He does

The game goes down to the last point. Unfortunately, her side messes up and they lose. As the 2 teams congratulate each other, Emily talks to her worthy opponent, finding out his name is Jeremiah

He asks what day dinner will be. Emily says she isn’t sure, so he says he is free Monday night. When she agrees, he reminds her of the dress of the day, which she acknowledges.

Emily realizes she likes that she lost the bet. She hasn’t had the attention of a guy for months, and misses it. She continues taking her pills, and her stress level has never been lower.

Emily’s work on Monday goes quick, and she is home by 8:30 PM. Jeremiah was expected at 9:00 PM, so she starts the food. They agreed on burgers, so she gets them started.

As the burgers cooked, she changes into the outfit. Standing in her room naked, she decides that she would wear the cutoffs she made. She slid on her thong, then pulled on the cutoffs. She can’t believe she is gonna wear these for dinner. She pulls out her new bikini top, then decides to go for the slut look. She grabs her old bikini top that she wore with the cutoffs. The only difference is when she ties the top and back strings, there isn’t much left over and it isn’t a full coverage fit anymore. A lot of skin is showing around the edges.

Jeremiah shows up promptly at 9:00 PM, dressed as casual as Emily with board shorts and a tank top. Emily has no doubt he likes what he sees as he sits at the table. The burgers were cooked, so Emily brought them over. They both ate with some talking going on.

After dinner, Jeremiah has a seat on the couch and Emily turns to him, as she sits down at the other end of the couch, her legs pulled under her. She finds he is only a few years younger than her and is a theatre major. This makes her wonder as he says it, but he continues that he just finished a production his friend had produced for the internet.

She asks if it can be seen by anyone, which he tells her no. So he asks if her laptop is mirrored to her TV, which it is, so he finds it on the dark web and starts playing it. He jumps forward halfway through, and stops at a point where he and a girl are at a table, with her giving him a blowjob. Emily notices the girl is struggling and looks to be gagging. Jeremiah can tell Emily is excited by this, as her nipples were tenting her top very visibly.

He then jumps to another scene where the girl is now lying on her back on a coffee table getting pounded. It is obvious they are both cumming together, then Emily gasps as she sees Jeremiah slide his cock out of her. Not only was he not wearing a condom, but he kept pulling out of her until his 8.5” cock was dangling in a sexy way.

Emily just stared at Jeremiah as he stopped the vid, and notices a bulge in his shorts. She has been drawn in and asked if that scene was done in one take. He laughs and says that scene took forever, as they had to redo it a total of 8 times over a month long period. Emily asks why, and he explains they did the scene 3 times in 2 days, then the girl said she had to go to the college Health Services. Emily looked at him wide eyed and he just nodded. He said they did another 3 two weeks later, then the final 2 another two weeks later.

Emily tells herself she could never do that, but she is intrigued. She kisses him and asks if she can see it. He tells her to pull it out if she wants. She can’t resist, and pulls his shorts down and it snaps out fully hard as his shorts clear. She is holding it 2 handed and slowly moving her hands down it. Her eyes are focused on the cock, and he asked if she wants to give it a suck.

Against her best judgement, she nods and slides her mouth over it. She knows she can’t deepthroat it like that girl did, but she does a admirable job sucking it. After a few minutes, he sees it is getting messy and tells Emily she needs to take off her top. Without stopping, she nods and he takes that as an affirmative.

He reaches down and unties both knots and throws her bikini top on the couch. She continues without any help from him for about 15 minutes, which impressed both of them until he says he is about to cum. Emily has to make a decision.