Toys are more fun

"Such a pretty little thing deserves a present," you saying, flashing him a dazzling smile.

You have him kneel on the floor to unwrap the little box you had purchased and wrapped for him a few days earlier. He opens the box to reveal a seven-inch clear purple dildo. You see him struggle very hard to avoid showing any reaction--your hand on his chest gives the game away--you can feel the hard pounding of his heart.

"Go ahead, see what it feels like."

You watch raptly as he very gingerly lets his tongue touch it and then allows it a fraction of an inch into his mouth. Patience, you tell yourself.

You make sure that the new toy goes home with him, and ask for photos of him sucking it every day. Whenever he takes it deeper, you give him extravagant compliments.

"Such a good little slut..."

"Look at how beautiful you look with cock in your mouth..."

"There's my good little girly-boy."

In a few weeks he has ordered himself a flesh-colored suction-cup dildo and is practicing face-fucking his wall.

Several times you drop a hit that there are other uses for such a toy, but he just isn't getting the hint. You suppose you could **** it, but a more, elegant, approach occurs to you.

One night you dress him/her up in a skin-tight bandage dress, complete with heels, makeup and tights. You lead her to the mirror and twirl her around to give the full effect. While doing so, you "accidentally" caress her nicely shaped bottom, your hand traveling down and lingering on her inner thigh.

The effect is immediate, and the growing erection is unmistakable through the tight fabric.

"Oh, my dear, that's not very girly, it is?"

She blushes and says nothing.

"Would like like me to help you avoid this sort of accident in the future?"

She nods.

"As it happens, I actually had ordered just the thing a few days ago."

Another wrapped box. Inside, a small, pink chastity cage.

"Can I help you work on getting your girly feelings to take over?"

While getting the package, you had taken the precaution of slipping into a loose silk robe--with nothing on underneath. As you move around her, her eyes follow the creamy slices of skin, the flashes of boob, the bare inner thigh. What chance does a girly-boy have?

She flinches as she hears the lock click shut--you take the opportunity for a deep kiss.

"Now that we are both girls, we can have a lot more fun together."

As you guessed, the effects of being locked changes her perspective on her toys. Soon, she is avidly riding on her floor mounted dildo, cage bouncing beautifully on her nude body. With little other sexual outlet, she becomes an obedient pussy-eater, willing to serve you for what seems like ages if you will toy with her even a bit at the end.

All of which raises the question: is it time for the real thing? You have plenty of friends who would be happy to break in a new sissy. But what to offer first? Her mouth? Or her virginity?