Who’s a Good Sissy?

I anxiously stared at my phone, waiting for his reply. I had been talking to a really hot guy on Grindr and he said he would let me know when I could come over to his. I had already freshened up, so there was nothing else I could do but wait for him to finally get back to me.

“Hey, sorry about the wait but you can head over now.” His message lit up my phone screen and I sighed in relief.

“If you made me wait any longer I would have thought I was getting ghosted!” I jokingly replied. He sent me his address, thankfully he wasn’t too far from me. Meeting new men always made me nervous and long drives only made things worse for me.

I quickly checked myself out in the mirror before going, admiring my thin legs and bubble butt in my high cut denim shorts. I coupled this with a mesh singlet which showed off my slender frame, if I wanted a six pack I could easily have one but that would require me having muscle which I did not. I tried working out for a while but I didn’t seem to get anywhere, which didn’t really bother me so I accepted the fact that I would always be a twink

I got in the car, unwrapping a piece of gum and throwing it into my mouth before pulling up his address on my phone. I was about to start driving when I noticed a notification pop up on my phone.

“I’ll have a few surprises for you when you get here, that’s why I took so long getting ready.” I read his message, slightly curious as to what he possibly could have planned. Despite wanting to know, I decided to give him a short reply so I could get to his place as soon as possible.

“Sounds interesting, guess I’ll find out soon!”

The drive felt like the longest 15 minutes of my life. All I could do was try and focus on the road instead of my nerves, or wondering what he was going to surprise me with. I messaged him to let him know I was here and he appeared shortly after to open the door for me.

“Hey, nice to meet you. I’m Liam.” He said, smiling at me.

“I’m Je-” I was halfway through introducing myself when I felt Liam’s hands pulling me towards him, his lips locked on mine. We kissed a little more before he stopped and grabbed my hand, leading me up to his bedroom. I couldn’t see anything special in his room, which made me even more curious about what he had planned.

“Two things; Firstly, I’m Jesse. Secondly, what are you surprising me with?” I asked, deciding that being upfront with him was probably the best way to go. With the way he jumped on me at the front door, I doubted that I’d be getting too many words in with this guy.

“Yeah about that, I’ve got a fantasy that I want to try out and you seemed like you’d be into it too. I mean I hope you are.” He said, scanning my face to see how I’d react.

“Well Liam, it would probably help if you told me about it.” I replied, holding my best poker face despite my nerves.

“I suppose you’re right.” He chuckled lightly before returning to a more serious look.

“I want you to be my sissy, you have the perfect body for it and you already dress kind of feminine too.” Liam said, looking me up and down before making eye contact. He wasn’t wrong, but it was also something I hadn’t really considered doing. I wouldn’t say I was a crossdresser, or honestly that feminine either.

“Hmm, I’m not sure about it. I don’t think it would really be my thing. I don’t mind BDSM but yeah.” I replied, watching to see how he reacted. He then asked me if I was into dom/sub stuff and I told him that I was. I hadn’t done it too much but I loved the idea of a man taking control and giving me orders.

“Well that works for me. Are you going to be my good little sub Jesse?” He grinned at me confidently, I don’t even think he was asking because it felt like he knew what my answer was going to be already.

“Yes Liam, I’ll be a good sub for you,” I answered him, swallowing in hopes that it would cut some of the sexual tension. He told me to close my eyes before leaving the room, coming back moments later with who knows what.

“I’m going to restrain you now, followed by a blindfold.” He stated before I felt the cold steel cuffs wrap around my wrists. We briefly talked about boundaries and safe words before, all I had to say was “cherry” and he’d stop what he was doing.

After cuffing and blindfolding me, he pushed me down onto the bed and told me not to move or talk. I was starting to get concerned, wondering if he was still here with me. Liam had gotten me pretty excited by taking control, but that was starting to fade as I lay still in his bed. My penis had become completely soft, which is when I felt his touch on me.

It felt like he had put something on me, like a cock ring. I had seen some online that fit your whole package and not just your dick so maybe it was something like that. That’s what I thought anyway, until I felt him put something over my dick. I heard a click, followed by him saying that the first surprise was done.

“Just two more to go, and no you can’t talk yet.” It was like Liam had read my mind, I guess that’s the power of an experience dom. I felt him get on the bed, lifting my legs up to slide some clothes up my legs. It was a thong followed by something else, but it was hard for me to make out what it was from just having it touch me briefly.

Liam took my handcuffs off and raised my arms, sliding something over me. I think it was a crop top but it felt a bit tighter and more revealing than that. He restrained me again afterwards, saying there was one more surprise.

“I’m taking the blindfold off now, are you ready?” He asked, making me wonder what exactly I had to be ready for.

“Yeah I guess so.” I replied, anxious to see what he had done.

He sat me up at the edge of the bed before taking off my blindfold so I could see myself in the mirror. I was shocked, both at what I saw and at myself. I felt so stupid for not seeing this coming. I was now wearing a mini skirt that hugged my waist and left nothing to the imagination. You could see most of my ass as well as the baby pink thong that I was wearing too. What I thought was a crop top was actually a matching bra, but I still couldn’t see what was around my cock.

“Can you show me what you put on me?” I asked in a hushed voice. Liam walked over and lifted the skirt up, pulling the thong to the side.

“What is this thing?” I asked, not really knowing what I was looking at.

“It’s a chastity cage, all good sissies wear them for their doms.” Liam replied, explaining what the purpose was.

I sat there processing what he had just said to me. I stared at myself, not really sure how to feel about everything. I guess the clothes didn’t look bad on me but why was I not allowed to get hard and play with myself? I was lost in thought when I heard Liam say something, snapping me back to reality.

“You look great as a sissy, but you would look even better sucking my cock.” he said as he took off his clothes. He kept his underwear on, his hard cock looking like it was going to rip a hole in them.

“I don’t know if I want to do this …” I hesitantly replied.

“You were mesmerised looking at yourself in the mirror earlier, give it a try and I’m sure you’ll come around.” He reassured me, walking closer until his bulge was right in front of my face.

“I know you want to suck my cock, show me that you’re a good sissy.” Liam said as he leaned forward slightly. I felt his hard cock brush against my lips and I started to get turned on again. I pulled down his underwear with my teeth and started to suck the head of his cock. I got it nice and wet before working my way down his shaft, struggling to take it all in. He had shown me some pics before but I had forgotten how big he looked in them.

“You’re great at sucking cock sissy.” He moaned out when I managed to deepthroat him. My cock was twitching so I took a quick break to breathe and see what was happening. My locked up cock was trying to get hard and I could see precum leaking out from the tip of the pink cage. Liam wiped the tip with his finger before holding it in front of me, making it pretty obvious that he wanted me to swallow it.

“Such an obedient sissy.” He said as I sucked on his finger. I had no idea why this was making me so horny but my cock was a good indication of how turned I was by this whole situation. Liam went and got some lube and began fingering me, if he was going to fuck me then I definitely needed to loosen up. He found my prostate and started rubbing against it with his fingers, making me moan uncontrollably. I was a quivering mess, not to mention how much precum my cock was leaking, and this was just from being fingered.

“If you want my cock you’ll have to beg for it sissy.” Liam whispered in my ear, his breath dancing against my skin. He pulled his fingers out and I immediately missed the feeling.

“Please fuck me Liam, I need your cock in me.” I pleaded, hoping that was enough.

“More.” He demanded.

“Please Liam, I’ll be a sissy slut for you anytime you want! My sissy ass needs your cock in it!“ I desperately moaned out, praying that he would slide his cock inside me. My prayers were answered shortly after as I felt the head of his cock push against my hole.

“Look in the mirror sissy.” He ordered. I turned my head to watch him slide his cock up my mini skirt and all the way inside me. I moaned in pleasure feeling his cock fill my ass up. He then began to steadily thrust his cock, grunting every now and then which let me know that he was enjoying himself.

“Who’s a good sissy?” He asked as he spanked my ass.

“I’m a good sissy.” I answered him, slightly caught off guard by the impact of his spank.

“I knew you would like it, you’re going to be my personal sissy from now on. You’ll come over whenever I need a hot sissy to use, understood?” Liam asked, starting to fuck me even harder than before.

“Yes Liam, I’ll be your sissy whenever you want. I want to be the best sissy you’ve ever had!” I moaned out. I didn’t even mean to say the last part, but saying it had turned me on even more. Admitting that I was a sissy for Liam and being willing to do it whenever he wanted to must have flipped a switch in him, as he started fucking me faster.

“Good girl, I’m close now.” He grunted out. He slowed down shortly after, thrusting hard and deep into me. I couldn’t help but moan as I felt each spurt of cum getting blown inside me, there was so much of it! He pulled his cock out of my now loose hole and I felt his cum start to leak out of my hole, running down my legs.

“Good sissies don’t waste their dom’s cum.” He stated. He used his cock to wipe up the cum that was leaking out of me before standing in front of me. His cock looked perfect covered in cum, I couldn’t help but get to work on it right away. I took his whole cock in my mouth, running my tongue up and down the shaft to lick up his cum before sucking on his head. He moaned out in pleasure before telling me that I had been a good sissy, which made me very happy.

After cleaning up, Liam gave me the clothes he dressed me up in to keep, along with the chastity cage. I was instructed to wear the chastity cage at all times and to dress up as a sissy whenever I was at home. I was about to put on my clothes but instead I decided to put on my new sissy skirt and bra to surprise him.

“I think I’ll drive home like this.” I teased, hoping to please Liam even more than I already had.

“Looks like I’ll be making you late for dinner then.” He said, grabbing me and throwing me back onto his bed. His cock was rock hard again and as a good sissy, it was my job to take care of it.

Author: Alison ♥