Cuckold in Milwaukee and the Wedding - Sex Stories

Cuckold in Milwaukee and the Wedding

My wife and I were attending a wedding in Chicago the night before Thanksgiving. She was thinking that on the way home we could stop and see one of her “friends”. I thought that could be a fun night. The entire night she was overly horny and kept rubbing her hand along my crotch and saying she couldn’t wait until later. About 11pm she said it was time for us to go. We made our goodnights and headed to the car. No sooner were we on the expressway than she had her heels up on the dash and she started to rub her pussy. I noticed she wasn’t wearing any pantiees. She grabbed my hand and placed it on her wet mound and said, “see how badly I need to get it, I’m soaking wet”. She was soaking wet. She took out her cell phone and dialed her friend. She said, “we are on our way and I am soaking wet. The dickless wonder and I will be there soon. Did you do any shopping for the dickless one?” She must have gotten an answer she liked because she just patted my cock. As we drove she kept playing with herself. It looked like she wasn’t bringing herself to climax but she was having fun. As we were going down the expressway there were several tuckers that tried to keep pace with us so they could watch her. As we got to her friend Jim’s place, she looked at me and said, “Jim is dressing as Jeanne tonight so don’t freak out.” I knew he was a cross dresser and was looking forward to it. We got to Jeanne’s place and she couldn’t wait to get out of the car. We went to the door and were greeted by ...

... a magnificent looking 60 year old women. It took me about two minutes but I realized it was Jim/Jeanne. She invited us in and I saw she was wearing 4 inch spiked heels, garters, very tight panties and a baby doll nighty showing off perky little breasts. Judy couldn’t wait t go at it and was kissing her before I even came through the door. It was an amazing sight watching two ladies kiss like that. Jim stopped her and held out a bag from a lingerie store. Judy thanked her and looked in it and handed it to mw and said go in the bedroom and get dressed. I went in the bedroom and found some thigh high stockings, 4 inch heels, a bra and panties for a bbw. I started putting them on not having any idea what was going to happen. Before I got very far Jeanne came in and said she was supposed to help, that Judy wanted by body hair gone and my eye brows plucked. Jeanne showed me how to shave my legs and the rest of my body hair. I put on the clothes and she helped me with some simple makeup. The entire time she was helping I couldn’t not look at her tits. I said, “Looks like you have something new.” He laughed and said Judy asked him too so he had been taking hormones and using creams. We came out and Judy jumped up and down and started taking pictures of me. She and Jeanne took me by the hand and had me sit down on the couch and they secured my ankles and hands so I couldn’t do anything. They turned on the tv which showed the bedroom. Judy gave me a peck on the cheek and said enjoy. ...