Caught cross-dressing   added 6 years ago
  By: Chris123uk  Age: 29  Country: United Kingdom

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Views: 4500
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Categories:
Tags: ladyboy Teenaager knickers ass private uniform playing bisex gay old jerk secret
Location: Anywhere
Roleplay: Other
Fulfillment: Act on it
Nature: Humiliating

I’m a 23 year old male with a lot of spare time. When everyone is away on vacation, I dress up carefully in my sisters clothing, making sure everything is perfect and I look beautiful in her makeup. I place a wig on gently and adjust her tartan skirt and pop socks in the mirror so I look like a slutty college girl. I usually spend a lot of time in the house like this, washing dishes or doing other chores.

 

Once, I nearly got caught by the gas man who came around knocking at the door. I’ve dodged a few bullets during my time exploring this side of me, except for one very memorable dream where I let my guard down.

 

This is what I remember of the dream.

 

My neighbour rarely leaves his house and lives retired and alone across the street. One day, during my ‘private time’, he comes around and walks right in. To this day, I don’t know why he didn’t knock. Maybe it was because back in his day, the neighbours were friendly and open and didn’t lock their doors and it was customary to just walk in as long as you called out as you did so. Or maybe I messed up and didn’t close the windows properly and he saw me dressed like a college slut. Either way, my heart nearly stopped when I was confronted with him in the passageway. I couldn’t scream or even speak and nearly fainted in sheer fear of the consequences of being caught like this. However, he said “hello, where is your mother?”.

 

I replied, “she is away at the moment”. “Oh?”, where have they gone?”, he said as he closed the front door. I was in utter shock and my knees were trembling. “Spain, as usual this time of year”. He put his head down and took a deep breath and said, “So why aren’t you studying today? Don’t you girls prepare for your midterms this season?”. I wasn’t sure how to respond but I could see the anxiety in his eyes as he eagerly waited to see if I would play along with him and pretend to be a college girl. It seemed like an eternity and I eventually replied with “...yes”.

 

...”but I got the day off today”. I immediately felt immense heat rush through my veins and I was breathing deeply. After some time talking with him like I normally would, I made him a cup of tea and began to fit quiet easily into the role of a college girl. I almost forgot who I was but still rarely made eye contact with him during our chit chat. I couldn’t take the step to completing the character by forgetting how awkward this situation was. But eventually he complemented me, saying how pretty I looked. Instantly, I smiled and felt bashful. I couldn’t stop smiling and he obviously noticed this. He couldn’t keep his eyes off my skirt and pop socks and I knew he was watching my ass when I was doing the dishes.

 

At this point I felt completely comfortable around him and began giggling like a girl too. We joked and flirted and I was so turned on by the look on his face. I purposefully reached over the breakfast table or up onto the top shelf to grab things I didn’t necessarily need to make tea or a snack neither of us necessarily wanted, just so that my skirt would ride up and my cotton panties would show. His cock was obviously sticking out of his trousers and I began thinking about what it was like.

 

SECOND HALF

After a substantial amount of small talk, I felt very secure and very comfortable.  I would play with my hair or walk like a girl, but I never over did it.  Ironically, my behaviour was not rediculous.  I just adopted the character so well, I convinced myself that I was a pretty girl - and no longer a 23 year old man.

I didn't want him to leave.  I didn't know if and how he was going to advance on me, but I was sure that eventually, he would want to have some sort of sexual contact with me.  I wasn't quite sure what I wanted in the long run, but I acted on every impulse - one after the other.  The impulse to be cute for him.  The impulse to show him the colour and fabric of my panties (white, cotton - with BARBIE GIRL in pink letters accross the ass), by reaching the top shelf for things in the kitchen.  The impulse to persist with  the rubbing pain in my foot from the high heals that were tight and very high healed.

It became almost like an obsession to please.  I didn't care now about anything, except keeping him pleased.  So I offered to cook him some food.  He said he would help me cook, and occasionally we bumped into each other in the kitchen or whatever, and he would touch me with the back of his hand or with the lump in his pants.  He was very turned on, and I was surprised that he contained himself.  This turned me on.  The first contact, when the back of his hand brushed over my left asscheek gently, sent shivers down my leg and I cum a little in my panties.  No joke.  I actually cum a little bit, in response to his hand brushing my bum!

After some time cooking, and being touched up occasionally, he noticed my excitement.  I'm not sure how much cum was in my panties at this point, but it was getting difficult hiding my rock hard cock under the skirt.  Without saying anything, he lifted my skirt and starting kissing my thigh and ass like a mad man.  He was almost in a state of panic, as if he needed to get to my asshole to live!  He pushed me over the breakfast counter, and pulled my panties.  My cock got stuck in the panties around front, so he hastely reached around to lift it off.  

Without losing a second, he put his tongue and nose in my ass crack and reached for my asshole.  The sloppy wet flesh worming around in my ass crack continued for about a minute, as he breathed frantically and made funny sounds - like he was desperate.  He then progressed to licking the whole of my asscrack from bottom to top.  Running his tongue frantically from the back of my ball bag, right up to the top of my ass crack - like I was a human lolly pop!  Then he dug in again to reach my little hole.

I needed to make it easier for him, so I quickly got up on the counter and used my knees to position my legs more spread - and to dip my back so I could push my asshole out.  "That's a good girl".

He got his cock out and pushed it into my asshole.  I had no problem at all getting his 5 inches up me.  He was too weak to put much force into his thrusts, but it was sliding in and out of me.  It felt really nice when the tip of his cock slid out of my asshole, so I could feel the curve of his tip on the rim of my asshole.  "don't tell anyone about this little girl - or I could get into a lot of trouble - ok?"

I looked back at him and out of no where, I said "I'll do anything you want".

At this point he started to build up and I could feel his cock pulsing slightly.  I had never experienced a fleshy penis in my ass before; especially a pulsing one.  When he started to pulse up in my asshole, I felt a tingle in my belly that girls must get too.  My blood boiled and my heart/breathing raced.  With deep breathes he said "Oh...I'm gonna cum...".

I was hysterical with passion and excitment and lust and emotion.  I randomly screamed out "make me pregnant sir".

Then he erupted.  I noticed the final thrust being full of surprising strength.  His cum was so warm and the pulsing in his cock rocked my world.  His big hands holding my small bum/thighs on each side of me - emptying himself inside me - making odd sounds/grunts as he stood behind me...emptying himself.

I haven't stopped meeting him since, and we experiment with all kinds of things now.  At the moment, he enjoys watching me fake cry so that my make up runs down my face - and wanking for about 1 hour, whilst I just sit there talking with my girly girl voice and waiting for his load to mix in with my tears and make up.  He likes it when I say sorry, and he always tells me how pretty I look.  I love him.




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