From Easy Street to a Hard Road

Any feedback is greatly appreciated. Not only does it encourage an author to continue writing; it helps him/her to improve their product. I would like to thank those who have offered feedback previously.

If you have not read the previous portions of the "Easy Street" and "From Easy Street to a Hard Road series, you may wish to do so. For the readers who have been asking...I apologize for the lengthy divide between story segments...been busy. Thanks for all of the positive comments; I'll try to keep 'em "cumming".

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My afternoon at work was pure hell. My cock was no longer dripping pre-cum continuously, but my little "session" at lunch, my milking, had done nothing at all to relieve the sexual tension I was under. Quite the contrary it had only heightened it more. It continued to amaze me that every time I thought I had reached the limits of my sexual high, Donna found a way to make it worse. Or better. Or both. I can't say anymore! As I've said before, extended chastity is at the same time pure torture and sexuality at its best. At times I felt like it was killing me, but at the same time I wouldn't trade this experience for anything. My cock was trying desperately to burst through its cage. I was thankful that the CB-3000 kept it from being visible to my co-workers.

About mid-afternoon my email notification went off on my computer, and I saw that I had an email from Donna. I opened it and read.

Bryan,

I'm sure you remember your friend Mary from your Florida convention. You know the one with the southern accent that you told me about? Well she sent me an email. It seems that she thought of a way to contribute to your tease and asked if she could give you something. Considering, I was all for it, LOL! So, open her email, then the attachment, and download it to your IPOD. I expect you to listen to it all afternoon when you are able. Love you! Oh, I'm glad you are silly enough to share your weaknesses with people! You may regret it though!

With trepidation I opened the attached email from Mary. I had met her at a conference in Florida, and her southern drawl had driven me absolutely nuts. You know the accent I'm talking about. She couldn't speak a single word that wasn't laced with latent sexuality. Even "Good morning" was drawn out, erotic, and made a man hard as a rock. And of course, like all southern belles, she knew it. And wasn't afraid to use it! The email that she had sent to Donna explained that she continued to think about the convention experience and my predicament. She wrote that she had made a recording that she hoped would be useful in teasing me to distraction, and concluded by telling Donna to forward it to me if she approved. Obviously Donna had. I was nervous. What had they cooked up?

Shaking a little bit, I took my IPOD out of my desk drawer and downloaded the attached sound file to it. I used the IPOD to listen to relaxing music when I wasn't in a meeting or on the phone sometimes. Placing the headphones over my ears, I located the file on the little computer and started to play it.

Sweat broke out on my brow and I almost doubled over at the inevitable response of my manhood to Mary's sultry voice, "Hello, Bryan, I've missed you. And I've definitely missed that talented tongue of yours, honey." My heart raced. How could she have such an incredible effect just by talking? No wonder men had fought to the death over these sensuous southern belles for years. And the sound of her voice brought back memories of her beautiful body and how it responded to my ministrations.

In that incredible southern drawl she spent the next hour recalling in graphic detail our "sexcapade" together in Florida, taking every opportunity to comment about how wonderful it had been. Then another hour was spent describing to me just what she would like to do to me once my cage was removed and I could cum. Oh My God how she described how she would make me cum, making sure to dramatize her accent every chance she got.

As if that wasn't enough, when she finished telling me what she wanted to do to me, she continued, "Well, I hope this has driven ya'll crazy sweetheart. You should probably save the next few files for another time, when Donna tells you to listen to them. Let's just say that you made me very, very, randy and I've been very, very bad since then. I've been recording things every time I got to make love and I wanted to share it with you, honey. Hope things are lookin' up for you very soon darlin'!" With that the file I was listening to ended.

Damn! I was leaking again already! Women are evil! And I love it! I had to take some tissues from my desk and stuff them around my cage so that I wouldn't embarrass myself around the office. Fortunately for me it was almost time to go home. I couldn't wait to see what Donna had in store for us this weekend.

By the time I arrived home my anxiety was driving me completely nuts. I parked my car in the garage and walked into the kitchen area, filled with trepidation, not knowing what, or who I would find when I got inside. I found the kitchen empty and the dining room too. I heard the television going in the living room, and walked there, hesitantly.

I was surprised to find only Cindy there, sitting in the recliner watching a game show on TV. She was wearing a "wife-beater" style tank top that clung tightly to her slim figure and a very short pair of shorts. Her right leg was splayed lazily over the arm of the chair and she was subconsciously twirling a finger through her blonde hair, which was now pulled back into pigtails. I stood there for a couple of minutes, not really knowing what to do until she finally noticed that I was there.

"Oh, you're home. Hi, Mr. Bryan." She sat up, and looked at me expectantly. I finally caught on. Or at least I hoped I had. When I spoke it came out almost as a question, "Hello, Miss Cindy..." She made a face as if considering something, then smiled, "I like that. It's all kinda Gone with the Windish, isn't it?" I felt a little more at ease now, but not much, "Yes, ma'am." I hesitated, wanting to ask where my wife and kids were, but not knowing if I should. She recognized the unasked question, I guess, because when she spoke again she answered it, "Its just us here, Mr. Bryan. Donna...er....MISS Donna...is taking your kids over to their friend's houses for the weekend. Nice kids, by the way."

She looked back at her program for moment, leaving me standing there. After a moment she turned back to me, "Anyway, Miss Donna said I was in charge until she gets back. She said I could play with you however I wanted till then, as long as you are naked and have the living room clean for our guests by the time she gets back. That's O. K. with you isn't it, Mr. Bryan?" I was surprised by the question, but then I also sensed that it was asked in a mildly sarcastic tone. "Of course, Miss Cindy."

She continued almost matter-of-factly, "Well, then I guess you should get naked. Just go put your clothes away, and then come back." I did as I was told, trembling a little as I put my clothes into the hamper and walked back down the stairs. I knew I was being silly, especially after this afternoon, but part of me was nervous about whether Donna had actually given me over to this young girl. Would I be in trouble if Donna walked in and found me naked with her? I got back downstairs and stood waiting for instructions. Cindy was back into her relaxed position in the chair, only now her shorts were off and lying on the floor next to the chair. She wore no panties and her young, pinkish sex was clearly visible, covered by a light down of blonde pubic hair. She continued watching music videos on TV as she spoke.

"I was telling Miss Donna how exciting it was this afternoon when we came to your office. It got me really hot, Mr. Bryan. I had to go over to my boyfriend's before I came here cause I just had to get fucked. I rode him like he was a stallion, Mr. Bryan. When I got here I asked Miss Donna if I could take a bath and she had another suggestion, so before you start cleaning," she stopped, as if she had said something funny, giggling in that little cheerleader voice of hers, "Before you start cleaning the house I have another job for you. Lie down on the floor in front of the chair, with your head facing the TV. No, on your back." She had never once turned to look at me, continuing to watch her videos the entire time she spoke. Once I was in place she got up, stood over me, then knelt down over my face, her tight little pussy touching my lips. Still she never looked directly at me, taking me completely for granted, which somehow was disconcerting and very arousing at the same time. She was still watching TV as she spoke, "He comes a lot, Mr. Bryan. So be sure to do a good job...Miss Donna says you are really good at this". She placed one of her little hands against her belly and pressed inward and downwards. Soon a glob of cum appeared at her nether lips and dripped into my waiting mouth. Her firm young pussy mesmerized me and my cock throbbed desperately against its prison as I began to delve into her sweetness. I darted my tongue into her and sucked gently...then more firmly. I wanted to get the "cleaning" out of the way so that I could concentrate on making love to her tight little honey pot with my mouth. She continued to watch her videos, paying no attention at all to the man sucking on her vagina. It became a quest with me to draw her attention to me, to show her something much more interesting than MTV.

She was right about her boyfriend. It seemed to take forever before the last of his cum slithered out of her sex. I began in earnest to try and give her an orgasm. I enveloped her entire sex with my mouth (it didn't take much), and massaged it gently, then I tenderly drew her nether lips into my mouth one at a time and sucked on it, at the same time massaging it with my lips. She seemed to realize that the cleaning was finished and began to stand up. I managed to dart my tongue across her clitoris twice before she drew away from me. She stopped a few inches away from my face, still watching TV. She hesitated for a moment, then made her decision, sitting back down firmly on my face without saying a word. I darted my tongue across her clit several more times, then ran it deep into her slit and into her canal, fucking her with my tongue. Almost subconsciously (I think) she rotated her hips gently, grinding herself on me softly. I thought to myself that I had her now. I massaged the tender spot between her vagina and her brown bud, then hardened my tongue and pushed it into her ass, stroking in and out. She let out a shocked sigh that dragged into a moan of pleasure. Wow, I don't think anyone has ever done that for her before. I sucked and nibbled on her lips again before returning to her swollen clit. She was definitely ready now! Her head dropped from watching her videos and she let out a whimper before resting one hand on the floor for support and grasping my hair with the other. I went after her clit with a passion now, darting across it, then massaging it with my tongue flattened.

Her voice was light and the sounds came out high, but not quite what I'd call squeaky, "Ohhhh...........oh..oh....oh...ohh......." She clenched my hair tightly within her little fingers and began fucking my face desperately as her orgasms overtook her, "OH...OH...OH..OHOHOHOHOHOHOHOHOOHHHHHHH....FUUUUUUUUUCCCCCKKKKK!!!!!!!!!" The last came out as a scream that echoed through the house. I sucked on her clit, sucking it and the flesh around it into my mouth and then danced my tongue across it inside my mouth, "MMPPPPPPHHHHHH......uuuunnngggggggghhhhhhhh....." I recognized what was happening when she began taking in quick, sharp breaths as if she were hyperventilating because another even more powerful orgasm was coming on immediately after the first...and she wasn't ready for it. Being the gentleman I am, I was determined not to let her recover. I reached up and grabbed her hips as I rubbed her clit firmly with my tongue.

"Ungh.....UNGHH! Mother......fucker! YEEEEESSSSSS!!!!!!!!! GOD! OH....oh...oh...pleeeaassseeee....don......d-d-d---don't.......stop! Yes....mmmppppphhhhhhhh......." She shoved her sweet pussy down tightly over my mouth and squeezed those beautiful, satiny, athletic thighs against my head, holding me in place almost frantically. I don't think she could make any more sounds other than occasional mewling as her entire body shuddered and convulsed for what seemed like forever. Eventually she relaxed her grip and fell forward onto the floor, exhausted. I was still staring up at her swollen pussy lips covered with that light down of blonde pubic hair. Her sex and her thighs were moist with perspiration. Her scent was heavenly. I couldn't resist and lifted my head up, licking nectar from her flower. She reached back with one hand and slapped my shoulder weakly. I couldn't tell if she was trying to smack me in a dominant role, or if she was tapping out like a wrestler saying she'd had enough. Either way. I lay my head back down and basked in the satisfaction of what I'd just done to her. My poor tortured cock had left a puddle of pre-cum on my stomach and was straining against its prison, but at the moment I didn't care. It was worth it!

"I told you he was good." How long had Donna been standing in the doorway? "Caress her and help her calm down, Bryan." I did as I was told, taking one last look at her sweet sex before I got up and began lightly caressing her back and shoulders with my fingertips. Cindy sighed contentedly and basked in the attention. Donna walked over and sat on the couch for a few minutes until Cindy had recovered and got up off of the floor. Back in control of herself, she virtually ignored me as she sat down in the recliner again, not bothering to replace her shorts.

Donna snapped her fingers to get my attention and motioned for me to kneel beside the couch. They spoke to each other as if I weren't there. Donna fully dressed in business attire, Cindy in only her top, her leg again splayed over the arm of the chair. They spoke about femdom and male chastity among other things, with Donna asking Cindy about what she had done in the past and what her fantasies were. After her recent orgasms Cindy was more than relaxed and ready to share. It turns out that she had dabbled with femdom with her boyfriends, but none of them had been mature enough to handle it, so mostly she had been teasing the hell out of them and fantasizing about what she wanted to do.

Donna said that for the next couple of hours Cindy could do anything she wanted to me...that I was all hers until the other guests arrived. Then they'd all play. Cindy asked, "So...what should I do?" Donna laughed quietly and said they had plenty of time to explore, and that Cindy should just pick something she had wanted to do and do it.

"Well...I've spanked some guys before but I've always wanted to do it up right...with whips and all." Sweat popped out on my brow...this is what I'd been afraid of...merciless Cindy let loose on me. Donna didn't even turn to look at me as she said, "Bryan, go and get all the toys Miss Cindy might want to beat you with."

As I collected the required items I was trying to guess whether Cindy would be timid about hurting me since she didn't have much experience, or would she go wild with it because she was so young and wouldn't think about whether she was hurting me. I hoped for the former, but subconsciously expected the latter.

When I returned from our bedroom, I laid out the items that I'd found on the coffee table in front of the ladies. First was my western style belt, with coins inlaid every six inches or so. Then a paddle I'd made (under duress, I might add) that was basically a three foot 2x4 sanded and with holes drilled into it to cut down on wind resistance, and a handle at one end. Third were a whip and a cat-o-nine tails. Last was a riding crop. I could feel the heat radiating from my flushed face as I moved back over and knelt next to Donna again, silently hoping they would talk for awhile before Cindy began. They shared knowing glances, their eyes smiling, then Donna spoke, "Nice try Bryan. Kneel in front of Miss Cindy and await her command." As I knelt on my knees in front of Cindy, my hands clasped behind my back and my swollen cock dangling uselessly from my midsection in its prison, she looked around the room mischievously while forming her plan.

When she had made her decision she directed me to the other side of the room just below the second floor landing. She directed me to reach up and grasp the molding that lined the bottom of the landing, which left me stretching upwards, balancing precariously on my toes. Her voice was almost mousy, "OK, Mr. Bryan, hold on tight", she giggled excitedly, "If you let go, I'll just have to make it worse on you!" In my strained position my buttocks were drawn tight and my calves were flexed, and I knew that the pain from what was about to happen would be intensified because of it. My heart beat quickly in my chest, I closed my eyes trying to concentrate so I wouldn't make matters worse, and my cock stood as erect as it could while it strained against the plastic. She turned back to Donna and asked what she could use to bind my wrists to the staircase railing above me. They both walked upstairs and disappeared into our bedroom. When they returned Cindy knelt down on the landing above me and fed a leather cuff through the railing then fastened it to my left wrist. She ran leather strap connected to it through the railing, then connected another cuff at the other end to my right wrist. The leather strap was then tightened to make sure I couldn't relax and had to remain on the tips of my toes.

The room was completely silent for what seemed like an eternity. Then I could sense Cindy moving about behind me, but nothing happened. The fear and anticipation grew and I realized that Cindy indeed knew how to tease. She was using the time to build me up, and I was sure she could hear my breathing becoming more ragged. Finally I felt her delicate fingertips tracing my taunt ass cheeks, teasing about them, then running up the crack. She rose up on her toes behind me so that her hot breathe caressed my ear as she whispered, "You have a really, really nice ass, Mr. Bryan. It's a shame to tear it up, but I really, really want to....I'm gonna enjoy it sooo much. I think it will look really good when it's a nice crimson color too."

Again silence. Then I heard the swish of the cat and tensed up just before it landed across my calves. It wasn't that bad. Then I heard Donna speak, "Its OK, Cindy. Let go, he can take it, you aren't going to break him—not physically anyway."

SHIT!

The next blow was much, much more painful as Cindy reared back and put everything she had into it. I tried not to cry out, but couldn't help but emit a tortured, "MMMPPPGGGHHHH!!" There was a pause, then I felt Cindy's hand caressing the injury she had just caused to my ass, "Oh, Fuck Yes, that's what I'm talkin' about..."

This time she stood directly behind me grasping the cat in both hands and swung it back and forth, back and forth like a slugger practicing for their turn at bat, as hard as she could. Each time the cat passed me it lashed out at my tightly drawn buttocks, harder and harder. This went on and on...where was she finding the energy?! I could hear her ragged breath mingled with excited laughter and an occasional "YES!" or "Oh, yeah!" I clenched my teeth and tried to keep quiet. I was determined to maintain my composure no matter what she did. The strikes with the cat against my butt stopped. I could hear Cindy panting behind me, trying to catch her breath. Finally she could talk and I heard her say to Donna, "Whew...I can't believe it....I fuckin' CAME!" She moved right up behind me and I turned my head to look at her. Her eyes laughing, she reached down between her strong thighs and ran her hand into her soaking pussy. Then the hand came up and she smeared her juices all over my face, making sure to coat my mouth and just below my nose....I sighed in frustration...damn her musk smelled good!