Caroline Finds Out Pt 01

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.