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Section 1
Preface-Michelle is a former girlfriend of one of Edwin’s close friends. She is 90 pounds and 5’1 with long brown hair and a cute smile.
One afternoon Edwin was hanging out with his friends in downtown Annapolis when Michelle walks in with 3 of her female friends. Since their last meeting wasn’t pleasant he wasn’t sure how she would react to him saying hello so he sent over a round of drinks for her and her friends. She came over and gave him a big hug (longer than normal). She sat down at the table and they consumed a few drinks. After an hour or so Michelle’s friends wanted to leave and head back towards college. Edwin told Michelle that he would be glad to run her back to college but not until tomorrow. Michelle was ok with this plan and walked her friends to their car. When Michelle came back into the bar she gave Edwin a HUGE hug it was longer and more flirty than the 1st one.
She sat down and explained that her friends and her were down because everyone had recently broken up with their boyfriends. She said seeing Edwin made her smile. Michelle went to the bar and got a round of drinks and shots. When Michelle came back to the bar Edwin explained to her what would be the 1st of many “rules”.
Rule #1-No drinking and driving. Rule #2 She does not pay for anything!
While in town Edwin will cover all of her expenses. Edwin & Michelle did a shot of Tuaca and then he introduced Michelle to all of his friends. Michelle did a great job of holding her liquor and interacting with everyone. One person that she took a liking to was Brian. Her and Brian had mutual interests and were talking, laughing. As they moved from bar to bar Michelle and Brian were together flirting, holding hands or standing super close to each other. Later in the night Brian’s wife came over and gave Michelle a deep kiss (Michelle had never kissed a girl like that before) and said “THANK YOU for taking care of my husband! I appreciate it and I am quite sure he is imagining what he can do to that cute little body of yours” “wink wink”. Michelle not really sure what to do hopped up and came over to Edwin and told him what happened. Edwin explained to her that Brian and his wife were swingers, actually everyone in this group are all swingers, and if she dropped her pants and let Brian have his way with her right here in the bar it would probably make Brian and his wife very happy. Edwin then explained to Michelle
Rule #3 You can do whomever you want whenever you want.
If she wanted to be with Brian right then and there it would be just fine no one will get mad or jealous. Michelle then gave Edwin a deep kiss and then she went back to hanging out with Brian. As the night wore on Michelle & Brian would make out and he would have his hand up her shirt or on her butt. Their last stop of the night was John’s sailboat where everyone was paired up, talking quietly and some were making out at around midnight Brian and his wife had to head home. They came over to say their goodbyes. As Michelle & Brian started to make out and say goodbye until tomorrow. Edwin lifted up Michelle’s shirt from the back and unhooked her bra. Brian took this opportunity to caress Michelle’s bare breasts. After a minute or five of touching they parted ways. They all agreed to meet up tomorrow before heading out to watch the sail boat races.
After Brian and his wife left Michelle was kind of sexually charged up. Edwin made 2 drinks and led Michelle to the bow of the boat. Michelle sat on Edwin's lap and they enjoyed their drinks. Their conversation quickly turned sexual. She was playfully mad that Edwin had unhooked her bra. Michelle did not make an effort to re-hook it. Edwin paid her multiple compliments about her breasts and her ass. Seeing how far this will go he asked her to pull down her pants so that he could touch her bare ass. She said ok and lifted up a little and granted him full access to her bare ass. He then revealed
Rule #4-When in Edwin’s house she was not allowed to wear pants.
When she questioned him his response was “An ass this perfect should not be covered EVER” she laughed and said “Ok when I am at your house I will not wear pants so that you can do what you want to my ass”.
At about one am Edwin & Michelle were tipsy and they decided to head back to Edwin’s house. They took a water taxi which was a 20-minute ride. They cuddled up in the back of the boat as she sat down she pulled down her pants to her knees and then placed Edwin’s hands on her. As they got off of the boat Michelle made no effort to pull up her pants. Edwin gave her his jacket and she wrapped it around her waist. They walked the 2 blocks back to his house with his hand on her bare ass. Her pants were down to her knees and she walked a little like a duck but she was enjoying having his hands on her bare ass. Once they got back to Edwin's house she immediately stripped off her pants and she asked about panties and Edwin said yeahhhhh….you won’t need those anymore this weekend. Michelle happily stripped off her clothes and went upstairs. Edwin correctly assuming that he was going to get laid also stripped off his clothes and followed her upstairs. He led her to the big comfy couch and they started making out. He started playing with her arousal. He brought her to climax once and then made her beg before she came again. She wanted to ride him again and he revealed Rules 4 and 5.
Rule 4 is that when she is in Annapolis she is not allowed to wear bra or panties. Rule 5 is that she can be with whomever she wants and when she comes home to Edwin’s place she has to tell Edwin about it.
She happily agreed to both rules. While Edwin was touching her intimately he made her repeat back the rules and she climaxed multiple times. She was spent but still aroused. Edwin led her to the bedroom where he made her beg to be taken. She screamed “Please Fuck Me” He asked her if she wanted a condom and she said no she doesn’t like them, she is on the pill, she is tested and she wants to feel all of him. Before she joined with him he asked if she wanted Brian to do this to her and she screamed YES. He asked if she would like Brian to make love to her and fill her and she screamed YES. He then said well tomorrow you will have your chance and she said YES. Edwin then made love to her until she climaxed twice and he then climaxed within her. They both laid there for a minute as he slowly caressed different parts of her body until they both fell asleep.