Sam Winchester's New Lover
Copyright© 2025 by TransCatMan
Chapter 2
Fan Fiction Sex Story: Chapter 2 - Sam Winchester meets and quickly falls for a hunter. His brother Dean doesn't approve.
Caution: This Fan Fiction Sex Story contains strong sexual content, including Ma/Fa Ma/Ma Gay BiSexual TransGender Fan Fiction Anal Sex Analingus Masturbation Oral Sex Pegging Sex Toys
After Dean left to run some errands, Sam and I immediately went to the bedroom. I offered to let him put it in my ass to pay him back for letting me peg him, but he said that he really liked how my pussy felt and that he’d fuck me in the ass some other time.
He fucked me doggy-style until I came. I began giving him head to finish him off. I played with his balls while I sucked his cock. He had hairy balls and I liked it. He didn’t shave off his pubes, but he did trim them a little bit.
I loved pubes. I had a full, thick bush. I had asked Sam if he minded and he said that he loved it.
I put his hairy balls in my mouth as I stroked him. He seemed to enjoy that. Then I shoved his cock all the way down my throat as deep as it would go and he came. I held back a gag as he shot his load down my throat.
We both collapsed onto the bed, exhausted. I ran my hand over his smooth chest, then I rubbed his abs. He was built like a god. I was so lucky to have his body all to myself, at least for the moment.
“Are you ... you know ... monogamous?” I asked quietly. I wanted him to myself, but I was open to polyamory or an open relationship.
“I don’t know.”
I decided not to push the conversation. We would decide what our relationship was another time. For now, we were happy and that’s what mattered.
I didn’t mind sharing him if that’s what he decided he wanted. I wasn’t super promiscuous so I didn’t see myself fucking anyone but him. After all, who could possibly be better in bed than Sam? Anyone else would be a disappointment. But if he wanted to sleep with other people, it felt almost selfish for me to keep him all to myself. I mean, his body and his ability to fuck were gifts that seemed like they needed to be shared with the world and not just kept for me.
I got out of bed and went to get a painkiller. I didn’t tell Sam how bad my head hurt from the concussion. I didn’t want him to worry about me. I wanted him to see me as strong. He kept asking me if I felt okay and it made me feel like a child. I liked him a lot, but I didn’t feel like he necessarily saw me as his equal and that bothered me.
I grabbed a painkiller from the bathroom and then headed out to the library to check out some of the books. When I got there, though, I found a strange man in a trench coat just sitting there. He looked at me with almost no expression on his face and said, “Who are you?”
“Umm ... I’m Sam’s ... friend. I’m Sylvester.”
I expected him to introduce himself, but he didn’t. He just sat there and stared at me with a blank face. I felt uncomfortable. After a long, weird silence, Sam entered the room. I let out a sigh of relief.
“Oh, hi Cas,” Sam said cheerfully. “Sylvester, this is Castiel. I told you about him.”
Suddenly, the strange man’s silence made sense. Sam had told me that Castiel lacked social skills. I felt immediately less threatened and relaxed a little bit. From what he’d told me, Castiel was a bit odd, but was a really nice guy. I had never been in the same room as an angel and I felt kind of starstruck by him.
“Hello, Castiel,” I said cheerfully, trying to make a good first impression. For some reason, I really wanted him to like me. But he continued to just stare at me. “Sam tells me you’re an angel. That’s really awesome.”
“Where’s Dean?” Castiel asked Sam, completely ignoring my attempt at starting a conversation with him. I felt a little rejected, but reminded myself that he wasn’t being rude, he was just socially unskilled.
“He’s running some errands. He should be back shortly. Do you have news for us? Something big going on in Heaven?”
“No. I just wanted to ... socialize,” he said as though the concept of socializing was completely foreign to him. “I’ve found myself with some free time.” Castiel spoke as though he’d never spoken to a human before. I found it kind of charming. I was quite drawn to him. He was also very attractive. He made me sort of horny. I felt ashamed by that, feeling like I was betraying Sam by being turned on by his friend. I knew I could never have sex with Castiel, that would absolutely be inappropriate and a horrible thing to do to Sam, but part of me definitely wanted to.
Then Dean strolled into the room and my horniness disappeared. As per usual, he had a smug look on his face that made me want to puke.
“Well, Sam, it looks like we’ve got ourselves a case,” Dean announced. “Hi, Cas. You got news for us?”
“No,” Castiel responded stoically.
“Well, okay then. Sam, let’s go.”
“Excuse me,” I said indignantly, “I’m coming, too.”
“No, you’re not,” Dean stated firmly.
“Yes. I. Am.”
There was a long pause. Dean looked annoyed. I expected Sam to pipe up and take my side, but he kept quiet. I knew he was just worried about my safety, but it bothered me a great deal. Finally, Dean shook his head disapprovingly and said, “Fine. But having a damsel in distress to take care of really makes our jobs harder.”
I chose to keep my mouth shut. I was furious that he called me a damsel in distress, but that just made me more determined to show them what I was made of.
We got in the car and drove for about a half an hour before we arrived in a small town called Cawker City. I wondered why it was called a city when it was clearly not big enough to be a city.
On the drive there, Dean had explained the situation to us. “This demon’s not playing around,” he had told us. “My sources tell me she’s killed two people so far. Rumour has it she lives in an abandoned gas station.”
We arrived at the former gas station in question. The pumps had been removed, but the building was left to decay. I psyched myself up and prepared to fight. I was small and chubby, but I was stronger than I looked. Demons, of course, were still stronger than me on account of their superhuman strength, but I could put up a good fight and often won in spite of my inherent disadvantage. I was a tough little soldier and I was ready to prove it to Sam and Dean.
We went inside and Sam was immediately tackled to the ground. This demon was - as Dean had said - not playing around. I began reciting the exorcism prayer that I knew off by heart. The demon recoiled, getting off of Sam and running at me. This time I didn’t freeze. I kicked the demon as hard as I could and she flew backwards onto her ass. As much as I didn’t want to hurt the poor person being possessed, it was often necessary. It was self-defence. I lunged at her and began punching her, trying to keep her down while also not trying to seriously injure the body the demon was in.
I kept saying the prayer as the demon screamed and tried fighting back, but I had her pinned down now. I could imagine Dean watching in amazement, thinking about how wrong he had been about me.
But then, out of nowhere, two more demons emerged from the shadows and pulled me off of her. Sam picked up the exorcism prayer where I had left off and the demons let go of me and went for him. All three demons attacked him, but Dean inserted himself into the mix and stabbed one of them in the chest. I saw the demon glow with a bright orange light. I had never seen anything like that before. Dean pulled the knife out and the demon - or the person the demon had been inhabiting - fell lifeless to the ground. I was shocked. Dean had just killed a person right in front of me.
We were supposed to protect people, save people. That’s what hunters did. But Dean had just killed someone.
But I didn’t have time to meditate on that because the other two demons were still attacking Sam and he looked like he was losing. Dean went to stab one of them, but I rushed over and knocked the knife out of his hand.
I began fighting the demons, reciting the prayer as I did so. They fought back, but Sam and I were able to stand our ground. Then, Sam got knocked to the ground. I finished the prayer and the demons were violently ripped from the bodies they inhabited. The formerly possessed people fell to the ground.
I leaned over Sam. He had been beaten up pretty badly. His nose was bleeding, his face was bruised and there was a gash on his forehead. He propped himself up on his elbow, clearly about to try to stand, but I stopped him. He looked like he might pass out if he stood up too quickly.
“Are you okay?” I asked.
“Yeah, I’ll be fine.” He tried to stand again, but I stopped him once more.
“Take it easy. Relax. Don’t hurt yourself.”
“What the hell was that?” Dean demanded.
I turned to Dean and got right in his face. “I should be asking you the same question. You FREAKING KILLED SOMEONE. AN INNOCENT PERSON.”
Dean shoved me to get me out of his face. I stumbled backwards a few steps, nearly tripping over Sam, who was still on the floor. “Look, I know you’re used to hunting with the exorcism prayer, but that’s not efficient. We have a way of doing things and you’re going to have to get used to it if you want to work with us.”
“YOU. KILLED. SOMEONE!” I yelled. I was livid.
“Calm down, Sylvester,” Sam said, standing up.
“Calm down? Calm down? Your brother just killed an innocent person and you expect me to just calm down? Okay, sure.”
“It was necessary,” Dean insisted. “Demons damage the bodies they possess, often killing them. Or sometimes they possess corpses. That person may have already been dead. And if they weren’t, the exorcism could have killed them.”
“What’s happening, where am I?” One of the formerly possessed people had awoken.
I decided to forget about Dean for the moment and I bent down to speak to the person. She was clearly very scared and I had done some significant damage with my punches. “Something very traumatic just happened to you. I need you to know that nothing that just happened was your fault. You were a victim of possession. Demonic possession. I know that sounds crazy, but it’s true.”
“Oh my God.” She began sobbing.
“I know this is a lot to take in. We’re going to get you to a hospital. You can’t tell them you were possessed, they’re going to think you’re insane. Say you were attacked by someone from behind and you didn’t see their face. Okay?”
“Okay,” she whimpered. I put my hand on her shoulder and told her it was going to be okay.
The other victim was still laying on the ground. Either they had been a possessed corpse or they had been killed either by the demon or the blows that Sam and I had delivered. If it had been us who’d killed them, it wouldn’t be the first time that happened. I hated Dean in that moment, but he was partially right. Demonic possessions often ended in loss of life and, as a hunter, sometimes killing a human was an undesirable byproduct of the job. But when I killed someone it was always accidental, an unfortunate result of trying to save lives. Dean had just stabbed that person in cold blood. It was different.
“We’re not taking her to the hospital. She’s going to call herself an ambulance,” Dean said.
I turned to him. “You can’t have an ambulance come here, they’ll see the bodies and think she had something to do with it. They’ll have all sorts of questions she can’t answer. The poor girl is traumatized, you’re just going to leave her here?”
“Yes, we’re just going to leave her here. What happens when the ambulance arrives isn’t our problem. We did our job. Now let’s get out of here.”
I turned to Sam expecting him to be equally appalled by Dean’s callousness. But Sam seemed to be unwilling to take sides. “Sam. Come on, get behind me on this one. It’d be cruel to just leave her here.”
Reluctantly, he said, “He’s right, Dean. We should take her to the hospital.”
Dean sighed. “Unbelievable,” he muttered to himself. “Fine. We’ll drop her off somewhere and then she can call the ambulance. If we take her to the hospital there could be witnesses. This nearly-dead woman getting out of an Impala with three suspicious-looking men in it looks real bad. We’re not getting blamed for her injuries.”
I agreed. He did have a point. Sam went to pick the woman up, but I stopped him. Sam was in bad shape. I picked her up and carried her to the car. We drove to somewhere discreet where it would be believable for her to have been attacked and I laid her down on the ground since she was too weak or too shaken to stand. I assured her she would be okay. Dean told the woman to call an ambulance from her cell phone. As she dialled the number, we got back in the car and drove off.
Sam sat with me in the back seat. I could tell he was in a lot of pain. I had brought with me a first aid kit that I had left in the car and I used it on him. I placed a bandage over the gash on his forehead. I held a wad of gauze under his nose to catch the blood. He seemed tired. I told him to rest his head in my lap. He complied. I continued holding the gauze with one hand and stroked his hair with the other as we drove back to the bunker.
Dean didn’t say a word to me the entire ride back. I was still furious, but my concern for Sam took my mind off of it.
When we got back, Castiel was still in the library, sitting perfectly still in the same spot he had been before we left. Dean sat at the table across from Castiel as Sam and I continued to the infirmary.
I got him a painkiller and waited for it to kick in so I could stitch up his forehead. I took a painkiller as well. My knuckles were bruised and sore from all the punching. I was shocked I hadn’t broken one of my hands again (I’d broken my hands many times over the years). I asked him about the knife Dean had used.
“It’s a demon-killing knife. It’s a very rare weapon. It permanently kills demons instead of sending them back to Hell.”
“Well, I don’t like,” I declared.
“Yeah, I don’t, either,” Sam sighed.
I decided to change the subject, I didn’t want to think about it anymore. It angered me too much. So I started asking Sam about other things they knew about that I didn’t.
After about a half an hour of Sam telling me things that frankly blew my mind, he announced that the painkiller was working. I stitched up his forehead as he winced (even with the painkiller, it hurt to get stitches without local anesthetic, which they for some reason didn’t have in their infirmary) and continued to regale me with tales of all the crazy things he and his brother had done and seen in their days as hunters.
“So, you and Dean are, like, actually legendary hunters. You’re kind of a big deal, huh?”
He nodded. “There’s even a book series about us. They have conventions where fans of the books dress up and hang out together. It’s bizarre.”
“What? Who wrote them?”
“A guy named Chuck Shurley. He was a prophet of the Lord.”
“What the fuck? Damn, you two have sure lived crazy lives.”
“You can say that again.” We were both silent for a moment before be added, “I’m sorry for my brother. He can be kind of rough around the edges. He means well. Try to go easy on him, he’s been through a lot.”
I nodded, but I was a little annoyed. I had been going as easy on him as I could stand to be. He really irritated me. He was so very irksome. But I knew that Sam loved him a lot and, from what I had heard so far, those two really had been through a lot of traumatic stuff together. Dean wasn’t THAT bad, I told myself.
“I get that he’s been through a lot, but you’re with me when I say that he can be kind of a dick sometimes, right?”