By (user no longer on site)
over a year ago
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I alternate a lot between male and female mode, but I have always dressed enfemme, ever since little, and over the years, progressed to wearing make-up and wigs (My Mum had a good selection, fortunately for me). I used to wear my mum’s clothes but once, when I was 18 and my parents were away, I ordered some clothes from a catalogue – a skirt, blouse, stilettos’ and lingerie sets.
At the same time, I went to a party with a load of friends. An all night do at a girls house while her parents were also away, you know the sort of thing.
Anyway, as the night wore on, people (blokes) were in and out of the bedrooms, and a few had gone through the draws and there was women’s lingerie all over the place together with a few sex toys!! I couldn’t help myself, and stuffed as much as I could down my trousers and left, walking home with a huge bulge in the front of my pants, not just caused by the size of my cock, lol.
The next day, after work, I bathed, and shaved all of my body, not that there was much to shave in those days.
I then dressed in a combination of the clothes that I had ordered and the panties and bra that I stole from the party, and put on my make-up and one of my Mums wigs.
I can clearly remember the lingerie. Matching panties and bra, lace and pale blue.
I then lubed myself with nivea (!!!!) and got out the dildo that I had also stolen from the party. It was a very realistic cock, about 8 inches long with balls. I’d never seen anything like it before, although I had often used lots of different objects on myself. I was a virgin as far as anal was concerned, never having had a real cock before, but I was well used to taking things up my arse, and had progressively used (I’m gonna hate myself for revealing this, lol) a sterident tube, lol, a hair brush, the handle of a paint brush, carrots, cucumbers and anything else that was phallic, so I was sure that I could take the real thing, but this was the nearest I had come and the best test yet.
I’d always wondered what it would be like to have a real cock inside me and used to masturbate whilst fantasising that my own cock was in my arse, fucking me and filling me with cum.
I even managed, being a lot more supple then than now, to suck my own cock and fill my own mouth with cum, which was such an incredible turn on but a poor substitution for what I really wanted and desired.
Anyway, I squatted over the dildo, and rested it against my arse. It felt HUGE. Enormous in fact, and I felt so disappointed because I thought that couldn’t take it.
I returned to the hair brush handle, then a banana, lol. I then tried again, and after a while of pushing started to feel the head opening me up.
I was breathless but determined and I pushed back harder. All of a sudden, woosh, it flew up inside of me. God, I nearly fainted, lol, and jumped off it as fast as I could.
Once I had examined myself to make sure that I hadn’t done any ‘damage’ I resumed my position and tried again. This time, it felt better, and easier and once the head had squeezed itself inside me the rest followed quite easily and I began to ride the dildo for all it was worth, all the time, rubbing my cock through the stolen panties.
Heaven, but I wanted more!!!
It was almost dark outside! I had been to a couple of cottages before, close to where I lived then (Lancaster) but hadn’t done anything other than read the stories and messages written on the walls.
Now was my chance, and I wasn’t going to pass on it. Parents away, fully dressed, horny as hell and knowing that I could take a real cock.
I packed a bag full of male clothes and shoes in case I got stopped by the police or had to change quickly, peeped out of the curtains to make sure the neighbours weren’t around and sneaked out of the house to my car.
It was the first time that I had been out enfemme and the first thing that struck me was the coldness on my legs. It wasn’t winter, nut I just remember the chill of the night air against my skin as I walked out to the car.
I got in and pulled over my seat belt, noticing how it rested against my breasts, padded with balloons filled with water, lol. Oh how times have changed , he he.
I was wearing stilettos, and it felt really strange as I tried to reverse out of the drive. Once on the road, I found that I naturally sat differently, in a feminine way and drove in a completely different manner to normal.
I arrived at my destination (Caton, if you must know), and parked up. There was a car already there and I parked in a quiet corner, away from him.
After a while, he moved so he was next to me and got out.
I was shaking with fear and anticipation at my first experience. Thoughts raced through my head. What if he was an undercover copper? I needn’t have worried. He walked around my car, saw that I was enfemme then took out his cock. I would say that he was late 30’s or early 40’s, slightly chubby.
I hadn’t actually ever seen an erect cock before, lol and it was a surprise how big it looked!!!
I wound down my window and he came over, saying “Nice”, and, continuing playing with his cock, asked me what I was into.
Naively I suppose, I said “Anything really”.
He asked me if I fancied going somewhere quieter so I said ok and he told me to follow him.
We went up the road a bit and pulled into a very quiet and unlit layby.
He beckoned me to his car so I got out of mine and gingerly walked over to his, getting in the passenger side.
He had his cock in his hand and I didn’t need asking twice to suck it!!
It felt incredible. My first cock! I bobbed up and down on it and tasted how wonderful it was as he held onto the back of my head. He told me that I looked wonderful and that he loved TV’s and also that he hadn’t seen me around before.
I lifted myself off his cock and told him that it was my first time, before going back down on him again.
He asked me if I had ever been fucked and without lifting off his cock I shook my head. He then asked me if I would like to be fucked and I lifted off him again just long enough to say yes then resumed sucking.
He kept talking to me all the time, telling me how he was going to break me and that he would be gentle and that I was going to have my first cock in my pussy.
I was getting more and more turned on.
He pushed back his seat and asked me if I wanted to sit on his cock. I said “Yes”, and he took out a condom and started to put it on.
I re-arranged myself and managed to sit astride him, asking him to be gentle and to stop if I asked. He said he would and that he didn’t want my first time to be a bad experience and that he would just put it in a little bit then a bit more when I was ready. He also said not to worry about the pain, that at first it would most likely really hurt but then it would start to feel better, and also that there might be a little bit of blood the first time, as with all virgins, male or female.
I leaned back a bit until I felt his cock at my hole. God, it felt amazing already!!! He pushed up a bit so that his cock pushed against me and started to open me up. I was glad at this point that I had had plenty of practise and especially glad that I had taken the dildo earlier as his cock felt fucking enormous, bigger than the dildo and totally different.
He eased the end into me, all the time asking me if it felt ok. I could only nod and sigh breathlessly “Yes”.
I felt my pussy open up for him and eventually felt the widest part of his cock disappear inside me.
My mind was racing, my heart beating like a drum, as I held onto him. He started to thrust a bit, pushing himself into me more and more. Eventually, I realised that I was sat on his lap with his cock deep inside me.
He stopped and asked me if it felt ok. I told him that it was heaven. He then began thrusting in and out of me, slowly at first but getting faster. I moaned with pleasure at each thrust and had my arms tightly wrapped around his shoulders as I helped by bouncing up and down.
This is what I had wanted for so long. I felt like a girl, a real girl, bouncing up and down on a real cock, and having my virginity well and truly taken.
All the time he kept talking to me. Telling me what a good girl I was taking daddy’s cock, and how daddy was proud to take his little girl’s virginity and that soon I would have his cum inside of me.
I was in absolute heaven as I bobbed up and down on his cock, noticing the windows were all steamed up like they got when I shagged my girlfriend in the car. I felt like a slut, a real woman and so happy to be giving this man so much pleasure.
He told me that he was going to cum, and began thrusting harder and deeper then gripping me tightly, I felt his body stiffen as he let out a series of deep grunts and thrust into me with each one.
I stayed motionless on top of him for a while as we both recovered. He asked me if it was ok and as good as I expected and I told him “Better”, before climbing, shakily off him.
The condom slipped off his cock and was still inside me and I pulled it out, finding it to be full of cum, which was a relief as I at first thought it had come off and he had cum inside me!!! It was to be many years and with a trusted partner before I got my first proper filling, and I would have been mortified at that time if this stranger had cum inside me.
We arranged to meet again the week after but as my parents were back, I couldn’t get out and we didn’t meet again for about 10 years. He had forgotten who I was, lol. I was much, much more experienced but as I was sat on his cock and he was fucking me I told him that he was the guy hat took my virginity and reminded him. He was quite amazed at the woman I had become and fucked me even harder as I called him my daddy, lol, but that will be for another story, maybe.
Afterwards, I made my way back home, arriving back after midnight. I was so horny that after I had gone into the house, inspected my pussy, and re-done my make-up, I went for my first enfemme walk, down the street towards the railway crossing and back again, with each step becoming hornier, hearing my heels clicking on the pavement.
I can’t remember exactly what I did when I got back, but I’m sure that it involved fucking myself rigid with my stolen dildo!