The Ballad of Wrangler Jane
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Holly...How It All Began With Jane free porn video
All things start somewhere...although some things start before others...
I read that somewhere and have to agree it's true...especially regarding the feminine side of me that was,and still is, Holly. Although back then...as a teenager...Holly didn't exist....just a very horny,hormone fuelled male me that was in lust with my first girlfriend called Jane....and it's her fault why all these years later I still get such a sexy kick out of wearing fem clothes and enjoying the female side of me...
You see..I didn't get into crossdressing by what you would call the "traditional" way (ie: discovering a female family members things and giving into curiosity and temptation). Nope. It was my 16 year old girlfriend and her experimental attitude to sex that opened my eyes to the feel of lacy lingerie,little skirts and stockings and school uniforms that opened my eyes to a whole new world of sensual adventure and downright kinkiness...Here's the true story of the very first time....
Now me and Jane had become an item over mutual love of heavy metal music during sixth form college (which kind of dates me a bit,right..? Lol). She was an average looking girl with blonde hair and blue eyes but I found her really attractive....and besides I've never been what you would call a looker...see my face pics here for proof..lol. What really twisted my head was her appetite for sex. I don't mind admitting at that point,aged 16 myself, I'd never had sex, although all us teenage boys did the usual bullshitting, and I'd had previous girlfriends with which I had indulged in some seriously heavy petting which had given me some of the worst cases of blue balls in my life. But Jane was different. She knew about sex and what she wanted was my cock inside her...mouth or pussy..she really was a bit of the archetypal sixth form nympho girl. I never stopped to wonder where she got it from but just revelled in the glory of fucking her whenever she wanted it... and believe me....she wanted it a lot! ;-)
We'd fuck ourselves silly at break times during college out in nearby fields. Then back to my place...or more often hers as her parents were out working until early evening and we'd spend hours sucking and fucking,wandering naked around her house and doing it in all the main rooms... (but never her parents room). She particular like me to fuck her in the living room near the huge window facing the street outside...which was residential, not a particularly busy road, but it was a turn on as much for me, as well as her to pound her pussy or have her sucking my rock hard teenage cock right in front of that window....I guess we matched as exhibitionist types too but we didn't really understand that then...only the thought of being seen by someone added to the sense of explicit and complete passion we shared.
And it was one of these early evenings after we had stripped off together,she looked at me with what I can only call pure devilment in her sparkling blue eyes, when she reached down,picked up her lacy white panties and said "Put these on for me". Well, it was the two of us. No one else about. I didn't see any harm in it....and of course, back then there were no phones us teenagers had to perpetrate sexual blackmail on each other. Lol. "Ok" I said....and took them from her and pulled them up my long legs and over my already once spent cock...
Now,regardless of how horny your average teenage boy is with his hot and sexually willing girlfriend,as her panties went tight around my cock and balls I felt a thrill I had never felt before. This felt extremely wrong but somehow perfectly right and my cock literally stood up straight out,stretching Jane's panties which made her giggle in such a sexy way, that I groaned out loud."Feel nice do they?" she asked. "Oh yes" I moaned,completely without self conscious thought. She strutted over to me naked...her hot firm teenage body so ripe...and her matching lacy white bra dangling from one hand. She started to stroke my hard cock through her panties that felt to me at least a foot long and ready to burst, and in that same low sexy voice she said..."Now put my bra on too...you'll look even sexier hon".
I couldn't deny that voice and the way I was feeling and she helped me put it on clipping it at the back and adjusting the straps. Now Jane wasn't a particular over endowed girl in the breasts department but there was still an amount of space between the cups and my own chest. She said, "Wait a second" and nimble and naked left the room at speed to go to her bedroom,returning with a couple of pairs of her socks which she tucked into the cups of her bra to give me my first "boobs". She took a step back admiringly and purred "Ohhhhh yesssss" and reached down between her legs and started rubbing her pussy right in front of me...oh gods....I wanted her so badly right then. I went to wrap my arms around her and get close and hot but she said "No...turn around for me". I did. "Mmmmmmm" she murmmured. "You have a great arse too hon. Bend over and touch your toes for me". I was completely lost at that point. If she'd have asked me to stick my cock in the fireplace in that room and fuck it for her whilst it was on full heat I'd have done it. I bent over,sticking my arse out in her little white lacy panties feeling absurdly exposed and absolutely horny as hell. "Spread your legs a bit", she said. I did. It was then she came up behind me and bought her hand down sharply on my left arse cheek. I yelped,more in shock than pain."You're a dirty little bitch,aren't you?" was all she said to that. "Yes." Was all I could manage."I bet you're a dirty little bitch who likes to eat pussy,aren't you...?"
"Oh yes,Miss" I moaned, wondering where the hell the "Miss" had come from and what the fuck was happening to me....and please...please could I fuck her and fill her with my cum....but Jane had another idea. She grabbed me by my long rocker hair (heavy metal fan remember...?) and dragged me over to the armchair right in front of that big living room window. She sat down and spread her legs,pushing me back onto the floor almost snarling..."Eat my pussy you dirty bitch!". Like I had a choice...? I got down between her legs,tonguing her wet teenage cunt and that horny bitch literally fucked my face and mouth,pulling my hair and trapping me down there grinding her twat right onto my tongue and mouth so that I could hardly breathe....but I just didn't care...she was screaming and moaning like she was possessed and it was at that point that my cock just exploded into her panties. I wasn't even expecting. I nearly passed out but Jane's flood of pussy juice just keep me aware. Never in my life had I had an orgasm like that...and I'm not entirely sure she had either.
I came up,my face absolutely covered in her juice...and some of her piss too I think...she really had let go...and she pulled me up and kissed me so wonderfully and passionately...I think that was the point where teenage lust for her became teenage love...as transient as teenage love maybe. We curled up in that armchair in front of that big plate glass window, her naked,me in her bra and panties with her socks stuffed into the bra and the sun setting on our hot and tingling teenaged bodies and I whispered "Can we do that again,sometime babe. That was amazing". She kissed me again on the lips and with the same devilish look in her eye when she handed me her panties she said " Sure...but perhaps we can find some other things of mine you can wear next time......"
The End......for now
I read that somewhere and have to agree it's true...especially regarding the feminine side of me that was,and still is, Holly. Although back then...as a teenager...Holly didn't exist....just a very horny,hormone fuelled male me that was in lust with my first girlfriend called Jane....and it's her fault why all these years later I still get such a sexy kick out of wearing fem clothes and enjoying the female side of me...
You see..I didn't get into crossdressing by what you would call the "traditional" way (ie: discovering a female family members things and giving into curiosity and temptation). Nope. It was my 16 year old girlfriend and her experimental attitude to sex that opened my eyes to the feel of lacy lingerie,little skirts and stockings and school uniforms that opened my eyes to a whole new world of sensual adventure and downright kinkiness...Here's the true story of the very first time....
Now me and Jane had become an item over mutual love of heavy metal music during sixth form college (which kind of dates me a bit,right..? Lol). She was an average looking girl with blonde hair and blue eyes but I found her really attractive....and besides I've never been what you would call a looker...see my face pics here for proof..lol. What really twisted my head was her appetite for sex. I don't mind admitting at that point,aged 16 myself, I'd never had sex, although all us teenage boys did the usual bullshitting, and I'd had previous girlfriends with which I had indulged in some seriously heavy petting which had given me some of the worst cases of blue balls in my life. But Jane was different. She knew about sex and what she wanted was my cock inside her...mouth or pussy..she really was a bit of the archetypal sixth form nympho girl. I never stopped to wonder where she got it from but just revelled in the glory of fucking her whenever she wanted it... and believe me....she wanted it a lot! ;-)
We'd fuck ourselves silly at break times during college out in nearby fields. Then back to my place...or more often hers as her parents were out working until early evening and we'd spend hours sucking and fucking,wandering naked around her house and doing it in all the main rooms... (but never her parents room). She particular like me to fuck her in the living room near the huge window facing the street outside...which was residential, not a particularly busy road, but it was a turn on as much for me, as well as her to pound her pussy or have her sucking my rock hard teenage cock right in front of that window....I guess we matched as exhibitionist types too but we didn't really understand that then...only the thought of being seen by someone added to the sense of explicit and complete passion we shared.
And it was one of these early evenings after we had stripped off together,she looked at me with what I can only call pure devilment in her sparkling blue eyes, when she reached down,picked up her lacy white panties and said "Put these on for me". Well, it was the two of us. No one else about. I didn't see any harm in it....and of course, back then there were no phones us teenagers had to perpetrate sexual blackmail on each other. Lol. "Ok" I said....and took them from her and pulled them up my long legs and over my already once spent cock...
Now,regardless of how horny your average teenage boy is with his hot and sexually willing girlfriend,as her panties went tight around my cock and balls I felt a thrill I had never felt before. This felt extremely wrong but somehow perfectly right and my cock literally stood up straight out,stretching Jane's panties which made her giggle in such a sexy way, that I groaned out loud."Feel nice do they?" she asked. "Oh yes" I moaned,completely without self conscious thought. She strutted over to me naked...her hot firm teenage body so ripe...and her matching lacy white bra dangling from one hand. She started to stroke my hard cock through her panties that felt to me at least a foot long and ready to burst, and in that same low sexy voice she said..."Now put my bra on too...you'll look even sexier hon".
I couldn't deny that voice and the way I was feeling and she helped me put it on clipping it at the back and adjusting the straps. Now Jane wasn't a particular over endowed girl in the breasts department but there was still an amount of space between the cups and my own chest. She said, "Wait a second" and nimble and naked left the room at speed to go to her bedroom,returning with a couple of pairs of her socks which she tucked into the cups of her bra to give me my first "boobs". She took a step back admiringly and purred "Ohhhhh yesssss" and reached down between her legs and started rubbing her pussy right in front of me...oh gods....I wanted her so badly right then. I went to wrap my arms around her and get close and hot but she said "No...turn around for me". I did. "Mmmmmmm" she murmmured. "You have a great arse too hon. Bend over and touch your toes for me". I was completely lost at that point. If she'd have asked me to stick my cock in the fireplace in that room and fuck it for her whilst it was on full heat I'd have done it. I bent over,sticking my arse out in her little white lacy panties feeling absurdly exposed and absolutely horny as hell. "Spread your legs a bit", she said. I did. It was then she came up behind me and bought her hand down sharply on my left arse cheek. I yelped,more in shock than pain."You're a dirty little bitch,aren't you?" was all she said to that. "Yes." Was all I could manage."I bet you're a dirty little bitch who likes to eat pussy,aren't you...?"
"Oh yes,Miss" I moaned, wondering where the hell the "Miss" had come from and what the fuck was happening to me....and please...please could I fuck her and fill her with my cum....but Jane had another idea. She grabbed me by my long rocker hair (heavy metal fan remember...?) and dragged me over to the armchair right in front of that big living room window. She sat down and spread her legs,pushing me back onto the floor almost snarling..."Eat my pussy you dirty bitch!". Like I had a choice...? I got down between her legs,tonguing her wet teenage cunt and that horny bitch literally fucked my face and mouth,pulling my hair and trapping me down there grinding her twat right onto my tongue and mouth so that I could hardly breathe....but I just didn't care...she was screaming and moaning like she was possessed and it was at that point that my cock just exploded into her panties. I wasn't even expecting. I nearly passed out but Jane's flood of pussy juice just keep me aware. Never in my life had I had an orgasm like that...and I'm not entirely sure she had either.
I came up,my face absolutely covered in her juice...and some of her piss too I think...she really had let go...and she pulled me up and kissed me so wonderfully and passionately...I think that was the point where teenage lust for her became teenage love...as transient as teenage love maybe. We curled up in that armchair in front of that big plate glass window, her naked,me in her bra and panties with her socks stuffed into the bra and the sun setting on our hot and tingling teenaged bodies and I whispered "Can we do that again,sometime babe. That was amazing". She kissed me again on the lips and with the same devilish look in her eye when she handed me her panties she said " Sure...but perhaps we can find some other things of mine you can wear next time......"
The End......for now
Aspen
- 17.10.2021
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