Bryan was nervous and excited when Saturday came. His mom had arranged another date for him. While yes, he had been able to date without his mom arranging things he was grateful for the help. His mom assured him this time he had never met the lady. It was someone Maureen worked with, and Maureen thought this lady, Raven would appreciate and be open to Bryan.
Bryan dressed up and went to Sullivan's Restaurant. He didn't know what Raven looked like, but his mom had made a reservation and they would meet by being seated together at the restaurant. Bryan arrived first and was seated and waited at the table. His mom suggested flowers, so Bryan had bought a bouquet he was holding.
And then suddenly there was a lady being seated at the table. Bryan leapt up to introduce himself and gave the lady the flowers.
He did all this and then took time to look at Raven. She did not look like anyone he would have normally pursued.
Normally Bryan didn't go for bigger girls and Raven must be around 360 lbs. She also appeared to be a little older. Raven had greying hair and would be his mom's age or older.
But she was here, and Bryan knew the polite thing would be to stick with the date and just plan on not doing any return dates.
They had a nice meal together. They found many different things to talk about. Bryan could also see how Raven got her size as she had most of the appetizer they shared, she ordered a very large meal which she devoured, she had two desserts and some of Bryan's food as well.
They agreed to go watch a movie together
The cinema was in the same plaza, so they walked together to the movie. Raven wanted popcorn so Bryan bought a large popcorn and some drinks. The popcorn was gone 15 minutes into the movie. After a bit more of the movie Raven rested her hand on Bryan and then started rubbing her hand on him. She said she wouldn't mind if Bryan wanted to rub his hands on her.
Still not overly into her, Bryan thought it best to just do it anyway. He rubbed her back for a while and her leg. Raven opened her legs for his hand to go in and Bryan rubbed the inside of her legs. Raven was moving her hand on top of Bryans chastity cage. Bryan tried to move away.
Raven whispered "Don't worry Bryan. Your mom told me about your chastity cage to help with your wanking problem. I am willing to work with things for the right guy and so far, I am liking you."
Raven leaned in and kissed Bryan. Then she came in again. Despite the initial unattractiveness it felt good to have a woman kissing him, so Bryan opened his mouth, and they tongue kissed for the rest of the movie as they rubbed each other's legs and bodies.
As they left the theater Raven said she was having fun and suggested they rent a hotel room to spend some more time getting to know each other. He didn't say what he was thinking out loud but Bryan thought it would be best to just go along and have a nice time with Raven and just not look to do any more dates together.
Sullivan's Restaurant was joined to a hotel, so they walked back and while Bryan arranged a room for them, Raven ordered some desserts and drinks to be delivered to their room.
They sat together on the couch when they got to their room. Bryan tried to talk but Raven wanted to do more kissing. They stopped when their cheesecake sundaes arrived. Bryan wasn't as hungry so Raven thought it would be cute for him to feed her. Once the sundaes were done Raven thought the jacuzzi tub looked fun. Bryan set it up with bubbles while Raven went and disrobed. She came back wearing a towel and asked Bryan to make sure the door was locked. She had slipped into the tub and invited Bryan to come join her. As Bryan undressed, he tried to hide the chastity device.
"Oh, let me see it sweety. Isn't it cute? Your mom told me you weren't too big down there and I can tell by the cage. There is lots of ways a couple can have fun, and I hear you have been working on getting better at that."
Feeling a little embarrassed about things, Bryan went into the water. He thought they might just relax together but Raven had other ideas. She had him wash her back for her. Then she laid back for him to wash her feet and legs. Then she had him come and wash her chest. She even leaned forward and had Bryan wash her ass for her. Now Raven said they should go lay around on the bed. She asked Bryan to help her get out of the tub by pushing from behind.
Once she got out, she picked up a towel and wrapped it around. "Haven't let you see my Honey pot yet but if you keep being so good then maybe I will, you drain the tube while I go get set in the bed and then you come on in."