Cuckhold in Milwaukee 10
After watching Judy and her transgendered lover and his son have sex for hours they had fun jerking me off and talk about sissifying me.
After I came I figured Judy would get cleaned up and we would head home. She came over and placed my hand on her cum filled pussy and said let’s stay the weekend. I looked at her and she said just think of all the sex we could have.
That was all I needed to hear.
Jim came over by Judy and gave her a big deep kiss and said he was glad we were staying he can plan a lot of things. He said let’s start with getting your hubby some proper clothes. Judy smiled and said ok. They got cleaned up and then got me cleaned up. It was about 10am and Judy said, “come on we need to get you a few things.
” Jim came out and said here are the directions have fun.
Judy drove us and we stopped at an intimate apparel store and she said, “let’s go. ” Didn’t know what she was going to buy but since I get to pay I followed her in. We walked in and Judy asked for Michelle. This hot looking 60 year old came out and asked what she could help with. Judy said (not too quietly), “yes this is my husband and as you can see he has man tits and we really need a bra for him.
” I couldn’t believe she said it to Michelle and the two other clerks could hear as well. Michelle didn’t hesitate and said it’s a common problem but that she could help. She asked Judy weather it was for function, punishment, or sexy. They took me in the back and had me strip to my boxers. I couldn’t believe this was happening.
Michelle was feeling my man tits and finally brought in several different bras and had me try them on.
Judy wasn’t sure so Michelle went to get the other clerks for their opinions. After their help Judy picked several out and then said, “they don’t look good with the boxers. ” Michelle said, “you are so right”. She told me to take them off. I couldn’t believe she said that. I hemmed and hawed and wasn’t moving too fast and Judy looked at me and said, “take off the boxers, I’m sure Michelle has seen many useless dicks.
” Michelle laughed and said, “don’t worry I think all dicks are useless. ” I finally took them off and Michelle laughed and said she hadn’t seen one that small since she saw her brother Jim’s when he was about 5 years old. “
I was sent to another room with about 20 undergarments to try on and told to pick out 5 so I could model for them. When I came back Judy was on a chair and her skirt hiked up and Michelle was linking her pussy.
They were oblivious to the fact that I was there. Judy came a couple of times and Michelle got up and said, “my little brother was right you have a very lickable pussy, I may have to stop over later. ” They finally noticed me there and picked out some panties and thongs for me. Michelle came over and pinched my nipples and tweeked my cock and said “you are lucky to have a wife that puts up with such a pathetic dick”.
She then walked over to Judy and slipped her tongue in Judy’s mouth and her hand up her skirt. They embraced like that for a while and then Judy said, “I think we will let him go back in his sexy bra and panties. I couldn’t believe what I was hearing. Well we walked out of the store with me wearing a black lace nippleless bra and thong panties on a 295 pound guy.
Luckily we only saw two people both women in their 70’s or 80’s one of which turned to Judy and said “you go girl”
The ride back was mostly uneventful and luckily Judy didn’t get pulled over. We got back to Jim’s and I made it back inside without anyone else seeing me. Jim was dressed up and said e should tie him back up, they took me to the couch by the bed and tied me up dressed in my bra and panties.
I saw a camera set up and wondered what was going on and then Judy was getting undressed and laying on the bed. SHe looked at Jim and said let’s go. Jim picked up the video camera and turned it on and pointed it at Judy who was fingering herself and moaning. She looked at the camera and said, “thanks for joining me during my day of fun with others. I need to have fun with others because my husband has such a pathetic dick, which you will see later.
She smiled at me and said, “guess I may be a star. ” The doorbell rang 20 minutes later and the two of them left me tied to the couch. They came back in the bedroom with a large black guy. Judy got on the bed and laid there waiting. Jim said (i’ll man the camera until Steve gets here. ) So he got behind the camera. The big black guy is getting undressed and looked at me and said, “who’s the sissy slut?” Judy said, “the dickless wonder is my husband and he is going to watch me become a movie star.
” With that he took off his boxers and exposed the biggest cock I have ever seen. It was at least 10 inches and the width of a soda can. I’m thinking how the hell is Judy going to handle that.
With that Judy went over and grabbed his cock and started sucking on it, damn but if she didn’t almost get it all the way in her mouth. After going at it for about 10 minutes she laid back and he started guiding his cock into her pussy.
She was begging to get it all in, I couldn’t believe it was going in. Jim was getting the camera up close and personal as Judy was begging for more. I couldn’t believe she was able to take it. They went at it for a while before they switched to doggie style. She took it just as easily that way. He started to pound her harder and grunted he was getting close, she asked him to fill her pussy.
That’s just what he did. Judy came three times during this entire exchange. When they were done Judy came over by the couch climbed up and put her pussy over my face and said, “it’s time for the good little cuck to clean. ” With that her face went over my mouth and I have never seen that much cum. She’s digging her pussy into my mouth as I am trying to clean her and she is cumming so I am getting even messier.
The big black guy thanked her and said he hoped to see her again.
Judy made sure I was getting all of the cum out of her drenched pussy. A few minutes later I heard several voices coming down the hallway. It was Jim’s son, Steve and a group of 4 other people, 3 guys and a girl. Jim said, “you are just in time Judy just took in a Bib Black Cock that was over 10 inches and is hornier than ever.
” She moved back to the bed and the group of 5 went over and started rubbing her and kissing her and licking her. One of the guys laid down and Judy maneuvered over his cock while another of the guys went up her ass and one went down her throat. It was a great site to see as her hand reached out for the other cock as she starts jerking him off. They all started moving more rapidly and you could tell people were going to cum.
In short order everyone but the girl came rather hard. After they came apart the girl started to go down on Judy while someone started in on her doggie style, Judy started sucking off one of the other guys. While they are going at it, Jim’s son takes a camera and gives a friend of his another one, as Jim comes over and talks to me. He leaned in close as he starts to rub my cock and said, “you know she really enjoys this, this is about the 10th time we have had a party like this and she decided to put it on film and invite you, hope you are enjoying!!” I just nodded my head.