Master's Degree in Crossdressing Ch. 02

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A grad student submits to his addiction to girly things.
3.7k words
4.51
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16

Part 2 of the 2 part series

Updated 09/22/2022
Created 06/24/2014
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wifetoy
wifetoy
319 Followers

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 tanned, 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 search 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 virgin for real cock, 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.

Ben 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.

wifetoy
wifetoy
319 Followers
12