The Boots

"Trust?"

"Think about it Jim, I lead you here to the grotto. I gave you the boots you enjoy so much. So that means you trust me to do what is right for you." I watch for some type of reaction but his face and body lay like dead meat on the bed.

"Yes trust."

"Why do you love wearing the boots?" I ask softly. "Do they turn you on? Make you feel special, happy, and beautiful?"

Jim waited so long answering that I was beginning to wonder if he went to sleep on me. But after a few minutes he said softly, "Loved."

"You wear them because you know I love you in them?" I asked surprised.

"Yes"

"Yes I love you in the boots. They make you special, happy, and beautiful. You want to be happy right? You want me happy with you?" I pause a moment, "You need me happy with you."

"Happy"

"Yes Jim, you want to be happy. When I am happy you are happy. When I am unhappy or upset with you, how do you feel?"

"Sad," he said as if it were the worst possible thing.

"So you want to be happy, want me to be happy with you." Ok I know I was getting carried away but I could not help myself.

"yes happy"

"Ok Jim. When you wear your boots, you know I am happy with you. So what are you going to do when not at work to keep me happy?"

A hint of a smile crossed his face, "Wear my boots."

"Your boots make you special, loved, and beautiful. You wearing your boots makes me happy."

"Beautiful... Happy"

"Now just lay here in your grotto, thinking about becoming special and making me happy. You will find yourself drifting into sleep and your dreams will be filled with thoughts of becoming special, beautiful, and your boots." I said softly.

Removing his boots, I smile and set them off to the side. As I drift into sleep I think of fun little things I can do to see how far I can take this.

One of the nice things about Jim and I both being off at the same time is that we can take joint showers. Saturday morning came and after coffee we went to take a shower. He went first while I grabbed underwear. Smiling I added a little present folded in with his briefs. The last time I had visited Victoria Secret I bought myself some panties. Somehow I ended up with a pair that was one size too large. The pink satin French cut panties were just right. I folded them in with his briefs so he would find them. Frankly I did not know if Jim would wear them or not. But it could not hurt to see.

Showering together is always a treat; somehow by yourself you can never get your back as good as someone else in the shower with you can. He finished up and after scrubbing my back got out while I washed my hair. By the time I had finished he was already out. Looking on the counter I noticed both pairs I had left out for him were missing. A peek in the hamper showed two pairs of briefs laying in it.

While Jim started cleaning the house I started laundry. It took most of the morning to get the house clean. Throughout I could see something seemed to be bothering him but when I would ask he would shake his head no and say nothing. As we ate lunch I watched as he kept pointing his feet downwards and frowning when they returned on their own back to normal.

When we had finished I said after pointedly looking at his feet, "You know dear, if you wanted to put your boots on now..." I passed and looked at his face, "I would not mind at all."

Jim blushed and after a moment went to get them. He called back from the bedroom, "Darling? Where are the knee highs?"

I got up and went to the bedroom. "Oh dear... I put them in to be washed." Now I know and you know that knee highs come in packs of more than one. But Jim did not.

"Oh" He said in response looking like a child who lost his favorite toy as he sat them down on the bed.

"I know," I said, "You can wear a pair of pantyhose with them." I said a smile on my face. His look was comical.

"No... that's ok...." He said stuttering.

I moved over next to him and said softly, my hand on his chest, "I laid the panties out for you. I know you have them on dear... I bet they make you look beautiful." I leaned in a bit and kissed him softly on the lips as he turned red. "Let me see baby."

Blushing and fumbling Jim removed his pants; he was wearing the pink panties. He had managed to keep everything tucked in so at least he was not dangling. But, with them being French cut he really needed a shave.

"Hmm, almost beautiful." I said and removed my jeans. "Look at the difference" I said to him. I keep myself shaved because I love the feel of silk against my bald beaver. My hand reached out to stroke the satin and then pull at the fur sticking out on ether side. "trust me..." I said softly.

"I do..." Jim said softly his eyes closed.

I took his hand in mine and lead him down the hall. I stopped at the linen closet and grabbed a beach towel and lead him into the living room. Spreading the towel down I smiled, kissed him, and said, "strip down and lay down love."

As Jim did as I asked I went to the bathroom and got his electric razor with trimming attachment. By the time I got back he was laying nude on the towel. "Roll over" I said as I walked in. He looked up at me confused. "Trust me please."

Nodding Jim rolled over onto his stomach. He laid there, his eyes closed not moving. For a moment I wondered how far I was going to go and was I making a mistake. But the memory of Christmas came back to me and hardened my resolve.

Using the trimming attachment, I first trimmed the hair on his legs and then changed to the razor and shaved it all off. Once the back was done I had him roll over and shaved him. It took a while but once I was done Jim's underarms, legs, and pubic area were nice and smooth. Throughout the whole process he did not fight one little bit. "There, now your special." I said softly and kissed him. "Now to make you beautiful," I added.

I went into the bedroom and got the boots, pantyhose, and a pair of shorts for him to wear. Coming back, I noticed he was still laying there not moving. "Oh baby, time to get dressed," I said as I handed him the hose. I had to teach him how to roll and put them on. But once Jim was dressed and the boots were on he looked beautiful from the hips down.

I got him seated on his chair and legs up on the ottoman and stood looking at him. Though he was still blushing a bit I could see he was happy. "Damn, your legs are more beautiful than mine," I said after a moment.

"Thank you," he said looking at them as he turned his legs left and right admiring them. He seemed happier than he had been in a while. We spent the rest of the day and evening teaching him how to walk in the boots. Granted if I was not there he would have fallen or just crawled but once I mentioned that it might rip the pantyhose by crawling he became very determined to learn to walk.

When we went to bed that night I made him remove the boots and hose before going to bed. I could tell he didn't get a good night sleep by his tossing and turning. Sunday morning when I woke he was already dressed in shorts, pantyhose, and boots waiting for my help into the living room. Throughout the day I made sure I told him that his legs looked beautiful.

Sunday was spent just as Saturday was with the exception that in the late afternoon I said, "Let's go out to eat." Jim who normally jumped at the chance pouted in response. I smiled before adding, "You could always wear hose under your jeans." He seemed to brighten up to that idea.

All through dinner I slid my foot and leg up and down his leg. Leaning forwards I whispered, "Feels special and sexy doesn't it."

In a soft voice matching mine he looked at his plate and whispered, "Yes" and blushed.

After dinner I dragged him to the mall saying I had some quick shopping to do. Going into Victoria Secret I lead him back over to the panty section and started to pick out about a dozen pairs, all of which were shiny. As I picked out a pair I would ask him, "Like these?" and I would receive a nod in response. There was a hunger in his eyes that sent a thrill of excitement through me.

Leaving the store, I leaned over and whispered, "They are all for you dear, to make you beautiful." As I drove back home Jim sat in the passenger seat lifting up each pair and admiring them. Every now and then he would stroke his face with a pair and I could imagine him moaning with pleasure.

When we got home the very first thing he did was remove every pair of his briefs and toss them in the trash and replace them with the panties we had just bought. I watched from the doorway as he stroked them and said, "Beautiful," before closing the dresser. Once everything was put away he hurriedly stripped out of his pants and put his boots on. We spent the rest of the evening relaxing and again at night I made him remove the hose and boots.

The week passed uneventfully with him working evenings and me on days we did not have much time to play. The two interesting things to note were that every day he wore panties and hose to work under his uniform. The other interesting thing was that once he got home he would put his boots on right away. The transformation of his face was a marvel. He would walk in looking grumpy and harried and once the boots were on his feet his looks would change into serene and peaceful.

Friday night when he got home I was waiting for him. It had been a week since the last time he had gone under hypnosis and I wanted to take him down again. Once he was changed into his boots I smiled at him and said, "Jim, would it be ok if we tried hypnosis once more... Just so you can relax more?"

He hesitated for almost a full minute while looking at me. I thought for sure he was going to say no and say the gig was up. But instead he nodded. I helped him walk back to the bedroom and removed his shirt. Leaving him in the panties, hose and boots I laid him down on the bed and lay down beside him.

Taking him to the grotto was much easier the second time around and he drifted off without a hitch. It seemed as if he hurried there and was sitting waiting for me while I was still talking him through the swimming part. Once I was sure he was deep asleep I did my tests of pinching and caressing his body to test. But like before he showed no reaction.

"Nice and relaxed, calm and at peace," I said after a moment, "Each time you come back it becomes easier for you to reach this relaxed state. So calm so relaxed..."

"You love the feel of the boots, love the look of them, feel better wearing them don't you."

"Yes," came his soft reply.

"You could almost say your obsessed with wearing them. They make you feel beautiful, loved, and know I love to see you in them." I said softly.

"Obsessed?"

"Yes obsessed. When you are not in them, you miss them don't you?" I said leading him through the steps.

"Yes"

"And when you are wearing them you feel at peace and happy right?"

"Yes"

"So that means you are obsessed with wearing them."

Jim paused and then the hint of a smile crossed his face, "yes, obsessed"

I let his mind lock on to that for a bit then took the next step, "And the panties and hose? You love them too; they make you feel beautiful."

"Yes" I could hear the pleasure in his voice.

"Each person is made up of two sides, two parts. The male and female sides. This is nothing new you already know this right?" I said softly taking him in a new direction.

"Two parts...."

"Yes two parts... male and female... One of the parts is dominate and the other passive. This is nothing new. You know this also. One side is dominating and the other side passive." I said driving the two sides home.

"Passive..."

"Just like in a relationship... One partner is dominating and the other passive. In our relationship who is dominate Jim?"

He seemed to frown as he worked it out, "You dominate?"

"Yes... good... you're so special to me. So good and loved. Mine now and forever more." I said rewarding and reassuring him. "You trust me and listen to what I tell you to do because it makes you feel good right?"

Yes" again the smile came through in his voice.

"Now... back to the sides of a person. "Who wears panties? Male or female?"

"Female"

"Who wears pantyhose?"

"Female"

Who wears lovely boots?"

"Female"

"So knowing females wear all these, what is your dominate side?"

"Female" I expected him to delay but the word came out almost before I finished the question. It seemed that Jim has had this desire a bit longer then something I planted in him.

"Good girl" I said and the smile that had had almost shown finally broke through. "When did you first dress up dear?" I asked realizing that I had opened Pandora's Box.

"Fifteen," He said in reply not hesitating.

"Good girl, and what is your name, your female name?" I asked. I made a mental note to see if I could get him to talk about it once he was awake so I could get the full story.

"Name?"

"Yes name, I bet it is Rebecca. A beautiful name for a beautiful girl like you." I paused and then added, "You like your name don't you?"

"Rebecca, yes"

"Do you trust me?" I asked pausing a moment.

"Trust, yes..."

"Good, between now and Monday I would like you to do me a favor. You like doing things for me right?"

"Yes"

"Good girl... Between now and Monday, let Rebecca come out all the way. Let your inner woman be free. You want to do that don't you?"

"Yes"

"Now when I count to three you will wake up, Rebecca will be fully awake and Jim will be resting in the background. Watching and enjoying."

"One... Two... waking up now... Three... fully awake." I smiled as Jim's eyes fluttered open. "Welcome out my good girl." I said and leaned in to kiss Rebecca. The whole way Jim moved and the timber of his voice was completely different. It was not that he moved as if he were a gay man. He moved as if he were a woman.

Her first words were, "Thank you for freeing me." She kissed me deeply and passionately.

Sliding down the pantyhose and panties I made passionate love with Rebecca. Her style was totally different then Jims. If I did not know better, I would have sworn it was someone else. The equipment was the same but how she used it was as different as night and day as Jim's was. I had a taste of it the first time he had worn boots but this was much more intense.

There was one interesting thing of note as Rebecca made love to me, as we slowed down she said softly into my ear, "I love you, mistress."

"Wife, lover, mistress" I said correcting. "Get some sleep darling, tomorrow will be a busy day"

"Yes mistress" Rebecca replied and after I turned off the lights she snuggled up tight against me.

Morning found me alone in the bed. Frankly in the past Jim had always been the one to sleep in. But today was different. As I sat up looking around confusedly I was Rebecca totter into the room carrying a thermos. She was wearing my Tinkerbelle sleep tee, hose and the boots. Sitting down on the edge of the bed she smiled and poured me a cup of coffee. "Good morning my love." She said as she handed me the cup. "I thought you would like coffee in bed this morning."

I smiled in return. Normally I like lots of sugar in my coffee but figured if she went through all the trouble of walking on her own to the bedroom I could at least drink it with a smile. To my surprise the coffee had sugar in it. Taking a sip, I smiled, "Nothing like a cup of coffee delivered by so beautiful a lady." I said and kissed her.

I guess I need to digress here a moment. Looking at Rebecca you would see a plain looking woman, flat chested, in need of a makeover, and her eyebrows shaped. With the exception of her small Adam's apple she could pass as a woman. Jim for as long as I knew him had kept his hair long and pulled back into a pony tail. Rebecca while not having fashion sense had simply removed the tie and let her hair drape over her shoulders.

I sat there looking at her realizing that with the right makeup and clothing Rebecca would look devastatingly beautiful. I was stunned to say the least. After a moment she asked me a worried tone filling her voice, "What's wrong?"

"You're beautiful," I said in a hushed voice. While Jim was handsome this new part of him sent thrills of pleasure coursing through me. I wanted nothing more to lay down with her, and ravish this beauty. Instead I sipped my coffee and enjoyed her blush.

We sat in silence for a bit as I sipped my coffee. I could tell she wanted to ask or tell me something but I was determined to wait and let her bring it up.

After a few minutes she finally said in a quiet voice not looking at me, "Mistress, will you make me, teach me I mean..." her voice trailed off. She suddenly looked up at me and said, "Help me come out all the way."

"I will, if you tell me everything. It seems Jim has left something out about his past dear heart." I said taking her hand in mine. "But first..." I got out of bed and went to the dresser. I rummaged around until I found a padded bra. Handing it to Rebecca I said, "Put this on dear." Once she had it on I grabbed a couple pairs of Jim's tube socks and added them to the bra giving Rebecca a nice little B cup. Once she put the tee back on, if you had seen her from the shoulders down you would swear you were looking at a woman.

Sitting down on the couch over coffee with Rebecca snuggled up tight against me, I marveled how much different she was from Jim. In the whole time I had known him; he had never sat next to me and cuddled. Always in the past it was me who cuddled next to him. I realized with a shock that I really liked Rebecca. She was kind, considerate, cuddly, and everything Jim was lacking. I decided right then and there that I would make this weekend the best ever for her.

As we cuddled on the couch I learned what the deal with Jim and his past. It seemed that when Jim was fifteen, he spent a week at a summer camp. One of the councilors took a shine to him. She was a college student with a taste for voyeurism and though she never bedded him she did allow him and watch through the window as she pleasured herself. She never stripped down completely for his viewing pleasure. She would wear silky panties or pantyhose and masturbate with them covering her flower.

At the end of the week she cornered Jim and gave him a pair of panties and hose to remember her by. At first all he had to do was hold them to his face and capture her musky scent to get off. But as the scent wore off he moved to wearing the pantyhose and caressing his leg imaginings it was her leg under his hand. According to Rebecca, Jim could not get hard unless he was thinking about wearing hose. All through high school and college he kept a stash of woman's panties and hose to use to masturbate to.

Blushing she told me how even with me, that Jim had to imagine the hose on his legs to get hard. No wonder he agreed to wear the boots and pantyhose so readily I thought to myself. It must have been dreams come true for Jim. While I was surprised by all she said it did not compare to her next revelation.

"Would you like to see his stash?" Rebecca asked me with a twinkle in her eye.

"Stash?" I asked not quite following. I knew she was about to tell me he was into drugs. While I did not mind fetishes and thought I had a handle on his drinking problem. A drug problem was a whole other kettle of cats.

Rebecca smiled and took my hand. Leading me to the bathroom she got down on her hands and knees. Pulling out the bottom drawer she removed it and reached in the opening. She looked up at me and pulled out a couple pairs of my panties and pantyhose. While that was surprising it did not even come close to the silicone breast forms and bra that she then pulled out.

I looked at them and then at Rebecca, "Why... Why didn't Jim say anything?" I asked dumbfounded.

Rebecca looked up at me, tears overflowing, "He was scared you would call him a perv and kick him out."