Chapter 1 - Home Alone (at last)
Hi - I'm Jenny. I guess my story is fairly typical of most other transvestites. To this day, I have no idea why dressing in female clothes, underwear and especially high heels is such a turn on. If I am dressing in female attire, I have to try my best to really look female, so body hair, flab and sideburns are definitely OUT!!! I don't feel trapped in a male body, or anything - but I would love to be able to really be female sometimes! This is a story of mainly fiction, with enough real life in it to make it fun to write! I started wearing girls and women's things as early on as I can remember, starting with sneaking into my mums or sisters room whenever I could and looking through their drawers and closets. I was always amazed how different their clothes were and how much better they felt against my skin, especially the underwear. My mum was quite a sexy woman back then and wore quite dressy clothes and had drawers full of exotic lingerie and high heels. My sister is a few years older than me but at that time did not have much in the way of sexy clothes. I did love to put on her little dresses and white cotton underwear and parade around the her room whenever I could. My sister is about the same build as me and I could slip into her things easily. My mums things, while being gorgeous, I knew I would have to wait a few years before they would fit me. When I was big enough to wear her clothes, I did so whenever I could, especially her beautiful collection of high heels. So many shoes, sandals and boots!
As I grew older, I started feeling a lot different whenever I put something of my mum's or sister's on. It made my skin feel all tingly, as before but there was something else now, too. Something more, a tension that seemed to grow from my stomach to envelope my whole body and make me shiver and draw breath. I knew that I was most definitely not supposed to be wearing these clothes, that it was wrong to do so, and maybe that's where the excitement came from originally. As I hit puberty, things got really weird! I started getting hard- ons when I thought about dressing as a girl. I would very softly stroke my little clitty (I didn't call it that back then, of course!) through my mum's or sisters panties. One day while I was doing this, I was stroking a little harder than usual and the sensations just kept getting better and better. When I orgasmed, I had no idea what was happening - I thought I was going to pee or something but nothing came out. There was just this incredible feeling all through my whole body but centered around my hard little clitty. My sister had grown up into a very sexy 17 year old and had some great clothes by the time I was really getting into wearing girls things. She also had tons of high heels and makeup - this being the glam 80's. At every opportunity, I would dress up in something sexy and girly, usually just her stockings and bra with a pair of her heels too, and stroke my clit until that feeling washed through me again. I knew that this would always be a part of my life even back then. As I started to grow a bit older, I experimented with her makeup and my mum's wigs - trying my best to look like a girl. My mums clothes were about my size now so I was alawys putting on her lingerie and dresses, skirts, blouses, heels and posing endlessly in front of her big bedroom mirror any time I had the house to myself for a while. This would always end up with me lying on her bed and stroking my clitty. I can still remember the first time I came. I knew what it was (I had discussed things of this nature with my friends) that shot out of my clit but I was very surprised all the same when it happened.
After discovering that I could come, I did so at every chance! I had been wearing my mum's and sisters stuff in secret for years - pinching items from their rooms or the laundry that I knew would not be missed and taking them back to my room where I would wait until they were in bed or asleep before putting them on and masturbating with girly thoughts in my head. I loved the feel of the stockings on my still hairless legs and the tightness of her sexy panties. Sometimes, when I had the house to myself for an afternoon or evening, I would also wear a pair of my mums sexy heels - always at least 4". I loved the sandals with ankle straps and her leather knee boots with a chunky 4" heel (leftover from the 70's, I guess), these felt so tight against my calfs and there's just something about that!! I also experimented more and more with makeup - it amazed me how long it took to apply and how difficult it was to achieve the desired effect (i.e., not looking like Alice Cooper, or that guy from Twisted Sister!). But, with lots of practice over the years, I was able to eventually get a look that I liked - dark eyes and sexy red lips, with accentuated cheekbones. I thought I looked great the first time I pulled it off! With my makeup on, I would head straight for my sisters room for some underwear and then my mums closet for some heels. I would pull on the stockings first - running them slowly up my smooth legs - I still prefer stayup stockings but I do love the pull from the garters you get when wearing a suspender belt or basque. Next would be a pair of her sexy black panties - a thong or tanga in silky satin and lace. A bra or basque would be next - I loved the basque especially because it was so tight and added a bit of curve to my slim body and I could have great breasts when I stuffed the cups with stockings or tissue. Then I would put on a pair of my mums high heels - 5" court shoes or 4" sandals, also in black.
After extensive posing in front of the mirror, I would lie on my mums bed and caress my body and love the feel of touching and being touched at the same time. I would fantasise that I was a dirty little girl like I had seen in erotic magazine's and was getting ready to please my big strong man. I would start to touch my cock and ass through the tight panties, loving the thoughts that were going through my head - namely being sexy and getting fucked like a little whore. I would caress my whole body and pretend that I was in someone else's arms. I would pull my panties to one side and start rubbing my cock, watching as it got rock hard and wishing I could feel a real mans, wandering what it would be like. Then I would jerk off, dreaming of a guy fucking me, until I shot my load all over my body - and sometimes my face if I was really horny! Then I had to get everything tidied up and grab a shower before anyone got home.
So, anyway, when I turned 16, I was allowed to stay home when everyone else was away on holidays or whatever - usually my sis would be home too to look after me. The first time I had the house to myself for 2 weeks were the best I can remember. I could hardly wait until they were all gone because I knew fine well what I would be getting up to in their absence - dressing up! I said my goodbyes to them all and promised to behave myself for the fortnight - no wild parties and the like. I was (and still am) very slim with toned muscles, I am about 5'7" with blonde hair and big blue eyes. I am naturally quite feminine looking because my face is also slim - and I look pretty good when I spend some time with makeup. I do however have great legs - very long and slender but in no way skinny. I loved the way they look in stockings, especially when I'm wearing heels as well.
Now, with the house to myself, I could indulge in my wildest dreams undisturbed! I waited a good couple of hours after they left before getting started - just in case of any surprise return for forgotten items. During this time, I tried to plan out what I was going to do later but the hours really dragged in because I was so excited. It was about two in the afternoon before I decided it was safe to start. I went immediately to my room and stripped. I ran a nice hot bath full of bath oils and other feminine condiments and soaked in it for a good 15 minutes before shaving my legs and arms. I instantly loved the silky feel of my freshly shaved legs and the way the water just ran off them when I lifted them from the bath to admire them - I felt so silky and feminine. I very carefully shaved my face to get rid of any unwanted hair, i.e., all of it! Since I was only 16, there wasn't much to remove and my facial hair was still soft but I took my time nonetheless to avoid any nicks and cuts. Out of the bath, I lovingly applied moisturiser all over my body, relishing in the smoothness. After this I rubbed in a little baby oil to give my skin a nice shine.
With a warm glow all around me, I made my way to my sis's room to pick out some of her sexiest gear - practicing my walk as I swished through the house, swinging my hips and ass in the sexiest way I could. I walked into her room and opened her underwear drawer and took out a pair of black thigh-highs (stayups with a nice wide lacy trim), a black basque, black g-string and a black negligee with really feminine lace trim. Next I went through to my mums room and found a pair of heels for the afternoon - black sandals with sexy ankle strap and a 5" heel. I sat on my mums bed and rolled the stockings up my legs, feeling almost supercharged with sexual energy and luxuriating in the feel of the tight nylon against my smooth legs. Next came the basque, which thankfully could be fastened and then pulled on rather than having to fight with the hook and eye fasteners at the back. I would attach the clips to my stockings even though they were not needed - I just liked the way this looked. I pulled on the panties next and made sure I had everything tucked away as best I could. I then put on the negligee and heels and made my way back to my sisters room for some makeup. Again I strutted through the house, this time in my lingerie and high heels, loving the freedom and the feeling of walking in the heels (I have always had something of a heels fetish so actually wearing them is incredible!). I had worn my mums high heels so many times in the past that walking in them was no difficulty at all.
I sat down at Kay's (my sister) vanity on the soft stool in front of the mirror. In front of me was all manner of makeup and accessories - I was in heaven! I applied a light foundation to give me a flawless base to work on and a little powder to set it. Next I did my eyes - fairly light shadow with lots of liner and mascara to give me the smouldering look (well, I thought so anyway!). Next was a cherry red lipstick - two coats for a full effect and finished with some clear gloss. Some colour to my cheeks to heighten my cheekbones and I was done. I looked in the mirror and was very happy with what I had achieved, although it had taken about an hour - with many removals and corrections along the way. I went back to my mums room and looked out one of her wigs - a long straight black one that was easy to manage. I placed it on my head and made some adjustments in the mirror - lots of brushing got it looking really silky and I thought I looked amazing. I went over to her full length mirrors to see the full effect of everything I was wearing - I couldn't believe how sexy I looked. This was the very best I had ever looked and I was going to take my time that evening and really enjoy myself!
I looked out one of my mums little black dresses for later - a mid-thigh, very tight little thing with very thin shoulder straps. I also took out a pair of her sexiest heels - a lovely little pair of sandals with a 4.5" heel, black with a toe strap and ankle strap. The straps were each patterned with a row of little diamonds (not real obviously), which made them really elegant and feminine. I went downstairs dressed in my lingerie and heels, my heels clicking deliciously on the tiled floor of the kitchen and made some sandwiches and poured a glass of juice. I sat down in front of the TV to eat and watched some rubbish chat show about cheating spouses. As I watched, I began to fantasise about one of the guys cheating on their wife with me and how he would seduce me and make me his girl. As I thought more about this, my cock grew quite hard and big (its a fair size at 6.5" but no monster) in the tight panties. I thought about my lover having a much bigger one and what I would do with it. I started to rub my clit as I imagined what we would get up to on our hot date.
I imagined he would come to my door for some reason (it was a fantasy so there didn't need to be any real reason) and I invited him in. I would get him a drink while he sat in the lounge. After chatting for a while he would tell me that he thought I was cute and would look good as a girl, at which point I would suggest that I go get changed into some sexy lingerie. When I came back to him, he would be sitting on the couch and would tell me to come sit next to him. I would be wearing just a basque, stockings, tiny panties, with 5" heels, wig and makeup. He would tell me how good I looked and start to caress me like I had done to myself so many times, his hands resting on my thigh and rubbing gently. Then he would look right into my eyes and move forward to kiss me. Our lips would meet and then we would kiss deeply and passionately as he stroked up my thighs to my panties. I nearly came when I thought about how it would feel to have his hands on my clit for the first time, gently rubbing it through my panties. As he did this to me, I would reach over and start to feel his big cock through his trousers. I would then unzip them and take them off his legs while he removed his shirt. He would now be sitting in just his boxers and I would be able to see his huge cock making a tent in them as I continued to rub him.
I would slowly slide his boxers down his legs, watching in fascination as his enormous cock sprung free and stood to rock hard attention. In my fantasy it would be about 8 or 9" long but not too thick. He would smile at me and pull me up to kiss him again, my lingerie clad body rubbing all over his hard body. As we kissed I would take hold of his huge cock and gently play with it, stroking its length and gently squeezing it. He would then break our kiss and softly push my head down to his crotch. I would get up and then kneel on the floor between his legs again taking his cock in my hands. I would lean forward and kiss the head of his cock, then softly lick the little drop of pre-cum from the tip, squeezing out more with my hands. I loved the smooth, silky texture of it and the salty taste and started to take his cock in my mouth to get more. I would open my mouth as wide as I could and engulf his manhood before closing my lips on it about half way down. I knew it would be a challenge to get the whole thing in my mouth but I would be determined to try. I would suck on his cock like a lollypop while stroking it with my hands and cupping his balls, taking ever so slightly more of his cock into my mouth each time I went down. His cock would remain brick hard the whole time and he would moan and writhe with pleasure as I sucked deep on it. In no time, he would grab hold of my head, holding me in position as his cock twitched and he shot his cum into my eager mouth and throat. I would try to swallow as much as I could but there would be too much and some would trickle out the sides of my mouth to run down to my chin. He would gently wipe his cum from my face with his fingers and slip his cock from my mouth. Then he would make me lick and suck first his fingers, then his big cock clean. He would tell me what a good little cocksucker I was and that I should suck it again to get it hard for what I really wanted!
I would go down on his big bone again, sucking it deep into my hot, wet mouth until I felt my nose pressing against his stomach. Keeping my lips around the base of his cock, I would suck hard. I would feel his cock growing bigger in my mouth and eventually filling it completely until it was going down my throat. Then he would whip his cock out and sit me with my ass on the edge of the couch. Then he would grab my legs and put them up over his shoulders as he moved forward on his knees into position. He would then generously apply lube all over his huge tool and my ass before directing his cockhead to my waiting asshole. He would push in gently, telling me what a good girl I was, taking his time to fill my hungry little cunny with his cock. I would moan loudly as his cock kept pushing in, feeling it fill my ass until it was all in. Then he would wait until I was ready (it's much better for both parties if you are!) before ever so slowly pulling a little bit out and pushing it home again. Before long, I would be thrusting my hips forward to meet him and he would lengthen his strokes. Soon, I would be feeling his entire cock fucking my tight hole as he reached down to kiss me deeply. As I got fucked hard, I would wrap my legs around his back and pull him tighter as I moaned for him to make me cum. He would fuck my ass hard until my clit shot my cum all over our bodies and my ass gripped his cock like a vice. My tight ass would make him thrust hard into me one final time before his cock exploded inside me and I could feel his spurts jetting deep into my ass. He would leave his cock inside me as it softened and I would feel his cum leaking out around it. Then he would take it out, get cleaned up and dressed, then he would leave after giving me a big kiss to say thank you. I would be left on the couch with his cum dripping out of me and feeling fulfilled!
I had bought a large pack of condoms for my time alone in the house, so I slipped one onto my clit now to prevent making a mess of my sisters lingerie. As I thought about what I would do with my man, I couldn't help myself and came hard into the condom. I had hardly touched my clit but my orgasm was so strong I felt my legs going weak as I pumped my cum into the rubber. There was so much of it - much more than ever before and I knew that this was something I would need to try for real as soon as I could. Little did I know that, very soon, I would have the most incredible experiences with the most unlikely people!
After I had recovered from my orgasm, I removed the condom and cleaned up my clit and tucked it back into the panties. Wow, I thought, what an amazing experience. I had to have more! I walked back up to my sisters room to do a bit more exploring since nobody would be home. I loved the feel of the air blowing around my legs and body as I walked in my lingerie and heels up to her room. Kay's room was typical of most girls of her age (now 20) - very pretty and neat and always smelling nice. I loved being in her room because it made me feel so feminine and I wished my room could be like hers. Against the opposite wall from her vanity was her double bed. I had never searched through the drawers under her bed before and wondered if there would be any hidden surprises. I pulled the first drawer open to find bags of her old clothes and underwear - I had a quick look through this but was disappointed that there was nothing really sexy here apart from a couple of miniskirts. I took one of these anyway for use later in the week. It was a very short grey miniskirt that I knew would really hug my ass and thighs when I put it on. I closed this drawer and tried the other - even more disappointing - this was just spare bed linen and towels! I felt let down. I was sure there had to be something in here so I pushed my hand as far back in the drawer as I could. I felt something different here - it was a plastic bag?? I grabbed the bag and pulled it free, knowing somehow that there was some new treasure hidden in it.
As I opened the bag, my whole body was trembling and my heart was thumping in my chest. It almost stopped when I looked in. In the bag was Kay's selection of vibros and dildoes! I emptied them all out to look at them - there was a 5" slim vibro, a bigger vibro (about 7"), a big rubber dildo at about 8" and very thick - and most astonishing of all was a huge strapon dildo that was about 9" long and about 2.5" thick. Fuckin' hell, I thought! I was almost angry with myself for not discovering her stash sooner and, at the same time going weak at the knees with anticipation and lust. I knew what I would be doing later that night for sure now!! Later, I would give my mom's room a thorough search to see if I had missed any such treasures in her room too!
What was I going to wear for this adventure, I asked myself? I almost ran back to my mum's room to grab the sexy black dress I had looked out earlier. I took off the negligee and removed the shoulder straps from the basque. I held the dress open and stepped into it, pulling its tight material up into position on my body. I put my arms through the spaghetti straps and it was on! I had a quick look in the mirror to see how it looked and almost fell in love with myself. It looked so gorgeous and sexy and made me feel so feminine. I also took off the heels that I was wearing and replaced them with my mum's really sexy sandals. I walked into my room to grab my box of condoms, then to the toilet to get some lube (I knew I would need this soon!). I found a jar of Vaseline in the bathroom closet and knew this would work just fine. I strutted like a slut back down the hall to Kay's room and threw the condoms and lube onto her bed. I posed in front of her big mirror, pretending I was dancing and flirting with a guy at a club. I held myself and pretended that we were dancing to the slow tunes at the end of the night, with him whispering that he wanted to take me home and fuck my brains out. Telling how sexy I looked in my dress and heels, telling me that I was gorgeous and how badly he wanted to screw me.
I kept my dancing up for about 20 minutes, getting hornier by the minute as I thought about what I was just about to do. I could not wait any longer! I jumped onto Kay's bed and grabbed the big dildo. I lay down on my tummy with the dildo in my hands in front of me. It felt pretty real to me, the uninitiated. It was soft and hard at the same time, kind of like my own clit when it was aroused, but not as hard. I squeezed the big dildo in my hands loving how it felt. I then brought it up to my lips and kissed it, all the time imagining it was a real cock and I was pleasing my lover. I then licked the balls and up the shaft, getting it nice and wet. It tasted funny and I wasn't sure if it was the rubber that tasted like this or if it was from Kay's pussy! At once, I hoped it was from her pussy and I was imagining I was licking her cum from her lovers cock just after he fucked her. I fantasised that Kay was sitting on the bed watching me suck her boyfriends cock, all dressed up like a slut and fully made up. She would encourage me, saying things like, 'yeah that's it honey, just lick it gently', 'feel the tip with your lips', 'take it in your mouth'. At which point I grabbed the dildo and sat it on the bed so that it was pointing straight up. I moved into position above it and lowered my mouth onto it, sucking in as much as I could into my mouth. It felt incredible having this hard, yet soft, cock in my mouth and I knew I had to try to get it all in and deep throat it.
As the dildo became more lubricated with my saliva, it slipped in and out on my mouth much easier and I could swallow a bit more every now and then. I was really enjoying myself! When the tip of the dildo hit the back of my throat for the first time, I nearly gagged and quickly removed it. Wow, that's harder that it looks, I thought. I felt turned on with the thought that most girls must experience the same reaction when they first go down deep on a big cock and knew I had to try and get it all in to please my man. I started slowly again and soon had it in as far as before. I knew what to expect this time when it hit my throat but it was still hard to control the reflex so I went carefully. As I took more in my mouth, I felt the gag coming again but this time I kind of kept trying to swallow and it felt better. I felt the head of the dildo enter my throat and nearly came again right there - I felt like the dirtiest little slut imaginable. I eased it back into my mouth sucked on it as I prepared to try and take the whole length. I felt so horny as I sucked on it and started to push my mouth right down. I felt the head go into my throat again and this time I pushed further. I felt my throat stretch a little to accommodate this big dildo and it was a bit uncomfortable. However, I was on such a sexual high that I just kept it there and pushed even more in. I could almost feel the balls of the dildo near my chin and knew I was almost there - only about another inch and a half to go. I brought it back into my mouth and sucked on it hard, imagining the pleasure this would give some guy - hopefully for real soon! - and got the dildo lubed with more saliva. I relaxed myself and pushed the dildo down my throat - I got it as far as before with no trouble and went for the final push. I eased my head down and felt the dildo slide further down my throat. I pushed a little further and was rewarded with the feeling of the balls rubbing my chin. This is so hot, I thought, I'm sucking a huge cock all the way into my throat and I love it.
Again I thought of my sis and her boyfriend being there and Kay saying, 'wow what a little slut you are, I think you should have a girls name cos you sure suck cock like a girl'. I hadn't even thought about this before but it turned me on so much now. I had to have a girls name for occasions like this. I wanted something cute and feminine and went through a few possibilities before thinking of Jenny. Jenny! I loved it. It was perfect. I would be Jenny from now on whenever I was dressed as a girl. 'mmmm, that's it Jenny', Kay would say, 'I can see you love sucking that cock. I bet you would love to be fucked like a girl too, wouldn't you'. God yes, I thought back, I would love your boyfriend to fuck me like he fucks you, will you let me Kay, please? Please tell me how to take it like a girl. 'ok - first, take it out of your mouth, silly! now go over and fix your lips - they're all smudged'. I looked at the dildo and discovered it was covered in red lipstick - that would be so hot on a real cock, I thought to myself as I got up to redo my lippy. With my lipstick fixed, I went back over to the bed and took the big dildo in my hands again. It was still warm from the sucking I had given it! 'ok Jenny, now get a condom and roll it over his cock - you don't want to be having any babies at your age!' I imagined her saying this as I opened a condom and rolled it down the dildo. 'ok Jen, your pussy will need some lube cos that's a huge cock - use your fingers to rub some of that Vaseline around and into your pussy. Here, let me help you with that'. As I rubbed the lube around and into my ass, I imagined Kay was doing it and telling me to relax and be a good girl.
I had experimented with various penis-shaped objects in my ass before, candles and the like, but never anything as big as this dildo. I stuck a lubed finger into my ass, as ever loving the feeling just as it enters and begins to stretch my hole. I lay on my back with my legs spread open, fingering myself. I imagined that I was playing with my clit and getting my pussy ready to be fucked hard with that monster cock. Soon I had two fingers inside me and was lying back on the bed in heaven. I was getting really horny and needed something else besides fingers in me. I didn't think I was ready for the dildo without some warming up beforehand, so I placed it on the bedside table and picked up Kay's little vibro to start things off. It was a little ivory coloured vibe - the usual kind of bullet shape. I lifted it to my nose and smelled it to see if there was any of Kay on it. I had never harboured any sexual thoughts about my sis before this night but finding her stash of sex toys brought her in to a whole new light. I would gladly have fucked her brains out if she appeared right now (reality aside for the moment). I thought I could detect a trace of her pussy on the vibe and I grinned as I thought about my dirty big sis and her toys - if only she knew who was playing with them now! I licked the vibe and rubbed a small amount of lube onto it - my ass was already well lubed but this would make it easier to get in. I lay on my back on the bed and spread my legs wide again. I rubbed the vibro around my ass without turning it on, then pushed it gently in. It was so smooth and shaped so neatly that it just slid right in. I felt so dirty and hot lying there with my mums black dress hiked up over my tummy to expose the garter straps of the basque holding up my sheer stockings. I had my legs open so wide the heels I had on were almost pointing in opposite directions. I held the vibro inside my ass and reached down to twist the base to turn it on. I jumped about a foot off the bed when I turned it on - it went straight into super mode, no slow speed for this thing. I could feel it buzzing strongly against my clenched sphincter and when I began to relax, it felt so amazing. I just lay there for about 15 minutes doing nothing but feeling the vibro buzzing away inside me, imagining that this was foreplay with Kay's boyfriend. I slowly started to push it in and out, feeling it come right out of my ass and then force its way back in past my soft ass lips to fill me up again. I fucked myself very slowly with her vibro for the next 10 minutes or so.
All the play with the vibro had got me so turned on that I was ready to try the dildo. I removed the vibe from my ass and stood it up on the bedside table. Next I got up and took off my mums dress so that I was wearing only Kay's lingerie and my mum's sexy heels. I had a quick look in the mirror to make sure my makeup and hair were still okay - don't want to look a mess for my man. I walked around Kay's room for a while, strutting and pretending I was teasing my lover. Mmmmm baby, you've got such a huge cock. Do you wanna stick your huge cock in me and fuck me like a whore? I wanna feel your cock filling my tight little ass as I bounce up and down on it. I wanna put my legs over your shoulders while you shove your tool into me, fucking me as hard and deep as you can.
I picked up the dildo, loving the way it bent and swayed in my hand as I rubbed lube onto it, and went over to the bed. I got onto my hands and knees and placed the dildo standing up behind me. I leant back until I felt the head on my ass and started to rub it round the opening, moaning as I did so and wishing again that it was a real one. I pushed down a little onto it and felt it stretch my hole - it was huge! I felt disappointed, even anxious that I might not be able to take it. Then I thought of Kay being there and teaching me - 'just relax Jen. Let it happen slowly. Push out as it goes in and stay relaxed. I know you want to feel my boyfriends cock inside you and find out what a girl feels like to be filled up like that'. I grabbed the dildo with one hand and guided it back to my hole where I felt the pressure once again pushing at my ass. I started to lower myself onto it, pushing out with my ass as it entered. My ass gave in and I felt the head pop into me. I almost screamed as my sphincter gripped it tightly and shot a bolt of pain right through my body. I wanted this badly though and was not about to give up now. I kept just the head inside my ass as my sphincter spasmed, gripping and releasing the huge cock that was invading me. I felt like I had just put a bolt of lightening up my ass! Slowly, the pain began to subside and I started to feel really dirty again at the thought of what I was doing. I relaxed my ass as much as I could and started to slowly lower myself further down onto the big cock. I felt an inch, maybe two, sliding in and felt the pain shooting through me again, so I slid it back a bit and waited for the pain to go away. I could feel my ass being stretched and had never felt anything so enormous in me before - it felt so good. As I got used to the dildo, I gently rocked back and forth on the bed, feeling it moving in and out. I started to push more of it into me as I got hornier and hornier - there was very little pain now - it had been up my ass for about 20 minutes altogether and I reckoned I was getting used to it.
I felt round behind me and figured I had about 3 inches of the dildo still to get in, so I sat back on my heels sitting straight up and lowered myself fully onto it. WOW! I felt the entire length sliding in and I could then feel the rubber balls pressed tightly against my ass and I knew I had done it! I just sat with it inside me for what seemed like hours but was in fact only about 5 minutes - getting used to the feeling of utter fullness and ecstacy. I had not even touched my own clit yet and it was so hard that I thought it would hurt if I did. So, rather than touch it, I got back into character as Jenny and started to very slowly rise up to feel the dildo sliding out of my ass. When only the head remained inside, I started to lower myself again, feeling it force its way in and fill me up again. I continued fucking myself very slowly for about 10 minutes, thinking of Kay telling me how well I was doing with such a huge cock in my pussy for the first time. 'mmmmm, that's it Jen, doesn't it feel wonderful as it slides in and out? Don't you want to be fucked hard like a slut?' Oh fuck yes! Yeah I want that Kay, I want it so much. Make your boyfriend fuck me hard!
I started to rock back and forth on it again - feeling the whole length sliding in and out of my ass. Quicker now and I could feel something building up inside me. I reached for a condom and rolled it over my clit then started bouncing up and down on the dildo, faster and harder than before. I was fucking that huge cock like a slut from a porno movie and cannot fully describe the feelings that were going through me. I felt so dirty, so feminine, so slutty, so girly, and so proud that I had taken this huge cock inside me. I thought this must be what it is like for Kay when she gets fucked and I felt like I had somehow connected with her in a way I never had before. I started to caress my body and looked down at my lingerie-covered body as I pumped my ass. I watched my clit bouncing up and down as I got fucked hard in the ass and this finally sent me over the edge. I sat down hard on the dildo as I came, feeling it right inside me. As my clit erupted into the condom, I could feel my ass gripping the dildo tight and squeezing it as I came. I knew that if I had a real cock in me right now, I would be milking every last drop of cum out of it with my ass muscles. I came so hard that I couldn't focus for a few seconds and felt incredibly light-headed and dizzy. I collapsed on the bed with the dildo still fully up my ass, not able to take in the sensations and feelings that were running through me. I knew this would not be the last time that this happened.
I finally sat up to remove the dildo - it felt delicious as it slipped from me, making an almost comical pop as the head came out. My ass felt like it was on fire now so I got up and went to the bathroom, taking the dildo and vibe with me to wash them. When I got to the bathroom, I cleaned myself up and bent over the bath to rub some cooling lotion into my ass. 'That's a good girl, Jen! This will make your pussy all better and feeling nice for tomorrow when you get fucked again', I imagined Kay saying to me as she applied the lotion to me. 'Oh my little sister Jenny is so hot and such a cock-hungry little bitch! We can have so much fun together with boys...and maybe girls as well!!'
I stripped off all the lingerie and heels and got everything tidied up before taking a short pink satin nightdress and panties from my mums drawer. I put these on before getting into Kay's bed, thinking what a great thing it would be to be a girl and fuck boys, men...and girls all the time. I loved the feelings in my cock when I played with it too much to ever fully be a girl but I had some fairly good ideas about what would be good. I had never seen a gorgeous feminine pre-op transexual before but this was what was in my head that I wanted to be - the best of both worlds! A beautiful smooth slim body with all the right curves and breasts, dressed in sexy lingerie, heels and tight outfits. But underneath it all I would have my cock - I could please, or be pleased by anyone male, female or in-between. I drifted off to sleep with these delicious thoughts in my head...
Continued in Chapter 2 - The Party, where I discover one of my best friends has a secret and that her older brother has got the hottest fiancee. Ever!
This is my first attempt at writing my stories, so I would really appreciate your feedback! Please mail me at jenny_loves_a@hotmail.com xxmmmmwahhh!