Blackmail Your Sissy

By John Nail

Published on Mar 7, 2017

Transgender

I will take comments from anybody at johnnail302@yahoo.com

This is what I love doing especially when they are afraid of being exposed if you know what I mean. The first time this opportunity arose was when I was in high school and I was using the high school gym to bulk up a little bit anyway I got done and went to hit the showers. I washed off the sweat and was drying myself off when I went to the lockers now this is the boy's locker room. I went by one of the lockers and something pink caught my eye. I looked closer and couldn't believe it they were a pair of lady's pink panties. I got dressed and decided to stay in the shadows and see who claims them.

30 minutes later a guy from the school swim team came and went to take a shower. I thought it may and may not just have to see what he does. He got out of the shower and went towards the locker and sure enough, it was the locker with the pink panties. I waited and just as he put them on and I snapped the picture.

I said," This is too good to be true the guy who called me faggot and he is the one who is wearing panties. The best part is I have the picture and this film can be developed pretty quick."

He said," What will it take for you to not say anything?"

I said," Hmm, Ok I don't care what story you tell at the store but I want you to buy a red lingerie and also put on red lipstick and makeup. But once you tell me you got this stuff well we are going to meet in a hotel room for a weekend and I am going to fuck you over and over. Of course, you will be wearing the lipstick makeup and lingerie."

He asked," Will this be one time only?"

I said," It maybe or if you are a good enough lay this might be a regular thing. Now if you try to wriggle out of any of them I will put these pictures in some embarrassing places for you."

Well, the weekend came and sure enough, he did what I ordered him to do and we checked into a hotel and we went into the room.

I looked at him/her and I couldn't believe what I was seeing she was hot and I was going to have fun.

I took off her panties and put her on the bed doggie style and climbed behind her and I put the lube on my cock and then plunged my lubed finger into her hole and she moaned and I worked the lube thoroughly into her hole.

I took off my shirt and pants and underwear and climbed behind her and looked at her bubble cheeks.

She cried and said," Please, I never had anyone inside me before."

I said," Sweetheart, you are so feminine I have to fuck you."

I started to push my cock inside and she let out a muffled scream but I kept pushing my cock until I felt my balls on her cheeks I loved the feeling of her tight velvety hole around my cock. I let hole adjust to my cock and then I started to thrust inside and out and she started to moan.

I fucked her for about 45 minutes and I shoved my cock deep inside and it bucked about 3 times filling her asspussy with my cum. I fucked her 2 or three more times that night and we collapsed and I spooned her into the morning hours.

We had those hookups on a regular basis until we both graduated and as far I know after high school she lived her life as a tgirl you can say.

Now 15 years later I am going to a club and looking for my candidate to become my next "girlfriend".

Next: Chapter 2


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