Don's Feminization Pt. 01

Don remembered the first night he met Lisa and wondered how he had gotten to this point. There was no going back from here. She had him trapped and what was about to happen would forever change his life.

Don and Lisa had met while out with some friends one night about three months ago. She was attractive and sexy but not a knock out. He was really attracted to her and she seemed to feel the same. He had been divorced a few years and dated some but nothing seemed to stick. He was polite and a total gentlemen and he thought a pretty good lover. He was very concerned with making his partners cum. He thought that the only thing getting in the way of a longer relationship was one fetish he had.

He really liked wearing panties and the girlier the better. He had been wearing them since he was a teenager when he tried on his older sisters panties. She was twenty and home from college for Christmas. The laundry room was also an extra half bathroom with a full length mirror. Don was emptying the dryer, so he could put his clothes in and a couple of Michelles panties were in it. He was alone in the house and before he knew it found himself stepping into a pair of pink half back cotton panties. They had a tiny bit of lace around the waist and a small bow on the front. When he had finished pulling them on his member was semi hard and he felt so sexy as he looked into the mirror. From that day forward he wore panties almost everyday. He wasn't gay and wasn't into guys but just loved the way panties felt.

Every time he would tell one of his girl friends they would suddenly decided he was not for them.

Lisa was different she didn't mind at all! In fact she seemed to really like it. After a few weeks of dating Lisa really started to make more decisions on what they should do for dates and in bed. Don was fine with that even though he thought things were moving pretty quickly. His job required him to make a lot of decisions and he was a control freak so it was nice to have something he could just let happen. Lisa seemed to thrive on this fact and she took advantage of Don's acceptance of her dominance.

Things began to change one night when they were out. They had been out to dinner and were going to catch a movie at the mall when Lisa said, "Hey let's do some shopping we have time."

Don said, "Okay."

Lisa grabbed his hand and he could feel that she knew exactly where she wanted to go. Within minutes they were outside Victoria Secret. Lisa said, "I think you need some new panties."

Don looked at her a little shocked but had always wanted a girlfriend he could go panty shopping with. They went into the store and one of the sales girls greeted them and asked if they needed any help. "Yes we do.", Lisa said, "My boyfriend needs some new panties but I think I can handle picking them out."

The sales girl didn't know what to say and blushed while saying, "Okay you two have fun and let me know if you need anything."

Lisa took her time picking things out for Don but was also conscious of the time because she really wanted to see the movie they had tickets for. They finished up, paid and headed to the theater.

Don and Lisa were both movie buffs and always stayed through the end credits. They felt it was just respectful to all those who made the film they had just watched. The showing was the last of the night and no one was left in the theater when the credits finished except the employees cleaning up. They got up and walked out. Once out of the theater Lisa handed Don the Victoria Secret bag and told him to go put on a new pair of panties.She was very specific about which ones. They were lavender and all lace half back, which was the style Lisa liked most on Don. Don complied with her and changed into them. He realized when he pulled his pants back on that the panties were high cut and came up above his pants. He pulled his shirt down over them and left the mens room.

Once outside Lisa looked at him and said, "Don I chose these panties for a reason. I want anyone who is still in the mall to see them. She rearranged his shirt so the panties were clearly visable.

They walked out of the mall and Don was so happy there was almost no one there. He made it out without anyone seeing his panties but he also felt a little disappointed that no one had seen. He was torn about all this new play with Lisa.

Sex for the next few weeks was fantastic and Lisa told Don she wanted him to have sex with her while he was wearing panties. Then they always had sex with him in his panties. One night after one of Lisa's awesome blow jobs she came up to kiss him and he realized she hadn't swallowed his cum. Her hand was on his balls and she squeezed. He knew what she wanted. He opened his mouth and she let all his cum drizzle into his mouth. It was the first time cum had ever entered his mouth. It was mixed with Lisas saliva and was salty and had a very strange texture. She put her hand on his chin closed his mouth and told him to swallow.

Don liked how his sex life had changed and he liked how much Lisa was in control of him. He felt oddly empowered by loosing control. Each week he tried to guess what would be next. Lisa's touch was becoming more and more forceful and she had started tying his balls up before they would have sex. One night she tied him down to the bed arms over his head and legs spread. She put a rubber band around his sack so his balls were trapped and then she flogged his cock and tied balls. Don was amazed at how excited he was by this. Then she got him hard and began to jerk him off. Lisa told him not to cum and that if he did he would be punished.

She stopped for a minute and took a couple pictures. Then she was back to it. She slowly jerked his cock and told him not to cum. He focused and focused and kept himself from cumming. Then she put the tip of his cock in her mouth and he couldn't hold back he exploded all over. "You stupid sissy I told you not to cum!!" She slapped his cock and balls hard and then picked up some of his cum and rubbed it all over his face.

"I can't believe you came!" She untied him and told him to get on his hands and knees. He did as he was told prompting Lisa to say, "Good boi." Don could hear the inflection in her voice and knew that when she said boi it was meant to have that implication of a sissy.

"Now take your punishment!" She spanked his ass hard at least ten times. "Now you stay there if I come back and you have moved you will get another spanking."

While Lisa was gone Don could feel his ass start to burn after the slaps. They stung as Lisa was spanking him but now he could feel the truth of how hard she had slapped him. He dared not move for fear more slapping would occur. He realized he was dripping with pre-cum. He thought god I just came and now he was leaking again. He couldn't believe how excited he was.

Lisa came back after a couple minutes. "Hold still" she said and he felt her rubbing his asshole. Then he felt something cold and wet, he knew it was lube.

"Oh no Lisa please don't!" Don had never used anything on his ass. He knew her intentions and while he had always thought about what it would be like to have a girlfriend do this to him he never thought it would be in this fashion.

Lisa could hear the fear in his voice. "Shut up slut boi and take your punishment. I have known since a couple days after we met you were a perfect candidate for feminization."

Don felt pressure on his virgin asshole as Lisa pushed. He could feel his ass start to open and then she backed off and added more lube. Then the pressure came again this time she didn't stop and Don moaned as he felt his asshole open up and then the dildo slid deep into him. Lisa held it there for a moment saying, "God I love deflowering sissies."

Lisa began to fuck him slow and deep. Don was moaning a little from the pain but mainly from the pleasure he was feeling. The pleasure he was feeling combined with the intensity of the moment made him want to submit to Lisa completely. Lisa leaned over him and he could feel her gorgeous breasts on his back she began to pull on his nipples. He thought OMG this is exactly how I pinch women's nipples. Lisa whispered in his ear how sexy he was. With that comment he felt his body tense and shudder then his cock began gushing cum. He thought it would never end. Lisa kept fucking him for a couple minutes after he came. When she was done with his ass she pushed him on his back sat on his face and told him to make her cum. Don loved making her cum this way but somehow this was different. He was her servant and he was so happy to please her. Lisa's sex was always so sweet tasting and she was always wet but this time she was extra wet and there was a tang of salt in her juices. After about 5 minutes he felt Lisa begin to tense her legs on his head and he knew she was cumming. Her body was tense for at least 30 seconds and she arched her back, Don looked at her gorgeous body sitting on him and thought, "I love this punishment."

Don was sore the next day when he woke up next to Lisa they kissed sweetly and she rubbed his back and thanked him for such an awesome night. They spent the next 2 hours in bed drinking coffee and talking. Don was surprised at how little they discussed the night before.

The next few weeks Lisa and Don continued to play in the same way. Lisa was very slowly feminizing Don. It was little things mainly. She had him panties 24/7, started him using moisturizer everyday, shaving his legs and trimming his pubic hair into a landing strip above his member which she had started calling his clit. The first time she called his penis a clit he was offended but within a couple days he took it as compliment.

All of those things were pretty easy to handle but one night she told Don it was time for his clit to be totally under her control. She revealed a small pink cock cage. To this Don visibly reeled in slight protest. Lisa was steadfast and told him to stand up. He complied slowly. "Good boi." Lisa said.

She got on her knees in front of him and looking up said, "Believe me this is the last time I will ever be kneeling in front of you."

She placed the ring around his balls, slide the cage onto his clit making sure it was tight on him but not pinching anything. Then she put a small padlock through the front pin and locked it. She told Don to stand still. She walked over to the dresser and picked up a small necklace and showed him. "Here is the key to your lock. Your clit is now caged unless I release it." Then she put it over head and it nestled itself in her cleavage.

They both knew the future held fantastic excitement. Lisa had plans for Don and Don was excited to follow her lead wherever that might go.