Sean and I met in college. We couldn’t have been more different. I was devastated one semester when I only got a 3.9 GPA, where he seemed satisfied to simply pass. If a professor even hinted that I could do better on a paper or presentation, I put my entire will and force into the project and improved upon it. Sean didn’t even bother with the free extra credit assignments. His laissez-faire attitude about some things was vexing, but I still found it appealing… how the world seemed to bend around him without any effort on his part.
As anal retentive as I was, I let Sean control our recreational activities. He loved going to football games so we went even though I could barely follow the barbaric game. He liked to hang out in an out of the way pub so we went even though I could barely hold my liquor. When we graduated we shared an apartment in the city so we could save money. Truth be told, Sean didn’t need to save money as he naturally found a low-intensity high-paying job, but it helped me as my job barely paid anything and just offered advancement opportunities.
The tasks seemed natural. I mentioned that we should probably go food shopping, but the next morning I simply found a pile of cash and a shopping list on the counter. I went ahead and got everything on the list even though I didn’t like half of it. I mean if he was willing to pay for it, why would I complain about free food. I tried to talk to him about cleaning the apartment and how we could split the chores, but the next day I found our closet full of cleaning supplies and a list of what all should be cleaned. When I was a little shy of cash one time I asked him if he could spot me some money for laundry. He just chuckled and said he’d set me up the next day. The morning came and I found he had installed a new state of the art washer and dryer. Next to it he left a supply of laundry detergent, bleach, fabric softener… and all of his dirty laundry.
By the time summer rolled around I was cleaning the entire apartment and doing all the laundry. I had even stumbled into cooking all of the meals when one day he came home and seemed frustrated that there wasn’t anything ready. He didn’t ever tell me to do these things… he simply either pointed the way or more often just expressed frustration that it wasn’t already happening. I never looked to deeply into my desire to help out… I just wanted my friend to be happy.
His help with my personal appearance started that Autumn. He must have noticed my ratty old razor in the bathroom as one day I found a brand new one. At first I didn’t mention that it was obviously a woman’s razor as it still worked just fine, but one night I joked about it using a feminine razor. He didn’t seem to get the joke so I dropped it, but the next morning I found the razor gone and a bottle of depilatory cream in its place. It actually worked just as well as my daily shave, so I kept using it. The next week when Sean saw me without my shirt he just shook his head in disappointment and said he thought I’d use the cream everywhere. I really had no desire to be hairless, but there was something so compelling about his disappointment… so I started using it everywhere. The next time he saw me and my baby smooth hairless skin he didn’t even mention it. He just nodded his approval. And that approval felt so right.
When I clumsily tripped and fell down the stairs Sean came flying down to make sure I was okay. I tried to laugh it off but he brought his hand up to my face and I felt the sharp pain and winced. He told me he was taking me to the emergency room and guided me to his new car without me agreeing to be taken. Without me even agreeing that I needed to be taken. It turns out it was just a major bruise on my cheek. I mentioned off hand that I’d probably be embarrassed by the discoloration there. I guess I shouldn’t have been surprised that he took care of my embarrassment just as he took care of my health. The next morning I found a collection of expensive makeup. Concealer, foundation and even some kind of translucent powder. I had no idea how to use these things but when I later went to my laptop I found it open to a whole series of YouTube videos on how to apply makeup.
It took a couple weeks for the bruise to heal, but when I stopped wearing the makeup Sean gave me that mildly disappointed look again. I felt my stomach drop and tried to explain that it felt strange wearing just concealer and foundation. He nodded and left for work and I thought he had let it drop. The next morning I found a full collection of feminine makeup. Lipstick, lip gloss, eye shadow, eyeliners, mascara, blush… everything. When I came out to ask about it I found Sean gone and my laptop open to the same YouTube videos and a collection of beauty magazines.
I followed his lead, figuring he’d let it drop once he saw how ridiculous I looked in full makeup. My first attempt made me look like a horror show clown, but after watching the videos again, reading the articles in the magazines, and a few more attempts I got it to look somewhat natural. I felt so nervous standing in front of the door waiting for Sean to come home, but when he breezed in his smile and off hand comment about me looking good sent me over the moon.
Over the next several months a pattern started. I’d wake up and find some YouTube videos loaded up on my laptop and some magazines with relevant articles. Sean would already be gone, so I perused what he left for me and then tried it out. Exercises came first including yoga and Pilates. Cooking lessons followed that were designed to cook a dual meal… one that was tasty and fattening while the other was dietary and designed to lose weight quickly. The next week with the normal videos and magazines I found a collection of vitamins. Next were videos on hair styling and naturally a bathroom full of styling equipment. He never mentioned the videos or what he was trying to accomplish, but somehow he knew if I’d taken them to heart. That disappointed look could crush me for days at a time, while his quick smile and nod could send me to cloud nine for just as long.
The Rubicon seemed to be the videos and supplies for nail care. Up until that point I could use his lessons at home, and still make myself presentable for work. I got through his disappointed look and explained the dilemma. When he grew thoughtful and nodded, I figured the issue was solved. I hoped he’d continue but just with things that would allow me to flip between home and away. When I woke up I went through my normal morning routine, of makeup, hair, and exercise. When I went to the laptop I found my email client opened instead of YouTube. The message opened was from my boss. My former boss. He had replied to a message from me that I hadn’t written…. Accepting my resignation. When I closed the email program in shock I saw my bank account opened up and a transfer from Sean into my account with the tag of “Weekly Allowance’. It was more than I made at my job. I was so conflicted. Here was my life being dictated in a very personal and very powerful way and I worried about the loss of control. At the same time I felt… I don’t know… happy. Happy that Sean was making a commitment to take care of me. To make those choices for me and let me live a life of leisure. When he came home I was at the door waiting for him. I had his martini in hand and a conversation topic in mind, but his reaction was straightforward and powerful. He simply walked up cupped my pretty face and kissed me. I could barely speak and any complaint or concern I had was shushed away confidently by Sean, promising me that he’d take care of me. That he’d make all the choices from now on. That he’d never push me further than I was ready to be pushed.
I can’t lie, he was right. He was constantly pushing me, but never into something I couldn’t do. Beyond the occasional kiss to my cheek or the playful swat to my bottom, he never impressed anything directly sexual onto me. But everything had a shade of sexuality. My clothes were replaced with a new collection. Not all of it was skirts and dresses, but it was all distinctly feminine. Video lessons on walking in heels preceded all of my shoes being replaced with pumps and stilettos.
I never balked or complained. I fell into my new role with relish, nervously awaiting each lesson and new task. That’s not to say he didn’t notice my reactions and change course when he felt I was nearing a breaking point. For example, when he had a whole series of videos going over a sex change operation I became nervous and shaky around him. I never complained but he saw it. The next week those videos were gone, and a series of videos explaining breast implants were in their place.
During my recovery, Sean doted on me completely. He shushed away my attempts to get out of bed and cook, instead bringing me my meals to me and even feeding me. When he saw me worrying over the laundry and cleaning he brought in a maid to perform my tasks. When I was fully recovered the videos and training…. Because that’s how I now looked upon them… resumed. Any pretense of this not being sexual was gone as the training went directly in that direction. Pole dancing, lap dancing, and stripping were first up. After having the pole installed in Sean’s bedroom and practicing along with my morning exercise became normal, the training moved into even more intimate detail. How to touch and present yourself to your man had a VR game where I had to walk through those motions until they were normal. Fellatio videos were accompanied by a collection of realistic dildos. Anal sex videos were accompanied by a collection of butt plugs.
My nerves about actually participating in these activies, even with Sean, haven’t been tested yet. This month’s videos have focused on a different area. S&M, bondage, and roleplaying are my focus now. In this area Sean himself is my physical accompaniment. He’s already placed a collar around my neck that only comes off for cleaning. He often attaches a leash during our play sessions as he calls them. Those are sessions where he is learning along beside me. I learn relaxation techniques and how to hold certain positions for long periods of time… he’s learning how to tie knots and safely apply handcuffs and other toys.
The last few nights he’s had me tied up in several different positions on his bed. I even spent last night tied up and bound, my leash tied around his waist forcing my face next to his naked cock. By the twinkle in his eye this morning as he held my neck, chin and leash… as he kissed me softly over and over, as his other hand reached around me holding my arm and arching my back, I feel that tonight may well be that special night.
When he left and I saw my videos for the day… a complete review on fellatio and anal sex… I grew excited. I wouldn’t allow any doubt or hesitation to show tonight as I was ready to submit to Sean, my man, in this final way.