My Sissy Awakening 03

I had just finished another week of college. Me and a couple friends were discussing what we'd be doing for the weekend. A few were going to parties, a few were going to study, one was heading home to see family, I told them I was working most of the weekend in a nearby hotel, and so would likely sleep there between shifts, in one of the empty rooms.

Of course in reality I was doing nothing of the sort. I was actually going to over to my older lover Harry's house, and spend my second weekend in a row being his sissy bitch. I didn't know exactly what he had in store for me, but I sure was excited and horny to find out.

I knew that our meeting was likely to include some combination of crossdressing, cock sucking, and being fucked in the ass. The crossdressing I was looking forward to, I loved how wearing slutty clothes made me feel, I'd felt like I'd found my sexual role in life. Harry had also sent me some money to get my hands on some different types of makeup, and thanks to an unlimited number of YouTube tutorials, I felt like I'd nailed some of the basics, I particularly loved playing with different blending and contouring products.

I was also looking forward to sucking dick, I really wanted to get mouth fucked, to have Harry use my mouth, I wanted to lick his balls too I felt. Pardon the pun but the whole dick in my mouth thing sounded positively delicious.

Then there was the assfucking. After losing my anal virginity last week, I had envisioned spending the week training my ass for this coming weekend's events. But in all honesty my ass so sore, likely due to the size of Harry's thick 8 inch cock, that I wasn't able to do much training until about Thursday. So anal wise, I still felt my ass wasn't loose enough to do everything I wanted to do in my head, but I felt like I could give it a good go for sure.

I'd done my usual enema prep, packed a bag and made my way to Harry's. On the bus there I reread the messages Harry and I exchanged during the week. I'd sent him photos of me done up in makeup, we'd talked about what we'd gotten up to last week, and then finally we discussed what we'd be doing this weekend. Harry again wanted to do a roleplay, he said it was easier and often more exciting exploring different fetishes and interests when you were pretending to be someone else. Tonight I was going to be a person caught shoplifting, and he was the head security guard who was going to decide what to do with me next. He offered no more details than this, so I was excited and a little nervous for what was in store.

I arrived at Harry's at about 6:30pm. I walked up his drive, wondering to myself what the rest of his house looked like, I'd really only seen a few rooms so far. I then knocked on the door and waited apprehensively.

The door opened quickly and there stood Harry. He looked hot as ever, though this time he had a walkie talkie, and baseball cap on over his jeans and T-shirt, he sure was taking this character playing to heart, maybe he was an aspiring actor back in the day, given he does run a porn company.

"You, inside, go to my office and sit down while I decide what to do with you." Harry's words were forceful and strong, I really felt like I'd no choice but to comply. I made the now familiar path through the glass lined living room and into Harry's office.

Harry's office looked so different to how it did last week. The mahogany desk was gone, replaced by a more simple pinewood looking desk. The bookshelf no longer contained books, but bags and bags of random looking items. There were what looked like CCTV computers on the wall, and even a notice board littered with random pieces of paper. Maybe this was Harry's roleplay studio, rather than his actual office.

My mind snapped back to reality with the sound of the door closing and Harry coming in and sitting down. He leaned back in his chair for a moment, as if he was deep in thought, never taking his eye off me.

"So, you want to explain why you're here?" said Harry.

"Eh, I'm not really sure why." I said, unsure of where to go, improv was not my strongest quality.

"Joey, you've just been caught trying to steal makeup from my store, I can still see the stuff in the bag in your hand for fuck sake." said Harry

"It's not what it looks like, I was just looking at it, I never meant to take it, please believe me." I pleaded.

"I'd love to believe you Joey, I've known your Dad for a long time, I know how disappointed he'd be for me to call him and tell him you'd been stealing makeup, for whatever reason." said Harry.

"But I'm over 18 now, you don't have to call him, please Harry." I said, wow roleplay really is fun.

"You're right, you are over 18. And our rule is if the value of what you stole is high enough, then we've got to call the cops, not your parents, sorry it's store policy." responded Harry.

"But I can't get a criminal record, I'll lose my scholarship, please Harry I need your help just this once." I said, holding my hands in prayer.

"I wish I could do something. Look let's see exactly what you took, and decide what to do from there." said Harry. He took my bag of makeup and supplies and began rummaging through it, taking out everything and laying it on the table.

"Is this it, I thought there was more, based on the CCTV that I saw." said Harry.

"That's everything, I promise." I said earnestly.

"That may be so, but after what you've done you'll have to forgive me if I don't believe you fully, stand up and empty your pockets, and take off your shoes and socks." ordered Harry.

I did as ordered, watching nervously as Harry combed through my stuff.

"Right nothing so far, that's good, now take off your t-shirt and lift up your arms." said Harry. Again I did as ordered. Harry ran his big hands down my sides, sending bolts of electricity through me as he did.

"Good, now open your mouth and stick out your tongue." said Harry. I could hear the sound of latex glove going onto Harry, followed without warning by Harry forcing one of his fingers down my throat. They went deep and fast, like he trying to make me gag, I only just barely held it in.

"Nothing so far, but I still have my doubts, this leaves me little choice I'm afraid." said Harry, as he silently walked over to his desk, opened a drawer, and pulled out a bottle of KY jelly.

"Shorts and underwear off, and lean forward hands on my desk." said Harry

"What, come on, there's hardly any need for this, I've got nothing I promise." I said.

"You're free to decline my search, but if you decline then I will call the cops, who will search you anyway. So bend over now, or bend over later, your choice." said Harry in a very matter of fact kind of way.

Exhaling like this was a a difficult choice for me, I paused then took off my shorts and underwear, before putting my hands flat on the desk with my ass sticking out slightly.

I felt the lube on my ass, followed soon by the presence of a finger rubbing around my anus. Then to my suprise, I felt two fingers push through and make their way inside. They weren't that big, but still bigger than I expected. Harry probed me for a couple minutes, entering and exiting, pushing me forward so I was bent over almost flat on the desk. After a few minutes I couldn't resist myself.

"Are you finished yet, I've told you there's nothing else." I said.

"Just about, just.... one.... more... thing..." said Harry slowly as he reached between my legs with his free hand and grasped my cock, held it there for a minute, before finally letting go.

"Fucking hell your cock is rock hard Joey, are you a fucking faggot?" asked Harry, in a very serious voice.

"What, no, of course not." I said quickly.

"Oh yeah, then why does my finger up your ass make you harder than concrete?" asked Harry.

I said nothing for a while, unsure what to say. Smack! With his free hand, Harry gave me a hard spank on my ass. "Answer me" he ordered.

"I'm not a faggot." I insisted.

"Yeah you are. Wait, you stole makeup didn't you? You're not just a faggot, I reckon you're a sissy faggot aren't you?" said Harry

"I'm not I swear." I pleaded.

"Oh come on Joey, just stop lying to me about everything will you? You know what, fuck it, let's prove it one way or another." said Harry. He withdrew his fingers from my ass, walked over to where all the carrier bags on the wall were, and came back over carrying one of them.

"Right so, go ahead and put this on. This is old evidence from some other thief like you. You do that without an erection and I'll believe you, and you'll be free to go." said Harry. He reached into the bag and pulled out two items, a bright pink thong, and a matching pink padded bra with the words "sissy" and "slut" on the cups.

I held the garments in my hands, slowly I put them on, I purposely pulled the strings of the thong up high as I'd read online that it made my ass stick out.

"Ha, you could drill holes with that cock it's so hard. I bet you fucking love this." laughed Harry.

"I'm not, I just want to go home." I insisted

"Then admit your a panty wearing cocksucker, do that and I'll let you go. Here, put these on too." said Harry, as he handed me a pair of 3 inch clear hooker heels, a pair of white stockings, and a matching white garter belt. I put them on quietly, remarking internally to myself how much easier it was to put these on now that I'd done it a few times.

Harry walked around me without a word eyeing me up and down. "So do you admit you're a sissy bitch bottom? said Harry.

"Please, I just want to leave, if I say yes will you let me go?" I asked.

"You will say yes because you're telling the truth, not just to get out of here." said Harry. "Put these in too so, I can do this all day you know." said Harry. This time he'd given me a white latex style mini dress, It had a deep v at the cleavage, nothing on the arms, and the words "insert here" on the part that barely covered my ass cheeks. He'd also given me a blonde wig, and to my surprise, a white dog collar and chain. Silently I put them on, internally loving the tight feeling of the dress on my skin and collar on my neck, no wonder some girls became sluts when it was so hot to dress like this.

"Now we can keep going, or you can admit what you are." said Harry.

"I...I like wearing women's lingerie ok, you happy?" I said.

"And have you ever sucked dick dressed like a slut? asked Harry.

"Yes." I said.

"And have you ever gotten dressed up like the slut you are and taken a cock up your ass? asked Harry.

"Just once, my doctor fucked me in the ass during a therapy session." I said. It was really hot blending a little reality into the fantasy.

"Yeah really sounds like you made a breakthrough in that session." laughed Harry. "So we've established that you are, as I said earlier, a sissy faggot, and that you don't want to go to jail and ruin your college chances. I have the power to decide if you actually get arrested tonight, and........ I have a cock that loves humiliating you stuck up sissy boys. Can you see where this is going at all?" smiled Harry.

"What are you going to make me do?" I asked nervously.

"Nothing you don't in reality actually want me make you do bitch." said Harry. "Now here take these, and finish your whore outfit, then our fun can begin." said Harry.

Harry gave me the bag of makeup that I'd "stolen", and my now favourite item, thick red lipstick. I put the powders and toners on quickly (which was a little more difficult to do without the mirror, then the other items followed suit. Finally, once I felt I was looking my best I turned to face Harry.

"Not a sissy faggott, ha, I can spot you cucks from a mile away, you know that?" laughed Harry. "Now here's the deal bitch, you do what I say when I say it, you do anything else, well let's just say jail time, and jails have ways of helping you discover your feminine side too." He continued.

"Now on your knees and crawl over here, and while you crawl over, your head is to remain lower than your ass at all times, understand?" finished Harry.

Of course I did as Harry ordered. With my head down I couldn't see exactly where Harry was anymore, he was about 8 feet away from me when I started. As I crawled I felt my tight dress slide up and could feel my ass almost completely exposed, it felt hot.

I stopped when I saw Harry's feet in front of me. I saw Harry's pants and underwear fall to his ankles so instinctively I looked up. "SMACK!" Harry's hand caught me flush on my cheek, he didn't hold back.

"Did I tell you to look up bitch?" said Harry. "No" I replied, my cheek still glowing.

"Then why did you look up?" demanded Harry.

"I thought you'd wanted me to suck your cock? " I said.

"I bet you'd fucking love that wouldn't you, get the fuck over here." said Harry, and as I looked up I felt Harry's hands wrap around my ears and guide my mouth over onto his cock, pushing in as far as he could immediately, before I gagged on his hardening cock.

"Bet you fucking love that fag boy. And to answer your earlier question, you won't be sucking my cock today. No today I'm going to be fucking your mouth pussy until I'm satisfied. You're going to kneel there and take it, because you want to take it. Because you never feel as alive as when my cock is pushing it's way down your throat. Go ahead gag all you want, I'm not going to stop." growled Harry as he mercilessly face fucked me.

I knelt there, mouth open, giving myself to Harry. I didn't really know what to do with my hands as the last time I sucked cock I was in handcuffs. I could play with myself, but despite the urge I decided not to as I guessed that's not what Harry wanted. I could maybe put my hand on his hips or try cup his ass, but Harry's much bigger arms were in my way, so in the end I settled for hands behind my back like I was still handcuffed, it felt more familiar this way.

After a few more minutes I felt Harry slowly withdraw from my mouth. "Get up and bend over my desk now" said Harry.

I quickly did as told, I felt so excited and nervous. Next thing I felt the familiar feeling of lube being applied to my ass, followed shortly after by a slight pressure and then a pop. Harry had inserted the head of the lube bottle up my ass and then proceeded to squeeze a large amount of lube directly into my rectum. I expected some other object to penetrate me after the bottle was withdrawn but to be surprise nothing happened.

"Back on your knees bitch." said Harry. And again I quickly complied, head down this time.

"Now while I'm certain you'd love nothing more than my cock in your mouth again, I have other plans for you this time." said Harry. I could see his feet moving around, and doing something, finally I felt a tug on my dog collar, pulling me forward and up, I looked up to see Harry's ass less than a foot from my face. He didn't need to tell me what to do next, I had my tongue out and aimed for his asshole before we even got cheek to cheek. I went as deep as I could with my tongue. As I did I got the distinct taste of that strawberry lube that was on the dildo that I'd done ass to mouth on last week. Harry must have been planning on this surprise I'd guessed. I licked his ass like my life depended on it. Fast strokes, slow deep strokes, I did them all. Harry hardly needed to pull on the leash at all, I knew he was getting off from the sounds coming out of him, and I loved that.

After some unknown period of time Harry stepped away. Wordlessly he pulled me up and bent me over the desk again. I was excited about what might be going up my ass next. Maybe it was a butt plug, or a vibrator, I'd never had those up my ass before.

Then I felt what could only be Harry's cock at my entrance, he was hardly going to try fuck me with nothing other than his finger in my ass to open me up was he?

Oh you bet he was. I felt his hands press down on my back as he pushed forward. That now familiar pressure built and built, I felt like I was giving birth in reverse. After about a minute of intense screaming from me I finally felt the head of Harry's cock break through. Mercifully his cock felt like it was coated in a thick amount of lube, maybe Harry had applied it while I was licking his ass? Either way I was grateful for that small comfort. His cock felt even bigger now that I was bent over. Relentlessly Harry pushed forward, my moans seemed to be enticing him on. Once I felt Harry's balls against my ass I was mildly relieved, this was as tough as it got. But as soon as he was balls deep, Harry withdrew partially, and then began to fuck me harder and faster than he had last week.

"Oh god, that's too much, oh fuck, that's too hard, slow down." I moaned and pleaded.

"Shut the fuck up bitch." said Harry, and with that I felt a leather ball gag stuffed in my mouth, and wrapped tightly around the back of my head. This muffled the moans coming out of me, Harry seemed intent on using me hard, weather I liked it or not. I wasn't taking it in the ass, I was getting it in the ass.

"Yeah that's it, this is what sissy thieves like you get. You get your tight little asses ploughed. I should be allowed to fuck all you shoplifters like this, there'd be no more open stealing in my store. Well except you, you'd likely be waiting for the store to open so you could go in, steal something, and then get your anal fix wouldn't you, you filthy tramp." said Harry as he fucked me.

Harry was relentless, pounding away with abandon. The pressure was still intense around my anus, but at least the pain had reduced slightly. Again I thought about how I looked, dressed up like some slut, my clear heels, my "sissy slut" bra, my make up, my whole outfit, and how fuckable I must have looked. I even went to jerk my cock, but Harry grabbed my hands and put them behind my back, holding them down with one hand.

"Look at you moan like a slut, I can hear you through the gag, you're fucking loving this aren't you? I have you bent over my desk, dressed in full sissy uniform, and I'm pounding you in your ass. And you're full Oliver Twist "Please Sir, I want some more". You're such a submissive little faggot aren't you? Now listen bitch boy, I'm getting close to cumming, and I'm going to cum in your ass......unless you get on your knees and suck my cock straight out of your ass, only that way do you get the chance to swallow my cum again, understand?" he said.

Slowly, Harry mercifully withdrew his cock from my ass. I lay there, I was curious what it would feel like to have Harry cum in my ass. I felt Harry untie my gag, unsure what he was doing, I was about to turn around when I felt Harry's cock pushed aggressively all the way back up my ass in one go. Harry then started absolutely pounding me, my yelps and moans falling on deaf ears.

"Listen bitch, when I offer you the chance to swallow my cum you swallow it, understand? Now tell me you want my cock in your mouth." ordered Harry.

"Ahh, I want your cock in my mouth." I moaned.

"Say I want to taste my ass off your cock." said Harry.

"Please, I want to taste my ass off your cock." I shouted.

"Good, now suck me bitch." said Harry.

As soon I felt Harry's cock pop out of my ass I turned around and got on my knees. Harry immediately gripped my face and forced his cock hard and fast down my throat.

"Oh yeah that's better bitch. You're such a submissive slut, I should make you swallow every load I make, bet you'd love that, the constant taste of my cum on your breath, ooh fuck here it comes bitch, don't miss a drop." moaned Harry.

Harry's cum arrived thick and fast. I was able to swallow it all with his cock still in my mouth. I decided to keep sucking until Harry pulled out, so he wouldn't become annoyed with me again.

After a while Harry withdrew and I stared up at Harry, awaiting his next order.

Now bitch take your panties off, and close your eyes, it's time for your reward. Again I did as told. I heard Harry move around a little before he back over to me. It felt like he was going to give me a hand job but he seemed to be doing it wrong or something, I really wasn't sure what he was doing. "Right, now you can open your eyes bitch. If you look down you will see what is called a chastity cage on your little cock. Your ass was too tight tonight, you have not been loosening up during the week as ordered. For the week coming you will be able to focus on your ass without your cock getting in the way. I will give you some butt plugs which you must use everyday, and I'll know if you have missed any days. You are also to only wear thongs from now on, even when you're not here. That feeling of the thong riding up your ass will focus your mind on making sure your ass is in correct shape for what I have in store for you." explained Harry.