From Easy Street to a Hard Road

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Donna likes it.
4.9k words
4.47
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Part 1 of the 13 part series

Updated 10/24/2022
Created 11/06/2005
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(If you have not read my initial post in this series, "Easy Street", then you may want to read it first. There is no preamble describing the last episode. Comments are welcome and appreciated.)

Donna met me at the airport. I had never seen her look so radiant, so ravenously sensuous. The gleam in her eye told me that she had definitely decided she liked our new arrangement.

She met me at the exit gate, and we got several stares from passersby as we kissed passionately for several minutes right there in the middle of the terminal. She reached her hand down to feel "Mr. Happy", making sure that his cage was still secured. Her laughter was like music to my ears. That combined with her passion told me that not only was she incredibly turned on by our games, but that I didn't have to worry about losing her. We walked hand in hand to my truck, which she had driven to the airport. We talked about the kids, about missing each other, and about the incredible sexual experiences we'd each had while I was away.

When we got to the truck she got in to drive. I was about to open the passenger door when I discovered it was locked. She lowered the window enough so that I could hear her, "Take of all of your clothes and hand them to me. Then I'll let you in."

I looked around nervously. What if someone saw me? I could get arrested!

It didn't take me long to comply however, as the realization that the relief of my throbbing cock was totally in my loving wife's control over rode an fears I may have had. Once I was completely naked I handed all of my clothes in through the window. The only apparel I had on now was my CB-3000, my prison.

Donna took her time, ignoring me as she looked into the rearview mirror to fix her lipstick and comb her hair. Then she nonchalantly hit the lock button and I scrambled inside.

Now she stopped the pretense of not having any interest in me. She turned sideways in the seat and pushed my legs apart. She hefted my tortured manhood, turning it this way and that as I groaned. After the sexual tension I had experience the last few days without any release it felt as if it weighed a ton and would break off with each movement she made.

"Poor baby. Mr. Happy is soooo purple and swollen. Does he hurt?"

I was almost apoplectic, "Unngh. A little. He feels like he could explode."

"Aaaah. Poor thing. Mr. Happy has been so good to me over the years. He doesn't deserve such torture, does he?" Talking in baby talk to my penis as she loves to do during foreplay. Suddenly I lurched in my seat as she tugged him almost violently upward, "Mmmmphh!"

She leaned over and whispered in my ear sadistically, "But you deserve it, don't you, you little pervert?" With that she stuck her tongue in my ear, turned my head to hers and kissed me viscously before releasing me and starting the truck. The drive home was completely silent, and I began to wonder if I had been wrong about her enjoyment of my fantasies. I was thankful that it was dark when we drove home since I was completely naked. Well, almost.

Once we arrived home, Donna relaxed a bit. She had driven into the garage and ordered me into the house. I looked at her quizzically for a moment, hesitant. She understood immediately and didn't reprimand me, "Its ok. The kids are all spending the night with friends. In fact, we have the entire weekend alone."

Once inside, she told me to have a seat in the living room while she changed into something more comfortable. She returned wearing her Terri cloth robe and sat in the recliner instead of next to me on the couch. She motioned for me to come over and kneel in front of her on the floor, which I did. She leaned forward and mussed my hair playfully, then folded her legs up under her buttocks and relaxed in the chair. She looked at me a few moments as if gathering her thoughts, and then she finally spoke. There was no ire in her speech; it seemed we were having a normal husband/wife conversation.

"I told you when you first brought this chastity thing up to me that we would experiment with it for a month before I decided whether it would be more permanent or not. You've been on your trip for the first week, so I don't really feel like that counts. Although just from the experience I've had in that week tormenting you and having the freedom to do what I want, I feel like I could make my decision right now. But I won't." She paused for a few moments before continuing, thinking about what she was going to say. I sat there listening intently.

"I told you last week that you may not know what you are getting yourself into. That is why I am not going to make my decision now. I want to put you through your paces, so to speak. Because it may end up being you that can't handle this when you find out just how perverted I am." She let that sink in for a moment, then, "Do you think that you can go for a month and let me do whatever I want? And I mean anything? The reason I am asking is because I love you and while I am enjoying this, it's not worth losing you."

I didn't have to think about it. "Yes. Anything goes is music to my ears. That's what it's all about. And I am glad you are enjoying it."

She leaned over and cupped my chin in her palm, "I am glad to hear you say that, lover. But you have to promise me that if after the first month you don't still feel that way, you will tell me so."

I tilted my head forward and kissed the palm of her hand. "I will. I promise. But I think I might surprise you." Of course, although I was bundle of nerves wondering what she could possibly have in mind that could overwhelm my erotic desires, at that point I had absolutely no grasp of what things went through her mind.

Donna turned in the chair and spread her lovely legs. Then she beckoned me to my favorite place. While I had really enjoyed all the women I got to please with my tongue over the last week, I felt as if I was home. I leaned in and began to caress her nether lips with my tongue and mouth, sucking gently on them, then massaging them with my lips. I began bathing her sex with my flattened tongue until I sensed that she was ready, then I began darting my pointed tongue across her clit until she cried out in the first of eight orgasms.

After she'd had enough, she stood on wobbly legs and reached down for my hand. She led me to our bedroom. My heart raced! I was home and would finally get some relief for my tortured manhood. When we got to our bed she lay down and I lay next to her. She told me how wonderfully I had performed, and that she would tell me all of the ground rules for the next month in the morning. I looked at her and glanced down at "Mr. Happy". She laughed mischievously, "Oh, that's the first ground rule. Poor Mr. Happy doesn't get to come out and play until the month is up."

My heart sank. He felt as if he were going to burst now! In spite of myself, he was throbbing even harder at the thought of all the torment I was going to experience before he could gain release. Donna laughed again as she saw him twitching because of her words, "You truly are a pervert aren't you, baby? Now get over here and cuddle me."

As my mind raced I wrapped my arms around her and tried to relax. Before she drifted off to sleep she wriggled her butt against my cock, and whispered, "Yep. Not for a month." She pressed back against me, and added, "At least."

I drifted off to sleep, almost afraid to think about what that last comment had meant.

The next morning I awoke before Donna. Which is very unusual for a Saturday at our house. I am not an early riser and she is. But I had someone to wake me up, so to speak. You think that morning wood is a good alarm clock? Try having an insistently attempted morning wood. My cock still stood out from my body, but try as he might; he could not achieve erection. Just pressed ever more firmly against his plastic prison.

I got up and made breakfast and had it waiting for her when she awoke. She walked into the kitchen in her robe, smiling, telling me how she kinda liked this. We sat across from each other and ate our breakfast, talking like the lovers we are. After awhile, I inquired about the ground rules. It had of course been on my mind since I had awaked.

"Well, the first one you already know about. You will not be allowed to have an orgasm at least until the month is up."

I swallowed hard, "Yeah, I was sort of wondering about the "at least" aspect of that?"

"Its simple. We know that this is going to last for a month. If we both decide after the month is up that we want it to continue, it will be up to me when you get to cum. Completely at my whim, right? Isn't that what you said?"

"Yes, ma'am. Yes, ma'am it is."

She took another bite, then continued, "That will be the second rule. When we are playing, you will address me as ma'am or Miss Donna. I don't want you calling me mistress. You can even use that in front of the kids without them wondering what is going on. And as far as the kids go I'm sure we are agreed that they can't know about this. We will behave normally around them. I may be tormenting you, but I don't want this to affect the rest of our lifestyle.

I certainly agreed with that. Although work was going to be interesting while I was restrained.

"Next, you need to get into shape. Not that you are in horrible shape, but I want you to get rid of those love handles and tone up a bit. So each morning you will go for a run and start working out. I will find some chores for you around the house too. Don't get me wrong, I'm not going to use you as a slave to do housework. I will just have you doing things to get you in shape, or to humiliate you when I want."

"When the kids are gone you will be nude around the house. If we go out, you will wear clothing of my choosing. We may have some guests as part of our play. The rule about you being nude applies when they are here also."

I stared off into space for a moment, confused, "Ah, what about our friends not knowing about us?" She wasn't offended by the question, "That applies, unless it is a friend that I decide I can trust to play with us." She grinned seductively.

"I'm sure I will come up with more rules as we go along. Of course, it goes without saying that when I give you a command during our playtime, you will obey without question. Understood?"

"Yes, ma'am."

"Ok. I want you to get dressed; we have some shopping to do. I want you to wear some loose shorts and a nice shirt. No underwear.

Thirty minutes later we left the house. I had thought that loose shorts were pretty tame, and somewhat of a reprieve. Boy, was I wrong. The extra room gave my imprisoned manhood and balls, heavily laden with unspent cum, space to bounce around and rub up against the fabric of my shorts. This was made even worse as Mr. Happy continuously tried to grow, throbbing helplessly, when I saw what Donna was wearing. She had chosen her white sundress, sans panties or bra. She laughed mischievously when she saw my inevitable reaction. Her large swelling breasts pressed against the low cut dress, forming impressive cleavage that drew more than just my attention, her large areola and nipples more than obvious through the light fabric. The light billowy dress swirled and danced around her tanned legs as she walked and as the wind caught it, teasing me and any other male within view. Lastly, but certainly not least, every time the light silhouetted her, I could see her beautiful thighs leading up to that magnificent mound I loved to love. She has always known what a sundress does to me and was utilizing it to the fullest today. She flirted with me playfully. She definitely knows my buttons and was merciless in pushing them. While she flirted with me occasionally, she also flirted shamelessly with every other attractive male we came across right in front of me, driving me crazy with lust and jealousy. Damn, I love her!

Donna had me drive my truck, and as I drove she sat in the passenger seat, her legs spread wide. She almost subconsciously played with her clit as we drove. I could smell her musky scent and hear her breath deepen as she neared an orgasm. This was going to be a long, long month.

Our first stop was the largest bookstore in our city. Donna sipped her cappuccino, as she looked through the sex related books. She would find one she liked and hands it to me, until I was balancing a stack of them. She admonished me not to look at the titles until she told me to do so. Once she had chosen all of the one's she wanted, we walked to the front of the store. Donna indicated the prettiest young clerk there and told me to go buy the books while she looked around some more. "Oh, you can look at the titles as you give them to the clerk." She smiled laughingly as she walked off.

I turned beet red as I handed the clerk the first book, which I saw was entitled, "Love and the submissive male". I saw the shock and then amusement in her eyes when she rang it up. The second book was, "How to dominate your Man", then came "Medieval Chastity Devices". There were a couple of others before I handed her a set that I realized we already had at home. I decided not to question the purchase, realizing it was more to embarrass me that anything as I handed over Anne Rice's version of "Sleeping Beauty", an erotic tale of domination and submission that spans three volumes. Much to my surprise, the girl looked into my eyes and said, "These are my favorite books," as she indicated the Sleeping Beauty series. The suggestive comment was too much to pass up. I tried to remain calm as I asked, "Top or bottom? Or both?"

She looked at me as if she were sizing me up, then responded, "Oh, top, and always." With my other purchases she obviously didn't have to ask what I was.

After I made the purchases I went and found Donna, telling her about the unexpected twist that occurred. As we walked toward the exit Donna walked over to the clerk, leaving me behind. I watched as the clerk took on a "I'm sorry" expression then relaxed as Donna obviously put her at ease. Then Donna wrote something on a piece of paper and handed it to the girl. The girl acted as if she had just been given a Mercedes, her eyes lit up and she grinned uncontrollably. Donna smiled at her and walked back to me. As we walked to the truck I asked what that was all about, and was told in no uncertain terms that it was none of my damn business. Then I was laughed at!

Our next stop was the grocery store. Then we had lunch at our favorite Mexican restaurant. Donna continued to flirt shamelessly with the waiter, the owner, and a table full of jocks that were seated across from us. I tried to pretend that I didn't notice, but I could feel the precum running down my thighs because my cock was straining continuously against my cage.

Our last stop was the local "Toy" store. We spent several hundred dollars in this establishment buying some new toys for our collection. As Donna made her selections she said simply, "No questions." By the time we made it to the check out counter, I was blushing furiously and perspiring. I don't think there was any question for the clerks as to who was going to be the victim of our purchases.

Not permitted to ask any questions, I could only imagine what she had in mind with a whip, a riding crop, nipple clamps, leather restrains, a strap-on harness and several different sizes of dildos to fit within it; butt plugs, a dildo gag, among several other items. Donna also picked out several lingerie items, such as a lacy teddy, several pairs of panties and then some high heel shoes. I was getting excited, anticipating seeing Donna in these items until I realized that they were not her size. Ahh, crap. Cross-dressing is not one of my fantasies. But anything for my mistress.

When we got out to the truck for the drive home I got a surprise. My truck is equipped with a plastic cover over the bed. Donna quietly ordered me to raise it and climb into the bed of the truck. She then told me to remove my clothes and to lie down on my back. I began to perspire, as we were in a public parking lot in the middle of the day. I hesitated and received a smack to my ass for my trouble. Once I assumed the position, with my head toward the cab, Donna secured my wrists and ankles to eye bolts on the four corners of the bed. The she tied a blindfold over my eyes. She chuckled at me mischievously then closed the bed cover. Soon the truck was in motion, every bump like a kick in my buttocks and back on the hard bed liner.

After a few minutes the truck stopped and I heard Donna talking to another woman. The sounds were muffled, so I couldn't make out the other voice, but I could tell that both Donna and the other woman got into the cab before we started moving again. After awhile we parked again and both women got out, I could hear their voices fade off into the distance. I lie in the bed of the truck, helpless and scared for what seemed like an hour or two. I heard people walking by, laughing and talking on several occasions. I soon realized that Donna had left the truck parked in a public parking lot while she and her friend went and did some shopping or something. Each time someone approached the truck my heart raced, and in spite of (or because of) my terror of being found in this predicament, my cock strained against the plastic of its cage the entire time, dripping pre cum onto my belly.

How to describe how it feels to be restrained in a cock cage? Keep in mind, ladies and men who have not experienced it, that a penis is meant to grow, to become erect. As it does so, it expands from a flaccid state to a greatly increased circumference in addition to a greater length. The cage, being only so large around and being bent over double, makes this impossible. So the entire time you are aroused your cock is trying to expand in diameter. The plastic of the cage is like a continuous, firm grip, which feels as if it is squeezing the hell out of your desperate cock. Your member can only extend its length so far until it reaches the end of the unnatural limits placed upon it. It is also doubled over, and naturally tries tirelessly to raise up and stretch out, pressing futilely against the top of the cage the entire time. The precum does not stop, so you quickly find yourself with a real sloppy mess in your trousers or on your belly. I cannot convey the frustration adequately! Nor can I tell you how much I love it. You are constantly in a conflict of emotions and sensations. It places you on such a sexual high that you want it to continue forever, while at the same time you would sell your soul just to be allowed to cum, please, oh please let me cum!

Finally I heard Donna and her friend return. The relief lasted a very short time, however. I soon realized that there were several other voices, both female and male, accompanying them. I could hear the laughing, some of them saying that they "couldn't believe it." My heart stopped as I heard the latch on the bed cover being turned. Suddenly light flooded in. I couldn't see, only hear gasps and uproarious laughter. I could detect the odor of alcohol and realized that Donna and her friend had been in a bar for the last couple of hours. I heard her speak to her newfound friends, ignoring me, she said, "See, I told you. Come on guys, pay up!" I heard the rustle of money being exchanged, and comments from the others, "I can't believe he let you do this." And, "damn, what a pervert!" The Donna finally addressed me, "Hey, honey, you just made me $100 dollars! Maybe I should rent you out and make even more, what do you think?"

I felt as if I was on fire as I responded, "Anything you would like, ma'am." More laughs from her newly found friends. After that the top to the truck was closed again and I heard them all move off toward the bar again. I lie there for another few minutes, wondering what would be next. To my surprise, about a half-hour later I heard the latch being opened again. I could smell the odor of beer on someone's breath, and strained to hear, hoping to discern what was happening. I finally spoke, "who's there"? No answer. Suddenly I felt someone getting into the truck bed with me. The lid was closed and I realized that someone was inside with me now. I could hear their breathing, but they didn't say anything. I felt a leg being moved over me and then I could smell the familiar scent of a woman's sex just above my face. Before I could say anything a moist, tender pussy was lowered to my lips. I knew it wasn't Donna. The woman began sliding herself over my face, fucking herself on me. I was more than eager to have sexual contact with anyone, and immediately began massaging her nether lips with my lips, then began darting my tongue about her sex, dancing it across her extended clit passionately. I heard her groan as she gripped my legs tightly, digging her fingernails into my thighs. I could feel her hot breath on my imprisoned cock, which strained and dripped pre-cum continuously. I was surprised when she latched her moist lips around my cock cage and sucked in desperation, moaning loudly. I could only feel her hot lips on small portions of my cock that were exposed by slots in the cage, but I was so fucking thankful! She began darting her tongue as much as she could into the slit at the head of the cage, lightly grazing my cock head. I whimpered into her cunt and redoubled my efforts, concentrating on her clitoris while still massaging her with my lips. Before I knew it she forgot all about my cock, needing her breath to cry out, "Oh, fuck!, Oh, fuck yes! Uuuuunnnnggggghhhhhh!" as she came hard on my face, her entire body shuddering violently. She held me tight, surprised that I didn't stop. I continued working her downy sex, savoring it as she screamed through four more orgasms in rapid succession. Finally she just dropped onto me, almost smothering with her cunt. After a few minutes she moved off of me, saying, "Damn. Your wife was right. Thank you." And before I knew it she was gone, leaving me dripping sweat and my cock dripping precum.

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