Frank sat in a chair a few feet away from Grace just watching and waiting to see if she needed any assistance. So far she was enjoying the challenge she had given herself, and Frank was not needed.

She started in a sitting position on the bed, eyes closed and completely naked. She did not mind that Frank was watching. And actually, since it was Frank, the exhibitionist in her liked his watching. She purred softly as she rubbed her clit with fingers from her right hand and occasionally played with her nipples with fingers from her left hand. She had been trying to fist her pussy for a month, working at it a little each day. She had tried various techniques, most of which ended up hurting, but she kept trying. The biggest mistake she had made was rushing it, so today, she was taking her time, getting herself warmed up.

She knew that lubrication was one key to success, so she worked on getting herself flowing with natural lubrication. Actually, she had accomplished this small goal fifteen minutes earlier, but she was enjoying herself too much to move on to the next stage.

But now, she let her middle finger from her right hand slip inside her pussy, exploring the wetness and warmth. She slowly pulled it out, pressing against the wall of the opening. Once out, she rubbed her clit, purring softly again. Then she slowly penetrated her cunt again with the finger ... and then back out ... and then rubbing her clit ... and back in...

She did this for a few more minutes, before pressing two fingers inside. Her middle and index finger moved in side by side slowly ... and then out. As before she rubbed her clit in a clockwise motion with her thumb. She moved her two fingers in, making sure they were as close together as she could get them, pushing them in as deep as she could. This time, as she pulled them out of her pussy, she spread them apart so that they would stretch the muscles at the opening to her vagina.

After a few minutes, she added her ring finger to the penetration. Three fingers, as tightly bundled as she could get them, going in, ... and three fingers, spread apart – stretching her pussy, coming out. Although she pulled her fingers out all the way, she stopped rubbing her clit between each cycle for fear that she would cum before she had her entire hand inside. She now used her palm to press against her clit during penetration, not as effective as her fingers – which was part of the reason, but it still felt good.

After a few in and outs with three fingers, and her palm rubbed slightly against her clit, she realized she was not getting her fingers in as far. So she forsake her clit all together, moved her right hand down more, and forced her three fingers in as far as they could go.

After a few more minutes, she added her pinky. Four fingers in, tightly together and deep ... and four fingers out, spread apart. Her breathing got shallower as she finger-fucked her pussy. Without being completely aware, she started rubbing her clit with her thumb again. She was so in the moment, just enjoying masturbating herself, and barely aware of Frank's presence in the room.

She slowly returned to her awareness of what she was trying to accomplish and resisted her strong urge to rub herself to orgasm. But she still took her time, knowing that she was approaching the point at which it usually hurt, forcing her to stop. "Not this time," she told herself.

After a few more minutes, she was able to get all four fingers inside, past her knuckles on those fingers. Now, she moved her thumb from her clit to in line with her other fingers. She had stretched the muscles enough, so that the five fingers entered without any problems. They slid right in up to the first joint, and then she pulled them out. And back in to the first joint and then back out. She did this for a few minutes.

She narrowed her hand, which pulled her thumb back so its tip was at the second joint of her other fingers, and pushed her fingers in. Easily to the first joint, ... and back out, ... and back in to the second joint – and the tip of her thumb, ... and back out, ... and back in, ... and back out, ... and back in. She held it there and wiggle her fingers some – it felt strange. She pushed in farther up to the knuckles of her first four fingers, ... and then a little bit farther, ... almost past the next hurdle ... almost ... a little more time ... a small push ... and the knuckles of her four fingers were in, along with most of her thumb.