My Boyfriend's Sister (Complete)
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My Boyfriend's Sister (Complete)
A/N: This is a sequel to The Smash Bet. This story is a little darker than The Smash Bet with themes of domination and punishment, but it still follows the ideals of the first story, where Jennifer is a reluctant but willing victim to the various humiliating scenarios she finds herself in.
Edit: I have made a few edits to this story just to make it clear that this story is consensual. Cheers.
Part 1
I’ve been texting back and forth with Josh for about a week now. Crazy as it sounds, I’m kind of enamored with him. He revealed to me desires that I didn’t know I had. It was a sexual awakening. I wanted to see him again. Unfortunately, as much as I want to spend my Friday night with him, he’s on a flight to Los Angeles interviewing for jobs. Which I have mixed feelings about to be honest. I’m happy for him advancing his career and moving up in the world, but also kind of worried that my new boyfriend is about to move away before I even get a chance to really get to know him. But he reassured me that he’s not going to let me off the hook until he’s satisfied that I’ve truly learned my lesson. I smile. I look forward to his lessons.
I’m getting ready for some me time. Friday night is my day off. It’s a busy night in the restaurant industry, but ever since my college years, it’s been off limits to all things work, and I’ve never compromised on that. I’m thinking warm bath, candles and wine, a bath bomb, the whole shebang. Of course, I’d much rather be spending the night with Josh, but this is the next best thing.
As I’m getting ready to strip off my clothes and start my steamy bath, I hear my phone vibrate. I stop what I’m doing and make my way over to my messy, unmade bed. My heart skips a beat, hoping it’s Josh. I dive onto my soft mattress with a bounce and unlock my phone. Unknown number. Not Josh. Bummer.
I receive a cryptic message. It contained Josh’s address and instructions to come over tonight. “Wear nothing but the dress. You know the one.”
Is Josh playing some kind of prank on me? But it doesn’t really make sense. He’s out of town, so why would he want to come over? I write back: “Who is this?”
“I know what you did last Friday.”
The phone rings. I answer, ready to put an end to whatever game Josh was playing. “Josh, if this is your idea of a prank, it isn’t funny. Not cool.”
I’m surprised when it’s not Josh on the line, but a cool, feminine, wispy voice. “You have an hour. Don’t be late.” Click. Well, I guess I’m going to Josh’s house. While she didn’t say what she plans to do if I don’t come over, I don’t particularly want to find out. I’m not really enthusiastic that someone besides my boyfriend knows what happened the other night or what they might do with that information, but I wouldn’t say I’m all that concerned, either. It’s not like I’ve done anything particularly wrong. And I’m not even sure how much she really knows. But admittedly, I am curious. I don’t have a lot of time. I’m more irritated than anything. Bath canceled. Time to get changed.
I take off my t-shirt and yoga pants and stare at my reflection in the tall mirror. My red sports bra and matching hipster panties would definitely clash with a black dress, I think. In a moment of vanity, I admire my athletic body in the mirror. Even in my casual underwear, I know I’m a bombshell. I take a lot of pride in my appearance. What can I say? Although in the back of mind, I’m thinking, you have more important things to think about than how good you look in the mirror, dumbass. This woman could be trouble. What if she knows about the car? Somehow, I don’t think that Josh’s ‘permission’ will count for much. What does she want from me, I wonder.
Nevertheless, there’s no excuse to look tacky. I decide to put on a VS angel black push-up bra and matching thong panties, and a cute pair of black platform wedge heels to complete the look. Damn, I look good, I think. Next step: makeup. For once, I don’t fuck it up, and I draw a perfect cat eye. Well, almost perfect. I like to say my eyes are sisters, not twins. I’m in a hurry and don’t have time to do it twice. I pat on some light liquid foundation with my sponge, add some blush, a touch of highlight here and there, red lipstick, and I’m ready to go. Not the best face I’ve ever done, but this mystery woman isn’t exactly giving me a lot of time.
I’m sure some people would wonder why I would bother with all this eye make-up and contouring for a stranger that seems to be blackmailing me. I only wore foundation for my date with Josh. Honestly? It’s vanity. Josh wouldn’t know good make-up if it hit him in the face with a blender. It would be a Christmas miracle if he managed to look up from my bust line long enough to notice my eyeliner. But she’ll notice.
With great reluctance, I put on the casual, strappy black dress that Josh let me borrow last week. I’m not a huge fan of being told what to wear. This isn’t even mine. But, again, not really looking to test the waters here. I just want to get this over with and see what this bitch wants from me. Best case scenario, she wants an apology, and we move on. Worst case, she wants money. Either way, I’m optimistic that the situation isn’t that bad.
I’m not Nancy Drew, but I’m also not stupid. I have a pretty good idea about her identity. I’m guessing this is my boyfriend’s sister. And if that’s the case, what’s the worst that could happen? I’m sure once I explain to her that me and Josh are dating, it will clear up that this is all a big misunderstanding. We might even become friends. I’m a real glass half-full kind of girl.
I look at myself in the mirror one last time. The thin fabric of the dress hugs my curves in a flattering way, and the neckline gives a hint of my bosom. It’s not exactly a perfect fit. It was made for someone taller, but I pull it off reasonably well. I take it all in. I look good. I’m wearing my hair curly today. It’s what I like to call long-short. I look like I’m going to a fancy party instead of being about to meet my boyfriend’s sister.
Edit: I have made a few edits to this story just to make it clear that this story is consensual. Cheers.
Part 1
I’ve been texting back and forth with Josh for about a week now. Crazy as it sounds, I’m kind of enamored with him. He revealed to me desires that I didn’t know I had. It was a sexual awakening. I wanted to see him again. Unfortunately, as much as I want to spend my Friday night with him, he’s on a flight to Los Angeles interviewing for jobs. Which I have mixed feelings about to be honest. I’m happy for him advancing his career and moving up in the world, but also kind of worried that my new boyfriend is about to move away before I even get a chance to really get to know him. But he reassured me that he’s not going to let me off the hook until he’s satisfied that I’ve truly learned my lesson. I smile. I look forward to his lessons.
I’m getting ready for some me time. Friday night is my day off. It’s a busy night in the restaurant industry, but ever since my college years, it’s been off limits to all things work, and I’ve never compromised on that. I’m thinking warm bath, candles and wine, a bath bomb, the whole shebang. Of course, I’d much rather be spending the night with Josh, but this is the next best thing.
As I’m getting ready to strip off my clothes and start my steamy bath, I hear my phone vibrate. I stop what I’m doing and make my way over to my messy, unmade bed. My heart skips a beat, hoping it’s Josh. I dive onto my soft mattress with a bounce and unlock my phone. Unknown number. Not Josh. Bummer.
I receive a cryptic message. It contained Josh’s address and instructions to come over tonight. “Wear nothing but the dress. You know the one.”
Is Josh playing some kind of prank on me? But it doesn’t really make sense. He’s out of town, so why would he want to come over? I write back: “Who is this?”
“I know what you did last Friday.”
The phone rings. I answer, ready to put an end to whatever game Josh was playing. “Josh, if this is your idea of a prank, it isn’t funny. Not cool.”
I’m surprised when it’s not Josh on the line, but a cool, feminine, wispy voice. “You have an hour. Don’t be late.” Click. Well, I guess I’m going to Josh’s house. While she didn’t say what she plans to do if I don’t come over, I don’t particularly want to find out. I’m not really enthusiastic that someone besides my boyfriend knows what happened the other night or what they might do with that information, but I wouldn’t say I’m all that concerned, either. It’s not like I’ve done anything particularly wrong. And I’m not even sure how much she really knows. But admittedly, I am curious. I don’t have a lot of time. I’m more irritated than anything. Bath canceled. Time to get changed.
I take off my t-shirt and yoga pants and stare at my reflection in the tall mirror. My red sports bra and matching hipster panties would definitely clash with a black dress, I think. In a moment of vanity, I admire my athletic body in the mirror. Even in my casual underwear, I know I’m a bombshell. I take a lot of pride in my appearance. What can I say? Although in the back of mind, I’m thinking, you have more important things to think about than how good you look in the mirror, dumbass. This woman could be trouble. What if she knows about the car? Somehow, I don’t think that Josh’s ‘permission’ will count for much. What does she want from me, I wonder.
Nevertheless, there’s no excuse to look tacky. I decide to put on a VS angel black push-up bra and matching thong panties, and a cute pair of black platform wedge heels to complete the look. Damn, I look good, I think. Next step: makeup. For once, I don’t fuck it up, and I draw a perfect cat eye. Well, almost perfect. I like to say my eyes are sisters, not twins. I’m in a hurry and don’t have time to do it twice. I pat on some light liquid foundation with my sponge, add some blush, a touch of highlight here and there, red lipstick, and I’m ready to go. Not the best face I’ve ever done, but this mystery woman isn’t exactly giving me a lot of time.
I’m sure some people would wonder why I would bother with all this eye make-up and contouring for a stranger that seems to be blackmailing me. I only wore foundation for my date with Josh. Honestly? It’s vanity. Josh wouldn’t know good make-up if it hit him in the face with a blender. It would be a Christmas miracle if he managed to look up from my bust line long enough to notice my eyeliner. But she’ll notice.
With great reluctance, I put on the casual, strappy black dress that Josh let me borrow last week. I’m not a huge fan of being told what to wear. This isn’t even mine. But, again, not really looking to test the waters here. I just want to get this over with and see what this bitch wants from me. Best case scenario, she wants an apology, and we move on. Worst case, she wants money. Either way, I’m optimistic that the situation isn’t that bad.
I’m not Nancy Drew, but I’m also not stupid. I have a pretty good idea about her identity. I’m guessing this is my boyfriend’s sister. And if that’s the case, what’s the worst that could happen? I’m sure once I explain to her that me and Josh are dating, it will clear up that this is all a big misunderstanding. We might even become friends. I’m a real glass half-full kind of girl.
I look at myself in the mirror one last time. The thin fabric of the dress hugs my curves in a flattering way, and the neckline gives a hint of my bosom. It’s not exactly a perfect fit. It was made for someone taller, but I pull it off reasonably well. I take it all in. I look good. I’m wearing my hair curly today. It’s what I like to call long-short. I look like I’m going to a fancy party instead of being about to meet my boyfriend’s sister.
Last edited by MissAriel on Fri Dec 09, 2022 7:29 pm, edited 4 times in total.
See my collection of stories here: MissAriel's Story Archive
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Re: My Boyfriend's Sister
Part 2
When she opens the door, I’m admittedly taken aback. The first thought that comes to mind is there hasn’t been a moment in this woman’s life where she wasn’t the most attractive person in the room. She’s tall, thin, modelesque. She has a beautiful heart-shaped face and long, straightened black hair. Her makeup is stunning and her skills far exceed my own. She’s even more feminine than I am, which is not something that I encounter often. “I’m Rachel. I’ve been expecting you. Come in,” she says in her wispy, siren-like voice. No hello, just, I’ve been expected. I oblige her request. There’s something about her that’s captivating, enthralling even, yet her commanding presence unnerves me.
She takes a seat on the couch and it brings back certain recent memories that I have no interest in repeating at this particular moment. She gives me a look as if to say, hurry up and take a seat, and so I do. I take a moment to take in her outfit, which consists of a long flowing waist-high black skirt and matching crop top. It contrasts with her pale complexion, almost giving a goth-like appearance.
“What do you want?” I cut straight to the point. I’m irritated that she’s interrupted my me time. I could be having a bath right now, I think, but instead, I’m here, talking to my boyfriend’s sister for who knows what reason. What does she want?
“We’ll get to that. You had quite the night with my little brother.” Rachel’s eyes pierce me and it feels as if she can read me completely, as if I could hide nothing from her.
“How do you know about that? Did Josh tell you? I can’t believe he’d do that. That was private.”
She lets out a chuckle. Not a laugh, but a tiny display of amusement. Everything about her is subtle. While Josh had a certain grandiosity about him, Rachel moved and spoke exactly as she meant to; with precision, grace, intent.
“No, my brother and I do not generally share the details of our conquests.” Conquest, was that what I was? I’m flushed, thinking that yes, actually, that is a perfect description of what happened to me. “Like a natural disaster, you leave incontrovertible evidence in your wake. Did it occur to your cute little blonde head that an affluent family like ourselves has security?”
“Um, what... what kind of security?” I’m blindsided. Cameras? Does she have me on tape? What’s her angle?
“When I noticed my dress was missing,” she points at my dress with disdain, “I naturally investigated to find out what kind of delinquent has been rummaging through my things. How surprised I was to find a little tart taking my father’s car for a joyride.”
Well, fuck. She’d seen me taking the car, and not just that, but she’s seen... everything. I’m crimson with shame. Yet another person has seen me naked. When will it end? I have to assume the worst. “Are you blackmailing me?”
She rolls her eyes and her contempt is palpable. “Hardly. You can relax your pretty little head,” Rachel says, patting me on the head like a troublemaker child. “The evidence of your impropriety has passed.”
“Oh,” I say, surprised. “Um, thank you?”
“However, there is still the matter of my dress. I want it back. Now.” She holds out her hand. Rachel’s siren-like voice is commanding and powerful. I don’t know why, but a small part of me wants to obey her. But a much bigger part of me is saying, hell no, not again. I’m so over this psychopath family. Are they all like this? This is ridiculous.
“A world of nope. I’m going home. You can have your stupid dress back later. I’ll give it back to Josh the next time I see him. It was nice meeting you, bye.” I’m out of here. I’m so done with this. Josh’s sister is crazy if she thinks I’m just going to take off my dress right here. I stand up and begin walking towards the door. This is my Friday night. I’m going to go home and have a nice bath and forget all about this.
“You’ll do no such thing. Take off my dress or I’ll do it for you.” I freeze. I have no idea why, but I just can’t seem to move in this particular moment. Fight or flight? No thanks, I’ll just stand here like a deer in headlights. I urge my body to just leave, but I feel paralyzed. She just has this... effect on me. There is a part of me that wants to leave, but also a part of me that wants to obey her.
I hear the clicking of her heels as she approaches me and lifts my arms and swoops the dress right off of me, leaving me standing in front of the window in my bra and thong. Once again, in this house, I am humiliated.
“I told you to wear nothing else. Was I not clear?” She chastises me and I can feel her fingers nimbly unsnap my bra and my garment is taken away from me. I stand here in front of the window wearing only a black thong and platform heels. My breasts are on display to any neighbors that happen to pass by. Every fiber of my being is telling me to move out of view of the fucking window, to at least cover my tits for God's sake, but my body is frozen in place. This is mortifying. How the fuck did I end up in this situation again? Fuck. My. Life.
“Come,” Rachel commands. She takes my arm and walks me back to the couch. I have a distinct feeling of deja vu as she bends me over her lap, my tiny nipples once again brushing against the cool texture of leather. I feel my panties violently pulled down and I can see Rachel sliding them around my heels as I turn my head back to look at her. She tosses them away and I’m seeing red. Who does she think she is? Doing this to me of all people? But my mind scathingly replies, you’re her bitch, Jennifer. You didn’t even try to stop her. But I did try! I just... couldn’t. I... don't want her to stop.
I feel a harsh slap on my ass and it burns like fire. “This is for stealing my dress, you little tart.” Slap. I yelp. Unlike Josh, there’s no playfulness, no expectation of a thank you, there is only the raw pain and humiliation of being spanked like a little girl. Rachel is all business. “This is for not obeying my instructions.” Slap. Oh, God, it stings. It feels personal, despite the fact that I’ve never even met this sadistic socialite.
“Stop!” I cry out. “I didn’t steal it. Josh let me borrow it. I was going to give it back, I swear!” I bargain and plead. Surely, she’d understand this was all a big misunderstanding, right?
Her hand slaps my firm little ass once more with force. What did I do to deserve this? “No talking.” Slap. It stings so bad. I silently wished it was Josh spanking me instead. She’s so much more... harsh. “This is for stuffing my dildo in your little snatch.” Slap, slap. At least with Josh, there was a counter. I knew when it would stop. But with her, I didn’t know anything. Why was I letting her do this to me? I keep asking myself, why didn’t I just leave? In a moment of pause where I can actually think about something other than the fact that I’m getting spanked by Rachel, I realize that Josh must have tied me up in Rachel’s room. It explained a lot of things. The dildo, the fabric scissors, the perfectly made bed and pristinely clean room... there’s no way that room belongs to a guy. What a jerk! I can’t believe he did that. If I was her, I’d be incensed. A girl’s room is sacred. But she should be angry with Josh, not me. Why is she taking it out on me?
“Rachel, please, stop. I didn’t know that was your room. It was all his idea. You have to believe me.”
“Do your ears not work? I said no talking.” Slap. My ass burns with the fire of a thousand suns. I shut my mouth and pledge to not speak again. Every time I talk, it just makes things worse for me. It finally ends. Rachel stops spanking me and brings me up to a seated position. She pats me on the head again. “You can relax, dear. You’re okay now.” She gives me a warm hug and I feel... confused? Is she... comforting me? I can’t figure out if she hates me or likes me.
Still frozen in time, I allow her to take off my platform shoes. She stands me up and the difference in our height is now stark. She towers over me like I’m just a teenager and I feel small and insignificant. I am usually confident, strong-willed. I know how beautiful I am. But next to her, I feel envy of her. She’s so tall, her figure fuller, her waist tinier. I’m straight. I’ve never shown any interest in women. But at this moment, I’m not sure if I want to be her or to be on her. I don’t have time to figure it out. “Come.” She takes my arm. Click, click, click, her feminine heels sound as we walk towards her bedroom. I remember back to the last time I was here, tied spread eagle to the bed and forced to endure an hour of tickling.
No, no, no, I think, not again. Fuck this. I’m out of here. I’m leaving! And yet I continue following Rachel, not daring to disobey her.
When she opens the door, I’m admittedly taken aback. The first thought that comes to mind is there hasn’t been a moment in this woman’s life where she wasn’t the most attractive person in the room. She’s tall, thin, modelesque. She has a beautiful heart-shaped face and long, straightened black hair. Her makeup is stunning and her skills far exceed my own. She’s even more feminine than I am, which is not something that I encounter often. “I’m Rachel. I’ve been expecting you. Come in,” she says in her wispy, siren-like voice. No hello, just, I’ve been expected. I oblige her request. There’s something about her that’s captivating, enthralling even, yet her commanding presence unnerves me.
She takes a seat on the couch and it brings back certain recent memories that I have no interest in repeating at this particular moment. She gives me a look as if to say, hurry up and take a seat, and so I do. I take a moment to take in her outfit, which consists of a long flowing waist-high black skirt and matching crop top. It contrasts with her pale complexion, almost giving a goth-like appearance.
“What do you want?” I cut straight to the point. I’m irritated that she’s interrupted my me time. I could be having a bath right now, I think, but instead, I’m here, talking to my boyfriend’s sister for who knows what reason. What does she want?
“We’ll get to that. You had quite the night with my little brother.” Rachel’s eyes pierce me and it feels as if she can read me completely, as if I could hide nothing from her.
“How do you know about that? Did Josh tell you? I can’t believe he’d do that. That was private.”
She lets out a chuckle. Not a laugh, but a tiny display of amusement. Everything about her is subtle. While Josh had a certain grandiosity about him, Rachel moved and spoke exactly as she meant to; with precision, grace, intent.
“No, my brother and I do not generally share the details of our conquests.” Conquest, was that what I was? I’m flushed, thinking that yes, actually, that is a perfect description of what happened to me. “Like a natural disaster, you leave incontrovertible evidence in your wake. Did it occur to your cute little blonde head that an affluent family like ourselves has security?”
“Um, what... what kind of security?” I’m blindsided. Cameras? Does she have me on tape? What’s her angle?
“When I noticed my dress was missing,” she points at my dress with disdain, “I naturally investigated to find out what kind of delinquent has been rummaging through my things. How surprised I was to find a little tart taking my father’s car for a joyride.”
Well, fuck. She’d seen me taking the car, and not just that, but she’s seen... everything. I’m crimson with shame. Yet another person has seen me naked. When will it end? I have to assume the worst. “Are you blackmailing me?”
She rolls her eyes and her contempt is palpable. “Hardly. You can relax your pretty little head,” Rachel says, patting me on the head like a troublemaker child. “The evidence of your impropriety has passed.”
“Oh,” I say, surprised. “Um, thank you?”
“However, there is still the matter of my dress. I want it back. Now.” She holds out her hand. Rachel’s siren-like voice is commanding and powerful. I don’t know why, but a small part of me wants to obey her. But a much bigger part of me is saying, hell no, not again. I’m so over this psychopath family. Are they all like this? This is ridiculous.
“A world of nope. I’m going home. You can have your stupid dress back later. I’ll give it back to Josh the next time I see him. It was nice meeting you, bye.” I’m out of here. I’m so done with this. Josh’s sister is crazy if she thinks I’m just going to take off my dress right here. I stand up and begin walking towards the door. This is my Friday night. I’m going to go home and have a nice bath and forget all about this.
“You’ll do no such thing. Take off my dress or I’ll do it for you.” I freeze. I have no idea why, but I just can’t seem to move in this particular moment. Fight or flight? No thanks, I’ll just stand here like a deer in headlights. I urge my body to just leave, but I feel paralyzed. She just has this... effect on me. There is a part of me that wants to leave, but also a part of me that wants to obey her.
I hear the clicking of her heels as she approaches me and lifts my arms and swoops the dress right off of me, leaving me standing in front of the window in my bra and thong. Once again, in this house, I am humiliated.
“I told you to wear nothing else. Was I not clear?” She chastises me and I can feel her fingers nimbly unsnap my bra and my garment is taken away from me. I stand here in front of the window wearing only a black thong and platform heels. My breasts are on display to any neighbors that happen to pass by. Every fiber of my being is telling me to move out of view of the fucking window, to at least cover my tits for God's sake, but my body is frozen in place. This is mortifying. How the fuck did I end up in this situation again? Fuck. My. Life.
“Come,” Rachel commands. She takes my arm and walks me back to the couch. I have a distinct feeling of deja vu as she bends me over her lap, my tiny nipples once again brushing against the cool texture of leather. I feel my panties violently pulled down and I can see Rachel sliding them around my heels as I turn my head back to look at her. She tosses them away and I’m seeing red. Who does she think she is? Doing this to me of all people? But my mind scathingly replies, you’re her bitch, Jennifer. You didn’t even try to stop her. But I did try! I just... couldn’t. I... don't want her to stop.
I feel a harsh slap on my ass and it burns like fire. “This is for stealing my dress, you little tart.” Slap. I yelp. Unlike Josh, there’s no playfulness, no expectation of a thank you, there is only the raw pain and humiliation of being spanked like a little girl. Rachel is all business. “This is for not obeying my instructions.” Slap. Oh, God, it stings. It feels personal, despite the fact that I’ve never even met this sadistic socialite.
“Stop!” I cry out. “I didn’t steal it. Josh let me borrow it. I was going to give it back, I swear!” I bargain and plead. Surely, she’d understand this was all a big misunderstanding, right?
Her hand slaps my firm little ass once more with force. What did I do to deserve this? “No talking.” Slap. It stings so bad. I silently wished it was Josh spanking me instead. She’s so much more... harsh. “This is for stuffing my dildo in your little snatch.” Slap, slap. At least with Josh, there was a counter. I knew when it would stop. But with her, I didn’t know anything. Why was I letting her do this to me? I keep asking myself, why didn’t I just leave? In a moment of pause where I can actually think about something other than the fact that I’m getting spanked by Rachel, I realize that Josh must have tied me up in Rachel’s room. It explained a lot of things. The dildo, the fabric scissors, the perfectly made bed and pristinely clean room... there’s no way that room belongs to a guy. What a jerk! I can’t believe he did that. If I was her, I’d be incensed. A girl’s room is sacred. But she should be angry with Josh, not me. Why is she taking it out on me?
“Rachel, please, stop. I didn’t know that was your room. It was all his idea. You have to believe me.”
“Do your ears not work? I said no talking.” Slap. My ass burns with the fire of a thousand suns. I shut my mouth and pledge to not speak again. Every time I talk, it just makes things worse for me. It finally ends. Rachel stops spanking me and brings me up to a seated position. She pats me on the head again. “You can relax, dear. You’re okay now.” She gives me a warm hug and I feel... confused? Is she... comforting me? I can’t figure out if she hates me or likes me.
Still frozen in time, I allow her to take off my platform shoes. She stands me up and the difference in our height is now stark. She towers over me like I’m just a teenager and I feel small and insignificant. I am usually confident, strong-willed. I know how beautiful I am. But next to her, I feel envy of her. She’s so tall, her figure fuller, her waist tinier. I’m straight. I’ve never shown any interest in women. But at this moment, I’m not sure if I want to be her or to be on her. I don’t have time to figure it out. “Come.” She takes my arm. Click, click, click, her feminine heels sound as we walk towards her bedroom. I remember back to the last time I was here, tied spread eagle to the bed and forced to endure an hour of tickling.
No, no, no, I think, not again. Fuck this. I’m out of here. I’m leaving! And yet I continue following Rachel, not daring to disobey her.
Last edited by MissAriel on Fri Dec 09, 2022 7:30 pm, edited 4 times in total.
See my collection of stories here: MissAriel's Story Archive
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Re: My Boyfriend's Sister
Part 3
The bedroom is exactly as I remember it down to the last detail. Vivid memories of that awful torture session flood my mind and I resolve to not let it happen again. I am not, under any circumstances, going to let myself get tied up again. You really think so? I reply to myself.
“Stay,” Rachel commands and I obey without question. There is literally nothing stopping me from just walking the hell out of here, I think, but my legs feel stiff as boards and they don’t move an inch. Am I really going to just let this happen again? I’m confident and strong, I think. I don’t have to stand for this! When she comes back, I’m going to give her a piece of my mind.
When she returns, she’s holding a bottle of oil and a cotton ball. Oh, hell no, I think, not in a million years. If you think I’m just going to let you oil me up like one of those sluts on Pornhub, you’ve got another thing coming. I shake my head. “Listen you crazy bitch, I don’t know what kind of sex games you’re fantasizing about with that bottle of oil, but I want no part of it. I’m going home,” I say defiantly. I feel my resolve return. I’m confident and beautiful and I don’t have to do anything that this crazy bitch says if I don’t want to.
But Rachel doesn’t react the way I expect. Instead of seeing anger or surprise, she just looks disappointed. She shakes her head.
“So much talking with you. Hush, little girl.” She holds my chin with her delicate hands and peers into my soul. She makes me feel naked in a way that has nothing to do with my state of dress. I feel wetness touching my skin. She’s wiping down my face. The oil isn’t for my skin... it’s to remove my make-up. I don’t even motion to stop her, starstruck by her audacity. She has left me truly, completely, utterly naked. The contrast between myself and her now grows ever starker. I’m plain, ordinary, average, standing in submission to this goddess of a woman. My fiery spirit and resistance melts away. My desire to defy her fades away as I experience the ecstasy of her domination.
She gently pushes me onto the bed and I feel myself bounce onto the softness of the mattress. Once again, I feel paralyzed, unable to move or speak, just letting her do whatever she wants with me. I see her tying my arms and legs to the bedposts, and all I can think is, please, not again. Yet I make no motion to stop her and my actions betray my thoughts. A shameful part of me enjoys being completely powerless and I feel conflict within myself. I could ask her to stop, could I not? And the rational part of my brain says that I should. Yet I lie here embracing my bondage.
After Rachel finishes binding my limbs and I’m unable to move, she takes a seat on the bed and strokes my hair. “Good girl,” she says, and I flush, feeling a mixture of anger and pleasure. When she calls me a good girl, it makes me... happy? But how dare she. Does she have any idea who I am?
In an unexpected twist, Rachel shoves my phone in my face and says, “Passcode. Now.”
No, no, no, I’m not giving you my fucking passcode, you crazy bitch. That’s my private phone. Not. Fucking. Happening. “No,” I squeak defiantly, but it comes out sounding more like a question than a rebuke. Rachel lightly twists my nipple and I squeal, “3343! The passcode is 3343!” Have I really let her break me so easily? A part of me just wants to surrender myself to her. I’ve never met someone who is so persuasive while saying so little. The way she talks is so terse, so to the point, without the flatteries and fluff of normal speech. Whenever her siren-like voice speaks, it captures my full attention, as if listening to her is the most important thing I could possibly be doing at this particular moment.
She leans down and holds the phone in such a way that we can look at it together. “Let’s see what sort of person you are, Jennifer.” I shiver. This is the first time she’s called me by my name, and it suddenly occurs to me that I’m not sure how she even got my phone number. But I suppose that’s a mystery to solve at another time, because right now she is going through my personal photos.
“Vain, aren’t you?” I stare in silence. I can’t believe she’s going through my personal photos. It’s such a violation of my personal space, as if she’s going through my underwear drawer, but I can do nothing to stop her. I practically volunteered my passcode. “You have so many selfies. Such narcissistic tendencies. What does little brother see in you, I wonder.” I say nothing, hanging my head in shame. How do I manage to keep putting myself into these situations? I should have just ignored her and stayed home, I think. That would have been the better decision.
I watch in horror as she clicks on the folder that labeled ‘hidden’. Passcode required. 3343, she enters. I’m forced to look at my own nudes. I mean, seriously, don’t judge me, who doesn’t have photos like these on their phones? Rachel stops on a photo that I’m rather fond of. I took it in front of my tall mirror. I see my athletic, toned body, my perky breasts and shapely legs, tiny hints of lines that define my abs, a familiar smirk that says, I have it. My pose is effortless, confident. Rachel smiles. “I like this confidence.” She pauses and I can feel her devilish energy. “I will enjoy taking it from you.”
No, no, no. You’ve got to be kidding me, I think. I’ve been stripped, spanked, had my bare face exposed, tied up, and forced to watch in silence as this evil succubus goes through my most private photos. This is so unfair. What is with this psycho family’s obsession with torture? Sigh. At least it can’t get much worse than this, right?
She holds my chin with in her soft, delicate hands once more. “Everything you did in my room. Now.”
I pause for a moment, considering my options, but I’ve been here long enough to know what’s going to happen. I’ll put on a show of defiance and then she’ll pop me like a cherry until I squeal. I decide to just save myself the embarrassment and give her an abbreviated version. “Josh tied me up and we had sex. It was his idea. I swear. Please, I’m sorry, I didn’t know it was your room. I would never do something like that on purpose.”
She peers at me. “Is that everything?”
“Yes,” I reply, not really wanting to go into exquisite detail of Josh’s tickle torture, the way he sliced up my clothes with the fabric scissors, or how he had me pleading for sex.
Rachel walks to her chest of drawers and pulls out a kind of chain with some attachments at the end. It looks like some kind of modern torture device and I really don’t want to find out what it does. “Liar.” She sees right through me. My body language is completely transparent and I can’t hide anything from her. I can feel cold metal clamping down on my incredibly sensitive nipples and I grit my teeth. I fight against my bonds, but my limbs are completely immobile. “The truth. Now.”
I break almost immediately. I tell her everything. About the bet, the tickling, the spanking, the sex. I even tell her about being pulled over for speeding and my humiliation at the gas station. I tell her every detail until she’s completely satisfied. I submit myself completely to her. All my bravado and spunk has faded away and I sink into complete obedience. I want nothing more than to fulfill her every command. If she told me to say I’m a dirty lesbian slut, I would say I’m a dirty lesbian slut, thank you, my sexuality be damned.
“Good girl,” Rachel says, stroking my hair and patting my head. She caresses my chest with a feminine grace and gentleness that no man could replicate. “I forgive your transgression.” I have her forgiveness and it fills me with joy. It should seethe me with anger, but such emotions have long since faded away. I surrendered myself. She whispers into my ear, “See that it doesn’t happen again.”
“I promise to never touch your things again, Rachel,” I reply obediently, wishing nothing more than for her approval.
She slaps my face for the first time tonight and it stings. “Miss Rachel!” I squeak.
“If you ever do,” she replies, leaning in again to whisper in my ear, her siren-like voice serenading me with primal fear, “I’ll put you on display like a Christmas tree. The world will know your conceit.” My imagination runs wild. I can see myself tied naked to a tree in the middle of the quad, my tight athletic body freely gazed upon by thousands of students on their way to the first class of the day. The guys whistling and hooting, the girls snickering at my misfortune. It would be a fate worse than death. I silently make a vow to never touch her things again. I didn’t even do it on purpose in the first place. It wasn’t even my fault. It was all Josh’s idea. But I know better than to talk back.
“I promise, Miss Rachel,” I plead, hoping for her tender side, wishing for her to pat me on the head and tell me I’m a good little girl. I find myself perplexed at my behavior. I’ve been completely dominated in a way that not even Josh managed to do. All of my spunk, my bravado, my confidence, it might as well be a distant memory.
“Tell me what you want, girl.” She holds my chin with her delicate fingers and I’m forced to look into her eyes. I must not tell lies, I think. But this is my chance to go home. For the first time tonight, she’s asking me what I want.
“I, um, I want to go home,” I reply. “Miss Rachel,” I add quickly, careful to show her the respect she commands.
She shakes her head and I can feel her disappointment again. “I would grant your wish. If you were being honest.” She sees right through me. She can always tell. My eyes give everything away. I can hide nothing from her. It's true. I am a liar. I want this. “The truth.” She twists the nipple clamps and I once again find myself broken.
“Miss Rachel, please tickle torture me until I beg you to fuck me like the little lesbian slut that I am!” I squeak.
Fuck. I. Cannot. Believe. I. Said. That.
“Where are you ticklish?” she says. Her voice is now light and sing-songy. I’ve made her happy. Miss Rachel is pleased.
“Underneath my leg,” I say. I don’t even consider lying. It’s pointless. She can see through my deception as clearly as the morning light. What have I done? I can’t believe I just asked her to tickle me. I fucking hate being tickled. I’ve hit rock bottom. It doesn’t get any worse than this. I’m not even attracted to women, yet here I am, begging this beautiful woman to tickle me and then fuck my brains out. Straight, are you? I think to myself. Well, a noodle is straight until it’s wet.
Her fingers curl and graze my most sensitive area and I explode into laughter. Ha, ha, ha, fuck, why did I, ha, ha, ask for this? I can’t think at all as I involuntarily thrash against my bonds and cackle uncontrollably. I feel the nipple clamps bounce uncomfortably as I squirm, my sensitive areola pulsing, and my pussy ignites with pleasure. I unconsciously look at the dresser to check how much time is left and find myself remembering that there is no timer. This ends when Miss Rachel says it ends.
I’m not sure how much time has passed, but it does not take Miss Rachel long to break me. I hear myself begging. “Miss Rachel, ha, ha, please, anything but tickling, ha, ha. I can’t take it! Please!” I laugh, bellow, cackle, squeal. I have no dignity left. I am her toy to use as she wishes. Miss Rachel looks pleased. “Please fuck me, Miss Rachel. I need it! No more, ha, ha, tickling!”
“Good girl,” Rachel says, her harmonious voice’s approval bringing me glee. She pats me on the head and steps back. She strips off her black crop top and reveals her medium-sized breasts. They fit her frame perfectly and I feel a pinch of envy. I’ve never been shy or ashamed of my cute, perky tits, but it’s hard not to compare and feel lacking when looking upon her modelesque figure. She radiates confidence and she gives me a look that says, I know you’re gazing upon the most beautiful pair of tits you’ve ever seen. She drops her long, flowy black skirt. Her long, smooth legs seem endless.
My eyes widen as I see her put on a strap-on and she attaches a black dildo to it. I’m really about to get fucked by a girl. I’m straight, I’m straight, I’m straight, I think. I don’t even like girls. But also, I’m her lesbian slut and she’s going to fuck me to orgasm and there’s nothing I can do about it.
“Do not come until I say you can.” Miss Rachel climbs on top of me and I can feel her soft bosom squish against my chest. The warmth pulsates from my pussy as I feel the phallus-like object being inserted into me. It fills me completely, even larger than the purple dildo from before. “What is your name?” Rachel asks me.
“Um, Jennifer,” I quiver. She twists my nipple, still attached to the nipple clamps, and I squeak a correction. “I’m your little lesbian slut, previously known as Jennifer, Miss Rachel.”
“Good girl,” she says, giving me that head pat that I’m so desperate for, the approval that I need. I feel her pumping back and forth, fucking me like I deserve to be fucked. Her breasts smush into mine and she kisses my neck tenderly. I feel the gentleness of a woman making love to me for the first time, her strong hands holding down my arms that were bound long ago. I feel her dildo filling my pussy and I feel like I’m going to explode in ecstasy, but I hold it back with every fiber of strength that I have, not wanting to disobey her.
“Miss Rachel, please, I’m going to come.”
Everything stops and my pussy is now empty. “Not. Yet.” She continues to kiss my neck and it’s the worst torture I could imagine. I was this close to having my release, to feeling the waves of pleasure ripple from my body, and she took it away from me. I need this orgasm right now. FUCK!
She holds my chin with her fingers in a familiar position. I’ve grown to enjoy these moments of her attention and approval. “Beg for it like you mean it. Beg for it like you did when you defiled my bedroom, you little tart,” she chastises.
I don’t hesitate. “Please, Miss Rachel, I need you to fuck me right now. I’m your little lesbian slut and I want you to bang me like the little tart that I am. I’m a stuck-up little bitch and I need you to teach me a lesson, but please, I’m begging you, let me come.”
It starts again. The familiar rhythmic pulse, the ecstasy of sex, of knowing that I’m being fucked by Rachel, and knowing that she is better than me in every way, more beautiful than me, more powerful than me. My face is naked and I acknowledge that I am nothing more than an average, plain jane girl being fucked by a real woman.
“I give you permission to come.” I close my eyes and release. The waves of pleasure enthrall my consciousness and I can’t help but smile. The waves pulse throughout my body for what feels like minutes and my legs spasm uncontrollably. I’m having the most intense orgasm of my life.
When I finally return to reality and open my eyes, I can see that Rachel is completely dressed in her Gothic-like attire. She cuts the ropes that bind my limbs and I am once again free from this room of torture. She takes my foot and puts my shoes on for me, and I am brought back to a memory of my mother putting my shoes on as a child. I come to a stand, wearing nothing but my platform shoes. She gives me another warm hug and says, “Good girl,” and once more gives me that pat on the head. It’s a total mindfuck as she seems to go back and forth between being a cruel mistress and a kindhearted friend that I can trust completely. I still haven’t figured out if she likes me or hates me.
“Come,” she says, and I obey as I always have. Click, click, click her heels go as she walks me to the front door, her hand on the small of my back, guiding me to my destination as if I wouldn't make it on my own. I remember the sun was shining when I drove here mid-afternoon, but it’s dark out now. I've been here for hours. Miss Rachel hands me my purse and I suddenly find myself outside naked as the day I was born with nothing but my shoes and my purse.
“Remember this the next time you darken my doorstep,” she says with contempt.
“Yes, Miss Rachel,” I reply automatically. No protest, no will to fight, I accept my defeat and walk of shame. I am going to drive home naked and I’m not going to complain.
“Remind little brother: if he touches my things, I will touch his.” I hear the door shut and lock. I feel more like a piece of property than a person.
Time to go home. I’m definitely going to obey the speed limit this time. But before I do, I unlock my phone.
Create new contact: Miss Rachel.
The bedroom is exactly as I remember it down to the last detail. Vivid memories of that awful torture session flood my mind and I resolve to not let it happen again. I am not, under any circumstances, going to let myself get tied up again. You really think so? I reply to myself.
“Stay,” Rachel commands and I obey without question. There is literally nothing stopping me from just walking the hell out of here, I think, but my legs feel stiff as boards and they don’t move an inch. Am I really going to just let this happen again? I’m confident and strong, I think. I don’t have to stand for this! When she comes back, I’m going to give her a piece of my mind.
When she returns, she’s holding a bottle of oil and a cotton ball. Oh, hell no, I think, not in a million years. If you think I’m just going to let you oil me up like one of those sluts on Pornhub, you’ve got another thing coming. I shake my head. “Listen you crazy bitch, I don’t know what kind of sex games you’re fantasizing about with that bottle of oil, but I want no part of it. I’m going home,” I say defiantly. I feel my resolve return. I’m confident and beautiful and I don’t have to do anything that this crazy bitch says if I don’t want to.
But Rachel doesn’t react the way I expect. Instead of seeing anger or surprise, she just looks disappointed. She shakes her head.
“So much talking with you. Hush, little girl.” She holds my chin with her delicate hands and peers into my soul. She makes me feel naked in a way that has nothing to do with my state of dress. I feel wetness touching my skin. She’s wiping down my face. The oil isn’t for my skin... it’s to remove my make-up. I don’t even motion to stop her, starstruck by her audacity. She has left me truly, completely, utterly naked. The contrast between myself and her now grows ever starker. I’m plain, ordinary, average, standing in submission to this goddess of a woman. My fiery spirit and resistance melts away. My desire to defy her fades away as I experience the ecstasy of her domination.
She gently pushes me onto the bed and I feel myself bounce onto the softness of the mattress. Once again, I feel paralyzed, unable to move or speak, just letting her do whatever she wants with me. I see her tying my arms and legs to the bedposts, and all I can think is, please, not again. Yet I make no motion to stop her and my actions betray my thoughts. A shameful part of me enjoys being completely powerless and I feel conflict within myself. I could ask her to stop, could I not? And the rational part of my brain says that I should. Yet I lie here embracing my bondage.
After Rachel finishes binding my limbs and I’m unable to move, she takes a seat on the bed and strokes my hair. “Good girl,” she says, and I flush, feeling a mixture of anger and pleasure. When she calls me a good girl, it makes me... happy? But how dare she. Does she have any idea who I am?
In an unexpected twist, Rachel shoves my phone in my face and says, “Passcode. Now.”
No, no, no, I’m not giving you my fucking passcode, you crazy bitch. That’s my private phone. Not. Fucking. Happening. “No,” I squeak defiantly, but it comes out sounding more like a question than a rebuke. Rachel lightly twists my nipple and I squeal, “3343! The passcode is 3343!” Have I really let her break me so easily? A part of me just wants to surrender myself to her. I’ve never met someone who is so persuasive while saying so little. The way she talks is so terse, so to the point, without the flatteries and fluff of normal speech. Whenever her siren-like voice speaks, it captures my full attention, as if listening to her is the most important thing I could possibly be doing at this particular moment.
She leans down and holds the phone in such a way that we can look at it together. “Let’s see what sort of person you are, Jennifer.” I shiver. This is the first time she’s called me by my name, and it suddenly occurs to me that I’m not sure how she even got my phone number. But I suppose that’s a mystery to solve at another time, because right now she is going through my personal photos.
“Vain, aren’t you?” I stare in silence. I can’t believe she’s going through my personal photos. It’s such a violation of my personal space, as if she’s going through my underwear drawer, but I can do nothing to stop her. I practically volunteered my passcode. “You have so many selfies. Such narcissistic tendencies. What does little brother see in you, I wonder.” I say nothing, hanging my head in shame. How do I manage to keep putting myself into these situations? I should have just ignored her and stayed home, I think. That would have been the better decision.
I watch in horror as she clicks on the folder that labeled ‘hidden’. Passcode required. 3343, she enters. I’m forced to look at my own nudes. I mean, seriously, don’t judge me, who doesn’t have photos like these on their phones? Rachel stops on a photo that I’m rather fond of. I took it in front of my tall mirror. I see my athletic, toned body, my perky breasts and shapely legs, tiny hints of lines that define my abs, a familiar smirk that says, I have it. My pose is effortless, confident. Rachel smiles. “I like this confidence.” She pauses and I can feel her devilish energy. “I will enjoy taking it from you.”
No, no, no. You’ve got to be kidding me, I think. I’ve been stripped, spanked, had my bare face exposed, tied up, and forced to watch in silence as this evil succubus goes through my most private photos. This is so unfair. What is with this psycho family’s obsession with torture? Sigh. At least it can’t get much worse than this, right?
She holds my chin with in her soft, delicate hands once more. “Everything you did in my room. Now.”
I pause for a moment, considering my options, but I’ve been here long enough to know what’s going to happen. I’ll put on a show of defiance and then she’ll pop me like a cherry until I squeal. I decide to just save myself the embarrassment and give her an abbreviated version. “Josh tied me up and we had sex. It was his idea. I swear. Please, I’m sorry, I didn’t know it was your room. I would never do something like that on purpose.”
She peers at me. “Is that everything?”
“Yes,” I reply, not really wanting to go into exquisite detail of Josh’s tickle torture, the way he sliced up my clothes with the fabric scissors, or how he had me pleading for sex.
Rachel walks to her chest of drawers and pulls out a kind of chain with some attachments at the end. It looks like some kind of modern torture device and I really don’t want to find out what it does. “Liar.” She sees right through me. My body language is completely transparent and I can’t hide anything from her. I can feel cold metal clamping down on my incredibly sensitive nipples and I grit my teeth. I fight against my bonds, but my limbs are completely immobile. “The truth. Now.”
I break almost immediately. I tell her everything. About the bet, the tickling, the spanking, the sex. I even tell her about being pulled over for speeding and my humiliation at the gas station. I tell her every detail until she’s completely satisfied. I submit myself completely to her. All my bravado and spunk has faded away and I sink into complete obedience. I want nothing more than to fulfill her every command. If she told me to say I’m a dirty lesbian slut, I would say I’m a dirty lesbian slut, thank you, my sexuality be damned.
“Good girl,” Rachel says, stroking my hair and patting my head. She caresses my chest with a feminine grace and gentleness that no man could replicate. “I forgive your transgression.” I have her forgiveness and it fills me with joy. It should seethe me with anger, but such emotions have long since faded away. I surrendered myself. She whispers into my ear, “See that it doesn’t happen again.”
“I promise to never touch your things again, Rachel,” I reply obediently, wishing nothing more than for her approval.
She slaps my face for the first time tonight and it stings. “Miss Rachel!” I squeak.
“If you ever do,” she replies, leaning in again to whisper in my ear, her siren-like voice serenading me with primal fear, “I’ll put you on display like a Christmas tree. The world will know your conceit.” My imagination runs wild. I can see myself tied naked to a tree in the middle of the quad, my tight athletic body freely gazed upon by thousands of students on their way to the first class of the day. The guys whistling and hooting, the girls snickering at my misfortune. It would be a fate worse than death. I silently make a vow to never touch her things again. I didn’t even do it on purpose in the first place. It wasn’t even my fault. It was all Josh’s idea. But I know better than to talk back.
“I promise, Miss Rachel,” I plead, hoping for her tender side, wishing for her to pat me on the head and tell me I’m a good little girl. I find myself perplexed at my behavior. I’ve been completely dominated in a way that not even Josh managed to do. All of my spunk, my bravado, my confidence, it might as well be a distant memory.
“Tell me what you want, girl.” She holds my chin with her delicate fingers and I’m forced to look into her eyes. I must not tell lies, I think. But this is my chance to go home. For the first time tonight, she’s asking me what I want.
“I, um, I want to go home,” I reply. “Miss Rachel,” I add quickly, careful to show her the respect she commands.
She shakes her head and I can feel her disappointment again. “I would grant your wish. If you were being honest.” She sees right through me. She can always tell. My eyes give everything away. I can hide nothing from her. It's true. I am a liar. I want this. “The truth.” She twists the nipple clamps and I once again find myself broken.
“Miss Rachel, please tickle torture me until I beg you to fuck me like the little lesbian slut that I am!” I squeak.
Fuck. I. Cannot. Believe. I. Said. That.
“Where are you ticklish?” she says. Her voice is now light and sing-songy. I’ve made her happy. Miss Rachel is pleased.
“Underneath my leg,” I say. I don’t even consider lying. It’s pointless. She can see through my deception as clearly as the morning light. What have I done? I can’t believe I just asked her to tickle me. I fucking hate being tickled. I’ve hit rock bottom. It doesn’t get any worse than this. I’m not even attracted to women, yet here I am, begging this beautiful woman to tickle me and then fuck my brains out. Straight, are you? I think to myself. Well, a noodle is straight until it’s wet.
Her fingers curl and graze my most sensitive area and I explode into laughter. Ha, ha, ha, fuck, why did I, ha, ha, ask for this? I can’t think at all as I involuntarily thrash against my bonds and cackle uncontrollably. I feel the nipple clamps bounce uncomfortably as I squirm, my sensitive areola pulsing, and my pussy ignites with pleasure. I unconsciously look at the dresser to check how much time is left and find myself remembering that there is no timer. This ends when Miss Rachel says it ends.
I’m not sure how much time has passed, but it does not take Miss Rachel long to break me. I hear myself begging. “Miss Rachel, ha, ha, please, anything but tickling, ha, ha. I can’t take it! Please!” I laugh, bellow, cackle, squeal. I have no dignity left. I am her toy to use as she wishes. Miss Rachel looks pleased. “Please fuck me, Miss Rachel. I need it! No more, ha, ha, tickling!”
“Good girl,” Rachel says, her harmonious voice’s approval bringing me glee. She pats me on the head and steps back. She strips off her black crop top and reveals her medium-sized breasts. They fit her frame perfectly and I feel a pinch of envy. I’ve never been shy or ashamed of my cute, perky tits, but it’s hard not to compare and feel lacking when looking upon her modelesque figure. She radiates confidence and she gives me a look that says, I know you’re gazing upon the most beautiful pair of tits you’ve ever seen. She drops her long, flowy black skirt. Her long, smooth legs seem endless.
My eyes widen as I see her put on a strap-on and she attaches a black dildo to it. I’m really about to get fucked by a girl. I’m straight, I’m straight, I’m straight, I think. I don’t even like girls. But also, I’m her lesbian slut and she’s going to fuck me to orgasm and there’s nothing I can do about it.
“Do not come until I say you can.” Miss Rachel climbs on top of me and I can feel her soft bosom squish against my chest. The warmth pulsates from my pussy as I feel the phallus-like object being inserted into me. It fills me completely, even larger than the purple dildo from before. “What is your name?” Rachel asks me.
“Um, Jennifer,” I quiver. She twists my nipple, still attached to the nipple clamps, and I squeak a correction. “I’m your little lesbian slut, previously known as Jennifer, Miss Rachel.”
“Good girl,” she says, giving me that head pat that I’m so desperate for, the approval that I need. I feel her pumping back and forth, fucking me like I deserve to be fucked. Her breasts smush into mine and she kisses my neck tenderly. I feel the gentleness of a woman making love to me for the first time, her strong hands holding down my arms that were bound long ago. I feel her dildo filling my pussy and I feel like I’m going to explode in ecstasy, but I hold it back with every fiber of strength that I have, not wanting to disobey her.
“Miss Rachel, please, I’m going to come.”
Everything stops and my pussy is now empty. “Not. Yet.” She continues to kiss my neck and it’s the worst torture I could imagine. I was this close to having my release, to feeling the waves of pleasure ripple from my body, and she took it away from me. I need this orgasm right now. FUCK!
She holds my chin with her fingers in a familiar position. I’ve grown to enjoy these moments of her attention and approval. “Beg for it like you mean it. Beg for it like you did when you defiled my bedroom, you little tart,” she chastises.
I don’t hesitate. “Please, Miss Rachel, I need you to fuck me right now. I’m your little lesbian slut and I want you to bang me like the little tart that I am. I’m a stuck-up little bitch and I need you to teach me a lesson, but please, I’m begging you, let me come.”
It starts again. The familiar rhythmic pulse, the ecstasy of sex, of knowing that I’m being fucked by Rachel, and knowing that she is better than me in every way, more beautiful than me, more powerful than me. My face is naked and I acknowledge that I am nothing more than an average, plain jane girl being fucked by a real woman.
“I give you permission to come.” I close my eyes and release. The waves of pleasure enthrall my consciousness and I can’t help but smile. The waves pulse throughout my body for what feels like minutes and my legs spasm uncontrollably. I’m having the most intense orgasm of my life.
When I finally return to reality and open my eyes, I can see that Rachel is completely dressed in her Gothic-like attire. She cuts the ropes that bind my limbs and I am once again free from this room of torture. She takes my foot and puts my shoes on for me, and I am brought back to a memory of my mother putting my shoes on as a child. I come to a stand, wearing nothing but my platform shoes. She gives me another warm hug and says, “Good girl,” and once more gives me that pat on the head. It’s a total mindfuck as she seems to go back and forth between being a cruel mistress and a kindhearted friend that I can trust completely. I still haven’t figured out if she likes me or hates me.
“Come,” she says, and I obey as I always have. Click, click, click her heels go as she walks me to the front door, her hand on the small of my back, guiding me to my destination as if I wouldn't make it on my own. I remember the sun was shining when I drove here mid-afternoon, but it’s dark out now. I've been here for hours. Miss Rachel hands me my purse and I suddenly find myself outside naked as the day I was born with nothing but my shoes and my purse.
“Remember this the next time you darken my doorstep,” she says with contempt.
“Yes, Miss Rachel,” I reply automatically. No protest, no will to fight, I accept my defeat and walk of shame. I am going to drive home naked and I’m not going to complain.
“Remind little brother: if he touches my things, I will touch his.” I hear the door shut and lock. I feel more like a piece of property than a person.
Time to go home. I’m definitely going to obey the speed limit this time. But before I do, I unlock my phone.
Create new contact: Miss Rachel.
Last edited by MissAriel on Fri Dec 09, 2022 7:42 pm, edited 2 times in total.
See my collection of stories here: MissAriel's Story Archive
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Re: My Boyfriend's Sister (Complete)
Again a hot story. Hope there is more where that came from.
You deserve this
You deserve this
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Re: My Boyfriend's Sister (Complete)
There's always room for another story! I'm not quite sure where things will go from here, but there are lots of possibilities. Josh won't be too happy that Jennifer slept with Rachel.
Definitely no threesome or anything like that, Josh and Rachel are rivals. I think it'd be fun to see Jennifer suffer as she finds herself in the middle of sibling rivalry. I'm not quite sure how it will play out. All I know is Jennifer probably shouldn't bother wearing underwear.
Definitely no threesome or anything like that, Josh and Rachel are rivals. I think it'd be fun to see Jennifer suffer as she finds herself in the middle of sibling rivalry. I'm not quite sure how it will play out. All I know is Jennifer probably shouldn't bother wearing underwear.
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Re: My Boyfriend's Sister (Complete)
This story was very hot and intense! It reminds me of the movie Cruel Intentions, with the way Rachel acts, and even the sibling rivalry being hinted at.
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Re: My Boyfriend's Sister (Complete)
I'm actually glad you said that. There were two inspirations behind the Rachel character. One was *definitely* Sarah Michelle Gellar from Cruel Intentions. You have such good pop culture knowledge!superevil7 wrote: ↑Mon Jan 02, 2023 4:13 am This story was very hot and intense! It reminds me of the movie Cruel Intentions, with the way Rachel acts, and even the sibling rivalry being hinted at.
The other is "The Witch" from an anime called Goblin Slayer. She's a purple haired, busty, sexy anime lady that has a very distinctive style of speaking, short, sultry words, very direct. I imagined when Rachel talked, she spoke in the same sort of way.
Example of the Witch Talking
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Re: My Boyfriend's Sister (Complete)
The way she speaks is almost hypnotizing.MissAriel wrote: ↑Mon Jan 02, 2023 4:40 am The other is "The Witch" from an anime called Goblin Slayer. She's a purple haired, busty, sexy anime lady that has a very distinctive style of speaking, short, sultry words, very direct. I imagined when Rachel talked, she spoke in the same sort of way.
Example of the Witch Talking
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