I’ve tried a little back and forth about the sexual ladyboys thing, as I’m still married to a sweet and wonderful girl, and haven’t taken the big leap yet.
At the beginning of May, my wife came and told me that she wanted an 8-10 day holiday in the South, but had to disappoint her as I was too busy at work. I said she could just go with her good friend, enjoy the sun, beach and relaxation and we could travel together during the summer holidays, which were only 2 months away.
So it was, one Saturday morning we drove the two girls to the airport and waved goodbye, and happy holidays. The friend’s husband had to work a lot, so he drove straight to work. Since the weather was nice, I decided to go out for a bike ride. At home, I got the bike pumped and ready, but as I was leaving it turned to rain, so threw myself on the couch and started a chat website to see if anything happened. I was chatting to a couple of different guys when one of them texted to ask if we should meet at his place. He told me a bit about himself, a big guy at 190 cm, a bit of a belly, and was described as a nice guy.
Sweet and lovely girl called Mistress Mia
Quickly it was agreed that I should come to his house at 5.30pm, and dressed, as he lives in a house with a sand road and garden. He also wrote that one of his girlfriends might also be there, a sweet and lovely girl called Mistress Mia as he wrote. Then I went ahead with the transformation. A close shave, removing hair on my legs and crotch, so I was completely smooth.
Then a quick shower, and a conditioner, if it ended there. However, we had only written about licking and sucking each other, but also be on the safe side. Makeup for the big gold medal, mascara, red nails since I had time to remove it before Monday and bright red lips and some perfume. Nice lingerie with a halter top, long dress and the stilettos on. Last the wig, and hair was set nicely, then it was put in the bag, along with some extra clothes, dress folded, sweatpants and a sweater on, quickly out to the car so no one saw me, and off in good time. After a few miles, I trundled into a small rest area, pulled off the sweater and sweatpants, checked my makeup, set the wig neatly and straightened my hair, not to mention changed into stilettos, so I could arrive looking like a girl.
Have to say he lived in privacy, think there was at least 2-300 meters to nearest neighbor, so drive nicely in and park up along the house. Checked clothes and makeup one last time, grabbed my gym bag with a change of clothes and some extras, and went over and rang the bell, well nervous as it was our first time meeting. The door was opened by a rather pretty girl with a nice bosom, who welcomed me in. She took my bag and introduced herself as Mistress Mia, exactly as he had written. I expected her to take me further into the house, but she walked around me as if inspiring me.
Come she said, and we walked further down the hall, and she showed me into a room with a large bed, wardrobes, mirrors and a couple of nice sturdy oak chairs. Cheers for the dress girl, so I can see you’re keeping what you wrote to George. I looked at Mia and thought, what the hell, I had lingerie underneath, she had to see that, and what had I promised him? Mia looked at me, and asked if it was correctly understood from George and my conversation, that the wife was away for the next week, and I could only confirm that with some wonder.
She looked at me and told me to open my mouth
She pushed me gently but firmly into one of the chairs, and then she acted quickly, so that I did not have time to react to the fact that she put handcuffs on my wrists, so that my arms were tight around the back of the chair, I was about to say something, but was told to be quiet, and then it went quickly again, then my ankles were tied to each of the legs of the chair, and she continued with the rest of my body, so that I was completely stuck on the chair. Out she found a gag, looked at me and told me to open my mouth as she did not want to be disturbed in her work.
Couldn’t move her upper body, legs or arms, and when I followed her as she went over to one of the lockers, Mia returned with a wide collar which she fastened around her neck, so I couldn’t turn or bend my head. Mia walked around me a bit, grabbed my fake silicone breasts and played with them, nuzzling my cheeks and looking at me. I could just follow her with my eyes, and otherwise enjoy her caresses. Mia grabbed my bra and lifted it free of the silicone breasts I had glued on, as they look much more natural then. When she started playing with them again, I could feel my cock start to stir in the little thong panty. Mistress Mia looked at me, and asked if it was nice to have my breasts played with and if it was nice to have breasts. I could only nod in response, and could tell she was enjoying my answer. She grabbed them and started to remove them and I started to protest, but all I got out of it was a “shut up girl, you’ll get your boobs back”. She put them on a small bedside table and left the room.
Wondering, but hoping, that George would come so I could enjoy him. But it was her who came back in, bringing a small metal tray with something on it. Set it down on the bedside table, and started cleaning my nipples and around them with a spritz wipe, turned and showed me a big syringe with a needle, came over and grabbed my one nipple, stuck the needle in, looked at me and said, now you’re going to get real tits sissy that we can all enjoy. I tried to protest, and howl up, but only some mmm mm sounds came from me, and she ended up stabbing me 3 times in each nipple or just around. Could feel it tense wildly in my chest muscles, and pecked a little, but nothing helped against her.
She pulled my bra back over my chest
When she was done, she stood and looked at me and all she said was that it perked and pulled my bra back over my chest, without putting the silicone breasts in place. Felt like it actually fit well, but couldn’t get to look down or turn my head when I had that collar on. Mia went over to one of the closets, could hear she was looking for something in there, and came back with a cheeky short maid’s dress in black patent and a small apron in her hand. She untied me from the chairs, removed the gag, but announced that I was to keep the collar on, and when I saw it in the mirror, it sat like a collar up under my chin, and meant that my head was held in that position. But what surprised me most was that I had breasts, breasts the size of a B or C cup, and my nipples were straining in the bra. I turned around, but before I could say anything to her, she replied that they were much nicer than the artificial ones, and I was home alone the next day anyway, so we’d have to see if they were gone when my wife got home.
She helped me into the dress and I saw myself in the mirror, a nice looking maid. My cock was stroking, and it was commented by her that I couldn’t go in to the Lord like that, so Mia found a hard plastic chastity I could see in the mirror. She gave the cock a slap with her hand so I went to my knees with tears in my eyes, the cock shrank, and she quickly fitted the chastity to my tender cock, showed me the key and commanded me with a, follow me slut. I walked behind her through the hallway, and she opened a door into the living room, turned and showed me inside. Here’s your trans girl, George, hope you like her. I now saw George for the first time, and although I was wearing 12 cm high stilettos, I was still smaller, and weighing on the other side of 100 kg, he was and is a very large man compared to me.
He looked me straight in the eye, on your knees trans girl
Welcome girl, and how lovely you look, and can see you fit the maid dress perfectly, nice and tight on your luscious body. George walked around me, took me on the ass a bit and praised my appearance, commenting that I had charming breasts. He looked me straight in the eye, on your knees’ girl, and get your master’s cock out and take care of it. I squatted, sat with my legs slightly apart, and with fumbling hands got George’s pants open, pulled them down, but when I went to pull them all the way down, I toppled over as I couldn’t move my head. Mia was on me immediately and slapped me, not hard, but still one I could feel. If you fail again sissy, there goes my ass, she whispered into my ear. Hurriedly squatting back down, I got Lord’s underpants off, caught his big cock with my hand and enjoyed it. Poked my tongue out, played with the head, licked around it, let my tongue play with the hole, before taking the cock into my mouth and sucking it in well between my red lips.
Felt George’s big hand on the back of my neck, and let tongue out so cock could rest on it, then got fucked in my pussy mouth otherwise, MMM how good it tasted. Could feel him getting more and more demanding, couldn’t move his head to the side or down and up, so just received his big cock until I could hear him about to come in my mouth, felt it just grow the last bit, and then the cum came otherwise in my mouth. Sank it as best I could, but showed that with the load he was delivering, there had to be some running on the side. George pulled his cock out a bit and asked me to lick him clean, and then lick the floor clean after me, which came about with me having to tilt on my knees so I could get my head right down to the floor. I was told to get up, and then George would show me around the house. As he showed me around, he asked about my role as a maid, and had to tell the truth that it turned me on wildly to service a Lord or a couple when I was visiting.
George looked at me wonderingly, and asked if I intended to go to work as I looked, and suddenly I got to thinking that I couldn’t meet like that at work, with a pair of breasts in a B/C cup. I asked when they would be gone, and was told that it would be 5-7 days, and that I should take a vacation in the meantime. Yes, I thought, I’d be better, couldn’t show my face like that in the office. I looked up at George, and replied that I might have to work from home or take some holiday, and all he said was, I urge you to take the day off, girl. I was told that it would be my job to do the cleaning, cooking and servicing for him for the next week. At the same time, I was to be available to his guests, regardless of gender.
And then you appeal to me Lord, girl. If I have guests, you will address the men as Lord and the women as Lady. I declined for him, and answered yes Lord I was shown to my room, shown the closet with the clothes he wanted me in, always maid’s uniform when I cleaned or served meals, and long dresses in the evening if he thought I should sit at the table. I was told that today I was to cook for Mistress Mia and him, and I myself was welcome to sit at the table if I was properly dressed. The groceries had been bought, and I could in future order items, so they were delivered to my door.
I declined for the gentleman, thanked him, stood thinking for a moment, turned and went to the kitchen. It wasn’t much cooking he asked for, Gordonbleu, potatoes, a green salad and gravy to go with it, so figured that would be the “easy” chore for the week ahead. I set a nice table with candles and napkins, and managed to find time to change into a long dress beforehand. Could both see and feel that they were all long dresses, neat but low-cut and with slits in them, so found one in a dark green color that matched my stockings etc., so it didn’t need changing.
The only weird thing was that when I walked, I could clearly feel my breasts moving in time with my walk in the stilettos. Got the last thing done in the kitchen, somewhat inconvenienced by the collar I had to wear, and came in and put food neatly on the table, and announced that there was food. Could see that the Lord or Mistress had brought out good red wine, the Lord poured for us all, and we sat and enjoyed dinner together. The Lord looked at me, and asked Mistress if I had been told to sit down, and now she thought she had not heard. Get up, girl, commanded the Lord. I hurried to get up again, bowed nicely to the Lord and was about to apologize, but was interrupted by the Lord who told me to pull up my dress and stand with my hands on the table and or remain silent. So the Lord had brought out a paddle and now indicated that this would be the first punishment of many in the coming week.
20 strokes with the paddle
The Lord started softly, but after five soft, he started putting the effort in and ended up at 20 strokes with the paddle on my now red and sore ass. Then you can learn to wait for the shepherdess to settle and you’re allowed pussy, got it. Yes sir, as it faintly from me, could feel that I should not fail too often. Spread your bales, then you shall have a little that may soothe your red ass wench. I grabbed the balls and spread as much as I could, felt something cool, and suddenly a plug pushing up into me. Then you can enjoy that slut, and then you can sit down. Pulled my panties into place, my dress down, and sat down carefully at the table. The gentleman scooped me up, not much food, but enough so I could function. You need to lose some weight on your side bones, then you just eat salad for chick. Yes master.
Enjoyed the food and self-created, but refrained from interfering in the conversation. Was sent to the kitchen and refilled, and could clearly feel both the plug and my red ass when I sat down again, or I moved on the chair. After dinner and after I had cleaned up, I was asked to come into the living room. I gently knocked on the door and was assigned a seat on the couch next to Mistress Mia. I’ll let you know how it goes for the rest of the evening. In a little while, you will go into the bedroom and make up the master’s bed and lie up in it, but without your dress and stilettos. Then I’ll come and enjoy you. Thank you, Lord,” I said quietly, not yet knowing what the Lord had in mind, “I got up and went to the bedroom.
