Mrs. Pennington - Chapter 5

Lately Nancy had been spending every weekend at the house. The two women enjoyed each others company and spent much of their time devising new ways of humiliating Mrs. Pennington’s husband. Henry learned that the two were much closer friends than he had ever suspected. Apparently Sandy and Nancy had met in college where they had shared an apartment together. During that time they had become lovers. Both were bi-sexual, not hard-core lesbians - both still enjoyed a good fuck from a man. They spent most of their nights together sharing the same bed while Henry lay locked up in another room with his little dick throbbing inside it’s metal prison.

It was Friday night and Henry was kneeling, naked except for his belt, at the front door waiting for Nancy to arrive. Henry realized that his dick was throbbing in anticipation of her arrival. After the first few weeks of embarrassment at being humiliated in front of a stranger Henry had become much more comfortable with the arrangement of having too service not one, but two beautiful women. Henry heard Nancy’s key in the door and his dick became painfully aware of it’s confinement, a moment later she walked in closing the door behind her. Henry silently took his expected position behind her and waited for her to lift her skirt. After she did so, Henry obediently placed his face in her butt crack and inserted his tongue into her anus just as he had been trained to do. This was how he was expected to greet his Mistress’s when they entered the house. After a short but respectful tonguing, Nancy simply walked away saying over her shoulder, "good evening Henry."

Later all three gathered in the den for cocktails. It had been a long week for everyone and all looked forward to the weekend ahead. Henry was invited to join his Mistress’s while they sipped champagne, which he served. Henry was even allowed a glass of wine with some of his "special" ice cubes. They all sat and chatted and laughed, Henry being careful to remember "his place", addressing both women as Mam’m or Mistress, but enjoying the conversation none the less.

Sandra brought the subject up. "Henry, Nancy and I have been thinking. We all seem to enjoy our weekends of debauchery together, so much so, that we want to do this on a full time basis. I’ve invited Nancy to move in with us. Further more, there are limitations of what we can do with you while you still have to remain presentable for work every day. Therefore, on Monday morning you are going to submit your resignation. Your new full time job will be to care for the house and Nancy’s and my every need and desire. Is that agreeable to you?"

Henry thought to himself, wow! What an amazing turn of events the last six months have been. First being tricked into slavery by his wife and her girlfriend. Having to become Sandra’s sex toy, then Nancy’s. Now the two of them wanted him to quite his job and begin a full time life of servitude. Was this a dream come true or a nightmare that he’d live to regret? He had to admit to himself that more and more he looked forward to the weekends when all three of them could be together, probably the only thing he desired more were his monthly milkings. What would it be like not to have to go to work every day with all the stress which came with a full time job. Just stay at home and care for the two sexiest women he had ever met. After a short moment of hesitation, Henry got on his knees in front of the two women and sincerely stated, "I would be honored to serve both of you to the best of my ability."

"We’re glad to hear you say that, we were hopping you would," replied Nancy. "In fact, we’re so glad that we’ve decided to give you your monthly treat ahead of schedule. But first we’ve got a few changes in store for you. You see, while we both enjoy having a servant around the house to care for our needs and desires, we both think that having a maid would be better."

"I propose a toast to our new relationship and to our new maid, Sandy said. Henry, excuse me, Heather, pour us more champagne and join us in a toast, place your glass between Nancy’s legs." After a short wait for Heather’s glass to be filled with Nancy’s pee, the three lifted their glass’s and toasted in a new life style.

The transformation of Henry to Heather began with the removal of all of Henry’s body hair. The two women brought Henry to the bathroom where they had an ample supply of hair removal lotion waiting. After being handcuffed, his belt was removed. They applied the lotion to every inch of his body except to his face where they used a safety razor, even removing his eyebrows. Both women remarked how smooth he felt without all his former body hair, Sandy put her hand on his buttocks and whispered, "your butt feels as smooth as a baby’s behind." After a shower, he was brought to the vanity for makeup. Now on their second bottle of champagne the two women were having enormous fun applying makeup to their new maid. "Now don’t be stingy with the makeup," Sandy said. "I want Heather to have a sluttish look." And so they applied foundation, eyebrows, eyeliner, lashes and lipstick to Heather’s face.

Heather was actually a bit short and too slender of frame to use any of his wife’s clothing but he was a perfect match to Nancy’s stature. She had already brought garments for the occasion. After reinstalling the chastity belt, they had to use ice cubes to get Heather’s dick soft enough to be reinserted into the tube, they put a pair of thong panties over it. Then came a black bra with a couple of silicone breast inserts. As Nancy adjusted the silicone filled bra she remarked, "my, these certainly look nice on you, be a good little sissy boy and someday we may buy you a real pair of tits." Next, a pair of thigh high black stockings were rolled up Heather’s now silken smooth legs and attached to a black corset which was cinched unbelievably tight around Heather’s, now much smaller, waist. A pair of black stiletto heeled pumps were then put on his feet and Heather stood wobbling in front of his two Mistress’s.

"The shoes are the perfect touch," Sandy remarked. "But I see he’s going to need a lot of practice walking in them. New rule! You will wear your pumps at all times except when you are sleeping." Poor Henry had only had the shoes on for a few minutes and his feet and calves hurt already, how would he ever be able to wear them all the time? Now with a great deal of fanfare, Nancy brought out a box from the closet. Inside was a French maids uniform. Obviously, this night had been well thought out and planned for in advance. The women helped Heather step into his new dress. Even with the corset squeezing him half to death, he had to suck his breath in even further for the dress to be zipped up. The maids uniform was incredibly tight and hugged his body completely, stopping just two inches above the bottom of his buttocks. Even without bending over he would constantly be showing off his butt.

The final humiliation was brought out from the closet. Sandy placed a shoulder length blonde wig on his head. Both girls made final adjustments to makeup, hair and clothes, then Henry, now Heather, was brought in front of the mirror. All three just stood staring in awe. What they saw was a very attractive, slender blonde with full breasts and a well rounded behind dressed in a very provocative maids uniform. Heather might just as well have had the word "slut" written on her forehead. Sandy and Nancy gave each other a bewildered look that said without words - this has turned out much better than either of us expected. As for Heather, he just stood staring in the mirror, looking back at him was a women he had never seen before. God, she really looks hot! , he thought to himself.

It was a night of celebration and debauchery. Heather was instructed to install the dildo to the front plate of his belt and service both of his Mistress’s with it. Afterwards, it was removed and he sucked it clean in front of them. True to their word, Nancy and Sandy released Heather from his chastity belt. In an unprecedented show of appreciation at how well the transformation had gone they allowed Heather an entire nights freedom, even the handcuffs were left off. Heather was brought in front of the mirror and allowed to whack-off to his hearts content while staring at the sissy slut looking back at him from the mirror.

[ Story continues in Chapter 6 ]
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Page last updated 02-Jun-25 by: Altairboy@aol.com