When I was young I lived with my mom and grandparents as my father had taken off when I was a baby. When I was 10 my mom and I moved out because my mother and grandpa would fight about her dating. My mom always felt bad about me not having a father, as some of the other kids would tease me about it. I was shy and spent much of my time in my own world, a world where I was popular and loved.
My mom loved me, but due to working long hours and trying to find a husband and father she didn’t have much time for me.
After we moved into our new apartment I was alone a lot and that’s when I started to dress in my mom’s clothes. Wearing a pair of panties and pantyhose was my favorite and that was when I got my first erection. I would also wear a wig my mom had worn as part of a witch costume to a party. When I was 12 my mom started dating a man named Bob who owned an auto repair garage. He was divorced with kids but they lived out of state with their mother. After 18 months of dating, my mom and Bob were married and we moved into Bob’s house down the block from his garage. My mom said Bob would legally adopt me and we would be a happy family.
Bob was gruff and didn’t talk much and his main interests were watching sports while having a few beers when not working. As such we didn’t have much in common and weren’t close although I think we tried to make thing work for my mom’s sake. Bob usually worked until 4:00 and my mom worked in the local diner until 6:00 or 7:00, so that would give me a small window to play “dress-up” after school.
This particular day I had put on panties, pantyhose, a sleeveless black dress of my mom’s as well as the black wig. I had started to try to use makeup, and I was wearing red lipstick and black eyeliner.
I thought I looked good that day. I was slim but I had actually been on the track team my freshman year to try to please Bob and my legs and glutes had developed some. I’m not sure if I lost track of time or he was early that day, but as I was vamping in front of my mom’s full length mirror I was startled to hear the front door slam closed and heavy footsteps on the stairs. I totally panicked and froze.
Seeing the light on in his bedroom Bob said “What’s going on in there” as he entered the room. Seeing me like that his jaw dropped. “What the hell is going on, what are you doing ? “he shouted at me “ are you crazy ?” I had never been so scared in my life. As well as being shy , I was intimidated by Bob. His face was getting red as well as the fact he was 6’3”, over 200 lbs , built like a bear with huge muscular arms from years of manual labor. I started to cry. “Please, I’m sorry “ I said “please don’t tell Mom.” He seemed to calm down a bit.” How long has this been going on ? “ he asked. “Around 3 or 4 years” I sniffled. Bob shook his head slowly, like he was thinking. “If I don’t tell your mother you were wearing her clothes you will have to be punished by me. Do you understand ? “ he asked. “Yes ,you can punish me , just don’t tell Mom “I begged.
Bob sat on the edge of the bed .”Come here” he said . I approached him. Moving his arm swiftly he yanked me stomach down onto his lap . “What you need is a good spanking to straighten you out” Bob said. He pulled the dress above my waist and pulled the pantyhose and panties down to my knees. Bob then began to spank me, hard. I screamed and cried and tried to get away but his other arm easily held me down.
“Stop whining or I’ll give you twice as much “ he said gruffly. I bit my lip although tears still rolled down my cheek. After 25 or 30 smacks he paused and said “Now 1 for every year you’re old because of your whining “ he said. Bob was much slower now, pausing after each smack before delivering another. I realized to my alarm that I was feeling a large and growing bulge pushing into my stomach and even worse I felt my penis begin to harden. After 14 smacks he stopped smacking me but held me down another minute before letting me up.
As I stood Bob could see my erection.” Look the little girl liked the spanking. That’s some little girly dick you have.” My penis was only 4 inches hard and no thicker than one of Bob’s fingers. Bob stood up and started to unbuckle his belt. “No please don’t use your belt on me, I can’t take it “ I said. He laughed and said “I’m not going to whip you, I’m going to treat you as you deserve.” Bob then proceeded to undo his fly and push down his workpants and boxers freeing his cock. It suited him. It had a big mushroom head, all purple, and an angry looking red shaft , around 7” long and massively thick like Bob.
“Get on your knees slut, if you can’t be a man, then you can service one “ he ordered. Too scared to refuse I did as he said. “Suck it whore “he grunted and slapped my face with his cock . It hurt a lot. I opened my mouth as wide as I could and he plunged deep in. He went so deep in that I gagged , which made Bob laugh. “Now don’t touch it with your teeth or else “he grunted. Bob proceeded to work in in and out just enough to avoid gagging me. After 5 minutes , my jaw ached due to his thickness but Bob then grabbed the back of my head ,drove deep and grunted “I’m cumming slut, you better swallow it all .” His cock erupted in my mouth and it lasted a long time but somehow I swallowed most of it. “Good slut “he said “it’s been a long time since I’ve had a good blow job as your mother thinks she’s too good to do that. She thinks she’s too good for most sex if you want to know the truth.” I said nothing, I just knelt there with the taste of Bob’s bitter cum and sweat in my mouth.
“Get to your room know “ Bob said. I stood up and shuffled to my room . Bob went into the bathroom ,then quickly into my room .”Take off the pantyhose” he said. I sat on my bed and rolled them down and off .”Now pull your panties up” he ordered and I did.” Turn around and let me see that cute little ass” Bob said . I did as he said. Bob picked up the panty hose, grabbed my hands and using the hose tied my hands to my bedpost. Sitting on the bed Bob then showed me why he went in the bathroom. In his hand was a jar of Vaseline. “Do as you’re told or it’ll be worse” he said as he put a finger deep into the jar . Pulling the side of the panty away he began to force his finger into my virgin ass. He struggled but he forced it in.
“That is one tight hole” Bob said “this will be fun.”
“Please don’t “ I begged “its too big. I can’t.” Bob drove it deeper and said “I will and I bet a little slut like you will love it.” As he continued to finger fuck me , I started to feel funny .My dick got harder and some precum leaked out. Seeing this, Bob then forced a second finger in me making me moan. Not being able to wait longer ,Bob pulled me onto the bed on my stomach, placed a pillow under my groin and began rubbing his cock with a lot of Vaseline. “Don’t worry I’m giving you your wish, making you a woman” he said.
Bob then spread my cheeks with one hand , while his other guided his thick cock to my now slightly looser hole. “Breathe in and out and relax, it’ll be better that way “ Bob said. I did as he said and on my fifth inhale he forced the head into me. I screamed “Take it out, its too big. You’ll break me in two.” Bob grabbed my neck and applied pressure until I shut up. “Don’t fight or it will hurt more.” he said. He then pulled out before putting it back in a little further. Bob continued doing this until on the tenth time he buried to the hilt in my ass. “You are so tight, it feels so good” he groaned.
He waited a minute before he started to move in me. All his pulling in and out and taking it slow had helped me. It still hurt but not nearly as much as it had. Bob slowly started to fuck now, slowly pulling almost all the way out before plunging balls deep again. After about ten minutes of this Bob totally pulled out, leaving my ass feeling empty.” Turn on your back, I want to see your pretty face while I fuck you” Bob ordered. “Do you think I’m pretty?” I asked as I turned over. Bob positioned the pillow under my ass with my hands still tied above my head and knelt between my legs. “Yes you’re my pretty little girl” he said as he lifted my legs up and plunged all 7 thick inches into my tight hole. “Are you my good little girl. Daddy’s girl” he said as he started to fuck me hard.
Bob had never used the term daddy with me before and it made me happy. “Yes Daddy I’m your girl” I said. This seemed to please him as he leaned down and gave me my first kiss. He kissed hard forcing his tongue in my mouth, but I loved it. As he pounded me in this position his hairy bearlike torso ground into me and my panty covered dick. “Wrap your legs around Daddy’s waist “ he said and I did allowing him to grind harder. I couldn’t take any more. “Daddy I’m cumming “ I said and I felt myself explode in my panties. As I came my body [ and ass ] tightened driving him over the edge. I felt him stiffen and fill my hole with his hot cum.
We lay there entangled in a daze until realizing the time he got up and untied me .”You better clean up and return your mothers dress” he said. Looking at the state of the panties ,covered in cum he told me to throw them out. He started to leave but returned and kissed me hard while squeezing my ass in his big hands.
If readers like this story, let me know and I can tell my further [and father ] adventures.