6 comments/ 37308 views/ 12 favorites Master's Degree in Crossdressing Ch. 01 By: wifetoy This series is the follow up to my earlier series "College Crossdressing Confessions." My wife forced me to make those confessions detailing my shameful addiction to wearing panties, pantyhose, and other girly intimates, and my panty pilfering ways in college. While I was making confessions to the public for the first time, my wife has generally been aware of those perverted deeds for many years. She has now ordered me to go further and reveal something in my past that I have been too ashamed to reveal even to her. She told me that she will be merciful if I am completely truthful and detailed in describing my depravity, but that my punishment will be severe if she feels I am holding back. ***** To my beautiful wife, I confess the following: After a wild post college summer travelling in Europe and interning in DC, I entered the MBA program at the University of Texas. I had some great people in my MBA class who eventually became life-long friends, but I was single and very interested in mingling with the undergraduate coeds. One of my good friends from high school was a rising senior at UT. Blair was a very cute girl next door type. Although I had always had a huge crush on her, I was securely locked in the "friend zone." Blair was a member of Kappa Kappa Gamma at UT and was living in the sorority house her senior year. The Kappas were one of the top sororities at UT and also had some of the most beautiful and accomplished girls on campus. Their sorority house was one of only two Greek houses that were actually on UT's campus. It was a huge old southern mansion. Once on campus, I dated a number of Kappa girls I met through Blair. Blair also invited me to several of the Mexican guest lunches that the Kappa's hosted every couple of weeks, so I got to know most of the girls living in the Kappa House. I love women in general and particularly beautiful women, so I welcomed these opportunities to surround myself with them. I did not end up dating anyone seriously, but had some fun dates and even a few fun sexual flings with some of the more willing girls. Most of these girls were extremely cute, and all of them dressed very well in the latest fashions. This, as you know from my college confessions, was particularly important to my secret girly side. While I enjoyed hanging out with these wonderful young women, I soon realized that there were far fewer opportunities in grad school for me to indulge my addiction to girls' panties and sexy intimates. Most of the girls I knew were either living in sorority houses with no access or were my grad school friends who usually lived off campus in apartments. Since we usually hung out in bars with the grad school crowd, I did not have access to their apartments either. My itch for wearing pretty panties and yummy lingerie, tights, and dancewear was becoming unbearably strong. My mind raced with possible solutions to my unquenched thirst for girly delights, but to no avail. By mid semester, I was having regular naughty dreams, such as being kidnaped by a sorority and forced to dress like a sorority girl. As Thanksgiving break approached, I decided to stay in Austin and catch up on my studying before exams. We had a week break, and the school was basically shut down. The campus was already a ghost town on Friday afternoon before Thanksgiving. I treated grad school like a job and was actually caught up on my studies, so I decided to take a walk late Friday afternoon to get some exercise. My route took me by the Kappa House. As I passed, I saw Ben, the regular evening guard sitting on the front steps of the house. I had gotten to know Ben during the fall because I was regularly stuck chatting with him while waiting in the Kappa House reception area for my various Kappa dates to finish getting ready and come downstairs. Ben worked as a campus police officer during the day before his regular night shift as the door guard at the Kappa House. He said he was divorced and lived alone so it gave him some extra money and something to do. Spending the evening around a bunch of very cute sorority girls probably was not so bad either. I waived to Ben and walked over to where he was standing to say hello. Ben said that the campus police were more lightly staffed over the holidays, so he always took off work and stayed at the Kappa House all week to guard it while it was closed, and the girls and the house mother were away for the break. He said it was pretty boring, but he made some extra money for Christmas. We chatted briefly, and I continued on my walk. A few moments after I continued my walk, I had a very naughty idea. I continued walking to a nearby convenience store and bought a twelve pack of cold beer and then began walking back toward the Kappa House. As I neared the house, I again approached Ben, gestured to the twelve pack, and asked: "Want to have a beer or two; I have plenty and am just going to drink them by myself at my apartment otherwise." "I would love to. We better go inside, however, I don't want to get fired for drinking on the job," he replied as he ushered me through the door and into the reception area. I handed him a beer and took one for myself. Ben took the rest of the twelve pack from me and put it in a small refrigerator near his guard desk. We settled in on some chairs in the living room. I did not know how my plan was going to go, so I started slowly. After about 10 minutes of small talk, I asked the very general question: "What is it like being able to work surrounded by beautiful sorority girls all of the time?" "The scenery certainly is nice. Most of them are really sweet to me, but I am not even sure they really think of me as a man in their midst. Some of them are bitchy and treat me like the help. I do get to see some pretty sexy things since I am virtually invisible to some of them. " Sensing a little opening, I said, "What are some of the hottest things you have seen?" "They prance around in their tights and leotards for aerobics class like I am not even in the room. There is also this one beautiful girl, who is a majorette. She is really sweet and will sit and talk to me. Earlier this week, she sat down across from me in her majorette costume and took off her boots and rubbed her feet. She was wearing those dance tights. I almost came in my pants. They will also just generally hop down the stairs to get something out of the kitchen late at night in only a t-shirt and panties like I am not even sitting there." "That must make you pretty horny and frustrated" I replied. "Man, you would not believe it. After my divorce, I just have not been able to get back in the game. Plus, none of these rich, stuck up sorority girls would give a campus cop the time of day. That applies to most of this town as well, so I have not been laid in forever. I haven't even had anybody touch it other than me. I am so hard up. The only thing I can do after being tortured from looking at these hot girls all night is rush home and take care of myself , if you know what I mean, but I am getting tired of that. I would kill for a piece of pussy or a blowjob." "I know what you mean," I agreed. "I can barely walk around this campus without having to duck into bathroom. " "You know it man," he replied. After a somewhat awkward pause, I decided to make my move. I could not figure out an easy way to say it so I just blurted it out "I will suck your cock if you will let me play around in one of the girls' rooms upstairs." "What?" I repeated myself. "Are you some kind of queer or something?" he immediately replied. "No!" I reassured him. "I just like to play in girls' panties and other things and thought I could trade a little access to one of the rooms for something that would take care of your problem. I promise it will be our secret, and no one will ever know." "What do you mean you like to play in girls' panties and stuff?" "It turns me on to wear panties and pantyhose and tights and stuff, and I am willing to give you a blow job to get access to one of the rooms upstairs. You can just close your eyes and pretend it's a girl." He hesitated and I tried to reassure him. "I will be real careful, and not mess anything up. No one will ever know." "It's a total mess up there anyway from the big sister-little sister party they had last night, and the maids come next Friday to do a deep clean before the girls get back, so I am not worried about the mess," he replied. "I just don't know about letting a guy suck my cock." He paused, sighed and said, "Well, as long as no one will know, I am pretty hard up, but I am not a queer..." "I know you're not, like I said, just pretend it is one of the girls" "I guess I can let you up there, but only one room and only for 30 minutes and then I am coming up to get my blowjob. " He led me upstairs and used his master key to unlock the first room from the stairs. "Have fun doing whatever you do; I will be back up in 30 minutes. If you back out on me, I will kick your ass." This room happened to be my friend Blair's room with her name and party pics on the door, along with her roommates Leslie and Margaret. These girls all had the reputation as being "good girls," but I love classy femininity, so I was still excited about what I might find. My heart raced as I entered the girls' room and shut the door. The room was somewhat trashed with unmade beds and clothes strewn about, but that clearly worked to my advantage. Each girl had a day bed against the walls with storage underneath, and built in dressers and closets for each. I inhaled the delicious mixture of perfumes and powders and squeezed my nipples through my shirt with heady desire. I started with Blair's dresser, and nervously pulled open her top drawer. It was packed with pretty panties. While Blair was a preppy girl next door type on the outside, her panty drawer revealed that she was now a sexy grown woman. I pulled out a pair of white lace bikini panties. The lace was heavy and soft with thin strips on the side. I immediately stripped off my walking clothes and stepped into Blair's panties pulling them up over my ass and tucking my cock into the front. They were gorgeous and tightly hugged my cock and firmly cradled my balls in girly lace. I opened her next drawer and found her sock drawer filled with feminine delights. I pick up a pair of dainty lace anklet socks and pulled them on each foot stretching them up my ankle and folding down the cuff. I paused and sprayed on some of her perfume. It was a rich floral scent that I knew well, and I relished how pretty and feminine it made me feel. I opened the next drawer, which contained her tights, slips, and camisoles. After gently digging through the tights and slips, I found a very sexy pink microfiber body suit. It was soft, pink, and wonderful. I wondered if my sweet high school girl next door crush had been turned into a little vixen by her current boyfriend. I had to wear it. I stripped off the panties and put them in my take home pile. I stepped into the scrumptious pink bodysuit and pulled it up my body, putting my arms through the delicate spaghetti straps. This was before bodysuits became trendy, and this was more intimate lingerie like a teddy than a fashion accessory. I admired Blair's teddy on my body in the mirror. It was sexy, but also subtle and classy. The light pink microfiber clung to my body like a second skin. I sat on Blair's day bed, reclined up against the fluffy pillows and admired the feminine look of the soft teddy. I lifted my legs into the air. I imagined Blair dressed in the teddy and the lace anklet socks posing for her boyfriend both freshly innocent and naughty in one tight ass package. Rubbing my cock beneath the soft pink microfiber, I was tempted to pull my cock through the leg openings and bring a creamy end to this delightful romp. I held myself in check, however, knowing that I would lose "momentum" if I came. Realizing that I was running out of time, I moved to Leslie's section of the built in dressers still wearing the luscious pink teddy. Leslie was a very pretty redhead who was also fairly conservative in her dress and at least played the role of the nice girl. She performed in the University's Broadway style review and was a very talented performer. I was pleasantly surprised when she showed up a Halloween party that my friend's fraternity hosted wearing a black unitard with cat ears, black high heeled pumps, and nothing else. She looked fantastic and seemed to enjoy the attention, revealing a secret sexy side. It was so hot knowing that she was prancing around the party with nothing on under the skin tight unitard. She had proudly put up a party pic on her door from that night. She looked smoking hot in the picture, posing with her hip out, and puckering her very red lips. I opened Leslie's top drawer and added a few pair of her dainty satin panties to my take home pile. I then moved to her second drawer, which appeared to contain exercise and dancewear, my favorites. I rummaged through the leotards and tights before my hand touched heavy black spandex. I realized that it was her black unitard from the previous month's Halloween party. I was thrilled. I stripped off the pink teddy and the socks and added them to my take home pile. I stepped into the unitard and pulled it up my body, carefully stretching it so that it would fit. I struggled to fit my arms in the long spandex sleeves and adjusted the unitard, tucking my cock between my legs so it would not show and adjusting the stirrup bottoms around my feet. I found some soft white ankle socks and pulled them over my feet. I looked in the mirror and felt exquisite pleasure at my find. I noticed the headband with the cat ears hanging on her lamp shade and placed it on my head. Looking in the mirror, I thought something was still missing. I looked on the counter in front of Leslie's make up mirror and found some bright red lipstick. I hurriedly applied a heaving coat to my lips and admired myself in the mirror. I felt deliciously girly as I stretched out on Leslies unmade bed and admired my spandex coated body, almost wet looking in its shiny blackness. The unitard hugged my body from every angle and felt great as I slid against Leslies soft sheets. I was excited beyond belief. I then heard Ben climbing the stairs and felt that nervous feeling in the pit of my stomach as I realized it was time to pay the passage for my naughty adventure. I playfully posed against the head of the day bed as Ben entered the room. He laughed as he saw me. "You are a little sissy," he teased. "Come over here and suck my cock, little girl, I have been thinking about this since you came up here," he said, as he pulled down his pants and sat down on Blair's bed. I started to get off of Leslie's bed and walk over, when he barked, "Crawl, bitch!" I went to my knees and crawled the remaining ten feet over to where he was sitting. I had never sucked a cock before, so I was nervous, but embarrassingly excited, as I reached for his cock which was semi-hard and hanging before my eyes. "Don't touch it, use your mouth only," he warned. I leaned forward from my kneeling position like I was bobbing for apples and took the head of his cock between my lips. His cock had a big plumb shaped head with a pronounced ridge where the head met the shaft and appeared massively thick, even in its semi-erect state. I sucked the tip into my mouth, trying to control it with my lips as my lips popped over the head and slid about 2 inches down his shaft. I pulled my head back to try to slide my lips back and forth, but the head slipped from my mouth and slid down my chin glistening with my saliva. I bent forward and sucked the head into my mouth again pushing my lips further down the shaft as I felt his cock swell in my mouth. I paused and swirled my tongue around the head of his cock, tasting the saltiness of his flesh and finding it more satisfying than I would like to admit. I slid further down his shaft, taking four inches of his cock into my mouth as the tip crowded the back of my mouth. I stifled my gag reflex and squeezed my tongue toward the roof of my mouth to squirt his cock back out, hugging it with my lips and cherishing his soft moan of pleasure. His cock grew hard, although the head remained spongy and supple in my mouth. I felt so wonderfully subservient and complete, squeezed into Leslie's black spandex second skin and servicing his cock. I began to develop a rhythm sliding my lips down his shaft and sucking his cock as far into my mouth as I could, before pulling back and sliding it back out, swirling my tongue around it with each stoke. More moans of pleasure greeted my quickened pace, and I tried to relax my throat to take more of his cock with each stroke. I raised my eyes to look up at Ben and saw his eyes closed and his face filled with pleasure. Sucking strongly, I pulled the brackish precum from the tip of his cock and mixed it with my saliva thoroughly wetting his cock and surrounding it with the soft warmth of my mouth. As I repeated the motion down his cock, I was now relaxing my throat enough to take three quarters of his thick seven inch length into my mouth before pulling back, leaving a ring of bright red lipstick to mark my cock sucking progress. His breathing became heavier as I repeated the motion trying to take more of his cock into my throat with each push down his now steel stiff shaft. I felt both his hands touch the top back of my head and wondered what he was fantasizing about as I looked up at his tightly squeezed eyes,. I kept sucking and swirling trying to bring him off into my mouth, a challenge that was becoming embarrassingly pleasurable. My cock had now shifted from the downward grasp of the unitard and was engorged, pushing forcefully against the spandex holding it against my body. The mystery of Ben's thoughts revealed itself when he began to repeat "That's right, suck my cock Leslie, suck it beautiful, suck my fucking cock you prissy bitch." Ben's hands became firmer as they rocked back and forth with the motion of my head. His body stiffened, and he grunted loudly. I felt the spasms as the sparse leakage of pre-cum was replaced by spurts of salty, slightly soapy semen squirting against my throat. I have always hated it when girls stop sucking on the first spurt of cum, so I continued sucking up and down his cock catching the spurts and then trickles of cum in the back of my throat and then swallowing the pooled cum as I continued to service Ben's cock until it began to slowly soften in my mouth. I felt a rush of excitement from having satisfied this man sexually with my mouth like a real naughty sorority girl. That feeling combined with the girly feeling from the unitard had me rock hard straining hopelessly against the black spandex. I pulled my mouth off of Ben's cock and wiped the spit and traces of cum from my lips. As Ben lay back on Blair's bed still breathing heavily. "Damn, you can suck a cock better than any girl I have ever had." He finally got up and pulled up his pants and left the room. "You have five minutes to get cleaned up and get out of here," he added. Still trembling with sexual excitement, I peeled off the unitard, quickly pulled on Blair's lace panties that I had been wearing earlier, although they barely contained my raging hard on. I got dressed in my walking clothes. I grabbed an empty shopping bag from the closet and added all of my finds to take home pile and placed them in a bag to take home with me, eagerly anticipating the release I would give myself as soon as I walked into my apartment. I composed myself and walked down the beautiful staircase to the foyer where Ben was sitting. He looked up as I walked down the stairs. "Where do you think you are going with that bag?" Master's Degree in Crossdressing Ch. 01 I replied that I just wanted to take a few things with me. "That was not part of the deal," he said. "You are not taking anything with you." "Please," I begged. "Just a few things." "Nope, but I have been thinking. I am stuck here alone for the rest of the week, so I will make you a deal. You can walk out of here now, go home, empty handed of course, and beat your sissy meat to your heart's content. I will never mention what happened tonight to anyone. However, you can come back in the morning, live like one of the girls in the house, and be my bitch for the rest of the week. If you do come back, you cannot touch your cock before you return, you must bring only the clothes on your back, and you must prepare yourself by shaving your body completely smooth like a good girl. If you do come back, you can do anything your sissy ass wants to do upstairs, but you will be mine to use for the rest of the week. " With that surprising proposition, he reached in the bag and grabbed a pair of sating string bikini panties. "Wear these if you come back so I will know you are fully my sissy bitch." "Now get the fuck out of here." I was flustered with doubt when I scrambled out the door and began my walk home, my cock shifting in the lace panties under my thin running shorts. I was troubled by how much I enjoyed sucking his cock and how womanly it made me feel along with Leslie's black unitard. I kept walking torn between retaining the last shreds of my manhood and the girly delights waiting on the upper floors of the Kappa House. Master's Degree in Crossdressing Ch. 02 This confession is the second chapter of a follow up series to my earlier series "College Crossdressing Confessions." My wife forced me to make those confessions detailing my shameful addiction to wearing panties, pantyhose, and other girly intimates, and my panty pilfering ways in college. While I was making those confessions to the public for the first time, my wife has generally been aware of those perverted deeds for many years. She has now ordered me to go further and reveal something in my past that I have been too ashamed to reveal even to her. She told me that she will be merciful if I am completely truthful and detailed in describing my depravity, but that my punishment will be severe if she feels I am holding back. I suggest you read the first chapter of this series and the entire earlier series so that your will understand the context of my confessions. ***** As I walked across the abandoned campus, the crisp morning air felt strangely wonderful on my smoothly shaved legs. The silky running shorts only served to exacerbate the feeling as they caressed my shaved legs and the satin panties I obediently wore underneath as I approached the Kappa House. My stomach felt nervous with anticipation, but those nerves were eclipsed by the throbbing excitement of my panty bound cock. These feelings grew more intense as I climbed the steps and approached the door. I knocked hesitantly. Ben answered the door. "So you are a horny little bitch." He ushered me into the reception room. "Take off your shorts and show me" I felt embarrassed, but warm inside, wet your pants warm (those of you who are truly perverted know what I mean). I slid my flimsy pink running shorts down to my ankles and stepped out of them. Ben ordered me to turn around and ran his hand up my smoothly shaved leg to the satin panties. "You are almost a real girl in those panties. " He unbuttoned his pants and pulled down his zipper. "Take out my cock and suck it while I tell you how it's going to go this week" I in a nervous daze, I obediently kneeled on the floor, took his cock out, placed my lips over the head of his semi-soft cock and formally accepted my role as his sissy sorority slut. As I gently sucked his cock to life, he began to speak: "You are going to be my sex toy for the rest of the week. As long as you please me, you can have the run of the upstairs. The master key to the rooms upstairs is on the table by the stairs. You can wear anything you want of the girls. You may not cum and you may not wear any boy clothes. You will be available for me at any time. You will be dressed and prepared for me to use. I am not gay, so, when I am with you, you will assume the name of the girl whose clothes you are primarily wearing. If you are a good little slut, you can stay and enjoy your sissy perversions. If you are not, I will kick your pantied ass out the door for all to see. Do you understand?" "I answered a muffled "yes sir" as he thrust his now hard cock deeper into my throat. After a few minutes of eager sucking, he pulled his cock out of my mouth. "I have to go by the station for a couple of hours. I am going to save that load for your girly ass. When I come back, I want you face down on Catherine Carlin's bed with your ass in the air ready for my cock. She is a hot little piece of ass, and I am going to enjoy fucking her. I am sure you can find something in her room to help you get in character." With those instructions, he tucked his swollen cock into his pants, zipped up, and headed out the door. I pulled my running shorts up over my panties, grabbed the master key, and headed upstairs to crossdresser Disney World. Only in this case, I had to pay for my E-Ticket with my virgin ass and my newly christened sissy cock sucking mouth. My pantied cock had swollen with the mention of Catherine Carlin's name. She was a beautiful tall thin blond from Houston. I met her the first week of school when I went day drinking with some Kappa friends after rush was over. I remember her sitting at the table in the afternoon sunlight wearing a short white shirt dress, ankle socks, and white oxfords with ribbons for laces- one of the top sorority girl trends that year. I loved the look, which was so pure and innocently feminine. I was mesmerized by her as she sat at the table with her perfectly tannned, smooth legs crossed and dangling one of her ribbon laced oxfords from her toe. The cuffed tops of the thin white ankle socks set off her tan perfectly. Once upstairs, I had two hours to immerse myself in glorious girlhood. I explored the second floor carefully. I found Catherine's room and the bathroom she shared with her suitemates' room on the other side. I spent a few minutes exploring the room, looking at all of the sorority pictures around the room. As I looked, I was mesmerized by the mixture of feminine scents from perfumes and lotions, etc. I was soon making my way through the dresses in Catherine's closet and happily discovered the white knit shirt dress that first triggered my adoration of her feminine beauty. I knew then this was the dress I would be wearing when Ben claimed my anal virginity as payment for the privilege of enjoying this wonderful world of womanly delights that I craved so much. I wandered into the bathroom, amazed by the number of wonderfully girly beauty products lining the counter. I decided to start with a shower to make sure I was shaved completely smooth. I peeled off my t-shirt, running shorts, and panties, pausing briefly before slipping off the satin panties to admire the sissy scene and my hairless body in the mirror. I used the girls' shampoo and conditioner on my hair. The pretty scent was tantalizing. I shaved my body carefully again to make sure it was completely smooth and I did not miss any spots. I lathered my hairless body with sweet scented bath wash, marveling at the smoothness of my skin. After my shower, I dried off with one of the girls' fluffy pink towels and wrapped myself in Catherine's Kappa towel wrap with her name stitched on the front under the KKG Greek letters. I already felt like such a super cute sorority girl! I applied Catherine's powder fresh scented deodorant and some body powder, before adding a few sprays of her beautifully scented perfume. Sublimely showered, smoothly shaved, and perfectly perfumed, I hung the towel wrap up and wrapped myself in Catherine's luxurious, thick robe. Its heavy, soft warmth heightened my feminine feelings as it caressed my silky, shaved skin. I sashayed into Catherine's room and began searching her drawers for the perfect pair of panties. As I walked the slight cool draft kissed my smooth, bare bottom under the robe. As I should have expected, the fabulously feminine Catherine had plenty of pretty panty possibilities piled in her top drawer. My clitty buzzed with excitement beneath the fabulously feminine robe as I ran my hands through Catherine's silky delights looking for a particularly prissy panty pair. I soon found the prized panties for my afternoon assignment. The bright, shiny virginal white satin fabric was cleanly shaped into a subtly sexy string bikini- fun, flirty, and feminine. Catherine's family wealth allowed her the finer things in life, and this privilege apparently provided prime panties and lingerie. These were no cheap department store panties. They were small and delicate, but with rich, thick, soft satin, heavy in my hands. I leaned down and spread Catherine's perfect panties with my fingers, opening the legs and stepping further into her femininity. I pulled my hands upward sliding the soft satin string bikini panties slowly up my legs to my hips. I adjusted the strings on my hairless hipbones. The buttery soft fabric hugged my clitty and nasty balls tightly against my body. The panties fit me perfectly like a girly glove, giving my ass a squeeze of satin control. I walked back in the bathroom feeling even more feminine and complete. Looking in the mirror, I needed to do something for my hair, which was shaggy and longish like college boys are prone to wear it. I filled my palm with the hair mouse from the counter, brushed my hair back so it would look like a sleek, short cut like Linda Evangelista wore at the time. It looked pretty nice and gave my face a more feminine look. I then took some mascara and pulled the brush through my lashes as I had watched my sister do on many occasions. I carefully applied eyeliner, doing an ok job given my lack of experience. I smoothed a little blush on my cheeks and applied a wonderful bright pink shade of lipstick to my puckered lips. It was not perfect, but I definitely looked more feminine, and more importantly, felt it. I went back into Catherine's room looking for other fun ways to further my femininity. Spying a line of fingernail polish on her dresser, I selected a hot pink shade and carefully painted my toenails and fingernails, adding yet another layer of girly gloss. While I waited for the polish to dry, I relaxed on Catherine's day bed, luxuriating in her soft robe and went through her scrapbooks. They were filed with sorority and fraternity party picks, candid pictures from around the sorority house, and pictures of beautiful sorority girls in bikinis on spring break. As I looked through the scrapbooks, I was torn between lusting for the girls and wanting to be dressed like them - a common crossdresser's dilemma. Soon my nail polish was dry, and I decided to get dressed. I returned to Catherine's drawers and found a white lace bra. Catherine was a B cup so it actually kind of fit me, in addition to giving me that tightly bound feeling of feminine compression I have since come to love. I knew from my sister's routine that a proper girl always puts her socks or other legwear on before her dress so as not to wrinkle the dress, so I searched Catherine's drawer for some anklet socks to complete the look. I quickly found a shimmery pair of thin white anklet socks, just like the pair Catherine was wearing when I met her. I pulled the dainty socks over my feet and folded the tops over to form a pretty cuff just above my ankle like all the girls were doing at the time. I admired my newly feminized body in the mirror standing in Catherine's beautiful lace bra, satin panties, and white ankle socks. I toyed with my nipples beneath the lacy cups of the bra, enjoying the extreme heightened state buzzing through my lingerie clad body. I pulled the knit dress over my head, put my arms through the cap sleeves and pulled the dress down my body. I straightened the dress in the mirror and was amazed at how beautiful and sexy it looked. The dress was a drop waist dress that flared out just below the waist. It was short, coming only to the upper middle of my silky smooth thighs. I looked gorgeously girly in this dress. I was beyond excited as my heart raced and my clitty surged with excitement in its pretty panty prison. I needed some shoes to complete the outfit. I found Catherine's white oxfords in the closet, but they were much too small. I then went from room to room looking for a pair that would fit, like a sissy Cinderella in searche of the glass slipper. Finally, I found Susan Stanton's room. Susan was a gorgeous blonde who was 6' 1''. She came to Texas on a volleyball scholarship, but soon gave it up for the life of a beautiful sorority girl. She was stunning and carried her height with pride, unafraid to wear heels. She had also attracted some attention from the modeling world, spending the past summer in New York. I hit the jackpot. Susan wore a size 11 shoe. I found her pair of white oxfords, which were like a uniform at the time in that every girl had a pair. I squeezed my foot into the shoes aided by the lack of friction from the thin, satiny ankle socks. They were tight, but I could walk in them. My look was now complete. Returning to Catherine's room, I admired myself, posing in front of the mirror. I looked pretty decent and felt incredibly sexy and deliciously naughty in my outfit. My body buzzed with sexual tension, but I also felt an inner peace as if I was meant to dress like a beautiful girl. I sat on the bed, crossed my legs and posed some more in the mirror, beside myself with excitement. As I relaxed on the bed, I remembered that Ben would be back in a matter of minutes, and it was time to prepare my girly self to receive his cock. I knew I had to properly prepare my virgin hole so he did not split me in half. I walked into the bathroom and noticed some Vaseline on the bathroom counter. While a real cock virgin, I had been sticking things up my ass since middle school and knew just what to do. I found a midsize round bottle of Pantene shampoo that was shaped kind of like a dildo. I carried my new toy and the lube back to Catherine's bed and climbed on her pink duvet. I reclined on my back and pulled my legs into the air, exposing my ass to the mirror. Pulling my panties aside to access my virgin hole, I smoothed the Vaseline around my smoothly shaved hole trying to relax my sphincter muscles. I began dipping my finger into my hole with each pass as I relaxed and opened up. Feeling naughty and warmed up, I smeared Vaseline on the tip and length of the Pantene bottle and pressed the top against my well-greased hole. I increased the pressure until my asshole gave way, opening to engulf the tip of the bottle. I began slowly fucking myself with the shampoo bottle, reveling in the sensation of fullness and the pressure on my prostate in my orgasm denied state. Just as the pleasure began to overcome the mild pain caused by the stretching of my now stuffed hole, I heard the front door close. I quickly removed the Pantene bottle from my ass and set it down beside the bed, confident that my ass was now prepared for his taking. I adjusted Catherine's panties back into place, turned over on my knees with my pantied ass in the air and waited to pay my debt to my violator. As I heard his footsteps in the hall, I lay my head on Catherine's sweet smelling pillow and thrust my pantied ass further in the air presenting it for his arrival. The last few seconds of waiting for my deflowering seemed agonizingly long as my stomach boiled with butterflies and my clitty swelled beneath the grasp of the satin fabric of Catherine's panties. I felt completely feminine, smooth, perfumed, dressed sublimely, and also vulnerable and exposed in my girly softness. I heard him enter the room. He did not speak. His weight compressed the end of the bed as he sat or kneeled. I felt him first grab and then roughly handle my upturned pantied ass. I arched my back and extended my ass further to meet his groping hands, offering my ass to him. After a few moments experiencing his strong hands as Catherine may have enjoyed with another boy in these same clothes, his weight lifted off the bed. I heard the sound of pants being unzipped, the metallic sound of his belt unbuckling, and the faint friction of his jeans being removed. I was almost quivering with anticipation as I felt his weight again compress the end of the bed as he moved toward his feminized prize. I felt his hands on my smooth ass again. He rubbed my pantied ass for a few seconds before I felt him pull the panties to the side, but leaving my clitty still trapped in satin bondage. The tip of his rock hard cock bobbed against my well-greased hole. I felt him move his right hand from my ass to guide his cock to its tight target. The head of his cock began to push more firmly against my hole. I tried to relax to accept his invading cock. I felt my whole gradually open as the bulbous head of his cock pop through my sphincter ring. I gasped at the suddenness and the jolt of pain even though I was well prepared to accept his cock. I bit down on Catherine's pillow until the endorphins released in response to my stretching hole overcame the pain. He paused mercifully as I became accustomed to the head of his cock, gripped tightly by the ring of muscle at my opening. He moaned. Ending his pause, he began to slowly push his fat cock into me. I knew he was pretty big from the night before, but he felt huge as he stretched my bowels for the first time. With his initial push, I pushed up on my arms and contorted my body in an attempt to accept the length and the substantial girth of his cock as he impaled me. My mouth fell open involuntarily, and I let out an involuntary moan as he took me. I felt a sense of accomplishment as I felt his body push into mine and press my ass cheeks, indicating that he had "bottomed out." He briefly held his place deep within me allowing me to adjust to the invasion. He slowly began to withdraw most of his unyieldingly hard cock, before causing another gasp and throaty moan from my lips as he thrust back into me with the full length of his impressive member. The initial pain had turned to a wonderful fullness as he spread and stretched me as he would a woman. He began steadily pulling out and thrusting into me, fucking me like the girl I had temporarily become. I looked up and caught a glimpse of his face in the makeup mirror on the small table by Catherine's bed. His eyes were tightly closed, and I felt a feeling of womanly gratification at the pleasure he was taking from my smooth, wanton bottom. I lowered my head and looked back beneath me and between my legs. The growing fulfillment I was feeling from his thrusting cock was intensified by the view of his knelling body between my smooth legs, the thin frilly anklet socks, and the girly innocence of the white, ribbon laced and bow tied oxfords. Bill began to thrust in and pull out of me more quickly, his bulbous cock head skating across my prostate and bringing me even more pleasure in my orgasm denied state. My clitty swelled from the naughty internal stimulation pushing against the gentle, but firm control of Catherine's white satin panties. I turned my head to the side, away from the wall, and saw the full, rudely sexual panorama of the rough fucking that Ben was giving my newly feminine self in the mirrored closet doors. The innocence of the cute white dress, bright white satin panties, and girly socks and oxfords was obscenely shattered by the powerful naked man plowing his orgasm hungry cock into my virgin ass. The visual intensity of the most submissive act of my giving of the most intimate treasure of my girly being to a man was extremely powerful. Allowing him to claim me in this way, prepared, dressed, and perfumed, like a beautiful sorority girl gave me a sense of completeness that is difficult to describe. His pace quickened further in the mirror and correspondingly in the reality of my stretched, but accepting hole. I felt and saw myself begin to push back into him, responding to his fucking by fucking him back, no longer a passive receiver of his hard cock. I had experienced many objects in my hungry ass, but nothing compared to real living hard cock of this man pumping himself into me. I was astonished by the view and the feel of his relentless pounding while he chased the initial wisps of his climax in the distance of his sexual journey to the beginning contractions of his manly goal. The rhythmic slapping noise from his repeated filling of my being became more rapid and his full balls lashed my pantied package again and again. I wanted him as Catherine would want her man. I wanted to be the source of his ultimate pleasure. I wanted to pull it from his pounding cock; to have it fill me, mark me, and claim me as his conquest. I squeezed my muscles around his cock, resisting his thrusts in and pushing him out to milk him in pursuit of his pleasure. His breath quickened, and he let out a long groan as our efforts were rewarded with the climatic prize. He maintained his thrusting as he milked his cock in my ass through the final contraction before I felt his weight collapse against me. Spent, he remained for a few moments before pulling his softening cock from my used ass and going silently into the bathroom. As I lay on Catherine's bed, I heard his footsteps going down the stairs. Master's Degree in Crossdressing Ch. 02 I remained on the bed for almost twenty minutes, used and filled with his seed, but in a perfumed cloud of feminine fulfillment. I was now not only dressed like a young woman, but fully known as one by a man. My education was only beginning.