caught in drag
Introduction:
I was in my teens and always horny. I loved to where womens underwear and that is where the trouble started
I used to go over to their apartment most days during the week. They both worked and the place was all mine. Normally, the first thing I would do was double lock the door from the inside so that they couldn’t open the door without me unlocking a deadbolt from the inside. That way I knew I wouldn’t be walked in on unexpectedly. Then I would strip naked and head for the spare bedroom. The queen sized bed had a footboard and a headboard. I needed the headboard because I figured out a way to give myself an awesome blowjob using it. I would prop up my head using several pillows and then lift my legs up over my head and hook my toes at the base of the headboard. Manipulating myself in such a way would bring my cock right up to my mouth. I had to be very loose and limber to make it work. If I was stiff or had not yet taken a poop or had eaten a lot of food I couldn’t bend myself in a tight enough ball to get my cock all the way into my mouth. There were times when I would just jack myself off with one hand while I fingered my asshole with the other and then shot my load down into my mouth and on my face. While it felt good, it wasn’t what I needed. I loved the feeling of that throbbing stiff cock in my mouth. If I could do everything just right, I could actually get my cock all the way to the back of my throat. One time, I shot a load so hard that it went right down my throat without ever even stopping in my mouth. That was kind of a drag, because I loved the taste and texture of my cum as it filled my mouth. It took some length of time to really master the technique so that I got all the enjoyment I could out of my autofellatio.
Once I had successfully sucked myself off, I would carefully inspect the bedding to make sure I had not splattered any cum on a pillow, bedding or headboard, If I had, I would lick up the excess and then wipe it down with a wet towel. My next step was to open the underwear drawer, As soon as I smelled the contents and felt the fabric, my cock would get stiff as a board again, even though I had just drained it. I would rub various pieces against my body. I would jack off through the legs of her panties. Inevitably, I would cum on one or another of her things and have to lick off the mess. I would then put the piece in the dirty laundry, covering it up with other clothes so as not to be too obvious.
After blowing two or more loads, I would relax on the couch and look at some of the porn mags that they kept around. There was always pictures of stiff cocks sliding in and out of swollen pussies or slamming balls against the chin of a girl as she choked on a massive load. It wouldn’t take me long before my cock was so stiff it was laying on my stomach with the head past my belly button and the one eye staring at me. The large purple head would look to be bursting and precum would always be starting to form like dew at the tip.
I started to get a bit more bold with the passing of time, never being caught or questioned about my activities. I finally began to wear the panties and bras, along with slips and sundresses. One of the favorite things was nylons. She only had a couple of pairs of real nylons. The rest were pantyhose. I liked the nylons because I could put on the garter strap and have my cock free to tug on. The limited supply meant that the only time I got to where the nylons was when I could find a dirty pair in the laundry.
I began to put on makeup and used hairspray to put my hair into more feminine styles. I would get completely made up with bra, panties, nylons, garter belt, a sundress and full makeup and then I would view myself in their living room mirror. I probably looked ridiculous, but at the time I thought I was hot and I would cum in massive streams when I saw myself. I would hike up the sundress and pull down the panties and beat the crap out of my throbbing cock until I shot my load on the mirror. Then, I would get on my knees and lick the mirror clean. Sometimes, I would make out with myself, kissing the mirror. After these more adventerous times, I would have to be very careful to put everything back in the right places and clean up really well. One time, my sister in law took me aside and asked if I had been kissing the mirror. I must have turned four shades of red and didn’t know what to say. In my defense, she said that she knew it was me and understood that I was shy and probably practiced with the mirror to make sure I knew how to kiss a girl. I just agreed, acting a bit embarrassed, and nothing more was said. Needless to say, I was doubly sure to check everything after that, before I would leave for the day.
Once this particulare summer was over and I was back in school, my opportunities to indulge in my fetishes was severely limited. I could only enjoy an empty apartment when both my brother and his wife were gone for the day on weekends, and this was a rarity. During this time, I ran into an elementary school buddy that I had lost contact with several years before. I had a car, not that usual for a 17 year old in my school, and my friend Terry approached me one day in the parking lot. Both of his parents were alcoholics and physically abused him from time to time. He was 5’8″ tall, pale and small boned. He had shoulder length brown hair that was naturally wavy. When he approached, I noticed bruises on his face. He said his mother had gotten upset with him and had kicked him in the face as he stood at the bottom of a stairway. She was standing several steps above him and actually hit him in the face while wearing high heels. It had sent him backwards through their front screen door and onto the porch. Not waiting to be beaten any more severely, Terry ran from the house and had slept in a park the night before. He came to me to ask if I would help him gather all of his belongings from his house so he could run away to someplace safe to live. Back then, there was no child protective services and kids were routinely abused by parents. If he had gone to the police, chances were that they would have just taken him back home forcefully, if necessary. I couldn’t refuse him, so we skipped the rest of the school day and went to his house while his parents were out. We gathered his clothes and a few personal things and left.
We hung out for the rest of the day at my brothers apartment and when my brother and sister in law came home that night I told them what had happened. My brother was always a really generous guy and, since his apartment was on the second floor of a converted house, he had space in an attic area above the apartment where he let Terry spend a few nights.
A few nights turned into a few months and soon Terry had a job at a local restaurant and had stopped attending school. He worked odd hours and was able to enter the attic through a back stairway that let him avoid bothering my brother when coming home late. He paid my brother what he could for the space and stayed very quiet when he was in his room.
Months went by and I wasn’t over at my brothers much because of school and them being home most weekends. I entertained myself in my own bedroom by putting on some panties I had taken from my sister in law and autofellating whenever I could. I had become quite adept at the contortions I needed to do to enjoy the taste and feel of my throbbing cock in my mouth and the sensation of my cum as it went down my throat. I rubbed my balls through the lacy panties to heighten the experience and sometimes fingered my asshole as I came.
My brother was over at our house one day and casually mentioned that he and his wife were going out of town for the weekend to visit some friends. Leaving Friday after work and not returning until Sunday night gave me a good long time to indulge in some long periods of cross-dressing and masturbation. I was so excited when Friday evening finally arrived that I could hardly control myself. I raced over to their apartment and locked the door as I always did. I was about to strip and start my fun when I remembered that Terry might be upstairs. I went to the rear doorway that opened to both the attic and the back entrance and tried to open it, but it was locked from the other side. Evidently, they had allowed Terry to installl a lock on his side of the door. I knocked and called out Terry’s name, but got no response. Since I knew he worked at the restaurant most evenings, I didn’t give it another thought and began my normal ritual. In no time, I was laying on the bed with nylons and a garter belt on. Lace panties adorned me but were pulled partly down to expose my cock and asshole. I had full makeup on and had stuffed a couple rolled up socks in a bra to finish the look. I had my cock buried ball deep in my mouth and had lubed my ass so that I could get 2 fingers knuckle deep. I was in ecstacy as I began to feel the precum flow out of my cock, knowing I would soon be rewarded with a load of cum.
Out of the corner of my eye, I thought I saw a movement. It wasn’t anything clear and I didn’t hear any noise, but it was enough to break my concentration. I uncoiled myself from the bed and rose to get a better view out the bedroom door. As I stepped through the doorway, completely in drag and with smeared lipstick on my lips and my dipstick, there stood Terry. I didnt know what to say. I was caught. My secret would be out. He could ruin my reputation. Terry didn’t say a word. With very little movement, he undid his belt and dropped his pants. As he did, he unleashed what could only be described as a monster. His cock was so different from what I would have expected to be attached to this small pale man. It stood 8 or 9 inches, cut with a beautiful throbbing purple head. It was not fat but by no means thin. I could see the veins running along its length. He reached down and cupped his balls and began stroking the shaft with his other hand. “You looked pretty busy in there”, he said smiling. “I didn’t want to interrupt you. Now that you are here, though, I thought maybe my cock would be a bit easier to reach.”
I had not thought about Terry as a sex partner. I didn’t know he was into guys and really still wasn’t sure. I figured maybe I was just an easy way for him to get off. Never the less, his cock looked delicious and I was still in need of a load of cum, so I motioned to him to join me in the bedroom and went back in and laid down. Terry wasted no time in removing the rest of his clothes and climbed on the bed straddling me. His cock was bobbing up and down with his pulse and was almost in my mouth. I braced my head on the pillow propped up against the headboard and reached around Terrys ass and pulled him towards me. He slid his stiff dick deep in my mouth and gave out a noticable moan and gasp as I wrapped my lips around it and began caressing the shaft with my tongue. We matched our rhythm instantly and within a minute or two I could feel his precum in my mouth. His throbbing head grew and his thrusting became more rapid. Soon he shot his load in my mouth and I struggled to swallow it. Some escaped and ran down my chin and onto my chest. He continued to push deeper in my mouth until his cock finally began to go soft. As I began to clean the excess cum from my face and chest, to my surprise Terry slid down to my cock and wrapped his hand around the shaft. He began stroking me and moved to a position between my legs. I raised my butt off of the bed a few inches and he began to suck my balls. His free hand moved to my asshole and he inserted a finger. He wasn’t gentle. He jammed his finger in as far as he could and began to match the stroke of my cock with the movement of his finger in my ass. I was rising up and down on the bed at the same time and then he slid not one but two more fingers in my ass. I groaned and shuddered. I thought I was going to cum right then, but he grabbed the base of my cock firmly and held it still for several minutes until I began to relax. He then started fucking my ass with his fingers again and took my cock in his mouth. He sucked me for several minutes and then sat up a bit to get a better view of me. He reached up and squeezed my bra, commenting that I looked great. Then, with a smooth movement, he raised my butt off the bed and quickly slid his cock into my crack. His aim was perfect and his saliva that had dripped down from him licking my balls had lubricated my asshole along with his fingers loosening it up. His cock entered and when his large head was completed in I felt the pressure lessen and his cock slid in several inches. He raised my legs, still in nylons, over his chest and held them there as he proceeded to fuck me for several minutes. He would stroke his cock in shallow lunges for a while and then drill deep, until his cock couldn’t go any deeper. Soon, he let my legs down and asked me to roll over. I did and he immediately remounted me from behind. He reached under me with his hand and again began to stroke my cock. His other hand grabbed at my bra and massaged the fine lace and also ran his hand down my stomach. His mouth came down to my neck and he began to suck on the back and side of it. I was so hot I knew I was going to cum. I reached between my legs and removed his hand and started beating my cock hard and fast. Terry, sensing I was going to cum, began to quicken his pace in my ass and soon we both came in momentous spasms. I shot huge loads of cum on the bedspread and he filled my ass to overflowing. We were sweating and panting and totally spent. As his cock again began to go soft he let it slide out of my ass. It popped as his head finally reappeared.
“Your sister in law told me that you were getting dressed in her things. I didn’t believe her so she told me to sneak in here when they were gone. I guess the whole thing has been such a turn on for her that she has been fucking your brother constantly to relieve the pent up sexual energy. She came up to the attic one day when your brother was away and fucked me until I couldn’t move another muscle. I’ll have to let her know that she isn’t the best piece of ass in this place!” Terry smiled at me and I realized that I didn’t need to hide anymore. From that day forward, my sister in law and I shopped for clothes together and she always helped me to pick out just the right things to accentuate my body. Both she and I benefit from Terry living in the attic and my brother had no idea what is going on.
