Alright, so i wrote another story about how my sister caught me in self bondage one time. From then on, we've gotten closer to each other, and we've done some bondage together before, turns out we both have a bit of a bondage fetish.
I spent a good portion of my life wishing I was a girl, I explained this more in the last story. Today, I'm happy being male, but I feel like I was a pretty feminine boy. As a result, I would sometimes cross dress with my sisters clothes if I had the chance. After the incident where my sis caught me (I was wearing her pjs at the time too), she's known this about me, and even has let me wear her clothes sometimes when it's just me and her.
The first time that me and her ever did real bondage was on a night that my mom was going away. She had left around noon on a friday, and was going to come back the next afternoon. When I first learned about the trip, I asked my sister "can we do bondage that night?". She looked at me, smirked and said, "alright, I'll tie you up real good that night!". I was so excited for this night to come now... It was 2 weeks away and my sister kept teasing me about it in those weeks. She would tell me "I've got great plans for tying you up!" I couldn't wait for this night
Finally, it came. I wanted to get right into it, but my sister wasn't ready. She told me, "hang on kid, we've got a little while before I'm ready!". She could tell that I was really anxious. She told me, to just go wait in my room and shut the door, no leaving under any circumstance, it'd be like a jail cell. So i did that, pretending that I was actually in prison. At that time, I kept a journal, and I was writing about how excited I was for that night, being my first time really tied up by someone else! About an hour passed and finally she knocked at my door. She told me that she had to run out and do some errands. She told me that if I had to use the bathroom, I better do it now, because she wanted me to stay in my room till she got home (which I obeyed). So, I went to use the bathroom, and when I got back there, she told me to turn around, and she pulled a pair of handcuffs out of her purse and slapped them on my wrists! she wasn't done, she pulled leg irons out and cuffed my ankles together! She told me "you are not to leave this room until I come back, you understand?" I told her "yes ma'am" These are real, so there's no getting out even if I wanted to, my bondage had begun. I struggle in the cuffs and I keep pacing around my room waiting for her to get back. Eventually, I just get on my bed and lay on my stomach until she returns
Finally, she comes home and comes to my room. She must've been gone for over an hour. She escorts me to her room where she uncuffs me. She tells me "strip down and put these on" she presents me with an old bathrobe of hers an old pair of slippers, and a pair of red panties. if you didn't read my other story, I love robes and slippers, so this makes me happy, and the panties definitely gave me an idea of what was happening next. The cuffs go back on, then she sits me down in a chair and tells me "I'm gonna make you into a pretty girl!" (I should also mention that my sister and I are about the same size, so clothingwise, her clothes fit me fine) I'm very nervous and excited about this part. at the time, my hair was a little longer than shoulder length, so she tied it into pig tails (I rarely even wore it in a ponytail). Then she starts putting makeup on my face. The whole time she was doing it, she was telling me stuff like "us girls have to make sure we're pretty all the time". I loved hearing this stuff since I still wanted to be a girl when this was happening. And since i know nothing about make up, I can't really explain to you all exactly what she was doing to my face, but she basically did to me how she does her makeup for when she goes out to a club. She took a good look at me and said that she was proud of her work! My face is really not very masculine, so with all the make up and my long hair, i definitely looked feminine, I loved it!
Next thing she does is stand me up and take my handcuffs off and tells me to take my robe off, I do, so I'm standing there wearing only the panties, and slippers! Oh, and of course leg irons still! She notices that I have an erection and just says "I'm just gonna ignore that" it was an embarrassing moment since she is my sister, but I couldn't help it! She brings out a lacy black bra and puts it on me, of course, it needs to be stuffed. It's a b-cup bra, btw. She grabs some socks and stuffs them in there till the bra is filled, next she grabs some duct tape to tape the bottom of the bra onto my chest just to ensure the socks don't come out. She runs to her room and grabs a knee length skirt and puts it on me, it fits really well! The skirt is mostly predominantly red, it's a red and black plaid skirt. I'm loving this so far. For the times that I've cross dressed in my life, i never felt like a girl, i felt like a boy in girl clothes. But once that skirt and the bra were on my, I finally felt like a real girl! Next comes the tights or pantyhoes, or whatever they're called. They're jet black, and they cover my feet and look amazing with the skirt. She makes the comment "see how much trouble a girl goes through to look pretty??" I laughed.
The top she grabbed for me was black with some white outline to it. It was short sleeve and had buttons and a tie to close it that goes about 3 inches under the breasts. That's the best way that I could describe it. She told me "I thought you'd like this one, since its kinda like a robe", I appreciated that. She buttoned it up, and left enough buttons up top open to show my "boobs".
She comes in with a pair of black high heels and tells me "take your slippers off, if you're gonna be a real girl, you gotta put some heels on!" I got so happy with that! The heels had a buckle right around the ankle, so I knew that no matter how much I would struggle in my bondage that night, they would be staying on. She puts them on my feet and tells me to walk around in them for a bit, I do, but very slowly. She grabs another pair that she puts on and shows me how to do it "Every girl can do it!". I get a little better at it
She looks at me and decides that my hair doesn't fit the outfit, so she takes the pig tails out, and decides that it should be down. She puts some hairclips in it, brushes it, gives me bangs, and really makes it look like a girls haircut. She looks at me and says, "you make such a pretty girl! almost prettier than me!" I laugh and start to blush... She puts a necklace on my and a few bracelets, and my transformation into being a girl is complete. I just keep looking into the mirror and I'm loving what I see. She asks me "how do you feel?" I tell her "I love this! I feel right!"
As I'm looking in the mirror still, she comes up behind me, grabs my arms and cuffs me behind my back. she puts leg irons back on me. She tells me that the real bondage fun will start after dinner. She orders a pizza and when we eat it, I have to eat it with my hands handcuffed in front. I was so nervous that i'd get it on my outfit, so she took the bathrobe I was wearing earlier and put it on me backwards (like a snuggie but back before they were around!) and luckily I dont get anything on the robe. I'm cuffed behind my back again, and in a few minutes she takes me back to her room.
She tells me that whenever she's played with bondage before, she's used a safe word, she tells me that my safe word is "slippers". She stuffs a sock in my mouth and duct tapes it in there with a few pieces of tape. When the gag is complete, she tells me to practice saying "slippers" so she knows what it would sound like. She sits me in a chair, takes off my leg irons and pulls out some rope. She ties my ankles together, and my knees together. She takes off my handcuffs and ties my wrists together. She ties my elbows together and with the rope she makes sort of a spreader bar since I can't make my elbows touch each other. She ties a piece of rope around my wasit and connects my wrist ties to it, with a little bit of slack. She says "i've done a good amount of bondage before if you couldn't tell"
Next may have been the most awkward moment. She told me that I she was going to hog tie me, but with an erection I had to be careful when getting onto the floor, well, I was completely helpless, so she was the only one who could do soemthign about it. So she grabs a few pillows and put them on the floor and gently lays me down. Finally I'm completely on my stomach and she pulls the pillows away. There's some pain in this process, but overall not too bad. SHe makes a comment like "I'm so glad I don't have a penis"
She pulls my legs up and puts some rope around my ankle ropes and my wrist ropes and ties it as tightly as possible. I'm now very securely tied up, and my sister has done her job. She says "poor little damsel in distress, you've been a bad girl. I'm gonna leave you here for a bit but I'll be back to check up on you". She leaves and shuts the door. I'm left alone, a 16 year old boy dressed up like a girl tied up by his sister. This is the most amazing and exciting moment of my life at this point. I struggle to get free but nothing is getting loose. I moan through my gag, but it's heavily muffled.
I'm all alone in bondage. I realize that struggling did nothing, so I concede to my bondage. I start thinking about the situation and I realize how this is the first time in my life that even if I wanted to get out, i couldn"t. I was tied up well, only to be released whenever my master wanted me out. I start thinking more and more about my situation, I wasn't a boy tied up by his older sister, I was a girl, I felt like I girl, I looked like a girl, I was a girl. This really changed so much about the bondage. Like, I feel more vulnerable as a girl, weaker and more helpless. I feel that no matter what I would not break free. I feel more of a desire to be submissive than when i'm dressed as a boy. It was really a great experience. My sister came in to check up on me a few times and changed my position around a little. The 3rd time she came in she took me out of the hogtie. and just had me stand up for the rest of the time. She told me that she was gonna take a shower and she'd be back after that to release me. Standing up, while tied up and wearing her heels was so painful! After about 30 minutes of this she came in after her shower and untied me. "Did you have fun, princess?" I giggle and nod my head. she hands me my bathrobe and slippers and tells me to go take a shower. I take one last look in the mirror and go into the bathroom. After my shower, i get into my pjs, robe and slippers and go to find my sister sitting on the couch watching tv and playing around with her handcuffs. I join her and she cuffs me in front of my body, and that's how the night ends. After about 30 minutes of that, she uncuffs me and has me put them on her. She stays in them till we go to bed
Well, that was the first time my sister tied me up. We haven't done anything that big and evolved afterwards, but we've done some stuff. I'll try posting more on that, and stories about my gf and I doing bondage!