Rediscovery

Summer was winding down to a close. I had just finished my sophomore year of college and decided to take the fall semester off to work and save some money before I continued. I decided to work twelve hour shifts at the university lab to give me some free days during the week on which I could delve into my true desire: crossdressing.

Having just moved back into my parents' house, I had to be careful how I conducted myself and just how freely I was going to crossdress. I had a suitcase stuffed with a handful of lacy bras, colorful panties, risque lingerie and a number of dresses, skirts, and shirts. My wig and shoe departments were small, so the outfits that actually looked good were few. The suitcase was stuffed under the bed with junk piled up in front of it to block the view of anyone who looked underneath. It wasn't exactly the most secret spot, but I was usually given my privacy and it all worked out.

A few days into the new schedule, I hadn't found a single minute to dress up outside of the confines of my bedroom. I wondered if it would be worth trying to take everything into my car, get dressed in it and try going out in public for the first time as a woman. As I thought, my phone buzzed with a new text. It was from Clark, my childhood friend who lived a few doors down. I hadn't heard from him in a year or so and hoped that maybe he wanted to hang out and catch up. The text, however, simply said,

"Hey Jon would it be possible if you looked after our house next week? We'll be in California for 10 days and need someone to do the sprinklers and water the plants."

It sounded good. They usually paid well and it wasn't much work. Clark was the only kid left in the house; his oldest sister was long married and living out of state while the sister just older than him was at school an hour or two away. No one was close enough to do it, and I'd done it plenty of times before. After I replied and said yes, I realized instantly that I would have a whole house all to myself for an entire week! This was exactly what I needed to start this new schedule off the right way.

I waited impatiently for the day they left. The day before, I went over to their house so they could give me a key and go over what needed to be done. The controls for the sprinkler system were downstairs in the laundry room. As I walked down the stairs and thru the hallway that led to it, I passed the room of his older sister, Emma, the one a few years older who was down at school. Emma had been the one who's clothes I used as a kid to really develop my love for crossdressing. At sleepovers I would wake up in the middle of the night, sneak to the laundry room, and find a bra or pair of panties of hers that I could slip on and back off quickly before creeping back into Clark's room. It was a risky business back then, but I loved the way I felt every time I wore her clothes.

We finished up with my instructions and I went on my way home, content that the next few days could be spent wearing makeup and lace while I played with myself like the horny little college girl I was inside.

I waited for a day after they left to begin my adventures. I didn't want to go in on the first day ready to dress just to find that they blew a tire and had to turn around. The wait was killing me, but I knew it would be well worth it. While my mom worked out in the garden, I grabbed my suitcase from under my bed and quickly ran outside to my car to get it into the trunk without being seen and questioned about it. Once I decided no one had spotted me, I calmly got into the car and drove to that destination that so excited me. Their driveway was long and covered by trees, so I had no fears of being seen hauling in a suitcase to the house. Once inside, I set the suitcase down by the stairs and went about the chores I was being paid to do. If I was being paid to do the job, I would do it well, especially if I was going to be using their house as a base of feminine operations for the next few days.

Turning sprinklers on and off took an hour or so, and ten minutes after that the house plants were taken care of. I went into the living room, sunk down into the couch, and wondered about what I would wear and how good it would make me feel. As I thought about the clothes that rested just feet away from me, I began to feel myself get hard.

I got up and grabbed the handle of my suitcase and began to head downstairs. There were some big windows in the living room upstairs, and I didn't want to take the chance that someone would come to the door, peek in the window and see me. I went into Emma's bedroom. It was big enough to lay out all of my clothes so I could decide what to wear. I undid the lock that prevented anyone who did find the suitcase from opening it and unzipped the top. There they were. Bras and thongs, lace and satin, my silicone breast forms and foam hip pads. I almost licked my lips looking at it all.

I quickly took of my shirt and shorts and soon was standing stark naked in the room. In preparation for this week, I had shaved my entire body from the neck down. I wasn't too worried about someone noticing; I wore pants almost all the time and would just chalk it up to curiousity about the feeling if anyone noticed and asked me why I had shaved my legs. My body was feminine. I was only 5'9 and still pretty skinny. My arms weren't muscular and neither were my legs, though they had enough muscle and fat to look good, especially shaved. My pride and joy, as a crossdresser anyway, was my ass. Again it wasn't necessarily toned, but it was big and looked pretty good, especially when complimented by some underwear or some leggings.

As good as my butt looked, however, my hips were lacking any semblance of curve, hence the hip pads. I wanted to start out feeling sexy in just woman's clothes, so I decided to skip those for now. Naked and a little chilly, I looked at my suitcase of clothes and grabbed one of my favorite pairs of underwear. It was a lacy black thong with a matching bra and garter belt. I slipped my feet into the thong and shivered as I felt it graze my smooth skin as I pulled it snug against my hips and ass. Next came the bra. I clasped it in the front and turned it around, pulling the straps over my shoulders and letting them snap into place.

But now came the best part. I took the garter and fastened it around my waist. My heart was beating as I took a pair of 20 den thigh highs from my clothing pile. I sat down on the bed and raised my right leg as I slipped the sheer material over my legs. God damn did it feel good. I slipped on the left stocking, my cock almost fully erect, and stood up to fasten the suspenders to the stockings' lace. I swung my hips gratuitously as I walked over to a mirror sitting up against the wall. My legs looked perfect. I turned around and struck a pose, flexing my ass as I did. Anyone who saw that ass would have marveled. It looked good and I knew it. I began to imagine myself getting fucked in the ass with a strapon. I was fully erect and knew I would be taking care of myself soon.

But before I did, I wanted to dress up fully. I dug through the suitcase and took my brunette wig and put it on. It was an inexpensive wig but looked better than any I had found before. My breast forms were practically begging to be worn. I picked them up and slipped them into my bra cups to complete what would be my feminine figure. But what outfit to wear? I loved wearing dresses, but I didn't have many. A black pencil skirt would have to do, complimented by a white long sleeve. Wearing a white top with a black bra always turned me on. Had I gone out like that, I knew people would be able to see it, imagining what else is underneath. I put on my shirt and adjusted my boobs. They looked big, round, and real and it felt like I genuinely had a pair of D cup tits. I slipped my skirt on and zipped up the back in the mirror, admiring my feminine figure and thinking how hot I looked.

I was ready to masturbate now. I had been rock hard for several minutes and could feel the strain of my cock pushing against the soft material of my panties. Getting off while dressed was unlike any other feeling, and I couldn't wait. I had purchased 7 inch dildo from a sex store several months ago, but had only used it twice. This would be the first while dressed. I wanted my hole to be filled as my tits bounced up and down. I took it from the suitcase along with a bottle of lube. I felt like a little slut as I grabbed the shaft and stuck tip into my mouth. I licked all up and down and tried to deepthroat it as much as I could. It was wet, but I knew it needed some lube if I was to fuck myself with it. I opened the bottle and squirted out a generous amount onto my finger. I reached down and began to massage my hole with my lubed finger, slipping it in and circling around the edge. I put more on the dildo and knelt down on the bed. I hiked my skirt up to my waist and pulled my panties down as far as the garter belt would let me. I was ready.

Putting the large toy down on the bed and holding it in place, I lowered myself down slowly onto the tip. I gasped as it entered, and moaned loudly as it filled me up. I took my cock in my other hand and began to stroke myself as I raised my hips up and down on the massive fake cock. This was the best I had ever felt masturbating. I was so lost in how good I felt that I didn't hear the front door open and close. I was deep into my own lovemaking session when I opened my eyes and noticed a figure in the doorway to my left. It was Emma, and she was recording me on her phone. My heart jumped into my throat as I pulled the dildo from my wet hole and scrambled to pull up my panties and skirt. I sat on the bed and stammered, "I...I...". I knew there was nothing I could say. What would I? That I could explain? Explain how I fucked myself in her bed in woman's clothes? I was in deep shit.

"That was something else." said Emma as she finally broke the silence. "I didn't think I'd ever actually meet a guy who likes to take it in the ass like that."

I remained quiet. I still was at a complete loss for words.

"What do you have to say for yourself?" She asked with a smirk on her face.

"I...I'm so sorry. I thought I would be alone and no one would know." I replied, knowing that wasn't good enough.

"You are fucking disgusting, Jon. That's some pretty messed up shit."

"I know" I said, "I don't know what I was thinking. Please don't tell anyone though. I saw you recording. Please don't show that to anyone!"

Emma laughed. "Why? So you can still look like a good kid who doesn't have weird sexual fetishes?"

There was no way I would get out of this. She never liked me much and would gladly ruin me like this.

"Please," I begged, "I'll do anything if you just don't let this get out."

Emma still stood there, leaning up against the doorway with her hand on her hip.

"Anything?" she asked.

"Yes! I will do anything if you just promise you won't tell anyone what I did!"

Emma straightened herself up and walked over the bed. She came right up to me and leaned down right into my face and said, "You will be my little bitch this weekend, do anything I tell you to, and I won't tell a soul. Agreed?" I had no other option.

"Ye...yes..." I managed to get out.

"I planned to go back up tomorrow morning, but I guess my weekend plans will have to change, starting right now."

I wondered what she meant. She didn't give me much time to think. She grabbed the dildo I had been fucking myself with and laid back in the bed.

"Get on your hands and knees." She said.

I obliged. She put the dildo on her crotch and held it there.

"Blow me." She commanded.

"What?"

"Blow me. Now. Or your ass is grass."

Apart from lubing up the dildo with my mouth a few times, I had no idea what I was doing. I had had blowjobs before, but now I was supposed to be giving one, even if it was to a fake cock. I brushed my hair to one side and grabbed the base of the shaft next to her hand. I bent down and looked up at Emma's eyes as I kissed the tip of her cock. I used my tongue as much as I could, licking the top and working my way slowly down and around the shaft. I went back up to the tip and put it in my mouth when I suddenly felt Emma's hand on the back of my head. I had no time to react when she shoved my head as far down as it would go. The dildo was all the way back in my throat. I began to choke but remembered to breathe thru my nose. She took her other hand and put it on my head and began to guide me as I blew her. As I did my best, I thought to myself,

"Wow, I'm actually enjoying this."

I was getting more and more into it as I felt myself begin to harden again. Being caught had completely killed my erection, but giving a blowjob to a beautiful woman while fully dressed was more than enough to make me rock hard again.

After a while, she pulled out of my mouth.

"You're pretty good. Have a lot of experience, eh?" She said.

"No," I replied, "I just know how I would want it."

She sat up in the bed, looking at me with her deep blue eyes. Shifting her weight forward she said softly,

"Show me what else you would want."

To be continued