt plug similar to the one I put in Shellie’s ass and your ass doesn’t want to let go of it, would be my guess on the second part of your question.”
I sat up in the chair as she asked sharply, “Why are my hands tied behind my back?”
She made a squawking sound as I grabbed her around the waist and pulled her down across my lap. My left arm held her upper body as my right hand landed solidly on her naked upturned ass. The spanking was short with moderate pressure and a cupped hand. It was more sound than fury but her ass was warm and very red by the time I stopped.
She was crying softly but her ass flexed and jerked as I rubbed the heat into her firmly. “I am the Master and you don’t ever use that tone of voice with me. Is that understood?”
Casey nodded slowly, her crying down to a soft whimper as I rubbed her ass. When I tapped the base of the butt plug her ass jerked and she moaned. “The time out is over, so from now on it is Yes, Master or No, Master and all requests are to be made with a Please or Sir at the beginning or the end. Do you understand that?”
Casey nodded and my hand landed solidly on her ass. She gave a sharp yell and quickly said, “Yes, Master!”
“That is much better,” I replied as I went back to rubbing her ass lightly.
She shivered and pushed her ass up to make firmer contact with my hand. “I’ve…. I’ve never been spanked before,” she whispered.
“Can you feel the heat and how wet your pussy is?” I asked softly.
“Yes….” She said with a hissing sound in her voice and then she quickly added, “Yes, Master.”
I turned my hand and pushed it between her upper thighs to cup her sex. She whimpered loudly as her legs opened wider. Her outer lips were slippery and my middle finger slipped between them easily. “You are very wet,” I said as I ran my finger up and down her slit.
Casey’s hips flexed as I moved my finger and then jerked as I touched her clit. She took in a sharp breath and then moaned as I continued to roll her clit around. A few moments later, her hips jerked again and I took my hand out from between her legs. She made a whimpering moaning sound of frustration, when I did.
I chuckled and patted her ass firmly. “You are a very greedy girl,” I told her. “Two huge orgasms with no one touching your pussy and now you want one with me touching you.” I paused to tap the butt plug again. “Your hands are behind your back to keep them out of your pussy.”
She moaned loudly when I tapped the butt plug. “Hold onto your orgasm and keep it in,” I told her as I tapped the butt plug again.
Her moan was softer but her ass flexed slightly. I tapped the plug again and remembered the laptop. Shellie would be mad if she missed too much. “Ok, off my lap while I go get the laptop. Shellie will want to see what is going on,” I reminded her.
Casey shivered as she raised her upper body and sat back on her heels. I stood up and turned so the tent in my shorts was right in front of her. I rubbed the soft material with my hard dick under it against her face. She whimpered softly but held still as I did.
“What would happen if these were Shellie’s panties, if she had any on, that is?” I asked her softly.
She moaned loudly and shivered hard, “I would probably come my brains out,” she whispered and then glanced up at my face as she added, “Master.”
“You’re going to have to do better than that, unless you really want another spanking,” I said as I stopped rubbing her face and stepped back.
Casey looked at the floor and whispered, “Yes, Master.”
I grinned. She was a submissive all right. “Is that yes for doing better or for another spanking?”
“For doing better, Master.” She replied quickly.
“So, you don’t like my spankings. Is that what you are saying?” I asked sharply.
“I…. Uh…. I….” Casey stammered as she tried to figure out the best way to answer and not get another spanking. Finally, she said, “I’m not sure I’m ready for another spanking yet, Master.”
I chuckled at her tact and honesty. “Stay where you are. I will be right back.” I went to get the laptop.
Returning, I set it up on a small table and turned on the camera. Once it was recording, I walked over to Casey and said, “Shellie is going to be annoyed when she finds out she missed your first spanking.”
Casey glanced at the laptop and then up at me for a second before she looked back down. Smiling I said, “Walk on your knees over to the coffee table and lay down across it.”
Without a word, Casey did as she was told. Once she was draped across the table, I walked over and turned the laptop camera her way. “This should give Shellie an idea of how red your ass is and how wet your little pussy got. Not to mention how pretty your ass looks with a butt plug shoved up it.”
Casey shivered and then whimpered softly.
“Spread your knees farther apart, let her get a good look at your sex,” I said and grinned as she moved her knees a few inches out in either direction.
I stepped forward and slapped her ass hard. She jumped and then spread her knees even wider. “Much better,” I told her as I rubbed the handprint on her right ass cheek.
When I bumped the butt plug, Casey flexed her hips. I put two fingers on the end of it and rocked it up and down. She whimpered and flexed her hips. She had a very sensitive asshole it seemed. “Does that feel good?” I asked as I continued to move the plug around.
“Yes, Master,” she whispered.
“How do you think it would feel if I fucked your ass with it?”
“Master, I don’t know. It would probably feel good if it didn’t hurt.”
I went to the bedroom and returned a minute later with a bottle of lube and a long tapered dildo that had balls along its length that got bigger from the tip up. “Did it hurt when I put it in?” I asked.
“I don’t remember, Master,” she said softly.
“Then I will have to take it out, apply some lube to it, and see if it hurts going back in,” I said as I laid the long dildo down on the coffee table so she could see it.
Casey whimpered as she saw the long dildo and then she moaned loudly as I tapped on the butt plug sharply. She moaned even louder as I pulled it slowly out of her ass. I squirted lube on it and slowly pushed it back in. She groaned loudly and flexed her hips when it was fully seated.
“Did that hurt?”
“No, Master, it felt good.”
I pulled it out again and then pushed it back in. Her hips flexed as it locked into place. I slowly fucked her ass with the butt plug until her hips quivered. Then I asked, “So you do like having your ass fucked with the butt plug?”
“Oh yes, Master. It feels even better than my finger ever felt.”
“In that case, are you ready to try something else?”
Her eyes had been closed until I asked that question. They popped open and grew wide as she looked at the long dildo. She chewed her lip a second and then nodded her head and just as quickly shook it.
I chuckled and slowly pulled the butt plug from her asshole. I laid it next to the dildo and let her look at both. A minute later she groaned and whispered, “Yes, Master.”
“Now that wasn’t so hard, now was it?” I said as I picked up the dildo and applied the lube to it.
Her ass flexed in anticipation, as she said, “No, Sir.”
I let her wait a moment or two and then pressed the first ball against her asshole. She jerked as it entered easily, as did the second. The third ball was slightly larger than the butt plug and slowly slipped inside as I held a light pressure on it. Casey groaned and wiggled her ass hard. The fourth ball disappeared before I could stop it.
Her ass was flexing up and down and she lifted her arms up and down several times, as her ass moved. “I take it you like this even better than the butt plug.”
“I…. I feel…. Feel so full… and tingly,” she whispered as her hips kept moving. She had forgotten all about Master with the dildo up her ass.
I pulled the dildo out of her ass slowly and laid it on the table. She whimpered and moaned as I did and then her ass moved up and down and around in a circle as if it was hunting for the dildo. “It’s on the table,” I said.
Her eyes jerked open and she said, “But… but,” as she saw the dildo lying next to the butt plug again.
I slapped her hard on one ass cheek and then the other. “What did you forget?” I asked her and swatted her ass twice more.
She flexed her hips hard and almost yelled, “Master!”
“Thank you,” I said and rubbed the handprints on her ass cheeks. Her hips moved slowly up and down as I did.
I reached over and picked up the dildo, swapped hands with it, rubbed her ass with my left hand, as I pressed the small ball against her asshole. It went in slowly to the third ball and I held it there letting the fourth ball ride against the tight ring of muscles as her ass flex up and down.
When she gave a little moan of frustration, I pushed the fourth ball home and started to fuck her ass with the third and fourth ball. She shivered and flexed her hips faster. I slapped one ass cheek and then the other. “Be still and let me do the work.”
She moaned loudly and answered, “Yes, Master,” as her hips stopped moving. “I’ll try to be still but….” The rest of the sentence was lost to a long drawn out moaning groan as she started to come and come hard. Her ass was jumping and jerking.
I continued to fuck her ass and at one point pushed the fifth and last ball up her ass. She had almost stopped jerking but when that last ball entered her, she started all over again. I let go of the dildo, sat back on my heels, and watched her ass jerk and buck.
At one point, I turned to the camera and grinned. “She reminds me of someone else we both know,” I said.
A few minutes later, Casey was down to an occasional twitch and whimper. When I reached over and patted the end of the dildo, she gave a jerk and groaned. “It’s still in there,” she whispered in disbelief a few seconds later and flexed her hips rapidly up and down.
“It’s all in there,” I said and then patted the handle of the dildo again.
She groaned again and wiggled her ass. A moment later, she giggled uncharacteristically and whispered, “I can’t believe I ate the whole thing.”
“Horns, hooves, tail and all,” I said with a grin.
Casey giggled again and then sighed deeply. “Master, can I just sleep here? I don’t think I have the energy to move anywhere else.”
“How about supper?” I asked.
She giggled again and whispered, “I’m too full to even think about food, Master. My mind is too focused on my ass at the moment.”
I went to the bedroom and found the keys to the handcuffs. When I took them off her wrists, the first thing she did was to reach down and feel the end of the dildo. She used a fingertip to trace the point here the handle stretched her anus.
Looking over her shoulder at me, she asked, “Master, what is keeping it in?”
“The muscles are in a ring at the opening. The largest ball is inside that ring and there is not enough force to snap it back past that point,” I explained.
She felt of the taught skin again and slowly came up on her knees. She slowly worked her hips from side to side and then back and forth. She whimpered softly several times and then asked, “Will it fall out?”
“As tight as your ass is, I doubt it. Go ahead and stand up slowly but remember it is back there and don’t sit down or it might get a little hard to retrieve,” I told her with a grin.
She shivered. “It’s a little hard to forget, believe me,” she said and used the coffee table for support as she slowly stood up. Her ass was pointed directly at the camera, so I knew Shellie would get a great view of it, as she had all of the events earlier.
Standing, Casey wiggled her hips and then rotated them. She took a deep breath and turned around slowly. “Not too bad,” she whispered and then she took a short step. The second step was longer and she shivered. She bent slightly forward and slowly walked around the room.
She was quivering by the time she stopped. “I…. I think…. I could come just walking around,” she said breathily.
I took a few steps back and said, “Straighten up and walk to me as you normally would.”
She straightened up and took a deep breath. She took the four steps with her normal stride and speed. Her eyes got wide and her mouth opened. I held onto her arms as she tottered back and forth. “Oh! Oh, my….” She whispered softly.
“Wait until you try it with high heels on. It changes the angle completely and from what Shellie says, it’s mind blowing.”
Casey groaned and whispered, “I can hardly wait.”
I laughed and replied, “Ok. As for now, just relax and let your body get used to the idea of something up your ass and moving as you do. Remember to sit on the side of your ass and not flat down on it.”
“Yes, Master,” she whispered as she straightened up again.
“The scene is over,” I told her and then added, “I will need to get you a collar if you come back for seconds. Putting it on starts the scene and taking it off ends things.”
“A collar? You mean like the choker Shellie wears now but didn’t a year ago?”
“Yes, something like that,” I replied. “She wears hers all the time as an honor to me and to tell others in the lifestyle who and what she is.”
Casey looked at me hard for a moment and then smiled as she came up on her toes and brushed her lips gently against mine. When she dropped down off her toes she gasped and flexed her hips. She chuckled and shook her head. “That was a jolt.”
“Do you want me to remove it?”
She laughed and shook her head. “I feel like I’d fly around the room backwards, if you did, at the moment.”
I walked over, turned the camera off, and then shut down the laptop. Looking over my shoulder at Casey, I asked, “Are you staying here or going home?”
“I hadn’t thought about it, I’ve been a little tied up,” she said with a grin.
“If you take off with Shellie’s favorite toy still stuck up your ass, she is not going to be happy.”
Casey looked at me and tilted her head to the side. “Mad enough to give me a licking, I mean, spanking?” she asked softly.
I laughed and nodded my head. “Something like that.”
She walked around the coffee table and lay down on the couch on her stomach. She wiggled and then pulled a throw pillow down and stuffed it under her hips. Her ass was now angled up and elevated enough so the handle of the dildo showed barely above her ass cheeks.
She crossed her arms under her head and asked, “Are you going to turn the camera back on when you remove the toy?”
Her eyes jumped to the tent in the front of my shorts. “Are you going to fuck my ass when you do?”
“Do you think I should?”
She stifled a soft moan and nodded slowly. A moment later, she pushed her hands over toward the end of the couch and closed her legs tightly with her toes pointed at the opposite end of the couch.
I grinned and said, “You want to be tied down with your legs together when I do.”
She nodded and then flexed her hips. “That’s my biggest fantasy,” she whispered as her hips moved harder and faster.
“Hold it in,” I told her. “Let it build and build.”
She groaned and froze, holding her hips still except for a quivering at the backs of her thighs. Slowly she relaxed and then sighed.
“Good girl,” I said with a smile.
She opened her eyes and gave me a shy smile back.
I sat in the reclining chair and watched Casey on the couch as I finished my watered down drink from earlier. It was not long before she dozed off and I wasn’t far behind her.
My phone buzzing woke me up. I picked it up off the table next to me and said, “Hello?”
“I’ve had two meals, three drinks, and a nap and I’m still four hours from China,” Shellie said softly.
“And you are about to go crazy with curiosity.”
“That also,” Shellie whispered and then added, “I need to change my panties again worse than I did before I left.”
“Go to the restroom, take off your panties, hang them on the hook on the door, wash yourself and then return to your seat and call me back,” I said in a soft but commanding voice.
“But… but….” Shellie started to protest.
“Speaking of butts, you already have two spankings coming and now it could be three. Casey has already had one and a few disciplinary swats. Right now, she is asleep on the couch on her stomach, with a pillow under her hips and your favorite anal toy stuff up her beautiful ass,” I said and then waited.
Shellie whimpered softly and then groaned as I spoke. When I finished there was silence, and then she whispered, “I’ll call you back, my panties are now an even bigger mess and my neighbor is looking at me funny.” The line went dead.
Casey stirred on the couch and opened one eye. Seeing me looking at her with my phone in my hand, she smiled and asked, “Is that Shellie?”
“It was but she had to hang up and go take her panties off.”
Casey looked confused and shook her head. “Huh?”
“Time, anticipation, and a good imagination had her panties as wet as they were before she left here. A few details and I think she came sitting in her seat on the airplane,” I explained.
Casey laughed and shook her head. “Miss Prim and Proper came in public. I would have loved to be a fly on that wall.”
“It’s not the first time, nor will it be the last,” I said with a grin.
Casey looked thoughtful for a moment and then laughed again. “That explains a lot, believe me.”
My phone buzzed and ended whatever else Case was going to say. “Hello?” I said into the phone.
“I’m back sans panties, a little cleaner, a lot cooler, and still horny as hell,” Shellie whispered on the other end of the line.
“Shellie sends her regards,” I said to Casey.
“Hey, Shellie,” Casey called out.
Shellie groaned on the far end of the line and asked, “Is she still laying the same way on the couch?’
“Yes, she is, shall I turn on the camera for a few minutes?”
“She can’t be in China yet,” Casey said as I stood up.
Shellie said, “Please, Master.”
And to Casey I said, “For later.”
“Later than what?” Shellie asked in confusion.
“I told Casey my turning on the camera was for you later, when you land.”
“Have you fucked her ass, yet?” Shellie asked in a whimpering whisper.
“Not yet, we fell asleep.”
“Are you going too?” she asked in the same sort of voice.
“She asked me the same question not too long ago and I’ll ask you what I asked her, “Do you think I should?”
Shellie moaned loudly and then whispered with a hiss in her voice, “Yes, and I want you to fuck my ass when I get home with us watching you fucking her ass.”
“You are going to shock your neighbor again talking like that,” I cautioned her.
“He went to the bar or at least I hope that’s where he went and not the bathroom,” she whispered and then laughed.
“Either way, he’ll have a stiff one,” I said with a laugh of my own. Shellie laughed along with me.
When she quieted down, I said, “Ok, hang up the phone and call me when you land.”
“Yes, Master,” she whispered and then made a kissing sound just before the line went dead.
I closed the phone and looked at Casey. “She will call again when she lands.”
Casey pushed up onto her hands and knees and then stretched forward and back like a very large cat. Then she put one foot on the floor and stretched again with her ass angled more toward the camera.
“Play to the camera girl,” I said and chuckled.
She arched her back and then dipped it low as she moved the other knee to the floor. Her ass was now pointed directly at the camera. She flexed her hips up and down as she watched herself on the laptop screen. She spread her knees wider, arched her back lower and did it again.
With a shiver she said, “I’ve never done anything even remotely like this and damn, I look sexy and wild.”
“Shellie will go nuts watching you do that with her toy up your ass. She knows exactly what it feels like and there will be mental transference.”
Casey looked at the front of my shorts. The tent was back from watching her. “Can I have my ass fucked now Master. Please,” she whispered softly.
I stood up and took my shorts off. Casey moaned softly as my hard dick came into view, her ass bobbing up and down at the same time. “I’ve…. I’ve never wanted anything so bad in my life,” she whispered.
“In that case, why don’t you crawl into the bedroom like a big sensuous pussy cat while I follow you with the camera. Then I can tie you to the bed.”
Casey shivered and turned to get down on her hands and knees. She crawled around the coffee table and made a snarling face at the camera as she passed it. With a smile, I picked up the laptop and followed her down the hall. Her ass swayed from side to side as she crawled. The handle on the dildo looked like a short stubby tail.
She crawled over by the bed and lay down on her side on the fuzzy rug next to it. I put the laptop on the Vanity and went across the room and got a hard wedge shaped pillow out of the corner. I placed it in the center of the bed and went back to the vanity for a pair of leather cuffs and a handful of straps.
“Up on the bed and on the pillow with your ass this way,” I told Casey.
She snarled at me and climbed on the bed. She was playing the big cat to the hilt and having fun with it. I wondered if I had hit another one of her fantasies but that was for later. Right now, I had much more interesting things to do.
I put a cuff on each of her wrists and then ran a strap from each of those to the slats in the headboard. Three shorter straps, one around her upper thighs, one just above her knees, and one around her ankles, held her legs together. I clipped a strap to each side of the one around her ankles and ran those to the corners of the bed.
“So far so good?” I asked as I pulled the ones at her feet tighter. She nodded and wiggled her ass from side to side.
I added one more strap around her waist and ran a strap off it to each side of the bed. Tying those off to the bed rail, I pulled them tight. Casey wiggled again but could only move a little. When I pulled her arms tight above her head she moaned softly and tried to wiggle. She could but it took effort against the dense foam.
“One more thing and we are good to go,” I told her.
I moved the laptop to the side of the bed so Casey could see it. Then I strapped a remote camera to a stand and positioned it near the left corner of the bed, high up, and pointed directly at her ass. I plugged the lead into the laptop and switched views.
Casey gasped as her ass came into view with the dildo handle sticking out of it. Then she moaned softly. “I can watch as you fuck my ass,” she said in a trembling voice.
“You can watch, I can watch, and later, Shellie can watch.”
Casey shivered hard and tried to flex her hips. I smiled as I reached over and patted her ass firmly. “Shellie likes her ass fucked after a hard spanking while it is still hot and red,” I said softly. Casey groaned loudly.
“She has spankings coming when she gets home and wants me to fuck her ass while she watches me fuck yours. I wonder what she would do if she knew I was going to strap her down this same way and let you watch from the corner of the bed.”
Casey groaned even louder as her ass twitched and barely moved. Her mind was working on her big time. I wondered if she would come when I removed the dildo from her tight ass. With a grin, I reached for it; there was no time like the present to find out.
I pushed in on the handle a quarter inch and then let go. Casey gasped and then whimpered as the last ball eased back to where it had started. I did this several times with the same results. The next time, I pulled the largest ball out of her ass after pushing it in. She gasped even louder and then moaned softly as I pressed it against the tight ring of muscles for a moment.
Easing the fourth ball out and then the third was easy. I held the toy still and watched her asshole contract around the shaft below the third ball. When it did, I slowly fucked her with the third and fourth ball.
Casey groaned loudly and tried to flex her hips. I slapped her ass cheek and said, “Lie still.” She groaned even louder in frustration. She wanted to be fucked harder and faster.
A minute or so later, she whispered, “Please, please, please,” rapidly.
I smiled as I rammed the dildo into her ass all the way to and including the fifth ball. She let out a soft yell of surprise and then groaned long and loud. I could see the opening to her vagina pulsing. “Are you coming?” I asked softly.
When she did not reply, I slapped her ass hard enough to leave a red handprint. She yelled again and shook her head. “No Master, but I am very close,” she said in a very tense, quivering voice.
“Good,” I said as I turned away and went to get the lube.
When I returned, I lowered the camera and centered it on Casey’s sex and asshole. I also moved a light over closer to the end of the bed. Casey shivered at the new view and then moaned softly. “I have a handprint on my ass.”
“It is only temporary I assure you. If you like it, it will have to be reapplied regularly.” She shivered and moaned again.
I removed the dildo as I had earlier and ended up fucking her asshole with the number three and four balls as she watched. She whimpered and moaned the whole time but remained as relaxed as she could the whole time. When she started to tense up, I removed the dildo and went to the bathroom to wash it off and left it there.
When I returned, Casey was staring at the screen intently. “What is so interesting?” I asked her.
“My…. My asshole was, uh, open and then it slowly closed. I… uh….” She whispered and then she saw me lubing up my dick out of the corner of her eye and moaned long and loud.
With a grin, I climbed up on the foot of the bed and straddled her hips. I pushed my dick down and bent my knees until the spongy head touched her anus. Casey gasped; her eyes were wide as she watched the laptop screen. I rubbed the head firmly over her neither opening but did not push it in.
“It’s…. It’s so warm,” she whispered in a trembling voice.
Then she groaned long and loud as I pushed down and slowly sank my dick in her tight hot asshole. When my hips touched her ass cheeks, her asshole grabbed me tightly as she gave a loud yell. She was coming as I started to slowly fuck her ass. My dick was a little longer than the toy and close to as big around as the fourth ball, so it moved easily in her ass.
Her ass grew hotter and tighter as her orgasm peaked. A few moments later, it began a pulsing, grab and release along my shaft. I continued to slowly fuck her with full deep strokes. Ever so many strokes I would pause with my dick fully planted, and whisper, “You have a dick completely in your asshole.”
Each time I did, Casey would yell softly and her inner muscles would grab me tightly. I wasn’t sure if those were small orgasms or just realizations in her mind causing the reaction. Over the next few minutes, I sped up the strokes and drove in harder to spank her ass with my hips.
Casey was now moaning almost continuously. At one point, her eyes snapped open, she stared at the screen for a moment and the she yelled, “Harder,” and closed her eyes again. She gasped loudly and went back to moaning even louder as I slammed into her ass even harder on the next stroke.
My orgasm was building fast now but I tried to hold it off to see if she would come again. I need not have worried, as a few minutes later she gave out with the longest and loudest yell yet. Her asshole was now trying to crush me. That put me over the edge and I came as I planted my dick as deep as it would go and held onto her hips.
Casey seemed to be out of it again as I slowly climbed down off the bed. I stood by the end of the bed and watched as her asshole slowly closed. There was a wet streak from her vagina leading all the way down to her clit. For Shellie’s benefit, I said, “She has an asshole full of cum and her pussy is wet enough to rival yours.”
From the bed, Casey mumbled, “Yes daddy, I’ll be a good girl.”
I gave her a hard look and went to switch the camera and laptop off. I had an idea that I had stumbled onto something that Casey did not even remember herself, or maybe she was just having a dream. Only time would tell.
With a shake of my head, I headed for the bathroom for a shower.
I checked on Casey after my shower. She was snoring softly. I decided to let her sleep until Shellie called from the airport. I went to make some breakfast, as I was suddenly ravenous.
I had finished breakfast and was doing some editing on the video file, cutting out some time lapses, as I sipped on my third cup of coffee. My phone buzzed and I picked it up and said, “Hello?”
“I’ve just cleared customs and I’ll be at the hotel in an hour,” Shellie said in a rush.
“When is your first meeting?”
Shellie sighed and said, “It was supposed to be this afternoon but has been postponed until in the morning. If I had know that before I left, I could have taken a later flight.”
I grinned and said, “Meaning, you could have played with Casey longer and been here when I got here.”
Shellie chuckled and whispered, “Yes, Master.”
“I’ll send the file in a few minutes, so go get settled in your room and call me when you receive it. Don’t open it until I tell you to.”
“Yes, Master,” Shellie said and then added, “I’m about to explode. I think I had a couple of small orgasms during my last nap. The dreams were so good.”
“The actuality will be even better,” I said and then closed the phone.
Grinning, I went to wake Casey and to untie her. She was still a little groggy as I helped her off the bed. “Time for a shower, some breakfast, and some coffee.” I told her as I guided her to the shower.
“I… uh, I have to pee first,” she whispered.
“Are you going to be okay by yourself? I need to finish editing the video and get it sent to Shellie. She’s in Peking and headed for the hotel.”
Casey waved her hand at me as she raised the lid on the commode and sat down. “I’ll be fine when I wake up,” she said with a grin. “Someone and something knocked me out again.”
I smiled and gave her a wink. “I have no idea what you are talking about. You must have been having as good a dream as Shellie had.”
Casey chuckled as I left the room.
It took another fifteen minutes to finish the editing and to start the file on it’s way to Shellie. I was making a fresh pot of coffee when Casey came padding into the living room with a towel wrapped around her head. She sniffed the air filled with the aroma of brewing coffee.
“I’m so hungry I could eat a cow whole,” she said and then laughed as she added, “Horns, hooves, tail and all.”
“There’s bacon and scrambled eggs, and toast on the stove. Help yourself,” I said as I walked over to the kitchen counter and sat down on the stool next to the laptop.
She came over and gave me a kiss on the cheek. With a light blush she whispered, “That was awesome to say the least.”
“A kiss on the cheek, awesome? You’re sure easy to please,” I said teasingly.
She grinned as she walked over to the stove and looked the contents of the pans over. Getting a plate out of the cabinet, she dished up the food. She found a mug and poured her coffee. With a plate in one hand and the mug in the other, she joined me at the counter.
She looked at me over the rim of her mug after she took a sip. “My asshole still tingles.” When I just smiled, she glanced at the laptop. “Is the file on the way to Shellie?”
“Yes, it is,” I said and then sipped my coffee.
“Are you going to watch her as she watches me and us?”
“No, we are going to watch her masturbate as she watches the file,” I replied.
Casey shivered as she sat her mug down and picked up her fork. “Will I be allowed to play with myself while she does?”
“Lets just say, I’ll be recording us, watching her, watching the recording of us. That should either make a full circle or a time warp, I’m not sure which.”
Casey grinned and took a bite of her eggs. A moment later, she whispered, “I’m betting on a nuclear meltdown on two continents.”
Changing the subject, I said, “Tell me about your father.”
Casey shrugged and replied. “There is not much to tell. He died before I was three.”
“Did you have a stepfather?”
With a shake of her head, Casey said, “Mom never remarried, she always said she wouldn’t make that mistake again.” She paused and asked, “Why all the questions? Are you still trying to get into my head?”
“Just something you said while you were out of it earlier. Who is Daddy?”
Casey paused with the fork halfway to her mouth and giggled. Setting the fork down, she whispered, “Daddy is my fantasy guy since I don’t have a real guy to use that I like enough.” She paused a second as she looked me in the eye. “Maybe that has changed now.”
I nodded. “You had me worried there. I thought maybe your dad or stepfather had molested you at some point.”
She laughed and said, “The only person who has ever molested me was me.” she paused again and smiled. “And now you and hopefully Shellie at some point in the near future.”
“You can just about bank on that,” I said mostly to myself as I took a DVD disk out of a case and a felt tipped marker. I wrote “Virgin Casey’s beautiful and luscious ass” on it and then under that I put (First Time). Casey giggled as she saw what I wrote.
“Too bad we don’t have a recording of you getting in that corset and being tied to the chair.”
“Uh,” Casey said and then thought a moment. “Maybe we do. Shellie’s laptop was open on the vanity but I don’t know if she was recording or not.”
I chuckled. “She was recording, believe me. She learned from me the importance of first times and good times,” I said as I put the disk back in the case. “I’ll wait until I have her laptop so I can put that at the front of this file so we will have a full record.”
Grinning, I said a few seconds later, “I’ll put the file of her in Peking and us here on a second disk. It will make one hell of a home movie.”
Casey laughed and shook her head. “No one will ever be able to watch the whole thing in one sitting. Not with dry panties anyway.”
“I don’t think anyone watching it will start out with panties on in the first place.”
Casey laughed again and nodded. “Ain’t that the truth.”
“Now we wait for Shellie.”
I had the laptop set up on the coffee table with my coffee on one side and my cell phone on the other. As time dragged by, Casey came over and lay down on the couch with her head on my thigh. Her eyes were on the laptop screen. Her hand came across my lap and she touched my dick for the first time. It was semi hard and laying on my opposite thigh.
Casey grinned as she ran her fingertips up and down its length and then slipped her fingers around it. She squeezed it gently and then ran her closed hand up and down as it slowly hardened to full length.
I reached for my coffee and as I sat back, I asked, “Are you having fun?”
She nodded and then whispered, “I’ve always been too shy to openly play with one like this.”
There was a piece of Christmas ribbon lying on the floor next to the foot of the coffee table. I had noticed it earlier but now I had a thought. “Hand me the ribbon off the floor,” I told Casey.
She rolled forward, looked down and then reached over and got the ribbon. The ribbon was wide with red and green stripes. It was curled up tightly, probably the end of a roll. Casey rolled back and unrolled the ribbon. With a grin, she wrapped it around my dick several times.
“Pretty but I have a better idea,” I told her as I unwrapped it from around my dick. “Come straddle my lap and let me show you something.”
Casey giggled and eyed my dick, which was much firmer and starting to stand up against my belly. “I think I’ve seen this trick before but in a different position.”
I shook my head as I looked down at her. “You might see that trick again once we get Shellie on the video camera but right now, I have something different in mind.”
Casey shivered hard and rolled over to come up on her knees. “I don’t know if I could with Shellie watching,” she whispered as she started to straddle my lap facing me.
“Turn around with your back to me.”
She tilted her head and turned around. She lifted her left leg and moved it across my lap. Her feet ended up next to my hips and her knees were next to the edge of the couch. As she sat back, my dick was pressed to her tailbone and lower back. She whimpered and then settled her weight onto my upper thighs. The laptop was directly in front of her.
She shivered as my hands came around her sides and stretched the ribbon in front of her chest. With a grin, I rubbed the ribbon across her breasts and against her nipples. She leaned back against me and rested her head against my right shoulder.
“Tying the ribbon around your breasts might be festive,” I whispered as I twisted the ribbon around her right breast and pulled it tight. She moaned softly and lifted her breasts by arching her back.
I laughed. “I don’t have enough ribbon to do the job right, so lean forward.” She leaned forward and I wrapped the ribbon around her neck once and then twice. I still had enough to tie a bow in the back.
Checking the tightness around her neck twice, I got the bow tied. “Now you have a Christmas collar,” I said. “If you stick around, we will have to find something better for later.”
Casey shivered and explored the ribbon with her fingertips. “Go check it out in the mirror,” I suggested.
She wiggled forward off my lap, turned and whispered, “Yes, Master,” and then trotted into the bedroom.
She returned with a big grin on her face. “I love it and I love the way it makes me feel. I feel like I’m part of something much bigger than just me.”
Suddenly there was a chat request on a messenger service on my laptop. “Come sit on my lap, Shellie is requesting a video chat.”
Casey moaned loudly and climbed up to sit on my lap, as she had been earlier. My thighs spread her legs wide and her sex looked very wet as I activated the web cam on our end. I split the screen and brought up Shellie’s web cam. She was laying on her side on a bed, her head, shoulders, and the upper part of her breasts filled the small screen.
Shellie’s eyes were not looking at the camera but at the screen of her laptop. She licked her lips and groaned softly. “You two sure look comfortable.”
“So do you but we can’t see all of you. Do you have your remote camera with you?” I asked. Shellie nodded. “Then get it and attach it to the post on the footboard to the left of your laptop. That way we can look up along your whole body.”
“Uh, how did you know this bed was a four poster?’
“I can see one post behind you so….” I let the sentence trail off.
Shellie grinned and shook her head. “You are sometimes much smarter than you look,” she whispered.
I frowned and said, “Be careful or Daddy will spank.” Then I noticed she was not wearing her collar. “Where is your collar?”
Shellie squirmed on the bed and said, “Uh… I… uh…. Casey is…. Uh… I thought….”
“If you were home and topping Casey then you would still wear your collar if I was here.”
Uh, yes, Master. I’m sorry, Master. I didn’t understand,” Shellie said quickly and then she rolled away from the camera.
Casey squirmed on my lap. “Can I ask what a top is, Master?” As she spoke, her hands moved from my thighs to her own and then folder across her belly. It was as if she didn’t know what to do with them.
I took a wrist in each hand and pulled her arms behind her back. I placed her arms so they were parallel and had her grab the opposite elbow with each hand. “This should keep your hands out of trouble,” I said teasingly.