I felt self-conscience kneeling behind Larry as he laid face down on his bed with my tongue pushed deep into his asshole. Not because I was rimming my wife's brother, but because I'd come straight from work and didn't have an opportunity to get my sissy girly outfit on.
I was discovering how sexually powerful submission could be, especially for a straight man submitting to dominate gay men. Dressing in women's clothes deepened that feeling, but also made it safer for my fragile mind. As long as I was feminized, I could do the dirtiest things and it wasn't my fault. I was under their control. Without feminization, I just felt like a pervert that was choosing to lick man ass.
Despite this, I was still in sub heaven. I spent the first fifteen minutes licking his rosebud and getting him relaxed, then I slowly started pushing deeper and deeper into him with my tongue. I kept worrying that I would taste something repulsive, but I was able to bottom out with my lips locked against his open sphincter and my tongue fully extended. It felt fantastic.
He would twitch his anus and it would contract around my tongue and passion would shoot through my balls like lightning. Half an hour in and he was feeling it too. He rolled over without warning and deprived my mouth of his asshole, only to fill it with his hard cock. He must have really liked my ass licking because my mouth filled with his man cream in just a few minutes.
Larry: UUNNNGGG. For a loser you sure can lick ass. Wait until Roger finds out how much you like to toss salad. He'll be feeding you his backside three time a day.
Me: Thank you Sir. I hope I pleased you. All I want is to serve you and Master Roger.
Larry: Is that all you want? I thought you also wanted my sister to fuck that guy you set her up with?
Like a knife in the chest, I remembered why I had asked Larry for a diversion. I was again reminded that my sweet Sally was going to dinner with a man that both her and I suspected would try to fuck her. And she'd admitted to me that very morning she wanted to fuck him as well. Being a complete sissy doormat had put me in a place where I couldn't really please Sally sexually. Getting Nick to fuck her was my way of ensuring she was still having her needs met, even if I wasn't man enough to meet them.
Larry: While you were sucking my ass, I was texting my sister. I get the feeling she's really getting excited about her date tonight. You are so screwed. If that guy takes her to bed, she might decide she likes playing around. She might never be monogamous again. At least not with you.
Larry was mostly fucking with my head, but his words mimicked my own worries. I have never been a great lover. I have never been a great fuck. It just seems inevitable that once Sally is remined of what she has been missing, she wouldn't want to miss it anymore.
I couldn't think of anything to say, so I put Larry's cock back in my mouth and cleaned it until he was hard enough to fuck my face. The pressure of his dick on my throat pushed all other thoughts out of my head and soon my anxiety melted away.
Larry wasn't up to a second round so soon. After a few minutes of power thrusting his hard cock into my throat he took me into the main room and tied my arms behind my back and tied my ankles together. He sat on the sofa with me draped over his lap and watch television. Every few seconds he would swat my ass with his wooden paddle.
The swats were hard and stung painfully, but they were infrequent enough that I could have laid there getting spanked forever. After each spanking I would thank him, and wait for the next. Before I knew it more than an hour had passed.
Me: Thank you Sir. Please may I have another?
Larry: Look at the time. My sister is going to be getting off work soon, you better hurry home and meet her. Oh right, she's not coming home is she loser? Oh well. I'm done decorating your ass for now. Go get showered and cleaned up for Roger. He'll be home soon.