I First Dressed As a Girl For My Friend.

One day when I was staying at my friend's house.  His mom had already gone off to work and Terry and I were still sleeping.  The night before he and I were watching the Crying game.  We thought that would be real cool to have sex with someone like that as he thought the guy playing the girl looked realy sexy especially with the scene where he was wearing black pantyhose. Well this got me thinking.  That morning I got up and notice he was still sound asleep. I used the bathroom and after I was done.  I checked to see if Terry was up.  And he wasn't as he really liked to sleep in.  So I got the key from his key ring to the apt door, got dressed and went up towards the mall.  I could walk it as he didn't live that far away.  As I got to the mall I went to payless shoe store and was checking out some of their heels.  As u can find some good ones at a cheap price.  I picked up some black 3 in high heels and some black 3 in strappy platform style heels.  I then went to spencers which is a anything that is cool type store.  They still had their wigs out on display that they had for halloween so I picked up an auburn colored wig that was shoulder length.  Then I went up to jc penny's And went to their pantyhose section.  And picked up some black, biege and a coffee colored pantyhose.  Surprisingly I didn't get any looks then I went up towards target and got the rest of my apparel.  Which were a few skirts and blouses from the discount rack and some make up eye shadow, foundation, blush, eye liner ect.  Also picked up a back pack to put my fem things in.  After I paid for my stuff I put my fem things in the back pack and walked back to the apt.  As I got there and went in he was just starting to get up.  I put the back pack in the entry way closet.  After a while when he was more awake I mentioned to him that we should watch the Crying Game again.  He agreed.  While he went down to the video store to go and rent it as he called to make sure it was there.  I went and jumped in the shower and started to get ready by shaving my body as I was getting 19 yrs. old and was getting some hair in places but not much.  After I got out of the shower I dryed off.  I pulled out the pantyhose and decided to wear the black control top pantyhose.  Felt so good sliding them on and pulling them up my legs I then put on a bra that I also purchased that was black and lacy.  Then put on the white blouse and next the black mid thigh skirt.  I made sure everything was adjusted right.  I was starting to get nervouse as I heard him come back.  He knocked and asked if I was almost done I said yeah go ahead and start the movie he said ok.  Be nervous makes putting make up on hard but I got it done.  Then I put on my auburn shoulder length wig and combed it a bit then I put on the  black 3 in strappy platform style heels.  I checked myself over and took a deep breath and opened the door and walked out into the hall way.  I noticed he was in his room so I went into the living room and checked myself out in the mirror and liked what I saw.  I noticed the movie was playing in his room so I went to his door and noticed he was making his bed I opened the door and took a deep breath and asked if I was as pretty as the trans on the movie.  He turned around and giggled and smiled.  I noticed that he couldn't stop looking at me though.  He kept looking at my pantyhose legs.  He asked do u like wearing that I told him yeah and that I have been dressing like this for a while.  I walked towards him letting my nylon legs rub together as I did so you could her the swish sound they make.   I told him that is how I got started was by wearing pantyhose and then just started to crossdress after that.  I told him if u like u can rub my legs if u want to .  He looked at me then knelt down and started to caress and rub my pantyhose covered legs.  He said that my legs felt so soft and silky.  I couldn't tell you how good that felt.  He then stood up and was looking at me face to face I leaned forward and kissed him on the cheek.  The he looked at me and leaned forward and we started kissing right there.  Oh I thought I was going to die of just the sheer excitement of dressing up for my friend.  After a bit of kissing I asked if he would like to lay on his bed he said yeah.  As we laid down on his bed we started kissing a again and I lifted up his shirt and started making my way down.  I pulled down his jogging pants and underwear and started kissing his ****.  I heard a big breath and a moan come out of him.  Then put my mouth over it and started sucking on his ****.  Seeing some of my lipstick on his **** as I would be going up on it and then letting my lips slide back down it.  After a bit I quit and came up and we started kissing again.   I then asked if he wanted to **** me as he was so horned up it wasn't a hard question for him to answer to so I stood up and took off my skirt and left my blouse and hose and heels on and made a hole in the back of my pantyhose for him to enter into me.  He put a rubber on and got me in doggy style position as my legs were kind of hanging of the bed and he lubed up his **** and stuck it in slowly oh my god it felt so good.  I couldn't believe this was happening as I didn't think my friend who was actually my best friend would be ******* me.  He started to go faster and a little harder I could hear him breather harder and feel his hands grabbing onto the side of my pantyhose hips.  Then just like that he came.  I felt good knowing that I made my friend ***.  He laid on the bed and I laid next to him gliding my finger tips across his body and watching him get the chills from it.  I pulled off his rubber and started to suck on his salty tasteing ****.  I could hear him starting to moan a big and next thing he was getting hard in my mouth.  Which is what I wanted as I was still horned up.  I grabbed another rubber he had laying on his night stand and slid it on his **** and I climbed on top of him.  He just let me do it to with not a care in the world.  I started to ride him which felt so good as he was hitting my male g spot.  Now I know why women like to ride.  He had his hands on my hosed legs rubbing them as I rode him.  I felt some pre *** coming out and could feel my self getting ready to ***.  After a few more minutes I cam and then he came after seeing and hearing me ***.  After we came I leaned forward with him still inside me kissing him on the lips squeezing my cheeks together on his **** as he was still ******* and as I was still going up and down on it a little.  I then climbed off him and went into the bathroom the change and clean up.  After I was done in the shower I came back in and he was laying on the bed.  I put the back pack that had everything in it except for my pantyhose that I laid across a chair in his bedroom after I washed them up.  He was looking at them and asked If I could dress up for him again later on as his mom wasn't going to be back until late that evening.  And as it was raining outside.  I said yes as who am I to say no being asked to dress up.  So later on I dressed up for my friend and pleasured him a few more times that day and into the night. 

silkiehosewearer silkiehosewearer
31-35, M
25 Responses Jun 30, 2009

Wow,super hot story,feeling quite horny after reading that

Awesome story so hot! wish it could happen to me! It sound very close to my ost common fantasy!

Thank you 4 your comments i do appreciate them sorry its been so long i have been real busy laltly sorry

I once had a friend many years ago that I liked to dress up for. I always started by sucking him off then he would **** me silly all night long. I really miss him, he always said that he wanted me to be his wife, *sigh*

Well I got all hard reading that, thanks.

Thank you all for the comments. And yep u guys have that right brave girl indeed as that could have went south if he wasn't into his friend dressing. But i am glad it did got the right way which would be north? lol. But yeah it was alot of fun after that. He loved having me over for visits after that experience.

wow, what a hot story, that really turned me on!

Same Here

Now that is the type of story that makes me feel bad for the possibilities in my youth that I had and never took advantage of, being with girl or guy. I dont know if it makes sense at this age to try and recapture, its not as easy and a heck of a lot more dangerous.

Well i still visit with him now and then. Maybe I will ask. wink wink

mmmmm. that was so sexy! If your friend wants to take on 2 gurls, let me know

Oh you could say that. Oh wait you did. LOL. All kinding aside I was just taking things on a whim and a chance and I just happened to luck out. But yeah nerves of steel in deed.

great story. you must have had nerves of steel

Lucky girl

I am glad you enjoyed it hon. xoxoxo

loved the story almost came in my panties reading it xoxoxox!

Thank you for your comments. Yes I was very lucky and fortunate to have a good friend like that. Very lucky.

Great story. It almost seems too good to be true.<br />
I wish i had a great friend like that

Just fantastic! I really loved reading this!


Well Congratulations I wish I had a friend like that. Good Luck in the future. Samantha

What a wonderful experience. Those are the kind you always cherish forever. And your reminded of them every time you dress. I am very happy for you.

Sorry to hear that jill but am glad u got to have a good experience with ur friend. And yes Lacey I am still friends with him we keep in touch and every now and then I do dress for him as he likes it.

almost the same thing happened to me when I was 16 but my friend was a lot older he spent a fortune on me over the next five years on lots of lovely things for me to wear for him.We only split up when his wife found our love nest gosh how I miss him

great story. you were so lucky to have done that at such a young age. Do you still that friend ?<br />
<br />
Lacey : )