A New Spin on Role Playing Games

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CD plays damsel for a live RPG and becomes a sissy slut.
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Part 1 of the 4 part series

Updated 06/15/2023
Created 12/11/2012
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I've always been something of a geek. I love sci-fi and fantasy books and movies; I can recite countless bits of useless trivia back to you about all kinds of movies. So, it was no real surprise that I took to role-playing games, or RPGs, as we like to call them. You know the kinds, Dungeons and Whatnots, all that kind of Tolkien-esque stuff. I had a couple of groups that I games with in high school, and it was fun, but it was never anything too serious or crazy. No, that waited until I got to college.

It took a little while to find out that there were other gamers at school. I think most of us had learned to hide being an RPG geek since that was usually a pretty good way to kill any chance of getting a girlfriend, or at least limit your hooking up options. But there were several groups, and I made my way around to them, trying to find a group I liked. I just never seemed to gel properly gel with any of the groups, but I did have some fun gaming sessions, and even made a couple friends. In fact, it was one of these friends, Roy, who first alerted me to some of the gaming groups that were off-campus. Since we were at a big state school, it was a pretty heavy party school, and big on athletics. So a lot of the hardcore nerds stuck to being off campus.

I found there were a number of groups that were associated with the big hobby shop right at the edge of town. The big problem was that they tended to be very private, and didn't really like taking on fresh blood. Roy suggested trying out LARPing, to see if that could help me work into some of the private groups.

"What the hell is a LARP?" I asked, Roy thinking he was messing with me.

"Live Action Role Playing," he responded matter of factly. "It's playing out some of the RPGs, but in real time, and with our actual selves as the characters."

"Live action? Seriously?" I shook my head. "Gaming isn't nerdy enough, we had to find a way to make it worse?"

Roy laughed, "You'd be surprised, it's usually a lot of fun, and most of the private groups like to join in, so maybe it would be a way to work your way into one of those groups."

"I guess I could at least come check it out, and if I don't like it, I can always just bail," I reasoned.

So, I showed up to check out the next time they LARPed, and it was about as stupid as it sounds. Everyone showed up in old robes, pointy hats, cardboard armor that had been painted gray and they all had cardboard swords and axes. They all seemed to have a pretty good time, though after a while it was hard to tell who the good guys were and who the bad guys were. It seemed to degenerate into total chaos toward the end. Afterwards, one of the guys who organized the things, Greg talked with me about it. He told me that had a couple different scenarios they would play out in a session. Today's was known as "Battlefield", but they also had actual missions they'd play, too. There was one called "Buried Treasure", where one team hid a treasure, then gave the other team a map, and they had to find it. There was also "Capture" which was basically capture the flag, but done in swords and sorcerers' style, instead of with paintballs. By far, the favorite was "Rescue", where the bad guys would "capture" a girl, or a maiden, as the case might be, and the good guys would have to find her and battle the bad guys to rescue her.

The only problem was, no one wanted to play the maiden, since they all wanted to be in the game. Greg explained to me, "So, we rotate the duty around, so no one person has to do it every time. I just want to warn you, if you're interested in playing, you'll probably get the duty as maiden, since it always falls to the newbies first."

Outwardly, I hoped I looked calm and normal, because inwardly, I was turning cartwheels. You see, hiding who I am as a geek has never been hard, I've been doing it for years, because I'm also a closet cross dresser. So, to have the chance to dress and be out and about doing it was a thrill. My only major concern was that I usually get pretty turned on when I dress, so I'd have to figure out some way to hide that. I briefly wondered if it would be weird if I volunteered to be the maiden EVERY TIME?!

"Okay, yeah I get it, that's fine, I mean everybody has to go, right?" I tried to sound nonchalant, but hoped my excitement wasn't creeping in.

As it turned out, the games were decided exactly the way you'd expect, by rolling the dice. There were several scenarios, so to make sure it was fair, they rolled the dice to pick the next session. The next scene was for Battlefield, which was good, since I'd already seen that. So, I came out the next time, decked out in my cardboard armor. I do have to admit, I felt pretty stupid in the armor, but then it occurred to me, I'd probably feel weirder if I were dressed as a damsel in distress. So, I figured the armor would let me get over looking silly in public to start. It was fun, it was kind of stupid, but it was fun. Oddly, I was a little disappointed that the next was Capture, but I just settled in and enjoyed the gaming. The next time they rolled and it came up as Rescue. I was thrilled, but I still tried to play it off, I didn't want to look too excited.

Greg came up afterwards, "So, you heard it was Rescue?"

I nodded, "Yup, I heard."

"So, you're still cool with being the damsel?" he sounded a bit worried.

"Yeah, no it's cool, I'll still do it," I went along.

"Okay, great. Let me introduce you to Henry. Henry has a bunch of sisters, so they have a bunch of clothes we can use pretty much as much as we want," Greg explained.

Turned out Henry's four sisters had a whole attic full of clothes, and since only one of them still lived at the house, they generally didn't care what happened to them. "They all went through a variety of looks over the years, so we can generally get something that'll fit most of the 'damsels' and still have a princess or something similar look. There are also old Halloween costumes and such, so we can get whatever. Stop by my house at noon."

"Why so early? The session doesn't start until 3?"

"True, but we'll have to find something that fits you, get you make-up, and find a wig, all that stuff."

"There's going to be all that?"

"Don't worry my sister will help you get everything. She complains about it, but I think she kinda likes it.

I found myself that night sitting in my room, wearing what little feminine clothing I had of my own, wondering what they'd have for me to wear. I lounged in my thong, bra, stockings and my 3" pumps, hoping there'd be some stockings and maybe some nice panties. Some heels would be lovely. I wasn't sure if I wanted it to be long and feminine and pretty, or if I'd rather go with short, sassy and sexy. Either way, I was sure I was going to enjoy every minute of it. I rubbed my clitty through my panties and pulled out my favorite toy, a nice thick 8" long dildo. I used my tongue all over that pretend cock, imagining it was my heroic prince who had rescued me and was now receiving his just rewards. As I lubed my lover up, I continued toying with myself, sliding the phallus deep into my ass, moaning softly, wanting to be taken and used. As I fucked my hole, I stroked my clitty in time until I shot a powerful load, moaning and groaning as I slowly milked my lover with my ass. I couldn't wait until the next session!

So, around noon the day of the next LARP, I found myself outside Henry's house, my heart beating a mile a minute as I rang the bell. Henry was eating a sandwich as he came to the door. "Hey, come on in. You want something to eat?"

"No, thanks," I replied, "I already ate before I came over." That was technically true, but I was so nervous and excited, I just ate some light snacks. I didn't want to throw up! That wouldn't be very lady-like, now would it?

"Okay, well let me go get Nora, she'll show you where everything is," he led me up the stairs. He yelled for his sister, "Nora?"

"Yeah, is lunch ready?" she popped her head over the banister. "Oh, hey sorry." She smiled down at me. "Oh, is this..." she trailed off.

"The next damsel, yeah," Henry smiled and shook his head. "I'll bring your lunch up, while you show him around."

"Sure thing, come on up," she waved to me. I tried not to run as I went up the steps. She gave a long look up and down as I stood in front of her. "Well, Henry didn't mention that you're cute, so that'll be a nice change. Some of the guys they've had, just ugh. So, you're also a good size, of course, we've got a lot of clothes. Part of the reason Henry always volunteers our attic for this stuff. How tall are you?"

"Uh, about 5' 6", or so", the question took me a bit by surprise.

"And what do you weigh, about 125?" I nodded as an answer. "Great, let's go see what we can find." She turned and headed through a doorway and up a small flight of curving stairs. "Watch your step," she called down.

I could see why, the steps were really narrow. We came up into the attic, and she wasn't kidding! They had a ton of clothes up here. Some were on hangers and racks, some were in piles and bags. There were shoes and skirts and blouses and dresses all over the place. I had died and gone to cross dresser heaven!

"Don't mind the mess," she laughed. "I guess this is the other reason we get picked for this. We've got enough clothes to cover a small army. So, anything in particular you want to wear?"

I shrugged, "I wouldn't even know where to start."

"I think I do," she mused, then dug into a pile of clothes. She pointed to a small chest, "Look in there and see if you can find some stockings."

I turned a little hesitantly and opened the trunk. There were a ton of clothes in here, mostly panties and stockings. I dug around until I found two stockings that were a match. "How about these?"

"Those should work," she held up a red number with a lot of laces. "And I think this will work perfectly."

"What is that?" I asked.

"A corset," she replied, still looking around through the piles. "I think I have a great idea for you. Oh, go ahead and get undressed." She continued digging around in the clothes.

"Right here?" I asked.

"Sure, why not? You shy?" she raised an eyebrow at me.

I blushed a bit, though I'm not sure why, "No, I just didn't want you to..."

"Don't worry about me, I like the challenge of trying to pretty you boys up. You should be even more fun. I think you'll be surprised how it works out," she sounded pretty sure of herself.

I nodded absentmindedly as I took off my shirt and slipped off my shoes and jeans. I stood in my underwear and wondered if I was supposed to go all the way. I figured in for a penny... I pulled a nice pair of panties out of the chest, they looked a little small. I grabbed another pair, but these didn't look quite right.

"Go for the red pair off to the side," Nora said without really looking.

I grabbed them and pulled them on. Wow! They were awesome. It's a good thing I was pretty nervous, or I probably would have put a tent in them right away. As it was I decided to tuck my clitty down before it really gave me away.

"Go ahead and put the stockings on," Nora said briefly glancing at me. I rolled them up into little balls to get started. "First, you roll them up into little balls and, oh..." she saw I was already pulling them up my legs. "I guess you already know that, here's a garter belt to hold them up." She tossed another red number to me. I wrapped the garter belt around my waist. She came over and showed me how to hook the garter tabs to the stocking tops. "And make sure you put the tabs under your panties, otherwise you have to undo everything if you need to go to the bathroom... or anything."

I nodded as I hooked on the tabs to the stocking tops. Yup, it was a good thing I tucked, or I'd be starting to rise up now. I was already getting uncomfortable, mostly because of being tucked away and my clitty trying to rise up. Nora had me stand and she wrapped the corset around my waist, she tightened it a bit then started pulling on the laces. "Whoa!" I gasped as the sides squished me in.

"Don't worry, I won't tighten it too much. We still want you to be able to breathe," she stated. "At least for now." She yanked on the laces a bit more and tightened them off.

"Now these will help give you a little more... definition," she pushed two flesh colored objects into the front cups of the corset.

"What are those?" I asked, still a little out of breath.

"Those are falsies, they'll make it look like you've got boobs," she stated simply.

"I'm not sure that's really necessary, and why do you have those anyway?" I wondered aloud.

"Some of my sisters would go for the giant boob look for Halloween. I have no idea why," she shook her head. She handed a black skirt over to me. I pulled it up while she kept digging around. The skirt was about mid-thigh, a nice length, but still showed some leg. It was a bit flouncy, almost like a school girl type skirt.

"Now, since you're mostly going to be in the woods and whatnot, we don't really want spike heels, so we have some nice wedges, that should still give it a nice look, but not have you sinking into the ground each step," she explained. "And the topper," she said picking up a long flowing blonde wig, "you get to be a blonde!"

I was giddy inside, but I still wanted to keep up my front, "Look, I don't know that all this..."

She pulled the wig down over my head and began settling it in. She pulled out a hairbrush and brushed it out a bit. As she did, she leaned down close to me, "You can stop pretending, I know you're enjoying this, so just enjoy it. It doesn't bother me, and you don't have to try and be all macho on my account." She went back to brushing out the wig.

"Is it that obvious?" I asked hesitantly.

"Well, the tent pole in your panties is a good giveaway, but also, most of the guys keep their boxers on. You went right for the panties without being told, so I took that as a sign. Plus you knew right away what to do with the stockings. Do you shave? You have almost no body hair," she finished with the wig.

"A little, but not much, I just mostly have really fine hair," I admitted.

"Well, you're lucky, shaving and waxing all the time gets to be a pain in the ass, literally sometimes," she laughed. Then she handed me a pair of black, wedge sandals. "Put these on while I get some make-up. Since it's out in the woods, we don't need a lot, just some basics, but we still want you to look nice."

"Hey Nora, your sandwich is ready!" Henry called from the hallway.

"Be right back," she smiled and headed out.

I seriously considered jerking off real quick, but I wasn't sure how long I had, and I didn't want to get caught. Also, I briefly wondered where I could finish off without leaving a mess. Visions of "There's Something About Mary" went through my head. I laughed and put the sandals on. They were a middle heel, probably less than 4 inches, but still a bit higher than mine were. I stood and tried, and was able to balance pretty well. The wedges did give more support than my stilettos.

Nora returned a few moments later carrying a small case and a plate with a sandwich. "No problems then?" she asked coyly.

I shook my head and took a few steps to demonstrate. She stepped closer, "You have done this before, haven't you?"

I just smiled and shrugged and let that be my answer. She shook her head and pulled out some make-up from her kit. She put some foundation, powder, eye shadow, mascara and to top it off, bright red lipstick. "I thought you were doing some light make-up?"

"This is light, believe me, if I go heavy you'll have painted nails to match!" she grinned.

"Well, in for a penny..." I smiled.

She raised an eyebrow, I just shrugged. "Okay, you asked for it," she pulled out some nail polish in bright red and showed me how to put it on the first nail, then had me practice on a few. "Okay, let that one dry and I'll get the other." She finished painting the nails, then ate her sandwich while she worked on my face a little more. Once she was done, she smiled and looked me up and down. "One last touch," then she went to a jewelry case and came back with a gold necklace and bracelet. She put them on me and looked quite pleased. "Want to see?" she asked.

I nodded, afraid to speak. We went over to the mirror and I looked pretty good. Not beautiful, but cute and sexy. Maybe a little overdone, but I was in costume after all! With the corset and the stockings and skirt, I looked a bit like a serving wench or something like that. I was shocked though, I did make a pretty hot girl. "Wow," was the only thing I could come up with.

"Yeah, I outdid myself this time," she grinned. "They're not gonna know what to do with you!"

Nora went down the stairs and called for Henry. I came down the steps and made my grand entrance. Henry looked a little confused at first. "Wait, where's... holy shit, really?" Nora just smiled and nodded, obviously quite pleased with herself. Henry just shook his head, "You almost ready to go then?" he asked.

"I guess so," I shrugged. "A little late to back out now."

So, we headed down to the area where the LARP was taking place. As I got out of the car, I could feel all the eyes turn towards me. There were a lot of whispers and I started to get a bit nervous. Then there were a few cat calls and a couple of wolf whistles. That actually helped me settle down. They weren't getting mad, I think they were just confused. Greg even came up, "Henry, I didn't know you got a girlfriend!"

"Hardee-fucking-har-har," Henry deadpanned.

"Seriously though, you look... good," Greg said to me. "Certainly the best looking damsel we've ever had. Your sister is getting good."

"Don't tell her that, she's already super proud of herself this time," Henry stated.

Greg laughed, then added, "I can see why," giving me an appraising look. I'm not sure why but I got a little twinge from that and felt my clitty trying to rise up again. I was already starting to get turned on from being dressed, and being found so sexy was just upping that.

Greg then called the group together, went over the rules and then divided up the teams. I was given over to Scott, who was the evil wizard, and would be leading the team that was holding me captive. We all headed off to plan strategy and get set-up. Scott spent several minutes getting everyone their jobs and then we headed off with a small group to the lair. As we walked, Scott started in on some conversation with me. "So, you're still pretty new to the group, huh?"

"Yeah," I replied, "I've just been to a couple sessions."

"They usually rope the newbies in to be the next damsel, though I do have to say, you're the best looking one we've ever had."

"Thanks, I guess," still trying to sound unexcited. I briefly wondered if anyone was buying it.

"So, here I'll have to blindfold you," Scott stated like it was nothing.

I stopped, "Wait, what? Why?"

"Well, we can't have you giving away our position to the enemy now can we?" he stated, his voice taking on a slight inflection. He sounded like he was getting into character.

"It's fine, I won't say anything. I don't even know where we are," I was a little scared.

"Of course, I'll just trust you," he sneered evilly. "I don't think so." He pulled my hands behind my back and then tied them together quickly. I was so shocked I didn't even think to fight back until he was slipping a blindfold on me.

"Really, look, this isn't..." I started, but he cut me off.

"Oh, but it is, my dear," he whispered in my ear, "Now quiet, or I'll have to gag you, too. In fact, I might anyway," he laughed evilly.

I wasn't sure what to do now, but I figured I'd just play along for now, trying to stagger my way through the woods with my hands tied and with a blindfold on was a little scary, yet I was also getting excited again. Thankfully I was tucked extra well, otherwise I would have a rather un-ladylike bulge!

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