House Boy

Date of occurrence : 18-Feb-12


Miss had posted a requirement for a houseboy. Duties would be keeping the house in order, cleaning and grocery shopping.


As I read this, I felt so disappointed that I was not in the same city as she is. I have always been very service oriented and love to please a Mistress/Domme by doing housework for her. I find the satisfaction I bring to a Mistress by doing everyday tasks for her very rewarding. So seeing her requirement for such a position made me feel desperately frustrated because of the distance. In an email, I let Miss know how I felt about my frustration. I wanted her to know even though I could not currently serve her in this capacity, it is certainly something I would have loved to do for her.


It is hard for me to say why I enjoy this so much. I would say, it ultimately boils down to the notion that as a sub I need to be able to do something positive for my Dominant. I cannot imagine anyone not being pleased with the idea that their housework will be done while they sit and relax or get on with other important work. I have also found that I am good at it. So it seems like the perfect thing for me to do for my Dominant.


It is not really the housework that I enjoy so much. It is the fact that what I am doing will please my Dominant that I find enjoyable. I know after a hard days work, she will look down at me (as I kneel before her) with a smile on her face. I have been fortunate enough to have experienced this in the recent past with a Mistress. I will call her Mistress 'M' (very creative...I know :) It was a part time arrangement. Sadly, it only lasted about 6 months. But still, I look back to it with fond memories.

I would visit her once a week to do domestic chores, grocery, run errands, some light handy man work and carry out other laborious tasks around the house. Interestingly, she also liked that I dress up as a maid from time to time. I had a couple of maid uniforms that I would change into at her location. I have cross dressed before and quite enjoy it with the right person.

To expand on my experience and feelings about cross dressing I must take you on a short flashback tour.

I had always been curious about cross dressing but have to admit that I did not always enjoy it. In my mind, there was a conflict between fantasy and reality of cross dressing. Out in the open or even at home by myself, I never wear any feminine clothing. So when I indulged in cross dressing during play with a Mistress, I would feel very conflicting emotions. 


I liked the feminine touch of lingerie and the rest of the female clothing. But then I would look in the mirror I would feel ridiculous. It always made me feel silly and that would dampen my enjoyment. This changed when I met Mistress 'R'. I met her a couple of times for casual play. In just those few play sessions with her she changed my outlook on cross dressing.


Mistress 'R' loved transformation sessions. As always I was a bit apprehensive about how much I would enjoy it. All that changed as we started to play and I saw the genuine enjoyment on her face. She was just loving the whole routine of dressing me up. Her positive energy was rubbing off on me and I found myself enjoying the transformation like I have never before. From there on my future play sessions that involved cross dressing became quite enjoyable. I was able to get into the right head space and not worry about looking ridiculous.


Whilst I still don't dress up outside of the occasional play session, I have learnt to enjoy the kink with a Mistress that requires it.

Coming back to my situation with Mistress M.

Her location was over an hour drive from my place. I did not mind this (not initially anyway). In addition to the predefined list of tasks, there was always something ad hoc to do. As a reward for my service through the day, I was allowed to give her a foot massage and also worship her feet with my tongue. I was always very thankful for this. Sometimes she would also allow me to massage her legs. For this, she would be wearing a pair of shorts.

For the initial weeks this pretty much became routine. Then one day she told me that she was going to be away for two weeks. At the end of my service that day she told me she wanted a full body massage. She took off her clothing but kept her bra and underwear on. After the massage she stood up and told me she wanted some lotion rubbed in to her buttocks. It came as a total surprise and I was absolutely delighted.

With her permission I took her underwear off. It was the first time I saw her bare bottom and it was a very pleasant sight to say the least. I gently massaged some lotion into her butt cheeks. As you can imagine I took my time doing this. When I was done, there was more surprise for me. She told me to worship her behind.


I did not need a second invitation. I slowly kissed and licked my way around her ass, alternating from cheek to cheek I dragged my tongue over her ass from top to bottom and back, delighting in the shape of her ass. As I lay kisses to her ass, I also simultaneously massaged her butt cheeks. Her moans and positive feedback confirmed she was enjoying it. I wanted to lick and kiss her between her cheeks but I wasn't sure if I had the liberty to that.


Well...today was my lucky day. As she tired of my external worship of her ass she ordered me to get inside with my tongue. I immediately pulled her cheeks apart and started licking her asshole. Soon I had my lips sealed around it; french kissing it; trying to get my tongue in as deep as I could. My jaw hurt a little but I did not care.


She bent forward supporting herself against the wall with one hand and with the other hand she started stroking my hard cock as I continued my oral worship of her delicious backdoor. She commented on my excitement. All I did was mumble into her ass. This drew a little chuckle from her. As she was stroking me she made it clear I was not to cum. 

There was a full length mirror to the left of where we were position. She told me look into it as I continued my worship. I strained my eyes left without turning my face (I did not want to pull my tongue out of the warm burrow it was lodged in). The sight of my face buried between her cheeks was just amazing. This is pretty much what it looked like. Instead of tugging on nipple clamps, she was stroking my cock. She alternated between using her hand or foot for the stroking.

Once satisfied with my worship she told me to savor the reward as she would be away for two weeks. I returned a very happy boy that night and had an very enjoyable orgasm masturbating to the events of the day.

While my Mistress was away I thought I should do something nice for her. I knew her front and back yard needed mowing. Unfortunately I did not have access to the back yard. Anyway, I thought I would at least do the front yard. I hired a lawn mower and whipper snipper and drove to her house one of the weekends she was away. For first time lawn mowing I thought I did a decent job. I left a sweet note in her mailbox to greet her on arrival.

Needless to say, on her arrival, she was surprised at the new look of her lawn and was very impressed with my initiative. Soon, normal service resumed. Towards the end of the day, she wanted a full body massage. My massage style is very erotic and sensual in nature. It can be quite a turn on for any lady.

Brief overview of a typical Massage routine

I begin with the back, shoulders and neck. Then I move down to the feet and legs moving up to the buttocks. The inner thighs will get a lot of attention especially close to the genitals. It's now time to turn over. I'll do the front of the legs. Again the inner thighs will be the focus of my attention. I love to tease :)

At the end of the massage Mistress was on her back and breathing heavily. Her breasts were covered by a towel and she only a tiny g-string for panties. With her eyes closed she ordered my to smell her. Yes!!! This is what I had been so patiently waiting for all these weeks. All my hard work was going to be well rewarded today.

I bent over her and buried my nose into her panties. I could feel her hotness and smell her musky scent. I took deep breaths inhaling all her essence. She told me to take her panties off. As I pulled them all the way own her legs and off I was staring at her perfectly shaven pussy. Smooth and luscious, it was lightly coated in a aroused glaze. He could smell the lust and feel the heat emanating from her lips. She had one of those pussies that completely hid the treasures inside. "Satisfy Me" is all she said.

I knew I would enjoy exploring every fold of her pussy and digging out those treasures. I started gently with massaging her outer folds between my fingers. She groaned and her legs started to spread wider. Her juices were slowly starting to emerge. I caught a little sparkle of her wetness just at the entrance to her pussy. I had to be patient and really work my way up to it. This was my first time pleasuring her and I had to do it right.

I then gave her clit an external massage by gently squeezing the skin of hood between my thumb and for finger. I could feel the shaft of her clit as I did this. Her moaning and groaning was starting to pick up. I licked her outer lips as I continued the clit massage. Then I lightly pulled on her cunt lips my catching them between my lips. Her juices were starting flow in earnest.

I licked her slit and took a good helping of her wetness into my mouth. This caused her to arch her back in pleasure. I continued licking at her slit occasionally darting my tongue into her pussy. Her pussy was now flowing like a river. I felt the wetness on my chin. It was time to up the ante.

I pulled her hood back exposing her clit and took it in my mouth. Her groaning intensified. Using my left hand I held her clit exposed so I could pleasure it with my tongue. The middle finger of my right hand was now deep inside her pussy massaging the top of her inner walls. I used my tongue to give long, firm and flat stokes to her clit.

I kept this going and increased the intensity. I could sense her getting close to cumming. My tongue and jaw were aching. I took a short split second break and dived right back in. I had to keep going and not worry about my aching facial muscles. I had to give her an oral orgasm. My perseverance was soon rewarded as her orgasm overwhelmed her. When she climaxed, all her muscles clenched and she rammed her pussy against my face.

She just lay there taking deep breaths. As she came down from the heights of ecstasy, I licked up all her juices from around her pussy and also licked her fingers clean. I drove home with her scent on my face and had another deeply satisfying masturbation session when I got home.

Sooo....
As is evident from above, I particularly enjoy making my Mistress' life easy in any way I can. I also enjoying pampering her with full body worship. Bringing a smile to my Mistress' lips is one of my greatest joys. When I have pleased my Mistress, I also love to receive words of encouragement and an authoritative display of affection. Naturally,  I also enjoy other kinky activities and would partake in most kinks that took my Mistress' fancy.

You would think everything was perfect here and this arrangement should have lasted a lot longer than 6 months. Unfortunately, this was not the case. Whilst I was suitably rewarded for my service, I was not getting the affection and emotional connection that I so enjoy. We also did not connect too well on a vanilla level and there no interaction outside of service days. This eventually started to take its toll. The drive started to feel long and the work started to feel strenuous.

To her credit, she sensed I wasn't getting what I needed and we agreed to part ways in a civil manner. I hope to one day find a Mistress to serve in a similar manner, but one that I can also be emotionally involved with.


This recollection of domestic service intensified my frustration at not being able to serve Miss as her houseboy :(