College Crossdressing Confessions

Story Info
My wife makes me confess my college crossdressing secrets.
3.4k words
4.19
118.9k
44

Part 1 of the 4 part series

Updated 10/21/2022
Created 09/08/2013
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
wifetoy
wifetoy
319 Followers

My wife's control over me insures that I have no secrets from her no matter how depraved my hidden desires. She delights in my need to live under her feminizing control. As part of my training, she has ordered me to confess my prior deviant acts to the world. In this series, I confess my past experiences as a panty thieving college cross dresser. I have changed some of the names, but the rest of the confessions are, sadly, true.

As indicated in a previous story, "Wife in Control Ch. 3", I discovered the pleasures of wearing my sister's panties, pantyhose, ballet tights, and other soft and girly things as a teenager. These panty pleasures culminated in my moving into her old room as an eighteen year old high school senior and playing in her panty drawer and closet on a daily basis. I relished the pleasures of that year rubbing my rock hard cock with her body lotion, while admiring my pantied ass and legs softly covered in the various hues of the pantyhose and tights she left behind when she went off to college. It wasn't that I wanted to be a girl or saw myself as trapped in the wrong body. Instead, I coveted the opportunity to wrap myself in her femininity. My sister had a sweet, feminine beauty that I adored. I enjoyed the feeling of simply wearing her most feminine lingerie, hosiery, and even the occasional dress almost as much as the orgasmic rush of pulling my cock over the band of her pantyhose and jacking off while pointing my hose covered toes in the air. Wearing her feminine clothes gave me a certain intimacy with her that was as addictive as it was difficult to explain. Outside of this kink, I was a very aggressive hetero young man who was relatively successful in my pursuit of the girls in my affluent and somewhat sexually conservative social group.

In 1986, I graduated from high school and headed off to college at SMU in Dallas leaving behind my special relationship with the silky contents of my sister's panty and hosiery drawers. Other than occasionally pilfering a pair of panties from the dryer in the dorm laundry to jack off in when my roommate was out of town for the weekend, I suppressed my urge to frolic in women's "unmentionables" as my grandmother called them. Instead, I turned my attention to chasing the girls I encountered on the SMU campus. SMU has a very wealthy student body, and the coeds were very beautiful, fashionable, and well maintained. The daddy's little girl syndrome was alive and well, but there were also many very cool, fun young women who were as smart as they were beautiful. I was an all American looking guy and pledged a top fraternity, so I was around some of the most beautiful and accomplished women on campus on a daily basis. While I had some sexual success and was great friends with many of these beautiful sorority girls, I never connected with any of these women on a long-term romantic basis. In short, I was a good friend and a fun date. I had a lot of short term flings, but nothing serious.

My sophomore year, I lived in an apartment with three other guys, so my life was more of the same. I was a good student, but I had a great time as a typical wild fraternity boy, although I would like to think without the douche bag and asshole connotations. I kept my fantasies of playing in the panty drawers of those cute sorority girls to myself and did not act on them. At the end of my sophomore year, however, that old itch resurfaced.

Right after we finished exams, one the girls who was a "good friend" invited me to come to her hometown to be her escort for the weekend of a charity ball. Lauren was a tall, attractive girl, but we did not have a sexual connection other than a few drunken make out sessions. She wanted a fun date without the drama of dealing with a boy she did not know well. I was happy to oblige in return for free drinks and a fun party. I stayed in the guest room of her parent's luxury condominium in downtown Houston. There was a cocktail party on Friday night before the Saturday night ball. She looked beautiful in a short cocktail dress with sheer hose and pretty black satin pumps (keep in mind this was the late 1980's), and we had a great time without the pressures (or the pleasures, unfortunately) of romantic entanglement.

On Saturday, while she was out shopping with her mother, I went to take a shower in the bathroom shared between Lauren's room and the guest room. As I undressed, I noticed the familiar sight of the leg of a pair of pantyhose hanging over the side of the waste basket. Lauren's pantyhose had a small run in them, and she had thrown them away. Knowing I was alone in the house for a while, that old urge came over me. I sat on the cold marble floor of the bathroom and put on the pantyhose, pulling them carefully up my legs. They were very luxurious sheer to waist pantyhose and felt great on my legs as I pulled them high up my above my waist.

In a rush, those old familiar feelings returned as I admired my legs covered in the silky, shiny, evening hose. As I stretched out my legs, I could feel the cold marble floor on my ass through the sheer hose. After savoring the feeling of my hose covered legs for a few minutes on the floor. I reached up on the vanity and grabbed a bottle of Lauren's body lotion. I squeezed the floral smelling lotion into my hand, pulled the waist band of the hose down to expose my now hard cock, and began to stroke my cock. It was incredible. I thought of Lauren in her pretty dress wearing these very same pantyhose just a few hours earlier. I imagined wearing the dress and her black satin stiletto pumps. The feeling of experiencing her femininity and the beauty of her hose covered legs by wearing her pantyhose was incredible. As I stroked myself, I leaned forward in the sitting position so my asshole came in contact with the cold marble floor through the sheer pantyhose. I pushed my sphincter out to maximize the contact with the floor and rock my body so my hose covered ass slid back and forth on the marble floor. The pantyhose and the sensation of the cold floor on my asshole drove me over the top. I spurted powerfully in my cupped hand as I came violently, shaking while I continued to stroke my cock through the end of my orgasm. I was spent, but I knew, like an addict, my suppressed fetish had been reawakened.

When I arrived back in Dallas after the weekend, my roommates had already moved home for the summer. Still buzzing from my rediscovery of the joys of pantyhose and alone in the apartment, I went on a search mission. I walked to a large apartment complex near my place that was popular with female students and entered the laundry room after surveying the area to make sure no one was around. I quickly checked the machines and soon found a treat. In one of the dryers, I found several pair of white string bikini panties and a mesh hosiery bag containing a pair of white pantyhose. While I had always been an honest person and would not normally steal anything, the excitement of my reawakened fetish overcame any sense of morality. With my heart beating faster from the rush of potential discovery and the naughty thrill of playing in the panties and stockings, I quickly grabbed a pair of the panties and the white pantyhose, shoved them in my pocket, and rushed home.

Safely locked in the apartment, I breathlessly undressed and pulled on the panties. They were made of real silk, which I had never encountered before, and felt very tight as they cupped my cock and balls in feminine softness. I was so turned on that I almost fell down as I hurriedly pulled on the white pantyhose and pulled them up my legs. They felt incredible on my legs and around my ass and cock. I admired myself in the mirror, posing like a hot young sorority girl. Crazed with lust, I walked to the kitchen area and grabbed a knife. I pulled the panty hose and the panties down to my thighs and cut a slit in the pantyhose and the panties, splitting them from the crotch panel backward a few inches. I pulled the panties and the pantyhose back up and pulled my cock and balls through the slit. I was rock hard as I grabbed some lotion off of my dresser and climbed on the bed. With my legs stretched out in front of me, my lower half looked like a sexy young woman, except of course for the stiff cock sticking up from the crotch of the pantyhose. I crossed my legs and rubbed them together enjoying the feeling of my silky legs sliding easily across each other. I was in pantyhose heaven as the girlish feelings I remembered so fondly from my sister's bedroom came rushing back.

As I began to rub the lotion on my cock, my eye caught my umbrella sitting against the door frame. It was broken, but I had not bothered to throw it out. Eyeing the wooden handle of the large golf umbrella, I had a particularly depraved idea. I stood up and walked across the room, further titillated by the sensation of my hose covered feet sliding on the carpet as I walked. I grabbed the umbrella and brought it over to the bed. I rubbed a large amount of lotion over the wooden handle, which was about 6 inches long and was thick with four raised knobs to form a natural hand grip. I turned over on my knees with ass pointing to my wooden headboard. I reached back and ripped the hole in the crotch of the pantyhose wider to expose my asshole. Propping the tip of the umbrella on the headboard, I reached between my legs and lifted the well-greased wooden handle through the slit in the pantyhose and the panties to rest it against my asshole. Returning my hand to my cock, I pushed my panty covered ass back against the umbrella handle forcing the first knob on the end of the handle into my ass. It hurt at first as it forced open my sphincter, which had apparently forgotten the experience of my early anal adventures in my sister's room. Soon the fire subsided as my asshole relaxed to accommodate the invasion.

I began stroking my cock with the lotion and pushed back on the umbrella handle impaling my ass further over the next two knobs. Then, I started rocking back and forth on the umbrella handle which caused it to rub against my prostate as the last knob stimulated the rim of my asshole, stretching it open each time I rocked back. It felt incredible. I felt an orgasm building up inside of me and surrendered to the intense dual stimulation of my cock and ass. I stroked furiously as I rocked back and forth, fucking myself on the umbrella handle. My ass contracted around the handle as my orgasm seemed to sweep over me in a wave launched deep within my bowels. With cum spurting uncontrollably on the bed, my entire body shook with exquisite pleasure with each successive orgasmic wave. Spent, I slid the umbrella handle out of my ass and fell to the bed. As I lay on the bed in the stolen panties and pantyhose, the post orgasmic lull exacerbated my feelings of guilt over my theft, and I promised myself I would not do it again. I threw the umbrella and the panties and the pantyhose in the dumpster behind my apartment and went to bed.

The next morning, I awoke horny once again and sad that I had not saved the evidence for one more wearing. Before I had a chance to stroke myself to relieve the urge, Lauren called to see if I would help carry a few of the heavier items as she moved out of her apartment to go home for the summer. She was a good friend, and her parents had spent a lot of money on me the past weekend so I readily agreed.

Lauren lived with 3 other girls in a house off campus, but was moving out because she was spending the fall semester in Europe as was the tradition for many wealthy SMU coeds. Two of her roommates had already moved home for the summer, but her third roommate, Leslie, was going to summer school so she had just gone home for a couple of weeks and had not moved out. Leslie was a beautiful 5'7" blonde girl with a tight athletic body. I did not know her that well. She had the reputation of being a rich bitch, but Lauren said she was just quiet. Whatever the truth of that debate, it was undisputed that she was smoking hot. She was still head over heels for her boyfriend from high school who went to another college so she never went out, sadly depriving me and my fellow male students of her beauty and her body.

I arrived at Lauren's house as she was packing up boxes and began carrying her stereo and some furniture out to a trailer that she had rented. After I made a few trips, she announced that she needed to go to the store and get some packing tape. She told me just to stay there and watch her place for a few minutes so she did not have to lock up. In my horniness, my remorse from the night before faded, and I decided to take a quick look around. Laurens stuff was mostly boxed up and the first two drawers of her dresser were empty when I hurriedly opened them, my hands shaking with excitement and sexual adrenaline.

The third drawer was filled with shorts and t-shirts which was no help at all. The fourth drawer, however, contained her aerobics clothes. My heart thumped with excitement as I ran my hands through the spandex leotards and tights in various colors. My fear of getting caught since Lauren knew I was here alone overcame my desire to pilfer the entire drawer so I quickly grabbed one of two pairs of shiny black Lycra tights and shoved them in my pocket.

Knowing that Lauren would be back in a few minutes, I moved quickly into Leslie's room. She had only left to visit her parents the day before so the scent of her perfume and various lotions and powders lingered. Fighting the intoxication of the feminine surroundings, I opened her first drawer, which was her panty and sock drawer. The drawer mainly contained cotton bikini panties in assorted colors, which did not scratch my particular itch. I did, however find a pair of white satin string bikini panties and shoved it in my pocket without taking the time to examine them. I found feminine knee highs and ankle socks to be very sexy and would have loved to take several pairs, but had to hurry. I quickly grabbed a pair of white ankle socks decorated with black polka dots and put them in my pocket.

My hands shook as I opened the next drawer and realized I had found her lingerie drawer full of slips and bras and assorted wonderfulness. I lifted three rather ordinary slips to discover the mother lode. I found a white body suit made of very heavy lace that stretched in my hands. It looked very expensive because the lace was so heavy it was opaque. The exquisite body suit seemed much too fine for a college student and must have been a gift from her boyfriend. I shoved the body suit into my pants and raced to the car to hide my feminine finds.

I shoved them in the center console and returned to the living room of Laurens house breathless from the erotic excitement of my horny heist. I was just in time as Lauren arrived home. I raced to finish helping her load the trailer because of my eagerness rush home and model my illicit intimates in front of the mirror in a flesh flogging fashion show.

After we finished loading, I sped home and ran inside as quickly as possible. I stripped down and eagerly pulled the shiny black tights over my feet and up my legs to my waist. I pulled the white lace body suit on and put my arms through the straps. The body suit was firm and heavy, giving a girdle like feeling of support and control. I then put on the ankle socks, which were particularly thin, silky and feminine. I stood to admire myself in the full length mirror by the bed. Madonna was just becoming a superstar, and I loved that my outfit resembled her lace and spandex look of the moment, just like a trendy girl. My stomach tingled with the butterflies of taboo arousal. I moved to the bed and, lying on my back, stretched my legs toward the ceiling. The black tights looked like black liquid poured evenly over my legs. They felt even better as I rubbed my legs together and enjoyed the feeling of the smooth texture. I was about to explode. I grabbed a pair of scissors from my desk. I unsnapped the crotch of the body suit, pulled the tights down to my thighs, and cut a slit in the panel at the crotch of the tights. I quickly pulled the tights up and snapped the crotch of the body suit. Moving back to the bed, I grabbed some lotion and a towel. I jumped on the bed and pulled my now raging hard on through the hole in the crotch of the tights. I moved the crotch of the body suit to the left and pulled my cock and balls through the right side leg opening so that the crotch of the body suit was smooth against my pubic mound beside my cock.

Squeezing the lotion into my hand, I reached my hand around my cock and began a long term relationship with the tights and body suit. After smoothing the lotion on my cock slowly and smoothly at first, I was soon stroking my cock at a fevered pitch while I held my legs in the air, admiring how lusciously feminine the tights and the dainty socks looked on my legs and feet. I imagined how hot they looked when the girls from school wore them around campus. I fantasized about how hot Leslie must have looked when she wore the body suit and imagined her sexy body in it as she wore it for her boyfriend. Stroking myself toward orgasm, I thought of how hot and nasty I would be as Leslie wearing this outfit. How I would let my boyfriend unsnap the crotch, pull the tights down to my thighs and pull my tights encased legs over his shoulders as he entered me, filling me with his cock. An orgasm rocked through my body as I pointed my toes in the air like I imagined Leslie would as she came with her cute sock covered feet pointed over the head of her boyfriend as he thrust into her and pushed her over the edge. I quickly grabbed the towel beside me and spread it across my waist as my orgasm hit me hard and the contractions from deep inside me pushed the ropes of cum out of my cock and onto the towel. Breathing deeply, I moaned with the pleasure of each contraction, milking my cock until it was spent and beginning to soften.

As I settled back on the bed, I basked in the wonderful feeling of my newly acquired clothes. I knew that my addiction was back stronger than ever and my naughty ways were here to stay. As packed to go home for the summer that same day, I made sure to pack the body suit, tights, and ankle socks thinking of the pleasure that they would bring me, but unaware that they were just the start of my girly collection.

wifetoy
wifetoy
319 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
10 Comments
AnonymousAnonymousabout 1 year ago

Very sexy story, Wifetoy. Looking forward to reading the others.

Slaveslutpatty69Slaveslutpatty69about 2 years ago

I used to take panties, bras and other lingerie from family , friends, and others. I got caught several times, most of which were humiliatingly erotic and led to me being severely disciplined

AnonymousAnonymousalmost 6 years ago
Purrfect Threads

I simply luv💓 this crossdresser story thread....so very descriptive...and erotic!!! My tight VS thong is soaked with Crissy's sweetness.....Mmmm!!!

Thx for sharing, SissyCrissy

AnonymousAnonymousabout 8 years ago
Simply HOT !!!

This story is extremely erotic. I prefer my pretty thigh high stockings. But occasionally I'll squirm into a pair of my tight pantyhose. I have to make an incision in the cotton gusset. It makes for a marvelous "cock ring" keeping me so hard and "edging" for so long.......Mmmm !!! I need to get me a sexy body stocking to go with my tight thongs and other pretty, feminine lingerie.

SissyCrissy...................xoxoxo

Tootight1Tootight1over 9 years ago
understandable

5 stars, because, it's a similar story, to every CD/TV that I have ever heard of or talked to, they all can relate to it at some degree. the fact that your (loving wife) had you write it down, to tell the world, is not right. Those kind of woman don't deserve the air they breath, they have no original thoughts, they only use and abuse for their own ends. dump the wife ASAP, and continue with your fetish or what ever you care to call it, for the rest of your life, but stop steeling them, that's criminal. you'll find that you don't need her. your addiction, or fetish, is in your head, not hers. case in point, has she ever told you any of her, shall we say fetishes? remember, I said original thoughts, as in not one that someone else told her, including you.

Show More
Share this Story

Similar Stories

The Babysitter Babysitter guy becomes babysitter girl.in Transgender & Crossdressers
My Feminine Side Guy becomes a beautiful sexy girl.in Transgender & Crossdressers
Her Presents She had a number of surprises for him.in Fetish
Busted Wearing Panties Ch. 01 He's caught by his stepdaughter wearing her panties.in Transgender & Crossdressers
Feminized by My Girlfriend The start of how she changed my life.in Transgender & Crossdressers
More Stories