Like many cross dressers, I found my habit has a certain ebb and flow. I would bury myself into my kinky hobby for several weeks, only to hide everything away again. I used to have purges too from time to time, where I'd convince myself it was wrong and throw my clothes away, swearing I'd never do it again. The last time I purged was in my mid twenties. I'd been with my then girlfriend for around a year and we had decided to live together, so, in order to keep things secret, I threw all my clothes out.
Fortunately for me, my girlfriend, Teresa, quite enjoyed wearing sexy lingerie, so I got to live vicariously through her, picking clothes and outfits that she could wear. I'd often buy her things too, at the back of my mind wishing they were for me, especially as we were the same size.
One weekend, not long after her birthday, her mother arranged for the two of them to go on a spa retreat for three days and I'll admit, as soon as she told me I knew exactly what I would do. It had been over two years since I'd indulged my feminine side and I couldn't wait to have a play on my own. She left on the Friday and before her car was out of sight I found myself stood by her large wooden chest of drawers. I slid the top drawer gently open, as if it held some magaical artifact and gazed up the rainbow of lace and silk within. Almost instantly my eyes fell upon white lace. As I reached out, my hands were almost trembling as if it were the first time again. My stomach fluttered with nerves as I lifted a white lace thong, soft to the touch, and set it to one side. I found the matching bra and suspender belt too, along with some white lace top stockings. I laid the items out on the bed and began to strip.
I ran myself a bath as I padded naked around the house. Even though I had not indulged my habit in a couple of years, I still maintained a smooth, hairless body. As I sat amongst the bubbles, my mind raced with anticipation. I felt my cock begin to harden as I lay there and even began to play with myself beneath the hot soapy water before snapping myself back to reality. Good things come to those who wait.
As I towelled myself dry, I admired the lingerie as it lay upon the bed. I had bought it for her for no other reason than I wanted it myself. Expensive and deliciously soft, she had worn it under a flowing summer dress. I thought of that day we spent together while I dressed. As I eased the stockings over my legs, I remembered her wearing them as she wrapped her legs around me. As I attached the garterbelt, I thought of how she had playfully lifted her skirt enough for me to see them. As I stepped into the panties, I remembered how wet I had found her to be. As I clasped the bra behind me, I thought of how she had squeezed her breasts in those soft lace cups.
My body felt electric as I dressed, and my hard cock protruded over the top of the panties as they strained to contain me. As I lay down on the bed, the cool cotton sheets only added to the eroticism. As I gently teased the tip of my fingers down my firm stomach, my phone erupted with a call. I answered without looking at who it was.
"Hi, Hun, just letting you know we got here okay", Teresa's soft voice cooed to me down the phone. We made small talk as I lay there in her lingerie and, despite the relative banality of the conversation, I found my head swim with memories of her. As she told me about her room, I began to trace my fingertips over the soft lace as it strained against my cock. I closed my eyes and thought of her lips and the way she would kiss me, how her tongue would seek out my own.
"Are you there?" I was snapped back to reality. "Are you okay?" she asked.
"Yeah, sorry. Really tired." I excused myself vaguely. She suggested I get some rest, and with that, she happily ended the call to go for a dip in the pool.
As I placed my phone down on her bedside table, my mind thought of the contents of it's drawer. It slid open silently and nestled among the bits and pieces sat a flesh toned, veined, and not particularly small dildo, resplendent with a gorgeously tight looking pair or balls. We enjoyed using toys in our play, but so far I'd never experienced this particular one. I took hold of it and couldn't resist easing it into my mouth. I closed my eyes and the memory of past oral encounters came flooding back to me.
I missed it. I missed getting a guy so hard it hurt. I missed teasing him. I missed strong hands desperately clawing at me. I pulled the toy from my mouth and covered it in lube from the drawer. Laying on my back, I spread my legs wide and pulled my panties to one side. With one lube covered finger I sought out my tight, smooth ass hole. Gently circling before pushing a single digit inside, I felt like I could explode there and then.
Spreading my legs wider, I lined up the tip of the toy with my ass and, gently but firmly, I pushed. Once again the memories came back. I breathed deeply as my ass spread to accommodate the large toy. The pressure inside me seemed to grow until I felt the familiar jerk as I took the flared head of that gorgeous fake cock. I lay there for a moment, stockinged legs spread wide, one hand holding my panties aside, the other on the base of the toy, my cock now free from its lace prison stood hard.
With my eyes shut tight, I firmly pushed the toy deeper into my ass.
"Oh god!" I cried out breathlessly. Was it always this good? Why would I stop doing this? As I slid the toy gently back and forth, I could feel my entire body tingling. My cock was like stone, solid. It was then I remembered the last guy to fuck me and the last position that made me cum so hard.
Without removing the toy I rolled on to my front, my face pushed against the pillow. I reached down under my stomach and gripped my cock allowing me to fuck my now stationery hand. With my other hand I began to fuck my ass with the toy. Fuck being the operative word too. I buried it deep to those fake balls before pulling almost all the way out before plunging it back inside. I missed strong hands on me, hot breath on my neck. I missed the weight of a person behind those thrusts.
It took no time to feel that familiar feeling at the base of my cock as my orgasm beganbto build. I wanted more, I had to reenact my favourite position. Pulling the toy from my ass, I placed it on its flat base. I hurriedly straddled it, pushing it inside. I loved this position the most. Being in charge, fucking them, jerking my big, smooth cock close to their face as I became the biggest whore in town. The bed moaned and creaked as I bounced on that fake cock, my hand a blur as I worked the length of my own hardness. I continued to bounce as my cock swelled. My hand still a blur as I shot arcing streams of cum across the bed. My ass rhythmically tightening around the hard shaft of the toy.
I fell forward, exhausted. I could feel the cum covered sheets beneath me but I didn’t care. The toy was no longer inside me as I lay there and I felt empty. I waited for that post orgasmic chill, the subsidence of my horniness. My cock stayed hard, my mind still racing. I reached behind me and slid two fingers onto my still twitching ass hole.
This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than Lushstories.com
with this note attached, it has been posted without my permission.
<a href="https://www.lushstories.com/stories/crossdressing/returning-to-old-habits-1.aspx">Returning To Old Habits</a>