My Aunt Spanked Me When I Was An Adult

I was born in Singapore, and even though I left when I was young, I had to by matter of Law, serve my stint of Compulsory Conscription. When I was growing up, my Aunties were always around me, being the son of the eldest in the family, and the age difference was perhaps a factor in this experience... My youngest Aunt was only a mere 10 years my senior. We were both closest to my eldest Aunt, who is some fifteen years older than me.
 Growing up in Singapore, it is common to receive a sound caning as a kid from one's parents. In our cases, it was our Mothers who did the disciplining. As I was close to my youngest Aunt, we used to speak often about the canings we would receive, and how we coped with the aftermath of such. In any case, as I returned to Singapore during my Holidays from Boarding School overseas, I viewed both my Aunts differently. Both were a true epitome of the female form... The Elder Aunt was well-proportioned and extremely well-presented- Always in knee-length dresses, heels and sheer pantyhose. My younger Aunt was more modelesque, being tall by even European standards, and likewise, was dressed accordingly in a classy conservative fashion of above-the-knee dresses, suit and Pantyhose and heels.
I had a crush on both Aunts, who were somewhat different but both classy in their own individual ways. My younger aunt was more tomboyish, where my elder aunt is a true woman in every sense of the word. 
I actually had many chances to perhaps share my fascination of caning with my younger aunt- We often spoke about how we would not repeat the cycle with our own kids, etc  and we would discuss the actual technicalities of which canings hurt the most (hand, bum, arms,etc) . It was around this time I developed a strong curiosity for being caned by my aunts, as I was caned my a female member of staff in my school, and became fascinated with the experience.
I recall I used to test the water with my youngest Aunt- I used to ask her what a caning from her would be like.. and she would purse her lips, and go somewhat serious and reply, "Really Painful!" The problem is due to my inexperience, I was unable to take this to 'second base.' I just kept on killing my opportunities. I mean, there was even one time when I was being deliberately annoying, she asked me if I was behaving this was because I wanted her to cane me, and I just went all awkward and kept quiet, killing the momentum of the moment!
I even recall once when we went to the beach together, I was in the water and she picked up a floating piece of bamboo and waved it at me menacingly, I had to remain in the water as I had a throbbing in my swimming trunks and was embarrassed by this! I somehow instinctively know if I had gone up and presented my bum to her, she would have at that point, complied by giving me the caning I so wanted.
My last and final attempt with her was when I asked her about some *********** I had spotted where a woman was holding a whip and she was whipping a man, and she said that those were sadomasochists and were 'sick perverts.'  The conversation thereafter died, being replaced by subject matter which was of more positive light. Somehow thereafter, my youngest Aunt found love, and was married, so our time spent together was a thing of the past.
 Thereafter, I became closer to my eldest Aunt. She was great company, and I could speak to her about absolutely anything.I used to enjoy my summer holidays, as we spent a lot of time together and have long talks about anything and everything. She is a wise and classy woman till this very day.
In any case, it was time to serve my compulsory conscription and return to Singapore for two-and-a-half years. I was completely resentful of this, as I wanted to proceed to University and saw this as a complete waste of time.
In any case, I use to share this frustration with my Aunt, and she used to advise me to pursue some course of study just to keep my mind academically agile. Most guys of my large frame would have been assigned to a service (non-combat) vocation, but unfortunately, I ended up being assigned to an elite combat unit. The tough training plus the social isolation I felt in Singapore made me turn to my aunt more. (She was after all my only true friend there!)
I ended up signing up for some courses, but found myself lacking the motivation as I was often too tired. I began developing the idea of getting my aunt to motivate me by threatening to cane me if I did not muster the academic motivation, and at this stage, I would purchase the traditional feather dusters, and cut away the feathers, leaving nothing but a whippy crook-handled rattan. The canes being sold in shops in Singapore were too thin and 'junior' in nature for my adult bottom, I reasoned. 
I recall fantasizing that my Aunt had been lecturing me, cane in hand, and warning me that if I could not bring myself to achieve an 'A' grade, I would be caned soundly. I would put the cane on my study desk and try to believe this, but this failed as it was just a fantasy and I just ended up slacking off in my motivation to study.
I desperately needed her help, and the more I saw my aunt, the more I felt I needed to ask for her help, but I was too embarassed. This was around the time, I decided as a sort of 'social experiment,' I would leave a cane dangling in her cupboard. I was hoping this would propel her to ask me if I knew anything about this, etc etc, but she just ignored it. I then placed another cane dangling off the window sill in her room, and once again, she ignored it, to my frustration!
Early one morning on my rare days off, I waited for her at the front gate as she left for work and offered her a ride to the station, which she gratefully accepted. As I was dropping her off, i asked her if we could speak about something serious that night. She said she was working late that night, but that she would drop in the next day after work if I was going to be in at home. I gladly agreed. I recall having a lump in my throat all day, and even though I was expecting her all day, I jumped out of my skin when I heard her knock on the door.
When I let her in, I noticed just how amazingly 'official' she looked, with her dark jacket, knee-length dress and tan pantyhose. She sat down and I made us some drinks, before I sat next to her almost dumbfounded by the whole situation. She just went all quiet, waiting for what I had to say.
 I explained that I would not be asking her if I did not feel close to her, but that I was feeling very desperate, as I wanted to do well in my studies in Singapore, as I did not want there to be a 'gaping hole' in my academic history caused by my compulsory conscription, etc etc.
I finally asked if she would help me by caning me when I needed to be 'motivated.'
Her initial reaction was that of amusement- She laughed and told me top cane myself! She went on to assert that she felt maybe if I could not motivate myself, the Universities I apply to would understand the nature of full-time compulsory conscription.
I however stuck to my guns and pleaded with her to please at least consider this. She said she would, and we changed the subject and went out for dinner.
In any case. on my days off, I would often send my aunt to church, saving her the long walk to public transport. One Sunday, after I picked her up from the church and we went out for dinner, she raised the issue most unexpectedly. I had noticed just a couple of weeks prior to that, she would pass me and wave whatever was in her hand menacingly as if she was going to beat me with the object in her hand- be it a wire coat hanger or spatula, etc.
In any case, I nearly choked when she raised the issue with me over dinner. My stomach was in knots and I could not eat a single bite, as she asked me how I felt about being caned at the age of 19. I know she sensed my nervousness, but listened intently as I pointed out that criminals in Singapore are caned as well (albeit brutally) up to the age of 50. I also went on the defensive, apologizing for putting her in that position, and that we should let the matter rest, and that I would find some other way to motivate myself. She then began asking me how I saw myself being caned if she was to do it. I could barely breathe, let alone swallow!
 I said I imagined it on my posterior, as this was the only place tenable. If I was caned elsewhere, my platoon mates would see the marks, etc etc. She asked me how I thought this should be done, and I suggested I could lie on the bed or bend over a chair like in school. I also told her that I could be caned over her knee if she was not too uncomfortable with this. She looked intently as if lost deep in thought. 
After the unfinished meal, however, she asked me to wait and she went round the corner to do some grocery shopping. When she returned, I noticed among her groceries, were 2 slender rattan canes, which I pretended not to see.
In the car, we were both silent, and just as I was  about to turn off into her street, she asked to go back to my place. I felt a shiver down my spine! When we disembarked from my car, she carried with her the bag which had in it, the 2 canes. They were not as thick as my de-feathered feather dusters, but they were longer and thicker than what I was able to buy elsewhere!
 As usual, I asked her to sit down as I went to the kitchen to make us a coffee. When I returned, she had taken the two canes out of the bag and she was examining them intently. She slid her slender fingers over each cane as she seemed somewhat lost in thought. When she came to, she took a sip of her coffee and began to speak slowly but surely. She said she knew that I had given her the canes in the bedroom, but she felt that if she was to beat me, she should be the one who buys the cane. I accepted this with new found respect for her.I was seated alongside her and she crossed her legs and began to speak with a newly assumed serious tone, holding the cane and emphatically making a point with its slender qualities.
She asked me to go upstairs and bring down my work I needed to get done. I went up like a shot of lightning, and in minutes, was showing her how much I needed to get done, and how I was failing miserably at this.
She tole me to go up to my bedroom, and she followed me behind. I could feel her escalating feminine authority as I heard and smelt the fabric of her material brush against her bodily. I got to my bedroom, unsure of what to do- She then told me to put all my study material at my desk, Still holding the cane in her hand, she told me that she wanted me to keep a 'progress notebook', where I would give myself my own assessment as to my progress. My Aunt still asserted her position that no amount of canings could make me work if I didn't want to, but if I really needed help to 'go the extra mile,' she would help me by complying. I felt so in love with her at that moment!
 She then asked me how I felt I should be caned. I draped myself across my bed and placed a pillow under my hips to elevate my bottom. I then said that I should change into my military p.t. shorts, as this was thin, and whilst it offered me and her modesty, it would not protect me in any way. She seemed amused that I had thought this through! 
She then asked me to get dressed, which saw me jumping up and running to the bathroom to change into my shorts. I took my underwear off as well to be honest for her.
When I got into the same position, she began tapping my bum, and she brought it down with great force. I really jumped, and she laughed at my reaction, but nodded her head in a determined fashion and began warning me that I had better pull my socks up and get my work done and not waste my intelligence, etc and in doing so, I received about a dozen strokes,, and she allowed me to grab my bum and rub the pain after each stroke.
 After that, the procedure for my aunt was set in place, for her to cane me whenever I needed it. We did not discuss this at other times, but all I had to do was to show her my 'self-assessment progress report' and I would be caned by her either at my place, or at her house before she left for work in the mornings. She also once punished me when I was showing off my climbing skills on her gate and knocked over her porch lighting. 
 These canings helped me greatly in centering myself and my life's purpose and I missed her and them after my Military obligations were fulfilled and I returned to resume my residency and studies overseas. Than was some twenty years ago, though when I was in Singapore last, I am certain I saw the same cane hanging in her wardrobe ... Maybe I should summon up the courage to ask for a caning for old-time's sake?

cheekyboy33 cheekyboy33
36-40, M
May 15, 2012