How I became a sissy

So it all started from answering a random craigslist posting that didn't even have a picture. I was off work and horny so I was cruising the ads and I came across a Cross dressing married dom and his wife looking for a sub. I was no stranger to the lifestyle and it intrigued me so I began to write an email. We exchanged back and forth for several weeks and then began talking on the phone. The day had come and they invited me over. I was nervous. I am a married guy. My wife knows all about my past experiences but had no knowledge of this relationship. I got my things together and put them in a bag. I had a black corset my leather skirt silky thong panties some black thigh highs and a pair of PVC knee high boots with 5 inch heels. I pulled up and parked out front. I went up and knocked on the door and She answered. It was Mistress Veronica. I would describe her as slender in her late 40s. She had told me never to look her in the face but I stole glances from time to time. She had a stern look and always wore bright red lipstick. Often wore a leather hat with her leather corset. She wore skirts with sexy lingerie thigh highs boots the works. She led me into the bedroom and had me begin sucking her cross dressed husband. His cock is very large and thick. It makes me hard just thinking about how it feels pressed into the back of my throat. He kept me between his stocking clad legs as he pistoned his hips up and down being kind of aggressive with his thrusts and hands. I was a little overwhelmed and gagged. My stomach was completely empty as I had not eaten for like 16 hours previous to our meeting. He didn't seem to pay any mind and kept my mouth working his cock as he leaned forward groping and tugging at my clothes. While this is going on Mistress Veronica was walking back and forth behind me occasionally reaching out to probe my asshole with a gloved lubed finger. She was very verbal telling me how I am going to become their faggot cock sucking slave and I was to do everything they told me to do. After several minutes of this he asked if he could fuck me. She said yes and he pulled out of my mouth and slid off the side of the bed. He began giving me instructions and told me to slide back towards the edge of the bed on my knees head down. I felt his strong hands grab my hips and pull me back towards him. He began sliding his cock up and down my lubed crack pushing up into my leather skirt with his thick meaty cock. he let go of my hip and grabbed his cock and started pressing against my hole. The pain was unbelievable. I had never had a bigger cock trying to cram its way into my hole. He grabbed my hips as I tried to squirm and get away. Mistress was getting very excited and she was nearly shouting instructions. I pressed my head down into the bed and clenched my teeth as he pushed all the way inside me. He was all the way in and I was stretched out flat on the bed being held down by his weight. He began to grind his pelvis into my bottom as he placed a hand on the back of my head. He began to thrust in and out. He demanded me back to my knees. I complied as I pushed my ass back and tried to relax my hole as he began to pound my hole. He stopped for a moment to open the lube bottle and squirt it on his condom and then began pumping me more. His hands were reaching around rubbing my cock through my panties he had my skirt around my waist and he grabbed my hips and began to really go, I felt like he was close and began to talk dirty to him. I told him how much I wanted him to cum and how much I liked being treated like a slut. He let out a groan and buried himself as deep as he could go. He grabbed my shoulders and pulled me up against him and grabbed my throat as he came. He was breathing heavy in my ear as he pulled out from my ass. He let go and I collapsed forward onto the bed. He pulled his condom off and tossed it against my face as he walked out of the room saying "she is all yours". Mistress had me sit on the bed with my hands folded in my lap and my legs crossed feet on the floor looking down. She strolled over to the dresser where a strap on was laying and picked it up. She asked me if I felt I could handle such a large cock. She started to put it on and it was magical to watch her slide the leather harness up over her stocking legs nestling it against her silky panties. Her cock was now hanging between her legs poking out from underneath her skirt. She moved towards me and grabbed the back of my head as I grabbed her big rubber cock and guided it towards my lips. She began thrusting with her hips and pushing deeper inside me. She gave me just a second to recover as I gagged as the plastic pushed against the back of my throat. She kept telling me how good of a cocksucker I was and how much she liked fucking my mouth with her cock. I was drooling all over my leather skirt. I grabbed the cock with my hand and i began pumping it with one hand as I went to go grab the balls with my other hand I rested my knuckles against the inside of her legs. I could feel she was very warm and moist as she had me sucking her big rubber cock. She caught on to what I was doing and stopped and pulled away. She scolded me for it and told me to turn around and get on my knees at the edge of the bed. She said that I needed to masturbate myself as fast as I could and cum in my hand as she fucked me. She told me that after I came she was not going to stop fucking me until after I ate every drop. She said are you ready? I said yes mistress and I put my head down. She reached under my skirt and pulled my panties down around my knees and pushed my skirt up over my ass. She pressed the head of her rubber dick against my tender hole and began pushing inside. I filled up fast. She told me to grab my dick and start jacking. She grabbed my hips and buried her rubber cock in my ass all the way to the ring. I started pumping my cock and it wasn't 15 seconds before I could have came. I was having the time of my life. I held back for maybe 45 more strokes of that strap on in my ass and busted the hugest load into my waiting palm as she stroked in and out of my hole. She demanded that I eat it. I lifted it towards my mouth and took a big slurp. It tasted so good! I began to lick my fingers in ecstasy as my ass was just being pounded. She paused and asked if I was done. She said that she wasn't and continued to fuck my ass for at least a full three more minutes. I sat weird for a week after that. She told me to go get cleaned up and to get dressed. When I got to the bathroom there was a paper grocery bag with the word Sheila written on it in Sharpie marker. She told me to put my clothes in there because they were staying there. I put my clothes on and walked out the door. I was to call every Monday from then on out. Mistress Veronica did all the communication. She was quick on the phone only to set things up and done. I was in a routine from then on out. This went on for about ten months, I called one Monday and Mistress instructed me to never call again. She was divorcing #1 and was moving about two hours away. I couldn't believe it. I didn't know what to do. I had no way of getting in touch with #1 so I formulated a plan. I sent him a letter to his home saying simply to email me. No return address. I checked my mail constantly waiting for his reply. Day after day nothing. After 6 days passed I was giving up hope and my phone rang. I answered it and a deep voice from the other end says "Sheila" I knew exactly what I was dealing with and I replied back. "Yes sir" He went on to tell me that he was hoping I would contact him because now that Mistress Veronica was gone he was very horny and he needed to use my holes to satisfy himself. He instructed me that now that she was gone I needed to step up and take care of his needs. He told me that I was going to be his sissy cross dressing cocksucker and cum receptacle.He was going to use my body as he wanted. I was to call him after I got off work the next day. I was super horny and of course I did exactly as I was told. I couldn't stop thinking of what was to become of me that afternoon all day. He had left the front door unlocked and I entered. I quickly got dressed and went into the room there he was waiting for me stroking his dick. He told me to come over to him. I knelt between his legs. He told me that I was only to put his balls in my mouth and only stroke his cock with my hand. I did as I was told. I kept grinding my hard cock in my silky panties on the bed. I was so horny that I began to beg to put his cock in my mouth. I needed it so bad! I just wanted to feel it pressed into the back of my throat. He finally let me and I feverishly began to suck his cock. He was very verbal telling me what a whore i was for cock and that I looked like a hot slut with his big cock in my mouth.He started to grab the back of my head and guide my mouth up and down. I was dripping I was so hot. Then he would push it all the way in. I would try and pull back and begin gagging and he would just push harder. "Relax your throat whore! You really need to work on that gag reflex and I have just the dick to teach you with. From now on you are sucking my cock every week and make me cum at least once. You hear me whore?" With tears in my eyes I pulled back and said "Yes Master. I am your sissy cocksucker. I want your cum inside my body." He told me he wanted to fuck me. I told him i couldn't do it because i was not clean. I wanted his cock so bad but knew it would be bad to try and get done. He told me that if he couldn't fuck me then he would come down my throat. I quickened my pace sliding him all the way in tickling the back of my throat.He grabbed the back of my head again and pushed all the way in. He told me he was going to cum, I relaxed my throat as I felt his cock begin to pulse in my mouth shooting his load into my hot hole. It felt so good to know that I had my masters cum in my stomach. I knew that I was his for that very moment. He owned me. He told me that I had years of that to look forward to. He said next time I was there I needed to come prepared because I would be tied up and fucked. I cant wait.....
99% (48/1)
 
Categories: BDSMFetishShemales
Posted by tg2027
2 years ago    Views: 3,184
Comments (11)
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4 months ago
Very hot story!
1 year ago
Wow what An Hot sexy HOT !! story!!
1 year ago
VERY LOVELY STORY
2 years ago
So hot erotic, sexy i got so hot
thanks
Jay
2 years ago
very nice story
2 years ago
very nice story!
2 years ago
Very hot, more please!
Bangbangt...
retired
2 years ago
Perhaps I should start answering Craigslist ads hehe
Beverlysm...
retired
2 years ago
Wow i came in mypanties
thanks
Beverly
xoxoxoxoxo
2 years ago
Next time?
2 years ago
Next time?