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Well I felt stupid but also a little suprised at how I loved the feel of the clothes I was wearing..
I was 16 it was 1981 here I was dressed as a naughty school girl.. My sister Sarah and an older family friend had dressed me up to go to a fancy dress party in a posh hotel, I was involved in charity work for disabled
people and this year one of our sponsors really pushed the boat out for us and then invited us to there Xmas celebrations.
I was at the time 5,4 and had a swimmers build, slim and trim due to my daily workouts. I had gone from a fat kid to slim trim teenager and I loved showing off my new look..
But this was def a new sensation being dressed in girls clothes.. A had shoulder length auburn hair my sister had teased into bunches.. Full make up, my legs had hardly any body hair so after a few glasses of wine she had convinced me to shave down below.. The feeling of stockings when I pulled them on my naked silky legs and attaching them to the straps on the tight silky control panties my sister had given me…
My cock started to get a chubby on. I had to very quickly excuse myself and run to the toilet.. In the bathroom mirror I could see a sexy young girl.. My cock was straining to be released..
I rolled down the tight pants.. Sat on the toilet and started to wank my 5 inch cock as I stroked the top of my thighs.. I grabbed a wad of tissue and stuck my cock head in and a soon cumming filling it my cock slowly started to deflate and after wiping it clean I was finally able to get it back inside the pants and get back to my sister and friend
Feeling better now she smiled at me then giggled…. Here put this on. I was handed a white cotton school blouse which felt a little tight.. Then she had me pull on a school girl pinafore that finnshed just below my knickers and you Could see the top of my stockings..
Wow its a good job you have nice legs.. As she did this she stroked one hand down them.. My cock started to twitch in my tight pants and I had to step away. And into a pair of borrowed heels.. I was only a size 5 so my sister had found it fairly easy to find me a pair..to borrow
Weirdly I felt right at home in them maybe it was my balance from all the workouts and yoga.. And walking was easy for me.. I borrowed a small hand bag for some money and lippstick a long black coat.completed my outfit .I was ready..
My mum called from downstairs your ride is here.. Come on he’s waiting..
One of the directors who,s company sponsored our events lived in the same village as me and had offered to take me to the hotel..
He had a beautiful old rover p5b coupe it idled by the side of the road… As I clicked down the front path, my legs suddenly felt the cold and for the first time I realised what girls go through to look good..
I went to open the back door. And he called get it the front my wife isn’t coming she’s not very well..
I scooted round and he opened the door from the inside, the interior was very hot and inviting the long leather seats formed a bench.. I had met Steven once or twice before.. He was a big tall guy ex rugby player in his 50,s with a crooked nose and dark curly hair, Allways happy and smiling.. He was dressed in a very nice shirt and tie… As I settled in I asked why he wasn’t in fancy dress… He told me all will be revealed later..
He was looking at me his mouth dropped a little.. Wow you look amazing just a younger version of your beautiful sister.. I took this as compliment as my sister was a hot looking girl at 19..and I think I actually blushed a little.. As we drove off into the dark night.. Through the country lanes towards the hotel.. I had to shrug the coat off as it was so warm with the tight blouse and pinafore..
I pulled the coat away and placed it next to me..
The feeling of leather on my legs and stocking not to mention my panty clad ass was something new and it felt very sexy… I was trying not to get a hard on.. The pinafore didn’t cover my stocking tops and I could see Steve look down at my slim legs..
I take it St trinians was your role model for the outfit..
Yes I’ve allways fancied the girls in there outfits.. I just didn’t think I would become one..
Steve.. Said yes they have always been a favourite of mine as well..
We arrived at the hotel and Steven actually jumped out and said allow me… He opened the door and I swung my legs out.. I could feel him watching my legs as the came into view and he took my hand as I placed my feet on the gravel.. My first wobbly bit as I tried to stand up straight and he caught me in his arms.. His arm around me holding me tight.. Even with heels on I was at his shoulder hieght.. And I could feel his still hard body against me…. His eyes looked down on me are you OK Sarah he asked… I’m not Sarah… I’m Tom… I giggled holding onto him for support..
I think you should pretend to be your sister then you would get drinks from the open bar.. I thought about this for one split second free booze!! Your on I said.. Grinning to myself free booze.. Wow.. He reached past me and grabbed Something from the back seat
My costume… He donned a long black cloak and a mortor board.. And then reached again and brought out a long thin cane… He swished it through the air.. Next to me.. You better be on your best behavior tonight Sarah or I may have to spank you..
Yes Sir I promise to be good. I said this in my best girly voice which really that far from my own still annoyingly girly voice.. I could see he reacted to the sir and he smiled
Your sister told me about your costume in the pub, so I thought we could go the whole way.
I took his arm and said lead on Sir time to enjoy the night and I’m freezing out here.. My cock and balls had shrivelled to virtually nothing in my pants.. And my legs where really cold the tops I’m sure where starting to turn blue..
We walked laughing into the hotel.. Then into the ball room it was already full of people..
Lots of people did double takes as they saw us walk in together.. I could see the confusion on people’s faces as I introduced myself as Sarah for the night..
My best friend Carl came up to me and said wow you really do look like her.. Can you snag us drinks you think…
I turned to Steve but he had already shot off to mingle.. My friend Richard was dressed as a clown and looked great it suited his personality..
You stay here ill try and get us drinks… I walked to the bar wormed my way through the throng of heaving bodies and leant over.. Trying to catch the barmans eye.. Unbeknown to me my pants where on show and so where stocking tops..
I felt a body press in behind me.. And Steves voice was in my ear… You better be careful I can see everything.. My ass was against his waist as I was stood on the bar rail.. I could feel his hardness against me.. Yes sir I’m sorry ill be more careful.. He reached over pressing harder against me and immediately the bar man came towards him.. What would you like Sarah to drink that is… My body was very unsure of the feelings his closeness was creating in me… Can I have two fruit ciders please Sir.. He ordered for me then said to the barman make sure you keep this young lady topped up she’s a special guest of ours tonight.. Yes sir I’ll be sure of it..
With that Steve placed a hand on my waist and whispered he will look after you.. I’m going to mingle for awhile save me a dance later please…
I automatically said yes sir… And his long body left mine and he disappeared into the crowd… Moving back with the drinks I felt my arse and legs fondled a few times.. Even a few stray hands had pinched my bum.. I got back to Carl and passed him his bottle.. So cool.. We stood drinking, chatting and watching dancing, my ass and legs where felt up in the crowd so many times I just laughed it off and played the naughty schoolgirl to a tee, I was on my third bottle when Steve appeared and I was feeling quite light headed.. Could you help me sell some raffle tickets he asked.. All the proceeds go to your charity in sure we will do well..
Of course sir.. Anything for you.. I smiled at him.. We passed through the crowd together and started to sell the tickets.. I had no where though to put the money… Luckily it was a rich crowd and it was all notes.. The first person lifted my short skirt and slid it into my stocking top… Do I get a kiss for donating so much he asked.. Of course I puckered up and bent over to kiss him on the cheek.. As I did so I felt a sharp sting on my bum as Steve put the cane across my bum.. It didn’t really hurt but it made me jump.. I shot up holding my ass cheeks..
Sir am I being bad.. Yes Sarah.. Ill have to keep an eye on you.. This caused great laughter at the table.. And every table soon got the idea of where to put the money.. If they wanted to see me spanked.. As we weaved out way through my legs and bum recieved so much attention.. Often I was given a drink and I was getting very tipsy on my legs
A lady called us over to donate… I believe I recieve a kiss for this.. I bent over once more, her hand disappeared under my skirt and fondled between my legs she turned her head as I went to kiss her cheek and she kissed me full on the mouth holding me behind my head as her tongue split my lips… Steve was behind me wedged against me his hand was stroking my ass and naked thighs..
Then I felt my shirt lifted out of the way and the cane was brought down harder.. The kiss carried on and my cock got hard in the ladies hand..
Finally she let me go and I was breathless.. This beautiful older lady was grinning at me and licking her lips.. Very lovely Steve.. I think we should try the other room see if its busy..
I think we could get more donations…
She stood and led us towards the wall she clicked a button and a hidden door swung open… As we entered.. It was empty just a few chairs and tables.. My head was spinning as she turned towards me.. She was very beautiful.. Her lips where an inch from mine then she kissed me.. I felt our lip stick sliding together.. And her hand was under my skirt on my cock.. I felt steve hands rubbing my silky ass cheeks.. He pulled my skirt up and peeled my tight pants down my hard cock was in the ladies hand…. And she was wanking me slowly.. Quickly she dropped to her knees and took my whole cock in her mouth.. Steve held me up pulling my head around he started to kiss me his tongue rougher and going deeper than the ladys…
I didn’t resist at all.. I felt my pants pulled down further.. And my naked ass cheeks being stroked and played with the lines of the cane feeling hot as fingers danced across them… I was lifted bodily and placed with my back on the table my legs hanging over.. My cock was consumed again by the ladies hot mouth..
Steve moved to my ass I felt a hard hot thing between my cheeks.. Rubbing against me.. The lady started to kiss me deeply while wanking my cock.. Her mouth covered mine.. The hard thing between my legs pushed further finding my tight hole.. My legs where up in the air either side of Steve’s head he pushed his rock hard cock into me.. My ass tried to fight him off.. But he was strong and had unbeknown to me lubed his cock ready.. I screamed into the ladies mouth as my ring was split.. The head popped in and he rested before taking my waist in is hands and forced his was in my ass.. I was trying to fight them off but they held tight.. My drunkenness helping them.. He carried on pushing it felt like some one was pushing a bat up my arse… Then I felt him all the way inside me his balls and hair against me.. As he held me tight.. He slowly started to fuck me the pain was horrendous by he didn’t stop I was begging now.. But my cock was still hard as the lady took it back into her mouth.. Suddenly his cock started to stroke something inside me the pain didn’t subside as he fucked me.. But I could feel my cock ready to spurt.. Steve fucked me hard and fast my cock was bucking in the ladies mouth… I came down her throat.. As Steve pushed harder impossibly I felt his cock get harder and my arse was filled with hot liquid…. As he slipped out of me my arse felt empty, I was still on my back my legs spread as I felt fingers pull my arse cheeks apart and a tongue enter my stining hole eating the cum from inside me.. As it dribbled out..
Steve appeared at my head I could see his cock was lined with blood and cum hanging softy down.. . He kissed me taking my head and forced his tongue deep in my mouth..
My cock was hard once more.. Time for your first fuck I think Sarah..
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