Free Erotic Stories

The sissification of Bob

The Sissification of Bob

Bob & Sharon were a second marriage mid 50's couple who had been in the lifestyle for several years. Bob had swinging experience in earlier relationships but Sharon didn't.  Early in the dating period his suggestions were met with interest and enthusiasm.

Bob was a fit athletic type who went from running to cycling competitively. Barely a day went by without him working out. Sharon was a 5'1" blonde haired, blue eyed beauty with 36 D breasts that always got a lot of attention.

Early on they went to swing clubs and parties. Though Bob played some what he was much more interested in Sharon being pleasured. She realized early on that she loved a womens touch and got crazy wet when men played with her. Sometimes Bob would just sit back and watch her play and play and play.

As they learned more and more about the lifestyle they realized they had evolved into a Hotwife-Cuckold couple, Sharon basically called the shots on where they went and who they played with. She liked the power behind being a Hotwife and enjoyed telling him. "Just sit over there and watch"

She learned about her role as a Hotwife and started questioning Bob about being bi sexual. Bob had never had any experiences with guys and didnt want any.  Sharon was quick to tell him, "When it comes to our sex life I tell you what to do . Do you understand?" Bob replied "yes"

Sharon started what she called the sissification of Bob very slowly. Bob loved her long slow hand jobs and she started with a lubed finger in his ass. In the beginning he complained but she told him if he wanted a nice long hand job there had to be something in his pussy. When he started getting used to the anal play his orgasms were better and better and he started looking forward to the training.

Sharon advanced to a butt plug and a small vibrator. She made him realize he had to learn to use his ass as a pussy, For now on his ass was only to be referred to as a pussy. He was starting to really enjoy the daily play when she started inserting a dildo into his mouth and started to teach him how to suck a cock. "You suck like you are using a straw" she would teach him.

One nite she told him that they were going to take a ride to a place nearby where they had heard men go to play. They went to a place called Nitecaps and they both went into the booths to see what would happen.

She realized that most guys were there for men and she actually was cock blocking him, She realized that they were gonna come back but she would have to wait in the car.

A week or so later they went back. Bob was given instructions to get a cock in his mouth for the first time. Bob went in and was very nervous. He went into a booth , put a movie on and took out his 7 1/2" cock. Within a few moments a guy came in and got on his knees. Bob remembered he was there to suck cock and not sit there and be serviced. But it was too late as he dropped a major load into this guys sexy mouth.

When Bob told Sharon what happened she wasn't happy as he had failed to meet the objective.

They tried again a week later with the same result. When men saw his hard and very large cock there was no opportunity to suck only to sit and be serviced.

Sharon in conversation with another Hotwife explained the problem. The other HW suggested she put on a cock cage so he could not be serviced.

She decided to put it on him for the 24 hours before there visit to Nitecaps. She told him "I have the key so you know what you need to do." He went in and walked around, not just sitting in  a booth like before. He noticed other guys sitting and watching with their cocks out. Waiting to get serviced. He started chatting with a 45 year old good looking guy. The guy reached down and felt the cage and asked him why was he wearing it. He explained what his wife wanted . The guy  (Doug) took him by the hand into a booth and locked it. He sat Bob down and took out a large hard cock and said "Suck it" Its the only way you will learn. Bob was nervous and tried doing what Sharon had taught him. Every time he came up for air Doug would push him back down on the cock saying "don't stop sucking until you get what you came here for" After about 10 minutes he emptied into Bob's mouth. He remembered what he was taught and sucked and cleaned Doug off. Doug told him what a great job he did. Bob loved the compliment  but felt like a dirty boy.

When he went outside he told Sharon what had happened. She was very happy and when they got home unlocked his cage to realize a very horny boy and she inserted his butt plug and started stroking him. But now we was so horny that he asked her to fuck his pussy with that dildo. She realized that nite that he was ready for a strap on. Little by little he was becoming the sissy she wanted, She bought the strap on as a surprise gift to give to him when he deserved it.

Bob's training developed to the point where if he wanted to be pleasured by his wife he would let her know he has his cage on. When 24 Hours passed he would go to Nitecaps and perform and rush home to tell Sharon what he had done and be unlocked. She stroked him slowly and when he begged for the plug she told him she had a surprise and put on the strap on. He wanted to be taken from the back but she wanted him to take it like a girl and had him lay on his back. She demanded he keep his eyes open and look into her face and he was being transformed into a sissy.

Bob often wanted to make love to his wife. She told him after he was transformed she would let him, with the approval of her FWB. As a Hotwife he knew she would go out a few days a week but didnt realize she now had a steady boyfriend .

He grew to love the strap on and was now being caged most of the week only to be taken out after returning from his weekly visit to Nitecaps.

She knew it was time to continue his training when she insisted he shave his mustache and goatee and let his hair grow, He was afraid of what was coming next.

About a month later she told him that they would be attending a Fri nite party for cross dressers in NJ. Bob didnt have a problem with it until she laid out a complete outfit for him on the bed. A womens outfit.

She started dressing him around 7PM after he completely shaved. She put thigh Hi's on his muscular legs and a short skirt and white shirt. The makeup was the hard part but by the time she was done he was really cute with decent length red hair.

She herself was shaved and dressed very sexy for the nites activities.

When they arrived at the closed private bar they paid the fee and walked in. Bob was extremely nervous. Especially wearing the high heels she ordered on -line for him. There was many cross dressers and he was surprised to see how good he looked compared to the others. They had conversation with several folks and one in particular invited them to an adjoining motel room party, When they got there Sharon was the only women with a half dozen c -dressers. They were anxious to meet and explore the new member.

Finally the partys organizer Sandy said it was time to initiate Bob, Sharon was like, "lets do it" and allowed Bob to be blind folded and placed on the bed. The group took turns placing their cocks in his mouth before someone removed his girly panties and said "lets see his pussy" . They gathered around and Sandy said "Im first". Sandy took his pussy for the first time. Bob taking it for the first time and had no problem after Sharon's training. They all had a go at him and also enjoyed what Sharon had to offer.

After a wild few hours the party was breaking up and they told Bob to be at the next party in 4 weeks. Bob assured then SHE would be there!

THE END