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".

I was really surprised to see Donna stroll into the office that Friday. I was somewhat aghast that she had brought "Cindy" with her.

I had been on an extreme sexual high for nearly a month, my poor tortured manhood straining against the CB-3000 that I had worn that entire time. My testicles were red and swollen, full of cum. The incredible adventure that I had been on since we had decided to experiment with chastity play had been pure torture and at the same time put ecstasy. My only respite had been during the day while I was at work, and that had been only a mild respite. The office where I work as a supervisor includes several women, most of which are in shape because of the business we're in. In my heightened state of arousal, every flip of the hair, every hemline that rose up on satiny thighs, every little feminine nuance drove me absolutely nuts. Yet I had to try and hide my frustration. This is not one of those stories where the girls at the office are going to get involved in our sex life...unemployment would have a very negative affect on our lives over all, including our love life.

Which is why I was so nervous when I saw Donna and Cindy enter the outer offices. I trusted Donna, but it was obvious that she intended to do something sexual or she wouldn't have brought Cindy with her. Surely she wasn't going to "out" me in front of my co-workers? Surely she knew better.

Donna approached me with a smile, and said hello to Beth and Mary, a couple of my co-workers that were nearby, trading pleasantries as if this was just a normal, stop by the office for minute visit. She gave me a quick peck on the lips and said, "Hi, honey!" She introduced Cindy to everyone as a friend, and then turned back to me, "Can we talk a minute alone Bryan?" I led her into my office and Cindy followed, and Donna turned to close and lock the office door. When she turned back around she was laughing lightly, her eyes sparkling, "I scared the crap out of you didn't I?" I nodded in the affirmative and she continued, "Good! Don't worry, I'm not gonna embarrass you, but the look on your face was priceless! Now. Get out of those pants.."

While I removed my shoes and pants, shaking, Donna explained, "I told you we had things going on this evening. Actually, you're in for another full weekend, babe. This evening we're gonna let Cindy get a taste of the lifestyle, sort of a training session for both of you. We came by to prep you a little bit so you won't explode this weekend!" Again laughing at my expense.

Soon I was standing there in front of both of them, nude from the waist down save for the cage tightly embracing my straining cock. Cindy couldn't help staring. We had met her at our favorite bookstore and inadvertently discovered that she was a wannabe Domme. Donna had invited her to join us to "get a taste". Donna saw her staring at my purple, swollen cock and balls straining against its cage, dripping precum from weeks of constant sexual frustration. She told Cindy to go ahead and inspect me more closely while she explained things to me, telling me to "stand at attention", hands at my sides.

Cindy knelt down in front of me, checking me out as if she were looking at a strange new toy. From the look on her face, from her demeanor, and from the total lack of embarrassment she showed while inspecting me, I certainly had the impression that she was used to taking "boys" for granted. The only thing new to her was seeing a man locked up as I was, and perhaps the actual sex acts she was going to experience. But there was obviously no regard for me; I was merely another easily manipulated guy. I tried to focus on what Donna was saying as Cindy's soft little hands lightly traced my balls and the parts of my penis that had swollen through the vent holes of my CB-3000. Then she hefted it in her palm and turned it this way and that.

Donna continued, "I've been doing some studying on what we've been doing. It seems that it's not entirely healthy for you to build up all that semen inside of you without getting to expend it." She could see the wheels turning in my head...was I going to be allowed to cum? As she removed an item from her workout bag she shook her head at me, "No dear, you definitely will not get to cum. There is a solution to the problem that won't let you down off of your high, and Cindy and I are going to administer it now. I don't want to do it this evening...things will start as soon as you get home, and I will not have my plans this evening postponed. So we will have to do it here and now." The item she had removed from her bag was white and looked like a thin, curved dildo with a handle at one end.

My attention was diverted momentarily as Cindy tugged my cock away from my body, her cherubic face looking up to mine from my crotch, "Does it hurt you?" No pretense of actually caring whether or not it hurt me or not. Just obtaining information. If Donna let this girl loose on me she was going to be dangerous for me. Donna cared about me...this girl would just plain USE a guy for herself. My cock pulsed in the hand at the thought, "Yes, ma'am, sometimes. But it is not unbearable, and the arousal deadens the pain."

"Get up on your desk on your knees and elbows." Donna brought my attention back to her. I obeyed, trying to be quiet. Once I was in place she removed four small hand towels from her bag and placed them, folded, under my knees and elbows for my comfort, "you may be here awhile. I'm not sure how long this takes." I dared not ask, but my mind screamed WHAT?! WHAT ARE YOU GOING TO DO?! She then removed a ball gag from the bag and handed it to Cindy, who put it in place as Donna spoke, "We wouldn't want you crying out", she paused, an amused look on her face, "Or just crying. Wouldn't want you attracting the attention of your friends."

Now, I want you to place your head so that you are watching Mr. Happy. I don't want you to miss this. I did as I was told, and could see the two women moving around at my buttocks through my legs. They spoke in matter of fact tones about the process as Donna pulled on rubber gloves, gesturing for Cindy to do the same. Soon Donna was rubbing lubricant around my asshole, then penetrating me with her fingers. She moved her fingers around inside me and then removed them, telling Cindy to give it a try. Soon smaller fingers were exploring my ass. I watched as Donna picked up the strange tool and lubed it up.

I drew in my breath at I watched Donna press the tool firmly against my anus, gently pushing it in further and further until it had all but disappeared. She was now holding onto it by its curved handle. "mmmmppppphhhhh", I moaned around the gag, but apparently did not draw the attention of either of the women. Donna slowly began moving the item around inside of me until she heard me moan lowly in pleasure. Then she concentrated her efforts firmly on that spot, turning to Cindy, "What you are supposed to do is massage his prostate with your finger or with this until you get the desired result. It should take several minutes. Do you want to do it?" Cindy took over, taking hold of the item and fumbling a moment until she got a rhythm going, moving to stand directly between my legs. It felt great, and my head came up as I groaned in pleasure. Donna, who had moved around to the side of the desk, reached underneath me and twisted my left nipple, hard.

"MMMMPPPPPHHHHHH", I tensed, shocked. Donna leaned down near my face, "I told you to watch." I returned my head to where I was looking between my arms at my straining cock and Cindy between my legs. My ass was pointing up into the air, exposed and vulnerable. My caged member giggled and gyrated as Cindy moved my ass with her ministrations. Donna sat in my desk chair and took in the show, watching my bouncing cock intently.

This went on for several minutes, and I have to admit the massage of my prostrate felt very good. It really made me want an orgasm all that much more. I was very relaxed, enjoying the attention from the young girl behind me, even if I it was occurring on my office desk, with a dozen people on the other side of the door.

My pleasure suddenly turned to horror. Oh, my God, NO! I wasn't feeling anything anywhere near an orgasm, but I actually whined in near panic as I watched semen begin to flow from the head of my caged cock, dripping in a stream onto the desk below me. Donna saw it too, but her reaction was far different from mine. Her eyes lit up and she got all giddy, "It works! Cindy, Cindy, look, it works!" Cindy leaned around and looked at the fluids emanating from my cock, then looked at me, "Are you cumming?" No emotion, just obtaining information in a sweet, youthful voice. It was if her asking the question put the fact into reality for me. I had been staring at myself in disbelief until she had asked that question. Now I shook my head slowly in the negative and found that Donna had been right. I couldn't control the semen flowing freely now from my cock, and I couldn't control the tears that streamed from my face as I cried silently.

Donna stroked my hair gently, trying to soothe me while turning to Cindy, "Keep going, there has to be quite a bit. He's been leaking precum almost non-stop, but he hasn't cum in nearly a month." It was ironic. My wife stroked me lovingly to calm me, but at the same time insisted that I continue to watch the very act that was making me cry. I'm not a wimp, but DAMN IT! I deserved to cum! And now all that built up cum was streaming uselessly onto my desk and I couldn't even feel it. Other than the feeling of liquid swelling through my urethra, I didn't get to enjoy the orgasm I had waited so long for. I watched as a seemingly endless flow of my juices poured out onto the desk, creating an ever-widening pool of milky white fluid.

Eventually the stream slowed to a dribble and Donna motioned for Cindy to stop. Donna then helped me as I awkwardly got down off of the desk, standing there in shock, staring at my own cum and then at the ladies. Donna wrapped the tool in one of the towels, placing it all back into her bag. She motioned for me to remove the gag and give it to her, and then she put it back into the bag also.

Donna looked around as if searching for something, "what are we going to do with this mess he's left now?"

Cindy now giggled like a mischievous schoolgirl with an idea, looked at me, then at Donna, "May I?"

I looked back and forth at the women as Donna said, "Sure, be my guest."

Cindy moved over by where I stood, smiling at me. She reached up and grabbed my hair, interlacing her fingers in it. Then she pushed my head down very close to the desk. She stopped momentarily, pulling my head back up, looking at Donna, looking as if she had discovered a new problem, "What should I call him? He's so much older than me that little boy or his first name don't sound right." Donna shrugged her shoulders, then it seemed a light came on for Cindy as she pushed my head back down unceremoniously, "Oh, I know" giggling, "Clean it up, Mr. Bryan! Don't you miss a spot!" I obeyed, sucking and licking up copious amounts of my own cum as Cindy continued to hold my hair tightly, moving my head around as if she were guiding a vacuum cleaner. Donna looked on in amusement at my humiliation at the hands of this young vamp.

After I had finished Donna used another one of the towels to wipe my face dry before returning it to the bag. Then she directed me to put my pants back on. I was still shaking as I followed her she and Cindy out of my office.

Donna stopped and turned to me as if we had just had a conversation about a trivial personal matter, "Thanks honey", moving closer to kiss me briefly, "We'll see you after work! Don't forget we've got company coming over." Then she turned and they both walked past my co-workers, exchanging pleasantries.

I returned to my office and sat heavily into my chair. Staring off into space, I contemplated what she could possibly have in mind for me this evening. Beth walked in to ask a question and I struggled to at least appear normal....