I was an only child to a single mother for all of my life. Well, that was the case until my Mom started dating Chuck. I was fifteen when fourteen when Mom met Chuck and married him a year later. I wasn’t the typical “young man” and didn’t try to challenge Chuck, who was proud to assert his Alpha male status when Mother wasn’t paying attention. You could say Chuck and I never really got along, although I was glad he made my Mother happy.
Everything changed during the summer of my Junior year in high school. Chuck worked as a handy-man/contractor and owned his own house renovation business. That summer, everything to include myself thought it would be good idea for me to work with Chuck. This would give me some “bonding” time with a father figure and maybe learn some helpful skills for later in life. Not to mention the fact it would give me spending money. I’ve seen the worst of Chuck’s behavior, I’ve dealt with him for a couple years for free, at least this time I would be getting paid.
As anyone in the contactor business know, work isn’t always steady, as I soon found out. Chuck would tell me to take the day off because he couldn’t afford to pay me for the piddle job he had lined up for the day. With Mom at work and Chuck out the house, this gave me the perfect time to play dress up. I’d been crossdressing since I was eleven. For me it was fun and a great way to pass the time while doing some choirs.
I get carried away, listening to music as I prance around the house in some of my Mother’s clothes. Well, this day, Chuck finished up quick and came back home to pick me up for a new job he just got called on. Sometimes Chuck wasn’t a total asshat and brought me lunch to eat. He had on this day and I don’t know how long he had been watching but, I heard the bag of food hit the ground, almost followed by Chuck’s jaw. I probably turned a couple shades of red and green. I felt sick to my stomach and immediately ran to my room. I could hear Chuck picking up the food and after a few minutes, he yells,”I’ll be right back, going to get some more food.”
By this time, I’m completely freaking out. I’ve changed into my boy clothes and my mind won’t stop running through different scenarios. Is Chuck going to tell Mom, he’s cool sometimes but a total prick the others? Did he think I was attractive? I’d never really thought of Chuck in a sexual way because I didn’t find him attractive but, what if he thought I was cute? Is he going to force himself on me or blackmail me? He sometimes plays the role of shady contractor well. Chuck is a mid-40s, balding, tall, and overweight man. I was a 16 going on 17 year old, fragile, 110lbs sissy-boy in his eyes for sure now.
I decide I shouldn’t be in my room when he gets back with food. I’m starving and freaking nervous though. I walk out, peaking to make sure he’s not back yet. I plop down on the couch and watch TV as I would normally do. A few minutes later, I hear Chuck come in. He almost yells, “I’m back”. I holler back that I’m in the living room. He proudly struts into the room and plops the bag of food on the table in front of me. “I brought you something to eat, we need to get going soon to take care of this job in a few.” I slowly reach for the bag, not even being able to look at Chuck. I cannot believe he hasn’t thrown my crossdressing in my face yet. I know it’s only a matter of time though. We quickly scarf down our food and I grab my shoes, soon heading out for the day.
A few weeks pass and I cannot believe Chuck hasn’t told my Mom, she would have surely flipped out and sent me to a psychologist. He also hasn’t brought it up with me either. I’m actually starting to think he is a decent human being now. One thing I hasn’t mentioned yet, Chuck has a home office. It’s near my room, away from my Mom and his bedroom. In this home office, there is an old rickety computer chair that creaks loudly when you sit and move around in it. So, every he sits in the chair, and surfs porn late at night when he thinks everyone else is asleep, I hear. It’s a very slight and quick sound that I’m sure he doesn’t think anyone else can hear but, it’s just high enough pitch for me to know. This has gone on for a year.
I’ve seen his porn history before when he’s forgotten to clear it. Nothing exciting, just young girls doing what they do with men. Well, a few days after he caught me; I found that he searched for some young crossdresser porn. This turned me on so much. I still didn’t find Chuck attractive but, some part of me just wanted his alpha male father figure to completely dominate me. I’ve been fantasizing about how that situation would play out since I found out. Finally, I’ve worked up all the nerve I could muster and wanted to see where this would lead.
One night, about two months after Chuck had caught me crossdressing, I hear him sit down in his old computer chair. I start getting ready, slipping on some black satin panties and cute pink nightie I’ve stashed away from my Mom’s old lingerie collection. My hair, brown, was already long for a boy and I put some bright red lipstick on to try to create a more feminine look. I looked like a tom-boy at best but, that’s as good as it’s getting tonight. I start to hear the creaking of the chair slowly increase in pace. I know, it’s time. I slowly crawl out of my room. I’m literally crawling, trying to create a seductive and submissive approach. My heart is pounding and my panties stiffen as the sexual thoughts a running though my head.
I peek into the round around the desk, the desk is faced the wall next to the door. He almost immediately notices me. He looks surprised and has stopped actively masturbating. I look him square into the eyes, probably for the first time ever. I slowly continue to crawl towards him, until I’m within inches of him crotch. My eyes stay locked and my mouth almost sew shut as I try to open it. I’m trembling as I stand on my knees in front of him. I can barely speak the words I’ve fantasized about for the last few weeks. “Can I take care of that for you?” I feel like an hour passed before I saw him shake his head yes. I exhale in relief and slowly reach out for his cock. I look down for the first time and see an erect, solid 4 inch cock in front of me.
I have to say I was a little disappointed but, relieved at the same time. Chuck pulls his hand away as I wrap my fingers around it. It does look bigger in my hands. I give it a few tugs before I lean in to give it a kiss. The chair lets out a loud creak as Chuck leans back. I give it a few kisses and start working my lips around it. It was as thick as a wooden broom stick. I start to feel Chuck’s hand on the back of my head as I slowly work more and more of him into my mouth. It wasn’t long before I was face deep on his cock. I can hear Chuck moaning and breathing hard, this turns me on even more. I feel him grab my hair as he helps me build up speed and keep rhythm.
A few minutes pass that felt like forever. My jaw was beginning to lock up and get tired. Luckily, I hear him mumble something about cumming. I’d never made it this far in my fantasies. I wasn’t sure what I should do, does he want cum in my mouth or not? Do I swallow? I’ve never tasted cum before, is it going to make me throw up? All these things start running through my head. I decide I should ask him but, before I can pull him out of my mouth, he pulls my head down and shoots his massive, mucus-like load into my mouth. He holds my head down and tells me to swallow. I have no choice at this point. It’s difficult to breath and I’m starting to gag on his cum. After a few seconds, he lets me up for air. Cum is still dripping out my mouth while he tells me I did well. It felt like a barrage of questions, “How did I taste?” “Do you want me finish you off?” I lean back and sit on my butt to stretch out my legs while getting catching my breath and getting my bearing. Chuck goes on to say with a smirk, “It looks like you’ve already cum in your panties.” I look down and yes, it does appear I’ve already gone soft in my own cum soaked panties. “I’m good, thank you though” I respond kindly.
Chuck looks at me and then down at his cock, it’s covered in lipstick smudges. “Your Mother will go nuts if he catches you wearing lipstick, especially if it’s smudged all of your face and my dick. You need to get yourself cleaned up and I’ll do the same.” I node in agreement and slowly get up to walk out the room. Chuck slaps my panty covered ass with some force, and says, “You should do this again. Have a good night.”
Source: reddit.com/r/eroticliterature/comments/71wxv3/crossdressing_teen_with_stepdad