Working Alone on Saturday

I opened my eyes to see Bailey Jay looking at me. She winked and smiled as her lovely girl cock taught me my lesson.

"Fuck my naughty virgin ass!" I begged through clenched teeth. "Punish my tight ass with your cock! Yes! Yes! Fuck YES!" I yelled out loud as Bailey Jay began ramming my ass harder and faster.

"You ARE a naughty cock loving dick sucker aren't you Josh?" Bailey Jay belted out. "You like my cock in your virgin asshole even more than down your throat. Admit it!"

"Yes!" I agreed willingly. "Yes I am a cock loving slut who needs your cock in my ass and down my throat! I need and want your cock to teach me all kinds of lessons!"

Bailey Jay continued filling my ass with her hard cock as we both moaned in pleasure. We were louder than we should have been as we fucked one another on the sofa.

She fucked me like a rag doll as I sucked my own cock. I didn't care who heard us scream out in pleasure. Bailey Jay's cock breaking in my virgin ass was all that I cared about at the moment. I could feel another orgasm growing inside my loins.

"Are you ready for me to cum in your virgin asshole you cock loving slut?!" Bailey Jay moaned as she hammered my ass with her cock.

I wanted nothing more at this moment than to feel hot cum shooting into my asshole.

"Fuck my ass and fill me up with your cum!" I demanded. "Show me what a naughty tease I am Bailey Jay! Teach my ass a lesson!"

Bailey Jay was fucking me so hard that my torso had slipped off the side of the sofa so my neck and shoulders were pressed against the floor. I was literally upside down while Bailey Jay stood on the sofa holding my hips as she continued to bury her cock into my asshole. I held onto her ankles with my hands to keep from slipping any further onto the floor.

My hard cock flopped around like a fish out of water, slapping against my stomach and thighs, as Bailey Jay pounded my backside. The saliva coating my cock glistened in the sunlit room. My neck was at an odd angle as I looked up at Bailey Jay.

"Look at you." Bailey Jay breathed heavily. "My hard cock deep inside your ass while you watch me and beg for more."

"You like that just as much as me, you big cock slut!" I said loudly. "You can watch me lick your cock clean after you fill my ass with your cum too."

Just as I said that I could feel Bailey Jay's orgasm shooting into my anal cavity. The warmth of her cum inside me was like nothing I had ever felt before. I climaxed just seconds later as my cum shot in all directions. The sensation of Bailey Jay's cock in my ass while I blew my load took me to a level of sexual release that I had never felt until today.

Bailey Jay let go of my hips letting my body slide off the sofa onto the lobby floor. Her still erect cock made a popping sound as it slid out of my asshole. She carelessly laid on the sofa bathed in sunlight from the windows in my office.

I climbed up between her legs and placed her cock in my mouth. I tasted her cum and the inside of my own ass. I sucked and licked her beautiful cock until it was completely clean.

I enjoyed sucking Bailey Jay's cock until it went limp. I wanted to stay between her legs for the rest of the day, sucking and nibbling on her beautiful cock.

I finally sat next to Bailey Jay on the sofa. We were both exhausted from the intense fucking.

We lazily sat on the sofa catching our breath. Our naked, sweaty bodies were a messy pile of human flesh. That was the most intense fucking I had ever experienced. I closed my eyes and relaxed in the quiet sunlight that filled the lobby.

After a few minutes I stood up from the sofa and walked into my office to grab some tissue. The movement made me wince as I realized just how sore my ass had become from Bailey Jay's lesson. I could feel Bailey Jay's semen run down the inside of my leg. I must have looked a mess after the fucking I had just received.

I could see Bailey Jay slumped on the sofa from where I stood. Her tanned, sweaty body glistened in the sunlight. Her legs were crossed so that it was impossible to see her own cock. Had I not just had it buried in my ass I would have never known she wasn't all woman. She looked absolutely gorgeous and confident in her nakedness.

As I was wiping the semen from my stretched asshole, I heard a phone rung. Bailey Jay sat up and reached into her handbag to retrieve her cell phone.

"Hi mom. No, I am actually on campus now. I shouldn't be too much longer. I am just finishing a meeting with the DSS director now. Yes, he was on campus today and agreed to help me sign up for accommodations." She voiced into her phone as she looked at me and smiled.

I watched and listened to Bailey Jay hoping she would keep her word and not rat me out to her mom. I finished wiping myself off just as Bailey Jay stood up and walked towards me, still talking on her phone.

"Sure mom. Yes, he is right here. I'm sure he wouldn't mind. I'll give him my phone." I heard Bailey Jay say as she walked up to me and held her cell phone out for me to grab.

"It's my mom. She wants to ask you a few questions." She stated teasingly.

I tried to push the phone away to avoid talking with the college president, especially due to what had just happened between me and her daughter. I reluctantly grabbed Bailey Jay's phone as I gave her a look.

"Hello Dr. Smith. This is Josh. How can I help you today?" I said in the calmest voice I could articulate. I was naked in my office with her daughter/son who I had just had sex with.

While I spoke with the college president, Bailey Jay sat on her knees in front of me and started to suck my cock.

I tried to concentrate on the conversation while Bailey Jay wrapped her sweet lips around my hardening dick and fondled my ball sac. Her tongue licked my entire length from top to bottom as she teased my cock back to full hardness She was making loud slurping noises on purpose while I spoke with her mom.

"I think Billy (that was how the president described her tranny son) has provided everything I need to get him accommodations Dr. Smith." I said loudly so Bailey Jay could hear me.

She laughed hearing her mom refer to her as a boy. That only fueled Bailey Jay's assault on my genitalia. She was sucking and stroking my cock while I continued talking with her mom.

"I will indeed make sure that Billy gets all of the support possible through the DSS office. I will see to it personally." I said as Bailey Jay stood up and leaned across my desk in front of me.

She spread her cheeks apart and wiggled her tight little ass prompting me to fill her hole with my hard cock. Bailey Jay looked over her shoulder at me and whispered, "fuck my ass!"

"Uh huh. I agree, Dr. Smith. I think Bailey...I mean Billy should meet with me weekly in order stay on top of his studies." I muttered into the phone as I pressed the tip of my hard cock against Bailey Jay's tight anus.

Bailey Jay pushed against my erection as her asshole relaxed and encircled my hard cock. I pressed my hips forward into her body until my cock was buried completely in her warm, tight asshole.

I had never had my cock inside such a tight warm orifice. Bailey Jay's ass wrapped around my cock and massaged it like I had never experienced. I heard the president talking to me on the phone but I wasn't processing what she was saying. My mind was lost in seeing and feeling my cock buried deep inside Bailey Jay.

"Yes, yes of course Dr. Smith. I will let you know right away if I have any concerns about Billy and his academic needs." I replied into the phone. "I'll hand the phone back to him now. Take care."

I leaned forward, pressing my hard cock even further into Bailey Jay's ass, and set the phone in her outstretched hand. She put the phone on speaker and set it on the desk next to where our naked bodies were pressed together. I grabbed her pig tails in each hand as I started fucking her tight ass.

"Hi mom. It's me. I put the phone on speaker while Josh and I pound out this load of paperwork." Bailey Jay said with bated breath. "I really feel that the extra assistance from Josh and the DSS office will help me get the most out of my time on campus."

"Well I'm glad you finally went there and met Josh." Dr. Smith said. "He has a lot to offer you and will help you in any way he can. Just don't be afraid to ask for what you need, okay?"

"I won't mom." Bailey Jay replied. "Josh has helped me so much already today and I've learned a lot about what he can do for me, I can't wait for classes to start."

Bailey Jay looked over her shoulder at me as she spoke with her mom. I rammed my cock in and out of her amazing ass while I listened to their conversation.

"I'm glad to hear that, Billy." Dr. Smith stated as I continued to impale her daughter/son's ass with my hard cock. "Will there be anything else Josh?"

"No Dr. Smith. I think Billy and I can finish up here and schedule another time to meet next week." I answered as best I could under the circumstances.

"Okay, thanks mom. I'll see you later. Love you." Bailey Jay said as she hung up the phone and tossed it across the desk.

"Oh God! I can't believe we were able to hold a conversation with my mom doing this." Bailey Jay screamed out. "That was such a turn on. I am so glad we met one another."

"You are a wild one, aren't you Bailey Jay?" I said while I greedily fucked her tight ass. "Or should I call you Billy?"

Bailey Jay moaned with pleasure as our naked bodies slapped together. Her beautiful body leaned across my desk while I stood between her parted legs and had my way with her sexy ass. I could feel another climax building inside me.

Billy or Bailey Jay, I didn't care. This sexy human being before me was like a dream come true. I had never known such sexual pleasure as what we shared together. Life was good.

"I'm going to cum." I yelled out.

Bailey Jay pressed hard against my inward thrusts as I started to explode. I buried my cock as far inside her ass and held it there as I started to climax. I could feel my cum shooting out of my cock and into her tight asshole.

"Oh yes!" Bailey Jay cried out. "Shoot your hot cum inside my ass!"

I finished cumming and leaned forward onto Bailey Jay, resting my torso on her back. Her sweaty body was hot. I could feel her body heave as she breathed. I kissed the back of her neck and between her shoulder blades. Her coconut scent was still evident on her skin.

I gathered myself and stood up, pulling my deflating cock from Bailey Jay's ass. A large stream of cum ran down the inside of her leg as I walked around the desk. I found a box of tissue and handed it to Bailey Jay.

She grabbed the tissue and proceeded to clean up the mess we created. I sat in my office chair and took a deep breath.

"My family knows that I am not very manly." Bailey Jay explained. "What they don't know is that I dress and identify as a girl outside of my home." She continued. "I've tried to explain who I really am but they refuse to accept it."

I looked across the desk at Bailey Jay. She was the sexiest girl / boy...whatever, it didn't matter...that I had ever seen. She looked back at me trying to gauge my response. I stood up and walked next to her. I gave her a hug and tried to express that she need only be true to herself, regardless of what others thought.

She hugged me back. I leaned my face near hers and gave her a gentle kiss. Bailey Jay kissed me in return as our bodies pressed against each other.

"So you don't mind that I live this secret life?" Bailey Jay asked me directly.

"I think you will figure out when and how to tell your family." I replied honestly. "I don't care what people call you, Billy or Bailey Jay, as long as we are honest with each other."

"Thanks Josh. I'm really grateful you flashed your naked body at me through the window today." She said as we both started to laugh.

"That's the first and last time I do that!" I admitted. "At least until I know the person, that is."

We kissed once more before finding our clothes and getting dressed. I noticed Bailey Jay pulled her cotton dress on without putting on her bra or panties. Those two articles of clothing she placed in her handbag.

I, too, pulled on my t-shirt and running pants and walked out to the sofa to put on my shoes. Bailey Jay found my ball cap and placed it on my head.

"So when are we meeting next week?" Bailey Jay asked me with a smile.

"That depends." I replied. "You have some paperwork to complete in order to register with the DSS office, remember? Your mom thinks we did that today."

"True. I wouldn't want to do anything to jeopardize all the support you are giving me." Bailey Jay said sarcastically. "How does Friday afternoon sound?"

"That should be great. We can finish getting you set up with DSS and then focus on your ono-on-one tutoring." I joked.

"Oh yes." She yelled out loud. "I need a lot of tutoring, hours and hours."

"Alright Bailey Jay, get out of here so I can finish what I originally came here to do today." I stated as I stood up and hugged her.

Bailey Jay squeezed me tightly and kissed my cheek. She grabbed her handbag and headed towards the front door. As she exited, she turned around and blew me a kiss. I smiled back at her as the door closed shut.

I walked back into my office and sat in front of my computer. I picked up where I had left off hours earlier. Hopefully, I would be finished with the report before too long.

As I typed, my mind thought about Bailey Jay. I had been right all along. The college president did have two sons, only one of them was a sexy tranny.

The End!