A Schoolgirl's First Time
Keywords: First, Schoolgirl's, Time, A,
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I"d been emailing and phoning Dan for several weeks when he first suggested that we meet up. It was very exciting and I couldn"t wait. My every waking hour was spent thinking about it. The only odd thing was the request he"d made.
"Can I ask you a bit of a kinky favour?" He"d said as we arranged the meeting.
"Err ok." I"d replied.
"I wondered if you"d dress up as a schoolgirl for me," he stated hesitantly. Not sure whether I"d go for it or not. I thought about it for a few seconds then smiled to myself.
"Of course I will honey." I told him.
"It"s just a little peculiar fetish I have." He explained.
Mmm I thought, and we all have those.
So with that I had to get preparing. I had most things I needed for the outfit, a plain white blouse, a cardigan, white cotton panties, a simple bra and some frilly white ankle socks. All I really needed to complete the look was a short pleated skirt and a pair of black flat heeled girl"s shoes. I was a bit of a heel girl myself so I hadn"t actually got any flat shoes in my collection.
I went out that very afternoon and bought the shoes and the skirt from my favourite shops in town. I do so love shopping for girls" clothes. Most of the time you can see that the assistants don"t really care who"s buying what and most times they just think you"re buying clothes for your girlfriend. But very occasionally they give you a look along the lines of "I know what you"re up to." They"re the ones I really like. Sometimes I"ll even flirt with them and ask them daring questions like "Do you think this skirt will go well with ankle boots?" or "Do you have these panties in another colour?" It"s a real turn on to talk to fellow girls about such things.
On the morning of the big day I woke with girlish glee and started to get ready. I stripped out of my shorty nightie and went to the bathroom to give myself an enema and make sure my boy-pussy was extra clean for Dan. Then I put a lubricated tampon in my pussy to keep it nice and moist. Mind you, the thought of what Dan might do to me was enough to make my panties wet through.
My holdall contained all of my clothes and my wig and my handbag too. I made one last check of it before I put it in the bag KY jelly, tampons, femm wipes, lip-gloss, mascara, blusher compact. I seemed to be all set. With trepidation I left the house and walked out to the car.
The drive to the hotel was scary I kept wondering if I was doing the right thing. Perhaps it was too soon for all this? Then I realised I was kidding myself
I"d been waiting all my adult life for this. I was yearning to meet Dan.
When I got to the Travel-lodge I checked in and collected the key from the unknowing receptionist. I was scared they would know what I was up to. But how could they? I was just a guy in a suit called Steve Woods to her, but soon I would be a sassy schoolgirl called Phillipa and hopefully the stuff of Dan"s dreams.
When I reached the room and took my bag inside, I locked the door behind me, knowing that I would be a whole different person when I left again. I was so excited like a little girl on Christmas Eve. I couldn"t help smiling to myself.
I texted Dan my room number and asked when he would be arriving, a few minutes later I got his reply he"d be here in an hour! Butterflies flew around in my stomach. It wasn"t much time for a girl to get herself ready for her lover but I would have to look my ravishing best for him.
First I took off all my dull man clothes and hid them away in the wardrobe. I wouldn"t need them for a while. Then I showered and reshaved my legs and arms and face and got rid of all that unsightly hair that us girls so despise. I dried off and used some of the lovely girly fragrances I"d bought to make myself smell lovely for Dan.
I adore having smooth legs, it makes me feel so very girly.
Then I put my bra on and padded it out with the inserts I"d recently bought online to make myself a convincing 34-C. Nothing too daunting for the man!
I admired my boobs in the mirror I was already looking hot to trot.
Next step was my wig. It was a shoulder length blonde wig that was my particular favourite of the three or four I owned. I think it makes me look rather young and I knew Dan would like it.
I secured it firmly in place with a couple of pins and made sure it all combed out properly. Perfect, I thought, giving my head a spin and watching it fan out.
After pulling on my skirt and my ankle socks I buttoned up my blouse and put on my cardigan. I put on my extra length lashes and a bit of blusher then I put on my frosted pink lip-gloss and blew a kiss at the mirror. I was turning myself on I looked so sexy. My little cockette was starting to get very excited making a tent in the front of my skirt. She always started to stir when I played dress up.
I took out my tampon and put a long squirt of KY deep up my pussy then pulled on my schoolgirl panties, hiding my girlish cockette away out of sight so that Dan wouldn"t see the signs of it, even if he did know all about it.
As I painted my nails I looked anxiously at the clock. It was nearly time for his arrival! With my nails still drying, I put my clip-on earrings in place and secured my necklace, before carefully buckling on my shiny Mary Jane shoes and spraying a few squirts of perfume in the places us girls like to smell particularly fresh. I was ready for him!
Funnily enough, within moments I heard a knock at the door and my heart leapt! I felt just like the giggling schoolgirl I was dressed as, as I ran to the door to let Dan in.
"Wow Phillipa!" He exclaimed as he saw me in my glory. "You look fantastic!"
I blushed at his compliment and told him how hunky he looked. He did too. Six foot tall and well toned, short brown hair and gorgeous eyes. I was creaming myself just looking at him.
"Come in," I said, taking his coat and hanging it up. "Are you ok?"
"I am now I"m with you," he said with a smile, taking hold of my arms and gently kissing my cheek. I felt so girly and feminine in his arms. So small and gentle and petite against his big muscly form. I just wanted to melt into his arms and be whisked away.
"Oh Dan," I sighed, romantic thoughts whizzing around my head. "I"ve been waiting for this moment for so long now."
"Me too," he said, looking into my eyes. I could"ve dived right into those deep brown pools. His voice was gorgeous too; so deep and masculine. He could ask me to do anything and I know I"d just do it.
He leaned in then to kiss me and the smell of his aftershave and the feel of his stubble on my dainty cheek made me weak at the knees. He was so manly and he made me feel so special.
His lips met mine and we kissed, then his tongue danced with mine as he held me even tighter.
"God you turn me on Phillipa," he exclaimed, breathlessly as he drew apart. "You"re fucking gorgeous."
"You"re amazing too," I whispered, dazzled by this beautiful man and his compliments.
He took my hand and led me to the sofa and I sat down. I made sure I sat as ladylike as I could, smoothing my skirt out behind me before I sat down, and keeping my thighs close together. There would be time to reveal the prize to him later.
Dan sat next to me and began to run his fingers through my hair, smoothing it behind my ear then moving in close to kiss my neck. I could feel the emotions sloshing about inside of me as his lips made contact with my skin. I wanted this man so badly. I wanted to be his girl. No, I wanted to be his woman.
"Oh God," I breathed as he placed a hand on my knee and gently ran it under my skirt. I started to feel his leg with my hand. I felt the muscles of his thigh and I moved higher as his own hand quested higher up my thigh too. He came to my panties and paused. Then he started to rub my little cockette making me groan with desire.
I felt his own desire growing under his trousers. He felt big and I wanted to see more.
I gave his cock a little squeeze and he murmured his enjoyment. He kept rubbing my cockette and I thought that if he carried on much longer I"d cream my panties, but then he seemed to halt and he looked deep into me eyes.
"Would you like to show me what a dirty little slut you can be" he said with a grin
Oh God! I didn"t need asking twice!
Excitedly, I got down on my knees between his legs and with my delicate fingers I unzipped his fly. I reached inside and unbuttoned his boxer shorts for the prize beneath. And there it was. I pulled it free and it stood proudly to attention.
His penis was magnificent, at least 8 inches in length and much more of a specimen than my girly cockette, hidden beneath my flowery cotton panties.
I pulled back his foreskin to reveal the purple head, glistening with precum. Dan looked at me with pleading eyes, but he didn"t need to beg. My hunger was enough.
Opening my pink frosted lips, I began to gently lap at the head of his penis, the musky smell filling my nostrils and making me moan. Finally I was living out my dreams. Now I truly was a cocksucker. A panty clad tranny, sucking my lover"s cock. And I loved it!
I tasted Dan"s precum it was like nectar and I wanted more. I began to swallow more of his cock in my mouth, sucking on his rigid pole, working it with my hand and tongue in harmony. All the time Dan kept saying how good it felt.
Why had I waited so long to do this? This was amazing! The taste, the smell. It was all fantastic.
By now he"d shrugged his trousers down a little, and with my other hand I started to massage his balls as I kept on sucking, taking more and more of him into my throat.
"Oh you little slut," he grunted as waves of pleasure washed over him.
Then I felt him starting to tense.
"Oh baby," he grunted, his legs tensing up. I knew he was about to come. I kept on sucking at the same pace until suddenly he juddered and my little girly mouth was full of his delicious cum. He spurted several times, splashing my tonsils and filling my mouth so that it dribbled out of the corners.
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Keywords: First, Schoolgirl's, Time, A,