I don’t really understand my problem. I’m definitely not comfortable with it. I hate thinking about it.
I’m a crossdresser. I’m not gay, I don’t want to be a woman. I like dressing up as a woman.
I can’t remember how it began, what caused it or why I do it. It feels good. It feels naughty. I like the soft texture against my skin. I like the restrictive elements of how tight some of the attire can be. I look at myself in the mirror and I’m disgusted by what looks back… But then I look at the body and I’m in a trance.
My dad works at a shop and my step mum is a P.E teacher. I don’t know how my dad got so lucky… She is thin and a thing of beauty! I catch myself looking at places I shouldn’t from time to time. She doesn’t help herself, wearing leggings so tight that they help reveal mounds and crevices.
Working a four on four off shift is nice, I get a fair bit of spare time. It was a Thursday like any other, Steph (my step mum) was at school and my dad was at the shop. I woke up about 10 o’clock. A nice lie in compared to my 4am starts when I’m in work. I knew I’d be alone for the majority of the day because my dad was on a 12 hour and Steph had to go to a parent’s evening.
I had been looking forward to this day all week. I put a plan I had thought out into motion. I was going to seize the opportunity and try out some outfits while the house was empty. I’m not really sure why I had never tried it before.
After waking up my first thought on my mind wasn’t breakfast, wasn’t a wash. It was crossdressing. I don’t know where the impulse thought came from, but I didn’t care. I got out of bed and headed straight for my Dad and Steph’s bedroom. I stopped at the door. Didn’t open it, I just stood there, frozen. “I better check and see if everyone has actually gone before I do this”. So I went down the stairs and made sure the coast was clear. It was. The operation was a go!
As I walked through the portal that carried me from the landing to my parents room butterflies had grown in my stomach. I was scared but head strong. I was where I wanted to be but at the same time I knew I shouldn’t have been there. My first task was to shop. I needed to pick out what I liked and didn’t like. Steph has been in my life for a long while, so I knew what sort of clothes she had.
Opening the cupboard I started to shake with both excitement and nerves. It was a very very strange feeling to have this new experience of emotions flowing through my whole body. I couldn’t pick one item to focus my eyes on. My eyes where glancing at everything. Dresses, skirts, blouses, bodysuits. It all looked good.
Pausing for a minute, I quickly refocused my attention. I wanted to try things on but I needed to get into shape. I opened Steph’s drawer and picked out a bra. There where fancy ones and a variety of higher end ones, but I needed to be cautious as I didn’t want to make a mess. No one can find out what I’ve been up to. To be safe I chose a basic white bra at the top of the pile.
With no hesitation I put the bra on and shoved some socks in the cups to get a fake bust. Immediately I felt a rush. My heart fluttered and I was immediately errect. I didn’t pay any attention to my now rock hard appendage, instead my mind was already looking for a pair of panties that would be comfortable to wear, and look the part. My eyes were drawn to a polka dot pair that had a little bow in the centre. They where thin but big enough to cover the top of my hard bulge.
As I was grabbing the panties I had chosen my hand felt a smooth sensation that sucked every ounce of awareness I had. What was that? It was so soft. I reached in for it to find it was a pair of black tights (or pantyhose wherever you’re from). I’ve always had a thing for tights. My favourite fetish. I can’t explain the reasons why I like them so much. I definitely don’t need anyone finding out about my attraction either!
I pulled them out of the drawer and slid into them. I felt another rush flow right through my body. I had goosebumps all over but a warmth that coursed through to the tips of my fingers. Next I wanted a dress. There was a sundress I saw earlier in the cupboard that was perfect. It was normal. Had a waist belt on it and was ideal for hugging the figure I had imagined I would look like. I took it off the hanger and put it on.
My look was almost complete. Lastly I wanted some heels. There was an issue here tho, a big one. My feet are a size 7, Steph is only a size 4. But I got looks, I found a pair of black faux leather ankle stiletto boots that fit. They were the finishing touch. I looked at myself in the cupboard mirror and my body was beautiful. I would look back up at my face and just see disgust.
There was an urge from within to play with my look. I pulled my dress up a little, just to slip my hand under the tights and panties. Grasping my dick with a purpose. Looking at my body the whole time in the mirror. Gazing at the beauty. My senses where overloaded. The feel of the tights against my legs, the tightness of the belt that wrapped the dress around my figure. Me feet, warm and high off the floor, angled to cause discomfort but not pain. I was in awe.
Stroking my attentive cock I felt good, I felt weak at the knees at a look in the mirror that made me swoon.
Then it happened.
Not a climax, not a rush, not something I could have ever seen coming. The front door opened.
“Hi Kevin” shouted Steph.
The words seemed to send a shiver deep throughout my soul. All the blood that was flowing so warm, suddenly seemed to turn to ice. My radiated face turned pale like the life had just left my body. I was in a panic.
“Hi Steph” I sheepishly replied. I didn’t even think, I just ran. Still fully clothed I ran to the toilet and locked the door. Sat on the toilet seat and prayed. Steph’s footsteps where like small explosions. I could hear every move, every crack on the staircase seemed to be ear splitting.
“Did you have a good sleep? I’m just here to pick up some clothes for parents evening.” Steph’s voice passed through the locked door seemingly, making me feel very vulnerable. I didn’t know what to do? Should I start to strip? Should I hide the evidence in the sink cupboard? Pretend I’m in the shower? Even if I did come up with a solution my mind had disconnected from my body. I was stuck.
“Yeah, I’ve not long been up. Why do you need clothes? Are you not wearing any?” My panicked state managed to crack a joke.
“Of course I am you Muppet. I need a suit for parents evening”. I could head her rumaging round in the cupboard. Then I realized. I had left her drawer open, I had left the hanger that once held the dress I was now wearing on the bed. What if she wanted these specific heels? I was caught. I thought this is the end. What were the repercussions to be? Would she tell my dad? Would she tell my friends? Would I be alienated?
My mind wouldn’t slow down. “I’ve got what I need, I’ll see you later Kev”. The words of solace. She mustn’t have noticed anything wrong or out of place. I felt safe. As the front door shut, my heart reset and my head started to focus back on my senses again.
I stood up, paying attention to the sound of the heels on the hard tile floor. I was back in the zone. I headed straight back to the bedroom. Opened the door and turned the light on. I was eager to get back to what I was doing. My now flaccid member didn’t take long to get going again.
“What the fuck are you doing Kev”… That was it. That was the exact moment when I knew I was a dead man. My heart skipped a few beats. I was frozen. My soul was no more. Steph hadn’t left, she knew exactly what I was doing. It was obvious. The open drawer, the mess I had left.
“Well?” She asked waiting for a response. Like I was in any sort of state to give a response.
Steph paused for a minute “sit there and let me think what to do”. All my fears had come true, everything I panicked about was to become a reality. I was fucked!
“I think you’re in need of a punishment fit for a sissy like you”. “I can’t believe you’re just using my clothes like that you disgusting little pussy”. “Well? Do you have anything to say?”.
I didn’t know how to respond, I was in complete shock.
“Turn around”.
“Get on all fours, come on hurry up you little sissy”
The name given was going through me like a knife. But I obeyed. I turned round on her bed. On my hands and legs.
I mustered up the courage to speak, “Please don’t tell anyone”.
I couldn’t see her. I didn’t know what she was doing. Then I heard it. The snapshot sound from her phone. The noise was like a volcanic eruption that sent shockwaves through my chest. What proceeded was a explosive clap. The sound confused me at first. Then the sensation of pain spread from my ass to my back. I had been struck. She slapped my ass… What with? I didn’t know, but the pain was excruciating. I turn my head and my eyes caught nothing but a hand in the air. Poised and prepared for another strike.
“Turn the fuck around you little bitch”.
Again. I was in disbelief how much pain one hand could cause. Maybe it was the combination of fear and shock that made it seem so hurtful.
“Close your fucking eyes and turn around”. Steph had never been like this before, I knew she was pissed! She had barely sworn in my presence before. Reluctantly I turned around. I expected my face to be next to experience the agonising pain.
“Open your mouth”. I was perplexed, why did she want this? I was in no position to argue, I was on all fours, with searing pain from my ass. I stayed silent and obliged. I was like a robot, being told to perform a simple task and incapable of saying no.
My cock was still at full tilt and all the while my senses where working overtime in the background. Something brushed past my nose and I thought nothing of it. It wasn’t a hand that it me in the face. It was a moist, sweaty, damp smell. An intoxicating smell, that hit me hard in the face. I knew exactly what it was.
This wasn’t my first time experiencing this smell. I didn’t even get a chance to have one thought.
“Are you going to do your job or what you fucking whore?” I was bewildered by the question. Again not knowing how to really react my body had obeyed the command before my brain had time to even decipher the words in the demand.
I began to bury my nose deep into the task at hand and taste the juices the lay so sweetly on her exposed lips.
My eyes were open but couldn’t believe what they were seeing. Steph stood in front of me completely naked. My own step mum. She stripped whilst my back was turned. She planned this. My tongue was taking in taste with every movement but declined to admit what it was tasting. My nose could smell the sweet powerful scent but denied every knowing.
“Ohhhhahh”. Steph’s moan told me everything I needed to know. She was dripping with ecstasy from her pussy. I didn’t know why she was turned on at the sight of me in her clothes, but I didn’t really care about the why. I was exactly where I wanted to be. It didn’t feel like a punishment at all.
“Stop”. “Turn around, but this time, turn onto your back”.
I edged myself closer to the end of the bed and continued to flick and stroke my tongue against her beautiful vagina. It was a different angle but an angle I enjoyed. She was pretty much sat on my face. There was a lot of weight bearing down on my head but I didn’t mind.
“ohhh Ohhh OHHH”… The moans increased “OHHH FUCK KEV” she bellowed. I knew she came. Her whole body flopped like mine did earlier. Her soul had left her body behind. She was still sat on my face. Her body was slumped over with her head now next to my sizably hard member. As I continued to take pride in my own movement, I felt the point of Steph’s nails stoking my erect shaft through the tights. She toyed with the precum that had soaked through her panties.
Steph knew exactly what she wanted. I was so sensitive even her breath seemed to tease my dick. I couldn’t even dream of something as bizzare and unrealistic as this. The situation no longer felt like a punishment of any sort. Now exposed to the elements my cock after Steph tool it from beneath the tights and panties, seemed to grow bigger than it ever had. I was more turned on than I’ve ever been before.
As Steph licked and teased me, I stopped licking. I was in awe, she took me in whole. I was back in shock again. This was heaven. I could feel every bump on her tongue, I could tickle her tonsils with my tip. Steph paused. She retracted my shaft from her mouth.
“What are you doing Kev, I didn’t say stop?”
I pushed two of my fingers in to her, deep, and started to thrust as I resumed my tasting session. I was focused on pleasing her and I lost track of what she was doing to me. My throbbing dick was lost in a trance. The heat had overcome every part of me. My breathing and heart where out of sync. I was out of balance just from the sheer pleasure. As I was thrusting away she started to moan again. This time the humming vibrating throughout my whole shaft. I could taste the juices staring to ooze out, she was going to cum again. The moans only got louder and more violent.
I lost it. I exploded my load into her throat. Feeling every pulsation and expand into her closed jaw. My skin touching her teeth with every passing wave. “OHHHHH FUUUUUUUCK”… She screached as she came simultaneously with my convulsions.
I could feel the warm cum dripping off my appendage onto the tights and being soaked up. We lay still for a brief but perfect moment, catching our breath. Letting the rush flow free and true. Her beautiful naked body on top of my clothed embarrassment.
All went quiet. All was calm. With one big sigh. Steph got up.
“W-w… What the fuck was that Steph?”
There was no reply.
“That was amazing”. “Why?” I asked.
Steph looked at me, as she stood up. She could barely hold her balance she was still shaking through to her core. The look wasn’t pleasure, or delight. It was disgust. Was she repulsed by what she saw? Or by what had happened? No.
“I have to go back to work. I’ve got a class in half an hour. Let’s just pretend this just never happened.” “Get out of my clothes and get them washed.” It was clear she was ashamed of herself, the way her words fell out of her mouth. She was embarrassed herself. Confused about what just happened. Befuddled about the causality.
All the enjoyment had dissipated. She got her phone out and deleted the picture of me. It was obvious she didn’t want any of this to get out. The looming threat of my crossdressing secret going public was no longer. She didn’t want my dad to find out. She didn’t want anyone to find out.
I was safe.
I took everything off and Steph got dressed, ready to go back to work as if nothing happened. She left without uttering another word. The silence was deadly.
Later that evening we were all sat down for dinner as normal. My dad spoke first, “have you got up to anything today?”
I replied, “not a lot, did some washing and that’s pretty much it”
Steph looked up from her dinner. To my surprise she directed her sentence at me. “Thank you for doing the washing”. A normal conversation, spoken straight. I was a bit weirded out but it came to pass in a moment.
Steph and I have never spoke about the event since, no body ever found out, no body got harmed. It was a confusing experience for the both of us, I don’t know why she decided to do what she did. I’m definitely not about to complain. We get along fine, as if it was all imagined. Like it never happened.
But it did happen, and I will never forget it. I hope you keep my secret too.