Chapter 1

Hi my name is Will I am 25 years old 5ft 8inch blond hair and average build.

I live with my cousin Cleo who is 21 jet black hair at least a 38 d cup size, has a nice bronze tint to her skin, even though she was 5ft 5 she had long legs and a hour glass waistline.

Cleo had moved in after my girlfriend Joanne left me about a year ago. The reason why she left is because one day she left work early to surprise me but she was the one that was surprised, as when she walked in the front room there I was wanking off in her little black dress. She told me I can dress up whenever I wanted to now. I begged and pleaded her to not leave but she said that she could no longer look at me and she wanted a man not a sissy. With that she grabbed a suitcase and took all her clothes except the dress which she told me to keep as soon as I loved it so much.

After she left I tried to resist the urge to dress up but I couldn’t seem to stop myself I had to fulfil my urge. But after a while just dressing up didn’t seem to have the same effect as before. So I started to look into self bondage and went ahead and bought rope and some handcuffs with quick release switches so I could get out.

It was a nice cool spring night Cleo had gone clubbing with friends and wasn’t due back until early hours of the morning. So I thought it would be a good time to do some self bondage and have some fun. So I thought it would be best to do it in my bedroom just in case Cleo came back early. I went upstairs to my room and started to get out my ropes and handcuffs and put them on my bed.

I started by tying my feet together then connecting the rope to the bottom of the bed, then I picked up both sets of handcuffs that where next to me and connected one side to the headboard and the other side to my wrist then done the same with the other handcuff. Then I laid there for a while as my cock was throbbing inside the dress. At that point I thought I would release my right hand so I could climax, then untie myself and go to sleep. I pressed the release switch on the handcuff connected to the bed but it didn’t work, I thought no need to panic I will try the other one as I had used them before and the switch had worked. I tried that switch and still nothing, now I started to panic I kept pressing the buttons while squirming around trying to free myself nothing was working the only other way to undo the handcuffs was with the key that I couldn’t reach even if I could I doubt I would be able to use it with my hands cuffed. I had ran out of options except one which would be wait for my cousin and to hope and pray she would be understanding.

I felt myself climax at least twice while waiting for Cleo to return, and it felt amazing as I’ve always had to use my hand to guarantee ejaculation. Reaching climax this way felt euphoric. Then after all I could think about is what if Cleo freaks out and runs away or doesn’t come back till even later.

I couldn’t sleep and continued to try and escape but it was no use I wasn’t going anywhere. The minutes felt like hours and the hours felt like days. But finally after what felt like forever, I heard Cleo’s door keys rattle as she unlocked the door.

She shouted “are you awake? I’ve got something to tell you.”

I hesitated for a few seconds then answered “I am upstairs in my room.”

“well I hope you’re decent or at least got a cover over you because I am coming up.”

This was it there was no turning back. With every step Cleo took up the stairs my heart beat faster and faster I thought I was going to pass out...