tagTranssexuals & CrossdressersCrossdresser Gets His Ch. 03

Crossdresser Gets His Ch. 03

byCourtStJester©

Angela was well on her way down the highway by the time Michael had realized that his wife had bought him a maid’s outfit. It was the next step in her humiliation of him, he thought to himself.

She had pleasured herself at his expense all night then taken him shopping while he was dressed as a woman. Then she made him go down on her in the dressing room and embarrassed him in front of a rather shocked (or amused) sales clerk. Now a maid’s outfit.

Angela was nervous as she drove down the highway. She had never done this before so she picked a store that was far enough from home that no one would recognize her. She had seen this one before and after about 25 minutes driving on the highway she took the exit ramp that lead to a small industrial-type park. At the end of a building was a door with the words “Michelle’s Adult Gifts”. She parked in front, took a deep breath and walked into the store.

Angela had hoped to walk in unnoticed, but the large bell above the door rang and let everyone within five miles know that a customer had entered the store. It was unnecessary since there were what appeared to be two store clerks standing at the counter as she entered. The young one, maybe in her early 20’s, continued with her paperwork. The other, an older woman in her early 40’s with a curvy body, long straight black hair and wearing a leather skirt, looked up and smiled.

“Hi, I’m Michelle. Is there anything I can help you with?” she asked Angela.

“No,” Angela replied, “I think I’ll just look around for a minute.”

And look around she did. The store contained a wide assortment of adult “gifts”.. videos, magazines, costumes, toys. She wandered up one aisle and down another until she found what she was looking for.

“Can I help you pick one out?”

Angela turned with a look of embarrassment on her face and Michelle just smiled.

“I… er… um…what’s the most expensive one that you have?” was all she could get out.

Michelle reached up and pulled a package off the shelf.

“This is the most expensive strap-on harness we carry,” Michelle replied handing the package to Angela. “It’s $89.95 and not a bad one, but…”

Michelle took a couple of steps to her right and took another package off the shelf.

“This one is only $49.95 and is much better. Take a look at the straps. They are wider and more comfortable on this one and they’re adjustable. The more expensive one is not adjustable, the straps are thinner and can cut into you after a while.”

Angela didn’t realize there was so much to consider when buying a strap-on harness. She looked at the less expensive model and handed it back to Michelle.

“Thanks, I’ll take that one,” she said.

“Good choice,” Michelle replied. “Now, do you need a cock?”

Angela giggled which caused Michelle to smile. Angela noticed how pretty Michelle’s face was when she smiled and it made her more comfortable.

“Well, I already have one, but what do you have?” she replied.

“We have a large assortment right down here,” Michelle said as she walked further down the aisle. “Most of them will fit in that harness. Do you know what will best fit in your girlfriend?”

Angela uncomfortably turned to Michelle.

“Well, it’s not for a girl, it’s for my husband,” she replied hesitantly “and I want it large.”

“I see,” replied Michelle and she gave Angela a knowing glance. “How about this one?”

She handed Angela a large rubber cock. It was somewhat pliable, 10 inches long and two and a half inches thick with vein-like bumps running along its sides. She ran her hands along the flesh-colored phallus and smiled. It was perfect.

“I’ll take it,” she said to Michelle. “One question though, how do you put all this together?”

Michelle turned and yelled up to the young lady at the front of the store.

“Judy, we’re going to be in the fitting room for a minute.” She then turned to Angela. “Follow me.”

Meanwhile, Michael had changed into the maid’s outfit. It was a short number complete with black stockings and a garter. He kept his bra on and when he was finished he looked at himself in the mirror. With the exception of the cock tenting the front of his skirt, he looked like a real maid, if real maids wore this kind of outfit.

He got to cleaning the house as he was told but soon he realized that he would have to take care of his raging hard-on so he headed for the VCR in the bedroom. This time, he choose a MMF movie and lay back, stroking his cock. He had most of the work done and figured he could get his rocks off, get changed and be waiting for Angela to get back.

He watched the action on the VCR. Two guys were doing this woman, one in front and one in her ass. He knew how that felt and was happy that part of his punishment was over. The woman was moaning and that really turned him on. He stroked faster and faster until he blew his load straight up in the air and landing back down on his cock and hand. Eventually his stroking slowed and, like most men, he closed his eyes and fell asleep.

Michelle and Angela, meanwhile, had walked to the back of the store, through a door marked “Private” and into a small room with a couch, desk, chairs and a mirror. Michelle locked the door behind them.

“Take your jeans off and I’ll show you what to do,” she said to Angela.

Angela sat on one of the chairs and undid her work boots, kicked them off and then pulled her jeans off.

“OK,” Michelle continued, “take your panties off,”

Angela hesitated but Michelle reassured her. “ I just want to make sure you get it fitted right. No sense in trying to figure out how to do it right when you want to use it, is there?”

That made sense to Angela and she slipped her panties down her legs.

“Good, now slide one leg in here. Good, now the other in here. Good. Now let’s slide the cock into this hole and pull the harness all the way up.”

With a little help, Angela pulled the harness loosely into place. Michelle knelt at Angela’s side and tightened the straps then slipped her fingers between the strap and Angela’s skin and slid them back and forth. Kneeling there, here face a foot away from Angela’s pussy, Michelle picked up the musky scent of Angela’s sex. Still kneeling there, Michelle put her hands on Angela’s hips and turned her towards the mirror.

“Take a look,” she said to Angela who looked at herself in the mirror. With her denim shirt, short hair and hard cock sticking out in front of her, she looked like a man.

“It looks good,” Angela said.

“Yes, it does,” replied Michelle who reached around Angela and stroked the cock. “It looks and feels real and with someone who really knows how to use it, well…”

Her voice trailed off.

She heard in a whisper of a voice by her ear. She took her eyes off the cock in the mirror and looked up to see Michelle standing close behind her, her eyes staring at Angela’s in the mirror. Michelle’s mouth was inches from Angela’s ear.

“Do you want to see how to use it?” she whispered. Her breath sizzled in Angela’s ear causing goose bumps all over her body.

“Yes I would,” she replied.

Michelle walked over to the couch, leading Angela by the hand, and knelt in front of it.

“Kneel behind me,” she said and Angela took her place behind Michelle, who hiked her skirt up around her waist. She reached around and took the rubber cock in her hand and guided it to her pussy. Then she bent at the waist and laid her chest on the couch.


“Push it in,” she whispered to Angela who leaned forward tentatively. Michelle reached behind and grabbing the cock in her hand pulled Angela forward. The mushroom shaped tip of the dildo disappeared between Michelle’s thighs and slid into her pussy.

“Yeah, that’s it,” Michelle groaned as Angela slid the pink monster further into her. “All the way, baby,” she whispered until she felt Angela pressed against her ass checks. “Now start rocking back and forth.”

Angela pulled back allowing about six or seven inches of the dildo to slide out of Michelle before she gently pushed it back in.

“Don’t worry, baby,” Michelle reassured her, “I won’t break.”

Angela picked up her rhythm pulling almost all the way out and then sliding back in fast and hard. She was grasping Michelle’s hips in her hands for leverage, making sure that Michelle was coming back into her as hard as Angela was pushing into her, when Michelle took one of Angela’s hands in hers and started rubbing her pussy.

“Keep going, keep going,” Michelle panted as Angela stimulated her towards orgasm.

Angela could not believe the surreal scene she was in. She had never touched another woman, never mind having lesbian tendencies. She started to rationalize her situation by saying she was the man in this bizarre scene, the one with the cock. But no matter how she cut it, she was a woman fucking another woman.

She was now engulfed in the action, pumping the cock hard into Michelle’s pussy. Her thighs slapped against the back of Michelle’s legs and the sound blended into the background as the two women grunted with each long hard stroke and Angela picked up the pace of fucking and rubbing of the plaything in front of her.

Michelle let out a low, guttural moan and her body shook as she came under Angela’s onslaught. Her pussy clenched at the rubber toy inside it as a warmth rushed over her. She reached behind and grabbed the rubber cock again, this time trying to stop Angela from continuing to ram it into her sore and stretched pussy.

The sudden stop of motion snapped Angela back to reality. Her chest heaved as she gasped for air, feeling as if she had just ran a sprint. She looked down at Michelle whose head was resting on the couch.

“Are you OK?” she asked her.

Michelle looked back, an expression of satisfaction on her face. “Yeah, I’m just great.”

Angela slowly leaned back and let the 10 inches of rubber slide out of Michelle, who winced at its removal.

“Well, I guess you know how to use it,” Michelle said to Angela.

“Yeah,” relied Angela, as she rose and slid out of the harness. “Thanks for the ‘lesson’”.

“No, thank you,” Michelle replied. “I’m just sorry I won’t be able to see you in action with your husband.”

Angela looked at Michelle for a minute, then reached for a pen and pad of paper on the desk.

“Be at this address at this time tonight,” she said as she scribbled on the paper.

Michelle smiled. “Can I bring anything?” she asked.

“Anything you like,” Angela replied. “I’m sure you can find something in the store you might like to bring.”

Angela gathered her things and walked to the front of the store with Michelle. Judy, who had patiently watched the store, gave Angela a knowing smile. She knew Michelle had just got fucked. She never failed.

“I’ll see you tonight?” Angela asked.

Michelle stepped towards Angela and kissed her softly on the cheek.

“I’ll be there.”

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