10. I don't think I really have a specific fantasy or direction like I think you'd like me to answer. I read a lot of stories on Literotica and any given story will strike me and arouse me. When I analyze it, why or what it is that turns me on, I really think it's that I'm outside of it, like a voyeur. So, I guess if you had to put a name on it, voyeurism.
I read a story and I am watching the characters as an outside observer. I pay attention to the feelings and thoughts the characters have. I'm not putting myself in any particular point of view, not like if a woman is getting fucked or having her pussy played with, I don't feel like I'm her, I'm looking for her reactions or how he reacts and how they feel and what they think. I imagine I'm watching and they know I'm in the room with them. I don't want to participate and I don't want them to focus on me, I just want to watch.
Maybe that's also part of it. Like I want to be watched. To be seen. To show someone, an outsider, my sexy side. I fantasize about masturbating and being watched. I don't think I could ever do it though, there would be a block in my head that wouldn't let me really relax and have fun. I fantasize that there is a man I would be comfortable enough that I could let go and give myself pleasure while he watched me. Just me on my bed, naked with my magic wand, legs spread, touching myself, squeezing my breasts, pinching my nipples, pressing the wand head wherever it feels good, and him sitting in a comfortable chair stroking himself to my performance. He would talk to me, tell me how sexy I am, what a beautiful woman I am, compliment my body and describe how it feels to watch me.
That's just one. I'm not so selfish that I only derive pleasure that impacts me, I also fantasize about pleasing my partner. I fantasize about giving myself up to his urges and knowing that my body is making him feel good. I imagine how it feels for him when he slides himself inside my warm wet pussy and when he presses himself completely inside me and our bodies are making total contact, stomach on stomach, chest against chest, his balls pressing against my ass, my thighs wrapped around his torso and pulling him toward me and him pressing against me. I want to feel as if the only thing he wants to go deeper inside me for me to swallow his body and mind.
I don't have fantasies the way you seem to have. I hope that's not a disappointment. But, since we've been writing and sharing our stories, I have kind of developed a curiosity. I sometimes imagine what it would be like to go lingerie shopping with you. We would spend the day shopping for shoes, panties, makeup, and other feminine curios; we'd have lunch together, maybe a cocktail or two, and then go to a nice hotel. We would spend hours playing. You would bathe me, shave me, wash my hair. I would show you how to do everything and we would play with each other, touch each other, tease each other. We would drink chardonnay and lay on the big bed watching TV. Both of us clean and smooth naked in bed kissing and touching, talking and laughing. I would show you how I like to be touched and you would show me. We would ask questions to find out how and why we like it, describe everything to one another, make our conversation and our play one-and-the-same.
We would try on outfits. Model for each other while touching and teasing, kissing and licking. I would give you a makeup tutorial and we would laugh and talk about it. I would show you tricks and tips to improve your skills. We would paint each other's nails and toes. We would dress up for the theatre and go to a show, a musical, or a play, something to make us feel special. You would wear stockings and a garter belt, a pair of silky panties, and a chemise under your sportcoat and slacks. I would wear a sexy dress that shows off my breasts, hips, and ass. I'd wear open-toed heels with lots of leather straps. We would have dinner in our room dressed up in our evening wear. We would play under the table with our toes, hold hands across the table-top, lean across to one another and kiss each other.
We'd walk from our hotel to the theatre holding hands and talking about the show. We'd read some reviews on our phones and wonder aloud about how this performance will be, talk about the story and the director, talk about other shows we've seen and what we liked and didn't like. We'd get to the theatre early to have a drink and walk around the lobby looking at the architecture and talking about the art on the walls while sipping champagne. You would look at me with desire in your eyes, rub my ass through my dress playfully, kiss my neck and behind my ears. We'd smile and laugh and lean into one another as new lovers do. I'd pull up the waistband of your panties so if you opened your jacket or turned your body in a certain way if anyone was looking they'd notice your panties.
We'd take our seats, good seats, and when you sat, your slacks would ride up and expose your hose at your ankles. When the lights dimmed our hands and fingers would find each other and places on each other's bodies. We would be discrete and casual, not drawing attention to ourselves, but feeling each other just enough to want more, but we would restrain ourselves to add to the tension, never giving too much to the other, but always something.
At intermission, you'd go to the bar and get us a drink and I would go to the ladies' room. I'd meet you on the terrace and you would be smoking a cigarette. I'd slip my wet and warm panties into the palm of your hand, "smell them," I'd say to you and you would discretely bring them to your nose and mouth and I would lean up and kiss your neck behind your ears and grab your ass.
We'd make our way to the railing of the terrace and you would casually stand behind me with your arms around my waist and we'd face the city skyline overlooking the railing and you would discreetly slip your hand down and press the thin fabric of my dress into my bare naked pussy and rub me, "act like I just said something funny," you'd whisper in my ear. I'd laugh out loud and act like you weren't rubbing my pussy. You would ask me about work or my master's program and we would talk about it as if it was the only thing that mattered and you'd slip your hand under my dress and slide a finger along my wet lips slowly up and down, up and down wetting the tip of your finger. All the way down, then slowly back up and my pussy would show you how wet she was. Then you would sidle up next to me removing your hand from beneath my dress and then paint your own lips with my cum. You take a drink of your whiskey and then kiss my mouth. I kiss you back and I can taste myself.
We would laugh at ourselves, cast quick glances around making sure no one was watching us. We'd relax and let the moment recede and the tension subside,gathering ourselves and letting ourselves decompress and return to society. We'd watch the rest of the show holding hands and caressing each other's fingers and palms, sliding our fingers up and down each other's forearms just touching one another to show the other we are interested and enjoy the show.
On our walk back to the hotel we would talk about the show, the theatre, the performances and we'd stop at the liquor store for a bottle of wine to have in our room.
I'll leave the rest up to your imagination: but that's just a passing idea I've been imagining...lol.
I sent him my responses. I was so aroused from writing my response to number 10 that I was wet. I hadn't planned on going that far, and honestly, most of that fantasy I made up as I was writing it, I'd never thought that deeply about it before. On the surface I'd imagined playing with Otto, putting on makeup together, but as I started writing, I remembered all the little things he'd told me and all the stuff from his Literotica stories, and I just started imagining more and more details of what a night with him would be like.
I still had no idea if he knew it was me who'd commented on his Literotica story. I hadn't told him I'd found his profile. He hadn't asked me about the comment. I don't know if he knew, and if I'm honest, because Otto can be oblivious at times, I was almost certain he didn't know I knew about his secret. Certainly he had revealed a lot to me in our Shared Doc and in his responses to my questions, but what he'd told me himself, and what his Literotica stories told me were still very different people.
This fascinated me. He still didn't trust me. My response to number 10, was somewhere in between what he'd revealed to me personally and what I'd found from reading his stories on Literotica. I hoped this would push him further.
I started to do some research into what it means to be a "sissy." Otto called himself this in his stories. The term popped up all the time. Maria or Jackie, the women Otto wrote about most in his stories were always calling him, "my pretty sissy," or "sissy panty boy," or "sissy cumslut."
I couldn't believe what I started to find out. Apparently, there is quite a market for sissies. And the spectrum of what a sissy is, is wide and diverse. I discerned Otto was somewhere in the middle. His early stories were mostly panty-based with some feminization and soft-core domination. I decided I need to know what level of a sissy he considered himself. But I needed him to confess. LOL. I know it sounds crazy and when I hear myself say it, it sounds even crazier, but I knew from reading about the topic, that he needed to admit to me everything if I was going to have total control over this man. I wanted to control him. I wanted to know everything about him and I wanted him to tell me.
I can relate to it because I have a bit of this in me. As I said, I'm a voyeur. Voyeurism is not just watching, like an eavesdropper, but it's the excitement of watching knowing the observed party knows they're being watched and enjoys it. So as a voyeurist, you also get off on the awareness that you are watching and being watched. Otto clearly wants to show me who he is, this much I know. I had to show him he could trust me.
I took the first step in sending him the story and then I sent him a recording of me masturbating while reading a story I liked. He'd begun letting his sissy side out on the page and in photos. I wasn't sure if he knew it was me who'd commented on his story on Literotica. He was replying to all of my PMs and DMs, emails and skype calls. He seemed to be a willing participant.
My definition of Sissy
A sissy imagines he/she is a woman. Not just a woman but a slut or whore, they refer to themselves as such, I'm not being judgemental. Sissies start off on their journey with panties, many, if not most, begin when they find their mother's panty drawer, this was the case of Otto, and almost every origin story I read online had this shared experience. It's either their mom's or their sister's panties that initiate their fetish.
I read many stories about men stealing panties from friends' houses, dirty laundry hampers, laundromats, locker rooms, and shoplifting from stores. Dirty panties are the holy grail for a sissy. They also buy panties online and when they embolden themselves shop for them at brick-and-mortar stores.
