Getting Caught.

I've been caught a few times.  But this one was at my grandma's house.  My grandma knew of my crossdressing.  She didn't mind it.  She didn't really understand it either.  But, if I wasn't out drinking or doing drugs then it was ok with her.  As I was saying I was at my grandma's for the weekend.  I was around 19 yrs old.  My grandma was out with her friends for the day.  So I decided to dress up.  As I brought some stuff with me from home.  And my grandma would get some stuff from time to time.  Or she would give some of her old stuff she didn't wear anymore.  Let me tell you what my grandma was no elderly looking woman.  She always tried to stay with the times fashion wise.  Hair, clothes, shoes, ect. You know what mean.  And yes like most grandma's she love to wear pantyhose just like my aunt.  Thats another story.  Well since I had the house to my self I decided to change into something more comfortable.  I went into my room which was the guest room and got undressed.  I put on some biege pantyhose, a bra.  Went and walked into my grandma's room and put on her jean skirt that was above the knee.  A jean button up top as well.  I brought some black 3 1/2 inch open toed high heels.  I slip them on did my make up and put a wig on that was auburn colored.  I went into my grandma's room to take a look at myself in the mirror to see how I looked.  I thought I looked pretty darn sexy if you asked me.  As I come walking out of my grandma's room.  There was a guy standing in the living room.  It was one of my grandma's friends who came over to drop something off.  He turned around and he looked right at me.  We both were like holy ****.  Not out loud but expressions that day were louder than words.  He dropped off my grandma's mail and he turned around and left.  As he closed the door I hurried over to the door to lock it.  I was a bet freaked but I have been caught before.  But, not by one of my grandma's friends.  After a bit I decided to change.  After I changed I was watching tv wondering about my grandma's friend.  Let me clear some thing up.  I did know him while I was growing up.  He is a real nice guy and a good friend to the family.  So, for him to catch me dressed up had me feeling awkward and weird and scared.  Anyway as I was sitting there the sliding door to the back yard came open with a knock at the same time.  It was him.  He asked if he could come in.  I said sure.  As he came in I got real flush and embarressed.  He sat down and asked where my grandma was at I said she was out with some friends.  He asked do you know when she will be back I said no I don't.  He asked why were you dressed like that.  I looked at him paused for a bit.  He said well I told him that I like to wear womens clothing.  As I like how they make me feel.  He asked if my grandma knew I said yeah she knows.  He said anybody else.  I told him yeah a few people.  He asked so you like to dress like that then.  I told him yeah I do.  He said would you dress like that for me.  I looked at him and said if you would like.  Thinking god your kind of a creepy old fart.  I asked would you like me to now.  He smiled and said yes if you would want to.  So I nodded and got up and went into my room grabbed my stuff and went into my grandma's room.  I opened the door a little while later.  Wearing some off black pantyhose, a black skirt, white blouse.  A black coat that went with the skirt.  A pair of black 4inch pumps I got from my girlfriend.  Wearing the same wig.  And had my makeup on.  I walked out into the living room where he was sitting.  I stood in front of him and asked if he liked what he saw.  He said yes.  I walked over to the couch and sat down.  Crossed my legs.  Hearing the swish sound from my pantyhosed legs.  He kept looking at me and my legs.  He got up and sat down next to me.  He put his hand on my leg and was rubbing it.  That felt so good and then he leaned into me and kissed me on the lips.  Even though he was older it felt so good.  As he was so gentle and not rough.  As we were kissing for a bit on the couch.  He started to slide his hand up my hosed leg.  Getting closer to my crotch.  I was as hard as a rock.  He stopped just short of touching my ****.  And kept his hand there as we were kissing.  I started to glide my hand around his crotch area squeezing his ****.  Feeling it get hard.  I started to undo his pants and he helped a bit.  I started kissing his neck and then went down on him giving him head.  Hearing him breath heavy and hard and telling me how good it feels.  I could start to taste his pre ***.  I felt his hand on my head having me go a little faster.  Then blam he came.  And boy did he *** alot.  I tried to swallow what I could as I liked how *** tasted and it seemed to turn him on.  After I was done he just sat there for a bit.  I got up and went into the bath room to wipe off any *** that I didn't swallow.  After which I went back out into the living room.  Where he was sitting.  I sat back down next to him.  He looked at me with I can't believe that happened look.  But, it was a good look.  He said I probally better go before your grandma gets home.  I agreed.  As I didn't want her to catch us doing anything else.  I walked him to the screen door and he kissed me one more time and said see you sweety.  And left out the back way to his house.  I stood there feeling slutty a bit.  Which felt realy good actually.  I decided I better change before my grandma gets home.  So I ended my night with a jack off session in my slutty secretary outfit.  Changed before grandma got home and just hoping for another visit from my old friend.

sexyblackpantyhose sexyblackpantyhose
31-35, M
18 Responses Sep 15, 2009

was this situation a man dressed as a woman going down with another man?

Seems like you found a good companion to take care of the "friend with benefits" box. You could probably spend some time at his house dressed up pretty often.

Considering this was almost 5 yrs ago, I'd be curious to know what happened since then with him? What's going on with you now?



Very hot. Story.

It reminds me of the time I was in Gran Canaria with a mate. Having had a few drinks during the day I found the dutch courage to walk into the hotel restauraunt fully dressed. Ray, my mate was totally astounded; I thought he was going to have a heart attack. We had arranged to go out on the town that night, but before we did we went back to the room together. Once inside the door he called me a ****, then impulsively kissed me hard on the lips as he undid his trousers and let them fall to the floor. He ws rock hard and urged me to take his erect member in my mouth. Submissively I obeyed, then he turned me round and taught me what my backside was for.
Afterwards, he told me to tidy myself up as he was taking me out to a place that respected my type of personality. Once out we had a few more drinks then he informed me about the dark rooms in the rear of the establishment. Heeding his dare, I followed him, walking clumsily in my stilettoes. He found an empty room and laid me back on what can only be describd as a hard table. He pulled off my satin knickers and entered me. Whilst he was enjoying this pleasurable moment as much as I, more men entered. Before I could comprehend fully what was happening, I found myself engaged in an ****. My orifices were fully busy and so were my hands as I played with other unexpected, uninvited members. The next morning he admitted that he was ever so glad that I did what I did, as he didn't know how to tell me he was gay. I told him that he had taken my virginity. From that moment on the holiday was a sheer delight. Every evening after dinner we repeatedly visited the same place.
Now, with him being married and me a closet bisexual tranny we meet up for the odd drink and then good sex afterwards. I am still his **** to this day.

Wish it would happen to me. I'd beg to go all the way.

I loved it too. Just wish it would have been me in your shoes. I would have loved to be tied down face down. And taken advantage of.

Great story hun, I wish I could find a guy like that!

I am a guy like that

I got caught when my step-son came home from school enexpectedly one day sick. Funny that was five years ago and nothing has ever been said since.

mmmmmm great story hun i loved it.

wow, i would love that

Yes i could and have done a part 2. Will have to post that soon here just haven't had the time latly

WOW...what a very HOT story!! Mmmmm...luved it !!

Thank you sweety. Hey you never know what adventures lay around the corner when you slip into you next pair of hose and your other fem attire.

I got caught by my mother, that is something I would rather forget about, But I still keep dressing.

Oh yes I did later on but not right away though. What kind of lady do you think I am. LOL. A teasing one. LOL.

This is a great story. Of course you should all the benefits of being a girl, including having sex!

I love your story. I remember when I got caught cding at my aunts house. It was by one of my girlfriends boy friend. Lets say I didn't think what happend would happend