Sorry for the wait, this is a bit of a lengthy read.
I had been looking forward to this weekend for a long time, her housemate was away, she had been torturing me with texts with what she was going to do when she got hold of me and of course the odd teasing picture of her. I got home and threw some stuff in the bag, got a nice relaxing shower. I just got out of the shower when I got a text from her asking for me to shave my pubes off, making sure my balls were smooth as well. It seemed strange, but I put it down to her complaining about pubes in her teeth when she was giving me a blowjob. So I went back and shaved my cock and balls, not sure why but I did my bum hole as well.
I drove over there luckily without too many issues, i stopped off to pick up some of her favourite flowers, a nice bottle of wine and to finish the night off a bottle of jim beams. When I pulled up outside Her place, I got a text from her. I was a bit curious as it said, ‘things will be different this weekend, if you agree come on in!’. I was a bit concerned about what could be different, I was shitting myself as I walked up the path to her front door., as I had no idea what she was up to. I entered her place, the hallway empty, no sounds could be heard in the flat, I could smell her perfume so I knew she was still there. I shouted hello sweetie how are you doing?, i got no reply from her. I did hear heels moving on the wooden floor of the front room, I relaxed a lot as I knew i was not alone in there. She came out of the front room dressed very sexy black thigh boots, skimpy black knickers, black fishnet stockings and a black basque. My jaw hit the floor , when I saw her, she looked amazing, she noticed my cock making a tent in front of my trousers as well, she smiled as she saw that, but that quickly stopped, as soon as it appeared.
I went to move towards her to hug and kiss her, as she had certainly turned me on. She said ‘stop!, in a voice that was quite strict, froze to the spot, the smile fleetingly appeared on her face again. She was enjoying the power she seemed to have over me, i felt like a naughty kid being shouted at by my mum. She went on to tell me what was going to happen this weekend. She told me that she felt I used her just for sex, I had no idea what she went through when ever we were together, so this weekend she was going to show me what she went through. This sounded quite easy, as she doesn’t need to do too much when I am with her, I look after her, we have good sex.
She suggested I have a shower to freshen up after the drive over, I thought I would play along, she asked me to use the body wash she god for me. It was definitely something I would never use, as it smelt flowery, but I played along with her request. It felt different as I was using it, it burned a bit on my balls and cock, she said it would do that and stop being a baby. Only as I was drying myself did I realise it wasn’t normal body wash, it was a hair remover, my chest, legs, and arms were now bald. My cock and balls were bald as well, they felt different without any hair there. I went into the bedroom in a bit of a mood, as she should have told me what it was, she replied that she was always smooth for me and I obviously liked her that way. I agreed with her that I did enjoy her pussy being shaved, she reminded me that I was to experience what she goes through when she is with me. I got dressed in a bit of a huff, as I had stupidly agreed to this. What next as she got planned for me.
We went out for a nice meal, I was on my best behaviour with her in case it helped me a little with her. She got a very tipsy on the wine and fell asleep when we got home, needless to say I didn’t get chance to fuck her that night, it peeved me a little as I was still horny from seeing her in the basque earlier on. In the morning I still had no idea what she has planned, she breakfast in bed was on the cards. After we had breakfast, I tried my luck with her, she had other plans for me. She got up and took a case out of the wardrobe, put it on the bed and told me to open it. I opened it gingerly not knowing what was inside, there was a few dresses, lingerie, heels, wigs and god knows what else what lurking in the case. She could see I ha d a puzzled look on my face, what did this have to do with experiencing what she goes thr..... OH SHIT!, the penny had dropped. She expected me to wear dresses, bra, heels, etc., in other words to become a woman. She laughed as she saw me realise what she had in mind me for me. I was furious at the thought putting a dress on, wearing women’s clothes. She sat there laughing at me, she told me that she offered me a choice, I should not have agreed to this. She told me to choose a pair of knickers to wear, I went to tell her to fuck off, she laughed and reminded me I had greed to it. She added that if I didn’t like it I could leave, but we were over!. Fuck, I didn’t see that coming. I grabbed the first pair of knickers I saw, as I stepped in to them, I noticed they were a lacy pair of knickers. Pink in colour, they felt different to my undies, they cupped my balls, clung to my arse cheeks, they felt good on, the lace was a new sensation against my cock as well . She told me to put the bra on next, i am sure I heard her chuckle as I struggled to put it on, as I had only ever took them off women, never bothered to see how they put them on. After a good 10 minutes struggling to fasten the clips behind me, I had the bra on. I was told to put the breastform in, that felt weird, they looked like boobs, i put them in my bra, oh my god they were cold on my chest. I looked at her for guidance, she was fully dressed, how did she manage that. I was told to put on the suspender belt and stockings, i did like the feel of those on my legs,. They were quite sheer in the thickness, she had chosen a black colour for me, they had a nice black lace band at the top, i could feel myself get aroused as I slid them up my legs. It took me ages to get the clips on the stockings, hopefully that became easier as you did it more often, hopefully I wouldn’t need to wear these too many times. I was handed a dress to wear, this was different , as I had no idea what to expect. The dress was a short sleeved dress the neckline wasn’t too low and that was mid thigh in length, purple , thank god as I certainly did not want to show off the tops of those stockings. I was told to sit at the dressing table, so she could do my make up, I was not looking forward to this, as it felt wrong to be wearing make up. Once she had finished, she put on a shoulder length blonde wig,. She told me to look at myself in the mirror, my god I was a woman, I looked very convincing, i had purple eyeshadow on, pale pink lipstick. I would be ok, as long as we didn’t leave the house, surely she isn’t that cruel.
We went downstairs to make breakfast, throughout the morning she was telling me not to do things, such as crouch down with my legs open, she told me to look down, as I had a bit of a puzzled look on my face. Anyone looking would definitely see my cock in my knickers, shame there was so many perverts about that look up women’s skirts, just like I do often. Once we had eaten breakfast and cleaned up, she told me that we were off out for a bit of shopping. I tried to protest about going out dressed as a woman, but she just gave me a pair of shoes to put on, a handbag and coat and opened the door for me. The shoes were not too bad, they were a closed toe type shoe, the heel was only a couple of inches high, so they were quite easy to walk in. As I was walking down the garden path she was telling me how to walk, less like a docker and more like a woman.
I found it hard to get into the car without flashing my knickers, it was something I didn’t have to think about usually. But getting this bit right would help me immensely, as I didn’t want to flash my knickers, or have some sharp eyed person notice that I had a little something extra down there than the average woman. The journey to the shops was quite uneventful, thank god, I will say it was strange having men leer at me though, it made me feel a little uncomfortable. Once the car was parked, I had to figure out how to get out without flashing my knickers again. This was a bit more important as there were families, women and of course men. So the reaction could be anything from outrage, to lust. We went to a local coffee shop so she could tell me what we were in here for, I am sure it was just so she could prolong me being out dressed as a woman, I was nervous of being found out, as I knew it could end badly for me. She was in to get some nee clothes for her, seeing as she liked how good I looked she wanted me to get some more dresses as well, hearing this I was about to explode at her, then I realised two things, I might have to walk home, the other was I was dressed as a woman. She laughed when she saw the realisation appear on my face, she was enjoying this immensely. As I couldn’t protest too much, as I needed her to get home, as I would never pass for a woman all the way home.
Finishing our coffees we left the cafe and I was about to enter the world of women’s clothes shopping. First stop was a dress shop I was told to look at a going out dress, it had to be sexy. She went off to talk to the shop assistant while I was looking at a sexy short black dress, that would cling to my girlfriends sexy body. I chose a few different dresses for her, by the time she arrived at my side again. she guided me towards the back of the shop, to a private dressing room, thank god I wouldn’t have to change in front of another woman, that would have been a really bad experience. When she opened the door there was a full length mirror on one wall, a rail with several dresses, trousers, skirts on it, I didn’t pay much attention to them at first. I gave the dresses to my girlfriend that I had chosen for her, she dismissed them slightly and turned her attention to the clothes rail. She told me to get out of my clothes but leave the lingerie on, I waited a second or two for the shop assistant to leave, my girlfriend laughed and told me that she was here to help me dress, she knew about my visit in advance and agreed to help. This did not sit very well with me at all, dressing in women’s clothes in front of my girlfriend was one thing, but letting others know was a total different thing. She must have seen an annoyed look flash across my face, she quite sternly reminded me that I agreed to this, if I didn’t like it she would leave me to find my own way home. As I heard those words I slowly started to undress, it didn’t take me long to end up just in my bra, knickers, suspender belt and stockings, the shop assistant complimented her on her choice of lingerie that she had picked for me. I blushed as she said those words, it didn’t help that she was admiring my knickers as well, god! Lets hope I don’t get a hard on, that would be embarrassing and also impossible to hide. I tried on a black dress, well what little of that was there, it finished an inch or two below my bum cheeks, there was no way I could hide the suspender belt and stockings in this one, the women stood next to each other asking me to turn round one way, then another as they looked at the fit of the dress. I took that one off and was given a dress with a tight body but loose skirt, I liked this one as it was a bit longer, I didn’t like the way the skirt flew up as I walked. Dress after dress was tried on, the pair of them didn’t spare any criticism either, mostly about how I held myself, how I should have my shoulders back, my arms were not right, they could see my cock sticking out, etc.
I must have tried on at least 10 dresses, it was strange to see the different types of dresses. Some where figure hugging, they looked so sexy as they clung to my false boobs and my arse. Others had a flared skirt, that lifted as I walked. I tried on tops, skirts, blouses, leggings and jeans. It was bloody exhausting shopping as a woman, I like just going on to town, getting what I want, getting a coffee and then going home. After what seemed like half a day spent trying on clothes, I perfected putting on and taking off dresses, also got a few tips on walling in heels. We finally left the shop with two armfuls of bags. She then dragged me to the cosmetics floor of a department store, she got a few more bits of make up for me. I was so embarrassed being in that department, as she put different colours of make up on me, I was still expecting someone to cotton on that I was a man, wearing a dress, bra and heels.
She finally brought our shopping spree to an end, thank god, my feet were killing me, the bra straps were digging into my shoulders, I just want to get home, get out of these silly clothes and get into more comfortable clothes. Judging by the boot full of clothes that had been bought, that would not be the case. Driving home she mentioned that she had a sexy surprise booked for tonight, finally I thought iI would get the chance to fuck her brains out. We got a Chinese take away on the way home, showing her cruel side, she made me go in and order it. I was trying to ask for the food, in a female voice. We got home and enjoyed the food, she then told me to go up and take a bath, so she can get things ready for her surprise. While I was running a bath, I started to undress, I slipped off the dress, admiring myself in my lingerie. The bra holding my false boobs in place, they looked and felt so realistic, shame I didn’t get the same pleasure that women get from feeling them. I love the look of stockings and suspenders on a woman, but they felt so sexy against my skin. I remember being told to roll the stockings down my legs when removing them, not sure why but if taking them off by rolling gets me closer to fucking her, then roll them down it is. I enjoyed getting into the bath, not sure I cared for the scented bubble bath, however I did enjoy the feelling of warm water on my smooth body, it felt different though.
I finished my bath, got dried, I put on a cream that was left on the side for me, not sure what it was, but it smelt nice. There was a black basque and black stocking left out for me, not sure she never left any knickers out to me, what game was she playing on me now. I called out to her once I had the basque and stockings on, I still can’t get the hang of those bloody clips, hopefully I won’t need to wear them anymore. She came in wearing a silk robe that came halfway down her thighs, she looked ever so sexy, I felt my cock twitch at the thought of fucking her later, she obviously knew what was on my mind, as she playfully said’ not yet sweetie, I still need my fun’. Whoa! Fun, that brought my back down to earth with a bump, I thought she was having her fun by having me wear women’s clothes, going out sodding shopping, trying on hundreds of dresses, but No, she hasn’t had her fun yet. With that she pulled out an orb, with a stem and flat plug on the bottom, what or, where is that supposed to go. She told me to bend over, why? It is not meant to go there? Surely not! The next thing I felt was some cold and wet on my bum, also I felt something enter my bum, it was different, not uncomfortable, but not sure if I liked it. The finger was removed and a bigger object, was placed at the entrance to my bum, there was some force on it as it started to open my bum, this was starting to become uncomfortable, verging on being painful, Ow!, WTF was that, it was excruciating., I then herd her giggle, was this her having fun. Finally, the pain eased of, but my bum felt ever so full. She then give me a lacy thong to put on, not sure why but my cock was starting to get hard, the material of the thong wasn’t helping at all, the butt plug was rubbing on my prostrate as well.
She sat me down, which I did gingerly with the butt plug in. She put my make up on, she used a nice shade of red lipstick on, my eyeshadow was done perfectly as I like on her, a smoky eyeshadow look. I put on the dress that she chose for me, it was a sleeveless figure hugging dress, that barely covered my bum. The wig was shoulder length, dark red in colour, never thought I would of myself as a red head. I slipped on the heels and headed downstairs, while she got ready.
I had a bottle a nice bottle of wine out, half filled my glass , I was just looking forward to taking my first sip, as the door bell rung. Before I had chance to panic, I heard her shout down asking my to get the door. It dawned on me, when I was part way to the door, I was dressed as a woman. I opened the door eventually, standing in the doorway was a bloke. He was wearing a nice short sleeved shirt, blue jeans, nice pair of shoes, he was about 6 foot tall, dark short hair, green eyes, he had a body that looked liked he worked out a lot. He gave me a disarming smile, then asked could he cone in, as I was blocking the door in shock still not sure what to do. I stepped aside and let him in, he was carrying a nice bottle of wine and a bunch of flowers. Standing there like a bit of an idiot, after closing the door. He took a step closer to me and kissed me on the cheek, that snapped me out of my daydream state. I apologised to him, for acting like a numpty. He laughed and gave me the wine and flowers, saying not to worry. We went into the kitchen, to put the flowers in a vase, I felt his body behind me, he slid his arms around me, then kissed me on the side of my neck, my god, what was he doing to me, a simple kiss had me weak at the knees. Just then my girlfriend told him to stop that, before you both get carried away.
She introduced him as Stuart, she had been talking to him online, telling him what she had planned for tonight for me. I felt my heart sink, as she explained this whole weekend was planned, the end of the weekend was my being dressed as a woman, me being fucked like a woman, just like I had done to her several times. She told me that I would feel a man’s sperm in my arse. I must have looked totally sick, as she giggled, as she repeated the words, I will have done to me, what happens to her.. I looked at Stuart, I just couldn’t get my head round him sticking his cock in me, till he cums in me.
She opened the wine and poured it into the glasses on the worktop, she handed on me to Stuart, Then took the other two into the front room, she waited for Stuart to sit on the sofa, she put my glass down on the coffee table, then hinted I should sit next to him. I sat down next to him, he smiled and put his hand on my nylon clad knee, just lightly caressing a small area. After a bit of small talk by those two, I was part fuming, for letting this happen to me, part aroused at being in the sexy lingerie, dress, heels and make up. I hadn’t noticed his hand had slowly moved up my leg, it was half way up my thigh, I took another swig of my wine and thought I had better get this over with. I decided I would try and get into this, maybe she would get jealous and put a stop to it. I put my glass on the table, then turned towards him, leaning in I kissed him on his lips. I made it a slow sexy kiss, I knew she loved. I could feel myself react, my cock stirring in my knickers, I let my hand stroke his groin, I felt his cock reacting as well. He tried to move his hand higher up my leg, but I stopped him, I wanted to try to take control of this.
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