[FMK] Her Reluctant Slave: Chapter 5 (Patreon)

CHAPTER 5

I didn’t do any practicing with that dildo, or the bottle of lube that was included in the gift box. I didn’t want anything in my ass—but I knew there was no way out of it; I knew that I didn’t have many options: either fuck myself in the ass with the toy or risk being ridiculed by all of my classmates, and probably disowned by my parents as well… maybe even arrested for ‘raping’ my mature neighbor. Those weren’t options I was willing to explore.

So I spent that whole evening on Google. “Can you damage your rectum with a dildo?” was one of many questions I looked up. The internet seemed to think that a well-lubricated dildo was perfectly safe, as long as it wasn’t made of cheap plastic. “Unless it’s bigger than a wine bottle, it’s not going to permanently stretch you out,” said one article after I looked to see if the damage could be permanent.

And then I found the videos: girls demonstrating how to insert a dildo anally. I couldn’t bring myself to watch the men doing the same thing; I just assumed the anatomy of the ass was the same either way. The girls made it look easy, but to be fair, they were porn stars and it was their job to look like they enjoyed being penetrated.

I will admit that I became a bit curious when I came upon one amateur video of a girl using a dildo on a trans girl, making her moan. She pumped her until she came—and she never even had to touch her cock. That got me searching things like, “Does anal feel good?” But the answers that I got just put new fears into my head: what if I end up liking it? What will Kate think if I end up with an erection? What if I end up coming? I don’t want her thinking that it was something that I wanted.

And after hours of researching, I will admit that I was strangely fascinated—almost enough to take the toy for a practice run. I found myself in my room, holding it in my hand. It wasn’t huge; it was about as big as me, and I was fairly certain that I was an average guy.

The thought of having it inside of me was both terrifying and strangely exciting. I curled my fingers around it. I remembered fucking Kate in the ass, and she really seemed to enjoy it. From my research, I learned that it feels better for men because of the prostate gland. So if she enjoyed it, I should enjoy it even more… But that’s not what I wanted.

I already felt ashamed enough wearing panties under my jeans, sleeping in girls’ nighties, shaving my legs. I didn’t want to enjoy anal sex on top of it! It didn’t help that one poster online said, “After you come with a dildo in your ass, there’s no going back.” That’s the last thing that I wanted. I wanted to eventually have a healthy relationship with a nice girl; I didn’t need to have some anal requirement getting in the way. I could only imagine it being a huge turnoff to tell a girl to penetrate me from behind… unless I was with a girl like Kate.

Shivers ran down my spine. I checked the clock. Now, it was 11:40 PM. Her bedroom was still dark. Her living room light was on; Bee was still awake. I groaned. What if Bee looked into my window and saw me with the dildo? What if another neighbor looked in while taking their dog for a late-night stroll? Maybe I could close my curtains just a little bit—just so there was a small slit: enough that Kate could see and nobody else… or would that just make Kate angry? She seemed to get more pleasure when I was humiliated, like when she jerked me off in her car.

“Oh God,” I said, pacing around my room.

She never said to put on the nightie, but I had a feeling that she wanted it. I didn’t want to take any chances, so I put it on, over my shaved body. I went to my bedroom door and put my ear against it; my parents had been in bed for over an hours, but I wanted to make sure that the house was silent; I wished that my door had a lock on it.

I thought about sliding the dresser in front of the door, but I didn’t want to make any unnecessary noise. How many times had my parents come into my room in the middle of the night in my lifetime? Maybe a handful of times? It was a low risk, but knowing that didn’t help me to relax.

Now it was 11:50 PM—almost showtime. I took a deep breath. I knew it would be over and done with quickly enough. I knew that it wasn’t going to last forever. Maybe Kate would get bored if I played along enough. Maybe she was only doing this because I was resisting so much. She got off on my humiliation—but what if I wasn’t humiliated?

I saw her light turn on. My heart fell down deep into the pit of my stomach.

I knew that it was showtime. I knew that she was going to be expecting me to use her ‘gift’. I looked at the toy, which was on my bed, next to that bottle of lubricant. My stomach groaned. I bit down on my tongue and took a deep breath. “It won’t be so bad,” I told myself.

I saw her figure move in front of the window. I couldn’t quite make out her face, as she was a silhouette in front of her own lamplight, but I could tell she was looking at me: watching, waiting. I darted my gaze away from her. I had to just pretend like she wasn’t watching. I had to just get this over with. She never specified exactly what she wanted from me—she never said anything about going for more than a minute or going until orgasm. She just wanted me to use it, so my plan was to get it over with quickly.

I picked up the toy. It swayed and wobbled in my closed fist. The tip seemed suddenly thick, like a clenched fist. It seemed longer too—too long to consider inserting into myself… but I had no choice. I closed my eyes and took another deep breath. Then, I squirted a large amount of lube onto the tip of the shaft. The internet said the more, the better. I wasn’t going to take any chances. I must have gushed a quarter of that bottle onto that wobbly rubber shaft.

I was tempted to look at the window, to see if she was still watching, but I was afraid to see her. Now, with my gaze glued to my wall, I could pretend like I was alone, in the privacy of my own room, with no terrible eyes staring at me.

I kept my gaze locked on the wall as I climbed onto the bed. I stood that big dick up and I got on top of it. I probably didn’t look so graceful as I stood the wobbly shaft up, lining the tip up with my clenched asshole. I spent a long five minutes trying to figure out how to keep the toy upright while I figured out how to make it go inside of me. It seemed impossible, especially with all of that slippery lube. The shaft kept slipping left, slipping right, poking my balls, sliding up my back. “C’mon,” I groaned. My asshole was just too small and too tight. I tried to awkwardly push the tip of my finger in, just to see if it was even possible to push anything up into it, but my cheeks clenched so hard together than I couldn't even do that.

“This is dumb,” I groaned. I tried to remember the advice I got online. Many people said the trick for it to not hurt is to relax all the muscles in the body; it was easier said than done. I tried to close my eyes and I tried to force my muscles to relax. I felt so stupid, feeling the lube dribbling down my thighs, smeared all over my crotch.

Then, it just happened.

I’m not sure what I did differently; the angle must have just been perfect, because that toy suddenly pushed up into my body, making me gasp.

It was in me. I was frozen. It wasn’t just a little bit inside of me—it had slid in deep before I managed to catch myself. I looked down in a state of shock, feeling something where it didn’t belong. I just stared. I must have stared for a full five minutes. Then, I pulled it out of myself in a state of horror, panicking, worried I was doing some damage to my body. I stared at the limp fake cock on my bed. There was a line of smeared lube to show me just how much had been inside of me: almost five full inches.

I had no words. My lips were parted as I stared in awe of what I’d done. But I wasn’t done; I knew that Kate wasn’t satisfied, so I picked up the dildo, I lined it up with my anus, and I went for it again. This time, it only took thirty seconds to get the tip into me. Now, I had a bit more control, lowering myself slowly as I felt comfortable. Then, I started to slowly bounce, keeping my eyes closed, praying silently that this was enough to make her happy. I bit down on my tongue and assumed she wouldn’t be able to see that I was only bouncing on three inches of the seven-inch penis. From across the lane, there was no way she could make out those bottom few inches, unless she was watching with binoculars—and I suppose I wouldn’t have held it past her.

I kept sliding up and down, and then I felt something pushing against my taint. I looked down to see the base of the dildo, pushed into me; I had the whole thing in me. I gasped.

It didn’t hurt. It didn’t feel like anything was stretching uncomfortably or permanently. I was pleased to know that this wasn’t some form of painful torture—but those other fears were materializing. There was a tingling pleasure buzzing between my legs. Sliding on the cock actually felt… nice. It was exactly what I was worried about. I wanted to stop before it was something that I got used to, but I knew I hadn’t done enough for Kate.

So I kept bouncing.

That pleasure kept growing.

“No, no, no,” I whispered under my breath as soon as I felt my shaft getting hard. I tried to hold it down, but the arousal was strong. It just felt so, so good.

I bounced faster.

Then I gripped the tip of my cock. I tried to fight those urges, but I was just an eighteen-year-old male, surging with hormones. I had to jerk myself off. And it didn’t take long: thirty seconds of beating and then I felt the orgasm coming. I leaned back, not wanting to make a mess of my bed. I aimed my cock at my chest, but the power of my orgasm was beyond what I was expecting. Cum blasted me in the face, shooting over my shoulder, into my cheekbone, into my collarbone, and then finally spilling across my chest and abs, ruining the little nightie.

So that night, I slept in Bee’s nightgown instead of the lingerie nightie, which was slicked with cum. I was embarrassed with myself, but also tingling with a newfound excitement, having discovered a new pleasure that I didn’t know was possible—exactly what I feared. But those comments online were right: how was I going to go back to masturbating normally now?

I was embarrassed with myself, but I had no idea just how embarrassing things were about to get. When I woke up the next morning, I realized that I hadn’t properly tidied up, just pushing everything into my closet quickly, planning on cleaning in the morning. But while I was sleeping, my mom had come in to collect the laundry. The lace nightie was gone, along with the rest of my dirty clothes.

My heart fell down into my gut. A coldness covered my skin. How was I going to explain this one?