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\u2019t 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. <\/p>\n
He texted me "Can I ask you a bit of a kinky favour?\u201d <\/p>\n
\u201cSure I said.\u201d <\/p>\n
\u201cI want you to dress up as a schoolgirl for me,\u201d I thought about it for a few seconds then smiled to myself.<\/p>\n
\u201cYes I said :).: <\/p>\n
\u201cIts just a fantasy I want to try out."<\/p>\n
Mmm I thought, where would I find these types of clothes to wear.<\/p>\n
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.<\/p>\n
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. <\/p>\n
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 \u2013 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. <\/p>\n
The drive to the hotel was scary \u2013 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\u2026 I\u2019d been waiting all my adult life for this. I was yearning to meet D. <\/p>\n
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.<\/p>\n
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 \u2013 like a little girl on Christmas Eve. I couldn\u2019t help smiling to myself.<\/p>\n
I texted D my room number and asked when he would be arriving, a few minutes later I got his reply \u2013 he\u2019d be here in an hour! Butterflies flew around in my stomach. It wasn\u2019t much time for a girl to get herself ready for her lover \u2013 but I would have to look my ravishing best for him.<\/p>\n
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\u2019d bought to make myself smell lovely for D.<\/p>\n
I adore having smooth legs, it makes me feel so very girly.<\/p>\n
Then I put my bra on and padded it out with the inserts I\u2019d recently bought online to make myself a convincing 36-C. <\/p>\n
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.<\/p>\n
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 \u2013 making a tent in the front of my skirt. She always started to stir when I played dress up.<\/p>\n
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!<\/p>\n
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. <\/p>\n
\u201cWow Ashley!\u201d He exclaimed as he saw me in my glory. \u201cYou look fantastic!\u201d <\/p>\n
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. <\/p>\n
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.<\/p>\n
\u201cOh D,\u201d \u201cI\u2019ve been waiting for this moment for so long now.\u201d<\/p>\n
\u201cMe too,\u201d he said, looking into my eyes. I could\u2019ve 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\u2019d just do it.<\/p>\n
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.<\/p>\n
His lips met mine and we kissed, then his tongue danced with mine as he held me even tighter. <\/p>\n
\u201cGod you turn me on Ashley,\u201d he exclaimed, breathlessly as he drew apart. \u201cYou\u2019re fucking gorgeous.\u201d<\/p>\n
\u201cYou\u2019re amazing too,\u201d I whispered, dazzled by this beautiful man and his compliments.<\/p>\n
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. <\/p>\n
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.<\/p>\n
\u201cOh God,\u201d 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 \u2013 making me groan with desire. <\/p>\n
I felt his own desire growing under his trousers. He felt big and I wanted to see more. <\/p>\n
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\u2019d cream my panties, but then he seemed to halt and he looked deep into me eyes. <\/p>\n
\u201cWould you like to show me what a dirty little slut you can be\u201d he said with a grin\u2026 Oh God! I didn\u2019t need asking twice!<\/p>\n
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.<\/p>\n
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. <\/p>\n
I pulled back his foreskin to reveal the purple head, glistening with precum. D looked at me with pleading eyes, but he didn\u2019t need to beg. My hunger was enough. <\/p>\n
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\u2019s cock. And I loved it! <\/p>\n
I tasted D\u2019s precum \u2013 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.<\/p>\n
Why had I waited so long to do this? This was amazing! The taste, the smell. It was all fantastic. <\/p>\n
By now he\u2019d 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. <\/p>\n
\u201cOh you little slut,\u201d he grunted as waves of pleasure washed over him.<\/p>\n
Then I felt him starting to tense. <\/p>\n
\u201cOh baby,\u201d 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.<\/p>\n
D was in bliss. He smiled at me lovingly.<\/p>\n
\u201cThat was fucking amazing,\u201d he said, getting his breath back. <\/p>\n
\u201cThanks,\u201d I said, blushing again as I licked my lips and carefully tucked his penis back into his pants. <\/p>\n
I got back to my feet as D zipped himself up. My own little cockette was straining at my panties \u2013 but I was too ladylike to do anything about it. <\/p>\n
Dan took hold of me and pulled me down onto him for a kiss.<\/p>\n
\u201cYou are a real sexy girl,\u201d he said, holding my waist and kissing me despite my cummy-breath. Then he playfully slapped my bottom through my skirt. \u201cYou naughty girl,\u201d he said.<\/p>\n
\u201cI am a very naughty girl,\u201d I admitted. \u201cBut you tasted delicious and I couldn\u2019t stop myself,\u201d I told him with a smile, running my hand over his chest and admiring his lovely eyes again.<\/p>\n
\u201cI think you deserve a treat for that,\u201d he said, kissing my cheek.<\/p>\n
\u201cWhat kind of treat,\u201d I asked, hardly daring to anticipate.<\/p>\n
\u201cThe very best kind I can give,\u201d he said, taking my hand and standing up. <\/p>\n
He was leading me to the bed. My heart began to gallop. Could this be it, the thing I\u2019d most wanted? But now it was approaching I wasn\u2019t sure I wanted it anymore. I felt so scared suddenly. But D must\u2019ve noticed and he calmed me down.<\/p>\n
\u201cRelax honey,\u201d he reassured. \u201cThis is what you want isn\u2019t it?\u201d <\/p>\n
I thought again of D\u2019s hot sturdy cock filling up my boy pussy and knew it was definitely what I wanted. And I wanted it bad. <\/p>\n
\u201cYou won\u2019t hurt me will you D?\u201d I pleaded with scared little girl eyes. <\/p>\n
\u201cRelax babe, I\u2019ll take it real slow,\u201d he reassured.<\/p>\n
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. <\/p>\n
\u201cOh D.\u201d 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 \u2013for enjoying the fact he was preparing me to be fucked.<\/p>\n
D temporarily stopped his caresses and began to strip off so I started too, but I\u2019d 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. <\/p>\n
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\u2019t 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.<\/p>\n
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. <\/p>\n
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\u2019t hurt me.<\/p>\n
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 \u2013 as if toying with me, and I knew then that I needed his cock inside me more than anything. <\/p>\n
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.<\/p>\n
And then he pushed more and I felt so much pain. This was far worse than the dildos I\u2019d 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.<\/p>\n
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.<\/p>\n
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.<\/p>\n
I looked up to see my panties still clinging to one of my Mary Jane sandals as I gripped him with my thighs.<\/p>\n
\u201cThere\u2019s a good girl,\u201d he groaned as he rode me. \u201cYou sexy little slut.\u201d<\/p>\n
\u201cOh God this is amazing,\u201d I managed to utter as his huge cock drove in to me again.<\/p>\n
\u201cYou slutty little vixen,\u201d he said, delighting me with his very true descriptions of me.<\/p>\n
The pain was gone now, totally replaced by pleasure. I was trying to pull him deeper and deeper inside of me with each thrust.<\/p>\n
\u201cOh God D, you\u2019re so big,\u201d I whispered. \u201cI want your cum deep inside me!\u201d I encouraged, milking his cock with my muscles and squeezing his sides with my thighs as he pounded me harder and harder.<\/p>\n
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\u2019s stomach everytime he drove forwards, and even as D started to near his climax, I felt my own approaching.<\/p>\n
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\u2019s own and sprayed a few drops of girl juice into the folds of my skirt.<\/p>\n
It was the most magical feeling I have ever felt \u2013 knowing that D\u2019s baby making seed was deep inside me \u2013 knowing that he could have impregnated me. Suddenly I really wanted his baby how I wish I was a real girl at this moment…<\/p>\n
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. <\/p>\n
I could feel his cum oozing out of my sore ass and it made me feel so feminine.<\/p>\n
\u201cThat was sooo good,\u201d he murmured, catching his breath. \u201cYou are one hot little slut.\u201d<\/p>\n
I felt so good hearing him say that. I had earned my status. I really was a woman now.<\/p>\n
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.<\/p>\n
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. <\/p>\n
I sat up too and watched his gorgeous buns as he walked into the bathroom. What a dream. <\/p>\n
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 \u2013 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. <\/p>\n
To be continued…<\/p>\n