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Caught dressing true story

By *adieTights OP TV/TS over a year ago

Doncaster

Like many I started crossdressing at a very young age, I was probably around 14 years old,been the youngest of 4 children, my parents had split up by the time I was 7 years old so mum fetched us up alone, so I never had much of a masculine influence in my life, my eldest brother had moved out by the time I was 12, so that left my at home with mum and 2 older sisters, I was very close to mum and I used to love chatting with her whilst she got ready for work, watching her apply her make up and selecting the clothes she was going to be wearing for the day, she worked in an office so she always dressed very smart and feminine, she always wore dresses or skirts always with tights and sometimes stockings, it was just innocent and natural to sit chatting whilst she dressed, one day she managed to ladder a pair of tights, so she put them in the bin, she went to work and I went to school, but a seed had been growing I’m head for a while now, I couldn’t help looking at women’s legs on the street, on the bus, in shops, if they were wearing nylons my eyes were drawn to them like a magnet, sitting there at school all I could think about was the tights my mum had put in the bin.

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By *mandajane01TV/TS over a year ago

Ballymena

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By *adieTights OP TV/TS over a year ago

Doncaster

Leaving school I rushed home safe in the knowledge I’d be home before everyone else, I got home and went straight to the bin and retrieved the tights, with my hormones going into overdrive I rushed to my bedroom, all I could think about was trying on those tights, so stripping off as quickly as I could I sat on the edge of the bed naked, I’d watched my mum getting ready for work as I’d said, I put on the tights imitating how she would draw the tights up her legs, I was still young so I was relatively hair free on my legs and body, I laid back on my bed, legs stretched out above me running my hands up and down my nylon clad legs, I was in heaven and i was seriously, I mean seriously hooked.

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By (user no longer on site) over a year ago

This is the way so many of us T girls started...dressing in our mother’s clothes! Good story - let’s hear more xx

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By *adieTights OP TV/TS over a year ago

Doncaster

The tights lasted me about a week, I even wore them to school under my uniform a couple of days, but this just wasn’t enough, my two sisters shared a bedroom, I’d go i there and go through there clothes on a weekend when they were out with friends and mum was out, I started to try on their panties and bra’s, short skirts and dresses, the high heels seemed impossibly high but it wouldn’t stop my tottering about in them like bambi, but alway, always I would be wearing tights and stockings, I was taking more risks stealing my sisters clothes and underwear, sitting there at the breakfast table trying to hide my shame when my sisters were arguing and accusing each other of stealing each other’s clothes. But I couldn’t help it, I had few friends and had no interest in sports so I spent a lot of time dressing en fem when ever I could. One hallowe’en my mum was going to a fancy dress, she dressed as Cher with a long black wig, I just new I had to have it once she was done with it.

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By *iving for todayMan over a year ago

stirling

More please

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By *orkiebar51Man over a year ago

Keighley

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By *adieTights OP TV/TS over a year ago

Doncaster

Not long after the party I was chatting to my mum and came up with the idea of telling her about a play that was been done at school and that some of the props, clothes and wigs where a bit crap, so I casually said that if she wasn’t going to be using that wig anymore could I give it to the school, she said yes, so that got hidden away with my ever growing stash of female attire, I’d sit watching mum apply her makeup trying to pick up tips along the way, asking her if it hurts when she applies eye liner, she’d turn to me and let me watch, I’m not sure if she had an idea of what was going on through my head, but she never questioned me when I would sit there watching her doing her makeup at every opportunity I could instead of been out with friends, again as soon as I got the house to my self I’d dress en fem, my newly acquired wig on and practice putting makeup on, walking more and more confidently in the high heels as time went on

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By *onsi69Man over a year ago

llanfairpg

Lovely

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By *adieTights OP TV/TS over a year ago

Doncaster

When I was sixteen I left school, I’d started to get a bit more hair on my legs ect, so I started shaving them, I got a job working with a friend of the family who was a plumber, he was in his fifties, he’d come and pick me up from home each day, I’d put dressing on hold for a while with working, but I could not let it go, I’d been working with the plumber who’s name is, let’s just say Joe, for about 8 months, he’d tease me, about asking girlfriend, asking why I didn’t have a girl yet, I’d just shrug it off laughing, trying to deflect his questions. One day after working about a year for him, he came to my house to pick me up earlier than he usually would, that wouldn’t be a problem, but I had gone to bed the night before wearing black stockings, suspender belt with matching knickers and bra, i heard the knock on the door, my mum answered it, then her shouting up to me that Joe was here early for me because he had an emergency job on, I was shocked, I didn’t know what to do, so I just grabbed my work trousers and t-shirt and jacket and got dressed putting my work socks over my stockings I put my work boots on and went down stairs. Getting into the van with him thinking to my self what have I done as we pulled away from my house.

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By *azKayeMan over a year ago

blackpool

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By *oodymonsterMan over a year ago

Near Shrewsbury

I started dressing in the same circumstances.

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By (user no longer on site) over a year ago

Now the horny part

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By *J GeminiTV/TS over a year ago

Northumberland

Liking the sound of this

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By *ini1275Man over a year ago

stoke on trent

Don't stop loving it xx

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By (user no longer on site) over a year ago

Who else wore mums clothes

Pm me

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By (user no longer on site) over a year ago

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By *adieTights OP TV/TS over a year ago

Doncaster

We arrived at the job we had to do a leaking hot water tank, the owners of the house were an elderly couple, they kept out the way, Joe was upstairs checking the job in hand whilst I was downstairs in the kitchen trying to turn the stop tap off, it was pretty much solid and i was struggling to turn it off, after about ten minutes of been on my knees with half me under the sink and my bottom half sticking out, i heard the kitchen door open, Joe walked in asking what was taking so long, but unbeknown to me my t-shirt and trousers had parted company and after I learned that my suspender belt and the top of my knickers were clearly on show, I turned around still not realising that I’d been flashing, only to see Joe with a big smile on his face, we completed the job later that same day, on the drive home Joe was unusually quite, on arrival at my house I was just about to get out when he said hang on I need to talk to you about something, I sat back, I was totally got smacked when he told me what he had seen and what would I have done if the customer had walked in instead, I must have been bright red with embarrassment, I just said I’m so sorry I jumped out of the van and ran straight into the house and up stairs to my bedroom, I lay on my bed crying my heart out thinking my life was over, but boy if I only knew what was to come next.

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By (user no longer on site) over a year ago

"We arrived at the job we had to do a leaking hot water tank, the owners of the house were an elderly couple, they kept out the way, Joe was upstairs checking the job in hand whilst I was downstairs in the kitchen trying to turn the stop tap off, it was pretty much solid and i was struggling to turn it off, after about ten minutes of been on my knees with half me under the sink and my bottom half sticking out, i heard the kitchen door open, Joe walked in asking what was taking so long, but unbeknown to me my t-shirt and trousers had parted company and after I learned that my suspender belt and the top of my knickers were clearly on show, I turned around still not realising that I’d been flashing, only to see Joe with a big smile on his face, we completed the job later that same day, on the drive home Joe was unusually quite, on arrival at my house I was just about to get out when he said hang on I need to talk to you about something, I sat back, I was totally got smacked when he told me what he had seen and what would I have done if the customer had walked in instead, I must have been bright red with embarrassment, I just said I’m so sorry I jumped out of the van and ran straight into the house and up stairs to my bedroom, I lay on my bed crying my heart out thinking my life was over, but boy if I only knew what was to come next."

Pm me Sadie

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By *imale38Man over a year ago

Barnsley

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By *adieTights OP TV/TS over a year ago

Doncaster

What was I going to do, the next morning I was dreading Joe turning up, i was still in bed when he came the next morning, hearing my mum answer the door and hearing mumbled chatter and laughing I was dreading what he may be saying to my mum, she shouted up to me, I opened my bedroom door and shouted down saying I didn’t feel well and wouldn’t be working today, after a while I heard his van leave and my mum popped her head around my door and asked if I was ok, on seeing I’d been crying she came and sat on my bed, I told her I’d had a bad night and now had a stinking head ache, I asked her what her and Joe had been talking about, she said he was just asking what I was up to this weekend, she told him she usually goes out most weekends with friends, he then inquired about my sisters and she told him that they were out or staying at there boyfriends most weekends, she stroked my forehead and said go back to sleep, Joe said don’t worry he would ring tomorrow to see if I was fit for work.

The following morning came it was a Friday, Joe usually pays my wages on a Friday, but I told my mum to tell him when he rings that I was still not well, a while later after hearing mum on the phone laughing , she came up to my bedroom again and told me Joe said not to worry he would pop my wages around on Saturday evening because he was busy at the moment, oh she said he’s going to give you something extra for working so hard over the last month.

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By *reeneyes1983Man over a year ago

Hyde

Love it...

I started to dress with mums tights too

Amazing

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By *ssex 2204Man over a year ago

billericay

Great story so far looking forward to year more

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By *adieTights OP TV/TS over a year ago

Doncaster

Saturday soon came around, I kept myself busy trying to keep my mind off of what had happened, it got to about 6.30pm when the phone rang, I had just been in the shower and was drying my self off in my bedroom, my sisters were out for the night and I knew mum wouldn’t be long before she was leaving to, I heard mum on the phone talking, only hearing her side of the conversation I could hear her saying she was going out with the girls on a hen do and wouldn’t be in till the early hours because they planned to go to this new club, she told Joe not to worry she would see him another day and that I was upstairs and feeling a lot better now, 5 minutes after hanging up she popped her head around the bedroom door to say she was going now and to say Joe was coming by with my wages I a while and to give me some news.

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By *ssexbjjaneTV/TS over a year ago

Brentwood

Lovely more please

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By *erry bull1Man over a year ago

doncaster

Nice story Sadie ,

Pm me

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By *dultfunscotland2000Man over a year ago

SW Scotland

Looking forward to this.

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By *ubsteffTV/TS over a year ago

Portsmouth

Liking where this is going

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By *adieTights OP TV/TS over a year ago

Doncaster

Mum shouted up my taxi is here, I see you tomorrow, oh and don’t forget to listen out for Joe, I’d slipped into a pair of old jogger bottoms and a t-shirt and was lying on my bed, 5 minutes after mum leaving I heard Joe’s van pull up outside, thinking to myself if I don’t go down stairs he’d post my wages thinking I’d gone out aswell, he knocked at the door for about 5 minutes, I crawled to the top of the stairs and could see him through the frosted glass, just post the damn wages I thought to my self, but no he kept knocking, he walked away and got in his van, the next thing the home phone was ringing, I looked through my mums bedroom window and could see him on his mobile, he was ringing the house, I was peeking through the gap in the curtains when he suddenly looked up, shit shit to late he had spotted me looking and was on his way back. He didn’t knock this time he opened the letter box and said stop playing silly beggers and let him in, I made my way down stairs and opened the door, smiling he said that’s better, I’ve been watching the house for the last hour waiting for my mum to go out, aren’t you going to invite me in. Standing back for him to pass, once in he said you better double lock that door

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By *adieTights OP TV/TS over a year ago

Doncaster

He walked into the living room and I did as I was told and double locked the door, on entering the room I found him sitting on the sofa, she said sit down patting the cushion beside him, I was lost as to what to do so I just did as I was told, he turned towards me in his seat and said are you feeling better now I nodded, sorry about getting on at you the other day, it wasn’t what you was wearing that bothered me it was the fact the customer could have seen me instead, I started to cry, don’t cry he said, you’ve got nothing to worry about, then he dropped the bomb shell, well nothing to worry about of you do as I say. Reaching over he took my hand and placed it on his now very erect cock, he tilted my head up looked into my eyes and said you better go change into something more sexy.

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By *exy-nurse-beckyTV/TS over a year ago

Doncaster

Mmmm I need to hear the ending. Of this

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By *adieTights OP TV/TS over a year ago

Doncaster

Shocked was the word for it, I just sat there with my hand trapped under his whilst he pressed my hand onto his hard cock, go on then go get sorted, I stood up and he smacked my bottom saying I’m going to enjoy this, my mind was racing as I walked up stairs, what had I done, I went into the bedroom and got my secret stash out, I heard him at the foot of the stairs saying he was just going to get something from the van, I looked through my gear thinking what should I wear, I was both frightened and excited but certainly leaning more towards excited, I choose to dress as sexy as I could, slipping my underwear on and securing my black stockings in place, slipping into one of my favourite little black dresses, putting on the Cher wig I then went into my mums room to use her makeup, I quickly applied the makeup and did something I’d not done before, I applied some perfume, I slipped into my high heels and looked at myself in the full length mirror, I must admit I was very pleased with how I looked, I don’t know why but I’d applied my makeup and everything better this time, I walked slowly down the stairs and into the living room, I looked wide eyed at Joe as he sat watching porn on the tv naked and playing with him self, looking over towards me he said fucking hell you look so fucking sexy dressed like that, he said stand in front of me and give me a twirl, I did as I was told my dress flaired when I twirled reviling my stocking top, he reached out and pulled me towards him, he’d gone out to the van to get a bag that contained vodka, and some other stuff, go get some glasses, he poured us a drink and told me to sit next to him, don’t be nervous he said, after a few more drinks I began to relax more, his hand came to rest on my stocking clad leg and he stroked me leg, he pulled my leg towards him making me turn in the seat, my stocking clad leg was in his lap I could feel his cock brushing my nylons, be it the drink or the porn we were watching I don’t know, but with out been told I took his erect cock in my hand.

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By *xLucyxx94TV/TS over a year ago

leeds

Mmm cant wait to hear what happens next xx

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By *adieTights OP TV/TS over a year ago

Doncaster

My head was swimming with alcohol and excitement, I slowly wanked his cock I knew what to do I’d wanked myself enough, I looked at him, he’d closed his eyes as I slowly wanked, watching my hand playing with another mans cock was so exciting and scary, I glanced at the tv screen and saw the women sucking the guys cock, God it made feel so horny, I looked at him with his eyes closed and then slowly lowered my mouth onto the tip of his cock, he moaned, I kept looking at the screen watching how it was done, turning back I kissed and licked the tip then parting my lips I took his cock into my mouth, his hand came and rested on the back of my head and encouraged me, wow this felt fantastic, I worked his shaft gagging now and again if I got carried away, wow your fantastic at that he said, he told me to kneel on the floor between his legs and carry on, I did as I was told and he used both his hands to cup my head as he face fucked me, I could taste his pre cum he was getting close.

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By *ssex 2204Man over a year ago

billericay

Absolutely wonderful story got me all horny

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By (user no longer on site) over a year ago

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By *elcdtvTV/TS over a year ago

Fareham

Great story xx

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By *everlyandersonTV/TS over a year ago

newcastle

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By *un Bi couple yorkshireCouple over a year ago

york thorganby

Very hot well written story xxx

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By *es for funMan over a year ago

port talbot

Love the way it's going mmm

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By *ust 58Man over a year ago

london

Going nicely , loving this

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By *ini1275Man over a year ago

stoke on trent

So hot love it

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By *orkiebar51Man over a year ago

Keighley

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By *ecretpantyTV/TS over a year ago

lisburn

So sexy

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By (user no longer on site) over a year ago

nice start looking forward too more

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By *orkshire biMan over a year ago

elland

Just how I started

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By (user no longer on site) over a year ago

Wow how horny

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By *atehantsTV/TS over a year ago

Petersfield

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By *urabriteMan over a year ago

stafford

Great story so many guys started out like this

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By *reedyannaTV/TS over a year ago

Swaffham

Mmmmm yummy

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By *ppetiteforsexMan over a year ago

Isle of Man

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By (user no longer on site) over a year ago

Great story

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By (user no longer on site) over a year ago

Brilliant the best is to come surly

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By (user no longer on site) over a year ago

Waiting for the next instalement

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By *aulaxd500TV/TS over a year ago

Wigan

Love it

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By *alecumguyMan over a year ago

Cowbridge

A cracking read, can't wait for some more

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By (user no longer on site) over a year ago

you started dressing the same way I did

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By *allyCD123TV/TS over a year ago

Wexford

Great story Sadie waiting on the final instalment sound like it’ll be yummy

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By *helsea_PowellTV/TS over a year ago

Bradford

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By *dsindyTV/TS over a year ago

East Lancashire

Hot, got me hard in my knickers. Need to release now.

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By *oodtimebiboyMan over a year ago

bristol

What an erotic experience, thanks for sharing

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By *adieTights OP TV/TS over a year ago

Doncaster

Wow this was a new experience for me and I must admit he felt and tasted pretty good in my mouth, I thought to myself I must be doing something right because he was rock hard, looking up he still had his eyes closed and was morning with pleasure. You better stop or I’m going to cum he said tilting my head up, he took my hand and pulled me back on to the sofa next to him, looking at me he asked if I had done that before because I certainly seemed to know what I was doing, no I replied shyly I was copying the women on the porn film, he made us another vodka and we sat watching the porno, he had pulled my stockings clad leg into his lap and was stroking my leg, he put his arm around me and pulled me into his body, my brain was swimming with alcohol and watching the the women been fucked on the film was turning me on so much. Making my excuses I made my way to the toilet, on my return he had paused the film at the point were the women was riding the guys cock. Looking up at me he told me to come and straddle him like the women on the film, I said I wasn’t sure I can do that, it wasn’t a question he said, you can choose to do as I tell you or try and explain what you did at work after I tell your mum why I had to sack you. He had given me an ultimatum, I walked over to him, as I did so he produced some lube, after he lubed his cock up he told me to remove my knickers and turn around, I did as I was told, him working the Lube into my pussy with his finger felt good to be honest, turning my back around he pulled me on to his lap, I could feel the tip of his cock pressing against my pussy, he gripped my hips he gently pushed is cock inside me, the pain was was unbelievable, my eyes welled up with tears but he held me in place, after a short while the pain subsided, are you ok he asked I nobbed through my tears thinking do I have a choice, he started to work his cock further into me, I’d like to say I wasn’t enjoying the feeling but the fact I was starting to meet his thrusts said different, the feeling of him taking my cherry was turning me on, I’ve always been short height wise and never weighed much so when he held onto me and turned me onto my back it was no surprise how easy he did it, he climbed between my stocking clad thighs, reaching for the lube he greased me up again before placing my legs upon his shoulders, he was having trouble hitting the mark so I guided him in side me, feeling his shaft between my fingers disappearing inside me felt fantastic, all I could feel were his balls pressing against me, I let a little squeal of pleasure out, you like that don’t you he said, mmmmm I said I do, this encouraged him more, pushing his feet into the sofa arm for purchase he started to fuck me deep and hard, I don’t know what felt better the feeling of his balls slapping against me with every thrust or the sound of it, I had my eyes closed now and I was gripping his hips to help his thrusts, his breathing was becoming more and more laboured, the feeling of is balls slapping against me felt fantastic, but the feeling of his seed exploding inside me took it to an whole new level, he laid his body aginst mine and we laid like that for a while catching our breath, his hot breath on my neck, I’d wrapped my legs around his back now not wanting to miss a single pulse as he emptied his cum into me. After a while he made his excuses to leave, I was in bed still dressed in my underwear and stockings when I heard my mum arrive home, laying there with his seed dribbling out of me most of the night I knew then that this was just the start of my new life.

Thank you for reading and your comments. Hope you have enjoyed this true story and I do mean true, just let me know if you want to know what else happened.

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By *erry bull1Man over a year ago

doncaster

"Wow this was a new experience for me and I must admit he felt and tasted pretty good in my mouth, I thought to myself I must be doing something right because he was rock hard, looking up he still had his eyes closed and was morning with pleasure. You better stop or I’m going to cum he said tilting my head up, he took my hand and pulled me back on to the sofa next to him, looking at me he asked if I had done that before because I certainly seemed to know what I was doing, no I replied shyly I was copying the women on the porn film, he made us another vodka and we sat watching the porno, he had pulled my stockings clad leg into his lap and was stroking my leg, he put his arm around me and pulled me into his body, my brain was swimming with alcohol and watching the the women been fucked on the film was turning me on so much. Making my excuses I made my way to the toilet, on my return he had paused the film at the point were the women was riding the guys cock. Looking up at me he told me to come and straddle him like the women on the film, I said I wasn’t sure I can do that, it wasn’t a question he said, you can choose to do as I tell you or try and explain what you did at work after I tell your mum why I had to sack you. He had given me an ultimatum, I walked over to him, as I did so he produced some lube, after he lubed his cock up he told me to remove my knickers and turn around, I did as I was told, him working the Lube into my pussy with his finger felt good to be honest, turning my back around he pulled me on to his lap, I could feel the tip of his cock pressing against my pussy, he gripped my hips he gently pushed is cock inside me, the pain was was unbelievable, my eyes welled up with tears but he held me in place, after a short while the pain subsided, are you ok he asked I nobbed through my tears thinking do I have a choice, he started to work his cock further into me, I’d like to say I wasn’t enjoying the feeling but the fact I was starting to meet his thrusts said different, the feeling of him taking my cherry was turning me on, I’ve always been short height wise and never weighed much so when he held onto me and turned me onto my back it was no surprise how easy he did it, he climbed between my stocking clad thighs, reaching for the lube he greased me up again before placing my legs upon his shoulders, he was having trouble hitting the mark so I guided him in side me, feeling his shaft between my fingers disappearing inside me felt fantastic, all I could feel were his balls pressing against me, I let a little squeal of pleasure out, you like that don’t you he said, mmmmm I said I do, this encouraged him more, pushing his feet into the sofa arm for purchase he started to fuck me deep and hard, I don’t know what felt better the feeling of his balls slapping against me with every thrust or the sound of it, I had my eyes closed now and I was gripping his hips to help his thrusts, his breathing was becoming more and more laboured, the feeling of is balls slapping against me felt fantastic, but the feeling of his seed exploding inside me took it to an whole new level, he laid his body aginst mine and we laid like that for a while catching our breath, his hot breath on my neck, I’d wrapped my legs around his back now not wanting to miss a single pulse as he emptied his cum into me. After a while he made his excuses to leave, I was in bed still dressed in my underwear and stockings when I heard my mum arrive home, laying there with his seed dribbling out of me most of the night I knew then that this was just the start of my new life.

Thank you for reading and your comments. Hope you have enjoyed this true story and I do mean true, just let me know if you want to know what else happened."
nice story

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By *aughty grease monkeyMan over a year ago

Coventry

Great story lucky slut xxx

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By (user no longer on site) over a year ago

How I miss cock during covid...

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By *issy vickiTV/TS over a year ago

lisburn

Yes please

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By (user no longer on site) over a year ago

Yes please don’t stop there

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By *mfao88Man over a year ago

north yorkshire

Yes keep going please

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By *amup4fun80TV/TS over a year ago

Southend on Sea (Benfleet)

Love this. So exciting

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By *iving for todayMan over a year ago

stirling

More please

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By *asmin999jmTV/TS over a year ago

wakefield

Amazing story Sadie xx do tell more

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By *dsindyTV/TS over a year ago

East Lancashire

Ahhhhhhh, the release. New knickers required

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By *aulaxd500TV/TS over a year ago

Wigan

More please x

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By *usanne9537TV/TS over a year ago

Nottingham

Please keep going I’m really enjoying this xx

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By *onsi69Man over a year ago

llanfairpg

Yes please

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By *w79Man over a year ago

Stalbridge

Wow such a hot Post.

Had me almost cumming in my boxers

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By *ust 58Man over a year ago

london

Phew , what a finale , great detail hard as rock , thanks for a great ride .

Love to hear more please

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By *illycd2TV/TS over a year ago

Bishop's Stortford

I really enjoyed your story and it being true make it so hot, Please don't stop like to hear more. Thank you

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By *adieTights OP TV/TS over a year ago

Doncaster

Thank you for the great comments everyone and the wonderful messages I’ve been receiving.

Please keep a look out for me sharing my experiences, because certainly been in this lock down it has made me think more about my younger days xxx

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By (user no longer on site) over a year ago

please do share

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By *umblebiMan over a year ago

ayles

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By *ubsteffTV/TS over a year ago

Portsmouth

I’d love to hear more about what happened afterwards.

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By *ikeC2012Man over a year ago

Peterborough

A fabulous story!

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By *ndrea54TV/TS over a year ago

cambridge

A lovely story Sadie

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By *aulnorthumberlandMan over a year ago

Blyth

Being true makes it sooo hot

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By *nly1meMan over a year ago

here there n everywhere

Omg wot a read..wish u worked 4 me then hehe loved reading that...ive always fantasied about working at someones house and then they came out dressed up yummy.

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