I Want To Break Free 

( i )  

Spread out on my back, with my ankles and wrists firmly roped to the four corner bedposts. I was not quite naked – my wife let me wear some fishnet stockings, and a tight corset. She had some Vaseline out and was playing with my cock. As usual, I had taken a Viagra to be ready. I was stiff and moaning in her hands as she toyed with me. She was playing the long game, edging me, bringing me close, backing me off. I had no idea then just HOW long a game she was starting!

“Just look how *excited* you get in those girly things!” she teased. “I bet you’re putting them on every night, aren’t you?”

“N-No”, I lied.

“She slapped my shaft then squeezed my balls tightly – “I can tell when you’re lying, my sweet. You’ve been jerking off every night. I find the dirty tissues. And you’re always too tired to service MY needs. Have you been back on that ImageFap site?”

Years ago, I had posted some pictures of her, with her permission. She saw them online and approved! But then we let it drift, and I thought she had forgotten about it. “I think I’ll just have to check. She got out her laptop, leaving me lying there, hard and horny. “mmm, I guess I’ll search for crossdressers. Who is this with some new posts, lickher, that’s the same name you used to use…She started going through my galleries. “My, my, you are quite the flirtatious cock-sucking wannabee, aren’t you, Tiffany!”

All the while, she was tickling my balls and pulling on my cock. I was getting close again.

“Tiffany, I think you’ve been jerking off FAR too much. I noticed in your Galleries (Confession time, it’s not the first time I’ve been checking out what you’re doing late at night after I go to sleep) that you have some admiration for being put in a chastity device. Is that what you want, Tiff?”

“No, please, no,” I begged. “I just like to pretend.”

“Well, Tiffany, your little thing has not been pleasing me, and you’ve spent too much time playing with yourself. I think it’s time that I control that urge of yours!”

With that, she gave me a few more strokes, then punched me in the balls. I tensed up in pain, straining at my bonds, and my hardon disappeared. Then she started affixing a (pink) CB6000 to my cock and balls, restraining me from getting any more stiffies.

I watched in fear, horror, and disbelief as she fastened it tightly.

Securely in chastity, I watched as she left the room to hide the key. She returned and let me free, letting me know that she was out to find someone to FUCK. 

“Now I can have some fun, knowing that you aren’t sitting around crossdressing and jerking off. I’ll let you know when and how I will consider allowing you to cum. It won’t be for awhile!” she laughed, as she went out the door.

A week passed and anytime I begged or pleaded she added another week to it, so I just shut up and waited. After a few weeks more extension, she gave me the good news: She would unlock me and let me cum Saturday night! She told me to make sure I looked as feminine as possible, and to get into my best maid outfit. So I put on the works: 6 inch stilettos, black fishnet stockings, no panties, a short maid skirt and top, a little white bonnet, matching red lipstick and nails, eyebrows plucked and painted, full eye shadow and false eyelashes. Then she locked my ankles together and put my wrists together in handcuffs behind my back. I could only hobble forward. Then I heard the doorbell ring, and she had me go wait in my room.

After everyone had gathered in the living room, and had a few drinks, she called for me to come to the room. I stumbled to the entrance amid a lot of laughs filling the room. “Come here, Tiffany”, my wife beckoned. “Do you want to come, dear? How long has it been? Are you ready?”

I nodded and whispered, “yes”. 

“Louder, Tiff. What do you want?”

“I want to cum, M’aam.”

Then she took a blanket off the coffee table. It had been hiding a FleshLight, fastened to the table top. She pulled me towards her and used the key to free my aching balls. She had fed me a full dose of Viagra, and I was bursting. 

“Now, in front of everyone, we want to see you hump that Fleshlight. You have two minutes- That should be enough for you, ay miss quick spurt? One way or another, you’re back in chastity in three minutes, so I don’t really care, up to you.”

My feelings of shame and humiliation nearly made m back off,. But my brain was in my cock, and it drew me to the mouth of the Fleshlight. I was little more than my primal urges as I plunged into it. I could barely hear the crowd of people laughing and cheering me on, as I pumped, and thrust in and out. I took no notice when she locked my ankles in place at the foot of the table, securing me to that spot. I gave a few more thrusts, and felt the huge relief as the cum flowed out of my erect cock like a firehose. I closed my eyes in the extreme relief. I tried to withdraw to rest my swollen cock, but then noticed that she had flicked a switch and the device was now drawing me in, and fucking my cock. My sensitive cock was being ravaged as I realized I could not pull away. 

“Do you want it to stop, now Tiffany?” She purred?

“Yes, please, quick, please…it hurts..”

“Well, all you have to do is ask to be put back into chastity, I DO WANT it to be voluntary!”

“No – No, no more, please, I’ll be good, no more chastity. I learned my lesson.”

She sat down and flicked the switch another notch. The pumping of my cock became stronger, deeper, tighter. The grip, the vibrations, the friction were unbearable. I had spent so many hours of my life doing this, stroking, but I always controlled when to stop.

“Please, may I have my chastity device back on? Please make it stop!”

Knowing she had me under her control, she turned the machine off and then wrapped my clitty in a washcloth that had been soaked in ice water! I shivered and shriveled to the further amusement of all as she secured the bindings again.

“Next time, my love, you will be allowed to cum only when you show me your mouth full of the cum from at least one of my guests. Now off with you – you have that to look forward to!”

 ( ii )

Tiffany had such mixed (mixed-up?) feelings after that session. Sexually, she was so happy to finally have the release of the intense orgasm. She was completely humiliated in the process, and now all their friends saw what position Tiffany now had in the relationship – a subservient doormat, existing for the amusement and pleasure of the dominant wife. Actually, Tiffany was okay with that aspect of it. True, she had shown herself in a public setting cross-dressed to the max and had performed like a trained monkey to the hilarity of the whole group. But it also allowed her to focus on her need to cum in a way that she never had before. It wasn’t just a “toss-off” like one of far-too-many in the past, but it was special and unique.

Then her mind wandered to the final promise – next time she would have to show a mouthful of cum before she would be granted release. Now THAT was something completely different. Humiliation, crossdressing, pain, all that was just one side of it. But not every sissy dreams of sucking a cock. And Tiffany was not sure how she really felt about that, herself (lol Miss). She had never had a cock in her mouth, or even in her hands.

Locked in chastity, dressed like a gurl, the weeks went on with no release. Tiffany spent much of her spare time (when not cleaning, cooking and doing the household chores) trying to imagine what it would be like to have a cock in her mouth. BC (Before Chastity), she had enjoyed lying on her back, with her legs pulled over her head and her cock pointed right at her mouth. Then she’d jerk off until she bathed her face with her own cum. Sometimes, she’d open her mouth wide and spurt right into the opening, coating her tongue with her sticky fluid. She’d pull a pretty painted finger across her face and wipe the splattered cum off and suck her finger clean.

But that was her OWN cum, and she could never quite fit her own cock in her own mouth – God knows she tried! (lol again.. Miss) To have another man’s cum in her mouth, well, that’s different.

Her cock stirred in her tight chastity device at the thoughts and her frustration grew daily. Finally, the day arrived when a big house party was going to take place. The moment of truth was drawing near.

On the fateful night, She went about her maid service duties as well as she could, with some level of distraction and anticipation. People ate and drank and paid her little attention. Then an announcement was made that the entertainment was to begin. She was led to the middle of the room, and a blindfold was secured putting her into darkness. She could feel the warmth of a large male body approach and stand near her.

“Do you know what your task is here, tonight, Tiffany?”

“Yes, Miss.”

“Tell everyone.”

“I must show you a mouthful of cum in order to be allowed my own Release.”

“Is that what you want?”

“Yes, Miss, please, I do.”

“Tell me what you want.”

“I want to cum.”

Without warning, Miss gave Tiffany a swift kick in the balls. The chastity device did not protect them at all; if anything, it made them tighter, fuller and protrude. Tiffany doubled over and almost fell to her knees.

“Stand up, bitch! Have you learned nothing? Are you still thinking just about your own pathetic orgasm? Think carefully, and tell me again what you want.”

“Tiffany grimaced in pain and tried to stand tall. “I w-want to show you a mouthful of cum.”

“NO! – This kick was harsher and sharper and aimed with more intent to inflict suffering. Tiffany fell to the ground.

“Pull the bitch back up onto her feet.”

“I will give you one more chance to get it right, Slut. Now what do you want?”

Tiffany hesitated, knowing she had better be right. Then it dawned on her.

“I want to suck cock, Miss.”

The crowd cheered, laughed and applauded.

“Yes, Miss Tiffany cocksucker, that’s what you truly long for isn’t it?”

“Yes, Miss, said Tiffany, understanding washing over her. “I’m a cocksucker. I want to suck a cock.”

With that declaration, Tiffany was gently pushed to her knees.

“Reach out in front of you.”

She felt a man’s legs.

“Open his zipper and take out his cock.”

Tiffany obeyed.

“Take off your blindfold and look at it.”

Tiffany was mesmerized by the sight of this thick, long beautiful cock in her hand.

“Do you want it?”

“Yes, Miss.”

“What do you want more than anything in the world?”

“I want to suck this cock, Miss.”

“You will when the time is right. For now, just stroke it gently. Cup the balls, give everything a little squeeze.”

Tiffany followed the instructions as if in a dream. The cock stirred and grew in her touch.

“Now we will see if you are ready. I have decided that you will not be cumming today because you did not show me that you had learned your lesson. The lesson was to Know Yourself. Now the question is – knowing you will be remaining in chastity either way, you will not be cumming – do you still want to suck the cock?” 

Tiffany immediately knew the answer. She had forgotten about her own pent-up desire for orgasm. All she wanted was to have this beast between her lips, to deepthroat it, to lick it, to suck it. To bring pleasure to this cock until it could hold back no longer, and to receive the full jet of cum into her mouth, happily, greedily. To be fulfilled as a cocksucker.

“Yes, Miss, please may I suck this cock?”

“Yes, you may Tiffany. You have graduated and now there’s no going back.”

She took it in her mouth. She could hear the click-click of all the phones as the cameras got going. There was no going back.

“Don’t close your eyes, slut. Look up into the eyes of the man whose cock you are sucking. It’s time you got to know my lover!”

Tiffany lifted her gaze and saw the man smile down at her. He put both hands on the back of Tiffany’s head, holding it there, then starting pumping with force. Slowly at first, then with steadily increasing rhythm.

“Relax your throat, slut, or you’ll choke on it,” he instructed.

Without removing his cock from her mouth, he slowly backed up until he could sit on the couch, pulling Tiffany along with him.

“I’m going to have a seat because I just came in your wife’s pussy, so I may not be coming again for awhile. You just keep going, Tiff”

Tiffany had given up all thoughts other than this cock, so she didn’t mind. She threw herself totally into the thrill of what was happening. As she stroked and sucked, she could feel her little maid’s dress being pulled up high. Then she felt two hands on her buttocks, pulling them apart. Then she heard a zipper.