NOTE: As I stated in my profile, I am definitely NOT an author. I do like to write and this little fantasy was spinning around in my head for a few days. I figured it’s been a long time since I wrote something so here it is. Standard story for me, no real plot, no story, sex. Mainly an outlet for me to explore some sexual fantasies. But, I hope you enjoy my fantasies anyway! (BTW, this really worked good in my head, harder to get down on the screen)
It started as a regular Tuesday afternoon. Dawn, my wife of two years was at work and I was sitting at my desk in my home office, working. At about 1:20, I heard a car door slam and the dogs ears perked up as my step-daughter Hannah came through the front door. I turned around and waved a little “Hi” and went back to work. I heard her go trudging upstairs to her room as I turned my chair around.
Twenty minutes later, I was engrossed in work and didn’t hear as Hannah came down and plopped in the chair behind me at the other computer.
“Ummm, Dave?” I heard from behind me.
“Can I ask you a question?”
“I, uh, I don’t know how to ummm...” there was a pause for about 2 seconds. “don’t know how to ummm, you know, uhh play with my ... uhh masturbate and I don’t want to ask my mom because it’s too weird and I want someone to show me what to do. “ It all came out at once, quickly. I stopped typing and sat there for about 10 seconds before turning my chair around to face her.
Hannah wasn’t the prettiest teen there was but she wasn’t ugly. She was pretty tall at 5’8 but she was a bit large at around 230lbs. Dark hair, dark eyes and olive skin rounded out her latina ancestry.
Most of her friends were gay and transgender and while she hadn’t said anything “official” to us we kinda figured that she fell somewhere in that group. She often dressed more like a male, especially when she needed to dress up and go somewhere, usually wearing slacks, button down shirt and a tie. But she didn’t have any other real male tendencies other than not shaving her legs which were never all that hairy anyway.
Today she was wearing a regular t-shirt and a pair of red gym shorts, sitting on the desk chair across from me with one leg tucked under and the other just swinging back and forth nervously. I could see her face was a bit red even though she was looking down towards the floor.
I thought for a minute about what to say, since she didn’t want to go to her mom, I didn’t want to make her feel stupid and invalidated coming to me.
“OK, well I appreciate you feeling comfortable enough to come to me about this”. I said slowly. “Can I ask you a few questions first?”
“Have you tried masturbating before?” I asked.
“Well, uhh kinda. I umm tried rubbing my uh, you know, my umm vagina, but even though it uh ... felt kinda good. Nothing else really happened and I don’t feel like I uh, I am doing it like, right.”
“First of all” I replied, “Vagina sounds too clinical, just call it your pussy. Sounds better when talking about masturbation. How many times have you tried playing with your pussy?”
“OK, well uh, I only played with it a couple of times” She replied
“Just recently? Is this the first time you’ve tried?
“Yeah, I just haven’t been interested in anything sexual before but there’s this uh, well, there’s this ummm ... person at school that I kinda like and a couple of days ago when I was in my room I started feeling kinda tingly and realized that I was rubbing my uh brea ... I mean tits and it felt uh, felt really good.”
“OK good, and then what?” I asked, hopefully not too quickly. Even though she was my step-daughter, the thought of her rubbing her pussy was starting to have an effect on my cock.
“yeah so, then I started rubbing my uh, pussy outside my shorts and that felt even better so I kept doing it for a while, but then it just felt weird so I stopped. Even though it still felt kinda good.”
“You didn’t rub it under your shorts?”
“NO! I mean ... well ... no, it just felt weird and I like I didn’t know what I was doing. But then yesterday I did it again and this time I did it for a bit longer but nothing happened and I just stopped because I felt frustrated.”
“I can believe that!” I chuckled. “OK well, just a few more questions and suggestions. First, I know this may seem like a silly question but how well do you know your female anatomy? Like, do you know what your clit is and where to find it?”
“Umm yeah I know and that’s what I thought that I was rubbing yesterday I mean like it felt so good but I thought that I would have a uh, you know, orgasm or something if I rubbed it.”
“I have to admit that I don’t know female anatomy as well as male anatomy but I can tell you that a little bit of rubbing doesn’t always equal an orgasm. “ I replied. “But let’s work on that”
“OK” she replied.
“What exactly did you have in mind when you came down here to ask me about this?” I asked as I looked pointedly at her.
She looked down at the floor again, her leg swinging a little faster now. “I uh, I wanted you to show me ... show me how to play with myself.”
She stopped and looked up at me but I just sat there and just raised my eyebrows a bit.
“OK I heard from a friend that if you uh, have someone else do it ummm for you it feels way more better.” She continued.
“So, you want me to show you how to masturbate by helping you rub your pussy with you, or did you just want me to rub you and get you off?” I said it a bit sternly this time as I wanted to make sure she was clear with me about what she was asking.
My cock had a different idea at this point and was hard as a rock. It took everything I had to not try and adjust it in front of Hannah and give away how turned on I was right now.
Her head looking down at the floor, she replied “Both”
I stood up and walked around to the back of the chair and leaned down next to her head and said quietly into her ear: “OK, I’ll do this for you. But, here are my conditions. One, you commit to this 100%. I don’t want to waste my time trying to help you and then you change your mind. Two, you listen and do everything I say without question. If you agree, then I promise that I will help you learn to masturbate and you’ll have the biggest fucking cum. Do you agree?”
When I said the word “cum” she stiffened a little and drew in a sharp breath. She exhaled slowly and after a couple of seconds uttered the word I wanted to hear.
“Good, go upstairs to your room and I will be there shortly.”
She got up and quickly headed up the stairs to her room. I took a moment and adjusted my cock in my pants. I took a deep breath and started walking up the stairs to her room. The door was open and she was sitting on the bed looking a little nervous. I closed the door behind me and locked it.
Quickly, she stood up and I walked up behind her.
“First lesson is getting to know your body. I want you to take off all your clothes.” She reached for the bottom of her shirt and hesitated for a moment. I started walking to the door.
“This is your one chance Hannah. If you want my help, if you want to cum, then you do what I say otherwise this is over and I’m going back down stairs. This is not the time for you to be modest about your body.” I said.
She took a deep breath and pulled her shirt over her head. She had on a simple white bra that covered her ample 42C chest. She pulled down her shorts pulled them down, finally getting them off and tossing them on the floor. Reaching around back, she unhooked her bra and held her arms close to her body before taking a deep breath and letting the bra drop to the floor. She started a couple of times to cover up her tits with her arms but looked at me and stopped, keeping her hands at her sides. She was very fidget-y, like she didn’t know where to put them.
“I said all of your clothes.” As I crossed my arms and looked expectantly at her. She sighed and grabbed the waistband of her green panties and pull them down to her ankles and kicked them off. At this point, she stood back up, her arms at her sides and looked at me, waiting for her next command. Looking at her body I would definitely put her in the BBW class. Her tummy was round but with a weird firmness that comes with being 17, leading down to a wiry black bush and thick thighs.
“Very nice” I nodded and started walking towards her. She was still fidgeting as I got up to her and walked around behind her.
I reached up and touched the top of her back near her spine and gently ran my finger down her back, tracing her spine until I reach the top of her butt. I used both hands to reach down both cheeks and massage them.
“How does that feel?” I asked as she sighed and leaned back a little towards me.
“Perfect. Now, I want you to set up a scenario in your head. This person you like, they are over here in your room. You are alone. They are now me. I want you to think about what this person is going to do to you now. You are naked in front of them, vulnerable. Start playing out that scenario in your head”