From Easy Street to a Hard Road Ch. 08

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Donna keeps Bryan on a chastity high.
2.9k words
4.42
71.4k
11

Part 8 of the 13 part series

Updated 10/24/2022
Created 11/06/2005
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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".

Sunday saw me getting some relief. No, unfortunately, not that kind. But Donna was so worn out from our exploits that she had little to no interest in sex. We lay in bed together until past noon, cuddling. It was terrific. The only problem I had of course was that my poor cock had very much interest in sex. I had been awakened several times during the night as he strained against his plastic prison.

The CB-3000 had become very familiar to him and me by now. It felt almost as if it was a part of me, that it was supposed to encase my manhood. Anyone who has been imprisoned in a chastity device for an extended period of time knows what I am talking about. And I don't know if words can suffice to express the feelings to anyone who hasn't. I have wondered if it may be a version of the Stockholm syndrome. This is when hostages begin to relate to their captors because they rely upon them so much. A somewhat simplified explanation, but it will work for our purposes. I had come to find the cage comfortable, as if it had molded itself to the base of my penis, and my penis to it. Almost as a pair of shoes or jeans become fitted to your feet or your butt after a few days of being worn. When I wasn't aroused, it was easy to forget that I even had it on. Of course when I was aroused it was sheer torture as my cock tried to push well beyond the space allowed it within the cage. Yet even that became a comforting sensation. I know it sounds strange, but I'll try to explain. When your cock tries to expand, it ends up pressing very firmly against not only the end, but the sides of the cage, resulting in a sensation almost like being squeezed firmly by a hand (of course a beautiful woman's hand in my imagination). So that tight squeeze is something you desire, contact with your deprived manhood.

Thus results the extreme and contradicting feelings. While I certainly yearn for the cage to be removed so that I can sink my throbbing cock into Donna's moist, enveloping sex, when it is removed, a part of me misses it because I'm so used to it. While I want to feel a nice, hard, satisfying erection, since I can't have that I revel in the sensation of having my throbbing manhood squeezed tightly within its cage. The only feeling that doesn't have a corresponding contradiction is that I want to cum!!!!! Oh, how I need to cum!!!! I want to feel hot semen blasting through and out of my dick instead of seeping out uselessly. I want to feel the hot surge of an orgasm flushing throughout my body. Dammit, I need to cum!

When we finally got out of bed we showered together. I lathered Donna up and took my time washing her beautiful body, caressing her lovingly as I did so. I massaged her back firmly, working my way down to her perfect buttocks, and caressing them lightly. She turned around and I began at her shoulders, then gently cleaning her magnificent breasts. I stood awestruck momentarily as I stared at the hickeys that covered them from the repeated sucking they had endured during her brutal fucking the night before. Oh, damn how I wish I had put them there! Mr. Happy surged inside his cage, and Donna giggled playfully, playing with her tits and letting out an exaggerated moan of ecstasy, then giggling mischievously again as she smiled at me.

After our shower Donna told me officially what I had already figured out. She was completely "fucked out" and wanted to just spend the day together doing things we liked to do as a couple. Its not like I really had a choice in the matter, if she was not in the mood she wasn't in the mood. But when she caressed my arms and asked if I was o. k. with that, it served to remind me that our dominant/submissive relationship was special. It was turning out to be just where we wanted it to be, where we could both be comfortable with it. When we were at play there was no question who was in charge and who absolutely wasn't, but she still respected me enough to want me to be happy. And as I said before, I wasn't to be relegated to being a gender confused wimp cowering in a corner. Damn, I love her! I told her that although I was still on a sexual high and definitely wanted to cum, I also needed a bit of a reprieve.

We spent the day relaxing by slowly getting around for a day out. Donna likes to search antique shops for items that she collects, and we both really enjoy sitting and reading a good book. So we "ran the traps" of her favorite shops, then spent an hour or so drifting around inside our favorite bookstore. Then we took in a movie before enjoying dinner in quiet, out of the way restaurant.

I wouldn't want to leave you with the impression that the day was completely asexual, because that was not possible in my current condition and with Donna's mischievous nature. We walked everywhere arm in arm, kissing occasionally and talking quietly like lovers do. Donna wore a sun dress, which she knows drives me absolutely nuts, and as if that wasn't enough she chose one that was very low cut so I could see the hickeys on the exposed parts of her breasts. She was teasing me subtly, with very little effort at all. Each time the sunlight created a silhouette of her heavenly form beneath the sundress, each time I saw the bruising on her ample breasts, and each time I caught some guy staring at the same things, it aroused me all over again. In addition to these, she would occasionally tease me overtly, and of course she insisted that we return the bookstore which employed the clerk that we now knew was into femdom. And more importantly knew something of my secrets too.

The clerk spotted us in the store and kept casting furtive glances at me. She appeared to be only nineteen or twenty, which only served to reaffirm my impression that in spite of her earlier comments about being a "top, always", she was probably either an inexperienced domme or a wannabe. As Donna and I sat in the coffee shop area, I commented on this to her and she agreed. She observed the girl "working" in a nearby aisle and caught her watching us. She held out her hand to me, "give me one of your business cards". I did so and she jotted down her cellular phone number on the back with a short note that read "call sometime if you would like to take part in a training session, it could be fun". Donna handed me back the card, "O. K., there's not anyone around her right now. I want you to approach her, kneel down in front of her and hand her the card. Tell her that I want her name."

I stood and approached the girl, who looked as if she were about to turn and run, but didn't. I looked around to make sure nobody was looking (wouldn't want to get her in trouble at work), then knelt down in front of her. I silently handed her the card and waited as she read it. A giddy smile took over her lovely face and she looked at Donna and nodded. I quietly told her that my Mistress would like to know her name. She hesitated, nervous, then leaned down and whispered it in my ear. As I stood and turned to go, she stopped me, grabbing my arm, and offering a quick "thank you". I reached out and took her hand, leaned in a little closer and whispered, "my pleasure, ma'am. It appears that I am to be at your service, miss. From now on thanks will not be necessary." I then walked back to my seat and told Donna that the young lady's name is Cindy.

With all of this going on, by the time we left the restaurant to go home, my cock had been straining against my cage intermittently all day, and the front of my jeans were darkened with soaked in precum. Donna laughed playfully at me as I tried to make it to the car without too many people noticing.

At home we sat and held each other in the living room for awhile, talking about the changes in our lives and how they would affect us. We each reiterated that we had to be careful around the kids, but that other than that we were going to have fun with it. Eventually we got around and changed clothes, ones that didn't prominently display my seeping cock or her "fuck bites" as she called them jokingly, then went and got the kids from their respective friend's houses.

Later that night we drifted off to sleep as I held her in my arms, wondering what the coming days would bring.

The weekdays were still filled with sexual tension for me, but not nearly as intense as the weekends had been. Donna was still intent on maintaining the tease, and not just having me wear the CB-3000.

Monday morning we were awakened by the alarm. I rolled over to kiss Donna good morning. She accepted my kiss, and then without ceremony placed her hand on my head and pushed me downward toward her nether regions, "give me a nice, slow, good morning cum, little boy. Nice and gentle, mmmmmmmm, yeah, that's it..."

I smothered her inner thighs and kisses, then covered her entire sex with my mouth, using my lips to gently massage her pubis for a few moments. Then I lightly traced the outside of her soft petals with my tongue before I sucked first one and then the other into my mouth. Releasing them, I separated them with my tongue and ran it up and down the insides of her lips, bathing them lovingly. Donna reached down and grasped my hair, "oh, yeah, that's it baby, take your time...." She sighed contentedly, then moaned quietly, sounding almost like a kitten purring.

I flattened out my tongue and ran it up and down her sweet pussy, massaging her inner lips and her canal, varying pressure from light to pressing, and then I covered her clit with my tongue, keeping it still while I hummed against her. I was well satisfied to hear her sighs of pleasure at this technique that I had happened upon. I spent the next fifteen minutes alternating from gently bathing her sex with my lips and tongue to darting my tongue back and forth across her swollen clit. Finally she pressed herself firmly into my face as she cried out softly, "Oh, fuck, oh fuck, oh yes......" as she shuddered through a long orgasm. I gently caressed her tender sex until she pushed me away gently.

I moved up beside her and she kissed me slowly, licking her juices off of my lips. She glanced down and saw Mr. Happy purple and straining against his plastic cage, a long string of precum hanging down toward the bed. She let out a little school girl laugh, "poor baby. Poor, poor baby." Reaching down and turning my tortured cock one way, then the other to inspect it and looking at me coyly as I moaned pleasure from the contact, she said, "God, I am loving this.... I am so lucky to have a twisted pervert like you!" She kissed me again before we got up to get ready for work.

I started to put pajama pants on so that I could wake the kids, as is part of our routine. She stopped me and explained that we were to have a new routine....she would wake the kids and while she was getting ready I was put on running shorts and go for a run. A mile would do for now, but that would increase as I got into better shape.

After my run we saw the kids off to school and I showered. When I walked back into the bedroom I found that Donna had removed a package out of her dresser and threw it on the bed. She walked over to my dresser, opened my underwear drawer and took out all of my briefs. I watched curiously as she walked over and threw them into the fireplace, lighting it ceremoniously. Smiling, I gave her a "now what" look. She opened the package, but before removing its contents she spoke, "I'm not going to turn you into a cross-dresser, but you have no idea what the feeling of silk against your skin and probably against Mr. Happy's exposed areas feels like." Removing the items from the bag she said, "So I took the liberty of buying you all new underwear. From now on you will wear only loose fitting silk men's boxers."

I was to find that she knew what she was talking about. The soft, light touch during the day as the silk moved back and forth across my crotch and flesh served very well to imitate a woman's gentle tender caress repeatedly during the day. Holy crap she was evil! Damn, I love her!

That evening we were busy running the kids to their various activities and having dinner. Finally we found ourselves alone at the end of the day, winding down in our bedroom. We both thought we were too tired to be aroused, but as soon as I saw her in the nude, Mr. Happy tried to spring to life, straining against his cage. My frustration in turn aroused Donna, who gave me an evil look before walking to our closet and returning with her largest strap-on dildo. My eyes widened, afraid that she intended to use it on me. She laughed that mischievous laugh and dropped it in my lap, "strap it on, cowboy....your gonna fuck my brains out...."

I fastened the harness about my hips and tightened it, pulling it snug until the 9-inch pseudo-cock pointed hard and straight from my midsection. It was at the same time frustrating and thrilling to have a massive cock just above my own, which was forced even further downward by it. As Donna lay back at the edge of the bed, I slathered the huge dildo with lubricant. She crooked her finger, indicating that I should approach, "take me big boy...."

I stood between her spread legs, teasing her lovely nether lips with the head of "my" cock. She sighed contentedly and gyrated her hips....humping the cock. Slowly I pushed into her, spreading her lips and plunging the cock into her. As I increased my rhythm, sawing into her more and more forcefully, my cock was trapped uselessly out of sight. As she began to moan and cry through her first orgasm, my cock was dripping precum like crazy....I can't possibly convey what a sexual high I was on, how sweetly frustrating it was to having her cum all over a hard cock just above my swollen, purple, throbbing cock, my poor cock that needed to be plunging into her so badly.

After she finished scratching the hell out of my back she lay back and relaxed..."mmmmmmm, baby that was good....now get down here and cuddle me...I'm about to fall asleep..." I started to remove the strap-on harness, but she stopped me, "Oh, no, leave it on....I want to feel a hard cock pressing against me as I drift off to sleep loverboy..." As I spooned her she quickly drifted off to sleep, in contrast to me.... I lay awake for sometime, imagining what it would feel like to have MY manhood pressed against her ass, and trying to forget the pain of it trying to push through the vent holes of my cage instead. Precum ran across my leg, making a sticky mess. Finally after awhile I drifted off to a fitful sleep.

This was pretty much how the rest of the week went. Constant teases between our normal lifestyle, taking care of the kids and going to work. I was amazed at the variations Donna came up with in order to keep me almost constantly on edge.

Friday morning Donna had told me that the kids were going to grandmas for the weekend, and I should be prepared for a very "busy" weekend. Time was passing very slowly that day as I anticipated what might happen that evening when I got home...and our weekend began. So I was extremely surprised when Donna strolled into my office during my lunch hour, being followed closely by youthful Cindy from the bookstore. My heart raced. What did she have planned?

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4 Comments
AnonymousAnonymousover 17 years ago
Love these stories

Making hard to wait in between them.

Your Fan

AnonymousAnonymousover 17 years ago
Too long between parts

I can't wait to see what the new little dom brings to the story!

belted and teasedbelted and teasedover 17 years agoAuthor
Reply to Anonymous in USA

I rated the segment at 50 so that I wouldn't skew the end results. I'll be brief...I appreciate your comments and this series probably will wrap up soon, but:

It hasn't been 30 days yet, but it soon will be. We're in the last week.

If the couple decides that one will not have sex and the other will, that is part of their "fantasy", and a tremendous part of the tease.

There is another segment pending approval as I write this. I broke them up into smaller segments because I had gotten so many requests to get another segment out--so somebody apparently likes it.

Men's silk boxers are hardly feminine underwear. Try them sometime.

Thanks again for your comments.

AnonymousAnonymousover 17 years ago
Too short

This story episode was really too short. The motor is just getting warmed up and then it gets shut off again. It's well-written, as were all the other episodes, but we still don't understand certain important elements. Firstly, how is this couple avoiding a sexually-transmitted disease? There is no contact in this episode (with others outside the marriage) but such has previously taken place and the sex was unprotected (the one who gave her hickeys did not use a condom, to the best of my recollection). Secondly, the original story indicated this "game" would go on for a month. Presumably our "hero" would finally get to have an orgasm, which would be like the eruption of Krakatoa, and then the couple would re-assess the whole chastity, tease/denial thing. But hasn't it already been 30 days? It sure seems like it. All these scenes, plus the need to work during the weekdays, spend time with the kids, do activities of daily living, etc., would suggest that some considerable time has passed during these episodes. Time for our boy to come already! Thirdly, early in the series (and stated again in this episode), we are told Brian is not a cowering "wimp" yet it seems that is exactly what he is. It is hard to believe any person would think it is OK for one partner to have sex with lots of others and the other partner to just give oral, or get teased, but never get to have sex (we are using the Bill Clinton definition here; i.e., have intercourse). Why can the wife screw whomever she wishes yet the husband is chaste and has never "had sex" with anyone else? This is clearly femdom, cuckolding, and Brian's fantasy is "wimpish" any way you look at this. In other episodes he has been bi, "forced" though it may have been; now we have hints of cross-dressing (silky underwear, all the traditional men's underwear going into the trash). The plausibility of the continuing episodes really does not compare to the terrific fantasy in the original, first episode with the out-of-town trip and need to satisfy all the horny female attorneys while remaining chaste. I think the author should consider wrapping this series up and perhaps write a new series with different characters and novel ideas.

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