4 comments/ 34723 views/ 9 favorites Oliver's Story By: theilluminaughty *************Author's Note************ Hey guys. This one tells the story of a man who gets transformed into a woman. Just your average trans story... Sorry about the sudden POV change, I just wanted to pull it in a different direction. *********************************** Beginning: Narrator Oliver got out of his car. He locked the BMW M3 convertible and walked up to the basement level elevator doors of his apartment in London, England. He looked up at the ceiling lights in the small, clean elevator. Make no mistake, Oliver was not a poor man. He was a success story of the New York Lottery, having won an enormous jackpot of $1B last year in 2049. He moved to the UK in April of 2050, last month.. Since then, he hadn't worked and never intended to. He went out and saw friends, shopped, went to museums, all of it. He lived like a senior citizen but was 23. Oliver stepped out of the elevator into the well lit hallway with the velvety red carpet floors. His brown red-accented hair looked almost blonde in the light. His white canvas pants made a soft swishing noise as he walked to his room, a large studio apartment on the 49th floor, only topped by the penthouse above him. He reached out his arm, covered by a denim casual collared shirt, unbuttoned to show a plain black tee, and unlocked his door. He pushed it inwards, walking up to his floor-to-ceiling windows. He put down his bag and stretched out his arms above his head, heightening him 14 inches to 7'6". As he did this, a cylinder of red light appeared around him. Snakelike tentacles grabbed him by his arms and legs and pulled his arms and legs away from his center, pulling his joints. They separated them, the tentacles pulling apart the gucci shoes until he looked like Da Vinci's drawing of the body. Cubes of gel ten feet tall enveloped him on either side, consuming his entire body except for a small breathing hole. His clothes melted away, his wallet thrown out of the cube and his phone wiped as it followed the same path. Oliver freaked out, letting out a scream that was inaudible. Suddenly the tentacles came back, releasing me as I was suspended in the gel. Three tentacles with open suction-like cups grabbed his nipples and his belly button. A fourth, much wider, grabbed his cock. It sucked on the 8 inch meat, causing Oliver to moan. He stopped as thin tentacles approached his face. The pair attacked his nose, latching on to his brain. A much wider tentacle approached him from the rear, playing with Oliver's tight, virgin asshole. He moaned and moaned, weirdly deriving pleasure from this incredibly gay experience. His mind went off his slight homophobia as he braced himself to take the tentacle. It stretched him, causing Oliver to elicit a loud moan. He almost screamed as it pushed its full girth up his asshole. Two tentacles, about as wide as quarters, approached his face as he suddenly felt the tentacles on the front of his body start sucking. He moaned as the tentacle gave him a sensation like he was penetrating and getting blown at the same time. He couldn't help moaning as the tentacles sucked his nipples, and the two tentacles in front of his face attacked, shooting down his throat. He gasped as they started pumping liquid, very quickly. His stomach filled, not able to catch up. The huge tentacle in his asshole started pumping a thick warm liquid, making him incredibly horny. He bucked his hips as he was filled with liquid. His stomach began to stretch, unable to jettison or take in the liquids. In minutes, he was swallowing the substance like a cum slut, not wondering about why the tentacles were doing this. Suddenly a different liquid rushed through the tentacle on his cock, and he felt his cock absorb it through his member. He felt his balls shrink, but didn't notice his cock doing the same thing inside the tentacle. Suddenly his body began to absorb the liquid in the pregnant-like belly curve he had developed. It shrank, back to its normal, muscular size. He felt his body materials being redistributed, developing wider hips and he could barely see his legs get thinner and his abs disappear entirely into a thin, flat stomach over the boobs that were developing. As he felt his biceps shrink into thin arms and his shoulders narrow, he drifted off. Oliver woke up. He sat up, forgetting about how light his core was. He saw his large tits, and the thought suddenly popped into his mind: I'm a girl. He had all of his memories from before, but didn't remember anything about his body. He stood up, noticing his chest-length wavy blonde hair swishing in front of him. He dashed to his room, looking for something to wear. He found a pair of jeans that hung off of him loosely. He found some boxers and a t-shirt that used to be too small for him. He walked into his bathroom, looking at himself in the full-length mirror. He felt aroused, but couldn't figure out how, at his enormous tits, which looked gigantic on a 5'5" frame. He looked down, at his solid, flat stomach. He had curves that seemed better than any girl he had ever seen. He felt more and more aroused as he looked at himself. He looked at his ass in the mirror over his shoulder, and felt like he almost came on sight. It was the roundest, best-looking ass he had ever seen. Oliver put a small hand into his pants and gasped. The unmistakable but unfamiliar feel of a soaking wet pussy met his fingers. He pulled the boxers off, admiring the beauty of the cleanly shaven, smooth pussy. He felt it pulsate as he had what could only be described as a female orgasm. Oliver brought his hands between his legs, sticking an index finger in his cunt. He licked off the juice, massively horny as shown by his perky nipples. Oliver turned, getting into the shower. He filled the bathtub, putting his fingers down there again. He came in minutes, and washed his wavy blonde hair. He dried it, stepping out. He put the shirt and the boxers, which he immediately soaked through. He decided that today he'd need some new clothes. As he put on the pants, he walked up to his shoes. He noticed that he had shrunk noticeably, about a women's 7 compared to his old men's 13. Oliver grabbed his wallet and his phone, which he noticed was clean of everything except for his contacts and his mail. He looked at his phone number, seeing one he didn't recognize. He wiped his confused look off and went outside in the clothes, his boobs bouncing as he stepped. Definitely a lingerie shop necessary today. As it was May, it was around 70 degrees in American numbers in London. Oliver felt a little warm in his jeans as he walked to the elevator. Oliver walked in, facing away from the door as the elevator began to move. The man in the elevator, in a full suit and carrying a briefcase and keys to a Bentley, looked at him. "Who are you?" The man said as we walked out of the elevator in the garage. "I'm Mr. Castle's cousin, sir, I'm on an extended visit here." Oliver said, noticing for some reason a thick Brit accent. His last name was Castle. "Oh, well I hope you have a good time here." He said, staring intently at my cleavage. I turned away, unlocking the BMW. I put the roof down on the M3 and pulled away, on to the busy London streets. Oliver's POV I pulled into the parking lot in front of a mall. I stepped for the first time ever into a women's clothing store, which I knew was very popular with dresses and jeans, as well as shirts. I bought several shirts and pairs of jeans, noticing to my astonishment the small size of the skinny jeans I bought. The shirts were considerably larger, accommodating the new girth of my chest. I bought ten or fifteen dresses, only one of which went below my knees. The rest were incredibly short, I could easily see between my legs when looking at myself in the mirror sitting down. I racked up a crap load before even getting to shoes. Two pairs of 5 inch heels, a set of flats, a pair of sandals, a set of flip flops, the list went on. I bought all of them, indeed a size 7. I bought several sets of yoga pants and leggings before I walked out, having spent at least 2 crap loads. Next was panties and bras. For this, I went to a small store, looking quiet and orderly but it housed one of the biggest sex shops in London. I was greeted by leather, so much leather. I went for a proper leather jacket, which looked incredibly sexy on my tiny frame. I quit distracting myself, moving on to bras. I measured a 36J, positively enormous. The woman who helped me was surprised. She directed me towards several different types. I ended up picking out several shapes, including a few shear ones, a bunch of comfortable ones, and several lace bras. I moved on to panties, getting a couple full panties an several thongs and g-strings. Satisfied, I made my way to the register. I was sidetracked on the way back, staring at some dildos. I was overcome with lust, and I had to purchase a set of beads, 6 of them as big as baseballs, and a 10 inch dildo that looked about 5 inches around. It was huge, and to my delight it vibrated. I walked proud to the register. I had managed to spend more than half what I did at the mall. I drove home, pulling in quickly to the parking spot and walking, arms adorned with shopping bags, to the elevator. I rushed back to my room to change. My pussy was soaking, my boxers already dripping wet. As I closed the door, even, my jeans were coming off. I put the clothes away. I walked around the apartment naked, dripping on to the couch and the floors. I was overcome, deciding I needed to satiate the desire. I pulled the huge connected string of balls and the monster dildo and went to the shower. My incredibly tight asshole awaited me, hidden in between my perfectly formed cheeks. I pushed one end of the beads up to the soft skin, shocked that it took the huge thing. I pulled the first one in, pacing the shower as I dragged it behind me, gripping to dear life by my asshole. I sat at the bottom of the tub, pushing another one in. The sheer size was enough to make me scream with pleasure. The third ball went in, my asshole in slight pain but my whole body in ecstasy. I grabbed the dildo, pushing it up against my incredibly tight pussy. I had slept with girls before, but I had never seen a pussy as tight as mine. The head went in, and I squealed as it started vibrating. I slowly descended the 10 inch dildo, moaning so loudly that my neighbors could hear through the thickly insulated walls. As I pushed the fourth ball in behind me, I felt a sudden pang of pain deep inside my stomach, and gasped at the sharpness of it. My reflexes let go and my pussy tightened suddenly. My cunt swallowed the 10 inch behemoth, closing around it. I moaned, regretting getting one without balls or a stopper or anything. I came suddenly, tightening my love lips further. The sudden drive of adrenalin made me subconsciously push the fifth ball in. My entire weight, seemingly about 120 pounds, relied on my asshole not swallowing the last ball. I stood up, feeling the sharp pang of pain again, but I was in total ecstasy. I shockingly came again as the 10 inch behemoth vibrated inside of me. My asshole let go and tightened again, taking in the last ball. I moaned and screamed as I came again. This was the third time in ten minutes. I got out of the shower, drying myself off. I walked funny, waddling to the bathroom with my legs clenched together. I knelt on the floor and leaned on all fours, attempting to push the beads out. I managed to get them up to my canal, opening my asshole. I could see the black ball in the mirror between my legs. I put a hand over my back and around my butt, and attempted to push my fingers in there like I saw women do in porn. I managed to get my fingers all inside before I came again, pushing the dildo in my cunt even further. I managed to pull the first ball out, followed by the second. The third came out and then I came again. God, I loved being a woman. A fourth, a fifth. I grabbed the last one, yanking it out as I felt the immense pleasure of the vibrator deep inside of me. It stopped vibrating, to my great relief. I tried to push it out with the muscles on my walls, but it wouldn't budge. I decided to leave it, and put on some clothes. Olivia's POV Two hours later, I walked to the elevator of my building. A man walked close beside me, walking out of the room two doors down, closer to the elevator. He introduced himself as Oliver Quentin, Chief of Design at BMW. I told him I knew who he was. Oliver asked me my name. "Um... Olivia. Olivia Castle." I said. "I drive one of your cars." I blurted, motioning to the BMW key with the M3 monogram on it. "Oh, really?" He said, obviously looking at my tits through the red sequin dress, which only went just below my ass. My black bra matched the black lingerie panties I wore over my now soaking wet pussy. The theme went on down to the black 5" heels I was wearing. My feet hurt like hell, but I heard these made your ass look great. We got into the elevator, and I felt the dildo still inside me almost crowning. He faced me, much taller at a 6'3" compared to my 5'10" with the heels on. He stepped closer, inches away. Oliver looked down at me. "I'm sorry, Olivia, you are an incredibly gorgeous woman." He said, caressing my face, hand around my ass as he kissed me passionately. I moaned, feeling the dildo maximum two inches from my pussy lips. I pressed the emergency button, the button I knew full well did not call for help, only stopped the elevator and cancelled the call. I pressed the button for my floor. "No apologies necessary," I said, kissing him back. We made out, going back to my apartment. We barely got through the door before the end of the black dildo pushed out of my cunt. I caught it before it hit the ground, putting it on the table without him noticing. I guided him to the bedroom, still sucking face. He pushed off his jacket onto my bedroom floor. Then his shirt. I pulled off my shoes with him, then off came my dress. I pushed him on to the bed, then straddled his shins, face level with his belt line. I pulled off his pants, revealing a pair of incredibly stretched boxers. I pulled them off, his hard cock slapping me on the cheek. He must have been 11" long, and at least 4" wide. He was enormous. I put my lips on it, kissing his member. I wondered why I had decided to go along with this, but i kept going. I was incredibly horny, putting his cock into my mouth. He expanded again, at least an inch and a half. I sucked on, moving down his enormous length. I got 8 inches in my mouth before I choked. I stopped, licking him up and down his shaft. He moaned, and I kept going. His almost 13 inches was the biggest I had ever seen, granted, i hadn't seen very many. He sat up, taking my head off of his length. He sucked on my enormous tits, removing my bra. Oliver rubbed my thong, easily getting through the fabric. He stroked my pussy lips, sucking my tits. He moved his face down, and I bucked my hips into it. He began sucking on my cunt, licking it over and over. I moaned loudly, in complete ecstasy. He fingered my cunt, sticking one in at a time. He stopped suddenly, kissing me again. He teased my pussy lips, and I felt his member push inside me. I moaned loudly, obviously audible. He thrusted in, surprising me again. I screamed, in total ecstasy. He pushed in and out, pumping his cock with my pussy. I came, soaking his cock and the area around it with my pussy juices. Oliver kept going, thrusting in and out of my leaking pussy. I moaned louder and louder as he went. Five minutes and another of my orgasms later, he finally came. I moaned and moaned as his cum filled my cunt. I plopped down on to the pillows, leaking out onto my sheets. It was 9 at night. I fell asleep in his arms.