Housekeepers Hell - Sex Stories

Housekeepers Hell

... Barbara was trying to be gentle, but that almost made it worse. Alice craved and dreaded stimulation, walking the sharp edge of an orgasm barely holding on.

Ms. Barbara’s gloved hand gently spread her pussy lips, exposing her rock hard clit and allowing her wetness to flow. Alice’s moans became frantic, so Ms. Barbara paused, holding her pussy open but not adding any more stimulation until she could adjust. When Alice had stopped shaking, she scooped up some nectar, carefully coating the plug in Alice’s personal lubricant.

Mommy was taking pictures of Alice’s naughty little pussy while Ms. Barbara worked; Alice knew that the pictures were important to monitor progress, and tried to hold still while Mommy worked, even though Ms. Barbara’s fingers and the plug were threatening to push her over the edge. Finally, Ms. Barbara was satisfied with the lubrication of the plug, and was ready to move on.

“Now it’s time for the insertion,” she said matter of factly. Lisa, please come to the side of the bed to observe. You will need to hold Alice’s hand for this, as it may be uncomfortable for her.

Alice felt Mommy undo the restraint around her wrist, bringing her hand down toward her waist so that mommy could still watch the procedure while holding Alice's hand. Alice laced her fingers through mommy’s starting to feel tense about the procedure. “Alice, you need to relax please,” Ms. Barbara said firmly. “I am going to insert this plug into your bum. It is going to feel ...

... tight, and it might be a bit uncomfortable. I will go slow- I don’t want to hurt you, but I need to measure you before we start stretching to teach you to relax.”

Alice squeezed Mommy’s hand, and moaned uselessly in consent. She felt the wet plug press on her tight hole, not entering, but just creating pressure. Ms. Barbara’s skilled hands knew to build up to the insertion gradually, so as not to hurt or tear her patient’s anus.

She teased the plug on her hole, pressing gently to build pressure. Alice began to moan more regularly; she craved the attention on her pussy, but the stimulation on her most forbidden hole made her tingle. The pressure made her tense and tighten, so each time Ms. Barbara pressed the plug she encouraged Alice to relax. “Okay sweetie I am going to put pressure on it again- dont tense this time...practice relaxing even when I press...that’s it, much better- good girl. Now I am going to start insertions- you need to focus on relaxing, like you just did.”

When Dr. Green was satisfied with the initial stimulation and Alice's associated ability to relax around the pressure, she pressed her index finger to the tiny ring. “Okay sweetie, relax,” she said, gently applying pressure until her finger broke through the seal. Alice gasped, squeezing mommy’s hand at the intrusion. “Just relax like Dr. Green said, baby,” mommy said, “you can do it. Relax your bum around her finger, that’s it.” With both mommy and Ms. Barbara coaching her, Alice was able to breathe ...