I saw the most beautiful woman at the world at my new job. Her name was Michelle and it was love at first sight. I knew immediately that I couldn't let her slip away and one day when we were alone in the break room I made my move. I ran over a few pickup lines in my head but discarded them all as too cheesey to use on her. Instead I simply walked up and introduced myself."Hi my name is Rafe," I said and held out my hand. She gave me a kind of odd smile and didn't take my hand in return."I'm Michelle," she said and leaned forward to give me a full body hug. I was in heaven feeling her breasts pressed against me. I hugged back for what was probably too long and when we parted she smiled at me and my knees began to wobble."Would you like to have dinner with me some time?" I asked my voice cracking like it hadn't in more than ten years.She said we should have dinner at her place, she would make me a delicious home cooked meal. I was excited to get to see her place already and wondered if things might lead to the bedroom. She gave me directions and a light peck on the cheek and walked out of the breakroom with my heart around her neck. The rest of the day went by agonizingly slowly and by the time I got back to my apartment I felt like I was a giddy kid with his first date to the school dance.Finally I was on her front porch. She lived in a mid sized house in the middle of suburbia. I rang the doorbell and she opened it a few minutes later and my jaw hit the floor. She was wearing a white button up shirt with only a few buttons done, a plaid skirt that didnt even come to the top of her white stockings which led down to black patent leather shoes."Come on in Rafe," she said and flashed me that smile again. My cock was instantly rock hard as I followed her into the dining room.I barely remember eating dinner, some kind of chicken I think, and afterwards she cleared the plates and came back in from the kitchen which was behind me. She gently started rubbing my shoulders and kissing my neck softly and I was letting out soft moans showing her how much I loved it. Suddenly she slipped one of those sleeper blindfolds over my eyes. I can get into some kinky stuff so I didn't do anything. Then her lips were on my ear and she whispered."I'm going to leave you a trail to follow. Count to one hundred slowly and come find me." She licked my ear and then she was gone.I begane to count, my dick getting harder with every number, finally years later I reached one hundred and took the blind fold off. I looked around and saw that the kitchen door was closed, but the door to the living room was open. I walked into the living room and saw her shoes placed neatly on the floor. I walked over to them and then saw her stockings laying near the hallway. I made my way over there and her shirt came into view, then finally I found her plaid skirt in front of a door. I slowly pushed it open to find her kneeling at the foot of a bed in a room full of lit candles. She was only wearing her panties and she smiled at me.I walked over to her and she immediately yanked down my pants and briefs and just inhaled my cock. I moaned loudly as she sucked me and bobbed her head up and down. She kept doing this move with her tongue around the tip of my cock and I knew if she kept that up I would cum in no time. I wrapped my hands in her long hair as she moved faster and suddenly I was moaning that I was cumming. I expected her to pull off but she just sucked harder and soon I was flooding her mouth with my cum. She gobbled it all up then stood up and kissed me and to my shock she passed a gob of my cum into my mouth and pulled her mouth away. I didn't want to spit it onto her carpet so I just swallowed it."You feel up to returning the favor lover?" she asked seductively and I immediately dropped to my knees eager to get a taste of her pussy.She yanked down her black thong quickly and to my horror the biggest dick I'd ever seen in my life sprang out and smacked me in the chin. It was at least nine inches long and four around. I looked up at her shocked and she simply smiled. She snaked her fingers into my hair and suddenly jerked hard sending a lance of fire across my scalp and causing me to gasp in pain. The slight opening of my lips was enough and she forced her giant cock into my mouth. I was disguted but I never once thought about biting her as she rammed her cock in and out of my mouth. She kept it up for nearly ten minutes before I realized I was beginning to enjoy the feeling of her hot dick moving back and forth in my mouth. I began moving my tongue around trying to copy what she had done to me and after a few minutes I had her moaning. My head was now bobbing up and down on its own and while I hadn't managed to copy exactly what she had done I found something that was making her moan like a ghost with pleasure. I would suck hard on the head while jerking her shaft then bob up and down sucking hard on the rest of her my tongue moving over ever inch of her wonderful, stiff member all the while my other hand squeezed and fondled her hairless balls. She started moaning that she was cumming and I grabbed her ass planning to ram her into my mouth as far as I could get her. She put her hands on the back of my head and we both ended up pushing at the same time causing her dick to pop into my throat. She immediately began firing huge blasts of cum into me coating my throat and filling my stomach up with a creamy dessert I'll never forget.I stood up and kisses her our rock hard cocks slightly bumping heads like two dogs sniffing and getting to know one another. We kissed for a few long minutes with out dicks rubbing and bumping against each other. After a while she broke the kiss and the silence."Bend over the bed for me?" she almost pleaded. I knew what was coming next and was somewhat afraid but I was also very curious.I bent over the foot of her bed and she gently applied some warm lotion to my asshole rubbing it softly and then she popped a finger inside of me. I moaned lightly while she worked me with her finger. She squeezed some more lotion out of the tube and forced a second finger inside of me. There was a sharp spike of pain the quickly faded and I was moaning again while she finger fucked my ass. I looked over my shoulder at her and said in a rather husky voice."I'm ready for your dick."She left out a soft moan and her cock jumped wildly as she began rubbing lotion onto it. She gently poked at my asshole and I let out a soft groan. Suddenly she popped into me and the pain was overwhelming. My face screwed out and I let out a loud cry, she stopped moving and gently rubbed my back. The pain slowly eased and I rocked a little letting her know I was ready for more and she slowly began pressing forward. I let out little gasps and moans wriggling my ass in pleasure as she filled me up, suddenly I felt her stomach pressed against my ass and knew I had all of her in me. I let out a loud moan and leaned forward thrusting my ass up at her.I looked over my shoulder at her and moaned, "fuck me please." I was almost begging and Michelle gave me just what I wanted. She began thrusting in and out of me hard and I moaned and screamed the whole time even begging for more at one point.Hours later we both lay panting ina pool of our cum. She had fucked my tight little ass with her massive dick at leastsix times and it was nearly five am. We both had to be in to work soon and we fell asleep in each others arms.I woke up at 7:30 and she was gone. I got up and used her shower and put the clothes I had on last night back on and drove to work. When I got there it seemed like everyone was giving me sly, knowing looks. It was almost as if I had on one of those big signs that they pay kids to wear outside of department stores, only instead of it saying half off on housewares mine read "I got fucked up my ass by a shemale last night!" As I approached my office I saw I had several messages pinned up on my "While you were out" board. When I got near enough I realized they weren't messages but pictures of me. They were from last night! I immediately began taking them down and looking at them.There was one of my on my knees with a mouth full of dick, one of my face when I turned around and told her I was ready for her dick, and another that I guessed was my face when she first crammed her fat cock into me. There were a bunch more, all still shots of our fucking and as I looked at them I heard something familiar coming from inside my office. The sound of my own voice begging Michelle to fuck my ass harder and people laughing. I barged inside to find several people sitting around a tv set watching me get fucked by Michelle's big cock."Oh GOD fuck my ass harder Michelle I need it!" I was screaming on the tv. I realized her entire room must have been filled with hidden cameras. "fuck MY ASS fuck IT fuck IT AGGGHHHHH!"Suddenly Michelle stood up from one of the chairs with a wicked smile on her face. I hadn't seen her when I came in. She looked at me and lifted up her skirt exposing her giant dick."Aren't you going to come say good morning?"