Right as everyone was leaving for the day I walked into Ronnie’s office. “My god you look beautiful! Let’s test those lips out.” He said as he undid his pants. I walked over and got on my knees, I took his cock in my mouth and bobbed up and down slurping this time taking it all no problem. “Someone has been practicing I see. God those lips make it so much better” because of those lips drool was sliding out around his cock and running down my face.
Right after that I heard the door open and the cleaning crew came in, I immediately stopped and pulled off mortified. Ronnie grabbed my head, “Don’t stop honey! Hey you two stay a while, isn’t she pretty, this is Reann, remember the young guy that works here this is him after surgery.” He just keep pumping and a few moments later he pushed my head all the way in and shot a load deep down my throat. I whipped my face for cum and spit.
The two Spanish men just laughed. Ronnie told them, “Hey no one has ever broken him in, I am his first cock, how about you two help me break him in. His ass has to be tight as hell, consider it an early Christmas present.” I could hear them walking over as Ronnie let up on my head.
The two men smiled, with a Spanish accent they said, “Holy shit Ronnie, this was that young new guy, my god you gave him the hottest set of tits an ass I’ve ever seen on a chick, let alone a dude. I’m not gay, but fuck that ass looks juicy as hell and those lips were built for sucking cock.” Ronnie looked to them, “don’t worry it’s only gay when there is a cock in your ass, Reann is the only one in the room that will have one up her pussy!”
I looked at them one was tall maybe 6’3” the other one short and fat maybe 5’6” both Spanish and kind of grimy looking. They both started unzipping their pants when two fat cocks plopped out. My mouth dropped and I looked at Ronnie, “But they are too big?” “Not for my little slut, up on the desk you go, and start sucking.” I stood up and the two men pulled my skirt and panties down, I froze, they unbuttoned my top and took my bra off. “Wow look at those tits!” They pushed me and bent me over the desk. The tall one walked in front of me and started jerking his dick, it was getting harder maybe, 8 or 9 inches and really fat. He pushed it into my mouth, I gagged and slurped. The other one started eating out my ass as I moaned. The guy behind stopped licking and walked around with Ronnie, “Take a look at this hunk of meat Reann! And suck that big fat cock!”
As I looked up I thought to myself how is it the short guy has the biggest cock. It was hard maybe 10 inches and as thick as my wrist. Ronnie made me alternate between the two sucking them furiously, chocking, gagging, spitting. The short one walked back around as Ronnie was lubing up my ass. I didn’t notice much, moaning from pain and pleasure while trying to survive the cock in my mouth. The dick in was meeting resistance when it finally pushed into my throat as I chocked and gagged. He pulled back out as I gasped for air and then jammed it back into my throat.
When I felt the cock head at my ass, I tried to protest, screaming but it was silenced into the cock in my mouth as I gasped for air. It pushed against a lot of resistance on my ass but popped past my anal ring letting the head in. I screamed in pain again silenced into the other man’s crotch as I tried to squirm. A wave of humiliation, pain and pleasure swept across me. He just kept pushing, additional tears flowed down my cheeks. “Roque, this ass is so tight, it’s like heaven man you got to try it soon! Now I am going to wreck this white piece of ass thought fucking clean this up white boy!” He shouted thrusting about 5 inches in as I jolted forward on the desk, kicking my legs up in the air.
It felt like my insides couldn’t accommodate any more when another inch when in. My insides felt like they were being ripped apart. My face plowed into the other man’s cock showing no escape from the cocks. He pulled out and rammed it back in getting maybe 8 inches in, pulling out again before ramming me into the other man’s cock again as his balls slapped against my little cock that was just dangling there.
“Wow this is quite a sight, your cocks are impaling this little girl on both ends like an accordion! Why don’t you lift him up?” With that I tried to protest but nothing helped, they lifted me off the desk and flipped me upside down rotating me in midair, I tried to kick and push a little but they clamped my legs down under the man’s armpits and locked me in place, the short guy lined his cock up again and thrusted in as I screamed out in pain. The other man silenced me quickly ramming his cock down my throat again and they two fucked me furiously. “My god look at his little cock bob around, after all those hormones and removing those balls its less a cock and more of an itsy bitsy sissy clitsy!” All the men laughed while I was mercilessly railed out on both ends. Siliva and spit ran down my cheeks the man in my mouth let out a loud moan holding his cock buried down my throat releasing stream after stream of hot jets of cum into my belly.
He stayed there as I continued to chock on his cum and cock. The other man firmly grabbed men around my waist also letting out a load moan, pulling me toward him as hard as he could. “Oh my god what a fucking amazing ass, I going to fill you up!” He shouted as I felt shot after shot of hot jizz shoot deep into my ass. He pulled back out with a pop, making my ass feel empty and then slammed it right back in as I let out a yelp. “Ohh god that ass was amazing.” He exclaimed, the man slowly withdrew his cock from my ass as the other guy pulled out of my mouth. I could feel a stream of cum trickeling out of my ass. I collapsed on the desk after they let me down, exhausted, ashamed and humiliated as I lost my anal virginity.
I heard the door open again, I could hear Renee talking and I knew the other voice too. I glanced over and saw Regina talking to Renee, what the hell was she doing here in New York. Ronnie walked over to my limp body, “Reann, Ryan is a good analyst, but you, god can you take a cock, Regine, glad you could make it today.” Regina looked shocked to see the scene in the office. “Regina, I believe you might know this little blonde bimbo lying here, this is Ryan, now Reann, he made a bet and let’s say he lost more than just the wager, how do you like the transformation?
I covered my face so as to not see her, she walked over. “Ryan is that really you? Ryan it’s me Regina, holy crap they really did make you a woman.” “Don’t look at me please Regina.” “It is you I can tell, wow they did some work with you, I guess you really have changed. I am sorry honey but Ronnie is paying me a lot of money to do what I am about to do, please forgive me.” As I looked up I could see Renee getting a strap on dildo ready and Regina was stripping down.
“Reann, to really break you in I needed absolute humiliation, you didn’t seem to have a high school sweet heart and Regina appeared to be the closest thing, everyone has a price, and we found hers to fuck an old friend with a strapon dildo. With that he slapped my ass and told the two maintenance guys to get out.