19 Year-Old's First Time Leads to Misunderstanding

Thanks so much to Dylan for sending me this awesome clip and the full story to share! I can't tell you how much I appreciate this kind of thing from viewers.

Dylan and Amanda have been dating for about 6 months, but his friend Paul actually met her first. That has led to more than one joking comment of "I saw her first" and Amanda thinks it’s funny. On a few occasions Dylan has mentioned to Amanda that he actually wouldn’t mind watching her have sex with Paul. She is not really the adventurous type in bed, however, so he didn’t have much hope for anything like that. The farthest he had gotten was to get her to watch some cuckold clips online with him a couple times, but they seemed to repulse her a little.

After some rare morning sex in his room on her 19th birthday, Amanda unexpectedly asked if he still wanted her to sleep with Paul. When he said he did, she told him that was good because she decided to give him a present even though it was her birthday and already arranged for Paul to come over later to "do" her. Dylan couldn’t believe his luck!

There was one catch in that she didn’t feel comfortable having sex with anyone watching, so Dylan would have to leave but she would record it for him. By early afternoon Dylan was so excited he could barely stand it. Amanda even tried to give him oral to relieve some tension and make sure the camera was recording properly. But just then Paul arrived and Dylan was hurried out the door. The irony that his friend was going to use his own bed to have sex with his girlfriend crossed his mind as he was driving away and it actually seemed to make it more exciting.

Even though Amanda and Paul were gone, he was so excited to find the video camera and a love note when he got back an hour later he couldn’t wait to watch it and hit play. But what he saw wasn’t exactly what he expected. First, he is concerned because he notices Paul doesn’t use a condom, which he didn’t think even needed to be said. Further, he’s kind of put off by how nasty and rough Paul is treating his girlfriend. And the kind of things Amanda was saying was a real shock and way out of character. By the time he hears her tell Paul not to pull out of her early his stomach flips. What was she thinking? Even though she is on birth control it was still very upsetting and a risk! And the comments about doing her the way he always does and something about darker halves is very confusing. Did he miss something here? This is their first time, right?

Regaining his composure by the time he spoke to Amanda a little later he had a good laugh when he figured out what had happened. Amanda’s only experience with this kind of thing came from the online clips they watched together. And just by chance those clips had similar kind of scenes. As far as she knew, Dylan wanted her to pretend to be slut and for Paul to be some kind of stud spreading his seed. No wonder she had been repused by the thought of cuckolding. She had actually needed to talk Paul into doing and saying those kind of things! And he even felt so bad that he apologized to her once the camera was off.

At that point Dylan knew two things: he had the best girlfriend in the world to do all that for him. And he needs to talk her into doing it again in a more natural way.

Originally posted to the Do My White Girl Blog September 10th, 2011.