Not Careful Enough Ch. 01

Do you know what is the worst thing about being super careful about keeping your secret life a secret? It's that when you forget you dont realize you've forgotten because you are used to being so absolutely careful all the time. That's what happened to me and this is what happened.

When I went to college I decided to go to a regional campus, to keep the costs down, and stayed with my parents, instead of living in the dorms. It wasn't as bad as you might think. My parents are hardly home except for the weekends. So most of the week I have the whole house to myself. Imagine what a college age boy would do with a whole house to himself and a flexible school schedule.

I watched a lot of porn! I love porn. I see it as, like, the best reality show around. Ive had sex before of course and i know the difference between porn and sex. My high school girlfriend went to a school out of state so we decided to break up and remain friends. So all I had left was porn anyways. It's not like jerking off all day every day but I would have porn running in the background while doing something else. I got really good at searching for exactly the right porn I wanted.

What people don't talk about though is that there is a porn rabbit hole you can go down. First you like "stuck" porn, where the girl gets stuck and someone takes advantage of the situation, then you take one more step from that and go to "oops anal" porn then maybe "anal punishment" then mix in some "bondage" until at some point you come to "straight girl gets surprise anal punishment from big shemale cock". That is a rabbit hole!

I really liked the taboo, "no please. We shouldn't. This is so wrong." and quite organically i really started to get into shemale and pegging porn and domination/humiliation narratives. I was always careful. I had everything saved on a separate harddrive that I could hide quickly and easily. I stayed in "incognito" mode so that I could quickly close out of everything in one keystroke and nothing would be saved. My phone was always locked and I saved everything in the trash bin so it wouldn't just show up if I was scrolling through things with someone looking over my shoulder.

One of things I really started to get into was I liked to get dressed in some lingerie or panties or stockings or all of the above. I had some outfits leftover from my ex-girlfriend. I had those hidden deep in my closet in case someone got nosey in my room.

Like I said, I was careful. I was a secret agent. Until...

One weekend my dad was on leave, he's a marine, and my mom was away at some corporate retreat, she's an accountant or something. Well my dad brought with him a buddy who recently got stationed here. Anyone who knows marines knows they basically all look the same. Big arms, big shoulders, and no neck and this guy was no different.

"Mark," my dad called me, "this is Jerry, he needs to use your computer to check his moving Pod."

"Uh yeah sure dad, come on Jerry it's in my room." I waved him on to follow me up to my room.

As we scaled the stairs i was running through the checklist:

Everything was closed out

Flash Drive was pulled out

Lingerie was boxed up

Cumrags were trashed

Etc etc etc

When I got to my room I darted my eyes across the room and confirmed my checklist. I showed Jerry my computer and logged in and pulled the chair out so he could sit down. It felt awkward to just stand there while he used my computer so I just left him and returned downstairs.

When I got downstairs my dad was firing up the grill and getting dinner prepared, his favorite, charred meat and beer, no greens. I didn't mind that he was a good grill master. Not having anything to contribute, I went to the living room and plopped down on the cough and turned on the TV. I mostly flipped the channels. It took some time but at some point I realized I didn't have my phone on me. I tried to think where I had it last.

Last thing I remember, I was in my room surfing porn all alone. I ran down the rabbit hole again, got sexy and tried on some sexy clothes, took some pictures. I like to feel pretty so sue me. Then i.....don't remember when I did. I heard the door open so I closed down my computer and put the box away. I didn't have time to take off the pink lace panties so I just slipped on some sweats and a t-shirt.

Then it hit me. My phone was still in my room and probably still in camera mode. That meant my phone was unlocked and alone with Jerry. I quickly shot up and ran up to my room. I had left the door open and tried not to look suspicious as I entered my room. My eyes were darting back and forth looking for my phone.

"How's it going Jerry? Find what you were looking for?`` I asked him.

I was hoping to sound casual, not panicky as I searched for my phone. I thought it would have been on my bed but it wasn't there. I looked on the floor and it wasn't there either.

"Yeah looks like it's delayed one state over so it doesn't look like I'll get my stuff for a couple more days still."

"Oh man that sucks." I said, barely paying attention.

"What uh, what are you looking for?"

"Hmm? Oh nothing, I just can't find my phone. Dont you just hate that?" still trying to sound casual.

"Oh yeah you mean this phone?" he held up my phone, the screen black.

My heart leapt when I saw it in his hand. I stared at his face for any kind of indication that he might have seen anything on it but like a damn marine he was unreadable.

"Yeah thanks brah. Where uh where was it?" I asked cooly but internally freaking out.

"It was just sitting right here." he pointed to the desk where i left it propped up to take pictures.

"Right of course duh. Silly me. Thanks." I said reaching out for my phone.

Jerry pulled it back towards himself and I stared at him confused.

"You know pink really is a nice color for you." he said, smirking at me.

I saw him tilt his head to look at my butt. I froze at his words. He knew! He saw at least the picture of the pink lace panties I have on right at this moment.

"I uh i don't know what you mean.'' I stammered and pulled my hoodie down.

"Oh I think you do. Is this what you do all day when you are alone? You dress up all cute and sexy and take pictures of yourself? Are they for anyone specific?"

I held my down not daring to look him in the eyes. I didn't know what to say. I've never been caught before. I'm always so careful.

"Answer me. Do you take pictures for someone?"

I shook my head.

"Good. I took the liberty of sending some of your pictures to my phone. It really is a shame that you didn't have the forethought to not include your face in some of those."

My head jerked up and was astonished by what he told me. What was he going to do with those pictures??

"What do you want with those?"

"Well in the broad sense they will serve me well tonight when i'm all alone." he winked at me, "but right now i think i want to see what you got on right now."

"What? But I'm not wearing anything!" i lied hoping i didn't have to further humiliate myself

"Cut the crap I know you are wearing a pair of pink panties right now. You didn't have time to take them off when your dad and I got here. So turn around and let me see. A picture just isn't the same."

I fidgeted with my sweats, unable to bring myself to expose myself.

"Look, you can either show me right now or I can show some of these pictures to your dad right now. It's your choice."

I sighed and turned around and lowered my sweatpants just enough to show my whole ass wrapped in girly pink panties.

"Oh yeah that will do nicely." I heard him say.

I turned my head to look over my shoulder at him and was shocked to see his phone pointing at me. I quickly stood up and pulled my pants up.

"What the hell!" I said.

He turned his phone around and showed me the picture where it looked like I was basically presenting my ass to him. Now he really had me over a barrel, so to speak.

"You gotta delete that..." I started to say.

"No, I don't think I do. I do think that if you don't want your dad to find out that you are trying to seduce his subordinate then you better do what I tell you."

There it was. He was going to blackmail me.

"What do you want to do?"

"Well firstly I think we should go downstairs and eat. I'm starving. As for later, I'll be in touch."

He stood up as he was talking and when he said the last he reached a hand down to pinch my bottom. It made me jump and he laughed at my reaction.

"Oh this is going to be fun." he said as he left my room.

At dinner Jerry insisted on sitting right next to me. My dad had grilled up some brats and burgers. At every opportunity that my dad wasn't looking, Jerry would put his hand on my thigh. I would push him off but he would keep touching me. It wasn't until my dad went to clean up the grill outside that he got really daring.

He held up a brat to me with no bun.

"You know what is great about brats? They look so phallic." he handed it out to me to take it.

Tentatively i took it in my hand and just looked from it to him not knowing what he wanted me to do.

"Well go on, show me what you can do with phallic things."

"I uh i don't do anything.'' I stammered awkwardly.

"Oh really? Well how about you start by putting it in your mouth so i can see what you look like with a dick in your mouth."

I stared at the brat in my hand and Jerry lifted my hand to bring it to my mouth. Now I have already eaten two brats tonight but now this feels dirty. I opened my mouth and put it in my mouth, wrapping my lips around it like a popsicle.

"That's good. Now suck it." Jerry commanded.

I felt so dirty. I started to do what he told me and sucked it as I pulled it out. I just told myself to do what you do with a popsicle and I sucked it a couple of times.

"That's not bad. You are going to need some training but that's not a bad first start."

I immediately stopped when I heard the back door open. I put the brat down on the plate and wiped my greasy lips.

"Mark, how about you show Jerry to the living while I clean up. Find something to watch until I'm done."

"Uh yeah sure dad."

I said getting up and walking to the living room. I could feel Jerry staring at me as he followed me. When we got to the living room I grabbed the remote and sat down on the couch and of course Jerry sat down right next to me. I tried to ignore him and turned the TV on and flipped through the channels.

"What uh do you want to watch?" I asked, my voice shaking.

Jerry didn't answer but instead grabbed my free hand and put it on his crotch. I felt something hard and warm and thick. When my brain registered what I was feeling I drew my hand back quickly.

"How long do you think we have before your dad is done?"

I didn't want to answer. I knew my dad and when he cleaned up everything was spotless and back in order. I was cursing his marine precision now. I didn't have to answer, I just averted my eyes and shied away. Jerry took that as an opportunity to scoot closer and wrap an arm around me. With his free hand he unzipped his pants and fished out a massive, veiny, dick. I couldn't help myself but just stare at it dumbfounded. I'd never seen a dick that big before. It was incredible.

I realized my mouth was open when I heard him laugh and I kind of snapped out of my mesmerization.

"What's the matter? Never seen a dick this big before?"

I shook my head and stared at the TV. It was playing on the news. I felt something drop across my lap and found the blanket that sits on the side of the couch across both of our laps. Jerry folded it over so his dick was standing free and open.

"Come on baby, I know you want to touch it."

I tried to shrink into myself as much as possible. I couldn't stop staring at it. How was it so big? I felt his arm tighten around me and with his other hand he reached across to grab my hand. He moved so slowly and gently that I didn't even know what to do. Then he raised my hand and pulled it to his pulsing dick. I wrapped my fingers around it. It was so warm and soft. My fingers didn't even touch because it was so big.

"See that's not so bad is it?" he whispered in my ear.

I shook my head. It was super awkward and my heart was racing but it wasn't as bad as I thought it would be. It was strange as he guided my hand up and down and I was stroking him. I could feel the skin sliding over the rigid core of his cock. It was quite incredible.

"That feels so good baby. Keep stroking it. You can squeeze it harder, you're not going to hurt it."

I did what he said and squeezed his cock firmer and maybe stroked him a little faster.

"How about you show me what else you have on that phone."

With my other hand I pulled out my phone and unlocked it. I opened photos and scrolled through my selfies of me dressed in various lingerie.

"Oh baby you look so hot in those. Where did you get all those?" Jerry asked.

"They were my ex girlfriends. She left them and I got curious."

"What made you curious about dressing like a girl?"

I debated on showing him the kind of porn I had on my phone but I was already stroking his cock right there in the living room. How much worse could it possibly get?

I opened up a folder of video clips and caption porn. One slim, feminine looking guy, also like me, dressed in a lace corset and a pink chastity cage getting railed up the ass by a big thick hard cock. The caption read:

"Dress like a girl get fucked like a girl."

"Is that something you want?"

I quickly shook my head and put the phone away.

"Of course not. Im not gay.'' I said ignoring the fact I was still stroking another man's cock.

"I didn't say you were but real men don't wear pink frilly panties and jerk off another man."

That snapped me out of it and I pulled my hand away from his hard cock. He grabbed my hand and pulled it back to continue stroking him.

"I didn't say stop. Let me tell you how this is going to go. You do what I tell you or I will show you dad what a sissy little girl you are. Do you want me to do that?"

I continued to stroke him as he spoke. I was trying not to cry and really feel like a girl.

"Answer me." he growled in a low voice.

"No." I said frog in my throat.

"No, what?"

"No sir." I said obediently.

"That's better. You can stop now. We wouldn't want your dad to walk in and catch you jerking me off."

I pulled my hand back and he tucked himself in his pants. He was still bulging noticeably but he covered himself with the blanket. I continued to flip the channel and he released his arm from my shoulder. I immediately put some distance from us and settled the TV on some cop show. We just watched the show in silence until we heard my dad walk in and he excused me so he and Jerry could "talk shop".

I tried not to seem too eager as I stood up and walked to my room. Once I was alone I really started to panic. How could i have been so stupid?! Leaving my phone open, how stupid was i? What was I going to do? What could I do? What was Jerry going to make me do? Why was his dick so massively huge?

I sat down on my bed and turned on my TV and just put that cop show back on and tried to forget everything that just happened. At some point I heard the front door open and then close. I looked out the window and saw Jerry leaving. Then he turned and looked right up to my window and I quickly ducked away so he wouldnt see me, at least I hoped he didn't.

I walked down stairs and found my dad still on the couch but watching the news.

"So uh what's the deal with Jerry?"

"Hmm? Oh he just transferred out here and he is under my command. He's supposed to be a resourceful guy so we will see how he turns out. So how's school going?"

I sat down and told him about school. I wasn't an A student but I was a good C or B student. I told him about some fun stuff that was going on at campus. Just chit chat. Then I got a message and looked at it while talking and I lost my train of thought.

It was a message from Jerry. He sent me a picture of his hard cock in his hand and then that picture of me presenting my ass in my pink panties that I was still wearing, for some reason. The text read:

"Show me that tight little ass of yours."

"I uh, I gotta go dad. I got some school work to finish up on." I told dad while I hid my phone as best I could.

I practically ran up the stairs and into my room and locked the door. I never played when either of my parents were home. My heart was racing again and now my hands were shaking.

"Why are you doing this?" I texted Jerry back.

"I have my reasons. Now pull those panties down and show me that ass."

I held my phone just staring at it tapping my leg with my other hand. I knew this was a mistake but what choice did I have?

I pulled my pants and panties down and turned the camera on and reached around to line it up with my butt and snapped a picture and sent it to him. I pulled up my pants and watched the image load and then finally sent.

I nearly leapt when my phone chimed and I saw the message from jerry.

"No. Put the phone down, bend over and spread your cheeks."

I sighed, exasperated. I got on the floor and propped my phone on the edge of my bed and set a timer for the camera and turned around and pulled my pants and panties down over my butt and rested my face on the soft carpet and reached back with both hands and spread my butt cheeks. I waited for the camera to click and it felt like eternity.

What was I doing? This is so degrading.

*click*

I raised up and pulled my clothes up and grabbed my phone. I waited for the next shoe to drop.

"That's a good girl. I'm sending you a link. I want you to watch it tonight. Tomorrow I will have a package dropped off. Let me know when you get it." Jerry texted.

"What kind of package?"

"You see."

He then sent a link. It didn't have a specific web address so I was confused about what it could be. I tapped the link and it brought up a video that was full screen on my phone. It was black until colorful swirls spiraled in a mesmerizing array of colors and movements. A feminine voice spoke and I had to adjust my volume.

"You are a sissy girl. You like being a sissy girl. You like serving big alpha men."

The spirals overlaid flashing images of sexy women and close ups of big hard cocks and clips of women and shemales getting fucked in the ass by big cocks.

"You are a sissy girl. You like being a sissy girl. You like serving big alpha cocks."

I tried to get out of it but it didn't respond. Until I turned off the screen and went back through the lock screen.

I sent a text to Jerry, "what the hell is this?"

"Like you dont know porn when you see it."

"No, that's not what I meant."

"It is just some encouragement. Watch it tonight. With headphones. And if you can manage it. Dont touch yourself."

"That won't be hard."

He then sent another picture of his dick in his hand.

"Speak for yourself."

I rolled my eyes and put my phone down. I tried to ignore my phone and get on my computer and play some video games. I found it difficult to focus on the game and really wanted to watch porn. It was getting late so I turned off my computer and crawled into bed.

Looking through my phone I scrolled through my porn collection. And because I have a cat -like curiosity I pulled up the message from Jerry. I opened the link again and the spiraling colors started up. This time I had my headphones in and when the female voice spoke it was like she was in my head not in my ears.

"You are a sissy girl. You like being a sissy girl. You like serving big alpha men."

Then the porn overlaid the spirals. The closer I looked the more I was noticing that the picture that was flashing was of big hard cocks.

" You are a sissy girl. You like being a sissy girl. You like serving big alpha cocks." The female voice spoke.