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First time with a man

I have been crossdressing since the age of 11 years old. I never really considered myself anything other than straight. Up until I turned 19.

I often fantasized about other guys when I was dressed but that's as far as I took it.

The year was 1984 and one day I decided to stay home from work to play. I get dressed up in a pair of purple satin string bikini panties,matching bra,black thigh highs and garter and a short silk spaghetti strap nightie,that barely covered my ass.

After playing around the house for a couple of hours I decided to head out to a local adult bookstore to find some crossdressing magazines.I just put a pair of sweats and a sweat shirt over top my sexy outfit and head out to the store.

Once I arrive,I start browsing the magazine racks and I notice they had a movie section in the back for viewing movies. I was always curious about these places and I figured I would see what it was all about.

I head over to the clerk and get some tokens to drop in the machines and head to the back.

Walking down the hall I notice some gentlemen standing around,some fondling their cocks through their pants.

I look over the movies and find a booth,as I turn around to shut the door I notice an older man enter the one next to me,about 60 years old,but I thought nothing of it.

Once in the booth I drop my tokens and proceed to find some shemale movies.I start to get aroused ,so I take off my shirt and pants and start to play with myself in my sexy outfit.

I then notice a hole in the wall and I can see the guy jerking his cock and taking peeks through the hole.

I then say to myself,"what the hell" and I turn towards the hole,spread my legs and start rubbing my cock through my panties.

A few seconds later he sticks his cock through the hole,I think,here's my chance.

I take it in my hand and start to stroke it,after a minute or two I hear him say "suck it bitch", so I kneel down in front of the hole and take him in my mouth,tasting his salty precum.

He moans as I go up and down on his hard cock,for about 5 minutes I suck on him,when I feel the head of his cock start to pulsate and feel the warm rush of cum hit the back of my mouth.

Doing as any good slut should do,I swallowed every drop.

He pulled out and said to "be here tomorrow night 8:00pm" and I told him I would.

So the next night I arrive and we meet up,same booths ,same thing,suck him dry.

This went on for about two weeks,maybe 5 nights total.

On one Friday night we met,he met me outside the store and asked if I would join him in his van,that he wanted to go further with me.

We get to his van and he immediately takes off my sweats,revealing my sexy white satin panties and bra,white crotchless pantyhose and a yellow sundress,all neatly tucked away under my sweats.

It smelled of sex in the van,a smell that turned me on. I could see cum stains on the carpeted floor and the sheets that covered the little bed he had in the back.

He laid me down on the bed and took off his pants and shoved his cock between my lips,fucking my mouth.

Only moments later,he is rubbing some sort of lube on my awaiting ass and his stiff cock.

He flips up the dress,slides my panties as best he could underneath the hose and slips his cock into my wet ass and as his balls smack my ass I explode in my panties,soaking them.

My legs spread and up in the air,he is pounding me for all I'm worth,I'm moaning loudly and the van is swaying back and forth.

I'm screaming in pure pleasure as this 60 year old man fucks my virgin ass,"fuck me,fuck me harder baby".

Twenty minutes or so have gone by and he starts breathing heavy,saying he is going to cum.I tell him "don't stop baby,keep fucking me",and he starts to pull away I wrap my legs around him and pull him in ,deep into my ass and maon,grunt very loudly " DON'T STOP".

I then feel his cum start shooting into my ass and I start to buck widly as he fills me up.

He dumps what seems like a gallon of cum into me and then pulls out and collapses beside me,telling me I was the best ever.

I get up,situate my outfit,fix my panties and tell him thank you and we'll meet soon.

I exit his van without putting on my sweats and head to my car,feeling his cum drip into my panties.

We had a short lived one year sexual romance up until I married the woman of my dreams.

But to this day still,I love to dress up and have sex with men.

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Comments(19)


stockingluvr
Posted 15 Feb 2013 11:17
Great story, hope you cum back and write some more.
sweetsue
Posted 23 Jan 2013 13:08
I started dressing about 10, was just before my parents divorced. I went with my dad because he allowed me to dress when I wanted. When I was 17 he entered my room to check on me wearing only his boxers, I was wearing a babydoll nighty. I woke up and could no longer hold myself back as I took his cock in my hand, then my mouth. He was well hung and I took all of his uncut cock. Was the first cok I ever had he filled my mouth with wonderful juice. Two nights later I joined him in his bed and he filled my ass with his cock, then with his cum. After that he kept me well dressed in outfits he liked, he even took me shopping for my first heels. I lived with him till I was 26 and was the only man I ever slept with till my wife turned me into her whore.
divya
Posted 02 Jan 2012 15:57
im also a young hot sexy crossdresser who loves to suck cock n get fuckd hard in d ass...so ny one who wud want to b d lucky one to please me...cntact me on my email address... stunningdivs.gupta@gmail.com
PlayfulAshley
Posted 02 May 2011 19:04
MMMMMMMMM..... Amazing story, so jealous
nticeme
Posted 22 Mar 2011 11:16
thats one very horny story ..
badboy44
Posted 31 Dec 2009 07:45
I would have loved to been involved in a three-some in the van. I would have loved to sucked both their cocks while dressed in tan thigh high nylons, pink panties and a white garter belt. After sucking their lucious cocks, I would let both fuck me up my tight asshole until they dumped their hot cum inside me.
horney in thi highs
horney in thi highs
Posted 19 Aug 2008 01:24
oh buy the way horney in thi highs posted the last comment
Posted 19 Aug 2008 01:21
i wish i was there, we could explore every inch of each other! i have never had a real cock in my ass, would you like to be the first? lets dress up and enjoy everything and anything as loog as you cum deep inside my ass and my mouth. lets meat soon. i need it. sound good?
Posted 15 Aug 2008 14:24
to horney in thi highs. You could certainly lift my short skirt and pull my panties to one side and slip your meat into me. You could fuck my arse as much and as often as you like and I would suck you off while you wear panties and stockings. i love it. i also have a beautiful dildo that i slip up my arse every day but absolutely nothing can compare with a real live hard cock. i am now going to slip my dildo into my arse and wank into my panties and then eat my spunk.
horney in thi highs
horney in thi highs
Posted 04 Aug 2008 23:36
i am so horney ! i want a cock up my ass so bad. my dildo is nice but the thought of a real cock pumping in and out of my ass doggie style while his hands are locked on my hips till he cant hold back anymore and i feel his hot cum fill my ass. then i would do him the same way. anyone interested?
katlinmarie
Posted 12 Jul 2008 23:30
good story. i would love this to happen to me.
horney in thi highs
horney in thi highs
Posted 03 Jul 2008 22:19
tell me what you would do to me,and what you want me to do to you
alice
alice
Posted 03 Jul 2008 11:17
being a CD, I love sucking and getting fucked
horney in thi highs (nj)
horney in thi highs (nj)
Posted 15 Jun 2008 22:33
CUM on now , i thought FOR SURE some one would have felt the same way. THIS IS THE TRUTH ,I HAVE NEVER TOLD ANYONE OR POSTED HOW I FEEL ON ANY SITE,EVER!i NEED A COCK UP MY ASS SO BAD! THE DILDO FEELS SO GOOD RITE NOW . BUT I WANT TO FEEL A OLDER MAN CUUUUMMMMM INSIDE ME EVEN MORE SINCE IVE BEEN FUCKING MY ASS WITH THIS THICK TOY. I WANT IT DOGGIE STYLE THE FIRST TIME. AFTER I SUCK HIS COCK FIRST TILL HE CUMS IN MY MOUTH. THAT WAY HE WONT CUM REAL FAST WHEN HE FUCKS ME. I LOVE TO DO COKE AND DRE
horney in thi-highs (NJ)
horney in thi-highs (NJ)
Posted 16 May 2008 15:54
9NJthei wrote on the 10th what i am into trying, and that was my first time ever letting it be known to anyone how i want . now someone has posted a comment about what i wrote. that made me very horney . just thinking about a guy also dresseed up ,him doing me and me doing him made me buy a dildo and fuck my ass lastnight. when i came i put all over the dildo and fucked my ass AGAIN! the past few days all i think about is being all dressed up as i get fucked for the first time, then me fuckin
Posted 13 May 2008 15:37
I love to cross dress and suck a guys cock. I would like to meet this guy and have tranny sex together
Posted 10 May 2008 01:04
i would love to dress up and get fucked by a horney guy, just once, i think (i know) i would love it! sheer pantys,black thi highs,short skirt,pumps,and a hard cock doing me doggie style,then i would get on top and sit down on it!most of all i want to feel him cum inside me.

nicola
Posted 29 Apr 2008 17:42
Sounds like a blossoming relationship with Mr "anonymous" :-)
Posted 29 Apr 2008 16:16
i wanna fuck u up the ass too
 

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