Caught Cross-Dressed & Dominatedbybondage_philosopher©
The day had been pretty boring at college. I couldn't wait till I got home. I knew today would be the day. Both parents would be gone, and I just received my package in the mail. As if it weren't great enough, tonight was the first night of spring break. My parents wouldn't be gone for only one night, but they were taking a vacation and leaving me home alone to house sit. Being the mature twenty-one year old I am, they trusted me.
I wouldn't have any parties. I had something else planned. Since my siblings were away at college and weren't coming back for spring break, I would soon have the whole house to myself. The whole place to myself for a week! I had many thoughts going through my mind about what I was going to do. It would be the best spring break in a long while.
I looked at the clock. There were only fifteen minutes until the end of the class. I told my friends I might be busy during break so I didn't expect any of them to stop by either. In fact, I prepared my situation quite well. No parents, friends, or relatives to barge in on my endeavors.
There was only one other possibility, but I didn't think she'd find out. She hadn't talked to me for a long time, and we went to different schools too. Although we used to be good friends, things weren't the same anymore. I don't even know why I had included her as a variable into the equation of people who might stop by my house. I didn't want to think about being discovered anymore. I just wanted that damn bell to ring so I could go home and enjoy my weekend.
There wasn't anything to do, and the students had finished taking their exams. I slumped my head over my arm and looked out the window. Trees, blue sky, and clouds enveloped me. No large buildings blocked my view of the clouds. There were no noisy traffic streets. It was just a typical quiet day in my quaint, modest city.
"What are you doing this spring break?" I overheard Joe ask Ashley.
"My friends and I are going to the beach. Want to come?" she replied.
"Maybe. I'll see what the rest of the guys are doing. It sounds fun, and I bet they'll want to go."
"Hey, James," Joe said leaning over to me. "How about it? Want to check out the waves and the girls?"
"I can't, dude," I said trying to evade him. I didn't want to answer why.
Just before he mouthed why, the bell rang and I jumped out the door. Quickly, I slid past my fellow students towards the back of the building, where an old exit remained unused. It would save me the trouble of escaping more questions and invitations. Usually, I would open the invitations with open arms. I'm not spoiled or mad at being included, I just had other plans. Besides, a spring break alone? I wouldn't have this opportunity again. I found my car and hopped in, locked the doors, and started the engine. I made it. I left the parking lot and drove home.
I felt the freedom engulf me as my stereo played. I attempted to sing along, but unfortunately, I can't sing. I decided to celebrate my freedom by grabbing drunch on the way home. (Drunch is slang for the meal between lunch and dinner) I ate well and watched TV.
I was going to wait until it was dark in the evening before starting the process. But, I couldn't wait any longer. I wanted the longest time I could to enjoy myself. I made sure the answer machine was on and all the doors were locked. Finally, the time was here.
I gathered my restroom materials and started a hot bath. Stripped, I sank into the tub. The feeling of warm water all over my body was an enormous pleasure. I soaked for a few minutes before beginning. I wanted to savor every part of the experience. I applied the cream to my left leg. Here goes nothing, I thought to myself. I took a stroke, then two. I repeated the process until both legs were shaved. To make it as smooth as possible, I shaved both legs once more in case I missed any spots. I didn't bother washing the rest of my body because that would be next. I dried myself off and went to the shower. I turned it on and washed myself off making sure I washed away any lingering leg hairs. I washed the rest of my body until I was squeaky clean.
Next, I headed back towards my room. I closed the door out and opened my closet. I moved the hanging clothes aside and looked for the hallow space in the back. I found it and opened the door revealing my treasures. I selected what I wanted to wear tonight and placed the garments on my bed. Then, I rubbed lotion over my legs to keep them moisturized and delay the hair growth. If I was lucky, I might not have to shave again this break. Still, shaving was relaxing and set my mind at ease. I selected my white, silk panties to slip on first. The silky, wet feeling of the smooth fabric created a tightening my loins. I could have released right there. It would ruin the rest of the night, and I told myself I was going to wait until bedtime before I took care of it. Following the panties, I slid on a pair of tan pantyhose. The cool, downy fabric massaged my smooth skin and sent electric signals through out my body and back to my loins. I couldn't get over the feeling of silky pantyhose gliding across my smooth legs. I chose a lacey, under wire bra to wear. I slid on the straps and hooked the back with skilled expertise. I found my box, which contained my breasts, and carefully lifted them out. I took great care of my breast forms because $200 is a lot of money. Anyway, I slid my breasts into the cups and adjusted them to my satisfaction. I don't know why, but I loved the feel of the jiggling entities being pressed against my body by a tight bra. Now, came the actual clothing. I had ordered it offline even though I could probably have found the same type of outfit at a local thrift shop. Fortunately, I had the money and it was on sale anyway so I decided to go for it. It was a brand new green and black plaid skirt, size 6, with a small blouse to go along with it. The uniform also came with a pair of Mary Jane look-a-like shoes and white knee high socks.
After I put on my uniform, I strolled around the house until going to my sister's room. She had a huge mirror with tons of make up. Through years of experimenting and trial by errors, I had discovered the perfect combination for myself. I hardly used any of her important make up and the affect was quite pleasing. I went back to my room and applied the last few things. I had also just ordered a wig online as well. I had never worn a wig before, but I was curious about the feeling of having long hair. Since I always kept my hair short, a wig seemed to be the obvious solution. The hair was a light brown/dirty blondish color and measured several inches past my shoulders. I went to my mirror and adjusted it and tied little pigtails on it to enhance the whole schoolgirl look.
The whole process had taken well over three hours. I didn't mind the long process, however. The process was part of the fun. My parents had a full-length mirror in their bathroom so I trekked my way to their room. What I saw staring back at me was a shock. The total affect of the uniform, make up, and wig almost made me gasp. I actually looked like a six-teen or seven-teen year old girl. I always had a smaller frame than most guys and my facial characteristics were less pronounced, but I never imagined I would be able to pass so easily for a young lady. I don't mean to sound egotistical, but if I hadn't known it was me under everything, I would be checking me out.
For the next hour, I lounged around the house and watched TV enjoying the feelings of being fully dressed. I was trying to decide when to begin the next part of my evening. I froze several keys attached to strings the night before. I decided to check my other materials. As I went to my room, I felt my skirt brush against my pantyhosed legs, making my cock spring to life. The ecstasy was incredible. I began to worry about how long I could hold out before I needed to release. If I started the next phase of the evening, I wouldn't be able to do anything about my hard cock.
Instead of going to my room, I headed towards the freezer and retrieved one of the ice cubes. I grabbed a cup and hurried to my room. I opened my drawer and removed several layers of clothing before finding my stash. Over the years, I had collected three pairs of handcuffs, two pairs of leg irons, five chains, and numerous locks. I would have preferred the snug feel of rope against my skin, but I had no partner and it's very hard trying to bind oneself with rope. Cuffs were easier to use and held no chance for escape, which stirred strange desires within me. I felt my stomach drop as I positioned myself on the floor. I placed the cup on my desk with the string dangling down in easy reach. I figured I would have about half an hour to forty-five minutes before I could escape. I cuffed my legs together with a pair of leg irons. Next, I cuffed my hands behind my back, my stomach churning once again as I felt the last click and realized my helplessness. Finally, I looped the chain around the handcuff and leg iron chain and locked the chain in place, creating a nice, taut hogtie.
I relished in my helplessness. I indulged myself in my fantasy of being a poor little schoolgirl kidnapped by girl bullies. I would wait in my chains until they returned to do whatever they had planned. I was a damsel in distress being held captive. I struggled even though I knew it was useless. I mmpphed and squirmed and managed to crawl across the room. When twenty minutes passed, I was already sweating and breathing heavy.
I heard a noise and thought maybe if it was the kitchen door. No, I checked that door, I thought. No one could be getting inside and if they were, they would be in for a surprise if they stumbled into my room. I stopped struggling and listened again. I didn't hear anything and shrugged my qualms aside. I continued my struggling for a few more minutes until I heard another sound. This time, it sounded like a creak or maybe even footsteps. My fears began to envelope me as I reached for the string. I pulled on it and down tumbled the cup. Some water spilled, but the key was still encased in a block of ice. I motioned to retrieve the ice block, but then I noticed someone else in the room.
"James?" I heard a sweet voice ask.
I looked over and saw her, my neighbor. Oh shit, I said to myself. What the hell is she doing here? How did she get in? I turned away quickly and attempted to move under my bed until she stepped over and picked up the iced key.
"Where do you think you're going? You aren't squirming away that easy, James," she said in a commanding tone.
I looked back at her noticed the small smirk across her face. I also noticed what she was wearing for the first time as well. It looked as if she had been taking a midnight dip in her pool. She wore tight, spandex short bottoms and a halter-top. I had always been a fan of the boy leg short style swimsuits.
"What are you doing here?" I managed to stammer.
"Your parents gave me a key to the house a few days ago. They knew you'd be here, but they wanted someone else able to get inside just in case you were in trouble. Then, I saw you earlier today, but thought it was your sister. Then I remembered your parents saying you would be the only person home and so I came to investigate," she giggled. "Looks like I stumbled upon some one's secret."
"How about you just leave and forget this ever happened. I'll buy you dinner. Just let me go," I began to panic.
"No," she said curtly.
I was at a loss for words. I managed to utter, "Please."
"No," she said again more firmly.
She sat herself in my desk chair and crossed her legs. Her foot was in front of my mouth, as she intended. "Beg, and I might let you go. Kiss my feet to show me how much you want to be released."
I couldn't believe what was happening. Most girls would have been disgusted and ran out of the house, if they had walked in on my situation.
This was unbelievable. It was unimaginable that a very hot girl my age would be interested in this sort of thing. I didn't know what to say or think so I complied and started kissing her foot.
I could tell she had been swimming because I tasted a hint of chlorine from her foot. It wasn't an awful taste and the experience was still very erotic. I could feel my cock bulging hard against my panties.
"I always knew you'd look good as a girl. You always had more feminine features. Why didn't you tell me about this earlier, slave? Now, look what you have gotten yourself into. I'm going to have to teach you a lesson about keeping secrets and not talking to your neighbors. Maybe if you had talked to me more you could have told me about this, but no, you had to shy away. Oh well, I just have to punish you now."
I still couldn't believe this was happening to me. My fantasy was turning into my reality. As I remembered, I recalled her always having a master-like quality. In fact, I even remembered one time when she did order me around when we were little. It was a long time ago and I probably wouldn't have remembered it if she hadn't been ordering me around again. I sucked her toes and kissed every inch of her foot. Then, she raised her other foot and I did the same to her other foot. I noticed her rubbing her crotch as I worked my tongue between her toes and along the soles of her feet. She squirmed and giggled due to the fact her feet were also very sensitive and ticklish.
"That's enough for now, slave. I think I'll like this. I've never had a guy dressed up like this before, but it makes the feeling even more intense. To you see dressed like that, humiliated and helpless…oh. I didn't know I'd like this so much. I have an idea! I'm sure my mom wouldn't mind me sleeping over here tonight. She'll probably work late anyway and not even notice I'm gone. What do you say?"
"Do I have a choice?" I asked innocently.
"No, slave. This will be a very interesting evening indeed," she said with a grin.
Alicia, my neighbor, unlocked my hogtie chain, but kept my hands and feet cuffed. She made me kiss every inch of her long, tanned, beautiful legs and forced me to tell her where the rest of my clothes and chains were. I could either tell her or stay in my position until my parents came home to find me. I believed she would go through with it, hand feeding me and helping me to the restroom until the end of spring break. Since I didn't want my parents finding out and she already knew, I told just her.
"Wow, James. I had no idea you were so kinky!" she exclaimed.
"You know, it is rude to go through someone personal things," I protested.
I regretted my words when I saw her look at me. She walked over and pressed her foot against my enlarged cock very hard.
"Are you talking back to me, slave?" she said with a stern look.
"I'm sorry," I pleaded as she twisted her foot and pressed my cock harder. My face winced as I moaned in pleasure and discomfort.
I gasped at the pain and pleasure of her dominating foot, but she only laughed and smiled. "Oh, this is fun. I think you should know that you are my slave and you will do anything I ask of you. Tell me you're my slave and I am your mistress. Say it, slut."
I looked up at her. My cock had told her I loved what she was doing. She was not only dominating physically, but also dominating me with words through her mind game. I could tell she liked it too because her wetness was apparent in her swimsuit.
"I am your slave, Alicia, and you are my mistress. I'd do whatever you want."
"Isn't that sweet? I need to go home and get some clothes. Then, I'll be back to take a shower and wash all this chlorine off," she said picking up the chain. She checked my wrists and ankles then looped the chain around the cuff chains. Finally, she locked the chain together putting me in another hogtie. "Do you think you will be alright for another half hour?"
"Yes what?" she pressed.
"That's better," she said smiling and left.
My mind was still racing as I watched her leave. What was she going to do to me? I wondered. This was totally unplanned. I had counted on having a weekend alone, but now I was thrilled and scared at the same time. I was lucky to be alive, I thought. I was also lucky to have her discover me and even luckier that she liked the same thing.
I struggled some more, but knew my efforts were fruitless. She had taken all my spare keys and the frozen key. I was truly and utterly helpless. I could scream and no one could help me. Being caught by a beautiful young woman, humiliated, and completely helpless while being dressed in my favorite uniform was too much for me. Within a few minutes of struggling and grinding my cock against the floor I cummed all over my panties and pantyhose. I felt each squirt shoot out of my throbbing cock. I moaned as my sensitive member quivered and tensed. Then, laid there a few moments exhausted.
My mind was wandering when I heard Alicia coming back. I tried to present myself, but she knew something had happened. I looked up and tried not to hint towards anything, but my sweaty face and exhausted breathing must have told her everything she needed to know.
"Roll over," she commanded.
I hesitated and received several hard slaps on my ass. I complied and rolled over. She lifted my skirt and examined the enormous wet spot.
"Well, well, well," she said, "it looks like you were busy in the five minutes I was gone. Did I say you could cum, slut? Now, look at you. You are a mess! It looks like you'll have to take a shower too," she instructed as she began unlocking me.
She had brought rope with her too. I also noticed she had taken her backpack and another large duffel bag with her. I wondered what she had in there, but couldn't examine it as I felt rope encasing my wrists. Alicia unlocked the leg irons and handcuffs, but had also tied my hands. My shoulders were starting to ache, but I didn't want to complain. It felt good to stand up and stretch my legs after being incapacitated for such a long session. Alicia put a collar around my neck and connected the chain. She led me to the shower and was about to undress me when another thought came to her.
"Wait right here," she said.
She returned with a camera and took several photos. I was mortified. What was she going to do with those? She left again and returned.
"I just need some insurance. You see, I'm going to have to untie you momentarily while you strip and take your makeup off and I can't have you running away. So I hid the camera and if you don't cooperate with me, they will be posted at your college and mine," she informed me. "Don't worry. No one will see them if you obey."
She quickly untied my bonds, and I complied in stripping in front of her. I took off the make up and used the toilet. By the time I was ready to begin showering, she was already washing herself. I waited outside the shower door until she told me to come in and help her.
"Could you wash my back, please?" she asked cutely.
I washed her back and moved down to her ass. Her ass wasn't large, but full. It made my cock rise instantly as I washed it and rubbed it again and again. I loved the feel of cupping her butt cheeks in both hands and squeezing. She stepped back and felt my warn cock press against her ass. I heard a slight moan from her, as she pressed harder into me.
"What are you waiting for? Do what you want because after this I'll be the master for the rest of the weekend," she spoke.
I acknowledged her remark by pulling her hands behind her back. I held both wrists with one hand while lathering her anal hole with the other. When I thought she was nice and lubricated, I slowly inserted my enlarged, aching cock. She squeaked as I pressed harder into her. I fondled her large breasts with my other hand, twisting and groping her. She began to moan louder as I smashed my cock into her tiny hole. I rammed myself into her faster and harder until she moaned loudly. I felt her warm juices flowing down my ball sac as I fucked her ass hole ruthlessly. I fingered her clit and pussy with my free hand while pumping faster and faster. She groaned and screamed while her whole body shook with a massive jolt. She fell back on me, exhausted, but I hadn't released yet. She looked back at me with adoring eyes knowing I wasn't done. I filled her anal hole again. This time, I shoved three fingers deep within the folds of her pink, swollen pussy. She screamed louder as I savagely fucked both her ass and pussy while holding her hands helplessly behind her back. I pumped and grinded against her until I thought she would break. Finally, I felt an orgasm forming within my cock. I forced my cock faster and shoved my fingers deeper, rubbing a spongy spot far within her pussy. She moaned in pleasure as I rubbed this spot while still working her ass. I felt her pussy muscles tighten just as I felt the edge of orgasm. I released with moaning pleasure just as she screamed with intense delight. I shot several loads in her ass and continued moving my fingers in and out of her pussy until my cock stopped throbbing. We washed each other clean and got out of the shower.