Descent into Slavery, Part III

Part 3: Roxanne

It has been a little over a year since I got that call from Claire that eventually brought Alese and James into my little family. We hadn’t met at that time, but had become acquainted as mutual friends of James on-line; two women who had been introduced by him into the BDSM lifestyle.

It had been marvelous finally meeting with her, and exchanging stories about this exceptional man we both knew so well, but from such completely different perspectives. What she told me that day about him changed everything; and created a wonderful opportunity.

James and I had met through a kink site, as he had moved back to DC a few years before. I was very new to the lifestyle, living a few hours to the west of DC, but based on our common interest and attraction, we met, and he quickly became my mentor and trainer. Over a period of a few months, he proved to be a gentleman, a valuable friend, as well as a gifted, experienced, and generous, kinky mentor. I developed as a submissive, but the more I did so, the more it became obvious that my true heart was that of a Domme. He lovingly brought me along, helping me to understand – coaching his very attentive pupil in both technical skills, as well as the finer, much more important mental aspects of dominance and submission, often serving in the role of sub, providing a full, realistic experience. Even then, I strongly suspected that he was at least a switch.

I am sure that he could see within me, and helped me to develop my own innate understanding and interest; the feel, satisfaction, and sexual fascination in having complete control of a submissive. I loved objectifying them; dressing them up in amazing, humiliating outfits and using them. I loved to discipline; and to feel them break under my whip or cane. Most importantly, I loved their dedication to please and obey me; the intense love which that represented, and the look of ecstasy in their eyes as I pushed them deeper into that submissive zone they craved.

Greatly complicating our relationship at the time was my own confusion regarding what I wanted in a man; and that I fell in love with another, exclusively Dominant male whom James positively hated. At that point in my development, although I didn’t understand it at the time, I think that deep down, I could only truly love a man who was 100% dominant. Because of that, James was hurt and we parted company on difficult terms.

Now, only a few years later, I was being given the opportunity to take James as my slave; and in learning from Claire that his desires had become overwhelmingly submissive, I was very, very interested. He is, after all a great guy, and a good friend. But to also possess his heart and soul in this kinky way appealed to me at a very base, visceral level. Once again he would be my very good friend and confidant, but I also sensed that based on personal growth we had both experienced, there could be something much deeper and I had to try to understand what that may be.

Of course James also loves Alese more than ever, as I encourage, but carefully manage within our poly family, and I even allow them to sleep together on occasion, with him locked in chastity, of course; but that's rare. More than anything, Alese needs a wicked, sadistic Dom to use her periodically; and God, I've never seen a girl squirt and orgasm so hard; a role that is also filled very well by others.

Sure, she does still love James in a manner of sorts, and truly didn’t mind his smallish penis, but now that she's completely converted as a “size queen”, she could never be satisfied with him again, even if I allowed it. Most importantly, she's my number one, submissive girl; obedient, devoted and loves me without question or limit. I'll never let her go.

Once he was “broken in” as a slave, as a kind of “graduation exercise”, I introduced James to our group here in DC. This small but growing group of dominant women formed the club several years ago, and it’s evolved into quite an interesting group that meets about once a month.

The club consists primarily of dominant females; mostly professional women who enjoy being served by both submissive boys and girls, but most of us also have a dominant boyfriend or husband. Speaking for myself, I do adore my submissives, and love my little family which I do head, with the permission of my wonderful husband, Peter.

We are both attorneys – and I know it sounds odd, but we’ve never really lived together; he in New York, lead counsel for a large corporation, and me here in DC representing a non-profit. It’s worked for us well though, and our time together is always exciting and fresh. We are also in perfect synch as a “Dom-Domme” couple, he keeping the cute little submissive girl I found for him, Jennifer, and me now with Alese, and little James, who has also taken a special place in my heart.

Back to little James, it was such fun to take him to a party the first time. He didn’t realize it, but had so much more to learn than he had during his and Alese’s first month in my home.

Perhaps most delightful, from a pure “wickness” perspective was that I had arranged for several of James’ former friends (when he was “pretending” to be a Dom), to be there, to see him put “in his rightful place”. I knew this would be harsh, but I also knew it was exactly what he needed to make the final transformation from who he thought he was before.

At our club, all submissive boys and girls are recruited with service skills, appearance, and the desire to “serve” as extremely important, so James's talents were highly valued.I knew he would fit right in, but first he needed to truly learn his place. I was confident he would adjust to what he truly was and has become, a cute, devoted, hopelessly submissive, and proud cuckold boy!

I also do so love making straight submissive boys suck dick, and with James, it was even more enjoyable than ever! That moment when their mouth is filled with male spunk for the first time as they look up at me is just priceless!

When we arrived at the party a few minutes early to prepare, he was stripped like the other 3 unattached submissive boys present that evening, and once inspected and measured by the head slave girl, Peter’s Jennifer, was fitted with a thick leather collar around his neck and genitals; enabling a leash to be attached to both, and matching wrist/ankle cuffs. Jennifer then went down the line and popped a little blue pill into each boy’s mouth to keep them their hardest all evening.

He looked so cute, with a bewildered look on his face, wondering what was coming next. As always, he was completely clean-shaven, with the exception of his eyebrows and very short crew cut.

Of course for the previous month, as with the other sub boys, he waskept locked in chastity 100% of the time, his key held and controlled by Alese; but now, once bound, I had to laugh as Aleseunlocked his little “dicklett” so all could view him in his tiny glory; seeing the look of panic in his eyes as he looked to his left and right at the others.

Yes, he was the "smallest" by far!! As his “special honor” for being that evening’s “littlest”, his collar was switched from black, to pink. He would soon learn what that meant.

He was soon kneeling alongside the other boys in two neat rows at the entrance, with wrists locked behind their backs – all with very stiff dicks at attention honoring the arriving guests.

Since little James was new, and likely to try to flee, based on what I had in store for him, I also had Jennifer fit him with a short chain from his genital collar to his ankle cuffs. He knew already that he had to remain on his knees, but this would prevent any flights of panic, to which he was prone. Lastly, since I was training him in a special way, I had Alese bend him over slightly to take a slightly larger ass plug to keep him at his most attentive. This evening would be important for him, and I wanted him at his best.

Guests soon began arriving, among them my long term partner Peter, whom I naturally had prepared in advance. He was looking forward to having my new, pretty slave and enjoying the humiliation of her newly "cucked" boyfriend.

After greeting him, I got Alese's attention, snapping my fingers and pointing at his feet. Instantly, she was kneeling at her rightful place, fetching in a tight corset that just exposed her hard nipples, thigh high stockings and heels – her smooth shaved sex exposed and available.

He took his time inspecting her, stroking her hair, and reaching down to pinch a nipple, making her squeak and jump!

"This is a pretty one darling", he said, raising her to her feet and drawing her close, possessively holding her pretty bare bottom with his hand. I could see the humiliation in little James' eyes, fixed on the floor at Peter's feet, and put my hand on his shoulder, leaning down to whisper to him.

"I know its difficult James, knowing that your love will be given away."

I knelt beside him, reaching between his spread legs, cupping his balls just as Peter kissed Alese for the first time.

"You know this is the way it will be, and what you've dreamed about; but the reality can be just a little too harsh; too stark and painful at times can it not?"

He had difficulty speaking, perhaps his sensesa bit overloaded, his lovely former girlfriend and slave being fondled just feet in front of him, and obviously enjoying it, while his own sex was toyed by his Mistress.

I felt sorry for him and told him that he could look into my eyes.

He finally looked up at me; stammering, in a whisper, his voice breaking,

"Yes Miss...it is hard".

"Yes little James...but this is for you and for Alese too...she will be satisfied tonight for the first time by her new owner; her Master now and forever; and as you know... it will be so much better for her than before, with you...you know that don't you?"

The poor thing looked like he was going to cry as he said so softly,

"Yes Miss...you're right"

At that moment, an evil thought popped into my wicked mindso I added,

"You'll be rewarded later tonight if you're very good as we’ve talked about", stroking his swollen genitals; which were so needy after several extra days of service and chastity. I finished by giving his balls a hard squeeze, making him squeal like a girl.

I so love making boys do that.

And how funny; by his glowing look, he actually thought that he might be "rewarded" by being able to fuck his girlfriend; something I had implied and held in front of him like a carrot, for VERY good behavior during the past month while he was broken in and acclimated to his new life as a slave. He would learn the bittersweet truth that his reward would be very different that evening and in the future. Bittersweet because although he would never have sex as a man and “Master” again, his rewards as my slave would be equally satisfying in their own way.

As he refocused, he realized that Peter, with his arm around Alese and hand gripping her tight ass, had taken out his cock and presented it to James, saying, “To do this properly, you must ask me to take your girlfriend as my slave, and worship my cock little cuckold”.

Peter was an experienced Dominant male, and was well accustomed to using submissive wives and girlfriends of submissive cuckolds – and was always amused at humiliating them.

I was still at his ear, holding his balls, “Do it James, she is his now, and you must obey.”

Resigned, he said softly, eyes down at Peter’s shoes, “Yes Master, please take Alese as your slave”.

I had to push his head a little, but he then obediently leaned forward, and began to worship his new Master’s cock as he had been taught; licking first the balls, then the entire shaft, until all was shiny with saliva; finally taking the head into his mouth and sucking, eyes up at his Master, submissively awaiting further instructions. Peter smiled, kissing Alese deeply as his cock was sucked, enjoying the sensation, placed his hand at the back of James’ head and pushed his cock into his throat, making him gag, causing Alese to giggle, then abruptly withdrawing his cock, left James to gasp and struggle to regain his balance. Zipping up his pants, Peter whispered something to Alese, who smiled, leaned down, patting him on the head, smiled and said,

“Now be a good boy stubby!”

We left him kneeling there, in line with the other subs and entered the main parlor of the house with Peter and Alese arm-in-arm.