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Back in high school, when I was very scrawny, 5'6 and less than 110lbs, I grew my hair long because I was into metal, it's dark brown and came to about half way down my back and I often painted my nails black.
Girls were never very interested in me, they'd be my friends and hang out to get high with me but that was about it.
One day I work up the courage to ask one of my hot chick friends out thinking "what's the worst thing that could happen"
At first she laughed at me and told me to fuck off, she didn't think of me like that, we were just friends, plus she had a bf.
Crushed my self-esteem, whatever.
A week later, she comes and talks to me during lunch.
She tells me her douche bag jock boyfriend was cheating on her and they just broke up, and wondered if I would still give her a chance.
She wants to try a "nice guy". Over the course of a month I used all the money I made working at BK on her. I took her on a date every weekend,
bought her a new purse 3 or 4 weeks into the relationship, she asks me to stop by her house this weekend so we can watch a movie on the couch and informed me her parents would be gone all day.
I get there and even though we weren't going anywhere she was wearing a pretty dress and had make up on.
I was mentally preparing myself to make a big move.
We go to her bedroom.
She just sits down on the bed and stares at the floor for a few moments.
uh oh.
I ask if somethings wrong, assuming she didn't want to see me anymore.
She says "Can I tell you a secret"
I say "Sure"
"I think I'm bisexual. I keep having feelings about girls... but I like you too"
I didn't know what to say.
She says "So, and it's totally okay if you're not okay with this, but um. My fantasy is kind of doing it with a girl with a man part"
"And you're not like the other guys who are all big and hairy and stuff"
"So I was thinking, if its okay with you, would you mind dressing up like a girl and.... fucking me?"
Blood instantly drained from my head to my dick, those last 2 words were what I had been wanting to hear for the last month, only with a real twist.
I tell her sure I don't mind. It's weird but I'd do anything to fuck this girl!
She jumps up and bounces around and kisses me.
She walks over to her dresser and pulls out a black bra, more or less a training bra, or a small A cup (obviously not hers, she has huge full tits) a black spaghetti strap tank top, a pair of thigh high fishnet stockings and a black semi-transparent thong. I think she had this planned out for a while.
She hands them to me and asks "One more little thing?"
I was dreading what it was but so eager to fuck her I say "Anything you want I'll do for you"
"Before we do it I want you to be as much like a girl as possible. I want you to shave, everywhere."
I agree and she takes me into the bathroom, I strip off my clothes and she draws a bath.
She gets out a couple of her razors and I get into the tub, I start with my pubes and legs while she does my chest.
I wasn't very hairy so it didn't take very long before I was completely bare, my legs, pubes, chest and she does my back and my butt.
We go back into the bedroom after I towel off.
She can tell I'm nervous so she takes off her dress first, and then her bra.
Standing there topless in front of me was all the motivation I needed.
She helps me dress up in her clothes I can tell she's very pleased with the results. Everything fit very well.
I looked very feminine and could have probably passed for female with the exception of my raging hard on.
She gets down to her panties and we crawl on to her bed, and start making out.
She wrapped her arms around me and kisses me for a long time using plenty of tongue.
She takes off her thong and has me eat her pussy while she gropes my chest, my legs and my butt, and strokes my very hard cock.
After a few minutes of licking her sweet smooth pussy she tells me she wants me inside her.
She pulls pulls my panties down and directs me to her nice wet pussy.
It was the greatest feeling in my life sliding into her nice tight cunt.
and it felt amazing being completely shaved and fucking her equally smooth body.
I could really see why girls fuck other girls, it was so clean feeling and it made every touch electric.
She kept saying "I wish you were a girl! I wish you were a girl!"
Being very into her fantasy I whispered in her ear "I am"
She's gasping and moaning like crazy and just screams out "I want to fuck your pussy so bad"
As eager as I was, I try to make it last nice and long to give her what she needs.
She goes from being on my lap riding me, to letting me fuck her from behind, all the while she's touching me everywhere.
She looked into my eyes and says "Can we take this a little further?"
I couldn't deny her no matter what she asks of me "Anything for you" I say
She makes me back down for a minute while she reaches over to her bedside table and opens the drawer.
I wasn't expecting when she produces a bottle of lube. (I was expecting handcuffs or something like that)
She gives me an inquisitive look and I nod my approval.
She squirts a generous amount on her middle and forefinger and reaches down between us and finds my asshole.
She slowly and gently parts me with her finger tips at first, then her entire fingers, just like you would finger a pussy.
The fact my cock never pulled out of her and her fingers made their way in made it very bearable.
She starts saying "You have such a tight pussy! Fuck me as hard as I'm fucking this pussy!!!"
I was rocked with waves of pleasure as our thrusts and her fingers worked in motion together until I couldn't take anymore and exploded inside her.
We laid there on her bed in each others arms, staring into each others eyes, no hint of embarrassment from either of us.
We had just done something for each other that we would both never forget.
After a while of content silence she asks me how I felt about what we had done and if we could do it just like this again.
I'd give her anything, I'd be anything for her, as long as she were mine.
I started wearing her underwear beneath my clothes regularly for her pleasure, in school, on dates, and especially in the bedroom.
We've been together two years now our sex lead her to start experimenting with her female friends and we started having many great nights of threesomes (those nights I didn't dress up) and she's enjoying pussy almost every day.
Would anyone not do what I'm doing to get what I'm getting?