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.

I let him (actually made him) select which pants and bra set he would wear. He chose a black satin set with pink Hawaiian flowers. I asked why the full-back was not a thong, and he said it was way more comfortable. I filed that away for future use. After placing some tissues in his bra to give him some boobies, I chose for him a cute yellow sundress with tiny bluebonnets on it. I don't own a wig, so I put some mousse in his hair, and after playing with some different styles, I spiked it up. It ended up looking like a cute pixie cut. After several minutes of applying makeup, some eyeliner, and ruby-red lipstick, Frank was truly passable as a girl.

I insisted on taking a photo, even though he resisted. I took about twenty pictures and even a small video before he made me stop. Just for insurance, I uploaded all of them to my cloud account without him knowing. You never know when I might need them. Then he told me it was time to pay the piper. I agreed and asked him what he wanted. He said nothing. He stood, pulled up his dress, and pushed me to my knees. I was thinking about it already. I figured I would give him even more incentive, so I pulled the dress over me so he could watch my head move back and forth under it. He didn't last ten minutes before pumping a rather large load into my mouth.

We took a small break and went to the living room for a couple of drinks. For reinforcement, I kept telling Frank how hot he looked and how turned on I was. He took the hint and knelt between my legs. He wasted no time pulling my pants off and diving into me with his tongue. I could not let this opportunity pass, so to keep the crossdressing vibe a thrill for him, I slid around on the couch to enjoy each other, knowing he loved this position. His enthusiasm was intense, but it skyrocketed when I grabbed his ass and pulled his cock as deep into my throat as it would go.

Success. He came off as if he had been without sex for a month. I laid on top of him and tried to kiss him. Of course, he quickly pulled back (his phobia) and gave me the stink eye. I grabbed both his arms and held them down above his head. We have been together for over two years, but I have never been that aggressive with him. I was surprised at how easily I could keep him pinned down. I gave him a choice: either kiss me or go out on a date dressed as a girl. I doubt you were surprised to find out he agreed to the date.

The next day, I was thrilled to tell Mary that Frank had agreed to the all-girl date night.