Earning My Panties Ch. 01

I looked up at Mr Clarke, and took some stock of my current situation. The head of his cock was still in my mouth, and so too was his thick warm salty cum. This was my first time ever having a cock in my mouth, I had never until very recently ever even thought I'd want something like this to ever happen to me, but I now also knew for certain that I was going to do this again, and more.

I'd like to share with you the 72 hours that preceded this profound change in my sexual life.

I was your typical 19 year old college student, I'd enjoyed my first year in college, but now I was back in my boring home town for the summer, with little fun to keep me occupied or contented. My Dad insisted on me getting a job for the summer to help pay towards my schooling, something which felt was perfectly reasonable, but I still resented having to do so a little. I had made rich friends in college who were spending their summers at lake houses and foreign exotic locations, and here I was reduced to going door to door in my neighborhood asking if I could mow people's lawns.

I had gotten a couple people who wanted work done (and a lot who didn't) when I walked up the driveway to my neighbour two doors down, Mr Harry Clarke. Mr Clarke was a little younger than my Dad, about 45ish I reckoned, and had lived alone on the street for as long as I could remember. He was a nice guy who maintained his garden well, and mostly kept to himself, and that was about all I knew about him as I knocked. Patiently I waited for the door to open.

"Hi Mr Clarke, my name is Dylan Jones, I live a few doors down from you. I'm canvassing the local area to offer my landscaping and gardening services to interested customers. I may be young, but I'm hard working and take pride in doing a job properly, would you be interested in a trial lawn mowing, half price for the first cut?" I said, I knew my sales pitch off by heart by now.

Mr Clarke seemed to silently consider my offer for a moment before he spoke. "I'm afraid I already have a local company contracted to look after my lawns young man. But I admire your work ethic, are you available to do household duties as well? My normal cleaner is away on holiday for the next month, and with my work taking me away from the house at all hours I daresay but I have fallen quite behind." finished Mr Clarke.

"Ehh, it's not something I've done professionally before, but I'm no stranger to using a mop, and I'm certainly willing to give it a go. What tasks require doing?" I enquired.

"Just general housekeeping, laundry vacuuming and the like mostly. I can give you a quick tour if you're interested? I'm happy to pay cash in too if you like, so the IRS won't be eating into your part of next year's college money?" he continued.

"Yeah sure sounds great, I'm sure I could handle that." I replied eagerly.

Mr Clarke showed me around the house. It was a two storey, four bedroom, two bathroom home, with one of the bedrooms converted to a home office as Mr Clarke did a lot of work from home apparently. The house looked well furnished and very neat, I didn't know what Mr Clarke did for work, but I assumed it was must be something quite well paying based on how fancy dinner if his furniture looked.

After my orientation Mr Clarke said he was going to his office to do some work and left me to get on with mine too. Truth be told I was probably built more for inside work than outside work anyway. I was about 5ft9, slim smooth build, short brown hair, and with what I'd been told was a decent looking face. Certainly not the physically imposing specimens like my Dad and older brothers were.

So I got to work immediately, cleaning the kitchen and removing any expired food from the fridge. I then put the dirty laundry in the machine, and when it was done I transferred them to the dryer. While they were in the dryer I vacuumed the lower floor, from the front door in. I was just finishing the vacuuming of the living room when Mr Clarke walked in.

"This looks to be very good work Dylan, thank you. I have to go into the office for a few hours, would you be able to fold and put away the dry laundry, and we'll consider your day done after that? You can leave by the front door as it will lock behind you without the need for a key, and I've left your payment on the kitchen table." said Mr Clarke.

"That sounds great, thank you. I won't be too much longer." I said.

I heard the front door close as I put the vacuum away, signalling Mr Clarke had left the building. I made my way to the laundry room and the clothes were indeed fully dry. I then proceeded to fold them all. It was only once I had this done that I realised I didn't know where the clothes went, or even which of the bedrooms was the one Mr Clarke slept in.

So not wanting to have to message my new boss and tell him I possibly wasn't properly paying attention during my orientation, I sheepishly wondered the house looking for the correct bedroom. I made my way up the stairs and onto a soft carpet landing. I made my way to the end of the hall and looked into the room to my right. It was a larger room than I'd expected, with a large king size bed complete with twin bedside cabinets and two doors leading off the room which I discovered lead to a walk in wardrobe and ensuite bathroom respectively, I knew when I saw the array of well maintained suits that I was in the correct room.

I got to work right away, putting away the fresh laundry in its correct place. I had found the correct location for almost everything, except for a pair of fabric cuff links. I decided after some long searching to check the bedside table on the side of the room furthest from the wardrobe (I'd already found the underwear and socks location in the cabinet nearest the wardrobe).

I casually opened the top drawer of the cabinet to find no other cuff links, but I did find a large collection of woman's underwear. There were at least 20 pairs of mostly risque looking garments, thongs and skimpy glittery panties filled my vision. I never knew Mr Clarke to have a wife, but I guessed he must have a regular lady friend of some kind. I now figured it highly unlikely that the middle drawer was where cuff links went either, but I was curious now. I opened the drawer to find a series a bras, stockings and even a garter belt. Some of the colours and designs matched some of the panties I'd already seen, signifying they were likely purchased as individual sets. I held the cups of a particularly attractive looking black bra in my hand, picturing the tits that had previously been encased within it.

I'd forgotten completely that I was looking around the private area of what was basically my new boss's house, without thinking I opened the bottom drawer to see what was inside. Wow, inside was what I could only describe as more sex toys that I'd ever seen. There were dildos of various sizes, 4 different buttplugs, lube, gags, restraints, and even some other items that I genuinely had no idea what they were used for. I picked up one of the dildos, I didn't know much about dildos, but I knew the flared based on this one meant one thing, this dildo was purchased for the express purpose of being used in someone's ass. I stared at it, like many young men I'd watched a lot of porn, and the thought of this dildo being used in some young slut's ass was getting me a little excited.

I closed the drawer and was going to get up but my mind started to ponder silently. Again without thinking about potential consequences I opened up the panty drawer once more and rummaged around, pulling out a pink glittery thong. It seemed to be made of quality material, and across the crotch had the word "cumslut" in white shiny font. I stared at it, mesmerised at the thought of the person who would wear such an item, when suddenly I heard a noise from the hallway. Heart in my mouth, I instantly tried to make it look like I wasn't doing exactly what I was doing. Nothing further happened, no door creaked open, so I mustered the courage to open the hall door myself. Relief, upon opening the door I was greeted by a small tabby cat, keen to investigate who this new person in his house was.

I shoed the cat away, and returned to Mr Clarke's room. This time I went back into the walk in wardrobe because I had a curious question to answer in my mind. I found women's underwear, but where was this anal slut's regular clothes? I opened the first of the three closed cabinets to find more shirts and suits, but then I opened the second cabinet and wow. Inside the appeared to be just about every sexy roleplay uniform I could imagine. School uniform, maid, nurse, police woman, and many more I couldn't fully identify. I remember noting how short the lower half of all the uniforms looked. Clearly whoever's wearing these were not concerned about their ass being visible to those around them.

I really wanted to stay and explore further, but I sensed I was already lucky to have only had a housecat barge in on me invading Mr Clarke's privacy. I tidied away any evidence of my peeking, put away the last of the clean clothes, collected my money, and made my way home.

My parents were pleased that I'd had a good day working, and that I may have some repeat customers. I ate my dinner, and shortly after said I was tired and going to bed. I was just taking off my pants when I realised something, I had accidently put the cumslut thong in my pocket. I must have done so when I heard that cat in the hallway. I stared at it, instinctively smelled the crotch, imagining the pussy that last contacted the skimpy material. Feeling my 5 inch cock twitch into life, I got out my laptop. I knew exactly what I wanted to search for, cum in mouth compilations. I loved watching sluts swallow loads, and this time as I loaded up a video and watched these nameless cumsluts perform, I thought of whoever wore these panties last. I pictured them on their knees in that very bedroom as Mr Clarke came on their face and in their mouth. It didn't take long, and within minutes I blew my load all over my bed. I tidied up after myself, and drifted into a peaceful sleep.

The following day I got up and got dressed. I was just planning my lawnmower marketing route for the day when my phone buzzed that I had a text, and to my surprise it was from Mr Clarke.

"Hi Dylan, you did some great work yesterday. Would you be able to come over to clean and vacuum the second floor at some point today? It would be a big help if you could."

I had nothing else to do, and that beat the heck out of my door to door sales routine.

"Yep sure I be over in about an hour or two." I replied.

Mr Clarke's reply can't fast. "Excellent. I'll be away until the evening so I'll leave a key under the main floodlight beside the pool. Thanks Dylan."

I got dressed and had breakfast, before I left I thought about bringing those cumslut panties back over with me. But I decided against it. They were just so hot, he wouldn't notice one pair missing, and I already knew that I was going to have a great jerk off session tonight thinking about those slutty undies.

I arrived at Mr Clarke's by mid morning and set about getting my allocated jobs done. I purposely left Mr Clarke's room until last, I knew I wanted to have another look around the more risque aspects of the room. I did what work I needed then went straight for the panty drawer. I ran my hands through the array of garments, they definitely seemed more slutty than what I would expect to be standard for most women. So many thongs, G-strings, and skimpy coverings of all colours.

I next reopened the bra drawer and rummaged for a bit and to my surprise I pulled out a pink glittery padded bra with a familiar fabric feel, along with the word "cum" on one cup, and the word "slut" on the other one. It was clearly the partner to the thong that I'd borrowed last night. I stared at it again imagining the person who would both buy and wear such an item. Clearly she must be a person who's into cum, likely one of those women I'd seen in porn who swallow load after load of cum like it's a vitamin drink.

I left the bra on the bed and made my way towards the wardrobe where all the slutty uniform outfits were. I never really got a good look at all of them. I had just separated the a maid outfit from a naughty nurse when I noticed a box of discs hidden at the back of the bottom shelf of the cabinet.

I reached into the box and pulled out one of the discs, which looked to be the size of a CD or DVD. It was labelled "Jamie 061024", my heart skipped a beat, these had to be sex tapes. I stared, there must be at least 20 of them, I wondered if any of these sluts were wearing the cumslut lingerie, but had no idea if any of them were, without watching them all.

My heart was in my mouth, but I knew what I wanted to do. I pocketed the DVD I had in my hand, and feeling in a real YOLO mood, the cumslut bra also, and finished the last of my work then made my way home. I feigned not being hungry and made my way to my room.

I put the disc in my dvd player, locked my door, and put my headphones in so I had complete privacy. The disc loaded up and before I knew it I was staring at a dark screen as nothing seemed to be happening on the DVD. I skipped forward a few times hoping to catch the middle of the action but still nothing, so losing patience a little, I skipped ahead until almost the end.

There was certainly action happening in this clip. It appeared the guy (who I assumed was Mr Clarke) was fucking the girl from behind while holding the camera POV style, and wow it looked like he was fucking her in the ass too, and hard. His cock looked to be quite big (way bigger than my 5 inches anyway). She appeared to have stockings and a garter on, I assume her wet panties were pulled down around her ankles out of view. Her hands were handcuffed behind her back, though she sure sounded like she was quite happy with the pounding she was recieving, repeatedly asking for her guy to "use my bitch ass" and to "fill my ass with your cum". The guy seemed to listening to the her request and picked up the pace, thrusting harder and faster than before, and sure enough after another 60 seconds I heard strong moaning, as I assumed he was fulfilling her request to fill her ass with cum.

He pulled out of her ass after another few thrusts and zoomed in with the camera. I watched as a little cum started to leak out and drip down onto her.... onto her balls! I was shocked, this wasn't a woman's ass, this was either a guys or a transexuals ass. I hadn't even considered this, so I instinctively rewound the tape about 15 minutes. It was certainly a guy, he was young (looked about my age), short black hair, and was currently on his knees sucking Mr Clarke's cock like it was a lollipop. He appeared to already be handcuffed, but again that didn't seem to be bothering him. His enthusiasm for sucking cock would put the typical porn sluts I fantasised over to shame. I was mesmerised, but had no idea what to feel. It was hot, and I was certainly rock hard still, but I couldn't accurately articulate why if I was suddenly asked to explain myself.

I decided to rewind back to the start, to wherever the video started actually playing, and it cut to this young guy sitting on Mr Clarke's bed, like he was about to be interviewed, and sure enough right then a voice that I recognised as Mr Clarke's spoke.

Mr Clarke: Hi Jamie, how are you doing?

Jamie: I'm doing great, I'm excited to start.

Mr Clarke: Great. Before we start our little home movie I'd like to ask you a few questions, you know like just before some porn scenes.

Jamie: Yeah go for it.

Mr Clarke: So how old are you, and how long have you been a little cock slut?

Jamie: (Laughing) I'm 20 years old, and I guess I've been taking dick for about the last 6 months or so.

Mr Clarke: And how did that all begin?

Jamie: Oh the usual I guess now. Out of curiosity I posted an ad on Grindr and thankfully you responded to me. You were really patient with me, and slowly but surely brought out the little whore buried deep inside.

Mr Clarke: Very nice, and what have you enjoyed doing the most so far?

Jamie: Oh being fucked in the ass hands down, I'm certainly a bottom bitch for sure.

Mr Clarke: Very nice, and how do you feel about bondage?

Jamie: Yeah I'm good with bondage, it's hot to know that you're about to have your way with me whatever way you want and I can't do anything about it.

Mr Clarke: Awesome, and how do you feel about wearing lingerie, bras panties etc?

Jamie: Umm yeah I like a little bit of it. Like I'll happily wear some bras and panties, it signifies that I'm the bottom which I find hot. But I'm not really into being a full sissy, much to your disappointment I know (laughing).

Mr Clarke: That's ok, I love working with the other person to create a fun experience for all. So finally what are your thoughts on cum?

Jamie: (Again chuckling) I'm good with cum. If I had a choice I really love when you cum in my ass. I mean I'm fine with you cumming in my mouth like you love, and you know I'll always swallow like a good little slut. But the feeling of cum dripping out of my ass just gets me going so much more than the taste of cum on my breath sorry.

Mr Clarke: I think we can accommodate you there no problem, so what say you were get you a little more comfortable and get down to some fun?

Jamie: Sure, sounds great.

The scene then cut to Jamie getting on his knees like before, and I decided now was a good time to turn off the video. My head was spinning. So Mr Clarke wasn't fucking a load of hot young women, but a load of young guys. He was fucking their mouths and asses, dressing some of them like sissy sluts, and using them. He liked cumming in guys asses, but preferred to cum in their mouths if possible, which felt like a strange fact to know about my new employer.

I stared uncomfortably at the now blank screen, and I kept my eyes open because when I shut my eyes an image invaded my brain like a parasite and I couldn't get it out of it. When I shut my eyes I imagined I was there in Mr Clarke's room, wearing the cumslut lingerie. He was fucking my mouth and ass and I was loving it. My cock could take it no more and I started jacking it to this thought. I immediately felt my orgasm build, but then stopped, without thinking further, I stripped naked. I put the thong on first, sliding it up my shaking legs. The bra took a while to put on, and I ended up having to put it on with the clips around my chest, then twist it into place. I then got on my knees, freed my cock from its panty encased prison, closed my eyes, and began jacking it furiously. In my head I was getting ready to take a load on my face, without thinking I stuck out my tongue as my orgasm reached it's peak. As my body shook and I started to cum, I imagined Mr Clarke above me, cumming on my waiting face, with my mouth open wide like those greedy porn sluts I fantasised over most nights. After what felt like forever I opened my eyes and took stock of my situation. I was dressed explicitly as a "cumslut", and I had just jacked off imagining my neighbour, who I just discovered was gay, cumming on my face. I shamefully and silently took off the lingerie and put back on my regular clothes, I then cleaned up the mess I had created earlier, and decided tonight was a good night for an early sleep. I got into bed, and after another half an hour of some confusing thoughts, I drifted off to sleep.

The following morning I stayed in bed. I didn't want to get up, I didn't want to have to deal with what I'd done last night. I wasn't gay, I liked women. But I couldn't reconcile that thought with the thought of me being used by Mr Clarke like the way he'd used young Jamie. I didn't know what I was going to do, but I knew I had to go over to Mr Clarke's house again today. I messaged him saying I thought I'd left my wallet there when I was cleaning yesterday and asked if I could stop over to take a look. He told me that he wasn't at home today, but that I could use the spare key to go have a look, just like I'd done the day before.

I got dressed and had a quick breakfast before going over to Mr Clarke's house. I brought the DVD with me, I was going to put that back before Mr Clarke noticed it missing. But I just couldn't bring myself to bring the bra and panties with me too, I just wasn't ready to be done with them yet.

When I arrived at Mr Clarke's I went straight to his room. I put the DVD back in its spot. I flicked through the other DVDs a little, I wanted to see the names. There was Michael, Juan, Joey, Elijah, Simon, Philip, and more. They were clearly all guy's names, and each DVD seemed to feature a different person each time.

After another few minutes I left the walk in wardrobe, and stared around the room again, not really sure what to do next. I thought of all the sex that must have happened in here, the cum that must have been released, the sextoys shoved up asses, the sex toys. I remembered the flared base dildos and assortment of butt plugs from night one, back when I'd assumed they were being used on a girls ass. Now I knew that more likely than not they were being used on young guys ass's, ass's just like mine. I opened the sex toy drawer and rummaged around until I found what looked to be the smallest butt plug present. It was clear and plastic, maybe about 2-3 fingers wide at it's thicker point, and had a long flared base as the other end, an ideal starter plug I surmised. I knew instinctively that I shouldn't, but I pocketed the butt plug. I didn't know if I was ever going to use it, but I suddenly wanted to have it.

I closed the drawer and strolled absent mindedly around the room. I looked at a naughty nurse outfit and wondered was the last person who wore this a young guy who shortly after putting it on had Mr Clarke's cock in their mouth and/or ass? And why was I fixating on that part so much? Did I really want to see what that would be like? Would it hurt, would it be humiliating, would it be.... fun? I was all kinds of confused.

I decided that I had enough snooping around Mr Clarke's house for one day, so I decided to head back home. Thankfully my family were heading away for the weekend upstate to visit family so I had the house to myself. I guess this was one benefit of me being a moody teenager was that nobody wanted to spend 4 hours with me in a car to see Grandma, so I was left to my own devices for the next few days.

I got home and did my usual routine (clean up, make dinner, amble aimlessly around the house) until about 9pm, when I decided to have a shower. I finished up and before I knew it I was sitting on the edge of the bed with my laptop in front of me, just like I had been on so many previous occasions. Normally it's straight to pornhub, but tonight I was unsure. I wanted to see something else, ideally another one of Mr Clarke's tapes, but failing that, something similar maybe.

Unsure where to look I typed in a gay porn site I knew the name of but had never visited called Gaymale Tube. I went to the categories and browsed. To my disappointment there wasn't much of what I was looking for. Don't get me wrong, there was plenty of videos of guys getting their asses well and truly used, but I wanted to see these guy getting fucked while wearing lingerie, like the guy in the video was.

After some digging I found a sister site to the one I was on called Tgtube, and straight away, success. There was every version possible of cocks in asses that I could imagine, but one category jumped out at me more than others, sissy. I clicked on the category and there it was. Guys mostly young (like me), mostly white (like me), and mostly dressed in various degrading whorish outfits (a lot more than a bra and thong for these people), and they were sucking, fucking, rimming, and swallowing with the best of them. I clicked on a video of a young sissy guy dressed in a skimpy french maid outfit that barely covered his ass. I watched as he bent over and spread his ass, how he teased a decent sized dildo up against his anal entrance. Then his friend arrived in the picture, a somewhat older and more muscular guy with a decent sized cock on him. And without any difficulty, hesitation or shame, the sissy maid started deepthroating him like the cure for cancer could be found by sucking the cum out of this guy's cock.

I was clearly getting excited and I really wanted to start jerking off, but I had more experimental plans in mind. I took the buttplug that I'd taken from Mr Clarke's, and applied a generous amount of nearby lotion to both the buttplug and my puckered anus. I stared fixated at the screen, where the maid was now licking her man's balls with abandon, and I pushed the plug into my butt. Or so I thought, I tried pushing it in, I really did, but honestly it hurt, the stretching of my butt didn't feel nice and made me not want to push further. I knew that if I put the plug in the bed and tried to sit on it then the weight of my body would surely be enough to force it in but honestly I was not up for it, and what if it hurt more, what if it got stuck? This was not like how porn made it look. I dried off my butt, and the plug, and put it away in a drawer. I turned back around to the screen to see the sissy still on her knees, and her nan jacking off near her face, looking like he was getting close to the finish while the sissy encouraged him on.

Sissy: "Oh yeah, are you gonna cum on my tongue, come on I want you to cum on my tongue, glaze my slut mouth with your cum, make me your sissy cum slut, train me to be your sissy cum dump."

I watched as the sissy's dirty talk seemed to have done the trick as three or four thick spurts of cum flooded her gaping mouth. She held it in her mouth for a bit, moving out around like it was mouthwash. And then as if by magic one glug from the sissy and voilà, the cum was all gone, she'd swallowed every last drop.

I rewatched the ending a couple of times. What struck me was the sense of of purpose, of pride even that the sissy maid gave off while swallowing the cum, sure she could have been faking it, but it looked real to my simple eye.

I was also struck by some of the words used during the scene, and so I clicked on the search bar and typed "sissy cumslut training". Wow there were so many videos, I clicked on a highly rated video at the top called "Sissy cum trainer (for serious sluts only)". The video loaded, and after the banner ads were removed I clicked start. I soon saw that the video was formatted like an instructional video. First I had to dress like a slut, then I had to walk around dressed like said whore, then I was to use cum that I'd saved from earlier and to put it in my mouth (I didn't have any cum saved up though so I did nothing). It then cut to scenes of porn sluts being cummed on, cummed in, and everything in between. As the scenes flashed across the screen, so too would what I assumed were training captions and slogans. "Can you feel that delicious cum, you know you want to be like her, and you can be, just submit, you will never swallow enough cum to satisfy you."

There were other slogans flashing across the screen, but I had stopped noticing. I was urgently rummaging around the room until I found the cumslut lingerie and quickly slipped them on. I immediately got on my knees like I had the night before, closed my eyes, and started furiously jerking off. In my mind I was in some non specific porn studio, on my knees and begging Mr Clarke to cum on my face. I had my tongue out just like the sissy maid from earlier. And right as Mr Clarke was about to reach orgasm, in the real world so did I. I was suddenly ripped from my fantasy world and suddenly I was back in my room, on my knees wearing my neighbours cumslut lingerie and my hand was covered in cum and I'd just imagined being used like a sissy slut for the second night in a row.

I silently, and slightly shamefully removed the lingerie, got dressed, and got cleaned up for bed. I was glad again that my family had gone away for the weekend, I was in no place to be making boring small talk with anyone for the next couple days. I went to sleep that night with so many mental images swirling in my head that it felt like I was dreaming before I'd even gone to sleep.

Mercifully I actually did sleep well that night and woke up mid morning Saturday feeling rested and refreshed. I picked up my phone to see it was 10:45am, and to my surprise I also had a text from Mr Clarke.

"Hi Dylan, just wanted to check if you managed to find your wallet yesterday after?"

Thinking to myself wow that little lie felt like so long ago that seemed like days previous. I responded quickly.

"Yeah I find it in my living room, it must have fallen out of my pocket watching TV. Thanks for letting me look round the house yesterday though."

Mr Clarke's next message only took a minute to come in also.

"Oh that's great, I was quite worried that you'd lost it over here too be honest."

I again did my small talk message as I was almost finished getting dressed by now.

"Ah yeah so was I for a while. All good now though, thanks Mr Clarke."

I finished the message thinking that was the end of the conversation, but to my suprise my phone beeped again to say Mr Clarke had sent another message.

"Yeah I was so worried about your wallet that I took a look over the house cameras last night to see if I could spot it for you. I didn't find any wallet, but I did notice you take something from my bedroom that didn't belong to you, care to explain yourself?"

I froze mid step, Mr Clarke had cameras, and he'd seen me on them? Oh no I'm dead, what do I say, do I deny it? But he's got video evidence, I was screwed. Nervously I typed.

"I'm so sorry Mr Clarke I didn't mean to do it. I just stumbled across some things I hadn't expected and got carried away, please don't tell my parents."

I waited nervously, my heart in my mouth, until the next message appeared.

"No I don't think telling your parents will achieve anything, and you do sound sorry. But you have stolen from me and that's not acceptable. I would like you to return my property to me immediately though. Seeing as I'm feeling charitable you may eh "wear" what you stole as you bring it over to me if you wish, then we can have a good discussion about boundaries and respecting them in person. My door is unlocked and I'll be upstairs in my room, I expect to see you soon."

I re-read the message a couple of times until I was sure I understood what Mr wanted. It seemed like he wanted me to return the bra and panties, while wearing them, and to do it now. I know I'd only recently fantasised about this guy cumming in my mouth, but these were private jerk off thoughts, I could never follow through on any of this, could I?

I silently went back to my room and considered my options. I could ignore the message, but imagine if he got my Dad involved? I could just drop them at the front door and run? But what if I did wear them over, and what if it was the most fun I ever had? Dam I had never expected to have to make such an important decision so quickly. My brain was a mess, I took a deep breath and decided to strip down naked, this time putting on the pink glittery cumslut bra and thong that I'd now started to become quite used to wearing over the last couple days. I put on my usual t-shirt and shorts on over them, and still uncertain if I was doing the right thing, left the house and made my way over to Mr Clarke's place.

As I walked up the drive to Mr Clarke's house everything in my head said just go home, but for reason my legs were still walking forward. I walked up to the front door, and sure enough it was unlocked. Taking another deep breath, I pushed the door open and walked inside. Mr Clarke's house looked exactly as I'd remembered it, but the tension inside my stomach made me perceive it differently. It was so quiet, and I was scared to say anything for fear of what would happen next. Eventually after a few solid minutes doing nothing I managed to utter a muttered "Hello?" through my dry and raspy throat.

"Ah you've made it Dylan, I'm up here." said Mr Clarke.

I made my way up the stairs, feeling like I was walking the green mile, slowly pushed open the door to Mr Clarke's room. Inside Mr Clarke had his back to me, he was sitting at a desk in the corner of his room, typing something on his laptop.

"Have a seat on the bed please Dylan, I'll be finished this in a moment." said Mr Clarke very casually, as though what was happening was perfectly normal. I sat silently on the bed and waited, wondering why did I come here, and could I somehow go back in time so none of this ever happened?

Then without warning Mr Clarke turned around and was looking right at me.

"So Dylan, do you have something you'd like to return to me?" asked Mr Clarke.

I stood up off the bed, but I just couldn't bring myself to take my t-shirt off, it was just too embarrassing. So without thinking I turned around, and now that I no longer had to look Mr Clarke in the eye, I wordlessly took off my t-shirt and shorts and stood there, waiting, for what felt like an eternity for something to happen. I heard Mr Clarke begin to slowly walk towards me, so I knew something was about to happen.

"Hmmmmm." said Mr Clarke, as though he was a mechanic examining some unusual bolt arrangement on a car.

"So Dylan, this is very interesting, because the camera I looked at only showed you had taken one of my smaller butt plugs. I didn't know you'd also taken my cumslut lingerie, very interesting indeed." said Mr Clarke. He then suddenly slipped his finger under my thong and rubbed his finger down the crack of my butt, sending a jolt of electricity through me.

"I don't see the butt plug anywhere, where is it?" asked Mr Clarke nonchalantly.

"It's at home, I completely forgot about it I'm sorry." I said, cursing myself for forgetting it.

"I had hoped to find it right here." said Mr Clarke as he again rubbed my nervous anal entrance. "May I be as bold as to ask you why it isn't inside this very cute little ass of yours?" continued Mr Clarke.

"Eh I tried to eh, I tried to use it, but it wouldn't fit, it hurt too much I'm sorry." I stammered, why was I apologising? Was I apologising because I'd taken the butt plug without permission, or because I wasn't able to fit it up my ass? I had no idea anymore.

"That's ok. So I take it that means you've not had items in your butt before this? asked Mr Clarke.

"No I haven't." I said simply.

"And how long have you been dressing in sissy lingerie?" pressed Mr Clarke.

"It's my first time too, it's my first time doing anything like this ever." I said quietly.

"Very nice, well it really suits you. Can I ask, why did you decide to wear them?" asked Mr Clarke.

"I'm not sure, I saw someone in one of your videos wearing lingerie and got curious. I've already returned the video, I'm very sorry for invading your privacy so badly." I said quickly.

"Well I think I can forgive a youthful mistake or two. But I must therefore ask, if you know I like sissy boys, why did wear sissy lingerie over here? Do you want to be a sissy boy too?" continued Mr Clarke.

"I don't know, it just excited me and I don't know why I tried them on, I guess I was curious." I said.

"And what are you curious about doing with me exactly? Was it just wearing sissy lingerie, or was it something more?" said Mr Clarke.

"I eh, I don't know. Anal sex looks like it would hurt too much to try." I said.

"And how about oral sex? How would you feel if something, for example my cock was in your mouth instead?" asked Mr Clarke.

"Eh, well it wouldn't hurt as much I guess." I said simply.

"No it wouldn't I suppose. So we can reasonably conclude that you are somewhat open to at least see what it feels like up be a cocksucking sissy boy, and I am open to the idea of you using my cock to practice with if you like. There's just one other problem really." finished Mr Clarke.

"What is that?" I asked, feeling like I was being lead into a trap.

"Well it's the choice of lingerie you're wearing. You see those are a rather special set of lingerie that I don't ask people to wear very often. And the reason for that is quite simple. I have a special rule that if you wear cumslut lingerie then you have to be a cumslut, and I have to cum in your mouth. So I suppose you could try on something else, or we could just lock in now that whatever happens next, it's going to finish with you having a mouthful of cum as the grand finale. If nothing else it would give you time to mentally prepare yourself, what do you think?" asked Mr Clarke, as casually as if he were talking about the weather.

"Eh, I guess I could try that." I said my cheeks reddening at the thought of what I'd agreed too.

"Ah, I'm afraid in this modern litigious society I'm going to need a more specific yes to exactly what I've proposed." said Mr Clarke.

"Yes you may cum in my mouth." I said.

"While you're dressed like a cumslut?" continued Mr Clarke.

"Yes." I said quickly.

"Specific consent please." said Mr Clarke again.

"Yes you may cum in my mouth while I'm dressed in sissy lingerie, and you can call me names like slut and sissy and make me do other stuff that you like, is that specific enough." I said, wondering if Mr Clarke was a lawyer.

"Yes that's perfect, thank you Dylan. So now that we've sorted the big finish so to speak, I feel like we must return to that cute little ass of yours that I've been staring at for the last few minutes." said Mr Clarke.

"Ok." I said wondering what else I was about to sign up for.

"Well it's just that a sissy's ass, even one as cute and tight as yours, is made to be used. So there's a couple things can help you out when starting out with anal. The first is lube, we are going to use loads of it, more than you think it's necessary." said Mr Clarke as I heard a loud pop open and the squeezing of liquid. I then felt a sudden cold sensation as Mr Clarke truly did coat my ass in a thick layer of lubricant. I then heard some more squeezing but I felt no more lube, so I'd assumed he was lubing up something else, something I assumed was going in my ass really soon. I didn't dare turn around and even look at Mr Clarke, though I didn't want him to stop either.

"Excellent. So now that we've taken care of lube, let's move on to technique. There are a few things we can do to make anal penetration easier. Firstly, don't tense up. It's a natural reaction if you've never had anything in your ass before, but you have to resist the urge. A good thing to do is to imagine your trying to push something small or of your butt. It will keep your butthole relaxed and make penetration much easier. The other thing is to breathe, as counter intuitive as it is you have to keep breathing and relax, nothing is happening that will ever hurt you, and very soon you'll grow to really like it, once you get used to it. Now that's a lot of words, let's see how this works in practice." finished Mr Clarke.

And as soon as he said that I felt something push against my sphincter. I tried to relax and breathe, and to my surprise whatever it was slid inside without any pain. I felt whatever it was move a little inside me, and deduced that based on how close Mr Clarke was to me, that it must be his finger that was in my ass. But he didn't stop there, and after about 30 seconds I felt another finger push it's way inside, again with no particular pain. Mr Clarke would slowly push his fingers in and out of my ass, while his other hand cupped and grasped one of my butt cheeks. After about two minutes of this Mr Clarke slowly withdrew from my ass, that was certainly easier than trying to sit on a buttplug.

"You did really good there Dylan, how did that feel?" asked Mr Clarke.

"It felt fine, it didn't hurt at all." I confirmed.

"Great. I have to reiterate that you really do have a plump pert little ass, and super tight, I glad you are open to me exploring it with you. But let's move on to something more significant, something bigger. To take something bigger up your ass you need to keep mind of everything we've discussed already, but you also need something else, sexual excitement. It's hard to take an 8 inch cock or dildo up a tight little ass like yours unless you really want to have said item in your ass in the first place. The pushing, stretching, and pressure can be foreign and uncomfortable initially, and can easily disrupt your attempts to relax and keep breathing. So with that in mind, tell me about why you agreed to wear cumslut lingerie over to a relative stranger's house, a stranger you knew likes to fuck young sissy boys. What were you hoping would happen?" finished Mr Clarke.

"I'm not sure. I guess I was curious to find out, but had nothing particular in mind." I said after a period of embarrassed silence.

"Ok, let try something else. Tell about the most recent porn you've watched that involved sissy's like you." continued Mr Clarke.

"It was a compilation of girls taking cumshots with slogans on the screen. It was called a cum trainer video I think." I said, going red in the face with embarrassment.

"And were you wearing this lingerie while watching this?" asked Mr Clarke.

"I put them on during the video." I admitted.

"So you want to be trained to be a cum slut then?" asked Mr Clarke.

"I'm not sure. I guess I'm curious to try. It sounds both humiliating and exciting at the same time." I said honestly.

"And do you know what those girls did before they received all that cum? They were fucked by those same cocks, very likely in their asses too. That's the price they paid to get that sweet sweet cum they craved, are you prepared to do the same?" continued Mr Clarke.

"I dunno, I guess I could try." I said simply.

"I want you to think of the dirtiest cumslut you saw in that video. Imagine how she felt during that video. Imagine her taking that cock in her ass, but that cumshot was what she was waiting for, that's what was on her mind. Now imagine that whore is you, and bend over a little more and do what all good whores know to do." said Mr Clarke as he gently pushed my back forward.

I leaned forward until I was face down in the blanket. I then felt something bigger than a finger push up again my exposed butthole. The pressure built around my anus, the mystery item pushed on without any pause or hesitation. I did everything Mr suggested. I focused on my breathing, keeping my ass relaxed, and thinking of that cumslut video. I imagined I was taking the world biggest cock in my ass, then I imagined I was taking Mr Clarke's cock in my ass, he had me dressed like a naughty schoolgirl and bent me over the desk as he pounded my tight waiting ass. I was moaning like a whore, but I didn't want him to stop.

Back in reality I felt my ass relent and the item enter me. It was huge and long, too long to be a buttplug. Mr Clarke continued to fuck me about 10-20 times with the item, in long slow motions, all the while whispering things like "bet you love that slut" and "oh yeah we got a cock whore here for sure". After about 20 strokes I felt the item withdraw back from my ass, leaving an odd feeling gap in me where that item had been.

"How was that? You know you've just taken a 6 inch dildo all the way up your ass, not bad for someone who said a buttplug half the size of this was too big only 24 hours ago." said Mr Clarke half laughing.

"It was ok yeah, I didn't know how big it was I guess." I said simply.

"It'll get easier I promise, and a lot more fun too, that ass has a lot of potential." laughed Mr Clarke, giving it a playful slap as he said so. "So Dylan, now that you've had something in your ass that you didn't expect would ever be there, I think it's time to move on to something else, can you guess what that is?" finished Mr Clarke.

"Something in my mouth that I'd never expected to be there?" I replied simply.

"Smart boy, now cock sucking is a bit more simple and for now all you really need to know is this, enthusiasm is enough while you learn the skill, and with that the lessons of the day completed, it's time, on your knees please Dylan." finished Mr Clarke.

I silently stood up, turned around to face Mr Clarke, and then dropped down to my knees. This was both the thing I was most looking forward to, and most scared of since I got that text from Mr Clarke. What does a cock taste like, will it make my jaw ache, will I feel slutty and empowered, or cheap and used, and what does cum taste like? I'd already agreed to let him cum in my mouth but would I have to swallow it too? Would it make me gag, or wretch? I had so many questions, my head and heart were racing. I was eye level with Mr Clarke's crotch, and he was about a foot and a half in front of me, possibly watching me while this inner monologue ran through my head.

"Now Dylan, if you like I will remove my pants and you can see my cock if you wish, all you have to do is ask me." smiled Mr Clarke.

"Can I please see your cock Mr Clarke" I asked obediently.

"Oh I think you can do better than that there Dylan. Convince me this is what you really want." said Mr Clarke.

"Please Mr Clarke, please let me see your cock. Ever since I saw it on one of your sex tapes it's been stuck in my brain. Please, I need this." I finished.

"Oh well all right then." sighed Mr Clarke, and with that he lowered his pants to reveal his semi erect cock. It was already 6-7 inches, I'd guessed it just be about 8 inches when fully erect.

Mr Clarke took a step towards me, and I was convinced this was where I sucked cock for the first time, but as he neared me he spoke again.

"Ah yes I almost forgot these, silly me." laughed Mr Clarke to himself, and with that he whipped round behind me quick as a flash and handcuffed my hands behind my back. I had never been restrained before, and it had happened so fast that I didn't really know what to think.

"You really look amazing Dylan, I could just facefuck you until I burst, but I want to make sure that this is what you want, are you sure you want my cock and my cum in your mouth? asked Mr Clarke.

"Yes I do, certainly." I said, tension rising again.

"Hmm, I'm not sure, convince me you want to become a cock sucker." teased Mr Clarke.

"Please fill my mouth with your cock. I'm dressed like a sissy bitch, I just took a dildo in my ass. I've jacked off the last two nights in a row to the thought of you filling my mouth with your cum. My cock in my panties is hard as a rock thinking about what you're going to do to me. Give me your cock now, I've earned this." I finished. I knew what he wanted, he wanted me to humiliate myself, and at this point I was happy to oblige, I wanted to try this.

Mr Clarke didn't say anything else he merely smiled a little and then he advanced, his cock was only a foot away, then a half foot, 3 inches, 2 inches, 1 inch....

It was wider than I'd expected, I wasn't sure what I was expecting, but the width of Mr Clarke's cock was what struck me most to begin with. My lips and jaw ached a little as I tried to find a comfortable position. At the same time the head of his cock was probing the back of my mouth and making me gag. I couldn't help it, I tried to suppress the gags, but they kept happening, thankfully Mr Clarke didn't seem to notice them, or at least he didn't seem to care. He wasn't probing me overly fast, but he certainly seemed to be speeding up slowly but surely. I remember seeing a pornstar talking about blowjobs before and she talked about swirling her tongue around the cock as she sucked, so I decided to try this. I doubt I did it right, but it did manage to get a little moan out of Mr Clarke, that was pretty cool.

After a couple minutes of this I felt Mr Clarke withdraw from me, as he fully withdrew I caught a glimpse of his balls, and remembering the pregame speech Mr Clarke gave me I went straight for them, licking his ball sack, and even taking one of his balls mostly in my mouth for a gentle suck. Mr Clarke let out another low moan and another minute later, before I knew it his cock was back in my mouth again. This time I was more ready for the size of it and was able to manoeuvre my mouth around it. I focused as much as I could on relaxing my mouth and letting Mr Clarke go deeper in my mouth. In my head I was taking almost all of his cock in my mouth, though looking back on it now I reckon I barely got more than 5 inches of cock in me at my best, I did manage to better suppress my gagging though. I found that by focusing on nose breathing I could handle more cock much easier than my first attempt.

"Oh you're a natural cock sucker Dylan, I'm getting close, keep it up, I hope you're excited, you're about to get your first taste of cum." said Mr Clarke, half moaning at the same time.

Even as my mouth had spent the last ten minutes or so filled to the brim with cock, this moment had dominated my head. What I was trying to decide was, when Mr Clarke started cumming, should I try and have his cock in as deep as possible, so the cum would go down the back of my throat, or just a little bit inside my mouth, so it would sit in my tongue? If he came in my throat then maybe I would hardly taste it, so if it was really bad then I wouldn't wretch. Or maybe he should cum on my tongue, if I didn't like the taste I could spit it out, and I'd get a feel for the texture etc and have a better idea if this was something I could handle more than once. I was in two minds.

Mr Clarke's moans and shouts that he was about to cum brought me back to reality, and thinking fast I decided to take Mr Clarke's cum on my tongue. It came in spurts, but by tucking my chin down a bit I was able to stop any shooting straight down my throat before I decided if I wanted to try swallowing or not. About 4 or so thick ropes of cum entered, followed by a longer series of shorter ones. Mr Clarke's hips moved and his cock moved in and out of my mouth. I moved my tongue over the head of his cock again, partly because I thought he'd like it, but also because I wanted to get an idea of what I was dealing with here. His cum was thick, warm and a bit salty, but it wasn't horrible. I wasn't going to order it as a flavour of ice cream, but certainly not nearly as bad as my worst fears thought it could be.

Our eyes locked and Mr Clarke slowly started to withdraw from me for what I guessed to be the last time. As he pulled out I decided to keep my mouth open and held out tongue until I was sure Mr Clarke could see his cum resting there. Then trying to keep eye contact I went to swallow it, but I had to close my eyes to focus on getting it down, as again I was worried about heaving it back up. But it went down fine, it took a few swallows to make sure it was all gone, and it left behind an after taste that I reckoned would stay with me for a while, but I reckoned I could swallow cum again, and I definitely wanted to suck Mr Clarke's cock again, so that was handy.

"So you've swallowed your first load of cum, how do you feel?" asked Mr Clarke smiling.

"Like I'm finally starting to earn the right to wear this cumslut lingerie." I said, smiling back up at him, I couldn't help it.

"Haha that you certainly are my little sissy in training. Come here, let me remove your handcuffs." said Mr Clarke.

I stood up and turned around and felt Mr Clarke loosen the restraints, but just as I was about to turn back round I felt the head of his cuck right next to my butthole. It felt absolutely enormous up against it.

"I know it likely doesn't feel like it yet, but in a very short space of time this cock will be inside this tight virgin ass off yours, and I promise you'll love that too, probably more than what you just did." whispered Mr Clarke near my ear. It made me feel a little weak at the knees, and very curious for what may e in store for me.

"Well I think that's about enough for now Dylan, you're a really fun young sissy boy, and I know we can make each other very happy for a while. But you'll need to be getting home, your family will be starting to wonder why you're spending so much time cleaning your neighbour's house everyday eh?" said Mr Clarke laughing a little.

"Yeah I do have some chores that need doing at home, but my family are away for the weekend actually." I said as I put my regular clothes back on over my cumslut bra and panties.

"Really? Well in that case hold on a second." said Mr Clarke as he went into his walk in wardrobe. I could hear him moving stuff and generally fumbling around for a couple minutes before he emerged back out, this time with a carrier bag in his hand.

"Here take this, it's some stuff to experiment with, see what you think of it. If you like, you can come back over around 8pm tonight and tell me what you thought of them all. What do you say?" finished Mr Clarke.

"Sounds great." I said, smiling as I left the room, Mr Clarke giving my ass a playful smack as I walked out too.