Karlie's College Adventures

I don't suppose my story is really any different when it comes to cross-dressing. It began when I was young and continued to flourish as I grew older. I lived alone with my mother growing up. My father had been killed in car wreck when I was 8. He had been a successful stockbroker and had left my mother and I financially stable, if not wealthy. My mother was also a broker and continued to work after my father passed away. She had never remarried. Her work and raising me were her only focus. She dated, but never seriously. Instead we traveled a lot growing up, as my school and her work schedule allowed.

My mother had been raised to think that a woman should always look her best. Her wardrobe was always bursting with the most fashionable clothes and shoes. As I grew up, I constantly heard my mother receive compliments for her style. It always made me feel proud to know that I had such a beautiful mother. I loved to see the new outfits she had selected and I often wondered what it felt like to wear those beautiful clothes.

She worked long hours and after I reached a certain age, she allowed me to stay home in the evenings by myself. Naturally, my curiosity about her clothes eventually led me to her closet. I would touch the soft fabrics of her blouses, skirts and dresses. The silky things I found in her lingerie drawers held my interest as well. She had a wonderful collection of sexy panties, bras, and hosiery. Naturally, it was just a matter of time before I began to try them on. I would go in her room nearly every day when I got home from school to try her sexy clothes on. I lived for the moments when I could slip in some of her silky underthings and put on a pair of her sexy high heels.

I had always been pretty small for a guy. By the time I finished high school, I was a whopping 5'2" and weighed about 120 pounds. By contrast, my mother was about two inches taller than me even without her heels. This turned out to be a great thing since she and I were virtually the same size. I was able to wear all of her clothes as well as her vast high heel and boot collection.

Being the fashion conscious woman she was, Mom frequently would set out older clothes and shoes for donation to local charities. I soon learned to divert those boxes to my room for inspection before they went to the donation box. A blouse here, a skirt there and I soon had a fairly respectable collection all of my own. I had a door in my closet that lead directly into the attic of our house where I could keep my treasures.

After I had my own transportation, I began going to the local mall and buying my own things. The thrill of doing it the first time was something I'll never forget. I had walked into a lingerie store and began looking through the panties. A cute young sales girl had walked up and asked if I needed help. At first I was embarrassed, but she did her best to put me at ease. Naturally, I used the time tested "buying something for my girlfriend" excuse. She smiled and winked. I was certain she knew what I was doing! After 20 minutes of shopping, I had my hands full with 5 matching bras and panties. I had also purchased a lacy black garter belt. She even helped me select some stockings to go with it.

Last summer I graduated from high school. My Mom had been offered a temporary position with her brokerage in Japan for the summer. We had debated whether I would go with her or not. I had already secured a summer job I was looking forward to, but the opportunity to live somewhere different for an entire summer was appealing. Ultimately, I decided that I would stay home and work my summer job. Mom was disappointed, but she said that it would be a great opportunity to practice living on my own before I left for college. I agreed.

I also knew it would be a wonderful opportunity for spending extended time as Karlie, which was what I had begun to refer to myself as when dressed.

The week Mom left was a mix of emotions. I was sad that she would be gone for two months, but the thought of having the house all to myself filled me with excitement. After I dropped her off at the airport, I quickly sped back home to enjoy my time alone.

I spent every night that summer dressed fully as Karlie. I began to experiment with Mom's make-up. I had always had somewhat feminine features and very little facial hair. A close shave and a little makeup really helped. After much trial and error, along with repeated how-to videos from You Tube, I got to the point I could get made up and not look like a total hooker. Each night I would pick out an outfit and dress. I would spend time walking in front of the large mirror my mother had in her bedroom. I wanted to make sure I moved like a sexy young lady and not a clumsy 18 year old boy.

I also began to search out other crossdressers online. I met many nice gurls from across the country, and even around the world. Those chat sessions helped me realize that I was not alone. I also picked up a lot of valuable tips for being a gurl. I enjoyed the thrill of exchanging photos with them and the many compliments I received.

One night in mid-June, I was dressed in a short black skirt and chemise with silky tan pantyhose. I was looking through my mother's huge closet for a favorite pair of heels of mine. After finally realizing she must have taken them with her, I turned in frustration to walk out. I spotted a cardboard box in the corner I hadn't noticed before. Mom had been rearranging things in her closet and had moved a few things to the attic the week before she left for Japan. I remembered that she had declined my help, which had seemed odd to me at the time.

Out of curiosity, I reached down to pick the box up. It was actually quite heavy. Without hesitation, I pulled the flaps open and was more than a little surprised to see what was inside. The box contained dildos and sex toys of all shapes and sizes. I had seen my mother's vibrator in her bedside table before, so the toys were not that shocking. However, the numerous porn DVDs as well as a large number of unmarked DVDs in a separated binder were. It definitely got me curious. I grabbed the whole box and walked out in to my mother's bedroom. I removed the DVD binder and began to flip through them. I couldn't find labels on any of them, so I just picked one and placed it the DVD player. I grabbed the remote and walked to sit on her bed.

When the DVD started, I watched on the large screen plasma TV my Mom and Dad's honeymoon trip to France. Mom looked so young and beautiful. Dad was really handsome as well. The video continued for approximately 30 minutes showing them as they went to the Eiffel Tower, the Louvre, and many other places in Paris. It made me feel sad to see Mom and Dad look so happy since he was now gone. He was constantly making jokes as they walked around. It was funny to hear my Mom laugh. I hadn't heard her laugh like that in a long time.

There was a break in the video. I picked up the remote and fast forwarded through the black areas. When the video restarted, the camera was obviously on a tri-pod in a luxurious hotel room. I felt a touch of embarrassment. The camera was pointed at the bed!

I saw Dad walk from behind the camera. He was naked. Feeling ashamed, I reached for the remote to stop the video, but I heard him talking softly to Mom. She slowly appeared from the left side of the screen. She was dressed in sexy black lingerie complete with stockings and heels. She looked unbelievable. Her thin shape was accentuated by her firm breasts and ass. Wow, I thought to myself. She was really something!

After a little urging from Dad, she stopped in front of the camera and did a little twirl. I marveled at how sexy she looked. I also noticed that my father was pretty impressive as well. He was in great shape with a nice chest and flat abs. I hadn't got my slender body shape from him, for sure. He turned a little towards the camera. I was amazed by his penis. It was huge! Even limp he was much bigger than me.

I watched the video further as he took her into his arms and they began to slowly kiss and caress one another. His hands roamed all over her sexy body. I was a little ashamed that I kept watching, but I just couldn't make myself turn it off.

I watched with my mouth agape as my mother kissed her way down his chest and abdomen until she was kneeling in front of him. Her small little hand grasped his hardening cock before she slowly took it in her mouth. My mouth suddenly felt dry as I watched her begin to suck him. I could feel my own little cock getting hard in my pantyhose.

I was shaken from the erotic sight by my iPhone vibrating inside my bra. I reached to get it and saw that it was Mom calling. I quickly grabbed the remote to mute the volume before answering.

"Hi, Mom!"

"Hi Honey, how are you," she asked.

"I'm fine, How about you?"

"Great, just busy! I was leaving to catch the train to the office and I thought I'd call and see how you were." I could sense a little exasperation in her voice.

"Oh, okay. I'm fine."

We talked for a couple more minutes. I realized I was distracted by the images on the TV and my part of the conversation consisted mostly of yeah and okay.

"Honey, what's wrong," Mom asked.

"Nothing, why?"

"You just seem preoccupied."

"Sorry. I'm just watching TV," I lied.

"Oh, what are you watching?"

"It's just an old movie."

"What's it about?"

"It's a love story set in Paris. I don't know the name of it." I smiled to myself for my little joke.

"Okay. I see."

We talked for a little while longer. The whole time I was watching her suck my late father's big hard cock. I wondered what it would be like to be knelt in front of a handsome man like him, doing that. Finally, she said she had to go and she would call me the next day. I felt a bit guilty, but the visions I was seeing on the TV were too exciting! I said goodbye and returned my full attention to the sexy display.

I had scooted back on the bed and was resting against the headboard on Mom's big soft pillows. I was so turned on watching the two of them. Dad had focused the camera in to get a close up of mom at work. My God, he had to be over 7" and was extremely thick.

I looked through the box of toys and I found a very realistic looking fake cock. It looked to be about the same size as dad. I felt it in my hands and imagined what it would feel like if it was real. I watched Mom continue to slide her mouth up and down that huge thing. She was trying to get as much down her throat as she could. She wasn't able to get all of it, but she was certainly doing her best.

I kept playing with the fake cock and I decided I wanted to see how it felt. I brought it to my face and opened my mouth. I felt like I almost had to unhinge my jaw to get it inside! I slowly slid it in my mouth. I didn't really like the plastic taste but God it made me feel dirty to be sucking on it. I slowly worked about half of it in my throat before I felt I was gagging. I wasn't nearly as good as Mom!!

I kept practicing as I watched Dad reach down to pull Mom to her feet. They kissed passionately before he led her to the bed. He gently nudged her until she was kneeling on the edge. When she was in place, he knelt behind her and slowly pulled her silky black panties down over her garter belt to her knees. His face was quickly planted on her sex.

I watched with keen interest as he slowly licked her up and down. She was moaning and talking as he did so. It was obvious he was licking her pussy, but I could see that he was also licking her ass. It made me wonder if mom enjoyed anal sex as well. I had experimented with my finger a few times. Now that I knew about this collection of toys, I knew I would have to try more!

I was still sucking that fake cock as I watched Dad stand up and slowly slide his hard cock into her from behind. She moaned softly as he entered her. My hand had found its way under my skirt and I was lightly touching my little clitty through my pantyhose. It was so hard.

On the TV, Dad began to slowly fuck Mom with his big cock. She moaned and purred. I watched as she reached one of her hands down between her legs. I assumed she was touching herself. Dad kept telling her how sexy she was and how much he loved her.

It was such a sexy sight watching them. They were so young and in love. Mom was absolutely breathtaking, while Dad looked like he had been chiseled from stone. I turned to look at Mom's beside table where she still had a picture of him. He had been really handsome.

I noticed additional movement on the TV screen and I turned back. They had changed positions. Mom was now on her back and Dad was between her spread thighs. Her sexy, stocking covered legs were sliding up and down his ass and legs. I turned up the volume so I could hear their passionate moans clearer. Mom was telling him how good it felt to have him inside her.

Dad gradually increased his pace. My own hand was down inside my pantyhose and I was stroking my little clitty quickly. I knew I was about to make a mess of pantyhose.

Dad told Mom that he was getting close. She just groaned and wrapped her arms around his neck. Dad was really slamming into her. I felt myself getting ready to cum as well. After just a few more strokes, I shot my gurly cum into my pantyhose.

I heard Dad groan and I watched as his strokes got shorter and much more intense. He was filling her up with his cum!! Mom moaned and told him how good it was.

I laid there recovering as I watched Mom and Dad kiss. They looked so beautiful together. I looked down and saw I had made quite a mess. My hose were soaked. I pulled my hand out and began to lick my cum from it. I had only recently started doing that and it was quite a thrill.

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I spent the rest of the summer watching their sexy videos together. Apparently, they had quite the active lifestyle before I was born. I had no idea that they had been so wild. Most of the videos had been filmed at their big apartment in the city. We had lived there until I was 5, when we moved out to our house in the suburbs. I watched them do everything imaginable. I saw Dad make love to other women and Mom with other men. I saw Mom have sex with other women and I even watched my Dad get a blowjob from another man. I thought to myself how lucky that man had been. Dad's cock had looked amazing.

I often imagined myself being Mom when I watched the videos. Watching her fucking and sucking turned me on like nothing I had ever experienced. She always seemed to be dressed in sexy lingerie. I experimented heavily with the fake cocks. I began trying to fuck myself with them. It was difficult at first, and I learned that it took a lot of preparation. I was soon taking the 6" dildo easily. I never was able to get the big one in though. I always seem to get too aroused and lose control before I did. I was amazed that she had been able to take Dad in her ass so easily.

Between work and my nightly play time, the summer passed quickly. I was getting more excited about going to college and being able to continue my private life as Karlie.

Mom came home in time for us to take a quick trip to Paris before I left for school. We spent a lot of time going to museums and seeing the sights. She also spent a lot of time shopping. I acted disinterested, but I was actually envious as she tried on so many sexy outfits. I knew they were my size and I really wanted to try them on as well. I knew that whatever she bought, eventually I would get to!

We came home and it was soon time for me to pack for college. I was a little sad to be leaving home but I knew that it was a necessary step I had to make in life. Mom was really busy with work, so she couldn't accompany me on my trip to my new school. She had promised she would be up the following weekend to make sure I was settled in.

I loaded up my car and I left. It was an 8 hour drive to my new school. I was fortunate in that the university I had chosen was having a housing shortage, and I would not be able to live in the dorms. I would have to suffer the fate of having my own private off-campus apartment! When I arrived I quickly secured my key and began moving into my new home.

Having the summer alone had definitely prepared me for the new freedom I now had. After classes started, I would go home at the end of the day and put on something girly and do my homework. I made a few friends quickly and enjoyed spending time with them, but I really cherished the time I could have as Karlie.

Having my own place and a credit card I was solely responsible for allowed me to purchase things on-line without mom's approval. I acquired breast forms as well as additional clothes and lingerie. Mom had allowed me a generous monthly allowance for food and fun. I'll admit I skimped by on Ramen noodles more than once to get a sexy pair of heels or new panties.

I continued to spend a lot of time chatting with other crossdressers online. These times would often lead to some webcam fun. I loved hearing their stories of the times when they had met men. I also began to chat regularly with men online. It was quite a turn-on to have them tell me how sexy I was. I loved watching them stroke their hard dicks on webcam.

As the semester passed by, I realized I was getting more and more curious about being with a guy in person. I wanted to know how it felt to be a girl and to pleasure a man in real life. However, I was scared to death about actually doing it. I spent a lot of time looking on the local personals sites. I loved reading the descriptions of what the men were looking for and looking at the pictures of hard, tasty looking dicks that were often posted. Many times I thought about replying to an ad, but I would always back out. Being 5'2" and 120 pounds gave me few allusions of being able to defend myself from some psycho.

In October, I was chatting with Roxanne, a local cd friend. I had met her online during the previous summer. It was coincidental that she lived in the same city where I was going to attend college. After I got to school, we actually met in person. She was in her late 30's and was married. She had been to my apartment a few times and we had dressed and hung out.

I was telling her that night that I really wanted to meet a man, but I was scared. She was giving me advice on what to look for. She said she had met many nice men over the years and that I would too, I just needed to be careful and patient.

Later that night, she sent me a link to a personal ad. I opened it and saw it was a man in his early 50's that lived locally. He was seeking a cute young cross-dresser for regular discrete companionship. He had included a picture. He was a very handsome man.

"He looks nice." I typed back.

"Yes, he does. Maybe you could respond," she replied.

"Should I?"

"What would it hurt? You could get to know him at least." She responded.

We chatted for a bit longer. I kept thinking maybe I should respond to the ad. She was right. What would it hurt? If he seemed creepy, I could always not reply back. I finally told Roxanne I was going to reply.

"Good, sweetie. Just be open with him about everything. If he wants to try and rush you, back off. Okay?"

"Okay."

I hit reply to the ad and began my message.

"Hi! I'm Karlie. I'm a 19 yo crossdresser. I'd like to get to know you better. I'm very new to this. I hope you don't mind going slowly. I look forward to hearing from you again."

Within 5 minutes, my phone beeped. I looked and saw that it was from an unfamiliar address. I felt a tingle as I opened the message.

"Hi Karlie! I'm Richard. It's nice to meet you! I certainly want to get to know you better as well. I'm not looking for something immediately. I want to find someone that shares a mutual attraction and that is discrete and safe. I'm a widower and have never done anything like this. I have attached a couple photos (nothing too racy!!). If you are comfortable, please send me a pic back. I'm sure you're beautiful."