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".

When I got back downstairs my heart immediately began racing. Donna, Cindy and my friend Terry were all sitting in the living room. But that isn't what caused my nervousness. Sitting in a corner of the living room was the "project" that Terry had completed awhile back in MY workshop. It was covered by a cloth, and had been since its completion. I knew it was some type of chair, and I knew that it was meant for me. But that is all that I knew. My nerves were on edge wondering what was going to happen to me.

Donna, sitting on a love seat, noticed me and patted the space beside her to indicate that I should sit. Cindy and Terry didn't comment on my attire, or lack of it, as they were both well accustomed to seeing me naked by now. After I sat Donna pulled me to her, laying my head against her bosom. She traced her fingertips on my lips, then trailed them lovingly down my chest to my manhood. She playfully toyed with what little part of my sex that wasn't covered by my CB-3000. Hefting my very full balls and inserting her fingernail into the vent holes of the device to tease my purple tortured cock. She continued to softly caress me as she spoke.

"You may get to cum tonight, my love." I think my heart stopped. "You have been celibate for month now, and this little party will include many of the people that have shared in your experience. So it would be the perfect time. However, I feel it wouldn't be any fun if we didn't make it interesting; if we didn't put a little bit of playfulness into it." I looked into her eyes intently, as if she held my very life in her next sentence. "Whether or not you get to cum tonight will be entirely up to you and your powers of persuasion. Well...persuasion and the abilities of your magic tongue, dear." She paused, playing with my chest hairs and leaving me hanging, building the anticipation.

The she reached out and lifted something from the end table, a small box. She drew from the box a short chain with a roach clip attached to one end, and the other end to a weight, a weight like those used in fishing. "There are going to be a total of twenty guests here tonight, and Terry has put together twenty of these weights for me. When the guests begin arriving, you will answer the door for each of them, and give each of them one of these weights. Now, the first two hours of the party will be sort of a time for everyone to get acquainted. You will be serving drinks and finger foods. After that two hours everyone will be free to get frisky with one another. Everyone but you of course, you will still be 'serving', just in different ways. Now, in that first two hours is your opportunity to earn your orgasm. Yes baby an orgasm. I will explain to our guests. If in that first two hours you can persuade every guest to let you try and make them cum with that wonderful tongue of yours, and if you can make them very appreciative of your talents, you should end up with all twenty of these weights..." With that she reached down and attached the clip of the weight she held to the chain connecting my nipple clamps. "If after those two hours I count all twenty of the weights here, then at the end of the evening all of your friends will get to watch you have a glorious orgasm. If you haven't managed to get all of the weights, then who knows when you will cum? It may be another month before I can get everyone together at once again, sweetheart."

I tried to take it all in. Could I make twenty women cum in two hours? What if one of them was a bitch and wouldn't let me even try? I was pulled from my thoughts by Donna's voice as she took the weight from my chest.

"I think you should present the first two weights to the guests that are already here, dear, then you can give the rest out as the guests arrive." She handed me two of the weights and I stared at them for a moment, then I looked over at Terry and back to Donna. Damn. "Ma'am, uh, how many men will be here? I hadn't thought of that, ma'am"

Donna twitched my nose playfully with one of her forefingers, "I think there will be about five men total honey. Will that be a problem? How badly do you want to cum dear?" I looked over at Terry again, nervously, then back to Donna, "No...it won't be a problem, ma'am, I'll do just about anything at this point." It wasn't as if I hadn't already sucked a cock since our escapade began.

Cindy chimed in for the first time; "You'll do anything? Kewl!" God only knows what was going through her nineteen year old, devious mind. I reddened and they all got a good laugh. After I calmed a little bit I stood and carried the weights over to where Cindy sat on the recliner, one incredibly sexy leg draped over one arm of the chair as usual. She lifted her chin regally, indicating that I should fasten it to the necklace around her sensuous young throat. I did so gently; she smiled at me and said, "Why thank you, Mr. Bryan." I walked over to Terry and he simply held out his hand, "Thanks, buddy. I'll try not to be too hard on you." He placed the weight into his jeans pocket.

Just then the doorbell rang. Donna drew out a weight for herself, and then handed me the box. "Well, I guess you better start greeting our guests, huh, baby?"

I answered the door to find that the first guest to arrive was Susan, Donna's best friend. Susan had been involved in my torment early on, and I knew her intimately, although my penis didn't. She walked in, taking in my "outfit", and kissed me briefly on the lips. She began to turn and walk into the living room, but I gently touched her arm, "Ah, Miss Susan, I am to present this to you, and Miss Donna will explain later." I handed her a weight; she smiled mischievously and went on her way. I waited for the next guest.

Next to arrive, to my surprise, were Elizabeth, Audra, Mary and David, all from the conference where my chastity and teasing odyssey had begun. Donna stood and walked to the front door, "Hi, I'm Donna! How nice to meet you all in person finally." They all introduced themselves, and then Donna instructed me to give them their weight, saying that she would explain in a few moments. I stood nervously by as the door was still standing open, and I was the only person standing there in the nude. Finally David reached over and closed the door. The women all looked fantastic! Elizabeth and Mary both wore very sexy evening dresses, and as I took in Audra's attire I could hear Donna laughing playfully at me because my poor imprisoned cock suddenly lurched upward at the sight of her. Audra is endowed with very large, lush, natural breasts. They were absolutely perfect with large dark aureole. Audra noticed me look at her, saw my face flush and me looking down, trying to compose myself. She then noticed Donna looking at me and grinning. Self-conscious, she glanced down at herself and asked, "What?"

Donna touched her arm reassuringly, "You're fine, honey. I think without knowing it you combined two things that would drive my poor hubby absolutely wild. I'm sure you are well aware of your natural charms, and then you've gone and encased them in a wispy, low-cut, white sundress, his favorite!" It was true. Audra stood there with her plush tits pressing against the taunt fabric of the sundress, which continued down over her luscious hips and to just below her knees, where it danced around her beautiful legs with each movement she made. She held her hand over mouth, feigning regret at her unintended effect. Then she stepped closer to me and gave me a hug, making sure her breasts were pressed tightly against my chest as she breathed into my ear, "I missed you and your tongue, Bryan. You poor baby." As she said it she reached down with one hand and hefted my straining member, inadvertently covering her hand in the precum that seeped from the cage. She looked down at her hand and grinned at me seductively. Then she raised her hand and sucked each finger in turn while maintaining eye contact with me. I almost crumpled.

David looked down at my manhood, swollen against the confines of its plastic cage, the CB-3000 that had become its home. "Mr. Happy" swelled through the built in vent holes where he could, and pressed tightly against the inside of the tube where he couldn't. My balls were full and tender. Precum dripped occasionally from the tip of the cage, running down my legs. I knew I looked like a complete mess, and I was. I had been continuously tense and on edge. David looked up at me, "Holy shit, man, have you been locked in that all this time since the conference?" I flushed again and nodded, he shook his head, "You poor Sonofabitch, I mean, damn! I would have lost my fuckin' mind by now. How the hell do you do it?"

They all listened for my answer. I'd had to explain this before, but understood why I kept getting asked the question. I explained about the intense and contradictory feelings of needing to cum desperately as opposed to the incredible, constant sexual high that chastity and denial gave me. "You know how it feels just before you lead into an orgasm? When all of your senses are focused on your sex and the need for relief? I've felt like that almost constantly for the last month."

Liz grinned mischievously, "Why Bryan, you sound almost as if you don't want to be let out at all."

Sweat popped up on my forehead and my heart raced. I knew they were just teasing me, but by this point I was so desperate that I couldn't convince myself completely that my reward might not be taken away from me so easily, "No! No, no, I absolutely want out. Its just...have you ever heard of the Stockholm Syndrome?" They had. "It's sort of like that. I've grown so accustomed to the constant pressure on him that the cage feels like it belongs there..."

The doorbell rang again so they all went on into the living room so I could answer the door. Towering over me was Lamont, grinning down at me with Becky on his arm. Without wanting to, my mind flashed back to the image of Lamont at the club, fucking the daylights out of my wife with the biggest penis I had ever seen while I was bound above the bed. I could hear Donna's cries of ecstasy echoing in my ears. I looked down in embarrassment, but that didn't help. Lamont was wearing loose fitting khaki slacks and obviously no underwear, because the huge slab of meat that hung from his midsection and snaked down his left leg was outlined and very prominent for anyone to see. I turned my head to avert my eyes from the horrific sight. Lamont laughed out loud at my awkward response, "You're funny, boy...its not like you aint seen it before." Becky stepped forward and took my head in her hands, leaning it sideways so she could kiss me long and passionately, as she had that first time at the club, out tongues dancing together. "Don't worry, baby. You might not have an anaconda in your pants, but you definitely have your redeeming qualities." Embarrassed and on fire after that kiss, I handed each of them a weight without being able to say anything and they moved on. I was just shutting the door when Roy, Lamont's friend, pushed it back open. "Hold on, bucko, I had to park the car." As I handed him a weight, he glanced down at my predicament. "Still!? You crazy motherfucker...aint nobody gonna lock up my dick! Course, nobody'd want to lock up my dick!" He walked off laughing.

A couple of people that I didn't know arrived, which was even more embarrassing since they could have been "drop in" visitors that didn't know what was going on. That got me worrying about if somebody like Donna's mother dropped by, or God forbid my mother. I started looking through the peephole before I answered the door now!

The last to arrive were Stephanie, Fran, Jeff and Dave, all of whom I had "met" briefly at the club. At the time I had been fastened to an eye bolt in the floor by my balls with a set of handcuffs. The four friends had stood around me as I stared at their waists and held a conversation with me as if I wasn't in such an awkward position. Then the ladies had used and taunted me. Tonight I couldn't help but notice that Fran's world class ass was just barely covered by light silky shorts. Damn!

Now that everyone had arrived, Donna called for their attention as I went around refreshing drinks and offering snacks. "I'm glad everyone could make it. Not nearly as glad as Bryan is, I'm sure. Tonight is Bryan's 'Cumming Out' party, if you will." Liz was sitting near where I stood and playfully smacked my butt as Donna continued, "He has now been locked up for an entire month—he hasn't cum once in the time that most of you have met him. Tonight, if he earns it, you will all get to watch him get what he's given most of you. But first..." She held up her weight, "Bryan gave each of you one of these weights when you arrived. Beginning now, Bryan has two hours to convince each of you that you should let him make you cum. If you consent, and if he does a good job, simply place the weight you were given on the chain between his nipples. If after the two hours are up he has managed to collect all twenty weights, he will get to cum before the night is over! If he doesn't get all of the weights, he will have to wait until our next gathering, and who knows when that will be?" She went on to explain that for that two hours they would all have dinner and chit chat while I tried to earn my reward. She motioned for me to come to her, then turned me around so that I was facing everyone, "You won't have to serve drinks and such for your two hours, baby. And it doesn't matter how you make them cum, except of course that you can't use Mr. Happy." She picked up an alarm clock from the fireplace mantle and set the alarm for two hours, "Now, I suggest you get busy, lover!"

I immediately turned around and knelt at Donna's feet, looking up at her beseechingly. She smiled and patted me on the head, "I won't be the one to cause you to forfeit, honey. I really want to see you cum. But I think you should offer yourself to all of our guests first, don't you?" I answered, "Yes, ma'am."

I turned back around and saw that the nubile Cindy was closest to me, sitting on the couch. I stayed on my knees and went to her, "May I please you, ma'am? Please?" She spread her youthful legs and motioned me forward. As I began to pull down her shorts she stopped me, pulling me closer to her between her thighs and lifting my chin upward to look into her eyes. Teasingly, her nineteen year old eyes lit with mischief, feigning a Scarlet O'Hara tone, "Ohhh, I don't think I'm in the mood quite right now, Mister Bryan. Maybe in a bit if I can work myself up for it." Inside I was calling her a brat and a bitch, I wanted to beg, but knew it would be waste of time. She was enjoying the tease too much. "Yes, ma'am. Please don't forget me, ma'am." She ran her finger along the chain linking my nipples, tugging it gently as she gave me that coy little girl smile. "Oh, I'll try not to Mr. Bryan", then tapping my cage with her foot as she looked around the room, "Its just that there is so much hot cock around here tonight. I hope I'm not all used up before you get back to little ole me."

Sitting next to Cindy on the couch was Mary. Sweet Mary of the south Texas accent that drove me mad every time she spoke. As I looked her way she smiled at me, "Come to mamma, baby." I moved over in front of her, still on my knees. She leaned down and kissed me tenderly as she caressed my shoulders and my chest. Then she stood and guided me into the adjoining den where she had spotted the psychiatrists couch we had bought years ago, not thinking of this use, but it was perfect. She licked her lips as she wriggled her hips, pulling her tight dress up over them to reveal that she wasn't wearing any panties. She lay down on the couch and beckoned me to her. As I delved my tongue into the satiny lips of her sex I realized that she was already soaked. The entire time I was making passionate love to her with my mouth and tongue she spoke between moans of pleasure, making my heart race with that husky southern voice of hers. Without any other influence my cock would have throbbed just as hard against its prison, straining in vain to become erect as she spoke, "Oh, Bryan, ah have looked forward to this so damn much...mmmppphhhhh.....Oh Gaaawwwddd...yeeesssss....this whole thang has made me such a hawny fuckin' bitch....mmmmm....that's it....ya'll are so goood at this." I sucked gently on her puffy nether lips, one at a time, then ran my flattened tongue up and down her slit before darting it, pointed, across her clit. Up and down, back and forth, then massaging it tenderly before lashing it again. She grabbed my hair, grasping it in her fingers as she bucked against my face, fucking me with her glorious, glistening pussy, "Gaaaaawwwwwddddd......mmmmpppphhhhh! I almost wish it wasn't coming so fast, but I'm soooooo ready.....YES! Oh God! Oh, Gaaaaawwwwdddd, MMMMMPPPPPHHHHH" Her thighs pressed tightly against the side of my head, I tried desperately to stay on target, to draw out her pleasure as long as I could, "G-G-G-G-AAAAAAAAAAWWWWWWWWWWWDDDDD DDDDAAAAAAAAAAAMMMMMMMMMMMMNNNNNNNNNN!!!!!!!!!!!!!" I thought she was going to pull my hair out! She stopped squirming but held me fast to her sex as she slowly calmed down from her incredible climax.

When Mary and finally recovered she let me sit up and lovingly straightened my hair, caressing my face, "Aww, baby, thank you. I know I can't keep you right now...but before I leave Sunday you have got to give me more of that....promise?" She clipped her weight to my chain, and I felt a tug against my sore nipples. I snuggled against her bosom and told her that I wanted to very much if Miss Donna approved. As I looked over I saw that several of the guests were looking into the den now, some trying not to be obvious. But apparently Susan wasn't worried about being bold as she strolled purposely into the room, "Now, that sounded good...move over Tex, I'm next...."

I noticed that there was an ever-growing pool of seminal fluid forming below my caged manhood on the floor as Susan unceremoniously pulled me to her snatch. I was in heaven. All of the women at the house that night were beautiful, and I enjoyed going down on them tremendously. And fortunately for me, hearing the others having orgasms seemed to wind them all up so that my job was easier, which was great since I was on a time schedule. As an example, Susan seemed to begin her orgasm almost as soon as I started lashing her clit with my tongue, only to be replaced by another woman. Also fortunately for me, they were each more than happy to give me a weight to add to my chain!

After I had managed to bring four women and one of the men to orgasm, collecting my reward on the couch in the den, no other guests entered the den. I looked towards the door nervously. The clock was ticking, and I still had fifteen orgasms to cause. Soon Cindy appeared, leaning against the doorframe, playfully holding one finger up to her mouth as she spoke, "I kinda talked everyone into taking vote, Mr. Bryan." She smiled mischievously, "We think its not fair that you are in here where we can't see you work, and that you need to be in here beg...I mean asking people to let you get us off." With that she gave me a little wave and disappeared.

I moved hesitantly into the living room to find everyone sitting around talking. I could see some of them were in the kitchen getting drinks and talking. As I scanned the room I spotted Roy signaling for me to come to him where he was sitting on the love seat, Audra sharing it with him. I walked haltingly to him as I watched him unzip his pants and lower them to his ankles, grinning at me. Audra honestly looked sympathetic to me. He pointed for me to get on my knees and get to work. I was so humiliated. I have no attraction to men, and certainly no desire to suck on cock. But I would do anything my lovely wife wanted me to do when we were in domination mode. And honestly, abject humiliation is part of the rush of being chastised and dominated. That's what made my cock twitch in its cage as I took Roy's fleshy cock head in my mouth. I stopped for a moment, collecting my courage...damn I needed to cum...I can do this. The spongy head flared in my mouth, contrasted by the rock hard shaft. I felt Roy's hands on the top of my head, "Come on white boy. Remember, ya gotta make me like it." I took as much of him into my mouth as I could, then took him out of my mouth, bathing his cock head and shaft with my flattened tongue. I was trying to imagine what I would want done to me. I felt Audra's soft hands caressing my shoulder, trying to comfort me. I reached up and traced my fingers lightly across the underside of Roy's heavy testicles while taking his cock back into my mouth, sucking as much of his manhood in as I could, then releasing it. I tightened my lips around him and began bobbing up and down, running my tongue along the underside as I did so.