Troy Pays Back Mommy! Pt. 01

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Troy was mad at mommy but punished me instead.
1.5k words
4.33
20.2k
9

Part 1 of the 2 part series

Updated 06/09/2023
Created 04/25/2019
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I had not heard from Troy in awhile as he had headed off to college but his brother Chris was another story. He liked the idea of having a sex slave and in his own apartment we would meet once every two weeks, sometimes more but never less. He also was really interested in trannies and while I was not passable he enjoyed having me dress if not fully, wearing pantyhose and heels. He would rip open the hose and savagely fuck my ass. Other times he would time me over a sawhorse and beat my ass raw and then fuck me. This felt so good. Chris could last a long time and being a submissive masochist I loved it when he beat my ass before fucking me. At times I could almost shoot my load just from the spanking!

One day he cancelled at the last minute. I found out the next day his father had a massive heart attack. A month went by before we hooked up again. I was in for a surprise. He had me get to his apartment early and he told me to dress for him with the clothing he brought. He had laid out a set of white stockings, red waist cincher, red 4 inch CFM heels, a wig, and, rather surprisingly, a matronly dress. He also left a note that someone would arrive to do my make up! I took the precaution to stick a finger of Vaseline in my ass just in case Chris wanted a rape scene.

When the girl came I was dressed except for the wig. She went to work on me and I saw her looking at a picture of Chris and Troy's mother! She told me Chris said to make me look as much like her as possible. Now June was a larger woman and her figure was close to mine except her huge (46G) tits. Bye the time she was done from a distance I was close to looking like her. She left as Chris got home. He told me I was to be a surprise for Troy! He further explained that his dad left them both a lot of money and that was how he paid for everything without thinking. Then he explained to me why he wanted me to look like his mom.

Seems after the funeral his mother was talking to her boyfriend and had not noticed that Troy was in the next room. She complained that her now dead ex had left most of his money to the kids and now she was stuck with a faggot for a son (Troy) who had a huge dick and her other son who she had not seen with a girl in a long time! Her boyfriend asked how she knew he had a huge dick and she said she caught him Jerking off one day watching gay porno. She told him it was a waste of a perfect dick. The boyfriend said she sounded jealous! She laughed and said not jealous but what a waste! At this point Troy burst in the room and went off on her, saying he was sorry he was a faggot. Troy had not spoken to her since.

Chris's idea was to let Troy punish his 'mother (me)' and maybe he would feel better. Since I enjoy a good ass beating and a rough fuck this sounded great to me. Troy was on his way over and had no idea what was going on. When got there he looked twice at me. I called him my little faggot and I could see his eyes rolling. I taunted him about having such a big beautiful cock but no one to use it on. I had also realized that he had been drinking and maybe I should have eased up when he suddenly started cursing me and calling me a whore and a slut. He said I was going to pay for calling him a faggot. I egged him on and he ran at me and dove on me. He rolled me over and put hand cuffs on me and a gag. I was going along with this as he had me stand and bend over the sawhorse.

He tied my ankles spread wide and took off one of the cuffs and attached it to the horse. He then used another pair and started to curse me out, telling me that his slut mother would soon see how he could use his cock. He then lifted my dress and started to spank my ass. Not satisfied that his hand was hitting me hard enough he started to use his belt. Frustrated by the dress he took a pair of scissors and cut it away! Since my mouth was gagged and I was tied I was in his complete control! He started yelling again telling me I was dressed like a slut. He then went to the window and removed the window blind rod and started to beat my ass! Wow did that hurt but hurt so good. As he kept up the spanking my cock got hard as a rock. This felt wonderful but I also had to keep the illusion that I was being punished. He kept it up for a good 30 minutes as I screamed and cried into the gag. During this entire experience my cock was rock hard. While it hurt I loved it! I enjoy having my ass beat! While doing this he was drinking a beer and smoking a joint. He hit my ass harder and harder. He kept saying "like how it feels mom? This is from your faggot son!" I was in more pain than I could imagine and with the gag in there was nothing I could do but at the same time the tears were tears of joy as I loved his punishment. Tied up I couldn't jerk my cock either that was ready to cum! The pain was wonderful!

He finally stopped and walked in front of me. His cock was the biggest and hardest I had ever seen! Now mommy he said. Let's see how good a cocksucker you can be with my huge cock! And you better get it wet cause then I am going to fuck your ass with just your spit for lube! He pulled off the gag and tried to fuck my mouth but I tried just licking it. He then cruelly grabbed my nipples and twisted them. As I screamed he shoved his cock head in my mouth. He then proceeded to face fuck me, forcing as much of his cock down my throat, making me choke. He did this for a good 10 minutes. My mouth and jaw was sore but his cock tasted amazing. I used all my skills and was just loving this blowjob I was giving. He never had pre-cum like this! He finally pulled out and slapped me in the face, telling me it was time for mommy to see how useless her faggot son is. My cock was still rigid and I couldn't wait to be fucked!

He walked behind me and pulled my ass cheeks apart. He squeezed and pinched my already sore ass. This made my cock even harder. As I cried he laughed. He then spit in my ass and I felt his cock head at my pucker. "Here it comes mother! In your ass because a faggot only fucks ass! With that he shoved hard, forcing his huge head into my ass but instead of pulling back he kept shoving hard. As I screamed in pain he laughed and drove his cock into my ass till I felt his balls. While it hurt it also turned me on. He then started to fuck me hard and fast. It hurt badly but my cock stayed rigid and even as I cried I loved the feel of his huge cock opening me up wide. Thank God I had put some Vaseline in my ass but nothing could have gotten me ready for this ass rape! Then it happened, no more pain, just pure pleasure from being fucked! He started to slam fuck me and I felt like I was ready to cum! All this time he was grabbing my bruised ass and the pain pleasure was exquisite! The entire time he fucked me he kept asking mommy if his cock was useless now. Finally he pushed hard and I could feel him squirt deep in my ass. As this happened my own cock started to squirt! I came hard as he filled my ass! Finally he pulled out his shrinking cock and forced into my mouth to clean. I eagerly licked clean his cock, more excited now than before, hoping he would untie me and allow me to really worship his cock and balls!

He looked down into my eyes and said "thanks mom! Still think my cock is worthless?" He then sat down on the couch and passed out! I stayed tied till Chris returned 2 hours later... end of part 1

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AnonymousAnonymousalmost 5 years ago
Confused

A little history at the beginning would have been helpful. You kind of started in the middle of the story. I didn't know who was who

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