Before the days of internet chat rooms and social media I was very lonely as a young cross dresser. I can't speak for everyone of course but I would use telephone messaging services to talk to like minded people. I had received my first mobile phone for a recent birthday and I would often call up to chat to people. Sometimes things would turn into phone sex and on the rare occasion I would give out my phone number.

One person whom I deemed worthy enough to have my number was a man called Jack. We would talk regularly as well as texting, despite such things being in their infancy. Over the course of several months I spoke a lot to Jack. He was well spoken, in his early thirties, single, we lived in the same town and he worked in London. I was very nervous talking to someone about my secret but he always made me feel relaxed. Over time our conversations started turning to meeting in person.

Jack never pressured me and always understood my concerns. He always reassured me, telling me there was no pressure. Eventually I grew brave enough to agree to meet but there was a slight problem. Ashamed as I am to admit it now but all of the clothes I wore belonged to other people. My sister, my step mum, and even a couple of my female friends had been victim to my borrowing. Of course this meant I didn't have anything to wear for Jack. He reassured me it wouldn't be a problem and asked me my sizes. I had to guess based upon the things I'd worn before and Jack seemed satisfied as we arranged to meet in a few days time.

When I arrived at Jack's house I was taken aback. He had alluded to the fact he had money but I wasn't expecting this. There sat an impressive BMW in front of a large detached 4 bedroom house. A perfectly kept garden surrounded by high trees and bushes. My heart was beating out of my chest as I reached out for the door bell. Before I could press it the door opened to reveal a handsome, tanned, tall man. Piercing blue eyes, cropped dark hair and a welcoming smile greeted me and led me into the hallway. The room was spacious and immaculately decorated and I couldn't help but feel a little out of place in my scruffy jeans and tshirt.

"I'm Jack." The man introduced himself. "Would you like something to drink?"

"Thank you, just water please." I replied timidly. It felt strange to be talking to him face to face, especially in my own clothes.

Jack showed me into the kitchen and we made small talk as he provided me with a glass of water. We sat talking awkwardly at a large kitchen table before he finally spoke more directly.

"I don't wish to be pushy or presumptive, but I bought you some things. Perhaps you'd like to try something on?"

"I think I would like that." I was incredibly excited. Jack took me upstairs and into one of the bedrooms.

"I had to best guess what you may like from what you've told me. I hope there is something you like. I also bought some things I liked too." He said, pointing to a number of bags on the bed. "There is also some make up on the dresser if you'd like it. Please take your time." I thanked him and he left me, closing the door as he went.

I began to look through the bags and found a couple of dresses and some pieces of underwear as well as a pair of high heels. Amongst everything I found what I thought would be ideal. A virginal white lace bra with a matching white lace thong and a thick waisted white lace waspie suspender belt. I also found a short pleated skirt and a white blouse which I just had to use to create a school girl look which I finished with a pair of black, fence net stockings.

I laid all the items out on the bed and, with a deep breath, I removed my jeans, tshirt, socks, and boxer shorts. I had been removing all my body hair as soon as it started appearing. Being naked in Jack's house felt strangely erotic as I removed the fence net stockings from their packaging and sat on the bed. I always put my stockings on first and as I eased them up over my smooth legs I began to feel an excitement I'd never felt before. I wrapped the waspie around my waist and attached the clasps to the stockings. I eased the soft lace panties up over my stockinged legs and felt a little shock of pleasure as I tucked my cock away. I attached the bra behind my back and adjusted the straps so the soft cups held my shapeless chest. I Felt amazing as I stepped into the short skirt which barely covered the stocking tops. As I pulled the blouse on to my slender shoulders I went to the dresser and sat in front of it.

I'd only lightly dabbled with make up and rather inexpertly applied far too much eye liner and lipstick. Luckily for me the 'over the top' make up look suited me and my school girl outfit. I slipped on the black high heels and looked into the mirror. I felt my nerves surge as I thought about the fact I was about to be seen dressed up for the first time. My long hair had been tied back but I pulled it free to let my dark straight locks cascade over my shoulders. I admired myself briefly in a full length mirror and a tinge of excitement surged through me.
I timidly walked to the door and down the stairs, teetering on the high heels as I tried to walk. I found Jack reclining on a vast leather sofa in his lounge. As I walked in he jumped to his feet.

"Wow!" He walked to me arms outstretched and embraced me firmly. "You look incredible!" I could feel myself blush as his eyes looked me up and down. "Give me a spin!"

Struggling to balance on the high heels I slowly turned around. I felt his hand run gently down my back and onto my arse before returning to his side. I felt sexy and nervous, naughty and shy all at the same time. He motioned for me to sit down.

I smoothed the skirt behind me and gently perched on the edge of the sofa. Jack sat next to me. We chatted for a little while with Jack complimenting me heavily.

"Do you like the clothes? Do they fit?" Jack asked, still looking me up and down.

"Oh yes I love them! Thank you so much! I could never afford to buy anything. If you want some money..." I began before Jack waved me quiet.

"I get to see you dressed up!" He smiled broadly at me. "Let me see you again." He gestured to the open floor in front of him. I stood carefully and did a careful little spin in front of him. I was attempting to be as feminine and delicate as possible while Jack reclined on the sofa. "How does it feel?"

"Really good. I feel sexy and girlie. These shoes are a little tricky though." Looking down at them I attempted a few steps back and forth. I loved the way the skirt bounced against my bare buttocks as I wiggled my hips, attempting to emulate a female walk. After several passes I felt I was getting the hang of it. I spun excitedly to Jack for some kind of praise. He was was leaning back on the sofa, his eyes fixed upon my body as he massaged a steadily growing bulge in his trousers. I was more than a little shocked and I think it must have showed.

"Did you think all of this would come without a catch? You can come here all you like. I will buy things for you, but you will have to earn it." I was mesmerised as Jack unbuckled his trousers and pulled his cock free. He began to tease himself between his fingers as his cock hardened to a thick 8 inches. "Turn around", he ordered.

I nervously turned on the spot. I didn't know what to expect. I felt utterly helpless there, teetering in high heels, dressed that way. In my mind, behind the fear I felt good though. No one had seen this side of me. No one had seen me dressed this way and I had turned him on. I made his cock hard and he wanted me. "Lift your skirt." Came the calm but firm order from behind me. I looked back over my shoulder and saw Jack had removed his trousers and was watching me from the sofa, hard cock in hand. As I reached back to lift my skirt I saw my reflection in the mirror. Suddenly everything changed.

Looking back at me I saw a true reflection of my sexuality. I saw Jessica. I lifted my skirt and revealed my smooth butt, perfectly framed by white suspender straps. I bent over a little to feel them pull against me. I allowed the skirt to fall back into place as I spread my legs a little and bent fully at the waist, knowing my actions would cause the short skirt it to ride up again.

"Good girl!" Came Jack's approval from behind me. I fell to my knees in front of him. On all fours with my tight arse barely visible under my skirt. "Stay just like that." Jack called. "Do not move."

I froze as I heard him stand from the sofa. I felt his hands run up my thigh and disappear up my skirt. He caressed my bare arse before his fingers traced the line of my thong as it disappeared between my firm arse cheeks. I closed my eyes as I felt his strong fingers seek out my cock, tucked away in its lace prison. I began to gently grind against his hand as I enjoyed the feeling of him against me when, with his other hand he lifted my skirt and slapped my arse.

"Don't move." He said firmly. A little shocked I froze. His hand continued to grope me as my cock hardened in my panties. I was motionless as he tugged at my waist band and pulled my panties to my knees. I was nervous as I felt those strong hands spreading my cheeks wide. I let out a moan as I felt his tongue flicking over my tight hole. He danced hot, wet circles with the tip of his tongue as I moaned loudly. He spat loudly and smeared it over my arse as he knelt behind. I felt the tip of his cock as it pressed against my little hole.

"No, please! I've never done that before!" I cried out.

"Then you need to learn." He replied as I felt him push into me. White hot searing pain shot through me as I felt like he was tearing me apart. His hands gripped my hips as I helplessly steadied myself, tears of pain running down my face as he plunged his hard cock in and out of me. Utterly helpless on my knees, dressed like a whore and being fucked like one, I felt something new.

My cries of pain became moans of pleasure as I felt my cock grow harder than ever. As the pain subsided my pleasure grew. I began moaning louder when I felt Jack's hand clamp over my mouth. He fucked me harder, his tight balls slapping against me. Suddenly he pulled himself from me and dragged me to the sofa.

"On your back." He pointed to the sofa. I rapidly complied. He pulled my panties off fully and tossed them away before lifting my skirt fully around my waist.

"You're going to jerk that girlie little cock for me while I fuck your mouth." He had barely finished the sentence when I grabbed my cock and opened my mouth wide. He felt huge and hard in my mouth as he fucked it. Standing over me I choked and gagged but that seemed to spur him on and make him fuck harder. He began to moan and I couldn't hold back. Being used that way, making Jack's cock so hard, being a whore to him. My cock erupted as I jerked it. Even through my blouse I could feel hot splashes of cum landing all over me. Almost at the same time Jack cried out and with one squirt after another he filled my mouth. I swallowed as much as I could but some spilled out over my face. He pulled himself free from my lips and I saw my lipstick smeared over him. He looked down at me as I lay there, my fucked arse hole twitching, covered in my own cum, his spilling from my mouth.

"Thank you, sir." I breathlessly whispered.