I was having a pretty crappy day so a really good friend of mine, Chris, came over to hang out with me. We had a few drinks as we chatted and joked. After a little while, I just blurted out that I broke up with my long-term boyfriend. Chris knew it had to be something serious because we had been together for over a year. When he asked what happened I looked down like I was embarrassed. “He was just too boring,” I finally said. He looked confused. “What do you mean boring? Mike was a pretty fun guy.”
“Well, yeah, he was but not where it mattered with me,” I said. “Oh just forget I said anything. This is too weird to talk to you about.” “Come on Brooke, you know you can tell me anything,” Chris stated, “I’ll make you a deal, you tell me what happened and I’ll, um, tell you something that I’ve never told anyone!” “Okay…” I began, “He wouldn’t try new things with me in bed. I thought for sure that after we were together for a while that he would open up more sexually, but he didn’t. He even told me that I am too kinky for him and that he would never be on my level!” Taken back a little, Chris said, “Wow! I can’t believe he wouldn’t try new things with you. I mean, come on Brooke, you’re gorgeous and fun, what guy wouldn’t want to explore sexually with you?”
Then I started to get a little uncomfortable so I quickly changed the subject. “Okay, enough about him. Spill your secret!”
Of all the things he could have said, “I wear women’s pantyhose and panties,” was not at all what I was expecting! Something stirred inside me and I realized that I was getting turned on just by picturing him in them. “No way, do you have them on now?!” I asked. He looked down as he sheepishly replied, “Yes, I have on pantyhose.” “Don’t look embarrassed! I want to see!!” “I don’t know, Brooke,” he stammered. “Come on Chris, I’m not going to laugh. I’ll show you something too.” I got up and started walking to my bedroom and he followed. I started to think back on our friendship and it dawned on me, that Chris was always the type of guy that went along with anything, never even putting in his opinion.
Maybe he wanted someone to take control. I never thought he could be a sissy panty boy until now that is. We got to the bedroom and I told him to take off his pants and show me. “Now!” I said with authority. Seeing that spark in his eye, I knew that my thinking was right! Hmm, this was going to be fun! He undid his pants and sure enough, underneath them was a pair of purple pantyhose.
My pussy was getting wet just imagining the possibilities.
I reached into my nightstand and pulled out a strap-on. His eyes lit up even more when he saw what was in my hand. “This is why Mike freaked out,” I said. “He took one look at it and told me I was fucking crazy. You don’t think I am crazy, do you, Chris?” I gave him a wicked smile and he knew exactly what I wanted. “No, Mistress, I would LOVE for you to give me a good pegging. I’ll do anything you want me to.” He was almost pleading.
I told him to take his pants all the way off and bend over onto the bed.
“Do you want me to take off my pantyhose Mistress?” “Not a chance, I want those on. You need to feel them on you, reminding you that you are my sissy boy. Now, do you want me to make you my little bitch Chris?” I asked. “Please, Mistress Brooke!” he begged. “Please make me your sissy bitch. You have no idea how bad I have always wanted this!”
I made him get down on his knees in front of me and watch as I inserted my double-sided dildo into my pussy and then attach my strap-on. I looked down at him and told him to suck my fucking cock. “Get it nice and wet so I can fuck that tight little ass of yours.” He let out a small moan as he took my rubber cock into his mouth, licking and sucking every inch of it. “You are such a good little bitch Chris!” I said. Every time he slid his mouth onto my cock I could feel it pressing deeper into my pussy and I knew that fucking his ass was going to feel amazing!!
I told him to lean over the bed and get ready for me.
As he bent over the bed, I moved behind him, grabbed a hold of his pantyhose, and tore a hole right in the center of them. I told him to reach behind himself and spread those fucking ass cheeks apart for me. I took my rubber cock and positioned it at his tight man pussy and started to press into it. “Whose bitch are you Chris?” I asked. “I’m your bitch Brooke. Please, fuck my ass, please mistress!!” he begged. Did I take that sweet little ass as he wanted? Or did I make him beg me even more? Give me a call and find out just how much of a bitch I turned my sissy boy best friend into.
