A Sissies Dilemma Pt. 02

Chris pulled his trousers back up, still standing directly in front of me, whilst I just wished he would go now he'd had his fun. As he stood there I could see his eyes roving over my body and sensed his satisfaction with how I now sat on the bed, silent tears still trickling down my face.

"You better get yourself cleaned up, a sissy should always look her best for her man" Chris said, before adding "and for the time being I'm your man, so don't try my patience."

My mind was racing, we'd had a deal and now he thought he could tell me what do, call himself my man, no way, no. I started to stand, wanting to at least pretend to seem confident and this way he wouldn't be looking down at me quite as much. I new what I wanted to do but after sitting with the dildo buried inside me for so long and wearing 5 inch heels things didn't go that way. Instead I stumbled forward, the dildo sliding out with a loud squelching pop, before Chris slipped one arm around my waist to hold me up. My legs felt like jelly and I ended up standing there leaning against him for support. Both his hands now cupped my buttocks, his index finger from each hand toying with my hole, slipping in and out of me.

Finally I managed to speak, my words coming out in gasps as he slid more fingers into me. "We had a deal, one blow job and that was it." I almost squealed the last word as a third finger entered me lifting me of my feet.

"NOW LISTEN, I will not remind you again that I could ruin you in this town with this video. No one is going to believe you were forced to do anything the way you look and you'd have to be stupid to think they would. Now clean yourself up, put on something pretty and I'll see you downstairs in 20 or we'll see how many likes this video gets."

With that his fingers slipped out of me leaving my boi pussy gaping and empty and I stumbled back to sit on the bed. By the time I looked up Chris was already leaving the room and a feeling of despair gripped me, as the realization I had no choice but to obey dawned on me. Maybe I could go along with it for now until I found some way out, some leverage of my own.

Even as I was thinking things over in my head I had started to strip off my cum stained outfit. Trying not to think about what might be to come I grabbed a pair of white stockings and quickly rolled them up, loving there silken feel. Clipping them on to a pastel pink suspender belt, I slipped the matching bralette on, enjoying how my nipples poked through the lacy material. The matching panties were lacey at the front with sheer nylon at the back making them see through, my boi pussy clearly visible. My white stripper shoes were next, making me wish I had bought some for walking in, not just for looking sexy. Finally I slipped into a white shear stretch nylon dress, which meant you could still see everything but offered a little bit more protection, hopefully.

I'd removed my make-up and the cum from myself with wet wipes and now set about trying to give myself a girly appearance, less sexual and more innocent. Pink lipstick with a high gloss, followed by some lightly applied pink eyeshadow was next. A little mascara to to help make my eyes pop and a younger, pretty girl looked back at me from my mirror. Finally I put my hair in two plaits which fell to just above my collar bone, a pink ribbon bow holding them in place. Looking at myself in the mirror I felt that horny tingle run through me, no matter why I was dressing just the act alone aroused me and I gave a sexy shimmy and a smiling sissy looked back at me, Just I was about head down I saw my jewelry and decided why not, being totally femme just made me feel good. Putting a silver ankle chain with a little bell attached on I enjoyed the tinkle it made as I walked out my door.

This was the first time I'd actually left my room dressed up and I felt odd walking down the stairs, like I didn't actually belong here. Luckily our house was on a large block so no neighbors over looked us, but it was a large house, which seemed bigger when your tottering on 5 inch heels. My mum had turned the house into a bed and breakfast years ago when my father left, but happily no guests were staying or expected soon.

Opening the door to the lounge panic gripped me as fear and doubt flooded through me, hating having no control over my fate. Chris was sitting on the sofa looking relaxed, as though force fucking someone's face was an everyday occurrence.

"Come in now and let me look at you," he said, his tone softer, almost kindly.

Walking in I tried to concentrate on my strut, something about being dressed made me want to perform, regardless of what he'd done to me. My confidence in my ability to walk was increasing and I gave a little cat walk performance before coming to a halt standing in front of him.

"Very good, you look really pretty and I'm glad you decided to do the right thing and go with it. I'm sure that given time you'll come to appreciate this moment as when you finally became your true self. Now sit down next to me and have a drink and relax, I've got some news for you."

Even sitting down seemed fraught with danger, to far from him and he might be offended, but to close could send the wrong message. In the end it didn't matter as he guided me close to him, our thighs brushing against each other. He handed me a drink, white wine, something I wasn't used to and clinked his glass against mine.

As I took a little sip Chris slowly rested his hand on my thigh, his fingertips lightly caressing the silken material from my knee to the stocking top. The stroking was having a relaxing effect, and finally being dressed with some one else present was a strangely uplifting experience.

Chris's voice brought me back to my senses, "your mother has had to go and look after her sister, some family crisis, so she asked me to look after the business while she's away. She did try to contact you but you were a little pre-occupied, lets say. So while she's away I'm in charge as we both know she doesn't trust you with the financial side of things, or the organizational side. But now I know your secret I'm a little bit more than in charge, I own you and if you're really good when your mother gets back you get your life back, if you want it. I never want to have to remind you again what will happen if you disobey, that will get tiresome so here's the deal. That video will automatically send at 10 pm each day unless I enter a cancellation code and that all depends on you being a good sissy."

The words slowly sank in, my mind racing trying to process all the different ramifications. I quickly drained my glass still unsure what I should say, knowing I should stand up for myself.

Chris filled up my glass once more. "Say thank you daddy," you should always be grateful for everything I do for you and to you."

Gulping down the wine for courage I blurted out" no I won't, I can't do this" before trying to stand and leave the room. I don't know if it was the shoes or the wine but standing proved almost impossible, a vague dullness coming over me.

Chris had grabbed me by the wrist and now I found myself face down over his lap. I had no energy to struggle as his palm came down on my ass cheek, the pain causing me to shriek and see stars. Again his hand came down, even harder if that was possible but on the other cheek and a sob escaped my lips. A brief pause made me think that might be it until I felt him push my dress up, only to then feel him pull my panties down to my stocking tops. The beating continued and my cries got louder as my ass felt like it was being branded. All this time his other hand pulled my head up by my pigtails making me look into the camera he had positioned on the sideboard.

"I'm sorry daddy, I promise I'll be a good girl, please let me be your good girl." The words came out in a jumble between sobs as he continued to show no sign of stopping.

"Please daddy I just want to learn how to be a proper sissy girl for you, I'll do anything, anything you want."

The spanking stopped and his hand started softly caressing my pink and now ultra sensitive cheeks, but still he held my head up.

"Now I want you to look into the camera and tell me all about yourself, the facts and the fantasies as if you were on some sort of sissy dating site. Remember you know what men like to hear, I'm sure you've watched enough sissy porn not to be stuck for words. If your really good I'll even give you a special treat baby girl, one you'll absolutely love."

Chris's words sounded blurred, like they were coming from far away, but he sounded so kind and sincere I just wanted to please him, and who doesn't love a treat. Trying to focus on the camera I started to giggle as Chris's fingers started to probe my hole, causing a feeling of ecstasy to flood through me. I was enjoying it so much I even started to move backwards and forwards on his fingers, wishing they would go deeper inside me.

"Hi guys," I started, keeping my voice as girly as possible, "I'm sammantha. I'm 18 and single and have a petite slim body with long blondish hair and blue eyes. I've got full lips and long toned legs that end in a pert round butt and I'm smooth all over." The words were tumbling out and I was enjoying my role and the honesty it allowed. I was also really enjoying the sensations flowing through me as Chris's fingers found spots inside me I didn't know existed, causing me to gasp and sigh with pleasure.

"I love to dress in lingerie and sexy costumes and feel so happy when I'm transformed into sissy slut with my hair and make up done. I guess I've fantasized about being with guys when watching porn. How they'd fuck me and humiliate me with there friends, leaving me a cum drenched sissy, but all I have really done is be face fucked once. I definitely feel very submissive when dressed up and know the right guy or guys could do what they like to me once I'm properly trained. Hope you find me to your liking and who knows what could happen, see ya."

"Was that okay daddy?" I asked Chris, struggling to understand what I was doing, whilst feeling so happy.

"That was really good and it sounded like you're trying to become who you really are. Sometimes all it takes is something to help you relax and let go of your inhibitions, a little something extra in your wine."

"Now I want you to carry on facing the camera on your hands and knees and I'll give you your treat, but it's just this once for being such a good sissy."

Looking over my shoulder I watched as Chris stripped off his clothes, his body was muscular and solid, and I realized he was a real man and I would never be one. He gave my bum a playful slap, not to hurt me but just to tease me a bit. As he got behind me I suddenly became scared thinking this isn't going to be a treat but torture when I felt his breath on my butt, his tongue slowly probing the outer edge of my hole. I gasped with delight, I'd never felt anything so good as this. His tongue lapped around the edge occasionally darting inside me, his hands spreading my cheeks, making my hole gape open wider.

His right hand appeared at the edge of my vision, the musky smell of my ass alerting me to it's presence and I new what good sissy should do. Turning my head I obediently opened my mouth, eager to taste his fingers and clean them with my tongue. They tasted unpleasant, but not disgusting, and I think that's what turned me on more as I sucked greedily on them.

My moans were filling the room, alternating with gasps as he bit and nibbled on my butt cheeks. I wanted so much for his tongue to be deeper inside me I started to beg, "please daddy tongue fuck your sissy, your making me so wet, please."

His tongue was twirling inside me, stars were flashing in front of my eyes and my clitty felt ready to explode. I couldn't even call it a cockette after having a real man in my mouth, so cliitty it was. Streams of pre-cum were leaking from me, staining the cushions with large sticky patches, as I gyrated my ass on Chris's face.

Suddenly his tonguing stopped and the only noise was me panting for breath. I could feel Chris change position, grabbing my hands and placing them on my own butt cheeks.

"Spread your cheeks for me Sammantha, be a good girl for daddy," Chris commanded.

Without even thinking I pulled them hard apart, feeling my hole gape slightly, fluttering open and closed with my rapid breathing. Chris pushed down on my lower back, my position now classic doggy with my asshole the perfect height for what was coming. At the same time I could feel his swollen knob pressing against my opening, my hole now slick with spit and pre-cum.

"Well Sammantha what do you want now. All dressed up in your white lingerie like a virgin bride, what's it to be."

Pushing back against Chris's cock I started to feel myself stretching more than I'd ever been with any toy. Trying to give myself time to relax, I slowly rocked back and forth with just his knob inside me, feeling the fine line between pleasure and pain.

"Oh god daddy your cocks so big, I'm scared it's going to damage me but it feels sooo nice."

Chris leaned forward enough to grab a pigtail in each hand, the movement causing his cock to slide a little deeper in me and my squeal to fill the room. His grip on my hair tightened like he was holding a horses reins, the pain causing me to forget his cock inside me.

"I've been nice, now its time for my treat, Sammantha. Sissies don't get to choose how there fucked, or when there fucked, they just have to remember to say thank you afterwards."

With that Chris pulled hard on my pigtails and thrust his cock inside me, going so deep his body slapped against my ass cheeks, the stinging from the spanking rekindled. My scream would have been heard from every room in the house, tears immediately filling my eyes and streaming down my cheeks. My back was arching from the force of him pulling on my hair and the only way to stop the pain was to try to press myself back on to him. Chris's cock was now totally inside me and I could feel his balls slap against me with every push forward. He stopped moving in and out and started to grind against me, making his cock seem deeper inside me, whilst also stretching my hole with his circular motion. Trying to be clever I started to move with him, thinking this would stop the stretching, but also because the sensation was beginning to feel pleasant.

My cries of pain were starting to be replaced by moans of pleasure and sighs of delight, all of which I seemed to have no control over. The sissy in me was loving being a real mans plaything, but in the back of my mind I new this wasn't consensual but couldn't seem to put the words together to object.

I had become so aroused by the sensations coursing through me that it dawned on me Chris had stopped moving and like a good sissy I had continued to grind against him. His grip on my hair had loosened a little so I started to slide forward off his cock, only to feel his grip tighten again. Knowing what I had to do I slid back, feeling his cock fill me again, only to feel his grip loosen allowing me to slide forward once more. His hand signals were like a form of training as I continued to slide backwards and forwards, until he had me riding his cock. Then he started to thrust again, meeting my backwards movement and it dawned on me he wasn't forcing me, I was totally involved.

Chris's speed started to increase and I adjusted to meet him, loving the feeling of his cock inside me. My own little clitty felt like it wanted to explode and I started to push back harder and faster, trying to get his cock to push against whatever it was that felt so good His right hand released my pigtail and I felt a sharp sting as he slapped my cheek, though now in the height of pleasure it only added to the experience. His left hand let go of the pigtail and went around my throat, controlling my breathing and making me dizzy.

Chris was now slamming into me, an animal in a frenzy with no concern apart from personnel satisfaction. Each thrust lifted me off the sofa pushing me forward until I was jammed in the corner, unable to move, his whole bodyweight on top of me. I continued to grind back against him and finally I felt my whole body convulse. the biggest orgasm of my life tearing through me. The orgasm caused my hole to tighten and Chris let out a roar as I felt his cum flood inside me. He continued to push himself as deep into me as possible, his cock throbbing as jet after jet of cum emptied into my boi pussy.

Chris pulled his cock out, and I felt a great tiredness start to envelope me, my orgasm robbing me of any remaining energy. I was still looking at the camera, not quite understanding how I'd become such a sissy slut, when Chris stood up and walked around the sofa, his cock now dangling in front of my face.

I new immediately what was expected and wrapped my lips around him, sucking him into my mouth, still looking into the camera. I swirled my tongue around every bit of his cock, the taste of my own ass so strong it made me gag a little. There was also a coppery taste mixed in with it and as he popped out of my mouth I realized it was probably blood. Holding his softening cock in my hand I stared up into his smiling face and said what I new he'd want to hear. "Thank you for fucking me daddy, I'm not a virgin anymore, I hope I pleased you."

Chris smiled down at me, "not bad for your first time and it's certainly not going to be your last."

To be continued