OK the disclaimer - This is a tale of fiction between a 13 yr old boy dressed as a girl and an older guy. There is some concensual and some no consensual so if thats not you bag then dont read any more. This is my first submission so if you like it let me know, also contructive criticism. If you wanna send a nasty email, send it elsewhere.
Again, if you like the story and want it to continue, let me know too
Rushing In
My name is Paul, I am now 19 and here is the story of how I started cross dressing and also how I started to be a bit of a cock slut.
It all started just after my 13th birthday and my mother (who had a hard time accepting that the 60's ended over thirty years ago) was going away on another spiritual trip. These trips happened every month or so and I was left under the semi-watchful gaze of my sister. She was 18 at that time, had a boyfriend, so when Mum was away, I was pretty much left to do my own thing. This particular trip she was particularly pissed off because she was going to a weekend rave from Friday to Sunday but we agreed amongst ourselves that I wouldn't be a problem and she would still be able to go.
At thirteen I already had a wanking obsession so a whole weekend of internet porn seemed like a good plan, so I was looking forward to my first real weekend alone.
As is customary when telling a story, I should really tell you a little more about me. I live with my mother and sister, Julie, in the North of England, close to a city called Manchester. I have never met my father and to be honest, I don't even think my mother knows who he is. At thirteen I was very slightly built, very girly frame, 5ft 2 and with my mother's penchant for everything 60's, it rubbed off on me a little and my hair was past shoulder length, blond and very wavy, usually worn in a pony tail. Because of my look, I was bullied a lot at school so had very few friends. I loved my internet porn and up until this point, I had only really watched straight stuff with the occasional bit of guy on guy. I was still a little naive about anything else. Little did I know how much this weekend would change all that.
My week at school dragged on as usual, my grades were always good, my homework on time, several beatings for being the `hippie freak' and Friday couldn't come soon enough.
My mother packed her incense and whatever other crap she took with her and at 5pm on Friday she left with her weirdo buddies. Barely had her car left the drive when Julie called her boyfriend and told him to come and collect her. She gave me the money that Mum had given her for the weekend (well some of it) and gave me the usual sister to younger brother talk,
`Keep your fucking hands off my stuff, no parties, and don't let any strangers in', She hugged me (we were quite close) and ran as she heard the car horn outside.
When I was sure she wasn't coming back I went to my room, fired up the internet and prepared for my first wank of many this weekend. I visited some of my usual free porn websites and was casually stroking my stiffy as I flicked through the images. When I said earlier that I was slight built, this extends to my cock too. I was about 4" when fully hard and was uncircumcised and I loved the feel of the skin stretching back over the head of my cock.
It wasn't long before I shot my first load into a prepared bit of tissue and as usual, 30 seconds was enough to see me ready to go again.
I decided to go into a few chat rooms on AOL because at the time there were lots of sex talk ones and I used to watch in on some horny conversations and being a bit of a swot, I enjoyed written sex stories like in Playboy for the occasional jerking session (I was very easily horned up). While I was in one of the chat rooms, somebody asked the best place for free stories online, I watched in interest, pen ready, for any answers. The answer that came up was one which would change me forever. It was Nifty.org. Within two minutes I was logged into the site and was instantly amazed at the content. I soon realised that there was very little of my regular stories and started with bisexual. I then saw that stories involved teens and younger, I was agog at the screen. Then I started to read about a guy with a 9yr old and a 13 yr old girl. I was almost cumming without even touching myself. I went back to the front page and saw the crossdressing
button and found a story of a young lad, similar age to me who dressed for the first time while his family were away and just the description of his sensations while getting dressed made me come all over the floor. I couldn't believe I had shot my load at the story. After cleaning up I continued, fascinated, but I dint know why it was having this effect. The story was a long one and it told how the boy used to dress as a girl, walk his neighbourhood, and then eventually he got picked up by an older guy and even though gay stories had never really done it for me, I could see myself as the boy and was feeling hornier than ever before, even when it described the guy fucking the virgin boys tight arse.
After I finished the story, I just sat at my computer, going over the story time and time again in my mind. Did girls clothes feel that good? They were just clothes weren't they? The story must be rubbish fiction, mustn't it?
I went downstairs, made some dinner, but as I microwaved my meal and sat eating, the story was playing over and over in my mind. So much so, without a conscious thought, I stopped outside Julie's door as I was going back to my own room. I walked into her bedroom, looked into her wardrobe at her clothes, they just looked like Julie's clothes! Nothing special. I opened her underwear drawer, there was lots of lace and frilly stuff in there, that was different but I just dismissed it and went back to my room.
My computer was still showing the Nifty Archive and I opted for another TG story with a young boy and barely got a few paragraphs in when I was rock solid again, and the story had only covered the 13 yr old boy (again) shaving himself fully and putting on the clothes. I sounded so good in the story and I was still confused as to why it was affecting me this way. I realise now that it was sensations being described that I hadn't experienced so the novelty alone was appealing.
I was alone, raging hard on, and my mind was doing cartwheels. I had to see what the fuss was about, so I headed for the bathroom. I ran a shallow bath and took my sister's razor from the shelf, soaped up my legs, they had a little blond fuzz all over, I didn't think I would even tell the difference but if I was going to follow the story I'd do the lot. I nicked my ankle once but it wasn't too bad. I then soaped up my cock and balls and very gingerly shaved the little pubes I had. I probably spent a good 20 minutes in that region, terrified of cutting anywhere there. My chest and armpits had virtually no hair so that part was done in minutes. As I sat in the bath water, I ran my hands over my now totally smooth body and it felt a little different but I didn't think it was that much so I climbed out of the bath and dried off. The towel felt different as I dried my balls, it felt softer and I realised it was a lot more sensual, I
was instantly hard. Next stop, Julie's room.
Being a close family, I had seen Julie getting dressed many times so women's clothing held no mystery to me so I wasn't going to be confused by a bra or a garter belt! I decided I would play my dressing along the same lines as the first story where the main character picked out the outfit he thought his sister looked sexiest in. I already had an outfit in mind, after all, this was a one off and I may as well do it properly!
As Julie was only an inch taller than me and just as slim, I knew everything in her clothing would fit me just fine. I went for underwear first (obviously) and chose a lacy bra with matching panties. As I slid the knickers up my legs, the soft feel gave me an instant hard on, it just felt so nice. I quickly fastened the bra and then put a black suspender on and chose a sheer pair of stockings and surprised myself how well i had observed Julie getting ready, no ladders in the stockings!
Underwear on, I now went straight for a sexy red dress that she saves for special parties or celebrations and stepped into it. The soft cotton on my stocking legs felt strange but still got me even more horny. Final touch was to grab a pair of black four inch heels, strapped them on and then took my first teetering steps in my sister's clothes. I deliberately hadn't looked in the mirror until now as I wanted to shock myself at how ridiculous a 13 yr old boy would look dressed in his sister's clothes. Without thinking, I pulled the elastic off my ponytail, shook out my hair, then I slowly closed the wardrobe door to reveal the mirror. To say I was stunned, was an understatement. The comical sight that I expected to see, wasn't there. I looked in the mirror and saw a pretty girl looking back at me. Was I that feminine in the face? I had become a girl. A plain girl, who needed make up, but a sexy girl was definitely there. I
reached into the stocking draw and found some padding for my bra and applied just a little bit of eyeshadow, lipstick and powder as I had seen my sister do in the past and looked at the final result. I fancied myself!
For the next hour I wandered around the house being my sister and for the whole time I was playing out the story I had read on Nifty, I was even imagining playing with another guy's cock and every time I did I could feel my cock straining on the lacy panties. I was so comfortable and felt so sexy I didn't want to change back into my own clothes, so I decided to go and see what chat rooms were available for cross dressers on AOL.
After a very brief search I found one called CD Admirers', so I set up a new name YngCDManchester and entered the room. I watched for a while as people chatted about nothing in particular and then one guy asked if there was anyone from Manchester. Without hesitating (or thinking) I typed Yes' and waited for a response.
A request for private conversation Popped onto the screen, I clicked accept and said , `Hi there'
Dave: Hello there, how are you tonight
Me: Fine thanks, you?
Dave: Yeah good, where in Manc are you?
Me: Middleton you?
Dave: Yr Joking, I´m from Middi too!
Me: Wow, how old r u?
Dave: 22 u?
Me: Younger than you lol
Dave: How much younger?
Me: A bit
Dave: A big bit or a little bit lol
Me: A big bit lol
Dave: OK is this a wind up?
Me: No I´m genuine
Dave: OK turn yr web cam on then
Instantly I panicked, I didn't respond straight away but then thought, well my own family wouldn't recognise me now, why not? It's not as if I would ever do anything more would I?
Me: OK, give me a second to plug it in. Are u gonna put yours on too?
Dave: No worries
As I was sorting the cables on my web cam, Dave's face appeared on the screen. He was a nice looking guy, slim with short dark hair and he was smiling. I finished setting up the cam and turned it on and watched for his reaction.
After about thirty seconds he smiled broadly and I could see him starting to type.
Dave: WOW WOW WOW
I laughed
Me: Are you taking the mickey?
Dave: No, yr fuckin gorgeous!!!!
Me: Ha ha OK thanks
Dave: Why have I never seen you on here before?
Me: Its my 1st time
Dave: First time on here you mean?
Me: No 1st time I got dressed up
Dave: Wow then you are very gifted lol
Me: Tnx again, why are you not dressed as a girl
Dave: I don't, I just love TVs
Me: Cool, have you met any from here?
Dave: Nah they usually really old on here, some are just funny to watch, but you.... are u sure yr not a girl pissing around?
Me: No, really a guy !!
Dave: Can u prove it?
Me: You wanna see my cock lol?
Dave: lol well yes but I wouldn't ask that
Me: How about some of my boob stuffing?
Dave: Ok cool
I pulled a wad of tights out of my bra and waved it at the screen. Dave gave a thumbs up so I stuffed it back and rearranged my bra.
Me: satisfied now?
Dave: Yeah cool
Me: So are you really a boy?
Dave: Ha ha you wanna see MY cock? Lol
Without thinking, I answered YES, Dave asked if I was sure and I brazenly said YES again. I don't even know why I did, but he stood up, undid his trousers and pulled his cock from his pants. It was rock hard and its hard to guess from a camera but I reckoned it was a fat 8" at least. It was my turn to reply with WOW WOW WOW
He laughed as he sat down and saw my message, but as we spoke for the next 15 minutes all I could do was imagine holding his big fat cock and I even imagined what it would be like to suck it. My mind even started to picture him taking my virginity and sliding it into my hole. I tried to clear my thoughts, but they wouldn't go away.
Dave asked me my name so instantly I adopted my sister's name, after all, I was her tonight. Then the subject of my age came up again
Dave: Ok so how old are u really?
Me: Really?
Dave: Yes really!!!
Me: OK 18
Dave: Really!!!
Me: No
Dave: Tell me please, you are gorgeous but I would like to know
Me: You will vanish if I tell you
Dave: Darling, I wanna kiss you even if you were 14 lol
Me: Ha ha well I am 13!
Dave: No way!!!
Me: Yep, bet u don't want me now
Dave: I would love to have you Julie, right now, let me come to your house lol
I knew he wrote it as joke but my adrenaline was so pumped up I couldn't help myself, I was a girl and I wanted this guy but I still didn't dare bring him to my house. I could see me typing and I was horrified but I couldn't stop myself
Me: I couldn't do that!!!
Dave: Yeah I know, shame though lol
Me: But.....
Dave: But?????
Me: I could come to yours!
Dave: Yr kidding?
Me: I thought you wanted me?
Dave: I do!!! But yr winding me up now
Me: I´m not!!! But.....
Dave: OK I knew there would be a but
Me: No it's not a bad one, it's just that I have never been with a guy
Dave: hey hey hey its ok, would just love to meet you honey!
In my stupid naivety I just asked him for his address, not thinking about anyone seeing me leave the house or anything and when he told me where he lived, we laughed like crazy, he lived less than 5 minutes from me. With hindsight, it's probably the most dangerous thing I have ever done, but I agreed to meet him at his house in an hour. I signed off, and for some bizarre reason I packed an overnight bag with change of (female) clothing, make up and shoes. It was 11pm as I left the house and after a sneaky peek up and down the road for any neighbours I set off. Less than a minute into my walk I saw my next door neighbour and his son walking their dog. The younger of the two smiled and winked as I walked past and I threw him a smile (nervous as hell) and as I got a few steps away, I heard him comment to his father how `hot' I was. My confidence had peaked!
To this day I cannot explain how little nerves I felt up to this point. I knocked confidently on Dave's door and he answered wearing shorts and a T-shirt. I beamed up at him, I didn't realise online he was over 6ft tall and as he closed the door I suddenly felt very small, very alone and very scared. Dave sensed this, put an arm round me and gave me a very gentle and quick hug and then led the way to the living room. He asked me if I wanted a drink, I asked for a coke. As he got the drinks I sat on one end of the settee. He brought the drinks back in and sat next to me, not too close and started to chat. I soon felt more relaxed and while still nervous, I soon became lost in his deep blue eyes. I felt like a girl, I wanted to be his girl, I wanted him to hold me. As I became more relaxed I think Dave could see it and moved a little closer and put his hand on my leg and gently stroked it. I instinctively rested my hand on his and
looked up into his eyes. He leaned forward slightly, I closed my eyes and then felt his lips touch mine. Just a peck at first and then he pushed tight onto my lips and I immediately opened my mouth and felt his tongue probe deeply into my mouth. I had never been French kissed before but he was so gentle with his kisses I felt so natural and let him lead the way.
As we kissed more I had my arms around him holding him tightly as his left hand started to caress my leg under my skirt, slowly moving further up and around until I felt his fingers teasing the bottom of my panties, just touching my bum cheek. I let out an involuntary coo as he touched me and this was obviously his signal to move further and his hand was inside my pants, caressing my arse. After a few minutes of relishing the touch of this man, he effortlessly repositioned me so I was kneeling astride him on the settee, our lips never losing contact, but now he had both hands on my bottom and was sliding me further forward until I felt his rock hard cock pushing into my crotch. With his hands controlling my movements, he was grinding me on him and my own cock was so hard it was hurting, needing attention. Dave took my hand and guided it towards his tenting shorts and instead of touching it through the material, I took the waistband and stretched
it over the monster which was trying to escape and stopped kissing just long enough to see just how enormous his cock was. It was like my forearm! It was a very fat 9" beast, pointing directly at me and as I resumed kissing his lips, took it in both hands and started to stroke it bringing deep moans from Dave. His gave me the confidence to lift myself and push his cock through my legs so it was wedged between my arse cheeks inside my knickers and started sliding teasingly up and down. He was oozing pre cum and this was making it very slippy down there, almost like a wet pussy. This was soon too much for him and he asked if I would like to take this to the bedroom. How could I refuse?
As we walked into the bedroom, Dave quickly stripped off his shirt and shorts and lay on the bed to watch me disrobe. I knew the attraction was the underwear so I kicked of my heels, dropped the dress to the floor and crawled slowly onto the bed, stopping as my mouth reached his throbbing meat. I was still a little uneasy with sucking a man's cock but again, instinct took over and I started flicking all up its length with my tiny darting tongue and then longer strokes from base to tip and then I lifted his cock to my mouth and plunged as much of the monster into my tiny mouth. Dave yelped with delight as I built up a rhythm on his cock, I moaned as I discovered how good his precum tasted, and I thought it couldn't get much better but then he spun me round so my mouth was still planted on his cock but his mouth was right in line with my virgin hole. With a deft single movement, my panties were pulled to one side, my cock released into his
other hand and his tongue buried deep into my little cunt. Partly through shock and partly through delight of this new sensation, I yelped like a puppy and had to concentrate hard to keep sucking his delicious cock. Dave's tongue went deeper and deeper into my tight hole as he toyed with my cock and I felt my orgasm building, he must have also sensed me tightening up as he switched his position slightly and took my tiny cock and balls completely in his mouth and flicked them all over with his tongue but in less than a minute I erupted with the best orgasm of my life. As I shook with the aftershocks, he told me not to stop as he was so close behind me and in seconds I felt the first heavy shot of sweet juice hit my throat. He shot 7 or 8 solid squirts and I couldn't swallow fast enough so half went all over his belly and balls. As he stopped shooting I couldn't stop licking and sucking him so I lapped up all of his man juice and kept
licking until he lifted me again, and took me in his arms and held me tight. We kissed gently yet passionately and then drifted off to sleep.
When I awoke, Dave had removed my stockings and suspender belt and was kissing and licking my inner thighs. When he saw I was awake, he smiled, turned me onto my belly and started massaging and kissing my back, all in silence and as he got nearer to my bottom, he slid my panties down and threw them to the floor. Here I was, a 13 yr old boy, in bed with a grown man, wearing only a black lacy bra and this man was ohhhh probing my hole again with his tongue. Pushing my legs apart and lifting me with his hand under my belly while the other hand teased my now hard cock. Daves tongue went deeper than the previous night and the feelings were sensational. I automatically pushed my behind higher and higher, not realising I was giving the strongest signal yet that I wanted him to fuck me. His own state of arousal meant he wanted to and I wiggled deep onto his tongue I heard a sound of a cap being flicked on a bottle and then a squelchy sound, he was
lubing his cock, I had no idea.
When Dave's tongue stopped probing my hole I was still humming contentedly and wasn't aware of him shifting position until I felt the hot head of his cock pushing hard against my hole. Immediately I knew what was happening and equally as quick I knew it was too big for me and tried to move. As I tried to protest I felt Dave press hard agaist my back to hold me still and pushed slowly but persistently on my tight hole with his rock hard cock. I started to scream with pain, that´s when the first punch landed, right on my jaw. The shock stopped my scream and he carried on pushing and I felt the head of his cock pop past its barrier. The pain was like being stabbed, the stretching was more pain than I had ever felt before yet still he was going deeper. I started to cry hard and then a second, third and fourth punch came to the side of my face like machine gun fire. I was terrified and the tears were flooding down my face. My hole was
of fire as I felt his balls pressed against my arse and I truly wanted to die with the pain.
`Enjoy this you fucking whore' he cackled as he pulled his cock completely out of me and then rammed it in fully and then started fucking me like a dog, violently and so fast my head was banging against the wall. What was probably only a minute or two felt like an eternity and the pain was crippling my consciousness. Eventually I felt his hot come flooding my insides and the frantic humping of my hole subsided and Dave collapsed on top of me, panting and laughing a sick laugh.
As he slid his still hard cock from me, I thought my ordeal was over but no. As I lay with my eyes closed, I felt myself being flipped over like a rag doll and then he straddled me like a horse. As I opened my eyes I was met with a view of his still raging cock covered in my blood, shit and his come heading towards my mouth. I tried to clamp shut but a swift punch to my guts forced my mouth open and he rammed inside demanding I clean him. His impatience grew as he rammed his cock too deep into my mouth causing me to gag and every 20 seconds or so delivering a hard slap to my face. At some point then I passed out
To be continued?