It was my 30th birthday. I felt so weird about being older. I was definitely supposed to be an adult by now. I’d spent most of my 20s fucking escorts and streetwalkers. It was a hell of a ride. I did almost everything I ever wanted to do sexually. I’d been addicted to porn for 25 years. The internet had taken me to some of the darkest places one could go. My mother texted me. She was definitely the spawn of satan and most everything bad that happened to me was because of her. I ignored the text and continued having no contact with her. One day I noticed that 2 types of porn had greatly out numbered everything else on the old hard drive. I was masturbating to either tranny porn or mommy roleplay. When I was lucky enough to find a melding of the two, I would blast my biggest loads from masturbating. I hated wanting something so specific that I thought I would never find in real life.
There I was celebrating alone at this club I’d never been to. There were trannies, drag queens, and gay guys everywhere. There I was drinking alcohol and trying to enjoy music that was too loud for my tastes. I turned and caught eyes with a beautiful crossdresser. She was like something out of a dream. I wondered how long she’d been coming here, I wondered what her name was, I wondered what her cock looked like… Ha, I wondered everything and was so afraid to even smile at her. She sat beside me and I offered to buy her a drink because what’s the point of drinking liquid courage if you’re going to waste it? Surprisingly she asked for some fruity concoction that only a girl would order. I, as a man’s man, was drinking straight vodka and chasing with beers. I complimented her on how she looked. I refrained from using the word beautiful because I didn’t want to come on too strong. I told her she was very pretty like I was some stupid k**. She touched my bald head and neck and shoulders. She said, “Well, you certainly feel like a big strong man.” I laughed it off and told her it was my birthday. She said it was hers too. I was 30 and she was 69. “Go on”, she said, “Make your best 69 joke.” I told her “There’s nothing funny about how much I want to 69 with you. If I was the kind of guy that danced, I would ask you to dance.” She led me by my hand to the dance floor, “Show mama what you got, young man.” I was hard as a rock and clumsily moved my body around just doing whatever I could to stay close and touch her.
We exchanged names and she invited me to sit at a booth with her. As soon as we sat down she had her hand down my pants. “Ohh, baby boy’s happy to see me huh?”, she asked. I told her that I’d never met anyone like her. She kissed me hard and deep, her tongue dancing around my mouth. She was in control, but my instincts kicked in and I grabbed the back of her head. I caressed her face. I pushed my tongue into her mouth while she jerked me up and down under the table. I asked her if she had a boyfriend. I felt like an idiot as soon as the word left my mouth. She invited me back to her place, “Come on, mama’s boy. You wanna go for a ride?”
At her place we got comfortable on a couch and she served me some wine. I couldn’t believe what was happening. We started kissing again and this time she put my hand on her hard cock. “You wanna make me happy baby boy?” is all she had to say before I took her into my mouth. It didn’t take long for her to squirt the sweetest bestest load into my mouth. “Don’t swallow it yet”, she told me. I wanted to drink it sooooo bad. Then she kissed me and we shared the taste. I finally swallowed some and began to fall in love with her. She led me to her bedroom and told me to wait outside her bathroom while she got ready. “You better not be peeking at me”, she said. I watched her stand and use the restroom. It was very sexy. I watched her take off her dress and grab a bottle of lube. She shoved the end of it into her ass and squeezed a lot into herself, then she took her fingers and dug around inside that sexy puckered hole. I was in a trance, hard as a rock. I thought back to being younger and how my mother would stay naked around the house just to torture me with what I couldn’t have. She came out of the bathroom, “MMm, is that for me?”, she said while looking at the tent in my pants. Before I knew it, my dick was out of my pants and into her mouth. “I know how to take care of you, baby. Just let me”, she whispered to me. I was transfixed by every inch of this beautiful tranny. I wanted her cum in me, on me, all around me… I wanted my cum deep inside her ass. I felt like only then would she appreciate just how much I was in love with her. I laid her down on her stomach, spread her cheeks and pushed myself inside.
“Take mommy’s body, baby boy. It’s yours… this hole is yours… use me… breed me baby.:”
I pumped slow and steady and let one word slip out of my mouth between panting and grunting.
“Mommy”, I whispered as I came harder than I ever had before.