I am Timothy: your… Ch. 04

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Ağu 31, 2023 // By:analsex // No Comment

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Christmas day was the best ever! It started in the morning when mom took me out of the dog box. I had been put in there because one of my presents started beeping and distracted me from serving mom. I had just started bringing mom to orgasm with my mouth when the beeping started. She let go of my hair to rub her breasts just before she reached orgasm and the beeping got to me and I went to switch it off… never stop halfway with mom; any girl in fact.

I spent Christmas Eve looking at that hoist and hoping like hell I didn’t get more bruises on top of the ones that were just starting to go deep blue and green. When she did take me out I was relieved to leave my room. We bathed together and mom started to dress me as a girl. What a feeling! I still prefer panties, they’re so silky and smooth. Mom even gave me a gaff, it pulled my dick and testicles between my legs so there wasn’t a bulge. And gave me long nails that I had to paint. At least the chastity cage was off and that was a big improvement.

“When are you going to punish me for last night My Lady?” I asked while mom dressed and we were waiting for my nails to dry.

“I did last night Boy.” She answered.

That was something she decided on Saturday night after we had sorted out what we were going to do. She could not let herself think of me as her son until we were settled and I could not think of her as mom. It started with the names. She was My Lady, I was Boy.

I was very relieved to hear that. She did her makeup and then showed me to kneel beside her and she did mine. That was amazing too, the way it all changed the way I looked. She even plucked my eyebrows to look more like a girl. She gave me a bra with fake breasts that she glued to my chest. They were surprisingly heavy. Mom explained that they were the same weight and feel as real breast; used by cosmetic surgeons to get gender reassignment patients used to what breasts will feel like. They did feel like real breasts at least with my hand on them.

Then I got the dress, a deep blue satin dress that came to the middle of my thighs. It looked fantastic and was warmer than I thought it would be. Mom’s last touch was a wig; the same color as my hair but this one had a pony tail then the shoes, nice black leather ballet shoes. I felt the pony tail between my shoulder blades and felt fantastic.

“For these times you will be Tina. We won’t go out today Tina, we’ll just practice today.”

“Yes My Lady.” I answered.

“We’ll need to work on your voice too. Let’s go and have breakfast.” Mom said and let us go downstairs.

I cooked, I cook better than mom. Mind you I cook better than our… never mind, later story. We chatted as we did, then I was Timothy and she was mom. I asked if I could change my underwear for panties. Mom agreed that I could because they were also better with chastity cages than the briefs I usually wore. Mom wanted to know if she should buy me pajamas, we hadn’t worn much in the line of bed clothes yet.

“Mom, I never wore pajamas, it’s too hot in the Azores. But I think you should choose that.”

“Hmm, how about some nice nighties, short ones?”

“You mean like little night dresses? Easier for you to see my ass to spank or get to the other side? Sure mom, I’d like that.”

We chatted on with me actually keen to get to the presents. It was while I was cleaning up that I asked for mom to do something.

“Mom? Would you uhm. You know sort of let me give my balls to you to do what you like to them?”

“Do you want me to hurt them?” mom asked.

“uhm sort of like a show that I am your Boy from time to time… like present them and you decide. If I don’t then you know something is up… it’s hard to explain.”

“Not at all hard, you just did a wonderful job. You want to prove to yourself and to me that you are mine. It’s very mature of you to understand that feelings might change and you want to test yours and give me a way to see. I like that.” Mom said.

One thing that was getting to me about this outfit was the long nails. Doing anything was different. I couldn’t hold anything the way I was used to. I commented on that as mom said breakfast was over and we went back to My Lady and Tina. She smiled and agreed, it was easier if they grew and you got used to them as they got longer she said.

We took turns, mom would pick a present Diyarbakır Escort for me and then I would pick a present for her. she first gave me an office bundle, a briefcase with a new laptop, phone, and tablet inside. It had been the tablet going off last night, I put them to one side and gave mom my first present, a pair of earrings with tiny deep blue diamonds. She stared at them in delight they were really good and fitted her face beautifully. Then she started with the other presents. She gave me a Barbie doll. I gave her a matching neck chain to the earrings. She gave me a Barbie wardrobe, I gave her some bracelets and she gave me another doll.

My next present was an angora rabbit wool pair of gloves for cold mornings. Then I got more doll’s clothes. And the last present I had was a silk blouse in peach. Mom sent me to the storm cellar and came after me as she gave me a huge doll’s house and a table with a train set laid out. She explained that the old man I had visited with the trains was too old to play now and was happy to give them to me. I was deeply flattered and asked if we could go and say thank you in the morning. But the doll’s house! That was now.

Mom and I spent the morning playing dolls. I carried the doll’s house to the lounge and we lay on our stomachs playing. We had a make believe fetish party with Barbie dolls and Ken being disciplined to mom’s fantastic laughter. Then Barbie got turned into a slut for Ken by some of Barbie’s friends. We had a time of just playing house. Mom just hugged me a couple of times as we played.

“You’re wonderful. Don’t believe anything else!” Mom said to me when we decided to have lunch.

“Just trying to give you what you should have mom.”

The spank was immediate and hard! Mom might have been having a fantastic time but she was still my mistress. I didn’t mind the spank, she was right. After lunch my back started hurting from the weight of the breasts. Mom saw and smiled but didn’t stop as we played cards.

“My Lady? There is a cosmetic surgeon in Jacksonville that can put temporary breasts in. He uses them to stretch the skin for breast implants. These are great but if you want we can try that and then you could feel them?” I said while mom shuffled after I lost a hand of canasta.

“It shows? Ah you watch people very well. Would you do that?” Mom asked.

“Yes I would, I found out about it, my secretary, jeez grandad had me get one. She was talking to another woman; she, my secretary, thought bigger breasts would get her jobs more easily. They didn’t know I was the boss as I waited at HR. You should have seen their faces!”

Mom laughed at the image. She said she would find out for us about how long it took and when we could do it. She asked about my back being sore, it was just muscles I explained. They just had to get stronger. The only way for that to happen was to carry the weight. She nodded about that.

“Do you find that sexy Tina?” mom asked.

“That’s hard to explain My Lady. Do I want to be treated like a girl? No. do I want to be screwed in the ass by some guy? No. Do I want you to screw me in the ass? Yes my lady, but I don’t need to be dressed like this. If you would like me dressed like this, that’s fine. I like this for a change; it’s an adventure and I’ve learned something of what you do to look your best. Yes, I would like to do this again and I would love to go out with you, like this if you want.”

Mom smiled and poured us some sherry.

“I’ve never smiled so much… why did you ask for sherry at mom?” Mom asked.

“To see how grandma would react. I do like sherry, especially a South African sherry called Old Brown. The big thing was I wanted to see because she was prepared for rum, whisky, beer, something like that. I also told grandma something.”

“What did you tell?” Mom was genuinely interested.

“That I will not follow convention if it’s stupid. That I have particular standards. The sherry was hidden, the whisky and rum were being shown. She wanted me to pick one of those. She picked up that I would not be prescribed to by her. That is your privilege, only yours mom…. Ah shhhh poot!”

Mom just waved upstairs and ordered the cane as she laughed. She draped my dress over my lower back and caned me twelve. Then kissed my tears and hugged me to tell me that it Diyarbakır Escort Bayan was over. She had me go and fix my makeup and put the cane away after that. When I got back with a stinging eye because mascara is hard she was cooking supper.

The glue holding my breasts in place started coming lose while we ate supper. Mom nodded and said she was surprised the glue had held as long as it did. We watched some television about what was happening in the world before going to bed. When I was out of the dress and back to being boy mom kissed me out of nowhere.

‘Thank you for a wonderful Christmas.” Mom whispered.

“Thank you. You’re the best. You’re just simply… Mom. Everything that means and more.” I whispered back.

Mom heard the capital letter and she looked at me quizzically.

“It doesn’t matter to you does it? Whether I’m Vivienne, or My Lady, or mom, you have decided that you love me and want to be my submissive, you’ll do your utmost to be what I need.” She said quietly.

“It matters, because it matters to you.”

The next day was first saying thank you to the old man who had given me his train set. He was incredibly old and nearly blind. His mind wandered and he thought I was his grandson most of the time. His granddaughter watched over him as he slipped into a past memory and went to sleep without warning.

She gave me a hug as we left and tried a kiss but I made sure her tongue missed my mouth. I would not have been interested had I been alone. Mom watched and saw my turn as soon as I realized there was going to be tongue in the kiss. Her jaw dropped that I did that.

“Why didn’t you let her kiss you?” mom asked.

“Because I’m weird.”

“Not that weird. Why not?”

“It’s not just about the body, not for me. There is not a thing I could think of to speak to her about. She looked at the car and the clothing labels… There has to be more than a body, I see lots of those. There has to be a brain, a personality, a soul… a package deal. You’re not an easy package My Lady, but you are everything I want and need and more. Most of the reason I never had a girlfriend? They weren’t you.”

“Someday; I’m going have to beat you to seduce a girlfriend for us. And when you do, I’m going to have to beat her to keep her from screwing you to death! My Boy! You can flatter!”

We shopped around and I had a look at the narrow entry to New River. There was no way I was going to get anything bigger than my cruiser in there. We had a look at mom’s school, an old hotel in the way of a new infrastructure project being planned to start in august. I could understand why she hated running the place. She explained that grandma had bought the hotel as soon as mom had come up with the idea. Mom herself would have chosen to use a farm. I agreed with mom. The hotel was high maintenance, too open to the wrong people wandering in, and the rates cut most of the profit margin.

She told me that she had decided to close the school down. She didn’t want a floating school, she was in fact looking for something else. I suggested the fuel station at the marina. I knew the guy from the Canary Islands where he had been forced to run away for selling short measures. I was confident he was doing it again from what I heard among the skippers there.

Mom listened to this and smiled as she drove us home. It was a business away from grandma and a chance to prove something to herself. When I talked about how there was space for a competing station just next to the marina that might be better because she would need to fight a bad reputation to begin if she took the old place. But she could get a massive market if she offered a good product before the other guy went down.

“You’re serious! You’re supporting me!” she said as we went into the house.

“Yes, I know the type grandma is. She will keep anybody dependent on her just to have the ability to make them shit themselves if she threatens. She knows that doesn’t work with me. So she has to be nice. The moment you show grandma you can do it without her she will be different.”

“Do you like mom?”

“I love her, but I know she’s a bitch if you back down to her because then she can be and you won’t slap her silly.”

“What do you think of dad?”

“He loves being where he is mom. He looks important Escort Diyarbakır but isn’t really. He brings the big decisions home for grandma. When they host dinners or something for big customers, nobody pays attention to her and she figures them out without them knowing.”

“How would you work if you had the company?”

“I’m years away from even thinking about that.”

Mom had closed the door and I stripped. That was the rule unless mom said otherwise. Mom watched me undress; a look on her face of complete love. I held out my hands and she put the cuff on each wrist then I knelt and she put my collar on.

“I missed them while we were out.” I said, surprising myself.

“I missed seeing your collar… there. Nicely on. I love that I don’t have to dress like a dominatrix for you. I know you love seeing me in an outfit but you don’t need me to be in one.”

“Isn’t that the point mo-My Lady?”

Mom smiled at my near slip. She tidied my hair while I was kneeling.

“Very few get that point my boy. Make us some coffee, I’m going to get your office things ready. Why were you looking at that old boat in the marina?”

“It’s ninety minutes to the office by road with traffic. It’s twenty five by water on a fast boat. That boat is fast and I can modify it to ferry a car while still fitting under the bridges.” I said going to the kitchen.

“And no speeding fines. What about the marines?”

“I hope they see it and ask us to build them some. I got a team of engineers I have to give them something to do. Let’s see how they do on small ships before I put them onto much more expensive ships.”

Mom laughed about that. I put the coffee down as mom took the laptop out of the box. I went to find an extension cord and mom started up when we had power there. She looked at me while it was starting up and made a decision.

“When I tell you Presentation Position you stand in front of me with your feet far apart. Come stand here in your Presentation Position… Feet further apart, there, now bend your knees, there, now lift your penis up.”

I did as she said and stood between her and the computer with my balls hanging below my body. I just knew this was an ideal position to kick or smack or just feel them. I stood nervously as mom fondled my testicles.

“Hmm, they’re full.” Mom said.

“How can you tell My Lady?”

“The way they move look, empty they don’t look like little eggs…” Mom said then slapped them.

I took a deep breath and my knees started coming together.

“STAND STILL!” she barked the order loudly.

I stood still breathing heavily. She slapped again and I shivered as I stood. Mom nodded approval and fondled them a bit. She patted them before telling me to sit beside her; then we started setting the office things up. We were busy with getting my email up when mom spoke again.

“Why no tattoos?” she asked.

“You need time, money, and to be over eighteen to get a tattoo. Passengers have no trouble being tattooed, they have trouble with a captain who has visible tattoos; one that has a story behind it is fine. Besides that? I never really thought about it.”

“What kind of tattoo would you like if you had one?”

“I don’t know. I once ran into a sailor who had been tattooed in prison. Across his forehead was a tattoo writing that said; “What are you staring at cu…” I just can’t.” I said shaking my head.

Mom hugged me as she laughed about the tattoo. She agreed that kind of tattoo was out of the question. I poured us drinks thinking about tattoos. When I came back I had more to offer about that.

“It depends on what the tattoos are for I suppose. Most of the tattoos I saw on passengers were a joke. They said the person had too much time, too much money to know what to do with, and nothing to say really. They looked pretty but that’s it. On sailors, soldiers, ex-convicts, yakuza, triads, the tattoos say something important. They are like memories or a reminder, or evidence, or a mark of rank. They say the person you’re dealing with has experience in things that don’t leave scars you can see, belongs…” I said sitting down.

“That is interesting. It’s often same in D/s relationships. A tattoo is a mark of ownership.”

“Tattoos can be changed or even removed these days. Nothing says ownership like branding though. I’ve seen those too. The scar will always be there, it cannot be modified or changed if you change your mind about how you feel.”

Mom was quiet about that for a few moments.

“I’m going to get you tattooed. The question is what tattoo? A rose? A cherry?”

“The doll’s house? I mean that is something we have…”

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