Curiosity Got The Better Of Me

by Prima

 

I have always wondered what it would be like to try on women's clothes and apply makeup to my manly face, don't get me wrong I am 100% male and love women particularly in sexy revealing clothing.

It was a cold winter evening in January, Donna, my girlfriend was away on a works conference and I was home alone. Donna works as an international manager for a well known company specialising in sex toys, because of her responsibility she is required to spend a lot of time abroad. Donna was very fond of her job and regularly bought some of her products home to test, which I thoroughly enjoyed.

I worked for a local video shop as a sales assistant and only earned a small amount of money compared to Donna's 6 figure salary. Needless to say I was a lucky man, I had a beautiful girlfriend who was very experimental in the bedroom and earned an absolute fortune.

Any way back to the time in question, I was bored of watching TV and was just kicking around the house on what to do. Then it hit me, why not try on some of Donna's clothes, she was going to be away until tomorrow and I had plenty of time to have some fun. I went to Donna's closet and looked over her clothes to find the sexiest outfit I could find, I then went to her underwear draw and found a very sexy pair of matching bra and panties. I undressed and started to feel nervous but excited at the same time, I removed my boxer shorts and saw that I had become aroused. I pick up the panties, a pink silk pair and put them on. The silk felt so good against my behind and my now aroused cock. I placed the matching bra on but it did not look right, I remember seeing a fake pair of breasts in some of the stuff Donna had bought home from work so I got them and placed them in the bra.

I looked at myself in the mirror, I thought I looked ridiculous but was detemined to carry through with my urges. I went back to the underwear draw and found a pair of black suspenders and a pink suspender belt, I put these on and I just loved the way the suspenders felt on my leg. I walked round for a while just feeling the air moving over the suspenders. I then took the red leather skirt that I had found earlier and put it on, it was 18" in length and very tarty. I placed a black blouse on to complete the look. I looked in the mirror and was surprised at how different I looked but still not feminine enough, the body was fine but the face was just me. I went in to the bathroom and grabbed Donna's makeup bag and applied a large quantity of foundation, pink lipstick and eyeliner to my face, whilst not brilliant I was starting to look like a girl. I found a blond wig in Donna's stuff and placed in over my head, my transformation was complete.

It was now about 9 o'clock in the evening and I fancied a bit of a drink so I went to the kitchen and poured myself a small glass of white wine and sat down on the sofa to watch some TV. Our house is out in the country and has large grounds there was no way anybody was going to see me. I felt so sexy until I heard the familiar sound of the key in the door and Donna shouting "I'm home honey", I panicked, how the hell was I going to explain this. Donna walked straight in the kitchen and carried on talking "The conference was a bit boring but there were several new products that we could try out. I have bought them home with me. Would you like a glass of wine?" I froze, what could I do? I replied "Yes please" and tried to make for the stairs but Donna was already walking back to the living room.

"WHAT THE HELL DO YOU THINK YOUR DOING!" she shouted at me, I just stood there. "WELL!" she continued, "I thought it would be a bit of fun, I'm so sorry". "YOU DAMN WELL BETTER BE SORRY. HOW LONG AS THIS BENN GOING ON? ARE YOU GAY? DO YOU WANT TO BE A GIRL?" she volleyed question after question to which answered "no I'm not gay I have only done it the once and I don't want to be a girl". "GET UPSTAIRS NOW!", I walked up the stairs and into the bedroom Donna followed. Donna seemed to suddenly calm down "You do look kinder sexy in all that gear and the wig really does hide you masculinity", "I'll get changed now" I said. "You will get changed when I tell you to get changed, now lie on the bed on your stomach". My mind was racing I did not know what to do, "Quickly does it" she said. I climbed onto the bed and led face down. Donna opened up the bag she was carrying and produced 2 pairs of handcuffs, she quickly cuffed each hand to either side of the bed she then produced 2 pair of leg restraints with a large metal pole between each end. She again quickly cuffed my ankles to the other sides of the bed. I was now positioned in a kneeling stance with my head resting against the mattress and arse facing the air.

Donna then left the room and returned with a digital camera, "Smile" she said. I told her "Please don't take any photographs". "I SAID SMILE", she became a lot sterner and all of a sudden I felt a painful crack to my rear. Donna had a 6" wooden paddle in her hand. I again refused but Donna just kept hitting me with the paddle, twice "No I won't smile", 3 more times "Please let me go", 4 more times "Please, Please stop". Donna just continued until I was in so much pain I gave in and smiled. "See that's better". Donna took picture after picture, removing my wig so that there was no doubt who I was and what I had been doing.

Donna left the room for what seemed like hours, when she came back she said "Right I have downloaded the photos and sent them to my work email address, you will do exactly what I say or the photo's will be posted to everyone you know and into all the magazines that will take them. I will not take any shit from you, if you talk out of turn or start asking me to stop, I will punish you. Believe me I have many different ways to punish you. Do you understand?". "Yes, but…." CRACK she hit my already red arse 10 times, "DO YOU UNDERSTAND!". I was left with no other option "yes, I understand", "MISTRESS DONNA" she stated. "Yes I understand mistress Donna".

"Good, now I have another little present for you" she reached into her back and pulled a hollow penis shaped metal contraption, "this is to make sure that you will stay mine". She grabbed hold of my balls and pulled them hard, the pain shot up my body and my semi aroused penis shrunk into submission. She place the contraption on an I heard a click, I knew the device was a chastity belt as she had shown me them before. "I will release you now but first I need to tell you that I do not have the key for that device on me today, it is in the office and I will not be going there until next week, and even then I may not bring it back. You have to be very good if you require any sort of pleasure from me. If you so much as try and leave I will send the photo's to everyone you know".

Donna released me and told me to get out of her clothes, which I quickly did. She told me to go to the spare bedroom and she followed me and once again handcuffed me to the bed. She turned the light out and just as she closed the door she said "Good night LOLA! We are going to have such good fun" before blowing me a kiss and closing the door

  

  

  

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