Chloe had already thought carefully about how she would approach the matter. She didn't want to tell Greg herself that he had a small, inadequate penis. He should determine this for himself. Once in bed, she kissed Greg and then looked him in the eyes.
"You know, I knew right away that you were a sub. But don't worry, that's not bad at all, I like it." She wanted to get these two messages across very directly.
Greg was briefly shocked by her directness, but it was also clear to him that she had noticed this in the meantime.
"How and when did you notice?" he asked still.
"Already on our first date, when I jokingly said that I cannot wait to make out with you, you got all nervous and blushy. And come on, you love to lick me, you love to follow orders, you just love to please me! 'Submissive' is written on your forehead and even a blind person could feel it. You know what the other guys usually want? My previous guys were not submissive at all, many alpha males approach me. They just want to get into my panties and fuck me with their cocks to get off, that's it. They would never care about my fun. So, I like your attitude, really." Chloe made sure to refer to others' 'cocks'.
Greg realized the wording but who was he to argue about this now. "You're right, you probably have a good eye for it."
"What about your ex-girlfriends, didn't they notice?"
"No, none of them ever brought it up. Maybe they just didn't want to." Greg could only explain it that way, as he had not changed any of his behavior.
"Hard to believe actually and such a shame too, there's quite a lot of your submissive talent that hasn't been used, just yet."
Chloe now grinned seductively again.
"Show me how you had sex with your ex-girlfriends. I want to see that. What position did you usually do, all boring missionary?"
"Yes, exactly."
"Let me see then," Chloe took off her top and panties.
Greg grabbed a condom from the nightstand, nervously fiddled to get it on and positioned himself over Chloe. His little man had already gotten hard again, and he directed it to Chloe's awaiting pussy. Fortunately, Chloe was still wet from their conversation. He grabbed a pillow and slid it under Chloe's butt. It was always easier to penetrate that way. At that moment he wondered if all men did it that way or just him because of his lack of length.
Chloe was wet as always and now that she was paying attention to it, it really wasn't a very intense feeling when he entered her effortlessly. She did feel him thrusting in and out as he now took a slow rhythm, but the feeling was faint. He penetrated her like this for several minutes.
"Ok, so this is how you used to do it? This is how you got them off?" Chloe grinned at him with a mixture of pity and sarcasm. She looked at the ceiling giving her best to look bored and exhaled with a sigh.
"Yeah," Greg was embarrassed that his effort seemed to have little effect on Chloe. He didn't feel strongly about it himself, either. The friction was minimal.
"Did they come in the process," Chloe asked innocently again.
"Yes, I think so," Greg blushed a dark shade of red because he knew that it wasn't true. But he didn't want to tell Chloe that, in fact, all his relationships had ultimately boiled down to exclusively oral pleasure for his partners.
"I see," Chloe said with a knowing smile.
