She Was More Into It Than I Thought

It’s completely true. Even reading it now, I can hardly believe it; if someone else had told me this a year ago, I would have thought they were lying.

Here goes. Enjoy the story.

It all began one day before our planned trip. Dana suggested we take a bath together. We had been enjoying romantic baths with candles and lots of foam. Suddenly, she handed me my razor and said: “Shave everything. Legs, ass, balls, hands. Go ahead.” I told her about my little obsession with women’s clothes, but I never shaved myself before. I was already starting to feel embarrassed. So I did it completely. After the bath, she trimmed my long hair a bit so it looked much more like a woman’s hairstyle. When she was satisfied, she put me into chastity and ordered me to service her with my mouth. It took some time before she was happy. We went to bed.

I woke up first and immediately started preparing for our trip. I have two suitcases full of high heels, boots, clothes, and accessories. I checked that I packed all the chains, padlocks, hooks, rings, leather cuffs, lots of ropes totaling about 100m, my hood, two gags, dildoes (one improved with a rubber hose inside for squirting), vibrating egg, nipple clamps, homemade nipple sucker, and other small items. “Come here. For these three days, you will be my servant. My slave. My bitch. My maid. You will do everything I want. If you fail to do anything I ask of you, you will be punished. You will spend these three days as a girl only. Even at night. Understand?” “Yes, I do, my Princess.” “Now come here, you slut. We need to work on your appearance.” It was just ten in the morning. I thought I would turn into a woman once we arrived at the cottage. It is in a secluded spot where you don’t meet many people. The situation is different in the city where we live. “I have some presents for you,” she said while taking fake breasts from her bag. She applied glue and placed them. She secured them with elastic material as well. Then she took skin-colored covering makeup to mask any imperfections. “I spent a lot of money on this, especially the makeup. It won’t come off even if you sweat.” Dana handed me a pink laced bra, which I put on. Then I tried walking and felt the weight of my breasts; I saw their lovely bouncing movement. It was exciting, but since I was still in chastity, I tried to change my thoughts. Thankfully, my mistress removed the chastity device but immediately pulled another unknown item from her bag. They were flesh-colored latex panties with an inflatable dildo inside. The pump was removable and had a connector as well. I had to put them on. I lubricated the inner part; thankfully it wasn’t too big—yet. I inserted it into my ass and secured my balls and cock in place within the panties. Once I finished positioning, my male parts were effectively hidden. I felt a little pressure inside and out, but I had to get used to it. I put pink lace panties over the latex ones.

I needed to finish grooming myself. I oiled my body so my legs looked nice and shiny; they are very long and girly. Dana decided to dress me in a pink tank top, denim mini skirt with a pink belt, and pink 10cm pump heels which she padlocked onto my ankles. She did my hair and makeup. I couldn’t look into the mirror until it was completed; I hardly recognized myself. I put on my fake earrings, necklace, bracelets (one for my leg), some rings (one for a toe). All silver. Dana then placed a wide silver metal collar around my neck with “SEX SLAVE” engraved on it.

I looked like a complete woman. A bit tall due to the heels bringing me nearly 2 meters in height, and with broad shoulders. But overall, I had a great feeling; I really did look like a woman.

I finished packing while dressed that way and put everything in the car. My feet were already hurting, not to mention my insides. But I was enjoying it, trying out a catwalk gait. When all was ready, Dana simply placed leather cuffs on my wrists and locked them together. She gave me a ball gag and covered my eyes. I was ordered into the trunk of the car. Once I squeezed in, she locked my wrist cuffs. I was so excited yet scared at the same time. But I felt relieved that I wouldn’t have to drive from our garage.

She drove away. After a while, she let me out, removed my eye blindfold, and I realized it was only about 10km from our home. Still, many people here can recognize me. She took all the bondage gear off me and handed me the keys. “You drive now.” “Me? Are you crazy?” “What did you say? You little bitch? Do I drive alone, or do you drive but alone too?”

I went to the car. She even got me pink trainers so I could drive easily. It was around a hundred miles. I felt embarrassed and worried all the way. I was scared someone would recognize me or see through my disguise. “Now is your test. Stop here at the shopping center and go in there for food supplies for these three days.” “What? That…” “Shut up! I don’t care what you think. You look fine; nobody will notice. You have a nice ass and tits. No one can tell you are a man. Stop being such a baby. Go.”

So I went in, sweating. Sunglasses helped me greatly, as well as the light neckpiece around my neck covering my Adam’s apple and the sex slave collar. I went through quickly doing my shopping. I couldn’t relax; I felt paranoid that everyone was staring at me (or so I thought). But nobody said anything, and after a while, my brain started thinking more clearly. Just one or two men took looks to check out the woman; no weird reactions. When I went to the till, I felt exposed. The shopkeeper asked me about some items, and I pretended not to be able to talk because I was sick. I just whispered a little thank you at the end. I had tried my voice earlier, but I didn’t think I could pass it off as natural. “See? It wasn’t that bad. Next time, I might send you somewhere else for a man,” she laughed.

We finally arrived at the cottage. It was 2 pm. “Go get changed. No accessories; slaves don’t wear silver.” She ordered me to put on 12cm black Oxford pumps, black leggings, to change my underwear to black, and to wear a sleeveless black top with latex gloves. She then installed cuffs on my wrists, knees, and ankles and locked each pair together with a chain, placing a bell on the knee chains. She gagged me again. “Go fetch me some nice lunch and wine. And hurry up, you bitch.”

I unloaded the car and quickly prepared sandwiches and wine. While I did that, she enjoyed viewing the terrace. I had to clean the inside of the cottage because no one had been there for a couple of months. It took almost two hours, and my feet were hurting quite badly since these particular shoes are slightly smaller than what I need. She came to check and was pleased. So my gag was released, and I was allowed to eat and drink. Actually, she made me drink about a liter of wine mixed with water; she wanted to fill me up. I went under the table, covered by a large cloth so no one could see me, and serviced her with my mouth. It took some time. My back hurt as well as my tongue. I heard her talking to someone, so I paused briefly, but she pushed my face against her, forcing me to continue while she chatted with strangers. I felt excited and humiliated like never before. “Come up now. I want you to prepare more food and bring more wine. After that, you will have a shower; I can smell you from here. Don’t forget to do an enema. Then get dressed in your favorites and come back. When you return, finish yourself off.”

I did as she said. I performed the enema and showered properly. Then I glued my breasts again and masked them with makeup. I put the dildo back in. I took black thong panties, a black bra, panty-stockings, a fishtail skirt that falls just under the knees and slightly restricts my steps, a long-sleeved black top with a nice cut, and closed-toe ankle shoes with open toes. They are 13cm high heels with a 3cm platform; very comfortable. I did my makeup and finalized the look in front of Dana. I was allowed to sit with her while we talked. I loved the feeling. I loved the collar and all the silver jewelry. The sensation of wearing these clothes…

“Chiding me. The feeling of the heels shaping my feet. We talked and drank for some time like two girlfriends. Even when somebody passed by we just waved and giggled. I did not talk but evidently that man recognized nothing. When the darkness started to fall Dana decided to take me for a trip. Still dressed how i was we jumped into the car and drove couple miles. We walked a bit into a forest and hit an old railroad. ‘So I will get you ready and you will walk that way for about 5km. You have one hour for that. You need to walk on the railroad, not next to it. It was raining so believe me i will see the difference on your shoes. For each minute you are late you get punishment. If you walk next instead of in the middle of the railroad you will have to eat the dirt from your shoes. Now put these on.’ I had to put great 14cm knee high black boots without platform, the ones i can hardly walk at all. They have great red sole and metal heel. I love them. The she dressed me in overbust corset and made it as tight as she could. Straight away i felt how i cant breathe properly. After corset she removed the collar i had and put strict one on. O could not move my head from side to side or in front or back, nothing. To the collar 6cm ball gag was attached. She did not gave me any cuffs on my legs. She gave me cuffs on wrists and elbows and locked it all together with one chain. Once i unlock the lock with the key i find in the 5km dedicated place it will release my albows as well. It was tight, the whole situation. Me alone on the unused railway track. Dressed as a woman. In unbelievable high heels. Bound. Gagged… 5km.. She left me. I started my trip. I tripped couple of times and nearly felt over. I could catch my breath. After while i had to stop. I was trying to think. Than i tried a different approach. I was catwalking, trying to do exactly same steps and same tempo so i would always hit the plank and not the small rocks in between. I was sweating a lot and couldnt breathe properly. My spit was all over my clothes. After a while i got into it and was enjoying my walk. I even wanted to shout look how great i am. The unbelievable heels did not seem that bad any more after the whole day practise in lover shoes. I was doing quite well. But when i tried to be faster i lost it completely, nearly fall over again, And had to start again. It was a big fight. I finally saw the light next to the crossing. I went to the lamp i found the key. I released my hands. I found a letter as well. ‘Now you will go to the pub and knock on the window to the left. I have the key from your gag, dont look for it. If anyone finds you you are in double trouble, from me and possibly from him, haha.’ Great. I had to sneak to the pub and be very careful. When i was nearly there i heard the door open so i hid behind the car. My heart was jumping and that corset was pressing into me. I almost lost conciesness. When the two guys left i slowly went to that window and knocked, And waited. My mistress came out: ‘You are twelve minutes late. Get into the car, And remember twelve minutes.’ When we got back I had to change again. This time into my party clothes. I started with garters belt and tights with nice flowers on them. Then i put sexy panties and bra above that Sequin minidress with sleeves and around the neck. And the same 14cm boots i had for the walk. I was not allowed to wear anything else. Dana tied my elbows very tight and secured the rope around my shoulders. She was just watching me for a while, standing upright. My feet were very tired after the whole day. She lied on the bed and ordered me to do it to her with my mouth again. After that she took me upstairs to the attic. It was big room there with wooden beams uncovered. She tied my wrists behind my back and used the beam to secure my hands up, I had to bend over a bit. Then she took camera and made some pictures. She showed me the video from my walk. I was like in a dream, looked like i made a light bondage porn. She was laughing at me and I was feeling embarrased again. When she had enough of enjoying my misery she blindfolded me. I felt how she connected the pump to my panties and inflated the dildo inside me quite a bit. She left me like that. I could move on my feet because she did not bind them, but i tried to get myself free however the ropes did their job and I could not release myself. ‘Where did you go, Release me, Dont leave me like that.’ Nothing. I waited. It seemed to be long time. Suddenly she came. She pulled my skirt up and panties down. I felt hot wax on my ass. She continued with the wax on any part of my body that was not covered. It was hot but nicely hot, I was enjoying that. When she got bored she spilt the rest on my ass And that hurt much worse. It did not get cool so quick and I screamed a little. ‘Did it hurt? Thats good sissy slut. We are just getting started.’ She laughed again. I could not see anything and i did not hear her, From nowhere the cane came. ‘Ouch’ More from surprise than pain. She was giving me caning on my ass, back, legs, everywhere she wanted. Few of them aimed between my legs. It was becoming more painful and i started to breathe heavily. When my ass got red she stopped. ‘Open your mouth now.’ I did it. Princess said ‘Lick that cock,’ So i did. It was familiar 8inch quite wide but very soft dildo. ‘Suck it.’ I was sucking it like the best bitch on the world, But she was no happy. When she stopped i was glad but i did not know what is coming. She gave me wide collar and secured it to the beam at the top and to the hook on the floor, I could not move my head much. ‘Open.’ So you always wanted to facefuck me? I got scared. And she went into my mouth. ‘Wider’ i had to open my mouth and i felt the dildo coming down my neck. My eyes went wet, I didnt cry but it went automatically when the dildo reached my throat. She was fucking my mouth, It hurt but amazing at same time. I felt it coming in and out. Could not resist it. Almost vomited couple of times. She always stopped right before that and let me spit out. It was long and my throat hurting after a while And then she came. I felt the sperm coming in my mouth ‘Dont waste a single drop, Do you know for how long i was gathering it?’ She continued to squirt until i had my mouth full. ‘Swallow bitch.’ I was feeling sick. The taste not good. Swallowed and almost threw up, Made it through worst eventually. Came all over face Put blindfold away did on eyes in hair nose covered whole face. ‘Hope you liked it. I did What do say?’ ‘Thank you Princess.’ She took latex hood And covered wet face with it Felt cum more intense Disgusting For while preparing something Smelling own cum Feeling everywhere When ready gave some whips Took inflatable gag Inserted in mouth Secured straps over head Blindfolded by hood Added leather blindfold ‘So now for punishment Twelve minutes strict bondage.’ Tied legs knees ankles Pulled rope wrists higher Secured elbows beam Changed rope collar secured ropes around knees Deeply bend forward Could not move at all Gave clips balls dick Felt through latex Lost senses balance Ropes holding place Inflated gag dildo Never experienced something like that Not even close So now enjoy punishment whore Started dildo Left Vibrations strong filling pretty much Inside whole body Hand getting itchy lack blood Feeling sperm nose mouth mix rubber helpless Completel

I was overwhelmed by the intensity of it all. Eventually, I gave in even though it felt different from my usual experience. My penis failed to stiffen properly and the semen remained trapped within me. The sensation was so powerful that screaming seemed like a natural reaction. Breathing became difficult as waves of pure pleasure washed over me for a while before the vibrations finally ceased. She unfastened the clamps, removed both the dildo and my gag, then untied the ropes securing me to the beam, causing me to slump toward the floor. My sense of balance deserted me momentarily. After freeing up the rest of her restraints, she spent some time stroking me affectionately before sending me off for a shower once I could stand upright again. END of day one. I’ll share more details if you’re curious.