First I put on my sexy Victoria’s Secret thong. It was white with black lace, and it felt so hot as it slid on. Then, I put on the matching bra. It had a lot of padding, so even though I have a little bit of a chest, it really helped to give me that womanly look.
Then, I slid on the garter belt over the panties. One of my favorite parts was slowly slipping on the silk stockings, feeling them over my smooth legs, and clipping them into the garter belt. It made me feel so girly and slutty.
Next it was time to get some clothes on, so I slipped into my grey blouse, and my little blue checkered skirt. I liked to walk in my heels, so I put on my sexy five inch heels before doing my hair and makeup. I had a nice long brown wig, which I liked to brush and style a bit.
For my makeup, I did a nice smokey eye look, with some dark red lipstick. I had my fingernails and toenails painted from the night before, so they looked nice and sexy. But now what? All dressed up with no place to go!
I went online for a bit to see what kind of fun I could find. There were a handful of people that I liked chatting with, and some that I regularly would get on the phone with for some fun. I ran into one guy who I liked phone fucking, so we got on a call.
He was kind of kinky and liked to get dirty, which I sometimes enjoyed. He told me that he wanted me to do some things that I’d never done before. Maybe some things that I’d find uncomfortable. I was intrigued. He started me out by telling me to take my dog’s collar and put it on, with the leash attached, so I did. Then he had me fill a bowl with water and put it on the floor.
He commanded me to walk around on all fours barking like a dog, and then had me drink out of the bowl. I felt a little uncomfortable, but I did what I was told. Then, he wanted me to oink like a pig, so I did this too. I was getting kind of turned on by being a depraved little bitch. My clitty was hard, and I stroked it as he commanded me. He told me that he wanted me to touch myself but not to cum, but he was upset that I had touched myself without permission. As punishment, he had me walk into the bathroom on all fours, then take a squeeze of toothpaste and rub it on my asshole. It burned, but at the same time, it felt kind of good.
As the sensation wore off, he asked me, “What’s the nastiest thing you’ve ever had inside you?” I told him probably just a dildo, and he said he wanted to change that. He told me to get in the kitchen and describe what was around. He stopped me when I got to “mop.” He had me lube up the mop handle and slowly push it inside my ass. He didn’t want to hurt me, so he told me to make sure not to take it too far. Just enough so I could get some control over it, so I could mop the floor a little bit.
I moved around the floor with the mop in my ass, feeling it push deeper inside. I felt like such a slut. He then asked me if I had a feather duster, which I did. He had me remove the mop and replace it with the duster, so I could do a bit of dusting with the duster in my ass. I was so hard, and I was stroking myself the whole time. I could hear him masturbating too.
He had me go back into the kitchen so he could hear my heels on the floor. That turned him on. I pulled the duster out when he told me to. Then he asked me to go a step further. He wanted me to go downtown to a pay phone and call him from there. I was really nervous about doing such a thing. It was morning, and people would be around.
I decided to go through with it though. Before I left he told me to do two things. Put my dildo in my purse, and take an ice cube and put it in my ass, so I did. I drove downtown and parked my car the whole time feeling that ice cube melting inside me.
As I stepped out I felt so nervous. I made my way to a pay phone, put in some money and dialed his number. He told me that I better still be talking with my girly voice, and that he wanted to hear that I was in public. I let him hear the sounds around me. He told me that I was a good girl, and could get back into my car and call him again from my cell.
He asked if I knew of someplace secluded I could drive to, so I went to a small parking lot, where I knew no one went. I was still nervous about police seeing me and thinking something suspicious was up, but I was too turned on to stop now. He told me to get in the backseat and then get the dildo out. I did. He told me to pretend that we were teenagers on a date, that he was some hot guy trying to get into my pants.
He built up a whole fantasy of me being this sexy girl that the hot jock was trying to fuck. Of course, I didn’t fight too hard, and he had me take the dildo and start fucking myself with it. He instructed me to go nice and slow at first. Long strokes, long slow and deep. It was a thick 8″ and it felt so good sliding in and out of my hole. The sensation of that cock and his commanding voice made me feel so slutty, and vulnerable. I could hear him stroking his cock, and his breathing was getting heavier. He told me to start fucking myself faster, so I started to move the dildo faster and harder.
My clit was rock hard even though I wasn’t touching it. I could feel an orgasm building up. On the other end he started moaning and finally blew his load. He described how he wanted it to be his hot cum shooting into my pussyhole filling me up, and how he would take a tampon and put it in me right after so his cum would stay inside me.
As he kept talking my clit started gushing and pulsing. I couldn’t believe I was cumming without even touching it. It was my first time having an anal orgasm – cumming just from getting my ass fucked by my dildo. It was such a turn on to cum like the woman I knew I was.
I happened to have a tampon on me, so I took some of my own cum, gathered it upon my fingers and put it inside me then put in the tampon. We said goodnight and I drove home with an assful of cum and the satisfaction of knowing that I was one step closer to feeling like a real woman.