First of all, Ive always been a straight guy. But would sneak my cousins leotards to try on while I was locked in the bathroom.  To growing up and as soon as the girlfriend went to work. Id kock the doors and play dress up for hours. The idea of me being a girl was so hot to me. Woukd pretend to puck out my gf different sexy lingerie outfits just to wear better tfan she ever would ehile she was away. One night while she was too drunk yo realize whatcai was doing,  I couldn't help myself from dressing up in a a blue and white, lacey pushup bra and sone see through pastel pink boyshort panties when we made love.  It was so hot. After while,  Living single, I was buying a new piece of slutty lingerie. The sluttier I looked the hotter I felt. Wigs, and thigh highs with garter belts made me rock hard. I lived dilming myself dancing and stripping to myself while I gooned for hours. I started wishing I was a girl so bad, I never was attracted to men though.  But started getting curious and turned on by trans porn. I wanted women, but wished tge had a nice cock and was confused on what to do. One night I was so horny for cock. The dildos were nice and felt great in my asss and throat, but just wasnt enough.  I needed the real thing. I posted an ad on Craigslist and answered a few while I scrolled the listings of horny men wanting to suck and fuck. Then I got a message. From a man wanting my cock and mouth. I told him my agecand location after he sent me a Pic of what I was to suck and drain. It was perfect. I never saw his face in tge ouc and honestly didnt care because I saw what I wanted. What I needed. He said hed arrive in 15 minutes. Unaware that he was going to get a sissy slutty virgin. I quickly took a shower and made sure I was smooth and trimmed. My cock was throbbing intensely.  I just put on some shorts and a t shirt. So I wouldnt catch him too off gaurd. He arrived at my door, i saw gis truck parkedbout front of my apartment.  This was it. No turning bavk i said as i opened the door. He looked surprisingly normal. Bigger than me. He had a rough look. I would've never guessed he was gay. We sat beside each other as we introduced ourselves.  Hes hand was in his sweatpants strocking his big dick. His massive cock was gard to hide in those grey sweats he wore. I slid my hand inside with his and gripped my first cock in my hand. Omg it felt great. Not thinking twice I was stroking the cock of another man lije I had veen doing this my whole life. I told him I was straight and he was my first man I did anything with. I asked him if I could put on some panties on for him. He said of course. I came back in my black and red crotchless panties with my cock just throbbing with excitement.  I ran and hopped on the cou h with my ass up in the air and my back arched, looking up at him. I started running my tounge up and down his shaft swirling my tounge over his cock hed till slobber was running down to his balls. He wascwearing a xock ricg atound his nutsvand thick ling cock. He positioned himself to where we both started deep throating and face fucking each other. Taking turns on who would push each others faces down on our cocks. His cock was much bigger than mine but we both had nice bigger tgan average cocks. His about 8 inches long and a 3rd more girth than mine. My cock was about 7 and not as thick. My favorite thing to do was place our cocks against each other, double barrel style while strocking them together.  I could take every inch of him, feeling his meat in tge vack of my tonsils.  I sucked him so good and wet , taking turns gagging on his cock and swallowing and sucking his big ball sack. I lived tovedfe him andvwatch him squirming. He begged to pop my sissy cherry and kept asking me to fuck his ass. I kept my boundaries telling him I qas only down for oral. He was cool with it. So we continued to suck each other in do many ways. I wished I had filmed it. He then politely asked where I wanted him to cum. Of course I couldn't resist tellung him to blow his load right in my mouth.  He pulled out of my mouth all of a sudden and jerjed it himself till his face twisted uo and tgen cramming it all tge way in my throat till I felt several hot, thick gushes if milkey cum ,filling my mouth till I spewed sone of it onto his shaft. I had my first mouthful of man milk. I looked him in the eyes and opened my mouth wide ehile drips of cum ran down my chin.nI then immediately started feeling my load blow whike he stricked it , watching my gargle his luad. We both had giant liads of cum dripping everywhere.  He politely put hack on his pants andvasked if he fouks return after taking care of some work. Saying hevwanted me to dress up pretty for him and I obliged. I never heard from him again and never got back uo the nerve to role-play like that again. Even though I fantasize about it daily. I can't wait for another chance like that.  Next tine, my boy pussy will be open. 

Sucking my first cock. Ready for more. Heres how the night went.