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A new experience

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By *athy Lovitt OP   TV/TS  over a year ago

Cambridge

I am Cathy, A mature, (old) Transvestite from Cambridge, It started just as any other day, Chores and shopping all done I retired to my room to check on the wonderful gay, bisexual meeting sites, I hadn't had a meeting for three weeks and while gay porn is nice it can never replace the feel and taste of a man, It was while i was flicking between the three sites that i favor that his message came in, " Hello Cathy, I have just moved back to the Cambridge area with my family , I am a dominant man who is looking for a sub sissy, I have read your profile and with a little more training you seem perfect for my needs, While i am strict with my girls There will be presents occasionally, I see from what you state in your profile that you are very sexually motivated, Have no fear, your desires will be fully sated, If you are still interested you will meet me on the disused airfield road at Oakington at half past seven, I shall have a small gift for you and you will address me as "Sir". If i haven't had a reply within the next thirty minutes i shall assume you are not interested and not trouble you Further". Well, i read it again and again, each time getting more excited, Dominant sex and a gift, What was there to consider? I gave it twenty minutes before my shakey fingers typed back my reply, "I will be there ,sir," I arrived at the disused road, there was only one car there, a large family SUV , One look at the driver and i was sure it was him, He beckoned me impatiently towards his passenger seat, "I expect promptness Cathy, I approve of your dress, quite slutty but not over the top, The skirt is a little long, I prefer tan stockings rather than black but it's early days, " He pushed a small bag into my lap, "Your first gift," I have always liked surprise presents and peeped inside, "Take it out Cathy, its your size," I was holding a very pretty pleated mini kilt, but no longer than eight inches. "It's lovely, Thankyou sir, but It is very short, I can't wear that, it will show my stocking tops, "Oh, you will wear it Cathy." I put the kilt back in the bag, We sat chatting a while, and looking down i noticed he had an erection, noticing my glance he said, "Yes Cathy, feel free to stroke it." After giving me the present i felt he wanted to be rewarded and went to unzip him. "No, Cathy, you wasn't told to do that, just stroke me through my trousers," Now that did strike me as strange, but it crossed my mind that he wanted to save it till we got to his place. I was then told to follow his car to the "Fox" pub where we leave my car and continue in his, My spirits soared, As i had stated earlier it had been over three weeks since i had met a man and that was my very limit for going without sex. I went to get out of his car when he reached across and pulled the door shut, "Slip the new skirt on Cathy, thats why i bought it," "What here, It's so short?,", "Just do it and no more arguement." was his short reply, I lifted my bottom and slid off my denim skirt and put the mini kilt on, I must admit it did look nice, even though it showed a narrow length of thigh above my stocking tops but as i thought we were just going to his house it would be ok, We drove to the "Fox" and i parked and slid beside him, As we pulled out of the car park he said, "Now Cathy, be a good girl and do as your told, I know you like recieving presents and after tonight there could be lots more,." Up until this moment i had only seen his erection through his trousers,, i placed my hand on it and felt it stiffen, I smiled to myself, wondering just what position i would be in when it entered me, It was just starting to get dark when he pulled into a large layby on Barton road Cambridge, A layby that i knew well. he drove to the deepest area and parked, Pushing his seat back he smiled at me, "We are here Cathy, Take my penis out and stroke me." My thoughts of being fucked on a nice comfortable bed vanished,, but never mind, i had been fucked in cars before, Itook out his penis and began long slow strokes, I knew this was never enough for men when they are with a girl like me so i lent over to take his rigid tool in my mouth, A hard slap landed on my arm, "No, not for you Cathy," I was shocked, what the hell did this man want, I sat there puzzled, still holding his rigid cock, It wasn't long before i heard a car door open and close further up the gloomy layby, A well dressed elderly gentleman approached his open window, the stranger looked in watching as i slowly wanked Sir's hard cock, "Mmmm the stranger said, she has a nice hand movement,, Sir reaced across and lifted my mini kilt exposing my black panties,, "Yes, she loves it, she is already wet," he looked back at the stranger, "If you come to the passenger side she will suck you off, " The man was already getting his cock out as he walked round the car,, i heard the window go down, I was already turning as he thrust his cock through the window,, It wasn't a very big cock but quite thick, After three weeks with no contact i couldn't wait to take it deep in my throat, The man must have shared my excitement as after five minutes his hands gripped my head, he groaned and the first spurt of spunk hit the back of my throat, it was soon followed by three more, The stranger withdrew and thanked us both, Sir smiled contentedly, "Very good Cathy, You did well, now stroke me some more," i went back to stroking his cock, I am not a novice and it was plain to me now that i was with a watcher, As we chatted i began to sum it up, I was getting what i desired, I didn't have the bother of driving,and there was a promise of further presents, We had been chatting for about a half hour when another car door slammed, This time a much younger man with a shaven head approached his window, This one was more arrogant, looking directly at Sir he said, "Is the slut up for fun,"nodding towards me, "yes, i would think so." sir replied, "The young man wants fun Cathy, Get out of the car and show him your new kilt," i went for the door handle but it was wrenched open before i had chance, He watched me get out of the car, the kilt had ridden up showing my stockings and pantiies, As soon as was out i was pushed against the open door, Glancing in the car i could see Sir really wanking his rigid cock, There was no need to lift this skirt, The young man appeared to untie his jogging bottoms and they fell to the ground, I reached into my bra and took out a condom, As i passed it back the young man spoke to sir, "Does she take it bare",,, "Yes Yes, however you want her." My panties were roughly pulled to one side and i felt the blunt head of a cock pressing against my cunt, Luckily i adopted the habit long ago of always lubing myself before any date, I never got to see the cock that was invading me, It felt thick and twice it rode up my crease before my cunt opened to accept it. As he firmly pushed i felt myself gripping him, "Fuck she's tight," judging by the length of his strokes i would put him at about seven inches,, seven inches of pure delight, gripping my hips he thrust deep ,,"Good girl Cathy, Good girl, take it all," sir encouraged, The car rocked as i pushed back to meet every thrust, After three weeks i knew i wouldn't be able to last long, Just as my orgasm rocked me i felt him grip my shoulders ,pulling me back, spurt after spurt of warm spunk spread inside me, i glanced down to see a dribble of warm cum running down my stockings from my clitty, Sir lay back with a white pool of spunk in the palm of his hand, The young man withdrew his semi rigid cock from me, pulling up his jogging bottoms he muttered ,"Awesome, i will look out for you again Cathy," "Oh she will be here, " added sir, I got back in the car, the warm glow still deep inside me, "You did well Cathy, better than i could have wished, I smiled contentedly as he raised his spunk filled palm up for me , "this could mean another gift Cathy," I held his hand as i licked the spunk, We stayed a little longer but it seemed the action was over for tonight. Once we were back at the "Fox" car park i was given a list of instructions, I was told to take a photograph of myself in the mini kilt i was fucked in and send it to him and to use it as my profile picture, It is the one i am currently using, I have been informed that i am to meet him again on the seventh of June, Alas i am on holiday in Eastbourne on that date, Hugs Cathy x

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By *athy Lovitt OP   TV/TS  over a year ago

Cambridge

still visiting this layby

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By *lderWiserNowMan  over a year ago

Kettrin

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