tagTranssexuals & CrossdressersCollege Crossdressing Confessions Ch. 02

College Crossdressing Confessions Ch. 02


My wife's control over me insures that I have no secrets from her no matter how depraved my hidden desires. As part of my training, she has ordered me to confess my prior deviant acts to the world. This is the second part of a series in which I obey her command that 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.

Once I was home from SMU and working my summer job, the black tights and heavenly body suit that I pilfered from Lauren and her roommate kept me satisfied for a few weeks of regular dress up sessions before I needed some variety for my feminine fix.

My friend Evan was also home from school for the summer. Evan's father was a very successful physician, and his parents spent most weekends at their vacation home, leaving their beautiful home to us as our private party house. We got away with this because we did not abuse it and kept the crowd to about 8 or 10, mostly couples (no more than one for each bedroom).

Evan had three older sisters, two out of college and married and one, Carla, who had just graduated from USC and was spending her summer working on Capital Hill. Carla was the prototypical spoiled American princess. She was also smoking hot. She was about 5'6"with tan Mediterranean skin and a tight body, small high breasts, and a great ass that perfectly filled her small bikini bottom when she tanned by their pool. She was very much the bitchy, prissy older sister. She was also well aware of her gifts and delighted in teasing her brother's friends. Carla was a fixture in my jack off fantasies.

We were spending another weekend hanging out at Evan's house. After a blow out Friday night, I was spending Saturday night sitting around watching movies with Evan, his girlfriend, and a couple of other friends. The other friends left to go home early to sleep off the previous night. Evan's girlfriend had her head on his lap, and he soon got up saying they were going to turn in early, I assume after a spirited fuck session. Evan suggested I just crash at his house since my parents were away. "You can just sleep in Carla's room." I accepted the invitation, trying not to look too excited. In the past, Carla's room had been off limits because she was usually home from school when we were.

Carla's room was at the other end of the house from Evan's room, which was off of the rec room his parents had added to the back of the house. Telling them good night, I walked down the hall and into Carla's room. I carefully locked the door behind me, and began to explore my opportunities.

Since I had the door safely locked, I tried to take my time, but my heart raced as I opened her panty drawer. I trembled as I fondled her tiny string bikini panties. I hurriedly removed my clothes and tried on several pairs of panties. I felt so good and girly as I posed in front of the mirror in her panties. Pretty pink, naughty black lace, and pure white satin string bikinis all looked and felt so great covering my maleness in Carla's femininity. I selected a white satin pair that covered my cock and balls in silky pleasure for later use.

I moved to the second drawer. It was more than half empty, but was the drawer where Carla kept her workout clothes. She had obviously packed several workout outfits to wear in Washington. I felt that familiar feeing in the pit of my stomach as I pulled out a pair of white Danskin shimmer stirrup tights and a blouson top leotard. I had found my first outfit. I pulled the tights on stretching up my waist, and fixed the stirrups so they were straight over my feet. The tights were small for me, but stretched enough for me to wear them when I pulled them high up my waist. The smallness actually made them hug my balls and cock even tighter with delightful shiny lycra. I pulled on the leotard, which was light pastel purple with a loose cotton top, which was perfect for fitting my broader upper body, and a tight stretchy panty with high cut legs. It was very similar to the leotard that Olivia Newton John wore in one of her videos. I pulled the leotard up my body and put my arms through the armholes. It barely fit, but felt great, tightly squeezing my cock and balls so they flattened into a mound.

Lying down on the bed, I stretched my legs up and admired how feminine they looked in the white opaque shimmer tights. I felt like a feminine modern dancer with my bare toes pointing through the stirrups. Taking my time, I rubbed my hands up my shiny white legs soaking in the warm sensations and imagining how sexy Carla looked working out in this outfit. Knowing that these were her leotard and tights and thinking about her smoking hot ass and beautiful body filling them out as she stretched and strained her way through a workout made wearing them even naughtier. I also found a pair of big, slouchy aerobics socks in the drawer and pulled those over my feet enjoying the sensation the socks sliding over the satiny tights. I felt like an 80's aerobics queen. I moved her mirror so I could see myself on the bed. I stretched and posed in the mirror.

It felt so sexy being in Carla's leotard and tights, like I was sharing a part of her femininity. I had to come. I reached down to the leotard panty and pulled the tights down on one side and pulled my cock out from it spandex nesting place. I reached up to her bedside table and opened the drawer to investigate my lotion options. I grabbed some lotion out of the drawer and filled my hand with lotion before spreading it on my now hard cock. As I stroked myself, I lifted my legs up and again imagined Carla's legs as she worked hard in her aerobics classes. It did not take me long before I came, spurting into my cupped hand.

I cleaned myself up and pulled up the tights and leotard and sat on the bed reading her woman's magazines until my interest in some more searching in her drawer grew again. Looking at the great clothes and smelling the perfume samples in the magazines soon reawakened my feminine longings. I got up, still enjoying the leotard and tights cupping my reviving cock, and pulled open her bottom drawer. This was her sock drawer. At first I found the usual cotton ankle socks and preppy knee socks since Carla was definitely a preppy little cock tease. Then, much to my surprise, I found a pair of what appeared to be silky white ribbed thigh high stockings. While common today, these were very rare in the late 1980's and not something a "nice sorority girl" like Carla would normally wear. Carla had apparently developed a bit of a naughty side at college, and I was eager to share in her naughtiness.

I hurriedly pulled off the leotard and tights. Sitting on Carla's bed, I pulled the deliciously soft thigh high stockings up my leg stretching each of them as far up my thigh as they would go. I reached up on the wall and pulled a framed mirror off the wall and leaned it against the head board of Carla's bed so I could watch myself from another angle. I leaned back on the bed, stretched my legs high in the air, and pointed my toes to show off my girly legs. The white thigh high's looked very feminine contrasted with my tanned legs. They were opaque, but had a shiny hue. I imagined how sexy they would look on Carla's darkly tanned legs. I continued to pose in the mirror, incredibly turned on by the white stockings.

I reached into Carla's bedside table drawer and noticed a large fat novelty writing pen with her Delta Delta Delta sorority letters printed down its length sitting in the drawer. Ever the anal slut, I spread some lotion on the pen and pressed the end of it against my puckered asshole. My sphincter gave way and I eased the pen into my ass enjoying the full feeling of penetration. I pumped the lotion into my other hand and began stroking my cock. At the same time, I started to push the pen in and out of my asshole, gently fucking myself while I admired the view like my own porno movie in the mirror. Picking up my pace on my cock and my ass, I imagined Carla being fucked by her boyfriend wearing these same stockings. I pulled my legs over my head and imagined that his dick was fucking me just as he fucked her while she placed her legs over his shoulder- the soft white innocence of the cute ribbed stockings beautifully corrupted by her primitive lust as she pulled her ass toward him to meet each thrust of his cock.

With my two pronged efforts, fucking my ass with the Tri-Delt pen and stroking my cock, it did not take long before my orgasm began to rise deep within my bowels. I pushed the fat pen deeper into my ass. I enjoyed a naughty laugh in the midst of my pleasure as the last Delta disappeared into my asshole and only the tip remained visible, tightly gripped by my fingers. With the pen stretching my asshole and pushing against my prostate, my entire lower body was enveloped in waves of pleasure as my sphincter began to contracting around the hard plastic of the pen in quickening spasms. I straightened out my legs to maximize the rushing orgasm as it overcame me. My cock began shooting thick ropes of come onto my stomach and chest as I continued to fuck myself with the pen driving the intense anal pleasure through the end of my orgasm.

As my cock gradually softened in my hand, I slipped the pen from my ass, carefully removed the thigh high's, cleaned up my mess. I put the leotard and tights carefully back in Carla's drawer, but slipped the thigh highs into my bag along with the pair of cute panties I had collected earlier to add to my collection.

I showered, pulled on pair of Carla's pink bikini panties, and climbed into Carla's bed, enjoying the warm contentment of our feminine connection under her soft girly sheets.

Several weeks later, after I had milked my existing girly tights, panties and stockings to their limits, I had an urge for new stuff. Still stuck in my parents' house for two weeks before school started, I had to be creative. I have always had a fetish for garter belts and stockings, but had not come across anything remotely close in my search through the drawers of my fellow coeds or friends' sisters. I hatched a plan. I went to our local department store to see what I could find.

I arrived at the store shortly after it opened. Thankfully it was not crowded. I headed to the lingerie department. I made up a story that I was trying a joke gift for my sister's wedding and asked whether they had a garter belt or something I could give her for a laugh just between us (looking back on it, that may be creepier than my cross dressing fetish)

The cute sales girl was about 25. She smirked when I told her my story about a gift for my sister. "I can help you find something, um, for your sister" she giggled. You would not believe how many men come in here looking for pretty girly things for their sisters or girlfriends. What color would you like, I mean do you think your sister would like?"

"I think she would like black, anyway it is just a joke gift," I responded, failing to conceal my nervousness.

She smiled and nodded her head "Sure, I understand." She went over to the corner the department and pulled a black satin garter belt out from the rack. "This one is on sale and comes with black stockings and cute matching panties, if you want to wear panties with it, I mean if you think your sister would," she said with a knowing smile. Sensing my fear, she played with me. "Do you think your sister would like these cute matching panties," she teased holding up the black satin string bikini panties.

"Yes, I think she would," I managed to say while trying to maintain my composure.

She rang up the sale, smiling mischievously the entire time, and handed me the package, saying "my name is Heather. If you need any other sexy lingerie for your sister, come back and see me. I will be glad to help you pick something out."

I raced home, turned on beyond belief by imagining what the sales girl was thinking and what she would tell her friends about the college boy who bought the garter belt, stockings, and panties. From her smile, it was clear that she knew the truth. I knew that that possibility would fuel numerous fantasies in the future.

My parents were out of town, so, when I arrived home, I immediately stripped off my clothes. I hurriedly stretched the garter belt around my waist and fastened the hook and eye closures. I tore open the package containing the stockings and rolled them slowly up my legs, clipping them to the metal garters, and then pulled the panties up over the garters. I stood up and paraded in front of the mirror, enjoying the girly results of my successful mission. I grabbed some baby oil off of the counter and pulled my cock and balls through the leg of the panties. Leaning on the bed in front of my sister's full length mirror, I squirted the baby oil into my cupped hand and began furiously pumping my cock. I stretched out my legs to tighten my ass around my prostate and admired myself in the mirror, thinking about Heather, the cute the sales girl, forcing me to try on naughty lingerie as she laughed at my sissy need to be girly. Triggered by this fantasy, I came violently trying in vain to collect the squirts of cum in my hand.

I cleaned up and folded my new lingerie away with my collection, so I could take it to school when I left the following week. I felt a little guilty about my fetish, especially taking things from girls, but knew that I could never stop.

Report Story

bywifetoy© 7 comments/ 50593 views/ 10 favorites

Share the love

Tags For This Story

Report a Bug

1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartAkhiljha, wand010 and 8 other people favorited this story! 

by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by cdCindy108/14/17

I buy clothes too

I love buying clothes when the salesgirl knows the items are for me. I give subtle hints (like saying my girlfriend is the same size as me) and then if they catch on then I admit to them that the clothesmore...

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

Show more comments or
Read All 7 User Comments  or
Click here to leave your own comment on this submission!

Add a

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

Refresh ImageYou may also listen to a recording of the characters.

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: