Anal

"I'll take any anal cherry from a pretty woman. Are sure? You did struggle earlier on with me stretching your pussy".

Leon stroked her back and hips, he clearly wanted to but was making sure I was really sure about it.

"Yes, tonight is special but it could be more special for you and me tonight, I'm ready". She said softy.

She mouthed "I love you" to her son. Which made him jump or scare him off, he stayed and continued to jerking off.

She took her eyes off of him and slightly giggled, from the excitement of what was about to happen. She moved to reposition herself. She eased grabbed a pillow to place under her and then slid downwards, arching her back as much as possible making sure to rest her chest flat of the bed and pushing her ass up as high in the air as possible. And making sure to keep her head forward looking at the window.

Her son was closer to the window now the light from the room making him less of a shadow now. He stayed on his knees and even thou she couldn't see him masturbating; she could see his arms working up and down. He must have a decent sized cock, for it to be a two hand job.

Just like with her pussy her anus put up a fight, not wanting to be strecthed out by the thickest and longest black cock she has ever taken. For a moment it was shock when his tip touched her anus, it was painful when the head got in. Making her yelp. They stay put until the pain stopped and he contiuned slowly pushing all his length and girth in. she was socked, each time he annouced.

"Aw, shit that's another inch you white slut".

She had a mini orgasm when he bottomed out, he rested enjoying the feeling of his whole rubbered cock rested up her ass. She understood what was happing he was pleased to have conquered her ass, and she was pleased herself for taking it. Any large black man would love to fuck her but to fuck her big ass, was a dream none had experienced with her. Her ass was one of the main assets every black man loved about her.

Now he started to slowly pull back and forth in her ass. Fucking her from behind like a dog with her own son beating off his dick. What a moment, if only Leon knew he was conquering her ass and her son's mind. Her face twisted as Leon with his new confidence keep pumping hard into her opening ass. Her own son not too far from the bed, watching his mother take it from this black man he didn't know.

"I'm Cumming."

She felt spasm after spasm from his huge fat black cock. She had an orgasm after 5 minutes of fucking her ass plus she found it exciting watching her son look in. Leon worked his cock in and out of her ass still. The wickedness of what was happing to her made her have another earth shaking orgasm this one was so intense that she never heard Leon yelling.

Leon pumped his black seed into the condom covering his cock. Leon pushed deep into her ass and held her hips tight as he stayed put, she felt the condom filling up inside her ass. It was a blissful moment. Once there orgasms stopped Leon stood up and stayed walking towards her bathroom, he pulled his condom off and tied it up threw it away in the same bin that Devon had done the previous night.

"I had no idea that you would be so hot in bed." He said walking off.

She just smiled and layed on her bed feeling very empty in both her holes now. She couldn't stand up her legs were shaking too much still. She put a shaking hand on her face, covering her shameful smile of been fucked in her ass for the first time whilst her son watched. The toilet flushed and Leon appeared he walked over to her and moved her hands from her face and kissed her.

"I have to go back home, my wife needs me to drop her off to work early and I need to drop my son off to school after that, so I have to go now".

He slowly got dressed clearly conflicted about going for round 2, he grabbed all his stuff asked her to call him tomorrow at work he might be able to get them working closely on a project at work. And with that he left quietly. She pulled herself out of bed and picked her robe up off the floor walked over to the window. There was no one there James he was gone.

She quickly dressed in some sports sweats and walked down the hallway towards James's room. It was almost midnight now when she opened his door and looked inside, he was in his bed and looked up when she entered.

"Hun, I'm sorry, I've got to run down to the **** store really quick. I'll be home as fast as I can." She said in a half whisper.

He nodded and she gently closed the door and made her way out of the house. She locked the door and headed towards her bedroom walking down the side of the house being as quiet as possible. She looked in and from her vantage point she could see Son. He walked into her bathroom and stood with his back to her, she could tell that he was jacking off because of how his arm was working. She looked in the mirror on the far way and could see that Son had slipped Leon's used condom onto his mouth and was sucking hard.

But what really surprised her was that he was wearing a Chasity cage, a metal one and a small one at that. It had to be very tiny, his dick was either small or was average and squeezed tight. He looked like he was having trouble using one hand to sort of pump himself. At first she didn't know what she should do. She watched as her son jacked off his tiny caged dick whilst he sucked a used condom. He kept moving his hand faster and faster.

After awhile he started to rub the tip of his dick that was throbbing and trying to escape the cage. She was mesmerized, she had never seen this before. She wasn't into this type of thing she knew it existed but never felt the need to look it up. As made a guess that his dick was tiny after all why would you do this if it wasn't. She continued to look and started to compare the body of her black lovers to her son, it was no comparison. She watched and found herself getting that now familiar feeling in between her legs as she watched her son trying to get off in her own bedroom. She reached down and slipped her hand into her sweats. Gently pressing her small fingers into her used pussy. It was sore to the touch after the fucking Leon had just given her. She couldn't help herself and she started to rub ever so softly while watching her son jack off.

It must have felt really good to James because she could hear him moaning as he masturbated. Then without warning James did something she knew that he might. He started gulping clearly the rubber had broke and he was drinking the Leon's thick plenty load. He pulled the rubber out of his mouth. He then started twitching and he released a small load of cum as he continued to rub his dick tip, very clear and small cum fell out of his cock cage. Onto my floor his body was trembling with a lot of effort to release not much cum. It must of felt great but looking at him and the load, I laughed, compared to what black men could produce it was pathetic.

James raised the condom to his face and let a few drops of cum fall onto his face. Just when she thought he was done to her surprise he started to lick all over the outside and inside of the condom. She knew that he was licking up her pussy juices too. This sent a shiver down her spine and she was not prepared for the orgasm that ripped through her. Her son was not just after the contents of the condom. He was licking and smelling his mother's pussy juices.

She looked at the lust that was on her sons face and knew that he had been where she was now. Kneeling and looking into her bedroom window. She knew that he was jacking off as a result of what she had let him see. The poor kid had seen her in bed with two different black men in two days. At his age he was full of sexual tension and after what he had seen this is how he had found to express it. She also knew that she had to help him get back to a normal sex drive, but how?

She left him to do what he needed or wanted to do. She later returned home resolved to find a solution to help her son. She just had no idea how she was going to do it. In the morning she got up and made them both breakfast, she left for work after given him a goodbye kiss like she always did. This time it was different, she knew that he had tasted her pussy juices and Leon's and Devon's cum plus had seen her having sex.

She came across a very interesting internet post looking for answers. "How Make Your Son A Sissy For A Better Healthier Future"

It had many articles about this new trend for white boys who were becoming sissies. The main article focused on one couple's son who had gone all the way. The mom said "He had always been a little feminine", and rather than wait for life to guide him or lead him astray, they acted and went to look to see if they could help him. They took their son's sexuality into their own hands to ensure his happiness.

This included many and long family sessions, one on one open therapy, promoting and rewarding a feminine lifestyle, they started this when he was 14 years old and they could tell how quickly and positively he was reacting in 3 months. Seeing where this was heading. they went to professionals to make this a permanent thing. He is now 20 years old and officially a sissy now. He was the very first white sissy starting off this new trend.

How about I make my son a sissy before he goes off to college?