Chapter 1

“It’s been a while since I’ve done this,” I said softly. There was a touch of nervousness in my voice, but I tried to mask it.

“I’ll take it slow then,” he said reassuringly, flashing a sweet little smile. He looked so handsome standing there in the doorway of my bedroom unbuttoning his shirt. He never broke eye contact and it made me feel at once comforted and vulnerable, like he was staring into my soul.

I was laying on the bed, my shirt already off. I had thrown it on the floor as I excitedly ran into the bedroom. I had been so thrilled to see him that I wanted to immediately give myself to him. I barely gave him time to come in and take his shoes off before running to the bedroom. I had decided long before he showed up at my door that tonight he was going to fuck me. I was mentally prepared and - after a long time of not having sex - I was so ready for it.

His name was Sam Winchester. I knew very little about him other than that he was hot as hell and that he was 31, the same age as me. But I assumed he probably had more sexual experience than me. Most people did. It’s not that I was a virgin or anything, but sex wasn’t usually something I sought out. It was unlike me to have sex with a stranger, but Sam just made me so horny I couldn’t help myself.

He tossed his shirt to the ground and came over to the bed. He climbed on top of me gingerly as though he were scared he might hurt me and started kissing me passionately. He pressed his pelvis against mine. I was yearning for him to be inside me, cursing both our jeans for being in the way. Finally, at long last, he got off me and undid my jeans. He took them off and tossed them to the bedroom floor.

He pulled off my boxers. I expected him to be surprised because I never told him I was transgender. But if he was confused he didn’t say anything about it. Without missing a beat, he put his face between my legs and began kissing my clit. Then he began sucking on it a little bit. Finally, his tongue began working its magic and he ate me like he was ravenous. I moaned and my whole body tensed and relaxed as waves of pleasure rolled over me. I ran my hands through his thick hair and watched as he went to town on me. He stuck a finger in and my pussy gripped it tight. But I was so wet that it slid in and out of me with ease. I was almost shaking with satisfaction.

He began to unbutton his jeans.

“Are you sure you want this?”

I nodded. I wanted it so bad I couldn’t even speak. I was so wet I couldn’t believe it. All I wanted in that moment was to feel him inside of me.

He took off his pants and boxers. His cock was so hard. It was bigger than I expected it to be, thicker too. He rubbed it and looked down at my body with hunger in his eyes.

Once again he climbed on top of me and kissed me softly.

“I’m going to put it in now, okay?”

“Okay,” I responded.

I felt his cock rub against my clit. Then he moved it down to my pussy, dripping wet with anticipation. He put the tip in me and I moaned. I grabbed onto him and pulled him closer to me. Slowly, he sunk deeper and deeper into me. I could feel my little pussy stretching. He was so thick, I felt full, like if he was any thicker I wouldn’t be able to handle it. I felt every inch of him slide into me. Once he was all the way in, it felt like his cock was all the way up in my belly. I could feel him behind my bellybutton, filling me up with his cock. I felt full and stretched and soaking wet and my pussy devoured him like it was starving.

He kissed me again as he slowly began moving himself in and out of me with long, deep strokes. I moaned as I kissed him, losing myself in the pleasure. My little pussy could barely take it. The fullness I felt between my legs made me begin to panic. Part of me was scared he might “ruin” me. I knew that whole notion was archaic and not based in fact, but it scared me nonetheless.

Panicked, I said to him, “You’re stretching my little pussy. You’re going to ruin it.”

“Shhh it’s okay,” he whispered. “You won’t be ruined, your little pussy is elastic. It stretches, that’s what it does. You will be okay.”

He kissed my forehead and pulled out of me.

“No, no, please, put it back in. You feel so good in me, I need it,” I begged.

He slid himself back in me with a cute little smile. He kissed my forehead again as he thrusted. He started off slow, but began to fuck me a little faster, a little harder. It felt so good.

I couldn’t shake the thought that he might ruin me. It lingered in the back of my mind, but it almost felt good. Part of me liked the idea of his cock fucking me up, stretching me out. I wanted him to gape me. I wanted him to open me up so wide he could see inside me when he was done. I wanted him to go ham on it.

“Faster. Harder.”

He silently obeyed. He began fucking me so fast and so hard I could barely believe it. The pleasure shook my body, my muscles tensing up reflexively. I moaned louder and louder. He began fucking me so ferociously I thought I might rip right open. But that thought excited me. I looked into his eyes and he smiled to reassure me. I smiled back. I could feel his body growing tired, but he persisted.

“My poor little pussy, it can barely take it,” I whispered. “I want you to gape me. Fuck me as hard as you can for as long as you can until I can’t take it anymore.”

“You feel so good, oh my God,” he whispered back as he continued to go even harder, even faster, even deeper than I thought possible. He kissed my neck and I held tightly onto him.

Finally I felt my pussy begin to ache. It screamed at me, it said, “Please, I can’t take this anymore!”

“Stop, stop,” I breathed into his ear. Immediately, he stopped. I could hear him panting as he lay there on top of me, completely still. I held him tight and thanked him breathlessly.

“Keep going,” I urged.

He began fucking me gently and kissed me. I worked my clit as he plunged himself into me, then slid himself almost out of me over and over again.

“I just came,” he said sheepishly.

“Can you keep going for another minute or so?”

“Yes.”

“Will it hurt you?” I asked.

He chuckled, “No, no. I’ll be fine.”

He fucked me and stared into my eyes with a warm expression. I felt the orgasm coming. It crept up slowly until I felt it arrive with a bang. I moaned as it came over me. It was overwhelming how good it felt. It was the best orgasm I’d ever had and it left me limp and breathless.

He kissed me on the forehead once more before sliding out of me and laying down next to me. He held me tight.

“You made me feel so good. Your pussy is so nice,” he said.

I was silent.

I slid a finger inside of my pussy. It was gaped. It was opened so wide it felt like it was yawning. I slid another finger in. Then a third. I was so wet, I couldn’t tell what was me and what was cum. I tried for a fourth finger but it wouldn’t go in. Still, three felt like too many and I became scared that it may never go back to how it was before he entered me. I knew the fear was irrational, but I couldn’t help it. I felt ashamed, guilty and dirty.

I had a flashback. I remembered the man who had held me against my will when I was a teenager. He had raped me repeatedly and he always told me I was loose. He said my pussy was gross and stretched out. He would tell me that I didn’t make him feel good. He always made me feel so small and he had left me feeling self-conscious about my pussy. He had convinced me that it wasn’t good enough.

I suddenly began to violently sob.

“What’s wrong? Did I hurt you?” He squeezed me tighter, his voice filled with concern. “I went too hard, didn’t I?”

“No, you made me feel really good,” I sobbed. “I just ... have some mental issues. I’m sorry.”

“Don’t apologize. Tell me how I can help.”

I wrapped my arms around him and cried into his muscular chest. He stroked my hair. I began to feel better. I felt whole. I felt loved. I felt good enough.

The next morning I awoke to the smell of pancakes. I went into the kitchen and found him making breakfast.

“I found your pancake mix. I hope you don’t mind me using your kitchen,” he said, smiling at me.

My heart melted. I had never had a man make me breakfast before. I kind of expected him to be gone, having snuck out of my apartment in the night while I was sleeping. But he was still there.

He plated the pancakes and went to sit at the table when I grabbed his arm and pulled him away from the table. I got down on my knees and began taking off his pants.

“What are you doing?” He seemed confused.

“I’m thanking you for making me feel good.”

“That’s not necessary. You made me feel equally good.”

“But I want to do this.”

“Can I eat you out after then?”

“Okay, but not immediately after. Maybe later today or some other day. Orgasms take a lot out of me and I don’t think I can handle another one right now.”

“Okay.”

I finished taking off his pants and boxers and his cock lay half-limp in front of my face. I began licking the tip, then the shaft. I spat on it and began rubbing it. It quickly hardened in my hand. I tickled the tip with my tongue a little to tease him before putting the tip in my mouth. I worked the tip for a while before sliding his cock deeper into my mouth. I could feel it in my throat and I struggled to get all of him in my mouth. He was so thick I could barely get my mouth around it.

I tried not to gag as I put his cock deeper into my throat. I almost choked on it and slid it from my throat quickly and worked the tip some more. I looked up at him with his cock in my mouth and he smiled kindly at me.

“May I stroke your hair?”

“Yes,” I said.

He gently put his hand on my head and massaged my scalp with his fingertips as I went to town on him.

I sucked his dick for a few minutes before he said, “I’m going to cum.”

“Do you want to come on my face?” I asked.

“No, I’d like to come on your tongue if that’s okay?”

I stuck out my tongue as far as it would go and jerked him off for a few seconds before he grunted and came. His thick cum coated my tongue. I loved how it tasted, I wanted more of it. I wished he could produce a cup of cum for me to drink like a milkshake. The idea of filling up my tummy with his cum turned me on. I swallowed it. Then I kissed his tip and looked up at him. He looked tired, but grateful. I thanked him.

“No, thank YOU,” he said.

I stood and he wrapped his arms around me and held me tight for a few beats.

“I’m starving. Let’s eat,” I said, smiling broadly at him.

We ate our pancakes in silence. Sam kept looking at me as though he expected me to burst into tears at any moment, but I felt amazing. Normally I hated giving head because the man who had hurt me had loved shoving his cock down my throat and watching me choke and gag, but Sam’s cock felt good in my throat. Everything about the man sitting across from me at the table made me feel safe and horny.

Finally, Sam spoke. “So, how did you get into the business?”

He and I had been hunting the same group of vampires when we met. They had a den here in my city and I had been working to find it, but Sam and his brother Dean had beat me to it. By the time I arrived, they had just finished slaughtering all the vampires. I was disappointed, but that disappointment didn’t last long. One look at Sam and I was smitten. I introduced myself and he seemed to like me back, so I gave him my number.

I was almost shocked when he actually called later that day. I sort of expected him to throw my number out. But he wanted to meet me for coffee. But I didn’t want coffee, I wanted his body. I wanted him naked. I wanted him in me. I usually didn’t like sex because of the sexual trauma I’d endured when I was a teen, but he was just so sexy I couldn’t resist.

I asked him to come over, telling him over the phone my intentions. I told him that I wanted sex. I usually was quite shy, so the invitation surprised me when it came out of my mouth, but something about him drove me wild. He also seemed a little taken aback by my bluntness, but he shyly said he would enjoy that very much and agreed to come over.

“I was kidnapped by a demon when I was 19,” I told him. “Well, technically, it was a man possessed by a demon. I never really believed in demons or anything like that, but as soon as I saw the black eyes, I became a believer.”

“I’m so sorry.”

“It’s fine,” I lied. “It was a long time ago. Anyway, another hunter who lives in this city saved me and she taught me how to hunt. After what that demon did to me, I wanted vengeance. I wanted to kill every creature that causes harm to humans and I wanted to save people the way that hunter had saved me. How did you get into hunting?”

Sam told me his story. He and his brother had been raised by a hunter. His dad had - like me - wanted vengeance after his wife was murdered by a yellow-eyed demon named Azazel. I finished my pancakes as I listened to Sam tell me his story. He was clearly very strong and had been through a lot. I could see trauma in his eyes and it endeared me to him. It amazed me that someone who had endured so much suffering could come out the other side with so much empathy and tenderness.

“So do you and your brother live around here?” I asked. He shook his head.

“No, we travel a lot. We live in Kansas.”

“You’re a long way from home,” I noted. He nodded. A part of me ached thinking about how far away he lived. I would likely never see him again once he left and that thought depressed me. I wanted him to stay here with me. I had only just met him, but I was falling in love.

Suddenly, I was really horny. Thinking about him leaving made me want him. I may never have another chance to have his dick in me and I felt like I needed it more than I’ve ever needed anything.

“Let me know when you’re able to get hard again, I want to ride you like a pony,” I blurted out. He blushed slightly and smiled to himself.

“That sounds great, but I owe you oral. I want to pay you back for giving me that amazing blowjob. So let’s do that instead,” he suggested.

“Actually...” I hesitated. “I like getting eaten out, but I can’t come from oral. Don’t get me wrong, I’m not saying it doesn’t feel good. It feels really good, but it just won’t make me come.”

He looked a little disappointed so I felt like I had to explain further. “Most people, when I tell them that, say that I just haven’t been eaten out properly before and they swear they can make me come, but I promise you it’s not a skill issue. You’re VERY good at eating me out, it feels amazing. It’s not you, it’s me. I just can’t come from oral sex, I just can’t. And it’s not a trauma thing, either-”

“You don’t have to explain yourself so hard, it’s okay. I get it,” he interrupted. “If you say it won’t make you come, I believe you. If there’s something you don’t want to do sexually, I won’t make you do it. Period.”

I smiled. God, he was perfect. I felt myself getting wetter and wetter, soaking through my boxers. I was scared I’d leave a wet spot on the chair.

“Well, if there’s anything you don’t want to do, let me know, I also don’t want to make you do anything you’re uncomfortable with,” I said.

“Deal.”

“And if there’s anything that really turns you on, let me know. I want to make you feel good.”

“Meh,” he shrugged. “I just kind of like whatever. Truthfully, I mostly get off by knowing I can make my partner feel good.”

“Well then you should have no issues getting off with me. Your dick is magical, I swear. And you’re personality turns me on and, goodness, you’re just so freaking hot, I can barely handle it.”

“Speaking of handling it, are you sure you want to ride me? I don’t want to hurt you, I feel like I made you sore last night.”

“I’m a little sore,” I admitted. “But I can take more. I will try to go easy on my poor little pussy.” I laughed. Sam looked concerned. I added, “Seriously, don’t worry about me. I know my limits.”

“You were scared I stretched you out. I don’t want to make you feel ... bad. I think you might just be saying what you think I want to hear.”

“I’m not. And you did stretch me out, but it’s like you said. Pussies are very elastic. I’m just relieved that you aren’t disgusted by how wide you made me or anything like that. Like, I hope I can still make you feel good even though I’m a little less tight than I was last night.”

He looked offended. “If anything, you were too tight last night. It almost hurt me how tight you were squeezing me. It felt like your pussy was trying to push me out of you, it was trying to reject me. I don’t like that. I want to feel like you’re opening up to let me in, you know?”

I just nodded. He stood up and walked over to me. I stood up as well and we began making out. He had me so horned up I couldn’t wait for the bedroom. I tore off his clothes like I was jonesing for his body and began stroking him. I felt him growing harder in my hand and it made me so wet. I ripped off my clothes and went to put his dick in my mouth, but he stopped me.

“No,” he said quietly. “I want you to sit on my face.”

He laid down right there on the floor and waited for me to sit down. I had only ever sat on one person’s face and I felt guilty about it. I thought my thick, juicy thighs would crush him or suffocate him. But with Sam I knew he’d stop me if it wasn’t what he wanted. I knew he wasn’t just saying he wanted it to impress me, I believed him when he said he got off on making other people feel good. I felt the least self-conscious I’d ever felt while nude.

I sat down and he started going to town on me. I began grinding my pussy against his face. He had a little bit of stubble and it was kind of scratchy, but I loved how it felt.

“Can you put your tongue in me? I want you to fuck me with your tongue.”

Without saying anything he stuck his tongue deep inside my pussy. I could feel it wiggling around, licking my insides. I moaned.

I got off his face and went to go sit on his cock. He had been stroking it as he ate me so it was still standing tall. He looked me in the eye and asked me to kiss him before I sat on it. I made out with him, tasting my own pussy as I did so.

“You taste so good,” he told me. No one had ever told me that. I swooned.

I went to put him inside of me, but he stopped me again.

“Wait,” he said. “Can I ... look at it?”

“It was just on your face, didn’t you get a look at it then?”

“Yeah, but ... I don’t know, I really just want to get a good look at it. Can you lay down for a sec and open your legs up wide for me?”

I hesitated, but then I did it. He put his face between my legs and stared at it. I felt a little uncomfortable. I was very aware of how it smelled (it smelled normal, but I was still scared he might not like it) and I was sort of self-conscious about how it looked. He stroked himself as he inspected it.

The demon who had held me against my will had inspected me sometimes. He would tell me how gross and stretched out it looked and would accuse me of sleeping with people who weren’t him even though he literally never let me leave his side. He would call me all sorts of hideous names. My PTSD began flaring up.

“I don’t like this,” I said to Sam.

He looked at me and apologized. “It’s just so pretty. Sorry, I mean handsome.”

“R-really?”

“Yeah, it’s so sexy.”

“You really like it?”

“I love it.”

“You can call it pretty. It’s okay. I like the idea of having a pretty pussy.” He then stuck two fingers in me and I winced.

“I’m trying to prepare your pussy for my dick,” he explained. “Does it hurt?”

“No, it just surprised me.”

My pussy was tighter than it had been the night before after he pounded it. It had shrunk back down to its regular size and his fingers made me feel like I was going to tear.

“You really are very tight. I don’t want my dick to hurt you. So I’m just trying to open you up a little, stretch you out so you can handle me inside you.”

“That’s ... very sweet.”

He wiggled his fingers in me as I played with my clit. Then he tried to slip in a third finger, telling me to relax and stop squeezing. I did as he said and he was able to get the third finger in me. It didn’t hurt, it actually felt really good.

“I think I like being stretched,” I admitted.

“Well, good. Because my cock’s about to stretch your pretty little pussy all the way out. Are you ready?”

“Yes, sir,” I answered, smiling the kind of smile you only get when you’re in love.

He laid back down on the ground, stroking himself to ensure he was nice and hard for me. I straddled him and put his cock inside me. He slid into me easily, but my pussy still hugged him tight. I played with my clit as I bounced up and down. I rode that dick like a maniac, grinding on him until my legs were sore. His cock felt even better inside me than it did the night before somehow. I was overwhelmed with ecstasy. It was rapture. I moaned louder than I ever had before, I couldn’t help it.

“I want you to come deep inside me,” I whispered.

“I’m almost there.”

“Me, too.”

I kissed him as I rode him, a little slower now. I heard him grunt a little and I knew he was orgasming. I sat down on him, forcing his cock deep within me. I swore I could feel his load shooting out of him, filling me up. I wanted to be overflowing with his cum. I wanted to feel it dripping out of me for days and days. I wanted to keep some of him inside me forever. I came, violently. I let out a noise I’d never heard myself make before, the sound of pure pleasure and delight.

I needed him to stay with me. I kissed him passionately, thinking it might be my last chance to taste him, to feel his lips on mine, to have my pussy stretched around his cock. I couldn’t bear the thought of it. I needed him like I needed air.

I got off him and we cuddled there on the floor for what seemed like an eternity. A blissful eternity that somehow wasn’t long enough. We were both silent.

I’m the one who broke the silence. “We should shower. I’m so sweaty.”

He agreed and we showered together. Mostly in silence, save for him asking me to hand him the soap. Silence with him didn’t feel uncomfortable. It felt calming. It felt serene.

“Fuck it,” I said as soon as we got out of the shower. “I don’t care if this is inappropriate to say or whatever. I think I’m falling in love with you, Sam. You’re seriously the perfect man and I would hate myself forever if I just let you walk out that door. I need to see you again. I need you to fuck me again. I need you in my life.”