Life had been great, living with my roommate.  I could feel freedom and independence, for the first time in my life.  Free to act as young and immature adults, while drinking beers and playing games.  I could watch porn without looking over my shoulder.  Masturbate without worrying if I am being too loud.  But what my roommate didn’t know about me was my newspaper fetish.  Also, he didn’t know the fact that I was bi-curious and liked to wear dresses sometimes.  A fresh new life awaited me.  And I was going to take it as it came.

Days….Weeks….Months go by.  Before I know it, I am celebrating my first year of coming into my own.  Looking back upon what I have built for and of myself as a young man.  Feeling that sense of pride that no one or nothing can take that away from me.  And every night, I do the same.  Beers and video games with my best friend and my girlfriend.  And when night comes, my girlfriend and I pull out the daily newspaper for a little fun.  Pulling out dresses from my closet and putting them on for her.  Posing like a lady, then like a sexy British model.  Then the same, as I strip myself naked and hold on tight to my newspapers.  Each pose, making me feel more and more alive.  And I love her for this. For giving me the chance to express my passion with no insult or judgment.  We end the nights with a kiss.

It was a cool summer night.  Everyone and everything was calm as can be.  My girlfriend comes to the door with 3 boxes and a bag.  I can’t see what is in them and she tells me they are for a surprise.  I smile as I know her surprises are truly gratifying.  She walks to my bedroom and places the items in my closet.  I await her return and wonder what she has in store for me.  The rest of the day goes by, but one thing has changed.  My roommate and I aren’t drinking beers or playing video games.  Instead, he has decided to go out for awhile and leaves my girlfriend and me alone.  She and I sat in the living room and talk about fantasies and newspapers.  I continue with how badly I want to suck cock.  I ask her what it is like, but she doesn’t tell me.  She wants me to experience it for the first time and enjoy it for myself.  Then she gets up and tells me she’s going into the bedroom.  I get up and follow her. 

She sits me down on the bed and turns to open my closet door.  I see the boxes and bag sitting upon the shelf, as she pulls them down and places them on the bed next to me.  “Open them.”  She tells me.  So I start with the small boxes.  I reach in and pull out the most beautiful, long, straight dark red wig I had ever seen.  Curious to the other boxes, I open the smallest one.  And with my hand inside, I pull out a pair of black lavender heels.  I can almost see where this is going, but I hold on to my excitement.  Opening the last box, I pull out a black, petite silk dress with a pearl chain wrapped around the waist.  “Put them on.” She tells me.  I quickly undress myself and in no time, I am wearing a dress, a wig and heels.  “You look amazing!” she says to me.  I quickly look into the mirror and realize I am not a young man, anymore.

  I am Gillian, the woman I pretend to be at night.  She is more real to me now, more than ever.  As I pretend to be Gillian and pose for my girlfriend, she and I become aroused.  And to top it off she hands me the bag and tells me to take the item out and apply it.  I pull out a tube of red lipstick and apply it to my soft lips.  Now, I look more like a woman.

My girlfriend gets a message from her cell phone and she answers it. I assume it is a family member, so I look back into the mirror to admire my new look.  “Oh, Hun?  Can you go out into the kitchen and grab my water bottle and the newspaper? I forgot there was something in the paper I wanted to show you.” She asks.  I do so, walking fully in lady like form.  In the kitchen, I reach for the newspaper.  And when I turn around to grab the water bottle from the fridge, my roommate quickly throws his arm around my waist and puts his hand on my face.  He pulls me in to him and kisses me. 

His kiss was hard at first, to ensure I could not pull away.  Then our lips soften to each other, slowly, as I feel a sense of rightful passion.  To ensure him that I feel good in the moment, tilt my head in towards him and continue our bi-sexual kiss.  Wrapping my arms around his waist.  My newspaper touching his back.  We kiss for what seemed like 5 minutes.

As our passion grew deeper, we kiss more, while moving towards my bedroom.  My lights now off and lit candles now filling the room with black berry scent.  He moves me towards the bed, where my girlfriend is waiting.  She grabs my newspaper and opens them up, spreading them upon the bed sheets.  The 3 of us lay down on our sides.  My roommate and I are still kissing, while my girlfriend lies on the other side of me.  She plays with my wig and my back, while my roommate reaches up through my dress and grabs my hard cock.  He starts stroking and rubbing my shaft.  I unzip him and pull his cock out from his pants.  I stroke him, as well.  Then I move my legs over him, sitting on his waist.  We struggle to undress him, but the newspaper that lay underneath him stays securely in place.  He is now naked, as I move my way down.  Kissing his chest, all the way to his cock. 

I stop and stare at it, working my way up to the final moment that I will dive into it with my mouth wide open.  I breathe hard and with one big breathe, I over come my hesitation.  I open my mouth as wide as I can and force his cock inside of me.  His cock tip plays hockey with my tonsils, as I play deep throat position.  My cock growing harder, knowing that my girlfriend is watching me take another man into my mouth.  She plays with her clit, while she watches in excitement.  My lips moisten, while I go down on him.  I swirl my tongue around, while wiggling his cock in my mouth.  I come up for breathe and hear him moan for my lips and for me to finish him.   

In the heat of the moment, while his cock is still wet, I jump up to my knees.  And throwing my legs around his waist, I do what I never thought I would do.  My girlfriend knows right away, as she rushes up to aid me.  She grabs my roommate’s cock and guides it into my ass, as I sit on top of him, slowly.  His cock fills me up and I ignore the pain for the sake of pleasure.  Then, she grabs a sheet of newspaper and lays it upon my roommate's chest.  Then, grabbing my cock, she begins to masturbate me.  Holding and kissing me, as I take my roommate’s dick in my ass.  My motions of riding his hardened cock are surly pleasurable. 

I ride and ride him like I am a woman, riding a horse in a fantasy dream.  My ass tightens as he is about to cum.  And I feel my orgasm arriving, as well.  Then right before he cums , he bursts out a tough grunt, pulling my ass hard into his waist.  His cock has achieved new depth, as his cum shoots out, filling the walls of my inner ass.  He squirts into me several times, before pulling out.  I can feel his cum running down, lubricating my inner walls.  It is an amazing sensation.  So amazing, that I begin to cum all over the newspaper laying on top of his chest.  The 3 of us lay there, pulling newspapers from under us and playfully rubbing each other with them.