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Losing my virginity to a shemale.
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This story is all based on a true event recently which I thought id share with you.
A little back story from my time on this site and other sites..I've always had a thing for nylon growing up it was a huge turn on and my first experience of wanking was with a pair of tights as a young horny teenager growing up (what a night!)
This led to me searching for more everytime,but i wasn't sure what I was searching for.
I've always been with females growing up but my horny teenage side didn't let up and I browsed many sites and finally found my way to this one.
Being young and slim I had my fair share of meeting older ladies which gave me some great experiences..
They loved to dress amazing and smell amazing and show a you a good time.
One night though I come across a cross dresser and I thought I'm young why not and that took me down this journey!
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I met a few crossdressers,men in nylons and the like..mainly being the top but again more urges came and I wanted more.
I started to wank and suck and explore that side of the sexual meets which then it started to become a disappointment if they didn't want any of that in return.
It narrowed down who I could meet to help fill them urges.
I tried to suppress these urges over the years growing up,family settling down,covid and personal reasons but I kept returning and this is where it really begins... |
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Thoughts running through my head I'm ready to lose my virginity but it needs to be right.
I went searching and it's very hard to find tops/vers girls on here.i even went down the route to find a lady who pegs.(my God that's like finding the end of a rainbow!)
I was browsing and up popped nycolle,
Beautiful leggy shemale top long black hair beautiful red lips.
We get chatting and I explained this is what I'm looking for but it's my first time I want it to be right!
She was very understanding and quite bossy which turned me on a little.
We exchanged dates that worked for us both and how it would go down,but as we all know it never does go to plan lol.
Finally the day arrives... |
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So ive parked up at there apartment,
Very nervous I've text and they've said to come up.
Buzzed myself in and get the lift to the door,as the doors on the lift open my heart goes and I'm here no turning back..
As ive knocked this beautiful goddess has answered the door,beautiful white smiley teeth,red lipstick and some amazing latex outfit with nylons poking out at the bottom leading to a very high heel.
"Hey baby" with that she pulled me in and kissed me passionately.
Wow I was left mouth wide open and lost for words..she pulls me inside with a laugh and she kisses me again as the door closes and leads me into the kitchen to get us a drink.
We sat down and was having small talk and she says right "I'll lead the way,follow my lead and do as I say" with a wink and cheeky smile.
Do as I say?I thought but before I could say anything she pulled me in for another deep kiss and stood up and led me to the front room.. |
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We sat on the sofa kissing passionately,it felt amazing and I didnt want it to stop,but as she pulled away she stood up and said "so do you like my outfit" i could barely get any words out and my head slowly nodding she laughed and said I take that as a yes with a wink as she stroked the outline of her cock.it looked bigger than I thought it was.
She unzipped part of this latex suit and it released a good 7.5-8 inch's I'd say but girthy...Fuck!
But before I could think to much my head was pulled forward and it was sliding into my watery mouth.
In and out at first but with a rhythm to it.
I've sucked before and never had complaints and by her moans and calling me baby I knew I was doing well.
This went on for a few minutes and she pulled it out and laughed..
"Let's go upstairs baby" she said and I got up from the sofa and she led me by the hand.
As we was walking i said to her I'm not sure If im going to be able to handle that!
She turned to me half way up the stairs and said "do you trust me"
I hardly know you I thought but her twinkle in her eye and her sweet voice i nodded and carried on letting her lead me up to her bedroom |
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We walk into the room and she closes the door,we begin passionately kissing again and our hands all over eachother I just cant get enough!
I've never been so hard in my life and she noticed and smiled at me,she took my top off and began kissing me down my neck and across my chest and stomach..she slowly lowered my joggers and then my boxers.with that my cock sprung out,
Not as big as this beauty infront of me,average size fat and I can cum for England haha.
She said "mmmm hello soldier" laughing as my cock stood to full attention!
She began teasing me,licking my balls kissing the tip me begging her to suck it,but she ignored me and brushed my hand away,resting the tip on her lips she looked up and proceeded to take it all down to the balls which sent me to ecstasy.she slowly pulled it out and grabbed the back of my legs firmly taking it back down deep up and down,down and up faster and faster..my legs turned to jelly I couldn't hold myself up properly and as she come up again I fell back onto the bed hands on my head exhausted from one of the best bjs I've had,
She stood up walked off to her draw and got something but in my daze I didn't see what it was.it was a blindfold and she put it on me and then she got down again on her knees and split my legs apart and began licking my arse which felt amazing..she stops and I hear a click and a squirt which was cold,
It was lube I didn't know what was going on I wasn't ready for this!
I reacted and sat up not seeing anything,she said baby trust me and kissed me pushing me back on the bed,
Then I felt something push against my arse and then it entered me...a little hurt but I thought this isn't bad what was the fuss and with that she said right wait here..I was confused wait here?your inside me and I said this to her...she replied "no baby that's just a butt plug wait here I'm going to change into something more comfortable..
So here I was blindfolded with a butt plug up me and my queen has walked out the room... |
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I was laying there on the bed butt plug in,blindfold on and legs spread.
Im so confused,nervous and anxious,it feels like she's left me here for ages (probably 5 mins) then I hear a clip clop across the hall to the door and it opens.
I sit up on the edge of the bed not knowing what or who was standing infront of me,then I hear nycolles voice"baby are you ready to explore a new world of fun with me?"yes!I said "do you trust me?" Again I reply yes!but not sure how I really felt if I'm honest.."right now you will follow my lead and do as I tell you ok?"yes I reply..
"Now stand up and take that mask off"
I slowly moved the eye mask up ready to see what was or who was infront of me..I know it's nycolle but she went away for a few minutes and come back without me seeing I'm nervous as hell now but I'm here I can't escape I'm naked with a butt plug in my arse and a massive hard on |
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"I was laying there on the bed butt plug in,blindfold on and legs spread.
Im so confused,nervous and anxious,it feels like she's left me here for ages (probably 5 mins) then I hear a clip clop across the hall to the door and it opens.
I sit up on the edge of the bed not knowing what or who was standing infront of me,then I hear nycolles voice"baby are you ready to explore a new world of fun with me?"yes!I said "do you trust me?" Again I reply yes!but not sure how I really felt if I'm honest.."right now you will follow my lead and do as I tell you ok?"yes I reply..
"Now stand up and take that mask off"
I slowly moved the eye mask up ready to see what was or who was infront of me..I know it's nycolle but she went away for a few minutes and come back without me seeing I'm nervous as hell now but I'm here I can't escape I'm naked with a butt plug in my arse and a massive hard on"
Ready for more |
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As I removed the mask I see nycolle standing there,she remembered I had said nylons were my ultimate weakness and here she was standing in a oily black nylon bodystocking with a cut out at the front with her cock standing to attention and some amazing knee high boots.
"WOW" is all I could manage to get out of my mouth,she smiled and said "I remembered and wanted you to have the best experience"
I thanked her but before I could say anything else she switched,
"Get on the floor!"I sprung into life and did as she said butt naked on my knees on the floor still with the butt plug up me.
She walked across the room to the left and sat in a single chair she had in the room legs spread and told me to crawl over to her at her feet..
As im crawling across the carpet im thinking to myself I'm just a normal alpha guy who loves a beer,playing football etc and here I am naked butt plug in crawling across a floor to not upset this super hot shemale!
As I reach her right by her boots she lifts my chin up so I'm making complete eye contact.
"You are now my toy you will do what I want when I want you get understand?" As I nod she gives me a little slap to my cheek and tells me to slowly remove her boots,
As I removed the first one she pushes her foot against my super hard cock and slowly runs it up my chest.
"Worship my feet baby"
I slowly began to lick,kiss and suck her toes and feet and by the moans I was doing well,I repeated this with the other foot and she had me work my way up her legs kissing and licking as I went up until I met the top of her cock.
"Suck it boy,slowly!" This is really turning me on and I do as im told slowly working my way down her big helmet up and down down and up,i start to pick up a rhythm but not fully taking it all down as its big for me.
Im told to rest my hands on her legs and go hands free which I did and then I feel her hands grab the back of my head forcing me down further everytime I went down on her,i coughed a few times but this didn't stop her keeping me going down further and further,she said you will get used to it keep with it.
And then I felt her Guidance get a bit quicker and quicker and then she just held my head rose from her seat and was fucking my mouth!i could hardly catch my breath it was so intense saliva pouring from me,my eyes watering!her balls slapping against my face everytime bang bang bang!
She suddenly stopped pulled my head away and I fell back on the floor trying to gather my breath,she was standing over me laughing
"You enjoy that baby you did really well"
I blurted out something that resembled yes.
"Come on we've only just got started she said |
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