Everyone has a Freak Flag

So for the most part, having sex while crossdressing is a bit of a fetish and once people know you are into it they are now free to share their own fetishes with you. That's where my next life lesson comes in and I have a couple of stories about people doing some surprising shit near me or to me.

Around 26 years old, I was now going by the name Amanda and I met another crossdresser named Missy who I liked to hang out with and dress. Missy and I generally hung around either at her house or mine. Usually we dressed up casually, did our makeup, and just watched TV or played video games, no big show of it. On two occasions we hooked up and this is about one of those times.

We were at Missy's house and it was past midnight. Missy lived in the basement of her parents house; but entry to the basement was separated from the main house so the only ways in or out were through a door to the outside and through a door connected to a garage. The garage door was always locked and Missy's parents never came into the basement at all. After all, Missy was paying rent and this was her place. We had been drinking rum, smoking weed, and playing PlayStation for most of the evening and were winding down. I always brought an overnight bag full of my makeup and some clothes even though I normally didn't stay the night. Missy would tease me about my bag a lot because I always had lube and some sort of toy in it - a dildo, a butt plug, whatever. Missy started going through my overnight bag and teasing me about what she would find and lo and behold, she stumbled across a glittery purple, 10 inch double headed jelly dildo! It was new in the package and I had sheepishly purchased it a day ago from a sex shop downtown and then quickly stuffed it in my bag to make my getaway. Missy was hysterical about it and was not going to let me live this down. She opened it up and waved it around in the air laughing her ass off. Then she suddenly got a grin on her face, and said "Wanna try it!"

In no time Missy and I were on the floor. I was down to my underwear - a basic set of white cotton string bikini panties and a white lace bra. Missy somehow was only in a satin camisole and white knee socks with no panties at all! Missy got on all fours with her ass in the air and I squirted lube on one end of the dildo. I slowly inserted the dildo into Missy's ass and gradually worked it in and out until it could go at least a third of the way in. I squirted lube on my fingers and pushed them into my ass as far as I could reach to get the lube as far in as I could. I got on all fours with my ass pointing toward Missy's and inched backward until my ass could just touch Missy's ass. I pulled the back of my panties down, leaned forward, and placed the top of the dildo in my ass. I slowly leaned back against Missy's ass and she let out a stream of curse words - "Holy Fucking Shit, Stop!" Apparently, I was not lubed enough and was driving the other end of the dildo deep into Missy's ass. We reset and this time Missy held the dildo right where it entered her ass and I rocked back and forth driving the dildo in and out of my ass until I was nice and slick.

We got a nice little rhythm going, rocking back and forth with our butts pressing together on every back stroke. We were both massaging our own cocks and I could feel the pressure of the dildo against my prostate. Just as I was really getting into it, Missy shouted "What the fuck, Caleb!" and I looked up to see Missy's 18 year old brother standing over me with his cock in his hand masturbating like crazy. He crouched over me like he was going to sit on me and I felt his warm cum hit my back. Missy and I both got up from all fours and Missy chased Her brother out of the room shouting and cursing all the way. I toweled off to go home and there was more cum on me than I could ever imagine. Basically Missy's brother had snuck into the basement and had been watching us for a little while. He knew we dressed up and must have liked to watch; but this time he just couldn't take it anymore. He left a huge pool of cum on my back and some in my hair.

The next experience I want to share is the time I called a female escort to my apartment. I was going through a bit of an identity crisis and had packed up all of Amandas clothes, shoes, and makeup to drop off at a donation box somewhere. I suppose I thought if I fucked a real girl I could get everything out of my system, so I found an ad for an escort. When she showed up she was ice blonde, thin, and tiny, with elven facial features. She had large grey eyes and a slender face. She was very pretty; but her face was slightly wrinkled and worn and did not match the almost child-like proportions of her body. In hindsight, she was likely much older than I was and also may have been a bit strung out on cocaine, or had an eating disorder, or both; but who really knows. I remember she seemed confident and in control and I wasn't worried about her welfare.

As soon as she arrived, we said a quick hello, she asked for the bathroom, and she went straight in to clean up and get changed. When she returned she was wearing a white gauze-like nightie and no panties. I vividly remember she had no pubic hair at all and very prominent hip bones. She asked where the bedroom was and I led her there. Once in my room she almost immediately noticed my large dildo and a bottle of lube laying on the nightstand and asked if that was for her. I blushed a bit and said no, then quickly raked the dildo and lube off into the nightstand drawer. She moved around my room looking at all of the things in boxes along the floor and stopped at a box of high heel shoes. She stared at me for what seemed like forever and finally asked if I liked to dress up. I replied that I did at one time but not anymore.

She pulled a ziplock bag of makeup from one of the boxes and told me to sit down. She dumped the bag of makeup on the bed and picked up a bottle of foundation and some brushes. She grabbed my chin and demanded, "Look up" and started smearing foundation on my face with her fingers. The escort applied foundation, eye makeup, and lipstick to me, then stepped away and started rummaging through a box of dresses. I could see my face in the mirror and I had deep red lips and nice dark eyes; but overall the makeup was a bit rough. The escort pulled out two dresses: a semi-formal, red cocktail dress and a silver, form fitting, spandex, sequined mini dress. She stepped into the cocktail dress and spun around, "zip me". I zipped her up, but the dress swallowed her and hung slightly off one shoulder. She handed me the silver sequined mini dress and I pulled it on over my head and smoothed the sequins over my body. I had found my favorite auburn wig and put it on as well; but the escort pulled it back off and handed me a cheap blonde party wig with malt pink highlights instead.

She next went through a box of shoes and pulled out a pair of sky high, black patent leather platform heels, handed them to me, and said "find some panties". While I looked through the various boxes for panties, she was looking through the dresser drawers of my regular clothes. I was about to tell her to stop when she pulled a pair of denim shorts and a belt from the drawers. I watched as she lifted the cocktail dress and pulled on the shorts underneath and threaded the belt through the loops. She then took the large dildo from the nightstand drawer, unbuttoned and unzipped the shorts, shoved the dildo into the shorts, and finally buttoned and partially zipped up around it so it was jutting out like a strap-on. She then cinched the belt tight around her small waist and gave me a long expressionless stare, "turn around".

I turned around and the escort guided me down onto all fours on the edge the bed and then she lifted my dress from the back. She pulled my panties down, fidgeted with something, and then wiped a well lubricated set of fingers across my asshole. She then leaned in closer and I felt the large dildo slide into my ass halfway, giving me a filling sensation. She shifted her feet forward to get closer and pushed the dildo even further. I felt an immense pressure inside and the dildo felt like it was hitting my pelvis when she placed her hand on my shoulder and lightly pushed me down until I was lying on my face with my ass high in the air. I could feel her shift behind me and push a little more, working the dildo deeper inside. I felt what I can only describe as a pop deep inside and the dildo immediately slipped even further in. I could feel the fabric of her cocktail dress pressing against my ass and her finger nails slightly digging into my hips and buttocks. She began moving the dildo in and out with her hips and I could see my stomach heaving out each time her hips thrust. She pushed faster and faster and all I could hear were the sucking and squishing sounds of my asshole expanding and contracting to accommodate the dildo. She fucked me for a good 15 minutes before finally backing away and pulling the dildo out. She removed the shorts and dildo contraption and tossed it to the corner of the room. The next sensation I felt were her fingers tracing around my asshole and one by one inserting them inside. I felt her fingers push forward into me, then a pause, and more fingers pushing in, followed by a sensation of fullness. I pulled my long hair to one side and glanced back over my shoulder to realize the escort now had her entire hand in my ass almost to her forearm!

The escort began to move her arm slightly in and out of my ass; but never removed her hand. I could feel her moving her fingers around inside of me, like she was slowly making a fist and releasing it again, over and over. Waves of pleasure ran through my body like I was about to come; but I never did. I was perched on all fours on the edge of the bed and my knees and thighs would shake uncontrollably when the most intense waves would hit. I began to rock back and forth on her arm, pushing her hand and fingers deeper and pulling them back again. The escort pushed my dress further up my back, almost around my neck now, and ran the finger nails of her free hand up my spine and back down to the small of my back. I was fully in the moment now and gyrated my hips like a stripper giving a lap dance, rocking back and forth on the arm in my ass. The escort pulled my panties down to my knees and instructed me to lift my knees, so she could take them off. While I was shifting from one leg to the other, I looked down and noticed a large puddle of semen on the bed below my cock and a long, thin, glistening string of semen running from the tip of my cock down into the puddle.

The escort took my panties and, with her free hand, wrapped them loosely around my cock and started to stroke, running the panties up and down my cock. At almost the same time, she began pushing her fingers against my stomach from the inside of my ass. I could feel the pleasure waves coming back again and began rocking and gyrating on her arm. I could feel the waves getting stronger and stronger until a huge wave ran up my legs and into my back as I pumped cum into the escorts hand and into the panties wrapped around my cock. The muscle spasms from my orgasm were so strong that my hips joints and back popped sending shivers down my spine. After a few minutes the escort slid her hand and arm out of my ass and I heard her take a step back. My asshole was still tightening and loosening in rhythm with each smaller wave that passed through my body. The panties were still loosely wrapped and clinging to my cock, soaked in my cum. I heard the clicking of heels as the escort walked down the hallway to the bathroom. I heard the sink water run and, shortly after, the sound of heels clicking through the living room, followed by the sound of the front door opening and closing. I composed myself and hobbled into the living room, on weak legs, wearing only the silver sequined mini dress and pink and blond wig. I had decided that night, being a boy/girl had its benefits and I began unpacking my clothes back into my closets.

On later inventory, I found the escort had left behind her t-shirt and shorts, a pair of cotton panties, the see-through nightie, and fingernail scratches up and down my back, hips, and butt. She upgraded though, as she left that night wearing the red cocktail dress, a nice pair of heels, Victoria Secret panties, real pearls, and holding a satin clutch purse and my iPod :)