Picked Up By Two Straight Boys While Dressed As A Woman

I am a 40 ish tgirl and have been thus way all my life. Finally I am looking at at the gender reassignment operation and will eventually take that final step to being a fully functioning woman
Thus though is one of my many adventures as Karen growing up in north east England
One night I popped on my favourite little green mini skirt, sexy top, black sheer tights ( pantyhose) and black hi heels, made up my face, popped on my sexy long wig and wiggled down the streets for a midnight walk
It wasn't too long before I got some interest from a passing car. It slowed down, and then stopped a few yards in front of me. I walked on excitedly
The window came down on the passenger side and I was surprised to see two young lads in the car. I must've had bravery pills cos when they asked if I wanted a ride I got into the back of the car, sitting behind the driver. I was offered a ciggy and took it, lighting it and telling them I was called Karen and was just on my way home after visiting a girl friend.
I asked them to pull up eventually and thanked them for the lift and got out. Now it never I thought
The driver, as I started to cross the empty road, called me back and asked me if I fancied some fun
I said I didn't do 3sums as I stood in front of him, my skirt at his eye level. Just then a gust if wind blew my skirt a bit and while I got my hand there in time to stop him seeing my little bulge it did give him a great look at my thighs and my whole sexy legs. I giggled at this and said goodbye but as I was crossing the road I heard the door open and close behind me
I walked down a little alley as the driver caught me up
He soon had me in a clinch up against the wall and had his tongue in my mouth in seconds
He was very good looking and obviously wanting sex right there
I pushed him off and said I was on my periods but as he held me his hands started wandering over my **** and my bum and round to the front
I pulled my groin back as far as I could and tho he brushed over the front if my tights and knickers he didn't feel the **** tucked away before I pulled his hand away
Just then his mate came round the corner and saw us in a clinch
You owe me a fiver my man said
I don't know if they'd bet I was a man or just a slag either way they now thought I was a woman phew!
I said I'm not doing 3sum and the other guy was debt back to the car
As he left I put my hand on my boys **** over his jeans
This sent him wild and he pushed me backwards saying yes **** me, suck me
We came up against some stairs and I sat down unfastening his jeans as I did so
I pulled them down plus his boxers and took his lovely clean hard **** in my mouth
He leant over me and put his hands on one if the higher steps and literally ****** my throat
I choked a couple of times but soon got into a rhythm and started rubbing myself knowing he couldn't see what I was doing
Soon he started to pant and groan and I knew what was coming
He squirted lots if jets of thick *** literally down my throat and I gulped it all down eagerly
When he finished he asked if I would do his mate if he sent him back from the car
I said yes but got a bit scared as I had pushed my luck already so after he left I ran away down the many back alleyways
When I got home though I discovered my panties were soaked. I had *** at the same time I was gulping his *****
This us a true story and only once more did I put myself in a position with two unsuspecting men, that time in the back of a transit van but that's another story!
Hope u enjoyed this everyone
Xx Karen xx
Karenbabes Karenbabes
41-45, T
11 Responses Jan 23, 2013

lucky lucky girl

Very hot...but very scary for you

Thank you Karen. I loved this story. I love tgirls and have some regrets that I didn't become one. A little late for me now in life but enjoy being a sissy!!!! I like dressing up sexy and slutty for guys. However my sexual passion is to be dominated and emasculated by another MtF transsexual. This only applies in the bedroom. Hope when you have SRS it goes well for you. You go girl!!!

Aw thanks kristin

I would be happy to share that bedroom with you babes


lovely hot story Karen,i'll have to make a journey up to the north east

Jayne xxx

That would be wonderful I would love that Jayne xx

It is fun teasing the lads and getting away with some fun. Only been caught twice and I was lucky the guy was so into it, ended up on a few dates later

I agree terri I love how easy it is mostly - offer them a blow job and they forget about wanting to get inside your knickers!! Lol
Only caught out once and he just told me to get out the car
Came close another time when a guy had quickly thrust his hand between my legs. I had a very short skirt and tights on and he ended up with his fingers rubbing up and down kind if down the side of my knickers but feeling a little bit of hose, a bit of knickers and a bit of my ball sack. I moaned like hell to convince him not to move from that spot and he thought I was having an ****** while all the time I was wanking him furiously so he would ***!!
Fortunately he came quick and moved his hand away so I took the opportunity to get my head down, stop him from getting his hand back between my legs and tasting his ***. Result in the end lol xxxx

Don't you just love that taste, yes i try now to make sure I pick guys who just want blow jobs or they want that something special

From my first time, yes I've loved that taste xx

I vote for the something special:)

1 More Response

What a beautiful experience, thank you for sharing

Loved it, now im off to have a read of you other stories ; )

loved the story. Glad it was true. I wouldn't have had the nerve!

Thanks Hun xx

I loved it!!! awe the lad was a lucky fella!! if I got a blow job from you!! I would love to return the favor!

That would be sweet thank you xx

if I met you.... I would actually would love to suck you off first.

lucky you i would of done the second one to

Ha ha ....... Tart (lol) xx

mmmmmmmmmmmm, nice