I have been texting and emailing D for several weeks when he first suggested that we meet up after I showed him some photos on Craig’s List. I was very excited and I couldn’t wait till we met but it would be my first time out in public. I thought about it all the time and at first the only odd part was what he wanted me to wear.
He texted me “Can I ask you a bit of a kinky favour?”
“Sure I said.”
“I want you to dress up as a schoolgirl for me,” I thought about it for a few seconds then smiled to myself.
“Yes I said :).:
“Its just a fantasy I want to try out.”
Mmm I thought, where would I find these types of clothes to wear.
I went online and bought a plain white blouse, a cardigan, white satin panties, lace bra and black ff seamed stockings with a black garterbelt. I found the uniform skirt online at amazon with a fair of black flat mary janes.
On the morning of the big day I woke with girlish glee and started to get ready. I stripped out of my teddy and went to the bathroom to give myself an enema and make sure my boy-pussy was extra clean for D.
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 k**ding myself… I’d been waiting all my adult life for this. I was yearning to meet D.
When I got to the hotel and I checked in and collected the key from the unknowing receptionist. I was scared they would know what I was up to. Soon I would be a naughty schoolgirl for D and feel him inside me.
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 D 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.
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 D.
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 36-C.
Next step was my wig. It was a shoulder length brunette wig that was my particular favourite of the three or four I owned. I think it makes me look rather young and I knew D would like it with the pig tails and cute glasses I would wear.
After pulling on my skirt and my stockings on I buttoned up my blouse and put on my blazer. 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.
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 D in.
“Wow Ashley!” 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.
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 D,” “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 Ashley,” 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.
D 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. D 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 D’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 D 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. I used my tongue to lick it all up and gather the strands that ran from my mouth to the head of his cock. It tasted salty and almondy but I lapped it all up greedily as if it were cream. I smiled, feeling so proud of myself for giving such a good blowjob.
D was in bliss. He smiled at me lovingly.
“That was fucking amazing,” he said, getting his breath back.
“Thanks,” I said, blushing again as I licked my lips and carefully tucked his penis back into his pants.
I got back to my feet as D zipped himself up. My own little cockette was straining at my panties – but I was too ladylike to do anything about it.
Dan took hold of me and pulled me down onto him for a kiss.
“You are a real sexy girl,” he said, holding my waist and kissing me despite my cummy-breath. Then he playfully slapped my bottom through my skirt. “You naughty girl,” he said.
“I am a very naughty girl,” I admitted. “But you tasted delicious and I couldn’t stop myself,” I told him with a smile, running my hand over his chest and admiring his lovely eyes again.
“I think you deserve a treat for that,” he said, kissing my cheek.
“What kind of treat,” I asked, hardly daring to anticipate.
“The very best kind I can give,” he said, taking my hand and standing up.
He was leading me to the bed. My heart began to gallop. Could this be it, the thing I’d most wanted? But now it was approaching I wasn’t sure I wanted it anymore. I felt so scared suddenly. But D must’ve noticed and he calmed me down.
“Relax honey,” he reassured. “This is what you want isn’t it?”
I thought again of D’s hot sturdy cock filling up my boy pussy and knew it was definitely what I wanted. And I wanted it bad.
“You won’t hurt me will you D?” I pleaded with scared little girl eyes.
“Relax babe, I’ll take it real slow,” he reassured.
We lay on the bed and started to kiss and caress each other. My heart was beating so fast I thought I might faint. His hands ran under my plaid skirt and parted my thighs, creeping up my legs to brush over my panties. His kisses got more and more passionate and I felt in heaven. He caressed my tits and my thighs, and made me feel so femmy. Then he slipped his hand down the back of my panties and to my delight he gently probed my ass.
“Oh D.” I murmured as his finger entered me and moved inside me. I clenched at his finger as I felt it explore my warm secret place. Then I felt a second finger joining it, sliding into the moistness. I rose to meet the questing fingers, feeling like a brazen hussy for wanting him inside me so much –for enjoying the fact he was preparing me to be fucked.
D temporarily stopped his caresses and began to strip off so I started too, but I’d only taken my little black cardy off when he told me to stop. I understood, and helped him undress instead. Revealing his rippling muscles as I took off his shirt I felt so proud to be losing my cherry to such a stud. All the other girls would be so jealous of me.
Then, I pulled down his boxer shorts to be reunited with his fabulous cock. It was reinvigorated and ready for me. But was I ready for it? He gently pushed me back to the bed and my hair fell like a halo behind my head. Then he carefully pulled down my panties and tried to untangle them from my feet, but they caught in the buckle of one of my shoes and remained wrapped around it. He didn’t care and nor did I. By now I only cared about one thing. I wanted D inside of me. Filling me up with his huge cock.
He lay between my legs and coaxed me to raise my knees. I did so nervously, already feeling like I was past the point of no return.
My skirt fell around my waist as his gorgeous naked body lay between my thighs. I could feel his body moving between my legs and I felt so nervous suddenly. I hoped he was true to his word and didn’t hurt me.
Then I felt his penis probing at the entrance of my boy pussy for the first time and I gasped a little as he pushed so that it was barely in an inch or so. He waited – as if toying with me, and I knew then that I needed his cock inside me more than anything.
I grabbed his buttocks, pressing into them with my painted fingernails and urged him to take me. Trying to relax my ass muscles to accommodate him.
And then he pushed more and I felt so much pain. This was far worse than the dildos I’d experimented with. I nearly screamed with the pain, but I tried to be brave. Then I realised he was fully inside me and I felt a surge of elation. I gripped his shoulders with my fingernails and dug in. I had taken a man inside of me.
But God he was so big. I felt like my ass would tear apart. But as the pain died away, it felt like the best feeling in the world. My boy pussy was finally full of his cock and I loved it.
He began to gently ease in and out of me, kissing me as he did so, thrusting with his tongue as he thrusted with his cock.
I looked up to see my panties still clinging to one of my Mary Jane sandals as I gripped him with my thighs.
“There’s a good girl,” he groaned as he rode me. “You sexy little slut.”
“Oh God this is amazing,” I managed to utter as his huge cock drove in to me again.
“You slutty little vixen,” he said, delighting me with his very true descriptions of me.
The pain was gone now, totally replaced by pleasure. I was trying to pull him deeper and deeper inside of me with each thrust.
“Oh God D, you’re so big,” I whispered. “I want your cum deep inside me!” I encouraged, milking his cock with my muscles and squeezing his sides with my thighs as he pounded me harder and harder.
I could tell he was coming, but more importantly so was I! My little cockette, buried beneath the pleats of my skirt was being massaged by D’s stomach everytime he drove forwards, and even as D started to near his climax, I felt my own approaching.
Then with a cry of triumph he came violently and I felt his hot sperm gushing into me as my own little cockette made a little leap of it’s own and sprayed a few drops of girl juice into the folds of my skirt.
It was the most magical feeling I have ever felt – knowing that D’s baby making seed was deep inside me – knowing that he could have impregnated me. Suddenly I really wanted his baby how I wish I was a real girl at this moment…
D stayed inside of me and on top of me as we cuddled and let our hearts slow. I kept squeezing him gently with my boy pussy, but already he was softening and after a few minutes his penis plopped out.
I could feel his cum oozing out of my sore ass and it made me feel so feminine.
“That was sooo good,” he murmured, catching his breath. “You are one hot little slut.”
I felt so good hearing him say that. I had earned my status. I really was a woman now.
We stayed cuddled up for about an hour and I dreamt so many lovely dreams in that time. It was one of the happiest moments of my life.
Then D roused from his sl**p and kissed my forehead and got up and started to gather his clothes before heading to the bathroom.
I sat up too and watched his gorgeous buns as he walked into the bathroom. What a dream.
I pulled my flowery panties up to help keep his cum from running down my thighs, but as I sat up I could feel it pooling in the gusset – all sticky and warm. It would give me a lovely memory of D when he was gone. Though I knew now, that I would be his loyal cock-sucking slut for as long as he wanted me.
To be continued…