My real first time playing a girl

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My real first time playing a girlLet me start with a little back story of how all this started. Me and wife had been together since high school. When we would have sex it wasn’t uncommon for my wife to stick a finger or two in my ass. At first it felt weird, uncomfortable and hurt a little. But after a while I just said screw it, she let’s me play with her ass so she can play with mine. Eventually it became the only way I wanted to have sex, and I wanted it harder every time. Unfortunately me and my wife split when were 23. We divided up our stuff and money and went separate ways. After the divorce was final I started applying for jobs online in all the major cities, I was ready for a new start. I found a factory job outside of Miami. When I flew out there to look at rental homes, I toyed with the idea of looking up gay,lesbian, and trans Hangouts. I didn’t visit of them that time. But I did find a small place to rent about 40 minutes away from my new job.Getting the new place set up and settling into the new job i found myself watching porn where men were dominated, by trans women or strapon. The urge from my ex wife fingering my ass was always there when i played with myself. I ordered some small dildos discreetly online. And worked my way up enjoy a decent size rubber cock in my ass. Eventually I started watching just sissies being fucked and wouldn’t ya know it, before long I had order myself sexy women lingerie. It took a few orders to get the size just right. I liked the way it made me feel when I had it on but I didn’t like seeing all my hair. I started shaving my whole body top to bottom. After showers I would rub myself with lotions and oils till my skin was perfect illegal bahis and soft to the touch. But even that grew old and dressing and fucking myself as a girl wasn’t enough any more. I went back to the drawing board and searched for bars to go to, but ended up finding adds for “massages”. They were pretty expensive, but not out of reach. They had a fetish section and trans section. I repeatedly looked at them almost daily fantasizing. I thought about it for a looooong time before I ever emailed one of them. But one day I did.I sent the email and waited nervously for a reply. After a few emails confirming each other was real, and learning what she will do and what I want done. it was determined a “massage” was getting set up. All to be paid up front with cash only. All that week at work was normal till Friday night. I got home from work and she was going to be there in 5 hours. I couldn’t believe it I was so nervous some strange lady was coming to my house and going to treat me like a whore sissy. I get in the shower and prep my ass and body like normal. I dry off and put my sexy dark blue panties and bra and fishnet stockings on and wait for her to show up. The last half hour before she was to arrive was agonizing, was it really going to be her or was the police gonna catch me for paying for sex dressed like a girl. I waited in the living room till I heard a car door, my heart was just pumping out of my chest, and my hand trembled when she knocked and I opened the door. It was her from the pictures. I stood back from the doorway while I invited her in hoping no neighbors would see me. She came in and I closed the door. She introduced herself as I was closing the door. Hi illegal bahis siteleri I’m Heather. Hi Heather I’m Jon.We settled the payment right away. And she asked were the bedroom was. She bent down and grabbed a small bag she brought with her. She stood up and looked me in the eyes and told my something that got my dick hard as rock. She said get your fucking sissy ass up and to the bedroom now. She followed super close behind me and closed the bedroom door after we entered. I felt her hand wrap around the back of my neck hard. She pushed me towards the bed, making me fall on to my stomach, and she slapped my ass with such force you could tell she was well practiced in this. I couldn’t help but let out a groan of pain and she smacked me again just as hard. I myself was astonished at how fast this was happing and that it was actually happing. She spanked my ass for about 10 minutes while calling a bitch and pushing my head in the matress. She pushed my head down hard and told me not to move or make a sound. I heard her small bag unzip and coul hear her dig through it. I heared her pull something out and walk up behind behind, she grabbed my right arm and pulled it back and slipped one cuff on and then cuffed my hands together behind my back. She pulled my hair back and yeld are you ready sissy. Yes I’m ready. She yanked my hair so hard I thought my neck was gonna snap. What did you say sissy. Yes, I said yes. She turned me over and it all began.I could now see the strapon she had put on while getting the cuffs out of her bag. She took out a condom and put it over the strapon. She kneeled on the bed and started rubbing my hard on asking me if I wanted to be treated canlı bahis siteleri like a sissy. As she rubbing my junk she started getting aggressive till she had my cock out of my panties and was tugging and squeezing and pulling my cock till it would hurt. But I liked it. As she got off the bed she d**g me close to edge. Gathering up my pillows she put them under my back and continued to stroke my cock harder. She suddenly stopped and smack me right in the chest, turned around and walked away. She went back into her bag and retrieved a bottle of lube. She lubed up my cock and start rubbing up and down on my dick and balls. Every rub down she would drag a finger closer to my ass. And I would moan wanting her to finger my ass. She grabbed my cock and balls in a fist and pulled straight up. Then I felt it she was pressing a finger against my asshole. She got in and slowly worked her way up to two fingers deep. She started stroking me again and fingering my ass pretty hard at the same time. She instructed me tell her when I was going to come. Trust me it was going to be soon. As I could feeling my cum getting ready to come I tell her. She removes her fingers from my asshole, grabs the tip of her strapon and shoves it right in my. She starts going in and out, and stoking my cock. As I cummed she thrusted her didlo into me hard and deep. She squeezed every drop of cum out of my cock onto my stomach. She pulled away from me, uncuffed me took her strapon off. Wiped herself down with a towel got dressed, grabbed her stuff and said call again if you had a good time. And walked out the house. I laid there dressed as girl, covered in cum and felt like a cheap slut.. and that is how I learned to love being a sissy. Sorry that the story isn’t written professionally. I’m not a writer just wanted to share my story of how I became loved being fucked by dominant women and shemales. I hope you enjoy your deepest desires like I do.

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