I began pleasing the man who responded to my craigslist ad a lot. Almost became a regular thing, heading to his place every few days to help him with his load, and he would do new stuff every time. There was even times where I just went over because I was horny. We were always practicing throat fucking, deepthroating, and rough handjobs. But every time I went over, it finished with his load in my mouth. Sometimes even more than one. But it was the same old thing every time.
I eventually delete my craigslist ad, I only got 3 responses to it, 1 of which flaked out. The other was just a fun 1 time experience. But then I started craving a new cock to pleasure, I mean believe me, hanging out under his desk while he works and I give him an amazing blowjob was fun, but it just slowly stopped satisfying me as much, and maybe him too. I began noticing that my time there during each session was getting longer and longer, but we always started right away. I liked to refer to myself as his fuck toy, or boytoy.
After a few weeks of this, I grew tiresome of his only penis, I wanted more. I posted another ad, as a sissy. Before long I got quite a few responses, maybe it was because I put that I had a little experience, but browsing through emails sent from guys looking to get there dick sucked, many didn't fit what I wanted. Many said they wanted a "rim job", although I had never tried it, I wasn't really planning on it anytime in the near future, then a few days later I got a response from a women, asking how much experience I had. I gave her a quick reply but only told her this was for guys looking for oral, not women.
Now don't get me wrong, I do like women features, but intercourse with them just doesn't turn me on at all anymore. It was to my surprise when she replied asking if I was in need of a mistress. Now, in the picture that was attached it showed a girl with a nice figure, probably around 20-24, wearing a TIGHT latex outfit with a dildo in her hand, no face. I could only reply saying I didn't have a mistress, and asked if she was looking for a sissy.
After exchanging a few emails, she asked me to meet her at her house, as a first meeting, should would take it easy on me but she was in charge. It was almost like she was trying to establish dominance over me already, and I wasn't sure I exactly wanted to do this.
After a few days of planning I went over to her house late one night. I drove up, parked on the sidewalk, and went up to the door and pressed the doorbell. It was only a few seconds before the door opened, and in the doorway stood a women with a beautiful face, same curvish figure, but this time was wearing normal clothes, just tight pants, and a tight shirt.
She looked at me, sort of evaluated me. She stepped aside and told me "Come in, sit down. I'll be right back." She closed the door behind me and ran up the stairs. I looked around and slowly realized that this was a nice little house. Mainly hardwood floor, soft white couches I chose to sit on and wait for her return.
Upon returning she walked down the stairs and around the corner and looked at me as her eyes got wide. She was now in the latex outfit that she had taken the previous picture in and shined off the lights like the hardwood floors. She slightly raised her voice at me "I said sit, not on the couch, you are a sissy, assume position!" I quickly leaped up off the couch and looked around, I wasn't sure what she exactly meant.
"Sit on the floor, on your knees. Quick, now!" she yelled at me. And I did as she commanded, dropped to my knees hands resting on the floor in front of me and looked at her. "That's better." she said looking at me. "Now it's time we got started." She walked over to a desk next to me with a pink laptop on it, opened one of the drawers of it, and pulled out a tanish dildo, unlike the pink one she had in the picture.
She walked over to me, shifted her weight to one side placing her hands on her hips and looked me, dildo in hand. She extended her arm so the small dildo was inches from my face, "Suck it whore." I looked at her for a second, then realized that it was a command, I leaned forward, used my lips to wrap around the head, and began forcing the whole 5 or so inches in my mouth, all the way up to the handle where her hand was placed.
I worked up and down the dildo, looking her in the eye as I did. She smiled slightly but wiped it away before she thought I could realize. She began pushing on it, as I sucked on it she would force it in as much as possible, I could see the suction cup just past her hand as she forced it over and made me suck a small portion of the handle.
The work of this just felt different, I couldn't taste any of the salty goodness, one of my favorite parts about being a sissy. It was almost like I was doing this by myself again, which wasn't quite as good. After a few minutes of sucking, she yanked the dildo out of my mouth. "Good job slut." she said to me as she looked at me with those blue eyes. "You do have experience, how about you come back here daily and we can get a little work done."
Again, I knew this was not a question, and she was not expecting an answer other than yes. "I have another man I please every few days..." I said slowly and dragging on, not sure how she would respond to this. "I don't care, you are my bitch now. You can call me Missy and bring along this 'friend' so we can have double the fun."
"I usually go to his house to -", she cut me off by saying "I don't care, you're mine now. Do I need to introduce punishment so soon?" I tried to finish my sentence, "I am not sure..." Again she cut my sentence short with a raised voice commanding me "Lay back, now!" I did as I was told, not sure what she was going to do. She stood over me and it was now that I realized her outfit didn't have any covering any of her butt or vagina. She was shaved, cleanly, ready for whatever she was about to do next. She turned around and dropped down so that her lips aligned directly with my mouth. "Lick it, now." she ordered.
I slowly stuck my tongue out and touched the bottom of her pussy, I was forced to breathe through my nose but all that I could smell was her freshly cleaned butthole. It only took a few licks before she dropped completely on me, forcing me to sufficate through the smell of her anus as I licked her pussy and was smothered by her ass cheeks. She was doing a little bouncing, trying to force my tongue further inside of her, I wasn't enjoying this as much as she did and almost lost all of my arousal. But again, I believed this was called punishment for a reason, so that I didn't enjoy it like she did.
I was nearly out of breathe by the time she lifted up on one leg and placed the handle of the dildo in my mouth as she aligned her wet pussy with the dildo and began riding my mouth while her ass smacked into my face time after time. It seemed like the smell of her asshole still lingered but was now mixing with sweat, she was getting pretty worked up. Before long she began shaking, with waves of orgasm and thrusted the dildo in as far as she could while her ass cheeks once again smother me and I was forced to take the fresh smell of her anus in.
She sat there, for a few seconds, attempting to recover while still smothering me, I began running low on air and almost started struggling before she got up and turned around just to sit back down on my chest. She took the base of the dildo in her hands, examining her juices that now soaked it with a mix of my saliva. Then looked at me and held it to my mouth, I opened my mouth slightly and she forced it in again forcing me to taste the juices she made.
She got up, and looked at me while I laid there with her dildo covered in her juices rested in my mouth. She rubbed her finger through her lips and brought it to her mouth and took a small lick. "Good, aren't they?" She asked me while I looked at her. "You can take it out now." she said as she stepped back. I pulled the dildo out of my mouth, "Not what the kind of pleasure I enjoy..." I said to her slowly as I began to stand up but remembered her snapping at me earlier, so I dropped to my knees again.
"Perhaps next time, don't disobey me." she said with a smirk, watching me drop to my knees realizing that I had been broken by her. "You didn't put too much enthusiasm into sucking a dildo as I thought you would." She said looking at the dildo on the floor next to me. "I prefer the real thing." I said looking at her staring at her work.
"How about tomorrow you bring your friend, and we can have a little more fun?" She said to me. I knew by now not to give her a reason not too, so I just nodded. "And all you do is oral? Why not extend to anal and playing?" She said looking at my ass rested against the ground. "I'm not ready there. " I replied. "Afraid? How about we fix that tomorrow too? It's easy, and a lot of fun." she said.
"Alright, I guess I should get going. I'll try to contact him tonight." I said as I sat there, afraid to rise to my feet of what she might do for not obeying her authority over me. "Good sissy. Feel free to leave. I look forward to tomorrow." she said as she ordered me up and forced me to do the door. As I left, I heard a click behind me of the door locking, walked down her driveway and got in my car before I pulled out my phone and emailed my first fuck buddy.
Dedicated to Missy. :)
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