Sissy Slave to my Ex Pt. 05

Story Info
I lose my anal virginity and give up more blackmail.
1.3k words
4.48
24.4k
15

Part 5 of the 8 part series

Updated 08/31/2023
Created 07/16/2023
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We finally got back to the dorm after one of the most humiliating experiences of my life. I carried the bags all the way up to the dorm. Mandy was following close behind me, she was on the phone the whole ride and on the way to the room.

I unlocked the door and walked in and was hit in the face with another surprise... Mandy had moved all my things around in my room and put her things in it's place. She had taken over 75% of the room and moved my things to one small corner of the room.

She took the beds in the room and made a king mattress when pushing them together. I also noticed there was a small air mattress on the floor in the corner with all my stuff. I demanded to know what was going on.

She walked into the room and said, "well I thought that in order to make sure I fully benefited from this arrangement I thought it was best to be keeping an eye on you as much as possible. Plus I had a roommate that I had to share half of my room with and here I don't have to worry about that."

I wanted to protest but I knew I had no leg to stand on. She could get whatever she wanted with me and she knew it. So of course I told her it wasn't a problem, plus having her in the room where she would be changing and living together may help out in the end.

She was so happy to hear that and said that we should make it official and sign this new lease agreement with the housing office so it would be legally binding. She handed me a pen and I wasn't sure if I should sign it right away without looking over it.

She then leaned over my shoulder and whispered in my ear, "you sign this right now and we can consummate the arrangement in that bed over there."

I started to shake and quiver hearing every word out of her gorgeous mouth. I knew I couldn't trust her so I was still cautious about signing till she started kissing my neck and running her hands down my chest and into my pants.

My cock tried burst but it was still confined in that chastity prison. I wanted this so bad that I would do anything to get it. I grabbed the pen and signed on the dotted line. The second the pen lifted from the paper she grabbed it off the table and put it in her bag.

She then told me that if we were going to do this it would be her way and she didn't want to give me too much of a reward. She handed me the same restraints from the previous encounter we had in this bedroom.

She told me that if I could take 10 spankings with her paddle then we would be able to have sex. I was nervous because I knew she would try her hardest to make me give up, but I wanted this more than ever. So I agreed, she then told me to bed over the bed and to ensure that I don't move during the whipping she was going to restrain me.

"If you decide to give up all you have to do is say mercy, then I will stop." I knew this was going to be difficult but I was determined. She then put on a blindfold so I didn't know when the hits were coming, that way I could not brace and make it easier for myself.

She proceeded to smack me with the paddle as hard as she could. I wanted to fall down to my knees but the restraints prevented me from doing so. "That was just the first hit, you sure you can go 9 more."

I was still recovering but I knew what the goal was, "I can make it" I said.

One hit after the other, each harder than the last. It was painful as can be, but when she finally hit me on the last stroke my body felt like collapsing. I made it through and I was going to get to have sex with her.

"I didn't think I was going to make it, but I can't wait to have sex with you Mandy".

She giggled, "I'm so glad you are as excited as I am, but I hope you have that same excitement in a minute." She reached and took off my blindfolded and I turned my head and began to panic.

I tried hard to get out of the restraints but they were locked tightly away. "I thought you said you were excited to have sex with me." She said that as she walked over to me with a strap on swinging between her legs.

She couldn't help but laugh, "I am going to keep my promise, I told you if you took all 10 hits, then we are going to have sex. You agreed to that, too bad you didn't realize this was the sex you were going to have."

She got up and I heard the squirt of a lube bottle and I started to struggle, she said "be careful, if you keep struggling it will make this go much worse." As she said that she pulled out the plug I had in my ass all day.

It was quickly replaced with 2 fingers that slide right in thanks to the previous plug and the lube. I clinched trying to handle what was going on, it didn't help to hear her giggle as she was fingering my ass hole. "You ready for the real thing? If you say the magic words, yes Mistress, I will take it easier on you."

I knew there was nothing I could do, I keep getting in situations that were worse and worse. So I swallowed my pride and said yes Mistress.

"Good boy". She said that as she slide in her strap on and invaded my ass hole. I wasn't sure how to feel. It felt so humiliating, but as she began to thrust in and out, it actually started to feel good.

Not just good, but she kept hitting a certain spot and it was feeling amazing. I tried to hide my moans when I put my head to the bed. She grabbed my hair and pulled it up and said, "not so fast, I wanna hear those moans."

I tried to hold them in but I couldn't any longer it felt so good as she began going in and out...faster and faster... harder and harder.

I felt my legs quivering from ecstasy and let out a moan. What the hell was happening to me, a week ago I was a normal college guy and now I am bent over a bed wearing panties all day and getting fucked by my ex girlfriend, who is now my Mistress.

"Moan my name bitch" she demanded as she was fucking me. "Thank me and beg for my cock you slut."

I let the pleasure take over my mind and said, "Thank you Mistress Mandy, please fuck me like the sissy I am".

She smacked my ass and said "good girl".

She then leaned forward and whispered in my ear, "turn your head and look to your right and smile for the camera. Let them know who owns you. If you act like you don't like this I will send every piece of evidence I have to your family."

Of course she was recording, I should have known. So I knew what I had to do, I looked right at the camera and smiled and moaned her name "Mistress Mandy owns me." She had one last thrust and then pulled out of my ass. Not without smacking both my cheeks one last time.

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3 Comments
Jean123456Jean1234569 months ago

I love your story, but I agree you are going pretty fast, it is okay to take more time to post a chapter that is a little longer but go more slowly.

AnonymousAnonymous9 months ago

Nobody is as dumb as this guy.

Bed_BugBed_Bug9 months ago

I really like your story but I would rather you take your time instead of feeling rushed (which is what this feel like) to keep up and posting short continuations. You have something really good here keep it up.

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