Jamie s Gradual Grooming Part 2
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Jamie's Gradual Grooming, Part 3a free porn video
I gradually woke up from a deep and warm sleep. My slow awakening became very sudden as I came to two realisations. One, I was wearing underwear from the night before and two, they were wet!
I quickly pulled the duvet up and over my head, as if lots of people were watching. I slowly put my hands into my panties and felt a warm liquid all over them, I'd had a wet dream.
Straight away I tried to think about what I had dreamt, but I couldn't recall. I wondered what Mike would say and what he would think, what did I think? Did I cum because of what I was wearing?
I tried to snap out of it by running and jumping into the shower, I needed to remove any evidence and go down for breakfast. I quickly washed and took care to wash my new underwear in order to leave nothing behind. As I dried off I looked around my room for my one set of clothes. I remembered taking them off the night before to put on my new underwear but couldn't see them anywhere. I put on an old dressing gown and went down for breakfast.
I called to Mike as I got to the bottom of the stairs, wondering what he would say about the night before, would he want to pick up where he left off? Would I want him to? Was that why I had a wet dream?
Mike didn't respond. I looked in the garage and the garden but he wasn't there either. Again my mind started to race, had I taken things too far the night before? Had I upset him? I then noticed a note attached to a magnet on the fridge.
"Morning Jamie, sorry I am not there to see you this morning, I have had to go out on some urgent business but will be back mid afternoon. I hope you will forgive me but I have binned your clothes as they were looking very worn out. I know we do not have any clothes for you in the house, but I am sure you can think of something until we get to the shops. I look forward to seeing you later today, Mike"
I didn't know whether to scream or cry, I now had no clothes in the world other than the underwear Mike gave me last night and I couldn't go anywhere in that. What did Mike mean when he said "I am sure you can think of something"? Was he referring to me dressing up more? I was tempted! What if I was totally wrong?
I sat down and had some breakfast, all the time I thought about what Mike had meant, rereading his note and trying to figure out what I should do. Mike wasn't back until later today so if I had a look in Phillippa's room, he wouldn't know and I wouldn't be embarrassed. I didn't have anything to lose, I thought, and I was bored already and slightly turned on after last night's adventure.
I ran up the stairs like a kid playing hide and seek and quickly moved towards Phillippa's room. I stopped dead before it, I felt like if I entered there, there was no going back, but I quickly assured myself that that was silly and I was purely entertaining myself in a big empty house.
As I opened the door, a number of familiar smells drifted out of the room. Happy childhood memories and experiences came flooding back. I instantly felt guilt as this wasn't my room and nothing in it was mine either. I walked further into the room, it was just how I remembered it, but there was something different but equally familiar. Another note, identical to the one on the fridge, lay on the bed, it had my name on it.
"Jamie, if you are reading this then you have decided to explore dressing up further, I knew you would and am delighted. I also knew that you would feel guilty dressing in Phillippa's clothes and if I am honest. I would feel guilty looking at you in them, too. So, I have brought a few outfits and items that will fit you and will be yours if you chose to wear them. There is no pressure to wear these things and if you do not enjoy it then we can go shopping for boys clothes tomorrow. Have fun and I can't wait to see you at 2pm in the living room, love Mike."
I was in a state of shock, Mike was two steps ahead of me and it felt good. I instantly felt safe and all my anxieties about dressing up were gone. If I enjoyed it, great, if not it didn't matter. Similar to my present the night before I was like a kid at Christmas, I wanted to see what Mike had got for me. There were three outfits in the wardrobe as well as some shoes, make up and a further black box that looked interesting.
I decided to try on the skin tight pink dress, I don't know what it is called in the shops, but I will describe it. It was baby pink, skin tight and stretchy, it had straps over my shoulders that were thin and a slit at the front that would show my boobs if I had any, it ended just below my rib cage. The bottom of the dress just covered my bottom, but it felt good and fitted me well. I was already thinking like a women as I popped back to my room to slip on my new underwear!
It was 12 on and Mike would be home in two hours, I looked at myself in the mirror and felt I looked good but I didn't look like a real girl yet. I had to put on some make up and sort out my hair. I quickly stripped off and showered, this shower had all flowery lotions and moisturisers. I put them all over and washed my hair, I smelt amazing and very girly. I went over to the dressing table and quickly figured out how to use the hair straighteners and attempted to straighten my hair with a little girly flick at the end, it worked more or less and instantly my face became more feminine.
I had a look at the makeup that Mike had left and given the fact I had never applied makeup before I decided to keep it simple. I put on some foundation and blusher, pink lipstick and put on some mascara, that was difficult!
It was just after 1pm, I was starting to have second thoughts and get very nervous. I decided to paint my nails to distract myself, I might as well go all the way and hopefully impress Mike. I did my best and was finally finished but for a pair of slip on heeled shoes Mike had left. They were lovely, again baby pink, low heels that made my legs look like an Olympic runner.
I sat on the edge of the bed and began to think, what if Mike liked me dressed? What would he expect next? Did I actually like Mike enough to do anything with him? Was I gay if I did? The door went, Mike was trying to open the door, he was early. I shouted down "Wait, I am not in the living room yet!" It went quiet, that was my cue to get downstairs and be ready for Mike, even if he was early.
I stood in the middle of the living room as I had done the night before, I shouted through for Mike to come in. Mike put down what sounded like shopping bags and his keys. He slowly walked into the living room, my heart was pounding and I instantly wanted to run away. Mike instantly smiled, that put me a little more at ease. "You look just as I had pictured in my head, only better!" he said. I smiled too and twisted on my heels as I blushed.
Mike walked around me to have a good look, with him it didn't feel pervy, it felt like he was looking at me, testing me or judging me but not in a bad way. "Would you mind if I touched your clothes Jamie?" he asked.
I giggled a little and wasn't sure what to say. "Yes....please," I said, please!? Where did that come from? I can't believe I had given Mike permission to touch me and I had encouraged him.
Mike ran his fingers down my back as he had some previously all the way down to the bottom of my dress, it sent shock waves through my body. He then stroked from my heels, up the back of my calf to the bottom of my dress again. All the time I stood there paralysed by anticipation and curiosity. Mike moved around to face me, he slowly moved his finger across my college bone and down the front slit of my dress, up and down, very slowly. I couldn't help it, I began to get hard underneath my dress.
Mike gestured for me to get on my knees, where was this going? He cupped my face with his one hand as I looked up at him. He stroked his index finger across my lips smudging my new lipstick as he moved in a circular motion. I opened my mouth a little without thinking, subconsciously encouraging his finger into my mouth. He circular motion began to enter my mouth a little, teasing my lips as my mouth breath warmed his finger.
Mike stopped, what had I done wrong? Mike looked everywhere, but at me and mumbled under his breathe.
"Mike please don't stop I am enjoying this, I promise" I pleaded.
"I can't, not like this, not with that," Mike said as he pointed at my twitching cock.
I felt ashamed, Mike wanted a real girl not a stupid boy dressed up. I apologised to Mike for getting so turned on and for not being able to be the real girl he wanted. Mike's eyes lit up from nowhere, like a patient predator that had finally caught it's prey.
"There is one way you could be a real girl for me, or as close as you can be but...."
I cut over Mike in desperation, "What is it? I will do it Mike, I will."
Mike asked me if I had seen a black box in the wardrobe, which I had and if I could go and get it. I wondered what was in the box and now I would find out. Mike opened the box and took out a small metal cage. I hadn't a clue what it was but Mike quickly explained. It was called a chastity device and it meant the person wearing it cannot get an erection. I don't know what I was expecting but it wasn't this, I wasn't sure what to do but I didn't want to disappoint Mike and I liked the things he had started to do to me.
"If you agree to wear this Jamie, you need to know it will be padlocked, so it won't be coming off for a while and I will have the key," said Mike, as his words instantly increased my anxiety.
I wanted to please Mike but I wasn't sure about being locked up with no escape. Mike looked at me as if he knew I would agree. I agreed, I liked living with Mike and wanted to please him and if this helped, it was a small price to pay, surely?
I quickly pulled the duvet up and over my head, as if lots of people were watching. I slowly put my hands into my panties and felt a warm liquid all over them, I'd had a wet dream.
Straight away I tried to think about what I had dreamt, but I couldn't recall. I wondered what Mike would say and what he would think, what did I think? Did I cum because of what I was wearing?
I tried to snap out of it by running and jumping into the shower, I needed to remove any evidence and go down for breakfast. I quickly washed and took care to wash my new underwear in order to leave nothing behind. As I dried off I looked around my room for my one set of clothes. I remembered taking them off the night before to put on my new underwear but couldn't see them anywhere. I put on an old dressing gown and went down for breakfast.
I called to Mike as I got to the bottom of the stairs, wondering what he would say about the night before, would he want to pick up where he left off? Would I want him to? Was that why I had a wet dream?
Mike didn't respond. I looked in the garage and the garden but he wasn't there either. Again my mind started to race, had I taken things too far the night before? Had I upset him? I then noticed a note attached to a magnet on the fridge.
"Morning Jamie, sorry I am not there to see you this morning, I have had to go out on some urgent business but will be back mid afternoon. I hope you will forgive me but I have binned your clothes as they were looking very worn out. I know we do not have any clothes for you in the house, but I am sure you can think of something until we get to the shops. I look forward to seeing you later today, Mike"
I didn't know whether to scream or cry, I now had no clothes in the world other than the underwear Mike gave me last night and I couldn't go anywhere in that. What did Mike mean when he said "I am sure you can think of something"? Was he referring to me dressing up more? I was tempted! What if I was totally wrong?
I sat down and had some breakfast, all the time I thought about what Mike had meant, rereading his note and trying to figure out what I should do. Mike wasn't back until later today so if I had a look in Phillippa's room, he wouldn't know and I wouldn't be embarrassed. I didn't have anything to lose, I thought, and I was bored already and slightly turned on after last night's adventure.
I ran up the stairs like a kid playing hide and seek and quickly moved towards Phillippa's room. I stopped dead before it, I felt like if I entered there, there was no going back, but I quickly assured myself that that was silly and I was purely entertaining myself in a big empty house.
As I opened the door, a number of familiar smells drifted out of the room. Happy childhood memories and experiences came flooding back. I instantly felt guilt as this wasn't my room and nothing in it was mine either. I walked further into the room, it was just how I remembered it, but there was something different but equally familiar. Another note, identical to the one on the fridge, lay on the bed, it had my name on it.
"Jamie, if you are reading this then you have decided to explore dressing up further, I knew you would and am delighted. I also knew that you would feel guilty dressing in Phillippa's clothes and if I am honest. I would feel guilty looking at you in them, too. So, I have brought a few outfits and items that will fit you and will be yours if you chose to wear them. There is no pressure to wear these things and if you do not enjoy it then we can go shopping for boys clothes tomorrow. Have fun and I can't wait to see you at 2pm in the living room, love Mike."
I was in a state of shock, Mike was two steps ahead of me and it felt good. I instantly felt safe and all my anxieties about dressing up were gone. If I enjoyed it, great, if not it didn't matter. Similar to my present the night before I was like a kid at Christmas, I wanted to see what Mike had got for me. There were three outfits in the wardrobe as well as some shoes, make up and a further black box that looked interesting.
I decided to try on the skin tight pink dress, I don't know what it is called in the shops, but I will describe it. It was baby pink, skin tight and stretchy, it had straps over my shoulders that were thin and a slit at the front that would show my boobs if I had any, it ended just below my rib cage. The bottom of the dress just covered my bottom, but it felt good and fitted me well. I was already thinking like a women as I popped back to my room to slip on my new underwear!
It was 12 on and Mike would be home in two hours, I looked at myself in the mirror and felt I looked good but I didn't look like a real girl yet. I had to put on some make up and sort out my hair. I quickly stripped off and showered, this shower had all flowery lotions and moisturisers. I put them all over and washed my hair, I smelt amazing and very girly. I went over to the dressing table and quickly figured out how to use the hair straighteners and attempted to straighten my hair with a little girly flick at the end, it worked more or less and instantly my face became more feminine.
I had a look at the makeup that Mike had left and given the fact I had never applied makeup before I decided to keep it simple. I put on some foundation and blusher, pink lipstick and put on some mascara, that was difficult!
It was just after 1pm, I was starting to have second thoughts and get very nervous. I decided to paint my nails to distract myself, I might as well go all the way and hopefully impress Mike. I did my best and was finally finished but for a pair of slip on heeled shoes Mike had left. They were lovely, again baby pink, low heels that made my legs look like an Olympic runner.
I sat on the edge of the bed and began to think, what if Mike liked me dressed? What would he expect next? Did I actually like Mike enough to do anything with him? Was I gay if I did? The door went, Mike was trying to open the door, he was early. I shouted down "Wait, I am not in the living room yet!" It went quiet, that was my cue to get downstairs and be ready for Mike, even if he was early.
I stood in the middle of the living room as I had done the night before, I shouted through for Mike to come in. Mike put down what sounded like shopping bags and his keys. He slowly walked into the living room, my heart was pounding and I instantly wanted to run away. Mike instantly smiled, that put me a little more at ease. "You look just as I had pictured in my head, only better!" he said. I smiled too and twisted on my heels as I blushed.
Mike walked around me to have a good look, with him it didn't feel pervy, it felt like he was looking at me, testing me or judging me but not in a bad way. "Would you mind if I touched your clothes Jamie?" he asked.
I giggled a little and wasn't sure what to say. "Yes....please," I said, please!? Where did that come from? I can't believe I had given Mike permission to touch me and I had encouraged him.
Mike ran his fingers down my back as he had some previously all the way down to the bottom of my dress, it sent shock waves through my body. He then stroked from my heels, up the back of my calf to the bottom of my dress again. All the time I stood there paralysed by anticipation and curiosity. Mike moved around to face me, he slowly moved his finger across my college bone and down the front slit of my dress, up and down, very slowly. I couldn't help it, I began to get hard underneath my dress.
Mike gestured for me to get on my knees, where was this going? He cupped my face with his one hand as I looked up at him. He stroked his index finger across my lips smudging my new lipstick as he moved in a circular motion. I opened my mouth a little without thinking, subconsciously encouraging his finger into my mouth. He circular motion began to enter my mouth a little, teasing my lips as my mouth breath warmed his finger.
Mike stopped, what had I done wrong? Mike looked everywhere, but at me and mumbled under his breathe.
"Mike please don't stop I am enjoying this, I promise" I pleaded.
"I can't, not like this, not with that," Mike said as he pointed at my twitching cock.
I felt ashamed, Mike wanted a real girl not a stupid boy dressed up. I apologised to Mike for getting so turned on and for not being able to be the real girl he wanted. Mike's eyes lit up from nowhere, like a patient predator that had finally caught it's prey.
"There is one way you could be a real girl for me, or as close as you can be but...."
I cut over Mike in desperation, "What is it? I will do it Mike, I will."
Mike asked me if I had seen a black box in the wardrobe, which I had and if I could go and get it. I wondered what was in the box and now I would find out. Mike opened the box and took out a small metal cage. I hadn't a clue what it was but Mike quickly explained. It was called a chastity device and it meant the person wearing it cannot get an erection. I don't know what I was expecting but it wasn't this, I wasn't sure what to do but I didn't want to disappoint Mike and I liked the things he had started to do to me.
"If you agree to wear this Jamie, you need to know it will be padlocked, so it won't be coming off for a while and I will have the key," said Mike, as his words instantly increased my anxiety.
I wanted to please Mike but I wasn't sure about being locked up with no escape. Mike looked at me as if he knew I would agree. I agreed, I liked living with Mike and wanted to please him and if this helped, it was a small price to pay, surely?
Hester
- 21.04.2022
- 26
- 0
- Category:
- Crossdressing
