I told Frank about Mary and her tongue fucking my ass. Even though I made it clear that it was very fucking hot, he also made it clear that he was not into eating ass. Okay, I guess for now. I was curious about his night.
Frank seemed to be holding back about his evening with Robin. After considerable assurances, he finally relaxed and told me how much he enjoyed it. He told me that they fucked for a while, then they moved to a sixty-nine. I mentioned that I had checked on him and Robin and had seen them getting into it. He seemed surprised, but after realizing he would have done the same for me, he was alright with it. He said she had kept deepthroating him, holding his cock in her throat while he came, which won Frank over.
I don't mind swallowing Frank's cum only because I love him. It would be nice if he could get over his aversion to kissing afterward. I'm not a big fan of swallowing, but I will admit that in the past, I have given more than a few guys a blowjob (or two). I may have even had a bad reputation in high school, but that is a different story for another time.
We had another date night that included Robin, though this time we met up earlier in the day. Once again, we all had a great time and decided to go to dinner that evening. During our conversation, Robin asked Frank if he liked anal sex. He told her he did like anal, but that I was not really into it. She said she really wasn't either but then got a very sheepish grin on her face. Robin told Frank that he could take her in the ass if he agreed to let her dress him up like a woman. He immediately shot down the idea, but I gave Robin a private wink, indicating we could discuss it later.
Later, Frank excused himself to go to the restroom, which gave the three of us ample time to discuss Robin's suggestion. Personally, the thought of Frank dressed as a girl was fucking hot to me, as it was to Robin and even Mary. I told them I would somehow make it happen.
Over the next few days, Frank and I were very busy with our respective jobs. While we enjoyed sex almost every night, we were just too tired. Then Friday arrived, and we had more free time to relax and enjoy ourselves. We went clubbing and danced for hours. Once we got back home, we started kissing and making out pretty intensely. It was time to make my move.
I chose this moment to bring up Robin's idea. Again, Frank was not agreeable, but I assured him it was just him and me and that it would be fun. I was surprised when he agreed. Before Frank could change his mind, I began working on him. I kept encouraging him and complimenting him so that he was at ease.
Frank likes to think of himself as a GQ kind of guy. The problem is that, as I mentioned before, his slender looks are somewhat androgynous. He is always clean-shaven and doesn't need to shave every day. He does not like having short hair and keeps his hair in a classic quiff, which I sometimes tease him about. Still, it is sexy on him.