9 comments/ 26321 views/ 12 favorites Caroline Finds Out Pt. 01 By: thingsweneedtowrite It's funny how in fantasy there is a common thread of 'wanting to get caught'. But for that fantasy to work, you have to be caught by someone who upon catching you treats your fantasy kindly. So often I am able to read about men just like me who dress up in lingerie, who are exposed by someone who ultimately matches the precise identity of the person they hope to be caught by. For some men they want to be caught by their partner who will now embrace this side of them (sometimes after struggle, sometimes right away), or a family member who takes them under their wing and helps them blossom (sometimes after a struggle, sometimes right away). But it always ends gently in print. Everyone is happy, sexually fulfilled and comfortable with how the entire scenario unfolded. I'm still waiting for my gentle ending. I used to think it would be sexy to get caught. Maybe I was hypnotized by the stories I read and figured it always ends up okay so that's how it would end for me. But for someone who fantasized about being caught, I was careful. If I wanted to get caught I wouldn't have taken a picture in my mind about how my mom's panty drawer looked when I went through it looking for something to dress up in. I wouldn't have done the same with my sister's closet as my play progressed. I wanted to get caught in fantasy, but I never acted like it. Overtime, I developed a protocol. I would only use panties in the hamper for masturbating in, and always near the bottom of the pile. I would never try on something that didn't fit that would risk being torn or stretched. I wouldn't move anything that I couldn't put back right away. I never played dress up if I didn't know where everyone was and for how long they would be gone. Back then, I thought I was probably pretty good at it. But now that i'm older, knowing how laundry is done, I have no doubt I left some evidence behind at times. I must have. When I started living with different girlfriends, I did much the same with their lingerie, but I had more time to play because I only had to worry about one person coming home. This is when I discovered this part of me wasn't going away. With more time, and a more evolved sense of sexual identity I began to embrace the feminine part of me. My play wasn't always sexual either. I would sometimes put on some panties, a summer-dress and some jewelry and work quietly around the house, doing chores or working on my computer. It was also intensely sexual. I would more often fill myself with her toys and imagine what it must be like to make a man hard for you and be taken by him. I would push in their vibrators or dildos and imagine my ass were a pussy and I was being taken like a girl. And I was always careful. As a married man, I hid this part of me. I invested it in anonymous people in online forums, shared photos of me from the neck down to arouse other men and women. I had two online Dommes with whom I had distance and no chance of ever meeting. I thought I had it under control. Forty-three years of practice and not one slip. Last month though it all changed. I was flying through Toronto to Vancouver and booked a visit with my sister Caroline who lived in Mississauga, closer to the airport than my home town. It made sense to tie in a visit with her as a part of my travel. In exchange for a night away from a hotel, I'd treat her to dinner and catch up in person on some of the things that have been going on in both our lives. She was game, but would be at work when I arrived so she arranged to leave a key to her apartment out for me and invited me to use the space until she was done work. I would be lying if I said as I made the drive I didn't think about dressing up at her place, but I did so in a way that tried to keep it as just a fantasy and not something I would actually do. After getting in to her place, settling in for a moment, and trying to find another distraction, it was less than an hour before I went in to her bedroom. It's funny how very little changes as you grow up. I knew almost by instinct which drawer my sister would keep her panties in, and that they would share space with her bras and stockings. Her panties would be lined up in the middle of the drawer, her bras on the right - neatly arranged, and nylons or stockings on the left. It's funny how that feeling never changes either. The butterflies, the anticipation, the curiosity. I opened that top drawer and was at once not surprised (I had guessed right), and surprised (because my big sister had obviously grown up). Also what that surprise did to me. It is one thing to have masturbatory fantasies while wearing your sister's panties as a teen, and quite another to look at a lingerie drawer and suddenly be able to picture your sister as a beautiful, sexual being. I was hard. Today wasn't going to be anything but sexual. I closed the drawer not to stop, but because of the protocol. I was going to masturbate in her panties, so I needed to find some from the laundry hamper. Instinct. To her closet, where she keeps her hamper. Not surprised (I had guessed right). Surprised (I wanted not just to wear my sister's lingerie, but become her for a moment). There was a pair of black lace boy-short panties in the pile. Crumpled and worn. I held them and thought about her day. Whether she wore them to work and just back home, or if she was out on a date. Whether at any point in the day something happened to make her wet. Whether she wore them with a skirt or with pants. How it looked when she pulled them down to pee. For one of the first times in my life, I was stuck imagining my sister. I held them to my face. I tried to see if I could catch the essence of her cunt. I could. I undressed. I folded my clothes neatly and put them aside. I put on her panties and looked under her bed. Instinct. I found her shoebox that she kept her toys in. As a teen, there wasn't much in there. She only had one vibrator, and to this day I would never know how or where she got it. Just that one little toy hidden among old birthday cards and mementos. As a grown woman, she had so much more. A we-vibe, a long but thin white vibrator, a purple cock-shaped dildo, a vibrating butt plug, fuzzy hand-cuffs, lubricant. Fuck. My sister was sexy. My sister was maybe kinky. I pulled out the white vibrator and lay in her bed. I closed my eyes and held the vibrator to my lips and started to lick it. Then suck it. I wanted to taste Caroline off her toys and know what she tasted like. I got it wet, I moved it down my tummy, and slid it over my cock. I held it on the underside of my cock like it were a clit, and I came. I came imagining her playing with herself just like this. I turned the vibrator off. I wiped it clean. I took the panties off and put them back in the hamper. I took my clothes to the shower and cleaned up. I turned on my computer, and worked for the rest of the day. Caroline came home just after 5:30 and got ready for dinner. She changed in her room and I felt like I'd gotten away with it. She didn't say anything and we left for dinner. I'd learned to look for the cues. I've nearly been found out before, but always kept an explanation at the ready. There was no questions from her, no change in her behaviour. Unlike most fantasies I read, I didn't get caught on a layover and she didn't lose her mind at first and then torment me in to showing her more. In the morning we ate, and I got ready to leave for my trip. We left together and I made my flight in great time. I sent a thank you text to my sister before I took off and boarded the plane. I landed, checked in to my hotel and unpacked. The difference between fantasy and reality is that the reality of getting caught hits you physically right away. Your body goes almost in to a state of shock. You sweat instantly, and its cold. You almost pass out as your body realizes what has happened. You get scared. Your brain rushes and rationalizes. And you almost faint. I know this because as I unpacked I found her cum soaked panties in my bag with a note that said "I don't ever want these back." Nothing else. No "we need to talk when you get back" or "naughty you" or anything that made what happened seem at all okay. When that happens you don't want to jerk off. You don't want to slip in to those panties and do it again. You don't want to confess to your sister you wanted to be like her. You can't explain it. You just sort of hold them in your hand, paralyzed for a moment. And then you keep moving. Because you have to. You can't just stand there forever. You keep unpacking, you look at your blackberry, you eat, you push it aside. You don't cum at a moment like that. You cum later, when you wake up at about 4am and turn on all the lights and start going back through your things, checking and rechecking just to make sure. You cum when you realize that one of your pairs of underwear is missing. And you keep cumming in those panties with the hope that this story ends with you being okay. Caroline Finds Out Pt. 02 If you are a man, you understand the feeling that I soon expected myself to have. I was alone in a hotel room and I was at the same time confused and aroused. I started to piece together what I thought I knew. I saw her toys, so I knew that at a minimum she was a very sexual woman. I saw her note, so I knew that she knew I used her panties to masturbate but I didn't allow myself to determine whether she knew I wore them or anything of hers for that matter. I knew she had something in mind because she deliberately took a pair of my underwear, but what that was I wasn't sure. That's all I knew. Anything else I would just be making up. And that was what intrigued me. I was alone in a hotel room and I got ready for bed. I lay there thinking about what I didn't know. I started to picture her boyfriends, her ex-husband - the men in her life I never knew, and I wondered about the things she did with them. I started to picture them doing the things men like to do with women when they're intimate. I pictured them hard for her, admiring her body, kissing her, their cocks in her mouth, her pussy, her ass. I thought about the things she may have tried and never shared with anyone. I was hard, and my thoughts kept bouncing to different scenes and guys and began to realize something, maybe more acknowledge something that I think any of us with siblings realize, that our brother or our sister is probably in a lot of ways like any of the men or women in our lives and she probably enjoys many of the things I've done with the women in my life. That night was the first time I thought of being with her. As my thoughts drifted to fantasy, I was suddenly overcome with this curiosity - a very specific curiosity - that I would not be able to shake. I wondered if my sister swallowed. Just like that. And no longer was I thinking about boyfriends or her ex-husband, I was thinking about me. I was thinking about my sister's mouth on my cock, in bed, giving me head and I wondered if when I came she would pull her mouth off of me and masturbate me through my orgasm and make me cum on my chest and tummy. . .or if she would hear me tell her I was about to cum and let me finish in her mouth and swallow. That's when I came. There was no answer. The feeling I expected to have was one that I have experienced before. There have been times when I have been on tumblr chasing images and finding myself deeper down the rabbit hole than I imagined I would go and felt a bit of shame or guilt at the thought that made me cum. There have been times where my play has involved toys or acts that lead very much to that same feeling. I would clean up right after and do my best to put what just happened out of my head. Not this time. Laying there in that bed, that night, I felt no guilt, no shame, making myself cum thinking about my sister's mouth on my cock. In fact it felt a bit, well, right. As I drifted to sleep, those men were replaced by thoughts of me. Off and on through the night I would allow myself to think of her in ways I'd never thought of before. I awoke the next morning less nervous about what had happened. It was as if a night away, and the travel and the anonymity of being in a hotel had put more distance behind this whole thing than may actually be true. I believed that maybe because I had these thoughts, these feelings, that maybe she did too. I got butterflies when that thought came to my head. The thought of my sister in bed touching herself thinking about me had me hard again. And for the second time in less than eight hours, I'd cum thinking about her again. I sent a text to let her know I'd made it safely to Vancouver and thanking her for letting me stay over. I got in the shower. I checked my phone and there was no reply. I dressed and went to the conference. I checked from time-to-time hoping for something, but she didn't reply. I ate alone that night and went back to my room, exhausted as much from the day as the thoughts that kept my mind more active than it needed to be; about why she wasn't texting, about the feelings I was having, about whether she enjoyed being fucked in the ass. My thoughts were never empathetic. They were never about her not texting because she was offended that I masturbated with her panties or she suddenly realized I had a crush on her. It was always something else. She was out with friends. Her battery was low. I went to bed that night and thought about her. I thought about my sister Caroline in bed with me, on her hands and knees while I took her from behind. I thought about what she sounded like when she came, and wanted to make that happen. I didn't think about what got us to that point. In some ways over the past day and a half I already felt in some ways like we were together. That we'd always been intimate in some ways with all that we'd been through and the times we'd been there for each other. Of course we were in bed together like that. It was only natural. I let these thoughts take over even more strongly when I woke up the next morning to a message from her. "Glad you made it safely. Let me know if you need to stay over on your way back." I suddenly needed to stay over on my way back. Caroline Finds Out Pt. 03 The flight home was unbearable. Any confidence I had on the ground, I lost in the air. I realized as we were climbing how weak a foundation my entire fantasy was built on. I had gone from my sister finding out I'd used her panties to masturbate, to somehow thinking first of all that this would be just fine when I got home and second of all that it was okay that I'd spent the past four nights having orgasms imagining her and I together. In the air, everything suddenly seemed inevitable. I would land. I would deplane. I would get in the car. I would drive to her place. And then who knew. I decided that the worst possible scenario would see me copping to jerking off in her panties. I could do my best to rationalize somehow, like I was stressed before the trip, I needed to unwind, I made a mistake, I was sorry and can we move past it. That didn't seem bad at all. It wasn't ideal, but it wasn't bad as far as worst possible scenarios go. I could live with that. And inevitably I did land. I did deplane. I did get in the car. I did drive to her place. And I went to her apartment. Her place was quiet. She was alone, as expected. It was a bit late and it had been a long day. She greeted me with a glass of wine, a slight hug and an invitation to put my things away and take a shower to refresh. I didn't want any of that. I wanted to get this over with right away. I could have said something and initiated our conversation, but I just said thanks and that I'd love a shower. It had been a long day. I didn't get hard. I couldn't get hard. I was anxious. She didn't walk in. She didn't knock on the door and join me. She didn't watch me towel off. She didn't follow me to my room. I showered, I put on fresh clothes, and I met her in her living room. She had poured for me a glass of wine. I sat down. "I'm confused, Sean." That's how it started and I suddenly knew it was going to be harder than just a confession that I masturbated in her panties. "I'm not angry. I don't want you to think that. I'm just trying to process this." What the fuck does that mean? Trying to process what? It was just one time. Oh fuck what's going on. "I think I knew before last week, to be honest," she continued. "But there was never really anything I could point to and say 'a ha! I knew it. But there were always little things I would notice from time to time." Jesus fuck she knows it wasn't just once. This is not good. I sat in stunned silence. "I'm not mad that you went through my things, Sean. But please tell me the truth. You've been doing it a long time, haven't you?" "I have," I could only say quietly. "Okay. Thank you for being honest. Do you know what I thought about the most while you were gone?" I could only nod no. "I wondered why you never came to me about any of this. We are close. We always have been. You and I know so much about each other. You were there for me through my divorce, I was there for you when you were having your troubles with your marriage, we were always there for each other in so many ways, but I get that it can be hard to talk to me about things like this." I wasn't going to say anything. I couldn't. But obviously it is hard to talk about things like this with your fucking sister. "It is a lot to process. It hasn't been easy. But it is less about what happened and in some ways more about a lost opportunity for us." Pardon. Wait. What does that mean? I continued in silence. "Sean, here's the thing. I've always been a bit, well, sexually adventurous. Always. I don't just mean that when I was older and learned more about myself I found myself enjoying new things. I always knew I was different. That I liked different things than other people and it started for me very early. I wondered if it was the same for you. I wondered if somehow we couldn't have become even closer if we had been able to share this part of us. I know it isn't something a brother and sister often do, but who else may know why it is that I like the things I do? Did you always feel a bit different?" I nodded yes. I had yet to speak since my confession. "I sometimes wonder if I would have enjoyed a bit more confidence in this part of me if I knew I wasn't alone. I wonder if I would have felt less guilty about being bicurious if I knew that you were too. Or if I'd have been more willing to ask my partners to try things I wanted if I knew someone just like me, who has learned to love me unconditionally thought about those same things." At the mention of unconditional love I got butterflies. "But I had to find out like I did. I know I could have said something long ago. I could have asked and started this whole conversation long ago, and who knows what then? Maybe I'd be different today. Maybe you would. Maybe we would be different together." My worst case scenario guess was way off. I no longer knew where any of this was heading. "Anyway, it's a lot to think about. I'm not sure what I'm supposed to do now or if I'm supposed to do anything. Is there anything you think you should tell me that could help me understand this?" I had to say something. Just not the something I wanted to say. So I went with this: "I'm sorry, sis. I am different too, but I think you know that. Maybe not as much as you could know, but I have wants that I am sometimes unsure of myself. I couldn't ever explain this stuff to you. I'm not sure I can yet." "Sean, you didn't just go through my panty drawer, did you?" "No." "Did you use something you found in the box under my bed?" "Yes." "I think that's enough for tonight," she said. "But I want you to have these back." She handed me back my underwear. "It was silly of me to do that. I felt like I needed to do something though so you finally knew that I knew. Do you still have my panties? I wouldn't mind having them back." Fuck. Fuck fuck fuck fuck. Yes. Yes I still have them. They're still wet from the morning probably, tucked away in my bag still. "Yes, I still have them. But I should probably wash them first, Caroline." "No. I can wash them. Please just get them for me." I walked in to my room with that same dreaded inevitable feeling coming over me. I got her panties. They were still wet. I walked back to the living room. She was texting on her phone. She stopped to hold out her hand. I gave them to her, looking her in the eyes the whole time not out of bravery or boldness but out of wonder what would happen next. She blushed when she felt them still wet. I think she smiled a little. "it's a lot to process, Sean." She stood up, she kissed my cheek slowly and went to her room. My phone vibrated. I checked it right away. It was a message from my wife. She was glad I was back safe, all was well at home. She'd been texting with Caroline while I was gone and she told her she was going through something that she needed some help with and she just got another text from Caroline asking if it was okay if her brother spent a couple of days with her? My wife hoped all was well and said to call her tomorrow if I needed anything but to not rush home. It was a lot to process. Caroline Finds Out Pt. 04 "That just made me a little wet, Sean." I know I'm not the only person in this world to have ever had a crush on a sibling. And if you are at all like me, or anyone else for that matter you probably remember a moment where that crush went either of one way or another. In university I had a guy friend that I adored, and wanted to be with sexually. But you don't want to be wrong about that sort of thing if you're going to try and make it go forward. He wasn't the first guy I'd fallen for, but with the other two there was always this moment where I convinced myself I knew that it wasn't going to happen based on that moment. It could be something someone says, or the way they look at you at a certain moment and you let your brain determine right there and then if it goes any further. With Joel I knew the day that I seduced him it was going to happen. Our moment came when we were shopping for a meal that we had decided we were going to make instead of going out for dinner when I went to see his new place. As we picked out things, I looked at our basket and said "It looks like we're getting ready for a date." It was a throw-away line if it needed to be. One that I could laugh off if I caught a glimpse of annoyance or discomfort. But he looked in my eye a little longer and said "then we should get some wine." So I slept with Joel. Because I knew. Now my sister was sitting across from me in the restaurant, looking me right in the eye and telling me my confession that I had masturbated to the thought of being with her had made her a little wet. And that in just a few seconds, we would have our moment. "When did you last cum thinking of me, Sean?" "This afternoon, sis." Before this, the evening was comfortable but unpleasant. If she was having any trouble processing what had happened before I left on my trip, she was not going to be denied the courtesy of having whatever information she needed to keep working through it. She had intentionally picked a restaurant nearby in part I think so that neither of us had a retreat, and each of us were at the mercy of a timeline. Once we were seated, there was enough routine to distract, but not enough to interfere. At first it was manageable. It was a lot of questions about us growing up, and really a lot of questions about when I became sexually active (she had guessed it right), the sorts of girls I was attracted to (physically, emotionally), whether I'd been with a guy before (she was the first person I ever knew so closely that I shared that with) a litany of questions about pornography, and sexual interests that I may have that veered outside the normal bounds and whether my sex life with my wife was 100% satisfying, I didn't ask a thing. I didn't want to know, but I also thought I knew. All I could do was answer. Order. Wait. Answer. Eat. Wait. Answer. A part of me hoped that I would wear her out. That she would run out of questions and by the sheer power of honesty and openness, I could somehow get out of this without her wondering about, well, us. The bill arrived, she paid on our behalf and we were about to leave. "Just one last question, Sean. Maybe two." "Sure." "Have you ever masturbated thinking about being with me?" I didn't have to answer. I wasn't expecting that question, so I had made the mistake of letting down my guard and looking her in the eye when she asked. She would have watched my face flush as my lips quivered. My entire body said yes. And I got hard. I didn't have to answer but I did. "Yes." "That just made me a little wet, Sean." She went to get up, but hesitated in the process. The effect was to have her half leaning over the table, even closer to me than before. "When did you last cum thinking of me, Sean?" "This afternoon." She stood beside me and offered her hand to help me up. If she had looked she would have known. If she looked I didn't know. She led me, arm-in-arm out of the restaurant and hailed a cab. Inside she sat close to me. She gave her address, the driver started the fare and we were on our way. "Can I tell you something, Sean? It isn't as much a question as it will seem." I nodded. She leaned towards me. "Is it wrong that the panties you've made so wet, are the ones you came in while thinking of me?" She didn't need to say that. I knew back at the restaurant that we had our moment. By the time we got in the cab, everything else was just noise. She knew. I knew. Something was going to happen, and I thought I was ready.