My Sissy Awakening 02

So it was Saturday night, and I was on a bus on my way to Harry's house.

The last couple of days had been something a bit different. Thanks to a simple mix up I'd discovered that I had something of an interest in being dressed like a slutty woman, and then getting on my knees to swallow the cum of a basic stranger to me.

Then to add to that, I'd spent the last couple days where possible dressed in my new slutty lingerie putting various items up my ass, as I watched a whole new branch of porn I'd previously never knew existed, sissy porn. I watched various twinks and subs suck, lick, and fuck anything that moved, all the while dressed in various degrading and whorish outfits.

I'd also been messaging Harry ever since our time together on Tuesday morning. We'd discussed some of the things I'd seen in the porn videos, and I kept him abreast of my anal antics. I'd been using various items to loosen up my butt. I'd used the butt plugg that Harry gave me, my own fingers of course, and I even managed to fit a small carrot up my ass last night.

We'd also discussed our plans for tonight. Harry didn't give much away, but he did say that tonight we'd be doing a roleplay. He was going to be a leading sex therapist and I was a rich young man who needed help as he was worried his new desires were wrong and should be suppressed.

I'd spent the afternoon getting ready. I'd gotten a body wax done at a local salon, I'd done some more reading on some things that might happen tonight, and finally just before leaving I'd done an enema on myself to clear myself out in case we got up to butt stuff tonight. I didn't think we would given the size of Harry's cock in comparison to my virgin asshole, but I thought better safe than sorry.

My heart was pounding as I approached Harry's House. It was a large two story house, surrounded by trees, with a large wooden deck out the side. If the inside was even half as nice as the outside then I'd be spending the evening in luxury. Palms sweating, I knocked on the door.

Harry answered the door with a big smile on his face. "Ah Mr Molloy, nice to meet you. I'm Dr Aikan please come in." said Harry. I guess he was going for roleplay right from the start. Playing along I replied "thanks for seeing me at such short notice Doctor." I said.

"We'll go straight to my office so." said Harry. He lead me through an entrance hall, and into a large open plan living room. There was a glass ceiling and glass on one other wall also, so the room was bright and summery. We continued on to an office off the living room. It had two comfy chairs, mahogany table, and books on the wall. It actually looked like a real doctors office.

"Take a seat please Joey." said Harry. "So how can I help you today?" he said.

"Well doc, I've been having these urges lately. I've never had them before, but now they're very strong." I said.

"Well you've come to the right place. Sexual pathology is my speciality. Why don't you give me some more detail about your urges and we can explore them together to find a solution that works for you, sound good?" said Harry.

"Yep great. So basically I've always seen myself as straight, sexually attracted to women. But recently I've had an overwhelming urge to dress in slutty women's clothing. And once I'm dressed like that, I have this huge urge to suck another mans cock and then have him bend me over and shove it up my ass. And I'm a virgin doc so even though I know it would hurt like hell I still really want to do it, is this normal?" I asked, really liking the tension all this creates, as honestly I was still wrapped internally about the events of the past week.

"Well, a healthy sexual curiosity is nothing to be ashamed of. But when it takes over your life, it can become pathological. Tell me about these thoughts in a little more detail and I may be able to let you know which side you fall into." said Harry.

"Sounds good. So I've been picturing myself in panties, bras, stockings, makeup, wigs. I'm a schoolgirl, a nurse, a maid, even a kidnap victim. I'm sucking dick, I'm licking balls, I'm getting bent over, I'm getting spanked, I'm getting tied up, I'm getting assfucked, and even though it hurts I still don't want it to stop." I breathe, talking rapidly.

"Hmmm, those are quite significant thoughts, but still could be perfectly normal. I think it might be good to see these feelings manifest themselves here and now to get the best look at what we're dealing with. Let's see.... yes these should do, when you hold these how does it make you feel?" said Harry, he'd handed me a red glittery thong and padded bra.

"Like I should get naked and put them on for you." I said.

"Ok, do that so." He said. I put them on, much quicker than my first time wearing panties earlier in the week.

"Now, do you feel any different?" asked Harry.

"I do, with the thong on, I want to bend over and show you my ass, and I didn't feel like that a minute ago." I said.

""Fascinating, I'd like to test something. Put these on too." said Harry, and this time he handed me a short black leather mini skirt, along with black thigh high boots. I put them on excitedly, curious as to how they felt.

And now, do you still want to stick your ass?" asked Harry.

"I do, I also feel I want you to put your penis into my mouth and ass, and humiliate me in ways I'm not even aware of." I replied candidly. I also placed my hands on the desk, which helped me stick my ass out sightly more than it was currently.

"Well I think I know the result of this, but still I feel like we should complete test-1 before commencing test-2. So put these on also." said Harry, as he handed me a tight black leather zip up jacket, a short black haired wig, dark red lipstick, and black eye liner. I put them all on, the eye liner taking me some, but I really enjoyed Harry eyeing me up like I was a piece of meat as I worked away, coating my eyelashes in whore paint.

"So phase one has clearly demonstrated an altered mental status towards homosexual intercourse when you're dressed in female garments. Now for phase two I want to examine where on the spectrum these exist. So I'm going to offer you a prize, you can have me put my penis in your mouth or in your ass (your choice). However, before that happens, you would first have to do a series of humiliating tasks. You may stop these tasks at any time, but of course if you do you will not get the chance to have my penis inside you. Sound good to you?" asked Harry.

"Yes doctor. I'm ready to be tested." I said, I felt so excited, but did my best to try hide it.

"Well to begin I would like you to bend forward and put your hands behind your back, I'm going to handcuff you." I did as told, the handcuffs felt cold on my skin, they must have been metal cuffs of some type.

"Now I'm going to put a ball gag in your mouth, then lift up your skirt and repeatedly spank you hard on your ass, you may either ask me to stop, or open your mouth and accept your fate." said Harry.

I opened my mouth and immediately felt a large gag shoved in my mouth and wrapped tightly around the back of my head, I really couldn't speak at all. Within seconds my skirt was up and the first smack beared down on my ass. I wanted to scream out but the gag stopped me. At least another ten smacks followed suit before Harry stopped. My ass was glowing, and a couple tears escaped me too. Harry removed the gag from my mouth before he spoke next.

"Now, I'm going to spank you again, but this time I'm going to put this gag in your mouth instead." said Harry as he held out what I recognised as a dildo mouth gag. The dildo was thick, black, and about 6 inches long. "Now I'm going to shove this in your mouth then spank you, unless you tell me not to." said Harry.

Silently I opened my mouth again. The gag took a while to go all the way in as I gagged and heaved once or twice, and it took a while for me to learn to breathe through my nose properly. I was only starting to get used to my new oral invader when the smacks started again. I winced and moaned like before, but the large gag in my mouth distracted me enough that the pain didn't feel as bad as the first round. After 10-15 smacks Harry stopped and I lay there, still dressed like a slut, bound, with a dildo forced down my throat. My thong covered ass was glowing red, and it wasn't over yet, and I didn't want it to either.

"So you've made it through the first two tests, this shows your level of humiliation appears to actually increase your level of sexual excitement, very interesting. However, this last task will test that theory. I'm going to take that dildo out of your mouth and force it up your ass, I won't stop unless you beg for mercy, but if you do then you fail the task." said Harry

Harry silently removed the dildo from my mouth, I could feel lube being applied to my hole, followed soon by the presence of the dildo at my entrance. Forward Harry pushed, the pressure was so intense. The was no getting away from it, this hurt. I kept myself from asking to stop by picturing how good my panty clad ass would look with a dildo in it. Eventually the head broke through, Harry pushed further inside, slowly inching further and further up towards my colon. I was just starting to wonder if Harry had switched the dildo for an even bigger one because this one felt like it was a foot long inside me, when mercifully I felt the base of the dildo push up against me. Harry held it there for a minute before slowly withdrawing it about half way, before again pushing it back in. He continued with this slow continuous motion for a few more minutes. I tried controlling my breathing to keep from screaming too much, reminding myself if I truly was a sissy then I'd have to get used to things going up my ass.

After one more motion Harry pushed the dildo all the way back in then stopped. "Well well, it appears you've passed all assigned tests. Now, what I should do is remove this dildo from your ass and allow you to claim your prize. But what I'm actually going to do is take this dildo out of your ass, and immediately I'm going to shove this dildo back down your throat. Of course you can stop this if you want, so the question is, are you about to go ass to mouth on this dildo just to finally have my cock inside you?" asked Harry.

I stayed silent. Internally I was wondering what I was about to do. But then I thought about it. I'd already gone through so much, I was dressed like a slutty prostitute, I was tied up and had just had my ass and mouth ravaged my this dildo. I was this close to Harry's cock, there was nothing else to do, so when the saw the dildo appear in front of my mouth I knew what I was going to go. I opened my mouth, stuck out my tongue, and did my best to keep eye contact with Harry.

Harry must have used flavoured lube, because I sensed strawberry tinge as the dildo was pushed back inside my mouth. This time Harry pushed deep and fast with the dildo, but I was ready for it. I was able to relax my throat, breathe through my nose, and let Harry fuck my face with the dildo until he was satisfied. After a few minutes he slowly withdrew the dildo as I lay there, excitement coursing through me about what was to happen next.

"So Joey, I think we've been able to establish a few things. Dressing like a sissy slut, like you are right now certainly helps you embrace your homosexual side. Your desire to gratify your inner sissy appears strong, and makes you forgo your dignity in pursuit of cock. So finally we reach the final test. I don't normally do this, but in the interest of being thorough, I'm going to fuck you with my penis. I wish to see first hand how you react with an actual penis. And now for the important question, do you want me to fuck you in your mouth, or in your ass?" finished Harry.

I thought for a moment. Both sounded tempting, being ass fucked would be awesome, but it was already quite raw from the dildo and the spanking, whereas my mouth felt comparably unscathed by its earlier activities. "I want you to fuck my mouth until you cum please." I said finally.

"As you wish, get on your knees and you shall be fed so." said Harry.

I managed to get up off the table, which was harder than it sounds due to the handcuffs and heeled boots. Eventually, I was able to get on my knees, about a foot away from Harry's crotch.

Harry stood over me, I kept my head down, but I kept my eyes on his cock, I knew it was in there, and it'd be in my mouth soon.

Slowly Harry opened his belt and slid down his pants, this was followed soon by his boxers, revealing his big hardening cock. I leaned in, mouth open and took his head in my mouth. It felt oddly familiar to be sucking his cock, even though it was only my second time doing so.

While sucking I had time to take stock of some of my recent life choices. I noticed it wasn't as easy to bob up and down on Harry's cock with my hands tied behind my back. I could just about see my lipstick coated lips in front of my eyes, they looked they were made to have a cock between them. My bra was starting to ride up my back, my thigh high boots were starting to dig into my knees, and I could feel lube moving around my ass from when Harry dildoed me. That lubed ass feeling was making me feel really horny, and I could feel my cock straining for freedom from the thong I was still wearing. Thinking about it all, I concluded something that I didn't think I would today.

I removed Harry's cock from my mouth looked up at him and said "Dr Aikan I've changed my mind, I want you to fuck me in my ass please." I said.

"You do? Why did you change your mind?" said Harry.

"When on my knees I got the overwhelming feeling that your cock belonged in my ass more than my mouth. I want to feel your cock stretch my virgin ass, I want to whimper and moan as you pound me, I'm ready sir." I said

"Very well then, this way." said Harry. He helped me to my feet and walked me over to a small door off the office. Inside was what looked like a small bedroom, presumably a guest bedroom. Harry lead me over to a small double bed. He stopped and turned, silently eyeing me up and down. After a minute he spoke.

"Sit on the edge of the bed please, then lie down." said Harry, he also put a pillow under my butt, so my bound hands didn't dig into my back too much.

"Now, legs in the air." ordered Harry, and my legs rested against his shoulders. I could see Harry applying a thick smear of lube to his cock, then I felt him applying more to my ass after that. I suddenly felt very exposed, I could feel Harry's cock rubbing against my asshole, it felt so much bigger now than it did when it was in my mouth.

Without further words I felt Harry push forward. I'd researched online about how to accept things up my ass, I'd read about trying to relax your ass by mimicking the motion when your trying to push things out of your ass, I'd read about breathing, I'd read about taking it slow, and dome of these kinda worked well enough when I had the dildo inside me. But now as Harry was trying to push the head of his cock inside me, all that earlier advice seemed pointless. It was so big, there was no way this was ever going to fit. I was squeezing the pillow under me from the pressure. Maybe I wasn't meant to be an anal bottom after all. And then with one further push Harry was in, the pressure around my ass was still there, but at least the stretching had stopped.

I had also read that the main limiting factor with anal sex was the ability to penetrate the anus, and that the length of the cock going in didn't matter that much. Well I can say now that the person who wrote that has clearly never had an 8 inch cock up their ass before. By the time most of Harry was inside me I felt like he was touching a lung. Slowly he withdrew to give be a little relief, but moments later he was right back in there, filling me up again.

Harry probed away like this for a few minutes, I lay there wondering was this it, I mean I was able to do this I think, but it wasn't the amazing experience I'd pictured in my head. Then Harry did something to change that, while maintaining his hip motion Harry reached for my panties and ripped then aside, exposing my still hard cock. He gasped it with his still lubricated hand, and began to jerk me off in rhythm to his thrusts. Wow, this suddenly felt a whole lot different. All thoughts left my mind other than what Harry was doing, and how to get him to keep doing it. I wanted him to fuck me harder if it would get him wanking me more furiously.

"Oh doctor, that feels so good. I love your cock in my sissy ass, oh god don't stop." I said through gasps.

"Yeah I knew you'd like this. You sissy faggots are all the same. "Oh no it hurts blah blah blah" but as soon you get the slightest pleasure you're all like fill my bitch ass. I'm going going to fuck you like this over and over again you know. I'm going to dress you up in all kinds of sissy bitch clothes, I'm going to fuck you any way I want, I'm going to bring my friends over and we're going to spitroast you, and you're going to love it. Because this is where you belong, all tied up, with a cock in your ass, begging for more." Harry was really getting into this.

Harry continued for another few minutes like this, and I could feel my orgasm coming, I had no control over it. I couldn't move, I didn't want to move, Harry had complete control over me. With one final loud moan I let go. I felt the cum gush out of me. If I'd had my eyes open I'm sure I'd have seen it shooting from my cock. After another minute or two it died down, and I slowly came back to reality. Harry was still in my ass, and was looking down at me smiling.

"Thought we lost you there for a minute." He said laughing. "That was pretty hot, I won't be to much longer and I'll be cumming too I reckon." He continued.

I lay there, my brain all fog, but one thought did manage to make it all the way for processing. "I want you in my mouth, I want to swallow your cum please." I said needily.

Silently, Harry helped me up and back onto my knees. Harry had been considerate enough to have a condom on while he was in my ass, so it was an easy transition to make to oral. I wasted no time in getting as much of him into my mouth as possible. Glug glug glug I went. I knew Harry was close, so I refused to slow my rhythm. And sure enough, after a few minutes I heard those now familiar sounds, breathing, and moans that told me Harry was about to come. Feeling curious I decided push forward and have Harry as far down my throat as I could when he started to cum. I could feel the pulsating and there's was definitely something hitting the back of my throat, but I hardly tasted as cum. After about another minute Harry slowly withdrew. He promptly helped me to my feet, took off my handcuffs and gave me a big long kiss on the mouth.

"You did really well tonight, way better than I'd expected." said Harry. "How are you feeling." He asked.

"Very good, that definitely escalated quickly, I just kinda got lost in the moment." I replied.

"I agree, we can do more of that soon, but for now let's have a cuddle and a nap." said Harry, as he helped me into the bed, and got in behind me. His big arm wrapped around my body as I spooned back into him all happy and safe. I wanted this moment to last longer but within seconds the tiredness came on me as I began to fall asleep.