The Setup

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Fridays I was simply required to take Amber and her girlfriends out to the clubs, and be their designated driver and escort. I spent many hours in the car, butt plug and panties in place (as had been her demand), waiting to take home a group of beautiful, drunk young women who all giggled ferociously at my state of frustrated and pathetic servitude. After dropping them off, I'd get home at 3 am, exhausted and crash immediately, my mind and body permanently numbed.

But after the relative ease of Fridays, Saturdays were by far the worst. Elizabeth was the most invasive with her desired "training" methods. She got word from Katie about my feminization and took it to the next step, through slowly and steadily fucking my ass with her strap-on, all the while making me moan, whine, and beg for more. She just laughed, occasionally smacking and kneading my ass cheeks. It was utterly humiliating. Dressed in a skirt, panties, bra, stockings, heels, and a wig, with full makeup, she'd do me doggie style... each Saturday evening. She'd comment on how great this all was. And how she never let me fuck her anally, or even doggie style, yet here she was, totally owning my ass, and loving every second, while I could not even get off. I dripped pre-cum the whole time, but never came, though sometimes I felt close. And my ass was usually sore until the next Wednesday, but it was becoming more accustomed to the stretching. And honestly, the rhythmic penetration didn't feel that bad. In fact, given my chaste situation (beggars cannot be choosers after all) the contact felt rather enjoyable, though I'd never admit that to any of my tormentors.

And so, with my fevered horniness pushing farther and farther past red-line, this routine continued on for a month. Early on, I had decided that I should try my best to please them all, potentially earning my freedom. And as the day gets closer, I can only hope for a good report card from my instructors.

PART 17

When the big day came and I was shocked to find out that I had received straight C's, and would not be getting out this month, unless of course, I wanted to give a nice, juicy, enthusiastic blowjob to my ex's newest stud...

"But I did everything they asked, to perfection," I pleaded to Jessica.

"Yes," she said with a huge grin, "but everybody knows that just doing the minimum only earns an average grade. To get higher grades, you need to show initiative, and go well beyond the minimum expectations. And to get A's, well, let's just say that you need to be spectacular in your efforts."

I was crushed, and sat silent.

"I'll try harder next month," I said solemnly, shaking from my permanent fever of horniness.

And I did try harder, oh did I try hard!

I began giving them all foot and back massages at the conclusions of our sessions. I subscribed to women's fashion magazines in order to study the latest styles. I bought an assortment of makeup and experimented on my own, each time showing up with new colors and perfume. My cross dressing was becoming quite good. I could strut effortlessly in heels and had some great dangly hoop earrings which moved about just so while vacuuming. I cleaned their vehicles. I blew their strap-ons with reckless abandon, and was even able to impress by deep-throating (after many hours practicing alone at home). I asked, no I begged, to have my ass fucked with an even larger dildo. And I never complained once, about anything. In fact, I was becoming accustomed to the routine, almost hypnotized by it, reveling in it. If anything it was an escape and after so long, the escape was all I knew. I couldn't even remember my former self, and my foggy arousal was endless. My resistance was nearly gone.

My second report card was better but also disappointing; there would be no release for me this month. At the news, I openly cried and fell to my knees begging Jessica to release me, saying that I'll do anything.

"Anything...," she asked, with a knowing, victorious smile.

PART 18

Going into the third month I knew deep down that no matter how well I perform, the girls are not going to let me out of the device. I believed fully that my only hope was to beg Jessica to let me blow her guys, and maybe, just maybe, she'd honor the original deal and let me out.

I was ruined, defeated, and in full acceptance of my destiny. It wouldn't be so bad. In fact, I had a stirring feeling that was becoming more and more prevalent; I actually wanted to suck cock. The contact and intimacy would be most welcomed, and truthfully, after all I have been through, it seems quite natural and even sexy.

And so, again going above and beyond all expectations, in addition to serving my ex's as I am, I began begging each of them to find me a guy to blow! If I was ever going to get out of this device, full committed enthusiasm was necessary. I pleaded and explained how I actually want it now, and even need it. I explained how I've been keeping my hands extra soft and moisturized, to enhance the pleasure I might someday give to a man... how I'm more attentive all the way around, and eager to please... how I've come to crave being used... and how I've been dreaming of sucking cock most every night, only to wake feeling so empty.

Word got back to Jessica, and she was over pleased!

"Oh sweetie, I'm so glad that you've finally come around and embraced your true self," she said, beaming. "This is really a rebirth for you, and you should be very proud and excited. I am."

"Yes, I suppose that you have won," I said. "You knew my true self and what I needed, even if I didn't all of this time. I guess that I do owe you a huge debt of gratitude. So thank you. I have to say, this was all very... exciting, if painful at times. Now, when can I get my hands on that stud of yours?"

"Excellent," she giggled. "Well the girls are now gathering some cocks for you to blow. I guess Katie has a lot of gay guy friends and so does Jennifer. And the others are trying as well. But again, your chance with my man only comes around once a month, so you have another three weeks to wait before I give you the opportunity to endorse my guy, and earn your release. In the mean time, enjoy yourself with the guys that the girls are rounding up for you. I'll want to hear all about it!"

PART 19

And the girls came through. I had frequent blow job dates; sometimes me going to meet the guys at their places, or sometimes me blowing them in front of my ex's, who all seemed to enjoy the sight immensely. Most of the guys preferred me to act and look feminine, so that was no problem given my recent education, yet it was still humiliating on many levels.

And I sucked like an eager champion. I really got into it, and even (I must admit), came to enjoy it. Of course I was still chaste and horribly horny and unsatisfied, which only seemed to drive me harder to perform. The contact, even homosexual contact which previously repulsed me, was a beautiful thing, and for the first time, I felt some sexual satisfaction.

Then the call came, again, like clockwork. It was Jessica, and she asked me how my month went. I explained how I've given a number of blow jobs to a number of men, and how I loved every second of it. She was ecstatic, and invited me over to sample her stud that night.

PART 20

Anticipating my release from chastity, I hurried over to Jessica's, ready and eager to do my duty and endorse her current stud. By this time, I felt like a pro, and made quick work of him, as he moaned and enjoyed my efforts, while Jessica watched the action from across the room, with a full wicked smile. As he was getting close to cumming (I was an expert now at recognizing the increased vigor and throbbing seconds before a man's climax), I stopped suddenly and said, "Please cum all over my face! I need to be coated with your delicious sperm...please do it for me!"

And he did, stroking just a bit, and blasting my lips, nose, eyes, and hair with a huge load of his hot white cum. And sitting there before him as he forcefully grabbed my now longish, almost girly hair, I proceeded too rub it around on my face, scooping some of it into my mouth where I savored the flavor.

And Jessica cheered me on, and clapped.

"Oh you are the most perfect bitch of an ex-boyfriend that any girl could ever have!" she said with pure lust and sure dominance.

To which I replied, "Well thank you, and thank you for sharing this tremendous specimen of a cock with me. You are truly lucky to have access to such a beast. I am jealous, and FULLY endorse him as your lover!"

And as I sat on the floor, a bit disheveled with his cum drying on my face and with my hint of mascara and lip gloss running and smudged, I glanced down at my crotch and then looked at her, with a hopeful pleading in my eyes.

"Yes, about that..." she started. "The good news is that I no longer have any desire to keep you locked up, or to continue training you. You have graduated as far as I'm concerned; you are now a licensed cock-sucker. The score is final and I have beaten you fully. You are my bitch and will always know that I am the women who 'ruined' you, though I prefer to call it liberation. Oh and just so you know, I did get this last session on tape, but truthfully, I have no desire to share it with anyone; it will just be my little reminder, my trophy after such a long contest of wills. Please know that I will not blackmail you, ever. I have attained my prize and am totally satisfied. But that is not to say that everyone is satisfied."

"Thank you, but what do you mean that not everyone is satisfied? Do the girls want me too continue on?" I said.

"Well yes, some of the girls do. I mean a good maid is hard to find, but that is between you and them to work out. But it is Jake, you know, the fabulous gay man with the extra large cock who's been taking a special interest in you, who's had you blow him much more than any of the other guys; his desires are the issue here. You see, he has convinced me that he wants to marry you, to make you his exclusive bitch, and after hearing his plans, I just had to give him the key to your chastity device."

"What? Why? How?" I stammered.

"Well in California, homosexual men can marry each other," she said, "and he does want to make you his wife. And I simply LOVE the idea of being in your wedding party; along with your other ex's who've already given this union their full blessing. It'll be so much fun being your bride's maids, sending you off on your honeymoon. Oh don't look so sad or worried. He said that once you are married and he's consummated the union, he'll release you permanently from you device, though if you misbehave anytime later, he reserves the right to put you back in, as punishment. I think the whole idea is fabulous, wonderful, and very fitting. You'll have direct access to as much cock as you could ever want. How wonderful for you!"

I sat still and silent. And she continued on with one last question, "So sweetie, I want you to answer me now with complete honesty. You answer will not change anything for me or you in any way, so you can answer truthfully. So, do you now actually like to suck cocks, either to please me or out of your own desire?"

Again, I sat still and quiet for a long moment while searching my mind for the honest truth before answering, "Yes, I guess that I have come to like sucking cock. There is just something about it that feels so right. I can't really explain it. Perhaps it is an acquired taste that I'd never have had the opportunity to acquire without your knowing guidance. And now, I just can't seem to get enough of it."

And she just smiled.

PART 21

And so my fate was sealed, and I no longer cared about being humiliated publicly, or anything at all, except expertly sucking cock (which now dominate most every aspect of my life) and finally getting an orgasm (hoping that my long soft cock will still function when the day comes).

The girls were all giddy and enthusiastically helped me prepare for my wedding. I had moved in with Jake and now blow him eagerly and often, while maintaining my androgynous yet femme appearance just the way he likes it. It's funny, but of all the feminine things that I've been doing, I find that wearing my slim diamond engagement ring makes me feel the most girlish and vulnerable, and owned.

The wedding is in two months, and I cannot wait (to get out of this damned device). Getting ass-fucked, providing endless blowjobs, and changing my last name to his, will all be just a small price to pay for even a single orgasm. Desperation makes a person do previously unthinkable things. But sometimes desperation can be a useful motivator to find new, glorious paths, and I owe all of my success to Jessica, who will be attending my wedding as my most beloved maid of honor.

Thank you Jessica, for never giving up on me!

THE END

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
12 Comments
donaldelliott11donaldelliott11almost 2 years ago

Previously posted by Superfly.

https://www.literotica.com/stories/memberpage.php?uid=1126730&page=submissions

AnonymousAnonymousabout 2 years ago

Would love to have a domme like Jessica except for the cock sucking. I guess fantasy is better left as fantasy.

mattpantyhosemattpantyhoseover 2 years ago

I like the idea, but I feel like too much had been pressed into one story. Each of the chapters could've been its own short story, so that the whole transformation could be experienced be the character as well as by the readers. A path from a kinky heterosexual man to a gay-bride is a really long one and should be given more attention.

The way it is the story feels too much like a draft or a more elaborate set of notes. I'm affraid I might've phrased my comment incorrectly, because I'd rather convince you to develop the story further, than discourage you from writing.

AnonymousAnonymousabout 9 years ago
Really?

If I was in that situation, it wouldn't have gotten so far as to have to do a damn thing for this trifling bitch of an ex-girlfriend. I keep my man card valid daily.

AnonymousAnonymousabout 10 years ago
Exes

As someone who has been dumped by girlfriends multiple times for being too much of a pussy I love this story. I would love to be rotated amongst my exes as their servant...massaging their feet after they get home from work, painting their nails, washing their hair, doing all their cooking and cleaning and having to be in the next room listening while their newer alpha male boyfriends fuck them. I would keep myself nice and waxed like a good little bitch in case they ever allowed me to be their man's spare fucktoy. I would offer up my smooth hairless asshole anytime I was ordered.

Show More
Share this Story

Similar Stories

Her Presents She had a number of surprises for him.in Fetish
Husband's Horny Ass An adventurous wife gives her husband a new experience.in Anal
Wife's Idea Wife teaches Hubby new tricks.in Group Sex
Party Slut Never fall asleep at parties!in Transgender & Crossdressers
My Husband’s Birthday Sexual humiliation for his birthday gift.in Transgender & Crossdressers
More Stories