"Alright, sweetheart, I need to leave for work now. I don't wanna be late today," said Trisha, putting on her clothes. "I am gonna see you in the evening then."

"Please don't leave me like this. Please come back to bed, we still have so much to do," I almost begged her.

I knew she wouldn’t stay. She really had to leave.

"You are gonna be home all day right? Please clean the house today. You never do anything. Don't just stay lying on the bed whole day, move that ass of yours, and clean the house, okay?" She marched out of the room.

I wouldn’t see her for another ten hours.

Trisha works very hard to earn some extra money for the both of us. We have been living together for three months now. I lost my job during the recession two months back, and have been job hunting since then. I haven't been lucky with that, so far. It kills me to see that all the expenses are taken care off by my girlfriend, and I can't contribute anything. I just lie around the house all day, waiting for her to come home in the evening when we can have amazing sex all night.

She is a wonderful woman. She's in her mid-twenties right now, extremely gorgeous. Being the kind of average person that I am, I often wonder how I got a hot girlfriend like her. She takes care of everything, without complaining. And the sex? It's the best sex I can imagine. She is so wild and kinky. We have been in a relationship for almost a year now.

A few months back, I dared to share a fantasy of mine with her. I was scared about how she would reply, but I could no longer keep it to myself, and so I decided to share it with her.

Five months back

"Baby, let's try something different tonight?" I asked her politely lying on top of her, both of us naked.

"Different? Sounds intriguing. What's on your mind?" she asked excitedly.

"Do you wanna try bondage?"

I thought she was going to freak out. Her eyes were getting wider.

"Don't worry; I am just suggesting light bondage, nothing much painful or extreme. I always wanted to try it." I paused, waiting for her reaction.

"Okay, let's try it."

I had never been happier than that. Finally being able to live my fantasy, I was extremely excited. I had this one favorite porn in my collection where the girl is tied on a bed bare naked. She is being spanked by a paddle repeatedly, until her ass turns immensely red, and she screams in pain. I wanted to re-enact that.

I shared the scene with my girlfriend, and observed her reactions carefully. She looked terrified. I don't think she has ever done or seen anything like that ever, but she kind of looked thrilled by the idea.

"Oh what the hell! Let's do this. But do you have a paddle?" she inquired.

"No, I don't have that. We can use the wooden ruler I have, if it's fine? And I can tie you up with the ropes."

"Yea, that's fine. Come on, let's do this tonight, you dirty bastard," and she began chuckling.

This being my first time into bondage, I was nervous as well. I tied Trisha properly onto the bed, and assumed my position near her ass, with the wooden ruler in my hand.

"Are you ready for this, slut?"

Calling her slut for the first time gave me a thrill and she seemed to be enjoying it as well.

"Oh yes, just start with it now."

SPANK!

I swished the ruler really hard. She shouted aloud in pain, but I didn't stop. Two more spanks, and I stopped.

"How is it? Do you want me to continue?" I asked, concerned whether that was getting too much for her.

"I will tell you to stop when it gets too much. Don't stop till I say so." She said, in between deep breaths and crying.

Three spanks and her ass was turning red.

But I had my orders now not to stop until she told me to.

Then with much more force, I began hitting her again.

It went on for quite some time. Each smack got harder, and her moans got louder. After around thirty-two spanks, I lost the count, but I was certain I had scored a half century at least. She was taking it much better than I had imagined. She moaned with every spank and her moans kept on getting louder every time I smacked her ass. Honestly, I never thought she would be able to endure so much pain, but it was after around fifty-five to sixty smacks that she pleaded me to stop. I stopped immediately. I love this girl, and didn't want to harm her, especially not during our first session.

"Are you alright? I shouldn't have hit you so hard, I am sorry,"

"Don't be silly. I am alright. It's just the pain... just too much." She began rubbing her hot, red ass. "I think this much should be enough for today, right?"

"Yes, yes, sure."

***

Since that night, we must have had such sessions, at least three times a week. She was really enjoying the pain. We have tried various things in our little sessions over the time. Things like she being gagged and tied the whole night, plug in her ass while in public. But I would say we were still at an amateur stage when it comes to BDSM.

One week back, Trisha suggested that we try this on me. She wanted to tie me up and thrash my ass. Maybe she even wanted to fuck my ass. I was scared by that thought. This was not part of my fantasy and I was scared to do it. Somehow, I got away with it. But I could feel she was a little disappointed and she has been disappointed since that discussion.

Trisha had almost ordered me to clean the house today. I thought I could do at least that much for her if I wanted to save my ass. I didn't want to disappoint her anymore, else I wondered she might stop our sessions altogether. So, I began to clean the house starting with the kitchen.

There is a little secret I have, though. I have been a closet cross dresser for the last five years. During my high school, I used to enjoy myself in my mother's and my sister's clothes. The feel of soft material, the feel of bra and panties, they turn me on a lot. When I left my home two years back, all the action had to stop. But I was so happy when Trisha moved in with me. I have been wearing her undergarments, her stockings, her high heels for the last three months now. Whenever I get time, I transform myself into my alter ego and have a little pleasure time of my own. I love women, and I love Trisha, but I don't know why this feel of transforming into a woman turns me on. I enjoy it thoroughly.

She had left for work, and I got the house to myself. This was the perfect time to change into my girlfriend's sexy clothes. I got into the bedroom, and began searching through her wardrobe. She had got a new set of pink bra and panties. That would be perfect for today while I clean the house, I thought. I removed my male clothes and got into the beautiful pink bra and panties. My little dick was very much erect now. The feel of the pink panties around my cock was doing wonders and was getting me crazy. I already have shoulder length hair, so I never require wigs to look feminine. I looked at myself in the mirror. I was looking quite sexy. To complete the look, all I required now was my girlfriend's high heels. I got on my knees to look for the perfectly matching heels from the lower compartment of the wardrobe. As I got up and closed the wardrobe, I saw Trisha standing at the door, her hands crossed, and a look of disgust on her face.

I was in big trouble.