I’ve been a full time sissy for several years now but I’d like to tell the story of why and how I got here. As I’ve told in my other stories, I’ve had good naughty sex with hot hung men but this time was the game changer.
Ok, so I was actually married to a woman for 7 years, a very sexy petite woman I might add. She had no idea I had a feminine side and knew nothing about me dressing on the side. Actually, I hadn’t dressed the whole entire time we were married. We bought a house in a nice neighborhood and we both had great jobs. About a year after we bought the house, I began to notice small changes in her. She began to get a lot of attention at her job from men. We only had one vehicle so certain days I was off, I would take her to work and she’d hitch a ride home. The ride home was from an elderly man I was told until I found out it was not an elderly man and they were fucking! I was destroyed and heartbroken. I never thought this would happen to me. I felt like I would never trust anyone ever again.
Fastforwarding all that drama, we divorced. It took me a bit to get over all that, depression set in and I secluded myself from family and friends for a few weeks. Here’s where things began to change from me.
I was sitting on my couch and began to watch trans porn for the first time in years and instantly I feel back into it. I became so horny and hard I began to jack my cock while watching these beautiful fit chicks with dicks living their best lives and pleasing big dicks. It felt so good as I nutted so hard fantasizing about cock. I then thought to myself, damn I now live alone so what’s stopping me?
The next day I posted an add on craigslist(back when you could), I described myself and what I was looking for and that I could host. I’m very picky so they had to be in shape, clean, groomed and hung. I shaved my entire body every inch. I went to town and bought makeup, wigs, brushes and clothing. Let’s just say I made a day out of it. As I completed my shopping I couldn’t wait to get home and dress up. I’ve always been in good shape as I work out and tan often.
First thing first, I applied all the foundation, eye liner and lipstick that looked superb. It all came back to me while doing the makeup and the smoky eyes turned out great. I was so turned on but yet I still thought about my ex every few minutes it seemed. Sick of laying around pouting and feeling sorry for myself I decided I’m gonna actually do this. I checked my replies for the add after completing my makeup and actually found 27 replies wanting to pound my sissy ass. Mostly sickos that I instantly deleted but however, one guy stood out. His email was Batman and he appeared to be in his late 20s, good shape with well groomed facial hair. We chatted for a few minutes and set a time of 8pm for him to come over. He loved approximately 20 minutes from me.
I continued my dress up as I had plenty time to spare. After changing out of outfits I wasn’t feeling I decided on a tight pair of jeans and a really tight pink shirt with blk heels. Perfected my blonde wig and looked into the mirror. I was actually super shocked how good I turned out. I was so damn nervous and wasn’t sure I wanted to go through with this. I fixed myself a drink and sat on my bed for a minute weighing my options. I thought to myself, I’ve came this far and I have a man very excited to come see me, hell I even thought if I wasn’t feeling it once he got here I’d just say so. As it got closer to time I contacted him and he said he still wants to come on. I typed out please come over I wanna have some fun and I pressed sent! It’s a done deal I said to myself.
Door bell rings as the click of my heels on the hardwood floor could be heard. I opened the door to a handsome man smiling at me. Smiling back I told him to come in. He gave me a small hug and proceeded to the living room. We sat on the couch for a bit talking and not necessarily talking about sex. He told me he’s been with other sissies and that he loves them more than girls. I noticed he was hard as a rock so I knew he wanted to put that dick to me and the more comfortable I got the more I wanted it in my mouth. I told him to excuse me while unused the restroom, I only did this to change into a slutty lingerie set. I quickly undressed in my room into a white bra, white panties and I put on a white pair of thigh high stockings.
Showtime as I walked back into the living room into his view. I said”I hope you like lingerie”, he at once stood up and unexpectedly to me we locked lips. I thought damn I’m kissing a man!! He was a take charge guy as he softly lead me to the couch and laid me down on my back. He started kissing my thighs and rubbing my flat chest as if they were huge tits! He slowly began to rub my sissy clit through my panties as it slowly but surely started to grow. Damn this his felt to good and right! After several minutes he pulled my panties to the side and started eating my ass, OMG it was heaven on earth. I started to moan and skerm and his tongue flickered my ass. I definitely wanted this man’s cock inside me as I was fully erect. I used my hands to push my ass in the air so I could watch him tongue fuck my booty. He then took his hand and fully gripped my erect cock as I almost lost my breathe it felt so good. At this point he was saying “don’t like that baby?”, all I could do was moan and say fuck yes I do!
This continued for it seemed like forever, I would come so close to cumming but it remove his hand from my dick because I didn’t wanna cum yet. This kept happening until I said “I want that dick inside me baby”, he stood up and finally removed his pants and he was wearing the sexiest fuckn tight underwear that showed the outline of his huge dick.
He slowly took off his underwear as a 7 inch shaved dick presented itself. I at once attacked it with my lips as if it was gonna walk out the door. I was sucking and taking his dick to the root, I was thinking to myself with every thrust, I’m so fuckn gay, I’m such a little cock drunk sissy whore, I truly am though and I still am. I licked his dick up and down sucked his balls until he stood me up and lifted me up. He held his hands on my ass cheeks as I wrapped my legs around him with my arms wrapped around his neck. At once his dicked slid inside me as it was lubed up due to my dripping saliva from sucking him off. My eyes rolled as his dick began to press against my prostate causing my toes to curl. I let out some moans if never let out before. My massacre was running as this man was fuckn my ass like he loved me. The best feeling in the world is feeling ashamed but not stopping. Feeling guilty because my parents would be so ashamed if they knew their son turned into a hot sissy dick hungry whore. His dick was hitting all the spots and I whispered in his ear to never stop. My cock, still fully erect was sliding on his abdomen every time my ass lowered onto his cock. After several minutes I felt my cock getting bigger and bigger as I began to get light headed. I knew what was coming and my God it felt so good I couldn’t stop. I at once had an orgasm so hard all I could do was hold on tight to him with my mouth wide open. I came so hard I was blacking out, moaning as he started kissing my ears. He then lets out manly grunts as he started shooting loads of warm cum into my butthole marking his territory. We fell to the floor as it was over. Laying in stockings with another man’s cum dripping out of my ass I knew I was done with pussy!
Batman left my house haha as I knew I would be taking dick regularly now. This has catapulted me into becoming a full time sissy as I dress for work and everyday life.
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