tagTransgender & CrossdressersMaster's Degree in Crossdressing Ch. 01

Master's Degree in Crossdressing Ch. 01


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."


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?"

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