This is the second time I experienced being feminised. I remember it as a very sexual experience, despite no sexual contact taking place what so ever. It is probably because at the time I was fourteen, which lets be honest, is a time where almost anything seems sexual. I was about the same size I am now which is average height but very slim, and I hung around mostly with the 'alternative' group the same age. We were often called 'moshers' and 'goths'. This experience was between me and one of my close female friends Mel, at her house.
It was a Friday and me and a group of my friends were going to Mel's for a sort of party straight after school, although there were not that many of us going so I don't know if party is the right word. Mel lived with her mum, as her parents were divorced, and her mum was away for the whole weekend. I honestly can't remember why she was away for the weekend but she did leave Mel alone in the house quite often.
All of us who were going to Mel's were meant to be staying over until the Saturday and so I had told my parents I would be staying at one of my male friends house, as I did not think they would want me staying at a girls house at that age. But at about 10:30'ish that night everyone apart from myself had left. I know a couple of them were going to see one of their brothers band, but I'm not sure why the others had left. Possibly their parents hadn't fallen for the old trick mine had. But whatever the reason it left just me and Mel, alone, in her house, at fourteen.
Although me and Mel were close I had never really thought of her in 'that' way, because I knew one of my other friends had a major thing for her, but I must admit just me and her in the house after a couple of drinks (we'd got one our friends older brother to buy some vodka and beer) I think I was kind off hopeful. Mel was very pretty, long black hair big blue eyes, with a lot of eye make up which I liked, and she was slim but quite big chested. So for a fourteen year old boy it was easy to be attracted to her.
After we had been alone for a while (I'm not sure how long, sorry) we went upstairs to her room. And now my heart was definitely beating faster. Mel had told me she had bought a new corset and she wanted to show me it, again first thoughts of a fourteen year old boy at this suggestion are not that clean. Mel wore a lot of corsets as did a lot of the other girls I hung round with.
We went into her room and she had got her new corset out her drawer and held it up for me to see. Not what I had hoped for but really what I should of expected. I said that it was nice and that I liked it, which was true. At time I was becoming increasingly more interested with female clothing and had snuck into my sisters things a couple of times. We talked for a little bit about how she had wanted a different one but couldn't afford it and what she would wear this one with. I had made a couple of suggestions about outfits it could work with, not really thinking how it would sound, and Mel must of got the idea I was a bit to interested in her clothes. She suggested that I should try her new corset on, saying something like "You'd look good in a corset."
I was quite thrilled by the idea but didn't want Mel to think that so I said no and that it would be stupid, as she kept trying to convince me to put it on. And of course she convinced me, as I really did want to wear it. But I thought I would be wearing it the way her and the other girls wore their corsets, over something like a shirt or dress really as more of an accessory. So I thought I would just be putting it on over my t-shirt (we had all taken clothes with us so that we didn't have to stay in our school uniforms) which would of been good enough for me, but Mel told me I had to take my t-shirt off. I can't remember what she said to get me to take my shirt off but I know I was more than willing to do so.
Mel put the corset on me. The corset was red with black patterned lace over the red, and it tied at the front with black ribbon. She put it on me and tightened it fairly loosely at first but then she re-did it so that it was much tighter. I found it very arousing but really didn't want Mel to know that so said things like "it's way to tight," and "there's no way you'd wear it this tight." But she didn't loosen it, which I was happy about. She put some socks in the cups of the corset to make it look as though I had breasts, which made both me and Mel laugh. She kept saying I had the perfect figure for it and other little comments about how petite I was, in a sort of jokey way. I was really enjoying wearing it, but I didn't think it would last much longer. I was sure Mel was going to get bored and that we would end up doing something else.
But Mel, without any warning to me, suddenly unfastened the belt on my jeans making them drop to my ankles. I always wore very baggy clothing so when the belt got unfastened my jeans just dropped. This shocked me and my instant reaction was to try and pull my jeans back up, but Mel stopped me saying that she wanted me to take them off. Again I stress that I was fourteen, so when a pretty girl told me to take my jeans off, I did so. So I was stood in the middle of Mel's bedroom wearing nothing but my boxer shorts, my socks and her red and black corset. I was also trying very hard to fight getting an erection.
Mel thought that me stood in her room dressed like I was, was pretty funny. She said something about wanting to have my legs. She also told me that the socks looked stupid and that I should take them off as well, which I did in an ever so ungraceful way, almost falling over about ten times. She then went over to her chest of drawers again and started looking through one of the drawers. She was literally umming and arring whilst she was looking through it. She then turned round to me holding a pair of black lace panties, which she said would look 'perfect'. I was now really trying hard not to get an erection and at the same time trying to seem as though I didn't want to wear her panties, which was an incredibly difficult thing to do.
Of course I did allow her to 'convince' me that I should put them on. I went to take the knickers off her sand said I'd go to the bathroom to put them on. But Mel wasn't having it and she kept hold of the panties and sat down on her bed. She then told me I had to put them on in front of her and to take my boxers off. I had never been naked in front of a girl, or anyone, before so I was very nervous about this. I mean I was also incredibly excited thinking that maybe it might lead to something, but mostly I was nervous. However, I did remove my boxer shorts and throw them to the side of where I was stood. I cupped my penis and testicles with my hand so Mel couldn't see them, but again Mel wasn't having it and made me move my hand. I had been able not to get an erection, but I was definitely half way there when I moved my hand for Mel to see.
Mel's reaction to my penis was many boys worst nightmare, she laughed. Not hysterically or anything, it was probably more of chuckle to be honest, but it was definitely a laugh. This to me was actually very arousing, I had never thought about someone laughing at my penis as sexy before, but I did find Mel laughing at it very sexy. I knew she was laughing at the size, and after that night was over and I was able to think about it, I did get worried she would tell everyone I had a small penis. And I'm pretty sure she did as I often noticed the girls I hung round with whispering and laughing, seemingly at me, after this weekend was over.
However after she had briefly laughed at it she then handed me the panties and said something about not having to worry about me stretching them or something, I honestly can't remember, but I do remember that as soon as I had pulled the panties on I was instantly unable to stop myself getting an erection. Which embarrassed me, but at the same time I was with a girl wearing her panties and corset with an erection, and that felt pretty immense. Mel laughed at my erection but also tried to make me feel less uneasy about it, saying it was ok and that it was "cute". She also told me not to worry because I wasn't going to be "on display" for long.
She went to her wardrobe and opened the door on it which had a mirror so that I only got a passing glimpse of how I looked, which was pretty exposed. She went through the rail of clothes she had in there until she pulled out a black gothic dress. It had a black sort off mesh tutu and the top off it was black with black lace all over it and covered the entire top of the body with a high neckline and long sleeves.  Mel helped pull the dress over my head and down, which was probably the closest thing to something sexual, that happened that night. As when she had pulled it down she had brushed up against my erection very briefly. Which did make me squirm a bit (in a good way). When the dress was on Mel closed the door on her wardrobe and told me to look at "how good you look" in the mirror on it.
 I had seen Mel wear this dress before and she had looked good in it, and it hadn't been particularly short on her. But Mel was not as tall as I was, I mean she wasn't short and as I've said I'm not tall, but when I put that dress on it was VERY short. As in so short  I'm sure every time I bent over the panties I was wearing were clearly on show. Honestly looking at myself in that mirror, dressed like I was with Mel stood next to me smiling  was the most sexually excited I think I ever was during my teenage years. Certainly my erection didn't go until hours later when we decided to go to sleep. We stayed up until the early hours of the Saturday morning watching A Nightmare Before Christmas (even though it was spring) and I stayed dressed as I was for the whole night. It was just like I was wearing my own clothes except these clothes made me incredibly horny, but we didn't do anything more with it. I slept in the outfit on Mel's sofa bed. In the morning I woke up just after Mel and when I picked up my clothes off her floor we shared a little awkward smile, but that was it. I got changed gave her clothes back, which again was very awkward but neither of us really said anything about it. Then I left and went home.
On the Monday morning at school it was totally back to normal, like nothing had happened. As I mentioned I noticed some of my other female friends whispering and laughing. Which did put me on edge a bit. But other than that there was no difference from before that night. I'm not entirely sure I was happy about how it turned out at the time, but looking back I think it worked out pretty damn well for me.
I hope you enjoyed this true story off my second experience of feminization. As I said in my first experience post, please feel free to comment your own experiences. They may help inspire some of my captions and I'm sure others will enjoy reading them too.

Lots of Love

xxx

P.S. - Mel is not the real name of the girl involved.

This one shouldn't, and doesn't, really count as a 'feminization' experience, but it is an experience I consider to be of great significance to me. So I hope you can enjoy it anyway.

I was sixteen when this experience took place. As I believe I have mentioned, I had snuck into my sisters things a few times before my second experience. But since that experience, which I found to be so arousing, I had been cross dressing in my sisters things more and more (pretty much when ever I had the opportunity.)
I have three older sisters, who with the help off another girl gave me my first feminization experience. The sister who's things I always used was the middle ones, who for the sake of this, will be called Amy from now on. There were a couple off reasons why I always wore her stuff, the first being she is closer to my size. I mean she is shorter but like me she is very slim, not that my other two sisters are fat or anything. Not by any means in fact, but they are even shorter than Amy and slightly broader. So basically Amy's clothes fit me reasonably well, not perfectly, but well enough. The second and most important reason I had for wearing her clothes though, was that she always had the best stuff. Again my  other sisters didn't dress badly or anything, but Amy was properly into fashion. She always read Vogue and watched those what to wear programmes on TV. So she always seemed to have new things, and they were always great.
As I said at this point in my life I would try on her things any chance I had. And I thought I had been given the golden opportunity to spend a good long time trying on her stuff when this experience took place. My eldest sister had moved out a year or so earlier, not far, but a fair drive from where we were. And the youngest of my three sisters had gone to university in a different city altogether, so of course was no longer at home. So it was just me, Amy and my parents. My parents who were going to spend five days away for a wedding, leaving on the Friday morning. Which meant it was just me an Amy, and I knew that on the Saturday Amy was going out. Amy worked as a waitress at the time and this was her first weekend off in a while, so she had planned to meet up with Becky, a friend she hadn't had chance to see for some time. A drop dead gorgeous friend as well, but that's besides the point. The point is I knew I would have the whole house to my self for pretty much the whole day Saturday. So as Saturday got closer and closer I of course got more and more excited. And on the Friday night it is no exaggeration to say I was like a child at Christmas, barely able to get any sleep at all.
On Saturday morning I was up nice and early, and was fidgeting and unable to stay still, as I waited for Amy to leave. She didn't leave until about 10:30ish probably later, and as she left she told me that I would probably have to sort my own dinner as she may still be out. I tried to play it off cool, like it was no big deal, but I was mega excited that meant I would have even longer to wear her things. What could possibly be better!
As ever after she left, and I knew I was in the house alone, I waited for a bit before I went to her room. This was because I was always paranoid someone would have forgotten something and catch me as they came back to retrieve it. Although this time I was so excited I'm sure my normal ten to fifteen minute wait was actually more like two or three minutes, but I remember it felt like a long time.
Amy's room was always a mess, there was always dirty laundry on the floor, the bed was never made and she always had glasses that she'd had drinks in all over the place. For someone who took as much pride in her appearance it really was bad, but it was good for me. Because I never had to worry if I put something back in the wrong place as she would never of known.
The first thing I did upon entering was strip completely naked, I always put my clothes on the bed as although it was never made, there was never any off her stuff left on it which made it easier to make sure I got all of my stuff back and didn't leave anything by accident. Amy had a full length mirror in her room, leaning against the wall next to her chest of drawers. I used to like to look at myself in the mirror as I went through the process off putting on her things, and the first process of that was me naked. So as ever, I looked at my naked self in the mirror, did some silly things like poses and trying to took my penis between my legs and such. I don't know why but I loved the mirror part of it, seeing myself going from naked boy to boy fully cross-dressed and all the stages in between.
After I was done messing around in the mirror I went straight to Amy's underwear draw. I rummaged through it for a good while trying to decide on a pair of panties to wear. I had worn most of them before and so I was ideally looking for a new pair, but they must of been dirty and I didn't like wearing my sisters stuff if it was dirty. So I decided on a pair of white lace panties with a cute little white bow at the front. I'd worn them before so I had seen them in the mirror before, but that however, did not stop me doing the same as before. Standing in front of the mirror, turning round to try and see my bum in them, striking feminine poses and pulling ridiculous faces.
Once again after the mirror I went back to her chest of drawers and started looking for a bra. I knew there was a bra that matched the panties I was wearing and so that was what I was searching for. It took me a while, and a lot of distractions from other pretty bras, but I did find the one I was looking for. I put it on, and stepped straight in front of the mirror again. I straightened out the straps making sure they were not twisted and I put the socks I had worn, that were on the bed, in each cup so that they looked filled. My sister did not have a very large cup size so I could use one sock per cup as long as I balled it up a certain way. Once that was done I did the same as before in the mirror, except this time most of the poses were based around the chest, pushing the cups together and things like that.
Then it was back to the chest of drawers again to find some tights. I loved wearing tights, I'm not sure why but I didn't feel I was fully cross-dressed without tights. The issue with that though, was that there wasn't a pair of Amy's tights I hadn't worn. But there was a favourite pair. Which I found pretty quickly. They were black sheer tights with a roses pattern going up the side of each leg in black again. They were amazing. They fit me brilliantly, they looked great and they felt insanely good. Despite how excited I always was by these tights, I was always really careful putting them on. Sitting on the edge of the bed and very slowly easing them up my legs until they were up. The last thing I wanted to do was ladder them, not just because they were so beautiful, but because I was sure my sister would notice. After they were on I really enjoyed looking in the mirror. Although the panties were covered you could still see them through the sheer tights, but you could no longer notice the bulge where my penis was. Which I always found very exciting, and so the posing and pouting (and even a bit of dancing *cringe*) were even more fun for me.
This time when I'd finished messing around in front of the mirror I headed to the wardrobe. I had no idea what it was I was hoping to put on, and to be honest I thought I'd probably try on more than a few things. But as I was sliding through the rail in her wardrobe looking at different tops, jeans, skirts, and dresses saying to myself 'worn that and that and that' I found a new dress. One that still had its label in it, which wasn't unusual for Amy as she bought so many new clothes when she put them away I think she often forgot about most of them. I still believe now that there are clothes she bought when she was at my parents house, that only I wore. Anyway, this dress still had it's label in, and I definitely hadn't worn it before.
The dress was a small black number, with the breast area upwards covered in black sequins. It was gorgeous, and there was no way I wasn't going to try it on. So straight away I took it off its hanger an unzipped the back. Then I bent down and stepped into it, pulling it up and struggling to get my arms in as it was so tight. As I have said Amy is shorter than me, so of course her clothes were often snug on me, but this was properly short and tight. I remember thinking that maybe that it must of been to small on Amy. But it did feel really good and I was determined to wear it. So I struggled for ages trying to get the zip, zipped up. Eventually when I did, the bottom of the dress just shot up my waist another inch or two and every time I pulled it back down it went straight back up. I stepped on my tiptoes (because my feet were too big too wear her heels) to in front of the mirror. I was incredibly happy with how the dress looked on. I mean it was ridiculously short and tight. So short that standing up straight meant that I could see the bottom of the panties I was wearing through the tights and so tight that at least an inch off bra was clearly visible. And the bra straps were digging into me quite firmly. But I loved it and I started to really go for it in the mirror. Pouting, blowing kisses, bending over and looking back over my shoulder like I was surprised to see my panties, just all sorts of stuff that I really enjoyed doing and that I was particularly enjoying at that time.
Unfortunately during my fun was when I heard the front door open and close. My heart sunk to the floor, I was terrified. I could hear my sister talking with Becky, and I could tell that they had gone into the kitchen or living room. I was so scared that I started to panic and frantically started trying to get the dress off. But the dress was so tight it had got stuck. Now I was really scared, I could still hear my sister and Becky talking downstairs and I was still trying insanely hard to get the dress off. But the zip wouldn't budge. So I decided in my mad panic to just pull it down off me. But this wasn't easy either as I really struggled to get my arms out of the dress, and when I finally managed that the dress was so tight I could barely move it. Thankfully I did manage to get it down past my waist and to my ankles so I could step out of it, but it had taken what felt like a lifetime to do so. So now I was sure my sister and Becky were going to come upstairs soon, which made me decide not to bother putting the dress back in the wardrobe and instead I just kicked it under the bed.
That's when the talking seemed to get louder, and I was sure they were coming up the stairs. I unhooked the bra quick and made sure to catch my socks as it came off. I left the bra just on the floor where it landed, it was on top off some of her dirty clothes I'm sure, but it was probably still noticeable. I was so scared at this point and I knew now for definite that they were on the stairs as I had heard one the stairs creek. I just grabbed all my clothes of Amy's bed and ran as quick as I could out off her room across the hall into my room, still wearing her panties and tights. I had no idea if they had seen me or if they were even up stairs yet but I was shaking with fear in my room as I put my socks over the tight and then threw my jogging pants and jumper on as well. I chucked my boxers into the corner of my room hoping they would be out of sight if Amy and Becky came into my room. Then I jumped on my bed and picked up my book and pretended to read it as I listened to hear what my sister and Becky were doing.
Even though I had been listening, I still almost leapt out of my skin when I heard a loud knock on my bedroom door. My sister and Becky walked straight in without waiting for my response to the knock. I tried really hard to seem relaxed but I was terrified that they had seen me run across the hall, or if they hadn't that one of them would notice I was still wearing tights and panties. But my sister just asked if I was okay, and said that her and Becky were heading back out to grab dinner and that she had just wanted to check on me. I had no idea what time it was but I had assumed it was in the evening as they were now home but I looked at my clock and saw it was only 3'o'clock. I responded to Amy saying I was fine and she said 'good' then went to go get something from her room leaving me and Becky.
I hadn't seen Becky in a good while as she was Amy's friend and Amy hadn't seen her either. But she was still stunning to look at and as bubbly and friendly as ever. As soon as Amy had left the room Becky had asked straight away how I was and what I'd been up to, which I liked and did calm me down a bit. But when my sister got back and said she was ready to go out again, Becky told me to get up and give her a hug. It was said in a nice friendly way but all my panic came back as I didn't want her or my sister to see I was wearing tights and panties. So I got up off my bed really carefully making sure my joggers were pulled up and my jumper was pulled down, and then quite tepidly walked over and whilst still slightly shaking from fear gave Becky a hug and a smile, said 'nice to see you again' and that was that. Her and my sister left and I listened to make sure they definitely did. After they'd gone I quickly took of the panties and tights went into my sisters room and put them back.
I spent the rest of that day really unsure about everything. If I heard the slightest little bump I got startled. It took me a good while to calm down. But when I did a few days later, when I'd seen my sister a fair bit and she had made no reference to it, I became really aroused. The idea of Becky catching me in women's clothes seriously turned me on, and still does.
As I said I know it isn't really a feminization experience, but I do sincerely hope you enjoyed it anyway. Please feel free to post your own experiences in the comments section for me and others to read and enjoy. I appreciate any comments from anyone and would like to say to everyone who has in the past or is going to comment in the future, a huge Thank You. :)

Lots of Love

xxx

P.S. - Amy and Becky are not the real names of those involved.

Okay, so this is unfortunately the last time I had any experience of being feminized. But it is, by far, the most exciting I have ever had and so hopefully you will enjoy reading about it as much as I enjoyed it. This experience happened a few years ago when I was 21, with my girlfriend at the time. Who for this will be called Ellie. And I remember this quite vividly as I have relived it in my mind a million times since.

Me and Ellie had been going out for about six or so months, and before this experience we had done different types of domination in the bedroom. Mostly spanking and some light bondage, as well as a fair bit of verbal humiliation, mostly about the size of my penis. We had also done some very minor feminization, I'd worn her panties and at one time lipstick. So I guess it was just natural progression that led to the experience I am going to write about. Especially as I enjoy being submissive (particularly being feminized) and Ellie very much enjoyed being dominant.
Ellie was very pretty. She was only about an inch shorter than me and was very slim like I am. Except she had beautiful curves, with gorgeous breasts and rear end. She was dark skinned with long dark hair, and huge brown eyes. Her lips were a major turn on, they were full but not overly thick and always seemed to be somehow teasing. She had a rose and a swan tattoo on the top left of her back, and honestly I was totally staggered by her beauty all off the time.
This experience is very personal and I found it the most sexually pleasurable experience of my life. We had both taken a week of work to spend some time together as our jobs sometimes meant we only got to see each other a few hours a week. We decided I'd stay the week at her flat as she lived alone and I had, and still do have, a flatmate. The first couple of days we didn't even have sex. It was just nice to spend time together and we went to different places, ate out and watched a couple of films. But on the Wednesday it changed completely.
I woke up fairly late, as it was our week off, at about ten, later than Ellie had woken up. After breakfast I had a shower, Ellie had already had hers and was in her room doing her make up when I went into the bathroom. When I came back to her room in just my towel I was taken by surprise. She was wearing nothing but black lingerie and thigh high black leather boots, which the top of her fishnet stockings just poked out off being held up by her garter belt, and she stood at the foot of her bed holding a jockeys whip. I was instantly turned on.
"Drop the the towel, bitch!" she commanded me in a stern but very sexy way, like I had heard her do before but not quite as stern. I obeyed, slightly trembling with excitement as I did, letting the towel hit the floor and revealing my already erect penis. Her eyes lit up with delight and she let out a playful and teasing laugh as she saw it.
"Look at your tiny little cock, getting all over excited," she said mockingly, "we should probably put that away somewhere it feel more at home. Don't you think?" She was asking a question but I knew it was rhetorical. And I was so turned on at this point my main focus was trying not to cum before we had started.
She held the jockey whip down by her side and slowly bent down, looking at me the whole time she did so, and then she picked up a pair of white ruffle panties off the bed and gave me a hauntingly playful smile. I hadn't looked at the bed since I had come back to the room as I had been so entranced by Ellie, but when she lifted up the panties I saw that there was more on the bed including a bra and garter belt both in white. Now I was desperately close to ejaculating and was breathing heavily, trying to fight it. Ellie strutted over to me, still stood just through the doorway, and chuckled, mocking me as she came closer.
"You know, I bought these panties especially for you, as I know how much you enjoy being my little bitch." She spoke whilst at the same time circling me, rubbing the ruffled panties all over my body and face, "And these aren't all I bought for you either, I got you lots of pretty things. Because I have something very special planned." She was almost whispering this into my ear and I was seconds away from exploding. Then she pushed the panties into my hand and barked at me to put them on.
The sudden change in her tone from a seductive whisper to almost a yell, startled me and I was quick to pull the panties on not just because I wanted too but because I genuinely felt I had too. The panties felt amazing on and Ellie laughed at the small bulge in them from my erection.
"Good girl!" She praised sarcastically. Then used the jockey whip to examine my erection, telling me how small it was and that it looked at home in a pair of pretty panties. Unfortunately this playful humiliation and the contact from the jockey whip lifting and rubbing against my penis, caused me to be unable to prevent the inevitable. And I came sensationally, all over the inside of my panties. I groaned loudly as it happened and my whole body practically spasmed. It wasn't the first time this had happened to me with Ellie, but this time felt worse than any of the others. I don't know why but I thought she was just going to stop and that whatever she had planned was just not going to happen anymore. I was devastated.
"I-I'm so sorry Ellie, so so sorry..." I was basically pleading with her for forgiveness before she had even reacted.
"That's alright," she said in a calm and almost uninterested tone, "I'm just going to have to punish you."
My heart started pounding a hundred beats per second. Punish me? I thought. This was exciting and I almost became erect again.
"Get on your hands and knees. Now!" She growled at me and I dropped to the floor straight away. And straight away I felt a sharp and painful smack across my backside. I let out a cry off pain but I was definitely aroused by this as I started to become fully erect. Ellie continued to spank me with the jockey whip, very hard. Telling me off as she did. Calling me her bitch, and saying I needed to learn how to control my 'tiny cocks' urges. This punishment was a much higher level of domination than anything we had done before and lasted for at least ten minutes.
When it did stop my backside was incredibly sore. Ellie told me to stand up and as I did she pinched my bottom and laughed at how red it was, saying that should teach me my lesson. But I was still fully erect and was slightly worried I may cum again before we reached what ever Ellie had planned. Yet there seemed to be no stopping Ellie, who seemed to be on a mission to dominate me further and further.
She grabbed the garter belt off the bed and without saying anything fastened it really tight around my waist.
"You've got such a feminine body." She told me as she gave me a light smack on my sore bottom with her hand. She then took the bra off the bed and held it up against me with a slightly wicked smile on her face.
"Ok. Arms up." Her tone was more flirtatious now. She seemed to be having fun being in total control, more so than ever before. I of course did as I was told and she put the bra on me. She pulled me really close to her, so she was pressed right up against my erection as she fastened it at the back. When it was fastened she lingered in that position for a few seconds staring me in the eyes and the she flicked the bra strap and smirked as she turned away from me. As she started to walk away towards her dresser table, she looked back over her shoulder and signalled me to follow her with her finger.
I followed the few short steps, the whole time staring at her perfect arse. Until she turned and faced me, standing behind her chair.
"Sit." She said seriously but still with that flirtatiousness in her voice and smile. I sat down on the chair facing the large mirror on the dresser. Ellie pulled a carrier bag out of one of the drawers and emptied it on the dresser in front of me. It was all make up.
"I bought all of this for you too," she said "and now I'm going to make you look like the pretty little girl you are." She seemed to really be excited by this idea almost like she was just playing with me. I had never worn full make up before, just lipstick and a bit of eyeliner a couple of times. But this time I had the works. Ellie spent ages, almost two hours, putting it on me and making fun off me as she did. Everything from foundation, to lip gloss, to eye shadow and huge false eye lashes. I was able to see the transformation happening in the mirror, but when I looked at myself after it was finished I was still shocked by it. I looked like a doll. I had bright pink lips and the eye make up, which took the longest to be put on, was also bright pink but with a glittery shine and black eyeliner. The false eyelashes were surprisingly heavy on, and when ever I blinked it felt totally bizarre. I had a bit of blush on my cheeks and she had made my eyebrows look thinner and shaped without plucking them.
Ellie gave me a kiss on the cheek as I looked at the mirror in astonishment, and told me I was her girl. My erection and been up and down during the time Ellie was putting the make up on me, as the actual process wasn't sexy but her laughing and making fun of me had been. But when she called me her 'girl' whilst I was looking at myself as a girl, it made me very erect again. She then started running her finger through my hair, which was fairly short, and said that she needed to something with it. As my hair was quite short there wasn't much she could do with it, but she spent about half an hour making it tidy, pushing the fringe to one side and putting a pink hair band with a bow on in it. This did make my hair look more girlish, but I did look more like a boy wearing a lot of make up than I did a girl.
When Ellie was done, she stood me up and examined me making me turn around for her whilst she laughed and made comments on how pretty I was.
"You do look very pretty, but I think we should finish getting you dressed." She said it like she was actually talking to a little girl. I was once again very aroused. She picked up a small packet of the bed and sat me down on the edge. She opened the packet and took out one white stocking leaving the other one in the packet which she dropped on the floor next to my feet. She then crouched down, picked up one of my legs and started slowly sliding the stocking up. As her hands reached the top of my thigh I had to fight not blowing my load again, and I think she could tell. As she chuckled to herself as she fastened the first stocking to my garter belt. Then the same painstakingly erotic process with the other stocking making me gasp this time as I stopped myself from cumming. This clearly amused Ellie, and she smiled at me almost with delight in her eyes.
"Stay where you are, princess, I'm going to get you the rest of what I bought." She proclaimed as she went over to her wardrobe. "I think you'll really like these." She said as pulled out a large paper bag from the bottom of it. I had no idea what was in it but I was definitely excited. The rest of the day so far had been so incredible, I just knew it was going to get even better.
"But first, you're going to make us some lunch. Like a good little bitch." Ellie smiled cruelly at me. I hadn't thought about the time but I looked at the clock and it was almost two. I wasn't really sure how to react to what Ellie had told me to do, but I slowly stood up and asked her what she would like. She told me to make some sort of pasta and to bring it in to her when I'd done it. I was still uncertain of what was happening, wether it was a break from what we were doing or somehow part of it. But I went to the kitchen and drew the blinds as fast as I could so no one could see me through the window.
It didn't take long for me to do a pasta in sauce, about twenty minutes maybe, and as soon as it was done I plated it up and took it through to the bedroom with cutlery.
"There's a good girl." Ellie remarked as I came in, making me feel like it was still part of what we were doing. She was sat on the bed with her back resting against the headboard. I sat next to her as we ate, we didn't talk at all but Ellie gave me a few looks which made it kind of sexy. After she'd finished with hers she dumped her plate with the cutlery on it, on top of mine. Even though I still had a few mouthfuls left.
"Go wash them up." She sounded very strict. "Then brush your teeth." She then stood up and went out of the room to the bathroom. I washed the plates in the sink as quickly as possible and then dried them as I waited for Ellie to come out of the bathroom. When she did she smiled at me, and told me to be quick. As I walked into the bathroom she shouted to me from the bedroom.
"And open that blind when your done!"
She really wanted to make me squirm and it turned me on massively. I brushed my teeth and was sort of felt odd looking in the mirror at myself knowing it was me, but it not looking like I ever had before. On the way back to the bedroom I opened the kitchen blinds, trying to stand to the side of the window so no one could look in and see me. The thought of someone else seeing me like this was thrilling but did make me feel uncomfortable.
It wasn't until I got back in the bedroom when I got really excited again though. Remembering that there was something for me in that paper bag and having no idea what it was. Ellie could clearly tell I was excited and told me to calm down as she didn't want me having another incident. She picked the bag up of the floor and out it down on the dresser. Then she pulled out a pair of pastel pink platform heels, pushing something else back into the bag.
"These are for you." She said as she handed them to me. "Size nine, that's right isn't it?"
She knew it was. I couldn't believe she'd bought these for me. I'd never worn heels before as my feet were always to big to fit into my sisters. I put them on and they fit well. But I could barely stand up in them. I started wobbling and being unsteady but Ellie just laughed.
"Don't worry, I'm going to teach you to walk in them just like a real girl would."
She picked up her jockey whip again and came to stand next to me.
"Heel, toe. Heel, toe. Ok?"
"O-ok."
"Remember good girls sway there hips when they walk. Now let me see you do it."
I was nervous that if I got it wrong she would whip me again as my arse was still sore from before, yet at the same time I loved the idea. I stepped forward remembering heel, toe, and tried to sway my hips but I felt kind of stupid doing it. That's when the whip struck me on the back of my thighs making me fall.
"I told you to sway your hips, bitch!" She shouted at me, "Now get up and do it again!"
I struggled back to my feet and tried again this time swaying my hips more, but it still wasn't right and the whip hit the back of my thighs again. This happened several more times until Ellie felt I was doing it properly. I thought that would be that with the walking then, and I would be able to see else was in the bag.
But no. Ellie then pulled the chair from her dresser to the middle of the floor and sat on it.
"Now you walk like a little slut, I want you to dance like one." She said with a devious smile on her face. She was still holding the whip in her hands and I had no idea what she wanted me to do.
"Dance bitch!"
There wasn't any music on, but I started swaying slightly from side to side simply because I was totally submissive to anything Ellie wanted.
"Oh no, I want a lap dance you little slut!" She laughed. So I nervously got closer to her and started giving her a lap dance. It wasn't really a lap dance but it was the best I could do never having been a good dancer and also being in a totally surreal situation. It seemed to please Ellie though as when I was doing it she laughed hysterically and whipped me saying "Just like that bitch!" It was definitely humiliating, but I was very turned on and quickly got hard again. That just seemed to entertain Ellie even more and she verbally castrated me, calling me a perfect whore and telling me my cock was the smallest she'd ever seen. All the time I kept giving her an awkward lap dance and getting more and more aroused.
"Ok, ok. That's enough you little whore." She said eventually, "Time to show you what else I bought you." She stood up pushing me aside and went over to the paper bag on the dresser. She reached in it and pulled out a pink dress, holding it up for me to see. It was pastel pink like the shoes with a high neck and pleats at the bottom and a butterfly pattern embroidered into one side of it. It was honestly amazing, and also too much for me too handle. As at the mere sight of it I once again ejaculated into my ruffle panties. Just like before my whole body moved as I did and I let out a large groan. I was just as ashamed as before but this time I was actually surprised it hadn't happened earlier on.
"Are you joking? You pathetic little bitch!" Ellie sounded seriously angry and she threw the dress down on the table and picked up her whip of the chair. She grabbed me roughly, by the hair and threw me face down onto the bed placing her knee on my back.
"Sorry Ellie. Sorry!" I tried to appeal against any punishment despite the fact I actually wanted the punishment.
"Shut up you little bitch!" She demanded, pulling my head back by the hair as she smacked me hard with the whip, and then again and again. Each time seemed a little harder and she kept verbally punishing me at the same time. My arse was in agony and I cried out during it, but even I couldn't tell if it was in pain or pleasure.
Even when the punishment finished she stayed in this aggressive mood. Pulling me up from the bed by my panties giving me a pretty sever wedgie.
"Put your fucking dress on you slut!" She screamed at me as I stumbled towards the dresser still adjusting to wearing heels. I picked up the dress and started to struggle putting it on. The whole time Ellie just stared at me with intensity. I got the dress on but couldn't zip it up.
"Turn around!" Ellie ordered firmly, then zipping the dress up. "There! Now look at yourself!"
She pulled me by the hair to in front of the mirror. "Look at what a little slut you are! Ay, your my little bitch aren't you!?"
"Yes." I replied tentatively whilst staring at this sissified version of myself in the mirror.
"No, I want to hear you say that your my little bitch!"
"I-I'm your little bitch," I mumbled it.
"Louder bitch!"
"I'm your little bitch!" I virtually shouted it.
"Good." She said letting go of my hair and smacking me once more across the arse with the whip. It hadn't been that long since I'd last cum, and this punishment was because of the last time I had. Yet I found the whole thing so arousing I was already hard again, but Ellie was unable to see it as the dress covered it for me.
Ellie sat down on the foot of the bed and lay the whip down next to her. She started to take off her thigh high boots as she was telling me that I needed to prove what a little bitch I was and how much she owned me. I agreed with everything she said and knew what was coming as I had been made to kiss her feet before, which I enjoyed a lot.
When the boots were off she pulled her legs onto the bed and told me to lie down on the floor in front of her. I hadn't expected that but did as I was told. I lay down and looked up at the ceiling. Without any warning Ellie's feet still in fishnet stockings both pushed down on my face. She rubbed them up and down moving my head side to side. Telling me I was worthless and belonged under her feet. I was so turned on, but I my panties were practically stuck to me from the last two times I'd gotten over excited and acted as a helpful reminder to control myself. I stayed on the floor with her feet all over my face for a good while until Ellie decided she wanted me to prove myself more.
She took her feet off my face and told me to stand up. As I stood up she crawled across the bed to the headboard. She pulled down her panties revealing her incredible arse and put one hand on the headboard. With the other hand she signalled me to the bed.
"Come over here and kiss my ass!" She said it like she was trying to seduce me rather than ordering me to do it. But I knew it was an order and I think she knew I wanted to do it. I crawled onto the bed, behind her and kissed her arse on the cheek. She laughed and told me to do it properly as she grabbed my hair and pulled my face into her arse crack. Then she pushed it away,
"Like that." She instructed and then I watched as she moved her hand to her vagina and started touching herself. That is when I gladly buried my tongue in her backside and worshipped her like a god.
My head stayed deep in her beautiful backside for well over an hour, as she moaned with pleasure and told me what a good little bitch I was. The whole time she was getting closer to orgasm I was getting closer to my third, but I managed not to. Ellie's orgasm was loud and she dropped from being on her knees to being flat on her front, I followed as I did not want to stop until she told me to. Which she did immediately, in an almost grateful manner. She just lay there for a couple of minutes whilst I kneeled behind her. Then she pulled her panties back up in a way that seemed like it was an effort and turned onto her back to look at me.
She smiled at me lovingly. That was the part of this whole experience which pleased me the most, her looking at me with love. I remember gazing back at her unable to stop smiling. It felt really special.
She told me she wanted something light for dinner, not in such a way that it was an instruction for me, but just in the way that people do in general conversation. So I stood up and told her I'd make dinner for, we ended up just having soup as that was what Ellie decided she wanted. The atmosphere had become so relaxed that as I put the soup on the stove I actually forgot to pull the blinds in the kitchen, I didn't realise until I was putting the soup in bowls. I then did shut them as although I was incredibly relaxed I was still aware of how I looked and didn't want the outside world seeing me.
We had the soup in front room, watching the telly with the curtains drawn. When we were done I took the bowls and washed up. Then went back to sofa and cuddled with Ellie as we watched TV with the curtains drawn. It was just like we would often spend evenings at her flat, except I was fully feminized and although she had put a dressing gown on she was still in her lingerie. We watched some quiz show on the telly, we always enjoyed quiz shows we would try and see if we could get all the questions right between us and often laughed at how stupid some of the answers we gave were. We stayed there until about half seven, completely content.
"We should go back to the bedroom," Ellie whispered softly in my ear, "I've got something else I'd like you to try."
I was actually very happy as we were but even though Ellie wasn't dominating or whipping me now I just couldn't say no to her, and we switched of the TV and she led me back to the bedroom by the hand. As we entered the bedroom she shut the door behind me and then put her hands on my neck and kissed me.
"You can always stop if your not ok with this." She whispered, concerned for me. I had no idea why but I was intrigued and slightly anxious to find out. Ellie then moved her hands from my neck and unzipped my dress, looking me in the eye the whole time. We kissed as she removed the dress letting it drop around my ankles. I stepped out of it and almost fell over as I wasn't yet an expert at balancing in heels. Ellie laughed as it happened, not in a cruel way, just in a 'it was kind of funny,' way. Ellie let me take the heels off. She then undid her dressing gown and let that drop to floor revealing her stunning body once more. We carried on kissing for a while longer with our hands touching each others bodies passionately.
Ellie stopped kissing me and walked over to her chest of drawers smiling as she did.
"Remember," she said as she opened one of the drawers, "we can stop any time you like."
And with that she turned around holding a large black strap-on dildo. I had no idea Ellie had a dildo, I probably shouldn't off been surprised but I really was. It didn't click, that the dildo had anything to do with what she wanted me to try until she started to put it on. I must of looked ridiculous stood there in my white lingerie and make up, jaw dropped just standing looking blankly at her. But Ellie just smiled at me the whole time, almost sympathetically.
After she had fastened it on. she walked back to me and kissed me again.
"What do you think?" She asked softly. I had no idea how to respond. I was still erect from all the kissing and touching that had gone on before, and I was definitely turned on, but had no clue how to answer her question. I looked down at the black dildo that was now attached to Ellie's waist and just couldn't think of anything to say in response.
"It's only five inches," Ellie said raising my head as to look me in the face, "So it won't hurt, ok?"
All I could think looking back down at it, was how big 'only five inches' looked compared to the small erection poking out the front of my ruffled panties. I was still speechless and couldn't muster up anything more than meaningless sounds to answer Ellie.
"Why don't we just see what happens?" She spoke in a calm and reassuring manner. We continued kissing and touching and ended up on the bed. Ellie was on top and I was underneath. As we carried on I could feel this fake five inch cock rubbing against mine, and I still wasn't sure how I felt. I knew that I was enjoying it and I had, had gay thoughts before so I probably should off felt ok with it. But I just had no idea.
As we kept going I remained totally erect, with Ellie's strap-on pushing against me. We moved around and I ended up on top of Ellie. That's when she asked me to touch it. She moved my hand from her thigh, slowly upwards, until I had my hand wrapped around the dildo. We started to kiss again and as we did I felt my grip tighten around it, and I started to rub up and down like I was masturbating it. It was then I realised how much I liked the idea.
Things moved from a steady pace from. Ellie was clearly worried about making me uncomfortable and made sure that everything was gentle and composed. Ellie's approach to the whole thing was wonderful and made me feel incredibly safe. Especially as things progressed, and we started to do more things that I had never done before.
We got to a point where I was on my knees and Ellie was stood up, teaching me how to give a blow job. I struggled to fit it in my mouth and remember seeing my lipgloss stain parts of the dildo. I was aroused in a totally new way. Even though I petrified, I was enjoying myself like never before. From there Ellie guided me to my feet and onto the bed. Into a position similar to the one she had been in when I had helped to pleasure her earlier. She pressed up against me from behind and kissed my neck and ear making me more and more sure.
She asked if I wanted to stop and I told her not too. She kissed my back as she pulled down my panties to just below my arse cheeks. Then I felt her slowly, but forcefully penetrate me. It didn't go deep at first, but I groaned as it entered. It felt wet from the saliva I had left on it and as I moaned Ellie started to  speed up and push deeper. I could feel myself getting closer to ejaculating as the dildo penetrated further and further. Ellie thrust more vigorously I felt her skin starting to press against my backside as she went to the dildos full depth. I, erupted.
The whole thing was done in no more than a few minutes. But I was sweating and breathless. I had never felt anything like it before. I lay flat on the bed and Ellie pulled my ruffle panties back to cover up my bottom, and then kissed my cheek and hugged me from my back. She took off the strap-on and I rolled over to snuggle into her in bed. She told me she was glad I trusted her, we stayed awake for a while just holding each other.
Eventually we went to sleep and in the morning when I woke it was a warm wake up. Ellie had her arms around me and it took me a few seconds to remember I was wearing bra, panties, a garter and stockings. It made me smile when I did remember though. Ellie and I were all smiles and kisses through out the morning. She helped me remove the make up I was still wearing, and after I had my shower and looked more like me again, me and Ellie had a lazy rest off the day. We talked a little about the day before, but not seriously. We had a really relaxed and loving day. It was honestly amazing.
Unfortunately a few months later me and Ellie split up, not on bad terms, just because after we had both gone back to work we went back to not being able to see each other as much as we wanted. We said we would stay in touch but unfortunately never did and I'm pretty sure she has moved now. I was pretty down when we ended as the relationship was the most serious I had ever had and I believe it was very special as well.
I hope you enjoyed my fourth experience and as ever please leave any of your own experiences in the comments. Hopefully I will have a fifth experience to post some point in the future. Thanks for reading.
Lots of Love

xxx