Two months later
"I'm not a sissy, I told you I had a fantasy about a corset, not that I wanted to be a sissy." Jeff moaned, scared of what Jen had planned, scared and excited.
"That's why we are going to test you, little pussy licker. Pass the test and we won't do the sissy training. Fail and we start right away." Jen said, a large grin on her face, leading Jeff down the hall to the garage.
They had started down this path several years ago with some bondage and chastity play. Now Jeff, after admitting his ultimate fantasy, was locked permanently in a chastity cage Jen had epoxied closed.
It was mid summer so the garage was warm, and Jeff would be comfortable, well somewhat.
They had a play area set up here, Jeff had built a saint andrew's cross, and a queening chair. Much to his delight, Jeff had spent quite a few hours tied to each of those.
Jen loved the chair, Jeff became her own personal sex toy when he was strapped into it. One of her fantasies was to lock him in it on a Friday night, and leaving him there all weekend, having a weekend to herself, when she was not getting eaten out. She hadn't acted on it yet...but it would happen soon, she promised herself.
Today, though, she had something else in mind.
On her orders Jeff had mounted several pulleys to the exposed beams with ropes that she could use to string him up for punishments. This is where she led him.
Using two ropes she pulled his arms up until Jeff had to stand on his toes.
Going to the cabinet she got out some new toys that arrived this week and Jeff knew nothing about. The first was a massive 10 inch dildo with balls, she ran her hand up and down it, feeling the veins and the girth. About 4 inches from the top was a wide spot. Jen felt a pang of jealousy that Jeff was about to get fucked with this and not her. She felt her pussy getting wetter.
The second item was called a one bar prison. Basically it was an adjustable pole with a large metal base. On top was a mount for the dildo in her other hand. Once inserted into, in this case Jeff's ass, the victim would not be able to get up off it and move, they were trapped.
"Honey wha..." Jeff started to ask.
"Quiet slave, I will explain momentarily." Jen snapped with an assertive power that she lacked early on in their games. She was in charge now and she adored the power.
Setting everything up she inserted about two inches of the dildo in Jeff's ass, with a lot of lube, she didn't want to hurt him. Well not this way. Locking the poll At that height she Stepped back to survey her setup.
"OK slave, here is the test. In a few minutes I'm going to release the ropes a bit. You will have to stay up on your toes to keep that monster out of your ass." she slapped his ass cheeks with a laugh at that point. "You have 60 minutes hanging here. If I come back in and find the balls up tight against your Butt cheeks, you are a sissy. If on the other hand at the end of the 60 minutes you haven't fucked that beast into you, we won't train you as my sissy. Understand?"
Jeff was already breathing small breaths as he shook his head yes.
"No slave," Jen demanded, "I want to hear you say it. Tell me if you get fucked you will be my sissy."
Jeff pulled up on the ropes rising Himself up a little more
"Mistress, if I can't keep this dil..dildo out of my..my..my ass, I will be your sis..sy."
The Dildo was already a bit further in. But it Hadn't passed the widest part yet.
Jen laughed.
"Yes slave, you will be." Jen said. "I've got things to do, call me if you give up and ride that dildo to the balls, like the assman I know you are."
With that she loosened the ropes and left him to his fate.
Jeff strained for what seemed like hours. But it was less than half an hour. Despite his best efforts he slipped down a bit more.
Jen came back out.
"Half an hour down, an half an hour to go and that hungry ass is starting to fuck that dildo." She said with a laugh.
Dragging a chair over she sat down right in front of her slave. Looking him in the eye she seductively lit a cigarette. This had been one of Jeff's confessions of deepest fantasy, to see her smoke cigarettes. She didn't smoke, but she had started to please him. Intending to keep it a sex thing, and not become a real smoker. But she quickly realized she loved smoking. The look in his eyes when she smoked for him was stimulating to say the least. But she was worried, a bit, that with each cigarette she was approaching the point of no return, but deep down she knew she had passed that point.
As she took the first deep inhale, Jeff sucked in a breath as well, and slid down to the widest part of the dildo.
