I quite liked that Olivia gagged when my cock hit the back of her throat, but I figured it was time for her to learn to deep throat properly.
I’d bought everything I needed so it was time to put my plan into action. I lay her face down on the floor and ran some rope from her shoulders to the ankles cuffs. I pulled the rope tight, forcing her body to arch until she was rocking back and forth on her stomach.
Her wrists were, as usual, cuffed behind her and I ran another rope from her wrist cuffs to a ring on the head harness and pulled that tight as well. This pulled her hands up painfully and her head back.
My training tool was a fucking machine that I’d just taken delivery of. This device is simple: a motor drives a wheel; attached to the wheel is an articulated arm with a dildo on the end. As the wheel turns, it moves the arms back and forward, fucking the person on the other end. The speed of the motor can be controlled and by adjusting where on the wheel the arm attached, you can adjust the length of the stroke as well.
I attached an eight inch dildo and positioned the head of it just past her teeth. I turned the machine on at its lowest setting and its shortest stroke and it pushed the dildo forward two inches and returned it to its original position. I let this cycle continue for several strokes before turned it off and adjusting the position of the arm. This time the stroke was long enough to just hit the back of her mouth without triggering a gag reflex. She let out a little moan every time it reached its full depth.
I sped it up a little and left running for five minutes. She was drooling a little, which was supplied enough lubrication, so I adjusted the arm to the next position.
This time it did trigger her gag reflex. She made a lot of noise and thick strands of drool ran down her chin. I’d placed a bowl under her in case (really, when) she vomited. I sped it up again until it was thrusting every second. After a few minutes her gagging slowed down; she was finally figuring out how to swallow it. After about fifteen minutes she hadn’t gagged for several minutes so I adjusted the arm again. The machine drove the dildo the full eight inches into her mouth and throat.
This time she vomited, the contents of her stomach forced themselves past the dildo and into the bowl. Ten seconds later, the dildo reached it maximum and she vomited again. This continued until she had nothing left in her stomach and was dry retching. Thick strands if saliva and vomit covered her chin, but the machine kept going regardless. Eventually the retching slowed down and stopped and I turned off the machine. Her stomach muscles were spasming and cramping from the number of times she’d vomited. I put a ten inch dildo on and started the machine again. Initially she’d gagged a little but managed to accept it quickly. Unfortunately, I didn’t have a longer dildo to try, but I’d have to correct that. I slowed the machine right down until it was taking a minute to complete a stroke. With the dildo in her throat she couldn’t breath and her face was turning red. When the dildo had pulled back far enough, she breathed rapidly and deeply before the next stroke. Her training was coming along well, and it was time to test it for real. I moved the machine out of the way, knelt down and put my cock in her mouth. At six in inches long she easily handled it and her lips reached the base of my cock without her gagging. I came in her mouth and let her have a break for an hour, before using the ten inch dildo on her again for thirty minutes. This continued all day: machine on for thirty minutes, then off for an hour.
I’d continue tomorrow after getting both longer and thicker dildos. For the time being, I positioned her pussy on the dildo and let the machine fuck her at its top speed of three strokes a second. She came multiple times, even without my help.