(Here is a new story. I explore a lot of weird things I wanted to mentally work out myself. It was cathartic and I decided to share it. I did very little editing, so forgive any typos. I have several chapters so I will look for feedback on whether this community wants to see the rest)
My name is Heather, and I am a seemingly normal 17 year old girl to everyone I am acquaintances with, except for the fact that I lost my mom a few years ago to the opioid crisis. Everyone is sympathetic. She had back pain from a minor car accident and was given a prescription. She spiraled out of control for a couple years until she eventually overdosed. I never knew my birthday father, but my mom married my stepdad when I was 5, and with that I instantly had a 1 year old step brother that he had from a previous relationship. She had apparently left him with the baby and ran off with her boss. So for the past few years it’s been just me, my stepdad Tony, and my step brother Jack.
Growing up with Jack was probably better than growing up a single child. I didn’t mind looking out for him or babysitting him, and we usually got along and had fun together. Jack has had a tough and dominating personality as long as I can remember. He loves to win at everything like board games, video games, and thumb wars. He also likes being in control. If we watch tv, he likes to hold the remote, and that sort of thing. I on the other hand am more passive, so it doesn’t bother me to let Jack win or change the channel or whatever. I suppose our contrasting personalities are part of the reason we get along so well.
Honestly I’m not sure how things got so unorthodox between us. I guess it was a day a few months ago when we were screwing around playing the game where you interlock fingers and try to squeeze the other person’s fingers until they gave up. We had played it since we were kids. Jack always won, but I never wanted to give up. He’d squeeze my fingers almost to dust, but I would not give up. On that day though, maybe it was that he was 13 year old now and was thinking about things in new ways or a sudden realization that I always take quite a bit of pain, but he stopped squeezing and said “Heather, why do you let me hurt your fingers so much before giving up? Wouldn’t it be easier to just surrender?”. I guess I never thought about it before. After several quiet seconds I said “I don’t know actually. I mean it hurts, but I like seeing how much I can take I guess”. He thought about my response and asked inquisatively “so what if the game was slapping each other across the face? Would you still want to see how much you could take?” I said “probably, but who wants a bruised up face? You know I can take a lot.” Then I paused. My brain filter tried to activate but it didn’t work and I said “but my butt cheeks nobody would see”. I had on skinny jeans and a tee shirt, which was typical for me.
It somehow evolved through discussion that it wasn’t really if I could take more pain than him, it was about if I could push myself to take more than I thought I could. Twenty minutes later my 13 year old step brother had his 17 year old step sister draped over his knee spanking the seat of my jeans. My long dark brown wavy hair hung down over my face. That’s when Tony walked in and saw us getting home from work. We got up immediately and I went to my room. Jack had spanked my ass bright red and it hurt, but I would not have given up yet had Tony not interrupted. Dinner was eerily quiet and awkward feeling. Later, after I’d gone up for bed, Tony came to my room. He said “I talked to Jack and I know what was happening when I got home. You know your younger step brother is not the boss of you right. You don’t have to do what he says even though he’s stronger. You know that don’t you Heather?”. I nodded and said “I know. We were just goofing around. I didn’t mind. I agreed to it”. He said “Ok. I won’t say that you can’t do what you want. It was your ass getting the beating after all. I just didn’t want him bullying you.” I said “he wasn’t. I promise”. Then he tucked me in saying “Ok honey. Do what you want, but don’t do anything you aren’t comfortable with”.
The next few days were awkward with Jack, but that eventually faded. We were watching tv together and Jack said out of the blue “you were about to give up soon anyway”. I said “No I wasn’t. Not even close!”. He said “well then I give the credit to your jeans. I bet they took a lot of the sting out”. I sensed he wanted to spank me again. I don’t know why, but I felt myself wanting a spanking too. I said “I’m not taking off my jeans for you”. He said “ah ha” like he had figured something out. “I guess that’s your weakness. You can take pain but not embarrassment. You are physically tough but not emotionally tough”. His analysis cut deep into my soul. I didn’t like being told I had a weakness. I said “No, that’s not it. I just don’t want my pervy little step brother looking at my undies”. He shrugged and said “whatever excuse you need to tell yourself to avoid admitting it”. I could feel he won even before I said “fine! Game On! I can handle anything pain or embarrassment”. With that I stood up and undid my belt and jeans. Then I slid them down to my knees revealing my yellow cotton bikini cut panties with a little duckie embroidered on the hip. I felt him trying to look through the thin material. I guess what 13 year old boy wouldn’t do that with a 17 year old girl in front of him in her undies. I quickly got over his knees to at least keep him from looking at my front.
Of course this left my bottom somewhat on display and I was thankful I hadn’t worn a thong. J
This new and unorthodox relationship with my step brother was on my mind a lot. It was hard for me to sort out my thoughts and feelings. One night after not being able to get to sleep, I found Tony in his office. I said “hi. Got time to talk?”. He said “sure honey. What’s bothering you?” I thought for a few moments then formulated my dilemma. I said “well, I let Jack spank me again last week. This time with my jeans down. I feel…..conflicted”. Tony nodded. He said “well let’s start by bringing me up to speed.”, so I told him how it somewhat innocently started. Then he asked “are you a virgin?”. I said “no” and briefly told him about my boyfriend I had for a short time early last year. He said “ok. I suspected as much. It’s not uncommon for girls your age. So a boy has seen you undressed before. So what’s the big deal that Jack saw your underwear?”. I said “well….he’s my little brother…..sort of”. Tony said “I see. But it didn’t stop you did it?”. I shook my head a little ashamed. He asked “did you masturbate after your spankings? You did didn’t you?” I nodded and blushed brightly. He said “Heather, I’m not expert, but from what I can tell it seems you get some enjoyment out of the pain. A lot of girls are like that. Some even get a thrill out of being extremely embarrassed. It’s called humiliation. I think you are one of the rare girls that likes both. What do you think?” I pondered a moment before saying “yeah, I think you might be right. I don’t know though. But isn’t it wrong because he’s….” Tony interupts saying “he’s your step brother, so biologically it’s not really wrong. It just feels that way which might be what adds to your embarrassment. I think the fact that he’s 13 and you’re 17 adds to your embarrassment too. For instance, if it was me bossing you around, we’ll that’s my job. Your younger step brother had no natural business ordering you to do anything”. I have Tony a half smile and said “yeah. You’re right”. He said “I imagine Jack is motivated by feelings that dovetail yours. You are both young, it’s a good time to experiment with these feelings.” I was surprised and asked “so you are….ok….with it?”. He said “yes, but with some conditions. You have to make sure to stop if you are uncomfortable with any situation, don’t let it get out of hand where you would need stiches or a cast or something permanent. And you don’t have to sneak around. I know what’s going on. I don’t need to be involved, but we should talk about this as a family occasionally just to make sure it doesn’t get out of hand. I’ll give Jack the same talk, but I’ll mostly leave things up to you and Jack to work out”. I have Tony a hug and said “Thanks for the talk. I feel better”.
A week later Jack says when we get home from school “Heather, I think today would be a great day for a bare bottom spanking don’t you?”. I said “I’m not taking my panties off for you.” He said “I thought you could handle embarrassment. You’re not as tough as I thought”. I knew he was goading me into this, but like most little brothers, he had a skill for pushing my buttons. I said “I’m not ready to take my bottoms off. You can still spank me though”. He said “I really prefer it if you are embarrassed. Your face cheeks get as red as your bottom cheeks, and I think it’s funny”. I shook my head “No, you are my little step brother. I’m not going bottomless in front of you” I said. He rubbed his chin in thought, then said “Ok. If your underpants are so important to you, leave them on…….but take everything else off instead”. My eyes looked surprised and I said “but Jack”. He interrupted saying “come on Heather. Dad told me part of the fun for you was letting a younger boy be your boss. I think I’m being pretty generous letting you keep your panties on. Don’t you?”. He added “if you aren’t going to listen to me, it’s not any fun”. I thought quietly for a minute then said “You’re right Jack. Ok fine, I’ll take off everything except my underpants”. He smiled, knowing he won.
I slowly began to undress. My tee shirt slid over my head first, then I unbuckled my jeans and slid them down my legs. I had on pink and orange horizontal striped panties on and a plain white cotton bra. It was almost equivalent to wearing a bathing suit so I wasn’t too embarrassed yet. He said “what is your bra size Heather?”. I mumbled “34B”. I turned my back and undid my bra. It slid off my arms onto the floor. I turned back with my arms covering my breasts.
Source: reddit.com/r/sexystories/comments/8ecl7r/heather_and_jack_part_1_mf
looks interesting. Good writing – happy to read more!
I too would like to read more!